Podcasts about inverted

Play Episode Listen Later Mar 3, 2026

Anna almost loses Jake, then beds him.By darrenr - Listen to the ► Podcast at Steamy Stories.Wordlessly they lay there, Anna clutching his hand as he held her. Eventually her breathing returned to normal, and her grip softened. Jake realized he had his dick pressed against her bottom in their hug, but it had softened during the past few minutes. He felt proud of himself and his soft dick. Anna was the epitome of his sexual desires, but in this moment even his perpetually rude cock recognized this was not the time to make selfish demands. It felt nice snuggled up against her soft bottom.His face resting on Anna's back, he couldn't help smiling. He had done it! He had most definitely given her something she'd never felt before.A small movement from Anna brought him out of his reverie, and he realized she was crying. In a single second his heart fell from impossible heights of blissful pride and satisfaction down into despair.“Anna, are you okay?” Jake asked, his voice small. “Did I hurt you?” For what felt like an eternity, there was no response at all. Then Anna's grip on his hand tightened, and she pulled it against her chest.“Thank you,” she said, her voice cracking. Holding his hand tight, she moved to sit up and he pulled back to give her space. She looked at him with cheeks wet with tears. “I have no idea why I'm crying. No, you didn't hurt me. You made me feel more pleasure than I ever thought possible. I don't know where all this emotion is coming from.” She leaned her head against his shoulder, and he put his free arm around her again. They sat in silence for a few minutes more. Jake's heart gradually recovered from its moment of terror, and he breathed easy again, the sweet scent of her hair in his nose.With a deep breath Anna lifted her head and looked at Jake. Still feeling elated from his success, he started to grin. This in turn made Anna smile.Making a goofy face, he said, “Well?”They both burst out laughing. Jake felt elated at what he had accomplished, giddy with delight at what they had shared, at how close he felt to Anna.When the laughter died down, Anna's face grew thoughtful. “What I just experienced, was that normal? Is that what everyone feels when they orgasm? Is that what you feel?”“I doubt I've ever experienced anything even a tenth as good as that,” Jake said. “That seemed to be in the earth-shattering category.“It really was. My legs feel weak. I can't get over how good that felt. I honestly didn't know anything like that was possible. How did you know how to do that?”He thought about all the ‘how to' videos about sex he had watched, all the guides to please a woman he had read, how he poured all his love and focus into doing the best he could for her. “I think I just got lucky.”Anna laughed. “No, I'm the one who got lucky.” She sat in silence for another moment looking at her toes.“Jake?”“Yes?”“You kissed my pussy.” It still caught him off guard when she used that word, but he liked it.“Yes. I hope you don't mind. I knew you needed more and that was my only idea,” Jake said.“Was it, was it gross?” Anna asked.“Quite the opposite,” Jake said. Of course, the truth was he was overflowing with affection for her. Confessing all that now seemed too much. He kept silent.“Anna,” Jake said quietly, “Did I hurt you?”“What on earth are you talking about?” she said.“You know, when I, when I put my finger inside.”“Oh!” she giggled. “No, it didn't hurt at all. Quite the opposite. Completely different from the doctor.”“Oh good,” Jake said, his finger remembering. Warm, snug, delicate. He felt his arousal start to grow and tried to think about something else instead.After a few minutes, Anna asked, “How tired are you?”“Oh, I'm fine.”“But it took me ages to reach the climax. You must have been getting a little tired?”“A little,” Jake admitted. “But I'm fine now.”“All recovered?”“Yes, all recovered!” Jake said, laughing at the interrogation.“Good!” Anna said, distractedly stroking the top of her thigh. “Good, I'm glad. That was an incredible thing you did for me, just an incredible thing.”“Anna, please,” Jake protested, turning his head to meet her eyes. “I enjoyed it too, you know.”Anna smiled but quickly looked away in embarrassment. “Of course, now, now it's your turn.” Anna was clearly getting nervous. “I owe you some–”“No,” Jake said a little too firmly, sitting up. “No, listen. There's nothing owed. Nothing transactional here. If some day in the future you find yourself needing to touch me, truly deeply needing it, then nothing would be more welcome. Nothing. But I've been slapping this salami and having orgasms for years. I'm fine. What's important now is you've taken a huge risk with this first step, and it was a good experience. I think you should load up on good experiences before taking more risks.”“'Good experience' rather understates things,” Anna said with a laugh.“Here's what I think,” Jake said. “No offense, but you look a bit worn out. How about I get us a snack and we watch a movie to relax?”Anna smiled. “I do feel a bit drained. That would be nice.”Jake returned with some apple slices, cheese, and crackers. Anna cued up a movie and he realized he was feeling pretty drained himself.Sometime later he awoke to find Anna still sitting with him. The movie was over. It took him a moment to notice she was looking down at his crotch.Jake must have moved a little because Anna startled, looked away, and began to get up.“What's the matter?” he asked.“Sorry, I shouldn't have been staring while you were asleep.”Jake laughed. “Are you joking? We've been naked with each other for weeks now. Why would I mind if you looked at my ugly wiener?”“I don't know,” Anna said, settling back down on the couch beside him and leaning against him. “It just felt like peeping or something.” She smiled. “I guess I was being silly.” Jake nodded and put his arm around her again, feeling her shoulders rise and fall as she breathed, enjoying how her breasts moved.“I don't think it's ugly,” Anna said after a few minutes.“Huh?”“Your penis. Your cock,” she added with a smile. “I don't think it's ugly. It got super small while you slept. I thought it was cute.”Jake felt the topic of discussion begin to swell. He whispered, “Uh oh, it knows you're talking about it.”Anna bent down close to his dick and whispered to it, “I think you're cute when you're all shrunk up small!” Then she sat back up, giggling.His dick jumped a little in response, and Anna laughed more.“Can I tell you something stupid?” Anna asked.“Of course.”“This is embarrassing, but, when your cock gets really big…” Anna looked down. In a quiet voice, she said, “I feel a little bit scared of it.”Jake immediately began to shrink. He frightened her? He moved to cover himself with his hands.“No wait,” Anna said, grabbing his arm and pulling him back down. “That's not what I meant. You didn't do anything wrong.” She pulled his hands up so his crotch was exposed again. “All I meant was it's intimidating when it gets big.”Jake thought for a moment. “I have to be honest. It's hard to not be aroused when I'm with you. But I will try!”“No,” Anna said. “No, I don't want that. This doesn't make sense, but I also like when it gets big. I feel both excited and a little afraid.” She looked down and then back into his eyes. “I guess what I mean is I appreciate how patient you're being with me. I intend to return the generosity you've shown me, but, but I'm just not ready yet.”Jake let out the breath he didn't realize he was holding. “Oh, well that's no problem. I thought we already settled this? You don’t ‘owe’ me anything.“"I know,” Anna said, “I just–”“Listen,” Jake interrupted. “Believe me. I’m having a… profoundly good time. All I can think about is hoping you’ll invite me back for another round.”“What does your schedule look like tomorrow evening?” she asked.Jake chuckled, and he felt his dick jump at the thought. “I think I can fit you in,” he said.Anna smiled, and leaned her head against his shoulder again.Unexpressed Desires.Anna didn’t like to directly ask for Jake to work his magic on her. Her face would occasionally get this hungry look that was extremely obvious, and Jake made sure to offer. As he practiced on her more and more, he became immensely proud of his growing expertise. He had learned to read her feelings, her body’s reactions, and her needs. Sometimes it was clear she needed immediate relief, and he would give it to her. Other times, his favorite times, she enjoyed dragging it out. He would bring her right to the edge, and then back away, teasing her over and over until she couldn’t stand it even one more second. When she reached that point, he would take her over the edge into an incredibly powerful orgasm that left both of them exhausted afterwards.She wasn’t ready to return the attention. Occasionally she would offer, though it clearly came from a sense of obligation. Jake wanted her to touch him out of desire, not guilt. At least he wasn’t embarrassed about being erect around her anymore. Sometimes he got that “blue balls” ache, but not often. After she left every evening, he didn’t even feel the need to masturbate anymore. He just missed her and tried to get to sleep quickly so the morning would bring her back.Jake hated hiding his true feelings from her, but he feared ruining what they had. Maybe someday he would have to confront that. He wasn’t ready.The Saturday of changes.It had been a tiring Saturday, but fun. Hiking in the nearby foothills, taking countless photos, and talking about all kinds of things. She seemed so fond of him as they explored and laughed together, he could almost believe she loved him as much as he loved her. He hoped so, at least. Lost in his thoughts, he realized Anna was talking to him as she drove them home.“It’s funny,” Anna said. “I was talking with my mom the other day and she was acting all confused about us. Apparently, I talk about you all the time and she thinks we’re actually dating. 'Mom!’ I said, 'Jake doesn’t think of me that way. We’re just good friends.’ I don’t know why she won’t let this go.”Jake felt his ears burning. HE doesn’t feel about HER that way? Feeling exhausted from the hike, he was unable to slow the emotion building in his heart.“That’s bullshit,” he said, more anger in his voice than he intended. He stared out the front window.Anna glanced at him with surprise. Jake didn’t turn toward her. He knew Anna wasn’t a malicious person, and he knew he was probably messing up everything, but it hurt.“What do you mean?” Anna asked quietly.Jake knew his anger was out of control, but he spoke anyway. “You always assume too much. Mostly I don’t mind, but you don’t get to make assumptions about my feelings, to lie to my face. It couldn’t be more obvious how I feel about you, how I’ve felt about you from the very start. I don’t expect you to love me back. You don’t owe me anything. But it would be really fucking decent of you to at least be honest that YOU set the rules. You don’t get to put words in my mouth.”Anna didn’t respond. Jake stared straight ahead. He heard some sniffling and saw her wiping her eyes. He wanted to comfort her. He hated to see her in pain, no matter the reason. But his angry heart felt better, even if he dreaded to think what he had done to their friendship.The rest of the drive home was silent. They went to their separate apartments that evening. Jake showered by himself for the first time in weeks feeling lonely and sad. Fearing he had made the biggest mistake of his life, he made it as far as the couch before breaking down in tears and crying himself to sleep beneath the throw blanket.Sometime later, Jake heard Anna’s voice. Was it a dream? His head felt heavy with sleep. In the darkness, Anna was pulling his hand.“Come on, sleepy-head, you’ll be more comfortable in bed,” she said.Her voice held no anger, only kindness. It must be a dream. He found himself in his bed. Anna climbed in beside him, her warm back snuggled up against him as she pulled his arm around her. He longed for it to be real, though he knew it couldn’t be. Anna hated him now. It was over. Jake’s mind drifted into blank despair again.Anna was smiling at him. Her face was the most beautiful thing in the world and her gaze felt like being bathed in warm sunshine. She leaned in to kiss him. In the dream logic, this wasn’t a surprise. She loved him as he loved her, and kissing him was the most natural thing in the world. Her lips touched his and he felt his heart grow and expand until it consumed the universe with their love and joy. All they needed was each other, forever. Touching her face, he was the happiest man in the world. He called out her name.“Jake,” he heard Anna’s voice, gentle and tender. “Jake, are you okay?” He felt a warm hand on his cheek.He opened his eyes and saw the light of dawn, soft on Anna’s face. What was she doing here? Genuine concern was in her eyes.“Jake, you were having a dream. Are you okay?”As he woke up more, he realized his dick felt strange. Moving his hand, he found it was on Anna’s hip, and her hip was wet. The sheets were wet. His crotch was wet. With horror he realized it had been a wet dream. The biggest, messiest wet dream of his life. And it was all over Anna.His body involuntarily jerked in panic. Tears erupted from his eyes and he started gasping, unable to speak even if he knew what to say. What was she even doing here? He couldn’t see clearly through the tears, but he had no trouble imagining the hateful look she must be giving him.“Sorry!” he blurted. “Oh god, I’m so sorry.” He started to pull back, to climb out of the bed and away from the mess, away from everything. But she gently pulled him back down beside her.“Shhhh, don’t talk,” she said. “Just look into my eyes and breathe.”Jake squeezed his eyes shut, too ashamed to look at her.“Everything’s okay, Jake,” Anna continued. “I’m here with you, and everything is okay.”Jake opened his mouth to apologize again but she put a finger over his lips before he could speak.“There’s nothing to say. Just breathe with me.”He opened his eyes and through the tears saw Anna’s kind eyes looking into his. He inhaled, and his chest jerked with a suppressed sob.“Everything’s okay, Jake. Just breathe with me.”Jake took another breath, and he managed to make it a bit smoother. Anna smiled and stroked his temple. He focused on the warmth of her hand on his face and tried to forget the shameful wet mess between them on the sheets.Eventually his breathing calmed down. Anna used her thumb to wipe the tears off his cheeks, and she smiled at him.“Now we’re going to do something silly,” Anna said, “And you’re not going to argue with me. You’re going to come with me to the shower, but first you’re going to close your eyes. Do you trust me?”Jake was puzzled but he nodded and closed his eyes. He felt her pull the cold sticky sheet off them, and then she helped him stand up. Holding him from the side, she slowly guided him, and he realized she was doing this so he wouldn’t look at the mess on the bed. He felt the shame lurch back into his heart, but at that very instant she put her hand on his chest, right over his heart, and he calmed back down.He kept his eyes closed as his feet touched the cold tile of the bathroom. He heard Anna start the shower, and then she pulled them together into the hot water. She pressed the front of her body against the front of his and squeezed him close, her head on his shoulder with her face against his neck. Her breasts were soft and comforting. Her hips pushed against his and he felt his shrunken, ashamed dick press against her thighs. He put his arms around her and returned the hug. The hot water poured over them both and he felt his body relaxing.For a few minutes they just held each other. Anna adjusted the water slightly hotter. The air filled with steam and their bodies seemed to blend as the water coursed over their shoulders. Anna sighed happily against his neck. She didn’t hate him for ejaculating on her in his sleep. She wasn’t repelled. She didn’t find him revolting. Anna squeezed him tighter, then pulled back from her hug.“You can open your eyes now.” She was smiling at him. She put her finger to his lips and then grabbed the shampoo bottle. Her fingers massaged the shampoo into his scalp and his eyes rolled back in pleasure. She rubbed far longer than was needed to wash his hair, clearly enjoying his reaction. With a soapy wash cloth, she rubbed his shoulders. Her thumbs worked into his muscles as she washed down his back, down each arm, across his chest and down his belly.Without hesitation she gently held his shrunken dick and stroked it carefully with the wash cloth. It wasn’t sexual as she cleaned him, it was simply loving. She washed his bottom, his legs, and his feet, including scrubbing between each toe.She pushed him back into the hot water to rinse and held a finger up to tell him to stay there. Then she carefully shampooed her own hair, and washed her own body, making sure he was watching. Finally, she joined him in the hot stream of water and hugged him as she rinsed.When Anna turned the water off she grabbed a fresh towel and dried him carefully over his whole body before drying herself while he watched. He laughed when she used the hair dryer on him, blowing warm air all over their bodies until they were fully dry before she got a brush and started drying his hair too. She had fun styling his hair to look ridiculous, and then quickly dried her own hair too.Anna wrapped them each in bath robes to stay warm, and walked him to the kitchen. She put him in a chair and he watched while she made coffee, toast, and eggs. She sat beside him while they ate in silence, watching each other and giggling now and then.When they finished eating, she held up her finger again to tell him to stay in his chair, and then went off to the bedroom. Anna was gone only a few minutes before returning and leading him by the hand back to the bed, which now had fresh sheets. She sat beside him on the bed and smiled at him.“How are you feeling now?” Anna asked. “Better?”Jake smiled. He was clean, warm, and fed. Also, he realized, he was loved. “All better. One hundred percent better. One thousand percent better!”Anna giggled. She couldn’t seem to stop smiling.“Remember when I first asked if I could show you my breasts?”

Her Inverted Intimacy Challenge: Part 4

Play Episode Listen Later Mar 3, 2026

Anna almost loses Jake, then beds him.By darrenr - Listen to the ► Podcast at Steamy Stories.Wordlessly they lay there, Anna clutching his hand as he held her. Eventually her breathing returned to normal, and her grip softened. Jake realized he had his dick pressed against her bottom in their hug, but it had softened during the past few minutes. He felt proud of himself and his soft dick. Anna was the epitome of his sexual desires, but in this moment even his perpetually rude cock recognized this was not the time to make selfish demands. It felt nice snuggled up against her soft bottom.His face resting on Anna's back, he couldn't help smiling. He had done it! He had most definitely given her something she'd never felt before.A small movement from Anna brought him out of his reverie, and he realized she was crying. In a single second his heart fell from impossible heights of blissful pride and satisfaction down into despair.“Anna, are you okay?” Jake asked, his voice small. “Did I hurt you?” For what felt like an eternity, there was no response at all. Then Anna's grip on his hand tightened, and she pulled it against her chest.“Thank you,” she said, her voice cracking. Holding his hand tight, she moved to sit up and he pulled back to give her space. She looked at him with cheeks wet with tears. “I have no idea why I'm crying. No, you didn't hurt me. You made me feel more pleasure than I ever thought possible. I don't know where all this emotion is coming from.” She leaned her head against his shoulder, and he put his free arm around her again. They sat in silence for a few minutes more. Jake's heart gradually recovered from its moment of terror, and he breathed easy again, the sweet scent of her hair in his nose.With a deep breath Anna lifted her head and looked at Jake. Still feeling elated from his success, he started to grin. This in turn made Anna smile.Making a goofy face, he said, “Well?”They both burst out laughing. Jake felt elated at what he had accomplished, giddy with delight at what they had shared, at how close he felt to Anna.When the laughter died down, Anna's face grew thoughtful. “What I just experienced, was that normal? Is that what everyone feels when they orgasm? Is that what you feel?”“I doubt I've ever experienced anything even a tenth as good as that,” Jake said. “That seemed to be in the earth-shattering category.“It really was. My legs feel weak. I can't get over how good that felt. I honestly didn't know anything like that was possible. How did you know how to do that?”He thought about all the ‘how to' videos about sex he had watched, all the guides to please a woman he had read, how he poured all his love and focus into doing the best he could for her. “I think I just got lucky.”Anna laughed. “No, I'm the one who got lucky.” She sat in silence for another moment looking at her toes.“Jake?”“Yes?”“You kissed my pussy.” It still caught him off guard when she used that word, but he liked it.“Yes. I hope you don't mind. I knew you needed more and that was my only idea,” Jake said.“Was it, was it gross?” Anna asked.“Quite the opposite,” Jake said. Of course, the truth was he was overflowing with affection for her. Confessing all that now seemed too much. He kept silent.“Anna,” Jake said quietly, “Did I hurt you?”“What on earth are you talking about?” she said.“You know, when I, when I put my finger inside.”“Oh!” she giggled. “No, it didn't hurt at all. Quite the opposite. Completely different from the doctor.”“Oh good,” Jake said, his finger remembering. Warm, snug, delicate. He felt his arousal start to grow and tried to think about something else instead.After a few minutes, Anna asked, “How tired are you?”“Oh, I'm fine.”“But it took me ages to reach the climax. You must have been getting a little tired?”“A little,” Jake admitted. “But I'm fine now.”“All recovered?”“Yes, all recovered!” Jake said, laughing at the interrogation.“Good!” Anna said, distractedly stroking the top of her thigh. “Good, I'm glad. That was an incredible thing you did for me, just an incredible thing.”“Anna, please,” Jake protested, turning his head to meet her eyes. “I enjoyed it too, you know.”Anna smiled but quickly looked away in embarrassment. “Of course, now, now it's your turn.” Anna was clearly getting nervous. “I owe you some–”“No,” Jake said a little too firmly, sitting up. “No, listen. There's nothing owed. Nothing transactional here. If some day in the future you find yourself needing to touch me, truly deeply needing it, then nothing would be more welcome. Nothing. But I've been slapping this salami and having orgasms for years. I'm fine. What's important now is you've taken a huge risk with this first step, and it was a good experience. I think you should load up on good experiences before taking more risks.”“'Good experience' rather understates things,” Anna said with a laugh.“Here's what I think,” Jake said. “No offense, but you look a bit worn out. How about I get us a snack and we watch a movie to relax?”Anna smiled. “I do feel a bit drained. That would be nice.”Jake returned with some apple slices, cheese, and crackers. Anna cued up a movie and he realized he was feeling pretty drained himself.Sometime later he awoke to find Anna still sitting with him. The movie was over. It took him a moment to notice she was looking down at his crotch.Jake must have moved a little because Anna startled, looked away, and began to get up.“What's the matter?” he asked.“Sorry, I shouldn't have been staring while you were asleep.”Jake laughed. “Are you joking? We've been naked with each other for weeks now. Why would I mind if you looked at my ugly wiener?”“I don't know,” Anna said, settling back down on the couch beside him and leaning against him. “It just felt like peeping or something.” She smiled. “I guess I was being silly.” Jake nodded and put his arm around her again, feeling her shoulders rise and fall as she breathed, enjoying how her breasts moved.“I don't think it's ugly,” Anna said after a few minutes.“Huh?”“Your penis. Your cock,” she added with a smile. “I don't think it's ugly. It got super small while you slept. I thought it was cute.”Jake felt the topic of discussion begin to swell. He whispered, “Uh oh, it knows you're talking about it.”Anna bent down close to his dick and whispered to it, “I think you're cute when you're all shrunk up small!” Then she sat back up, giggling.His dick jumped a little in response, and Anna laughed more.“Can I tell you something stupid?” Anna asked.“Of course.”“This is embarrassing, but, when your cock gets really big…” Anna looked down. In a quiet voice, she said, “I feel a little bit scared of it.”Jake immediately began to shrink. He frightened her? He moved to cover himself with his hands.“No wait,” Anna said, grabbing his arm and pulling him back down. “That's not what I meant. You didn't do anything wrong.” She pulled his hands up so his crotch was exposed again. “All I meant was it's intimidating when it gets big.”Jake thought for a moment. “I have to be honest. It's hard to not be aroused when I'm with you. But I will try!”“No,” Anna said. “No, I don't want that. This doesn't make sense, but I also like when it gets big. I feel both excited and a little afraid.” She looked down and then back into his eyes. “I guess what I mean is I appreciate how patient you're being with me. I intend to return the generosity you've shown me, but, but I'm just not ready yet.”Jake let out the breath he didn't realize he was holding. “Oh, well that's no problem. I thought we already settled this? You don’t ‘owe’ me anything.“"I know,” Anna said, “I just–”“Listen,” Jake interrupted. “Believe me. I’m having a… profoundly good time. All I can think about is hoping you’ll invite me back for another round.”“What does your schedule look like tomorrow evening?” she asked.Jake chuckled, and he felt his dick jump at the thought. “I think I can fit you in,” he said.Anna smiled, and leaned her head against his shoulder again.Unexpressed Desires.Anna didn’t like to directly ask for Jake to work his magic on her. Her face would occasionally get this hungry look that was extremely obvious, and Jake made sure to offer. As he practiced on her more and more, he became immensely proud of his growing expertise. He had learned to read her feelings, her body’s reactions, and her needs. Sometimes it was clear she needed immediate relief, and he would give it to her. Other times, his favorite times, she enjoyed dragging it out. He would bring her right to the edge, and then back away, teasing her over and over until she couldn’t stand it even one more second. When she reached that point, he would take her over the edge into an incredibly powerful orgasm that left both of them exhausted afterwards.She wasn’t ready to return the attention. Occasionally she would offer, though it clearly came from a sense of obligation. Jake wanted her to touch him out of desire, not guilt. At least he wasn’t embarrassed about being erect around her anymore. Sometimes he got that “blue balls” ache, but not often. After she left every evening, he didn’t even feel the need to masturbate anymore. He just missed her and tried to get to sleep quickly so the morning would bring her back.Jake hated hiding his true feelings from her, but he feared ruining what they had. Maybe someday he would have to confront that. He wasn’t ready.The Saturday of changes.It had been a tiring Saturday, but fun. Hiking in the nearby foothills, taking countless photos, and talking about all kinds of things. She seemed so fond of him as they explored and laughed together, he could almost believe she loved him as much as he loved her. He hoped so, at least. Lost in his thoughts, he realized Anna was talking to him as she drove them home.“It’s funny,” Anna said. “I was talking with my mom the other day and she was acting all confused about us. Apparently, I talk about you all the time and she thinks we’re actually dating. 'Mom!’ I said, 'Jake doesn’t think of me that way. We’re just good friends.’ I don’t know why she won’t let this go.”Jake felt his ears burning. HE doesn’t feel about HER that way? Feeling exhausted from the hike, he was unable to slow the emotion building in his heart.“That’s bullshit,” he said, more anger in his voice than he intended. He stared out the front window.Anna glanced at him with surprise. Jake didn’t turn toward her. He knew Anna wasn’t a malicious person, and he knew he was probably messing up everything, but it hurt.“What do you mean?” Anna asked quietly.Jake knew his anger was out of control, but he spoke anyway. “You always assume too much. Mostly I don’t mind, but you don’t get to make assumptions about my feelings, to lie to my face. It couldn’t be more obvious how I feel about you, how I’ve felt about you from the very start. I don’t expect you to love me back. You don’t owe me anything. But it would be really fucking decent of you to at least be honest that YOU set the rules. You don’t get to put words in my mouth.”Anna didn’t respond. Jake stared straight ahead. He heard some sniffling and saw her wiping her eyes. He wanted to comfort her. He hated to see her in pain, no matter the reason. But his angry heart felt better, even if he dreaded to think what he had done to their friendship.The rest of the drive home was silent. They went to their separate apartments that evening. Jake showered by himself for the first time in weeks feeling lonely and sad. Fearing he had made the biggest mistake of his life, he made it as far as the couch before breaking down in tears and crying himself to sleep beneath the throw blanket.Sometime later, Jake heard Anna’s voice. Was it a dream? His head felt heavy with sleep. In the darkness, Anna was pulling his hand.“Come on, sleepy-head, you’ll be more comfortable in bed,” she said.Her voice held no anger, only kindness. It must be a dream. He found himself in his bed. Anna climbed in beside him, her warm back snuggled up against him as she pulled his arm around her. He longed for it to be real, though he knew it couldn’t be. Anna hated him now. It was over. Jake’s mind drifted into blank despair again.Anna was smiling at him. Her face was the most beautiful thing in the world and her gaze felt like being bathed in warm sunshine. She leaned in to kiss him. In the dream logic, this wasn’t a surprise. She loved him as he loved her, and kissing him was the most natural thing in the world. Her lips touched his and he felt his heart grow and expand until it consumed the universe with their love and joy. All they needed was each other, forever. Touching her face, he was the happiest man in the world. He called out her name.“Jake,” he heard Anna’s voice, gentle and tender. “Jake, are you okay?” He felt a warm hand on his cheek.He opened his eyes and saw the light of dawn, soft on Anna’s face. What was she doing here? Genuine concern was in her eyes.“Jake, you were having a dream. Are you okay?”As he woke up more, he realized his dick felt strange. Moving his hand, he found it was on Anna’s hip, and her hip was wet. The sheets were wet. His crotch was wet. With horror he realized it had been a wet dream. The biggest, messiest wet dream of his life. And it was all over Anna.His body involuntarily jerked in panic. Tears erupted from his eyes and he started gasping, unable to speak even if he knew what to say. What was she even doing here? He couldn’t see clearly through the tears, but he had no trouble imagining the hateful look she must be giving him.“Sorry!” he blurted. “Oh god, I’m so sorry.” He started to pull back, to climb out of the bed and away from the mess, away from everything. But she gently pulled him back down beside her.“Shhhh, don’t talk,” she said. “Just look into my eyes and breathe.”Jake squeezed his eyes shut, too ashamed to look at her.“Everything’s okay, Jake,” Anna continued. “I’m here with you, and everything is okay.”Jake opened his mouth to apologize again but she put a finger over his lips before he could speak.“There’s nothing to say. Just breathe with me.”He opened his eyes and through the tears saw Anna’s kind eyes looking into his. He inhaled, and his chest jerked with a suppressed sob.“Everything’s okay, Jake. Just breathe with me.”Jake took another breath, and he managed to make it a bit smoother. Anna smiled and stroked his temple. He focused on the warmth of her hand on his face and tried to forget the shameful wet mess between them on the sheets.Eventually his breathing calmed down. Anna used her thumb to wipe the tears off his cheeks, and she smiled at him.“Now we’re going to do something silly,” Anna said, “And you’re not going to argue with me. You’re going to come with me to the shower, but first you’re going to close your eyes. Do you trust me?”Jake was puzzled but he nodded and closed his eyes. He felt her pull the cold sticky sheet off them, and then she helped him stand up. Holding him from the side, she slowly guided him, and he realized she was doing this so he wouldn’t look at the mess on the bed. He felt the shame lurch back into his heart, but at that very instant she put her hand on his chest, right over his heart, and he calmed back down.He kept his eyes closed as his feet touched the cold tile of the bathroom. He heard Anna start the shower, and then she pulled them together into the hot water. She pressed the front of her body against the front of his and squeezed him close, her head on his shoulder with her face against his neck. Her breasts were soft and comforting. Her hips pushed against his and he felt his shrunken, ashamed dick press against her thighs. He put his arms around her and returned the hug. The hot water poured over them both and he felt his body relaxing.For a few minutes they just held each other. Anna adjusted the water slightly hotter. The air filled with steam and their bodies seemed to blend as the water coursed over their shoulders. Anna sighed happily against his neck. She didn’t hate him for ejaculating on her in his sleep. She wasn’t repelled. She didn’t find him revolting. Anna squeezed him tighter, then pulled back from her hug.“You can open your eyes now.” She was smiling at him. She put her finger to his lips and then grabbed the shampoo bottle. Her fingers massaged the shampoo into his scalp and his eyes rolled back in pleasure. She rubbed far longer than was needed to wash his hair, clearly enjoying his reaction. With a soapy wash cloth, she rubbed his shoulders. Her thumbs worked into his muscles as she washed down his back, down each arm, across his chest and down his belly.Without hesitation she gently held his shrunken dick and stroked it carefully with the wash cloth. It wasn’t sexual as she cleaned him, it was simply loving. She washed his bottom, his legs, and his feet, including scrubbing between each toe.She pushed him back into the hot water to rinse and held a finger up to tell him to stay there. Then she carefully shampooed her own hair, and washed her own body, making sure he was watching. Finally, she joined him in the hot stream of water and hugged him as she rinsed.When Anna turned the water off she grabbed a fresh towel and dried him carefully over his whole body before drying herself while he watched. He laughed when she used the hair dryer on him, blowing warm air all over their bodies until they were fully dry before she got a brush and started drying his hair too. She had fun styling his hair to look ridiculous, and then quickly dried her own hair too.Anna wrapped them each in bath robes to stay warm, and walked him to the kitchen. She put him in a chair and he watched while she made coffee, toast, and eggs. She sat beside him while they ate in silence, watching each other and giggling now and then.When they finished eating, she held up her finger again to tell him to stay in his chair, and then went off to the bedroom. Anna was gone only a few minutes before returning and leading him by the hand back to the bed, which now had fresh sheets. She sat beside him on the bed and smiled at him.“How are you feeling now?” Anna asked. “Better?”Jake smiled. He was clean, warm, and fed. Also, he realized, he was loved. “All better. One hundred percent better. One thousand percent better!”Anna giggled. She couldn’t seem to stop smiling.“Remember when I first asked if I could show you my breasts?”

Her Inverted Intimacy Challenge: Part 4

Play Episode Listen Later Mar 3, 2026

Anna almost loses Jake, then beds him.By darrenr - Listen to the ► Podcast at Steamy Stories.Wordlessly they lay there, Anna clutching his hand as he held her. Eventually her breathing returned to normal, and her grip softened. Jake realized he had his dick pressed against her bottom in their hug, but it had softened during the past few minutes. He felt proud of himself and his soft dick. Anna was the epitome of his sexual desires, but in this moment even his perpetually rude cock recognized this was not the time to make selfish demands. It felt nice snuggled up against her soft bottom.His face resting on Anna's back, he couldn't help smiling. He had done it! He had most definitely given her something she'd never felt before.A small movement from Anna brought him out of his reverie, and he realized she was crying. In a single second his heart fell from impossible heights of blissful pride and satisfaction down into despair.“Anna, are you okay?” Jake asked, his voice small. “Did I hurt you?” For what felt like an eternity, there was no response at all. Then Anna's grip on his hand tightened, and she pulled it against her chest.“Thank you,” she said, her voice cracking. Holding his hand tight, she moved to sit up and he pulled back to give her space. She looked at him with cheeks wet with tears. “I have no idea why I'm crying. No, you didn't hurt me. You made me feel more pleasure than I ever thought possible. I don't know where all this emotion is coming from.” She leaned her head against his shoulder, and he put his free arm around her again. They sat in silence for a few minutes more. Jake's heart gradually recovered from its moment of terror, and he breathed easy again, the sweet scent of her hair in his nose.With a deep breath Anna lifted her head and looked at Jake. Still feeling elated from his success, he started to grin. This in turn made Anna smile.Making a goofy face, he said, “Well?”They both burst out laughing. Jake felt elated at what he had accomplished, giddy with delight at what they had shared, at how close he felt to Anna.When the laughter died down, Anna's face grew thoughtful. “What I just experienced, was that normal? Is that what everyone feels when they orgasm? Is that what you feel?”“I doubt I've ever experienced anything even a tenth as good as that,” Jake said. “That seemed to be in the earth-shattering category.“It really was. My legs feel weak. I can't get over how good that felt. I honestly didn't know anything like that was possible. How did you know how to do that?”He thought about all the ‘how to' videos about sex he had watched, all the guides to please a woman he had read, how he poured all his love and focus into doing the best he could for her. “I think I just got lucky.”Anna laughed. “No, I'm the one who got lucky.” She sat in silence for another moment looking at her toes.“Jake?”“Yes?”“You kissed my pussy.” It still caught him off guard when she used that word, but he liked it.“Yes. I hope you don't mind. I knew you needed more and that was my only idea,” Jake said.“Was it, was it gross?” Anna asked.“Quite the opposite,” Jake said. Of course, the truth was he was overflowing with affection for her. Confessing all that now seemed too much. He kept silent.“Anna,” Jake said quietly, “Did I hurt you?”“What on earth are you talking about?” she said.“You know, when I, when I put my finger inside.”“Oh!” she giggled. “No, it didn't hurt at all. Quite the opposite. Completely different from the doctor.”“Oh good,” Jake said, his finger remembering. Warm, snug, delicate. He felt his arousal start to grow and tried to think about something else instead.After a few minutes, Anna asked, “How tired are you?”“Oh, I'm fine.”“But it took me ages to reach the climax. You must have been getting a little tired?”“A little,” Jake admitted. “But I'm fine now.”“All recovered?”“Yes, all recovered!” Jake said, laughing at the interrogation.“Good!” Anna said, distractedly stroking the top of her thigh. “Good, I'm glad. That was an incredible thing you did for me, just an incredible thing.”“Anna, please,” Jake protested, turning his head to meet her eyes. “I enjoyed it too, you know.”Anna smiled but quickly looked away in embarrassment. “Of course, now, now it's your turn.” Anna was clearly getting nervous. “I owe you some–”“No,” Jake said a little too firmly, sitting up. “No, listen. There's nothing owed. Nothing transactional here. If some day in the future you find yourself needing to touch me, truly deeply needing it, then nothing would be more welcome. Nothing. But I've been slapping this salami and having orgasms for years. I'm fine. What's important now is you've taken a huge risk with this first step, and it was a good experience. I think you should load up on good experiences before taking more risks.”“'Good experience' rather understates things,” Anna said with a laugh.“Here's what I think,” Jake said. “No offense, but you look a bit worn out. How about I get us a snack and we watch a movie to relax?”Anna smiled. “I do feel a bit drained. That would be nice.”Jake returned with some apple slices, cheese, and crackers. Anna cued up a movie and he realized he was feeling pretty drained himself.Sometime later he awoke to find Anna still sitting with him. The movie was over. It took him a moment to notice she was looking down at his crotch.Jake must have moved a little because Anna startled, looked away, and began to get up.“What's the matter?” he asked.“Sorry, I shouldn't have been staring while you were asleep.”Jake laughed. “Are you joking? We've been naked with each other for weeks now. Why would I mind if you looked at my ugly wiener?”“I don't know,” Anna said, settling back down on the couch beside him and leaning against him. “It just felt like peeping or something.” She smiled. “I guess I was being silly.” Jake nodded and put his arm around her again, feeling her shoulders rise and fall as she breathed, enjoying how her breasts moved.“I don't think it's ugly,” Anna said after a few minutes.“Huh?”“Your penis. Your cock,” she added with a smile. “I don't think it's ugly. It got super small while you slept. I thought it was cute.”Jake felt the topic of discussion begin to swell. He whispered, “Uh oh, it knows you're talking about it.”Anna bent down close to his dick and whispered to it, “I think you're cute when you're all shrunk up small!” Then she sat back up, giggling.His dick jumped a little in response, and Anna laughed more.“Can I tell you something stupid?” Anna asked.“Of course.”“This is embarrassing, but, when your cock gets really big…” Anna looked down. In a quiet voice, she said, “I feel a little bit scared of it.”Jake immediately began to shrink. He frightened her? He moved to cover himself with his hands.“No wait,” Anna said, grabbing his arm and pulling him back down. “That's not what I meant. You didn't do anything wrong.” She pulled his hands up so his crotch was exposed again. “All I meant was it's intimidating when it gets big.”Jake thought for a moment. “I have to be honest. It's hard to not be aroused when I'm with you. But I will try!”“No,” Anna said. “No, I don't want that. This doesn't make sense, but I also like when it gets big. I feel both excited and a little afraid.” She looked down and then back into his eyes. “I guess what I mean is I appreciate how patient you're being with me. I intend to return the generosity you've shown me, but, but I'm just not ready yet.”Jake let out the breath he didn't realize he was holding. “Oh, well that's no problem. I thought we already settled this? You don’t ‘owe’ me anything.“"I know,” Anna said, “I just–”“Listen,” Jake interrupted. “Believe me. I’m having a… profoundly good time. All I can think about is hoping you’ll invite me back for another round.”“What does your schedule look like tomorrow evening?” she asked.Jake chuckled, and he felt his dick jump at the thought. “I think I can fit you in,” he said.Anna smiled, and leaned her head against his shoulder again.Unexpressed Desires.Anna didn’t like to directly ask for Jake to work his magic on her. Her face would occasionally get this hungry look that was extremely obvious, and Jake made sure to offer. As he practiced on her more and more, he became immensely proud of his growing expertise. He had learned to read her feelings, her body’s reactions, and her needs. Sometimes it was clear she needed immediate relief, and he would give it to her. Other times, his favorite times, she enjoyed dragging it out. He would bring her right to the edge, and then back away, teasing her over and over until she couldn’t stand it even one more second. When she reached that point, he would take her over the edge into an incredibly powerful orgasm that left both of them exhausted afterwards.She wasn’t ready to return the attention. Occasionally she would offer, though it clearly came from a sense of obligation. Jake wanted her to touch him out of desire, not guilt. At least he wasn’t embarrassed about being erect around her anymore. Sometimes he got that “blue balls” ache, but not often. After she left every evening, he didn’t even feel the need to masturbate anymore. He just missed her and tried to get to sleep quickly so the morning would bring her back.Jake hated hiding his true feelings from her, but he feared ruining what they had. Maybe someday he would have to confront that. He wasn’t ready.The Saturday of changes.It had been a tiring Saturday, but fun. Hiking in the nearby foothills, taking countless photos, and talking about all kinds of things. She seemed so fond of him as they explored and laughed together, he could almost believe she loved him as much as he loved her. He hoped so, at least. Lost in his thoughts, he realized Anna was talking to him as she drove them home.“It’s funny,” Anna said. “I was talking with my mom the other day and she was acting all confused about us. Apparently, I talk about you all the time and she thinks we’re actually dating. 'Mom!’ I said, 'Jake doesn’t think of me that way. We’re just good friends.’ I don’t know why she won’t let this go.”Jake felt his ears burning. HE doesn’t feel about HER that way? Feeling exhausted from the hike, he was unable to slow the emotion building in his heart.“That’s bullshit,” he said, more anger in his voice than he intended. He stared out the front window.Anna glanced at him with surprise. Jake didn’t turn toward her. He knew Anna wasn’t a malicious person, and he knew he was probably messing up everything, but it hurt.“What do you mean?” Anna asked quietly.Jake knew his anger was out of control, but he spoke anyway. “You always assume too much. Mostly I don’t mind, but you don’t get to make assumptions about my feelings, to lie to my face. It couldn’t be more obvious how I feel about you, how I’ve felt about you from the very start. I don’t expect you to love me back. You don’t owe me anything. But it would be really fucking decent of you to at least be honest that YOU set the rules. You don’t get to put words in my mouth.”Anna didn’t respond. Jake stared straight ahead. He heard some sniffling and saw her wiping her eyes. He wanted to comfort her. He hated to see her in pain, no matter the reason. But his angry heart felt better, even if he dreaded to think what he had done to their friendship.The rest of the drive home was silent. They went to their separate apartments that evening. Jake showered by himself for the first time in weeks feeling lonely and sad. Fearing he had made the biggest mistake of his life, he made it as far as the couch before breaking down in tears and crying himself to sleep beneath the throw blanket.Sometime later, Jake heard Anna’s voice. Was it a dream? His head felt heavy with sleep. In the darkness, Anna was pulling his hand.“Come on, sleepy-head, you’ll be more comfortable in bed,” she said.Her voice held no anger, only kindness. It must be a dream. He found himself in his bed. Anna climbed in beside him, her warm back snuggled up against him as she pulled his arm around her. He longed for it to be real, though he knew it couldn’t be. Anna hated him now. It was over. Jake’s mind drifted into blank despair again.Anna was smiling at him. Her face was the most beautiful thing in the world and her gaze felt like being bathed in warm sunshine. She leaned in to kiss him. In the dream logic, this wasn’t a surprise. She loved him as he loved her, and kissing him was the most natural thing in the world. Her lips touched his and he felt his heart grow and expand until it consumed the universe with their love and joy. All they needed was each other, forever. Touching her face, he was the happiest man in the world. He called out her name.“Jake,” he heard Anna’s voice, gentle and tender. “Jake, are you okay?” He felt a warm hand on his cheek.He opened his eyes and saw the light of dawn, soft on Anna’s face. What was she doing here? Genuine concern was in her eyes.“Jake, you were having a dream. Are you okay?”As he woke up more, he realized his dick felt strange. Moving his hand, he found it was on Anna’s hip, and her hip was wet. The sheets were wet. His crotch was wet. With horror he realized it had been a wet dream. The biggest, messiest wet dream of his life. And it was all over Anna.His body involuntarily jerked in panic. Tears erupted from his eyes and he started gasping, unable to speak even if he knew what to say. What was she even doing here? He couldn’t see clearly through the tears, but he had no trouble imagining the hateful look she must be giving him.“Sorry!” he blurted. “Oh god, I’m so sorry.” He started to pull back, to climb out of the bed and away from the mess, away from everything. But she gently pulled him back down beside her.“Shhhh, don’t talk,” she said. “Just look into my eyes and breathe.”Jake squeezed his eyes shut, too ashamed to look at her.“Everything’s okay, Jake,” Anna continued. “I’m here with you, and everything is okay.”Jake opened his mouth to apologize again but she put a finger over his lips before he could speak.“There’s nothing to say. Just breathe with me.”He opened his eyes and through the tears saw Anna’s kind eyes looking into his. He inhaled, and his chest jerked with a suppressed sob.“Everything’s okay, Jake. Just breathe with me.”Jake took another breath, and he managed to make it a bit smoother. Anna smiled and stroked his temple. He focused on the warmth of her hand on his face and tried to forget the shameful wet mess between them on the sheets.Eventually his breathing calmed down. Anna used her thumb to wipe the tears off his cheeks, and she smiled at him.“Now we’re going to do something silly,” Anna said, “And you’re not going to argue with me. You’re going to come with me to the shower, but first you’re going to close your eyes. Do you trust me?”Jake was puzzled but he nodded and closed his eyes. He felt her pull the cold sticky sheet off them, and then she helped him stand up. Holding him from the side, she slowly guided him, and he realized she was doing this so he wouldn’t look at the mess on the bed. He felt the shame lurch back into his heart, but at that very instant she put her hand on his chest, right over his heart, and he calmed back down.He kept his eyes closed as his feet touched the cold tile of the bathroom. He heard Anna start the shower, and then she pulled them together into the hot water. She pressed the front of her body against the front of his and squeezed him close, her head on his shoulder with her face against his neck. Her breasts were soft and comforting. Her hips pushed against his and he felt his shrunken, ashamed dick press against her thighs. He put his arms around her and returned the hug. The hot water poured over them both and he felt his body relaxing.For a few minutes they just held each other. Anna adjusted the water slightly hotter. The air filled with steam and their bodies seemed to blend as the water coursed over their shoulders. Anna sighed happily against his neck. She didn’t hate him for ejaculating on her in his sleep. She wasn’t repelled. She didn’t find him revolting. Anna squeezed him tighter, then pulled back from her hug.“You can open your eyes now.” She was smiling at him. She put her finger to his lips and then grabbed the shampoo bottle. Her fingers massaged the shampoo into his scalp and his eyes rolled back in pleasure. She rubbed far longer than was needed to wash his hair, clearly enjoying his reaction. With a soapy wash cloth, she rubbed his shoulders. Her thumbs worked into his muscles as she washed down his back, down each arm, across his chest and down his belly.Without hesitation she gently held his shrunken dick and stroked it carefully with the wash cloth. It wasn’t sexual as she cleaned him, it was simply loving. She washed his bottom, his legs, and his feet, including scrubbing between each toe.She pushed him back into the hot water to rinse and held a finger up to tell him to stay there. Then she carefully shampooed her own hair, and washed her own body, making sure he was watching. Finally, she joined him in the hot stream of water and hugged him as she rinsed.When Anna turned the water off she grabbed a fresh towel and dried him carefully over his whole body before drying herself while he watched. He laughed when she used the hair dryer on him, blowing warm air all over their bodies until they were fully dry before she got a brush and started drying his hair too. She had fun styling his hair to look ridiculous, and then quickly dried her own hair too.Anna wrapped them each in bath robes to stay warm, and walked him to the kitchen. She put him in a chair and he watched while she made coffee, toast, and eggs. She sat beside him while they ate in silence, watching each other and giggling now and then.When they finished eating, she held up her finger again to tell him to stay in his chair, and then went off to the bedroom. Anna was gone only a few minutes before returning and leading him by the hand back to the bed, which now had fresh sheets. She sat beside him on the bed and smiled at him.“How are you feeling now?” Anna asked. “Better?”Jake smiled. He was clean, warm, and fed. Also, he realized, he was loved. “All better. One hundred percent better. One thousand percent better!”Anna giggled. She couldn’t seem to stop smiling.“Remember when I first asked if I could show you my breasts?”

stories lost moving mom fantasy holding narrative tears intimacy sexuality warm genuine touching hiking explicit novels fearing erotica confessing inverted shhhh

Her Inverted Intimacy Challenge: Part 4

Play Episode Listen Later Mar 3, 2026

Anna almost loses Jake, then beds him.By darrenr - Listen to the ► Podcast at Steamy Stories.Wordlessly they lay there, Anna clutching his hand as he held her. Eventually her breathing returned to normal, and her grip softened. Jake realized he had his dick pressed against her bottom in their hug, but it had softened during the past few minutes. He felt proud of himself and his soft dick. Anna was the epitome of his sexual desires, but in this moment even his perpetually rude cock recognized this was not the time to make selfish demands. It felt nice snuggled up against her soft bottom.His face resting on Anna's back, he couldn't help smiling. He had done it! He had most definitely given her something she'd never felt before.A small movement from Anna brought him out of his reverie, and he realized she was crying. In a single second his heart fell from impossible heights of blissful pride and satisfaction down into despair.“Anna, are you okay?” Jake asked, his voice small. “Did I hurt you?” For what felt like an eternity, there was no response at all. Then Anna's grip on his hand tightened, and she pulled it against her chest.“Thank you,” she said, her voice cracking. Holding his hand tight, she moved to sit up and he pulled back to give her space. She looked at him with cheeks wet with tears. “I have no idea why I'm crying. No, you didn't hurt me. You made me feel more pleasure than I ever thought possible. I don't know where all this emotion is coming from.” She leaned her head against his shoulder, and he put his free arm around her again. They sat in silence for a few minutes more. Jake's heart gradually recovered from its moment of terror, and he breathed easy again, the sweet scent of her hair in his nose.With a deep breath Anna lifted her head and looked at Jake. Still feeling elated from his success, he started to grin. This in turn made Anna smile.Making a goofy face, he said, “Well?”They both burst out laughing. Jake felt elated at what he had accomplished, giddy with delight at what they had shared, at how close he felt to Anna.When the laughter died down, Anna's face grew thoughtful. “What I just experienced, was that normal? Is that what everyone feels when they orgasm? Is that what you feel?”“I doubt I've ever experienced anything even a tenth as good as that,” Jake said. “That seemed to be in the earth-shattering category.“It really was. My legs feel weak. I can't get over how good that felt. I honestly didn't know anything like that was possible. How did you know how to do that?”He thought about all the ‘how to' videos about sex he had watched, all the guides to please a woman he had read, how he poured all his love and focus into doing the best he could for her. “I think I just got lucky.”Anna laughed. “No, I'm the one who got lucky.” She sat in silence for another moment looking at her toes.“Jake?”“Yes?”“You kissed my pussy.” It still caught him off guard when she used that word, but he liked it.“Yes. I hope you don't mind. I knew you needed more and that was my only idea,” Jake said.“Was it, was it gross?” Anna asked.“Quite the opposite,” Jake said. Of course, the truth was he was overflowing with affection for her. Confessing all that now seemed too much. He kept silent.“Anna,” Jake said quietly, “Did I hurt you?”“What on earth are you talking about?” she said.“You know, when I, when I put my finger inside.”“Oh!” she giggled. “No, it didn't hurt at all. Quite the opposite. Completely different from the doctor.”“Oh good,” Jake said, his finger remembering. Warm, snug, delicate. He felt his arousal start to grow and tried to think about something else instead.After a few minutes, Anna asked, “How tired are you?”“Oh, I'm fine.”“But it took me ages to reach the climax. You must have been getting a little tired?”“A little,” Jake admitted. “But I'm fine now.”“All recovered?”“Yes, all recovered!” Jake said, laughing at the interrogation.“Good!” Anna said, distractedly stroking the top of her thigh. “Good, I'm glad. That was an incredible thing you did for me, just an incredible thing.”“Anna, please,” Jake protested, turning his head to meet her eyes. “I enjoyed it too, you know.”Anna smiled but quickly looked away in embarrassment. “Of course, now, now it's your turn.” Anna was clearly getting nervous. “I owe you some–”“No,” Jake said a little too firmly, sitting up. “No, listen. There's nothing owed. Nothing transactional here. If some day in the future you find yourself needing to touch me, truly deeply needing it, then nothing would be more welcome. Nothing. But I've been slapping this salami and having orgasms for years. I'm fine. What's important now is you've taken a huge risk with this first step, and it was a good experience. I think you should load up on good experiences before taking more risks.”“'Good experience' rather understates things,” Anna said with a laugh.“Here's what I think,” Jake said. “No offense, but you look a bit worn out. How about I get us a snack and we watch a movie to relax?”Anna smiled. “I do feel a bit drained. That would be nice.”Jake returned with some apple slices, cheese, and crackers. Anna cued up a movie and he realized he was feeling pretty drained himself.Sometime later he awoke to find Anna still sitting with him. The movie was over. It took him a moment to notice she was looking down at his crotch.Jake must have moved a little because Anna startled, looked away, and began to get up.“What's the matter?” he asked.“Sorry, I shouldn't have been staring while you were asleep.”Jake laughed. “Are you joking? We've been naked with each other for weeks now. Why would I mind if you looked at my ugly wiener?”“I don't know,” Anna said, settling back down on the couch beside him and leaning against him. “It just felt like peeping or something.” She smiled. “I guess I was being silly.” Jake nodded and put his arm around her again, feeling her shoulders rise and fall as she breathed, enjoying how her breasts moved.“I don't think it's ugly,” Anna said after a few minutes.“Huh?”“Your penis. Your cock,” she added with a smile. “I don't think it's ugly. It got super small while you slept. I thought it was cute.”Jake felt the topic of discussion begin to swell. He whispered, “Uh oh, it knows you're talking about it.”Anna bent down close to his dick and whispered to it, “I think you're cute when you're all shrunk up small!” Then she sat back up, giggling.His dick jumped a little in response, and Anna laughed more.“Can I tell you something stupid?” Anna asked.“Of course.”“This is embarrassing, but, when your cock gets really big…” Anna looked down. In a quiet voice, she said, “I feel a little bit scared of it.”Jake immediately began to shrink. He frightened her? He moved to cover himself with his hands.“No wait,” Anna said, grabbing his arm and pulling him back down. “That's not what I meant. You didn't do anything wrong.” She pulled his hands up so his crotch was exposed again. “All I meant was it's intimidating when it gets big.”Jake thought for a moment. “I have to be honest. It's hard to not be aroused when I'm with you. But I will try!”“No,” Anna said. “No, I don't want that. This doesn't make sense, but I also like when it gets big. I feel both excited and a little afraid.” She looked down and then back into his eyes. “I guess what I mean is I appreciate how patient you're being with me. I intend to return the generosity you've shown me, but, but I'm just not ready yet.”Jake let out the breath he didn't realize he was holding. “Oh, well that's no problem. I thought we already settled this? You don’t ‘owe’ me anything.“"I know,” Anna said, “I just–”“Listen,” Jake interrupted. “Believe me. I’m having a… profoundly good time. All I can think about is hoping you’ll invite me back for another round.”“What does your schedule look like tomorrow evening?” she asked.Jake chuckled, and he felt his dick jump at the thought. “I think I can fit you in,” he said.Anna smiled, and leaned her head against his shoulder again.Unexpressed Desires.Anna didn’t like to directly ask for Jake to work his magic on her. Her face would occasionally get this hungry look that was extremely obvious, and Jake made sure to offer. As he practiced on her more and more, he became immensely proud of his growing expertise. He had learned to read her feelings, her body’s reactions, and her needs. Sometimes it was clear she needed immediate relief, and he would give it to her. Other times, his favorite times, she enjoyed dragging it out. He would bring her right to the edge, and then back away, teasing her over and over until she couldn’t stand it even one more second. When she reached that point, he would take her over the edge into an incredibly powerful orgasm that left both of them exhausted afterwards.She wasn’t ready to return the attention. Occasionally she would offer, though it clearly came from a sense of obligation. Jake wanted her to touch him out of desire, not guilt. At least he wasn’t embarrassed about being erect around her anymore. Sometimes he got that “blue balls” ache, but not often. After she left every evening, he didn’t even feel the need to masturbate anymore. He just missed her and tried to get to sleep quickly so the morning would bring her back.Jake hated hiding his true feelings from her, but he feared ruining what they had. Maybe someday he would have to confront that. He wasn’t ready.The Saturday of changes.It had been a tiring Saturday, but fun. Hiking in the nearby foothills, taking countless photos, and talking about all kinds of things. She seemed so fond of him as they explored and laughed together, he could almost believe she loved him as much as he loved her. He hoped so, at least. Lost in his thoughts, he realized Anna was talking to him as she drove them home.“It’s funny,” Anna said. “I was talking with my mom the other day and she was acting all confused about us. Apparently, I talk about you all the time and she thinks we’re actually dating. 'Mom!’ I said, 'Jake doesn’t think of me that way. We’re just good friends.’ I don’t know why she won’t let this go.”Jake felt his ears burning. HE doesn’t feel about HER that way? Feeling exhausted from the hike, he was unable to slow the emotion building in his heart.“That’s bullshit,” he said, more anger in his voice than he intended. He stared out the front window.Anna glanced at him with surprise. Jake didn’t turn toward her. He knew Anna wasn’t a malicious person, and he knew he was probably messing up everything, but it hurt.“What do you mean?” Anna asked quietly.Jake knew his anger was out of control, but he spoke anyway. “You always assume too much. Mostly I don’t mind, but you don’t get to make assumptions about my feelings, to lie to my face. It couldn’t be more obvious how I feel about you, how I’ve felt about you from the very start. I don’t expect you to love me back. You don’t owe me anything. But it would be really fucking decent of you to at least be honest that YOU set the rules. You don’t get to put words in my mouth.”Anna didn’t respond. Jake stared straight ahead. He heard some sniffling and saw her wiping her eyes. He wanted to comfort her. He hated to see her in pain, no matter the reason. But his angry heart felt better, even if he dreaded to think what he had done to their friendship.The rest of the drive home was silent. They went to their separate apartments that evening. Jake showered by himself for the first time in weeks feeling lonely and sad. Fearing he had made the biggest mistake of his life, he made it as far as the couch before breaking down in tears and crying himself to sleep beneath the throw blanket.Sometime later, Jake heard Anna’s voice. Was it a dream? His head felt heavy with sleep. In the darkness, Anna was pulling his hand.“Come on, sleepy-head, you’ll be more comfortable in bed,” she said.Her voice held no anger, only kindness. It must be a dream. He found himself in his bed. Anna climbed in beside him, her warm back snuggled up against him as she pulled his arm around her. He longed for it to be real, though he knew it couldn’t be. Anna hated him now. It was over. Jake’s mind drifted into blank despair again.Anna was smiling at him. Her face was the most beautiful thing in the world and her gaze felt like being bathed in warm sunshine. She leaned in to kiss him. In the dream logic, this wasn’t a surprise. She loved him as he loved her, and kissing him was the most natural thing in the world. Her lips touched his and he felt his heart grow and expand until it consumed the universe with their love and joy. All they needed was each other, forever. Touching her face, he was the happiest man in the world. He called out her name.“Jake,” he heard Anna’s voice, gentle and tender. “Jake, are you okay?” He felt a warm hand on his cheek.He opened his eyes and saw the light of dawn, soft on Anna’s face. What was she doing here? Genuine concern was in her eyes.“Jake, you were having a dream. Are you okay?”As he woke up more, he realized his dick felt strange. Moving his hand, he found it was on Anna’s hip, and her hip was wet. The sheets were wet. His crotch was wet. With horror he realized it had been a wet dream. The biggest, messiest wet dream of his life. And it was all over Anna.His body involuntarily jerked in panic. Tears erupted from his eyes and he started gasping, unable to speak even if he knew what to say. What was she even doing here? He couldn’t see clearly through the tears, but he had no trouble imagining the hateful look she must be giving him.“Sorry!” he blurted. “Oh god, I’m so sorry.” He started to pull back, to climb out of the bed and away from the mess, away from everything. But she gently pulled him back down beside her.“Shhhh, don’t talk,” she said. “Just look into my eyes and breathe.”Jake squeezed his eyes shut, too ashamed to look at her.“Everything’s okay, Jake,” Anna continued. “I’m here with you, and everything is okay.”Jake opened his mouth to apologize again but she put a finger over his lips before he could speak.“There’s nothing to say. Just breathe with me.”He opened his eyes and through the tears saw Anna’s kind eyes looking into his. He inhaled, and his chest jerked with a suppressed sob.“Everything’s okay, Jake. Just breathe with me.”Jake took another breath, and he managed to make it a bit smoother. Anna smiled and stroked his temple. He focused on the warmth of her hand on his face and tried to forget the shameful wet mess between them on the sheets.Eventually his breathing calmed down. Anna used her thumb to wipe the tears off his cheeks, and she smiled at him.“Now we’re going to do something silly,” Anna said, “And you’re not going to argue with me. You’re going to come with me to the shower, but first you’re going to close your eyes. Do you trust me?”Jake was puzzled but he nodded and closed his eyes. He felt her pull the cold sticky sheet off them, and then she helped him stand up. Holding him from the side, she slowly guided him, and he realized she was doing this so he wouldn’t look at the mess on the bed. He felt the shame lurch back into his heart, but at that very instant she put her hand on his chest, right over his heart, and he calmed back down.He kept his eyes closed as his feet touched the cold tile of the bathroom. He heard Anna start the shower, and then she pulled them together into the hot water. She pressed the front of her body against the front of his and squeezed him close, her head on his shoulder with her face against his neck. Her breasts were soft and comforting. Her hips pushed against his and he felt his shrunken, ashamed dick press against her thighs. He put his arms around her and returned the hug. The hot water poured over them both and he felt his body relaxing.For a few minutes they just held each other. Anna adjusted the water slightly hotter. The air filled with steam and their bodies seemed to blend as the water coursed over their shoulders. Anna sighed happily against his neck. She didn’t hate him for ejaculating on her in his sleep. She wasn’t repelled. She didn’t find him revolting. Anna squeezed him tighter, then pulled back from her hug.“You can open your eyes now.” She was smiling at him. She put her finger to his lips and then grabbed the shampoo bottle. Her fingers massaged the shampoo into his scalp and his eyes rolled back in pleasure. She rubbed far longer than was needed to wash his hair, clearly enjoying his reaction. With a soapy wash cloth, she rubbed his shoulders. Her thumbs worked into his muscles as she washed down his back, down each arm, across his chest and down his belly.Without hesitation she gently held his shrunken dick and stroked it carefully with the wash cloth. It wasn’t sexual as she cleaned him, it was simply loving. She washed his bottom, his legs, and his feet, including scrubbing between each toe.She pushed him back into the hot water to rinse and held a finger up to tell him to stay there. Then she carefully shampooed her own hair, and washed her own body, making sure he was watching. Finally, she joined him in the hot stream of water and hugged him as she rinsed.When Anna turned the water off she grabbed a fresh towel and dried him carefully over his whole body before drying herself while he watched. He laughed when she used the hair dryer on him, blowing warm air all over their bodies until they were fully dry before she got a brush and started drying his hair too. She had fun styling his hair to look ridiculous, and then quickly dried her own hair too.Anna wrapped them each in bath robes to stay warm, and walked him to the kitchen. She put him in a chair and he watched while she made coffee, toast, and eggs. She sat beside him while they ate in silence, watching each other and giggling now and then.When they finished eating, she held up her finger again to tell him to stay in his chair, and then went off to the bedroom. Anna was gone only a few minutes before returning and leading him by the hand back to the bed, which now had fresh sheets. She sat beside him on the bed and smiled at him.“How are you feeling now?” Anna asked. “Better?”Jake smiled. He was clean, warm, and fed. Also, he realized, he was loved. “All better. One hundred percent better. One thousand percent better!”Anna giggled. She couldn’t seem to stop smiling.“Remember when I first asked if I could show you my breasts?”

Her Inverted Intimacy Challenge: Part 3

Play Episode Listen Later Mar 2, 2026

Porn, masterbation, confessions, and demonstrations.By darrenr. Listen to the ► Podcast at Steamy Stories.One evening, Anna sat beside him on the couch with a serious look on her face.“Jake, listen, I know I've already put a lot of burden on our friendship these past weeks. There's something else I want to ask you about. I don't want to do a cycle of agonizing self-doubt this time, so I'm just going to go out on a limb and ask you. Do you promise to tell me if my question makes you uncomfortable?”“Of course I'll tell you,” Jake said.“You know that model you showed me earlier, the one with the inverted nipples?”“Yes,” Jake laughed. “Yes, I remember.”“You found those pictures pretty quickly. Have you looked at pictures of her before?”“Well, yes,” Jake admitted.“And when you looked, it made you feel… aroused?”Jake felt his face turn red. There didn’t seem to be any point in denying the obvious. “Yes.”“Even though she has weird nipples?”“Anna, look. I don’t see her nipples as a negative. It just made her more enticingly unique and fascinating.”Anna nodded. “And when you felt aroused, looking at her pictures, did you… well did it make you want to… touch… yourself?”“Anna, are you asking if I masturbate when I look at porn?”Anna nodded.“The answer is yes, of course I do. I’m not proud of it, and I’ve never talked with anyone about it before. But you seem to sincerely want to know. I’m… I’m not really interested in being teased about this.”“Why would I tease you? I wouldn’t do that.”Jake gave her a doubtful look but saw only sincerity in her expression.“Do you mind if I ask you more questions?”Jake laughed. This woman bared her beautiful body to him every day. How could he say no? With a sigh, he said, “Go for it.”“How did it start? Wasn’t it weird?”“It started quite innocently. I somehow noticed it felt good to touch myself there, and it seemed like all positives and no negatives.”“Were you looking at porn then?”“Oh no, not at first. I’m not even sure I thought about girls at first. That connection came later.”“Did you hide it?”“Well, yes. I clearly sensed this was a private thing.”“And that’s it? All positives, no negatives from the start? No shame involved?”“Oh, I didn’t mean to suggest that. I said it started quite innocently.” Jake paused briefly, and then continued very quietly. “Eventually I got the message it was something to be ashamed of, and I associated profound guilt with it.”“Then you stopped?”Jake shook his head. “Of course not. It felt so good! I simply internalized the shame and self-loathing.”Anna squeezed his hands in hers. “Do you still feel shame?”Jake took a deep breath. “Not the same way. Eventually I realized I wasn’t hurting anyone, and while it isn’t the most productive use of time it’s not worth beating myself up over. The only thing I struggle with anymore is keeping my fantasies respectful.”“What do you mean?”“Well, like… I used to try to imagine what every girl in my school looked like naked. But it didn’t seem right to fantasize about someone who hasn’t… invited me to. I can’t help what images pop into my head and try to ignore the inappropriate ones. That’s why I feel okay about looking at porn. Those people have given permission to be fantasized about.”Anna squeezed his hand and was silent for a while in thought. “For me, I also got the message, as you said, that I shouldn’t touch myself that way. And I didn’t. I’ve since accepted, intellectually, there is nothing wrong with it. But I can’t seem to shake this latent shame. I’ve tried, and it just doesn’t work for me.”“What doesn’t work?” Jake asked.“Touching myself. Masturbating. Every time I try it, I can’t overcome the feelings of shame.”“You’ve never masturbated?” Jake tried to not sound incredulous.“Not really, no.”Jake hesitated a moment, and then asked, “Is it different when you… have sex?”“Oh, I’ve never had sex,” Anna said. “Never really been close. Have you?”Jake shook his head. “No, me neither.”They sat together in silence, the picture of the nude model on the computer forgotten.Anna took a breath and asked, “What does it feel like to… have an orgasm?”Part of him was expecting this question. He thought about the countless times he’d masturbated. What was it like to not know?“It’s okay,” Anna said with disappointment. “I didn’t mean to pry.”“You’re not prying!” Jake said quickly. “Sorry, I’ve never talked about this with anyone. I’m not sure how to describe it. I’m happy to share it with you, but please be patient with me.”Anna’s face relaxed. She waited patiently while Jake thought.“I think it’s kind of like sneezing,” he said.Anna looked confused. “What?”Jake smiled. “Well, kind of. You know that tickle in your nose before a sneeze? It’s annoying, and not a strong sensation, but you know unmistakably a sneeze is coming. The feeling builds, and builds, and then suddenly there’s this out of control explosion that somehow your whole body is involved in. The explosion is related to the tickle, it comes from it, but is orders of magnitude more powerful. More intense. And then afterwards it feels like relief, like all this tension was suddenly released.”Anna looked doubtful. “You’re not really selling it.”Jake laughed. “Well the difference is, unlike a sneeze, it’s all pleasure. It starts as mild pleasure. It feels good, and it builds. It can continue building, and just feels amazing. Sometimes it’s nice to take it slow and enjoy that feeling. When the orgasm hits it feels like the pleasure-o-meter goes off the scale.”Anna laughed. “If it’s that great, why aren’t you masturbating, like, every day?”Jake’s cheeks turned red. “It’s not necessarily every day.”Anna’s eyes widened. “Oh.” She giggled nervously.Jake nodded. Anna sat in quiet thought.“What I’m wondering is,” Anna finally said softly, haltingly, “for me, would it be different if I was… masturbating… with a… friend?”Jake could only see one interpretation for what she just said to him, and yet it seemed impossible.“What do you mean?” Jake asked, studying her face for any sign of joking.“Would you be willing to… masturbate with me?”Jake stared at her stupidly.Anna turned away and moved to stand up. “Sorry, I know that was weird. Please forget I asked.”Jake held tight to her hand. “YES!” he blurted out.Anna turned back toward him.“I mean, no that’s not weird,” Jake continued. “Yes, I will do that with you. Masturbate.” Anna smiled. “After all, that’s an extremely normal thing for friends to do together.”They both laughed. “What’s your vision?” Jake asked. “How will this work?”Anna gestured at the computer in Jake’s lap. “Do you think you could find a movie of something we could both, um, enjoy?”Jake laughed. “Can you be more specific?”“A man and a woman having sex?”“Okay. Any turn offs?”“What do you mean?”“You haven’t watched much porn, have you?”“No,” Anna answered.“That’s okay. Let me sketch a typical ‘plot’ for you. Couple kisses. Couple undresses. Couple takes turns performing oral sex on each other. Man puts penis in woman’s vagina. Lots of thrusting and then, usually, pulling out and ejaculating on the woman.”Anna made a face of disgust. “ON her? Why do they pull out like that?”Jake laughed. “Okay noted, what penises do is disgusting. This brings up another issue we should discuss. If we do this together, I feel I must point out to you I have a penis, and when I orgasm my penis ejaculates semen. If that is gross to you, maybe this isn’t a great idea?”Jake felt a little bad confronting her so directly on this. He thought it was disgusting too, but she hurt his feelings.“I’m sorry, you’re right. But I am curious–why is it normal for the man to pull out?”“I don’t know, I think just so the camera can see the climax? Anyway, I’ll find one where the penis stays inside. Any other concerns?”“Do they always do oral sex? It seems gross to put your mouth where someone pees.”“Not always,” Jake said, “though it’s very common.”“Why is gross stuff common in porn? That doesn’t seem sexy.”Jake thought about how much he’d like to put his mouth on her. “I think it depends on the relationship. A stranger, or someone you’re not attracted to, then I agree it’s a big yuck. Someone you are attracted to, someone you care for deeply and find beautiful and appealing, well, maybe it’s a special intimacy? I’d also guess it feels good in a unique way. I have no personal experience, though. Just speculating.”“Hmmm.” Anna seemed doubtful.“You’d prefer something without oral sex?” Jake asked.“At least to start, please.”Jake found a suitably tasteful example of the genre, put the laptop on the coffee table in front of them, and started the video. Sitting beside Anna, Jake became very conscious of his shrunken dick. He was too embarrassed to be aroused or to touch himself, and his hands rested on his thighs. Anna sat in about the same position, hands on her thighs.The woman in the video took her bra off. She had small breasts with big nipples.“I like her breasts,” Anna said. “She has great nipples. Do you like them?”“Yes, they’re nice.” Jake would have preferred to be looking at Anna’s, though.The woman in the video pulled down the man’s pants and stroked his dick with her hands. “What a beautiful cock,” the woman said in a sultry voice.Anna giggled. “Do people really talk that way?”Jake shrugged. “They do in porn, at least.”“Cock is such a funny word,” Anna said. “Is that what you call your penis?”Jake let out a short laugh. “Believe it or not, I don’t talk to my penis that often.”“I think you mean you don’t talk to your COCK,” Anna said. She nodded toward the screen. “His cock seems to like her,” she said, clearly enjoying the word. She looked over at Jake’s shrunken dick, stark evidence of how uncomfortable he was in this unusual situation. “But yours doesn’t seem so interested. Do you want to try a different video?”“Sorry,” Jake said. “It’s not the video. This just feels weird. I feel a bit paralyzed.”“It is awkward, but we can overcome it,” Anna said. “How do you, normally, how do you touch yourself?”Jake spoke slowly, feeling nervous. “I hold my… penis…”“Cock,” Anna corrected with a smile.“Okay, I hold my cock, and I squeeze until it is hard. Once hard I… I stroke up and down the length of it.”Anna nodded, staring at his limp dick.“How about…” Jake swallowed. “How about you?”Anna laughed. “Well as I explained I don’t really know what I’m doing.”“Okay, I know, but what have you tried? What is your… plan for this attempt?”Anna frowned. “Just general rubbing around my vulva, I suppose.”“Any particular places?”“I’ve read I should focus on my clitoris, but that’s way too sensitive so I kind of rub around it.”“Do you put your finger… inside?” Jake asked.“Oh no,” Anna said, shaking her head. Then, quietly, “I’ve never put anything inside.” She turned to face him. “My gynecologist has, of course, but it was uncomfortable, and I’ve always been a little afraid of doing it on my own. I suppose that sounds stupid.”Jake shook his head. “Not at all. There’s nothing stupid about listening to your feelings. The whole point of masturbating is to feel good.”For a moment they sat in silence watching the video. Finally, Anna put her hand between her legs.“Come on, slow poke,” she said with a smile. “Catch up!”Jake took hold of his shrunken dick.“This isn’t so bad,” Anna said. “How are you doing?”“Doing okay,” Jake said.“Then let’s start stroking.”Jake started rolling his limp dick between his fingers while, out of the corner of his eye, he saw Anna rubbing between her legs. He wanted to watch Anna instead of the video, but he kept his eyes on the screen. The man in the video was now stroking the woman’s pussy. Jake thought about when he had stroked Anna during shaving and moisturizing, which he found deeply erotic but wasn’t supposed to be about sexual pleasure. He wondered what it would be like to stroke her to make her feel good. Sharing his first explicitly sexual moment with her was powerfully arousing and soon he was fully erect.“That’s more like it,” Anna said, nodding at his erection. “Look at that beautiful cock! Feeling better?”Jake took this opportunity to look over at Anna, her friendly face and her bare breasts making his heart long with desire as he stroked himself.“Much,” he answered. “How are you doing? Is it working better having company?”“I think so. It’s still weird, isn’t it?”“Pretty weird!” Jake agreed.In the video, the man was now fingering the woman. She was shaved except for a small patch.“Wow,” Anna said.Eager for any opportunity to turn his head in her direction, Jake asked, “What?”“That woman’s labia are enormous!”“Hmmm, I suppose they’re reasonably prominent,” Jake replied.“Reasonably prominent? They don’t even fit in her vulva, they’re just hanging outside like, 'Hey, what’s up?’”Jake laughed. “Okay, yes. But based on my, uh, experience examining imagery of such things, they’re not unusually large.”Anna sat up a little and leaned down to look between her legs. Jake followed her gaze and was amazed to see she had pulled her outer lips apart, spreading open the petals of her labia.“But look, they’re so much bigger than mine!”Jake took in the sight of her inner pinkness glistening with moisture. Spread open like this, Jake was pretty sure her clitoris wasn’t erect, but his heart thrilled to be seeing in there. His hungry cock throbbed.“You’re so beautiful,” Jake blurted out.Anna laughed. “Right,” she said with sarcasm.“Beautiful,” Jake repeated, looking her in the eye to make his point.Anna looked away in embarrassment and leaned back on the couch, resuming her gentle rubbing while watching the video.“She seems to like that,” Anna said. The woman in the video moaned with pleasure as the man pushed two fingers into her. “She sure talks about her 'pussy’ a lot. Pussy, pussy, pussy! It feels naughty. Say it!”Jake giggled.“Come on, Jake!”“Pussy,” Jake said, quietly.“Pussy!” Anna said, louder.“Pussy!” Jake matched her.“PUSSY!!” Anna nearly yelled. The woman in the video orgasmed loudly while they giggled. “Well she either really enjoyed that or did a good job acting like she did,” Anna said. “I wonder if an orgasm really feels that good.”“It totally does,” Jake said. “Or it can. Speaking of, how are things going in your quest?”Anna sighed. “I don’t know. It feels nice touching myself. I don’t hate the video. I like doing this together, with you, but I don’t feel like the physical sensations are building toward anything.”In the video the man pulled his dick up to the woman’s opening, and then slowly pushed it inside.“That’s kind of beautiful,” Anna said.“It is,” Jake agreed, thinking about Anna.They watched together while the couple in the video had sex, the man thrusting faster and faster while the woman moaned in pleasure. Finally, he grunted, and his body jerked as he ejaculated inside of her, and the video ended.“Oh,” Anna said as she looked over at Jake. “What about your orgasm? Did that video not do it for you?”“It’s not that, exactly,” Jake said while idly gripping his shaft. “It’s more that I wanted to go there with you.”“That is sweet of you, but I’m afraid my equipment might not really work. Honestly, I’m not feeling anything building. But it was very helpful for you to do this with me, because I didn’t feel the shame this way.”“Are you sure you want to give up right away?” Jake asked.Anna’s face looked determined. She shook her head.“No, I’m not giving up,” Anna said. “But, well… do you have another suggestion?”“Have you ever tried, um,” Jake regretted his idea but didn’t know how to back out now. “Water? Like, the tub faucet or shower head?”Anna laughed. “You mean, like, shoot a stream of water into my vagina?”“Well, not so much 'into’ as 'at.’ I don’t know, it was just a thought. I’ve heard some women enjoy it.”“Heard? From who?”“I guess what I should say is I’ve seen videos of women pleasuring themselves with the stream from tub faucets. It could be fake, I certainly don’t know.”“Show me,” she said, nodding toward the computer. Jake found an example. In the video a woman climbed into a bathtub, adjusted the water temperature, and arranged her body so her vulva was in t

Her Inverted Intimacy Challenge: Part 3

Play Episode Listen Later Mar 2, 2026

Porn, masterbation, confessions, and demonstrations.By darrenr. Listen to the ► Podcast at Steamy Stories.One evening, Anna sat beside him on the couch with a serious look on her face.“Jake, listen, I know I've already put a lot of burden on our friendship these past weeks. There's something else I want to ask you about. I don't want to do a cycle of agonizing self-doubt this time, so I'm just going to go out on a limb and ask you. Do you promise to tell me if my question makes you uncomfortable?”“Of course I'll tell you,” Jake said.“You know that model you showed me earlier, the one with the inverted nipples?”“Yes,” Jake laughed. “Yes, I remember.”“You found those pictures pretty quickly. Have you looked at pictures of her before?”“Well, yes,” Jake admitted.“And when you looked, it made you feel… aroused?”Jake felt his face turn red. There didn’t seem to be any point in denying the obvious. “Yes.”“Even though she has weird nipples?”“Anna, look. I don’t see her nipples as a negative. It just made her more enticingly unique and fascinating.”Anna nodded. “And when you felt aroused, looking at her pictures, did you… well did it make you want to… touch… yourself?”“Anna, are you asking if I masturbate when I look at porn?”Anna nodded.“The answer is yes, of course I do. I’m not proud of it, and I’ve never talked with anyone about it before. But you seem to sincerely want to know. I’m… I’m not really interested in being teased about this.”“Why would I tease you? I wouldn’t do that.”Jake gave her a doubtful look but saw only sincerity in her expression.“Do you mind if I ask you more questions?”Jake laughed. This woman bared her beautiful body to him every day. How could he say no? With a sigh, he said, “Go for it.”“How did it start? Wasn’t it weird?”“It started quite innocently. I somehow noticed it felt good to touch myself there, and it seemed like all positives and no negatives.”“Were you looking at porn then?”“Oh no, not at first. I’m not even sure I thought about girls at first. That connection came later.”“Did you hide it?”“Well, yes. I clearly sensed this was a private thing.”“And that’s it? All positives, no negatives from the start? No shame involved?”“Oh, I didn’t mean to suggest that. I said it started quite innocently.” Jake paused briefly, and then continued very quietly. “Eventually I got the message it was something to be ashamed of, and I associated profound guilt with it.”“Then you stopped?”Jake shook his head. “Of course not. It felt so good! I simply internalized the shame and self-loathing.”Anna squeezed his hands in hers. “Do you still feel shame?”Jake took a deep breath. “Not the same way. Eventually I realized I wasn’t hurting anyone, and while it isn’t the most productive use of time it’s not worth beating myself up over. The only thing I struggle with anymore is keeping my fantasies respectful.”“What do you mean?”“Well, like… I used to try to imagine what every girl in my school looked like naked. But it didn’t seem right to fantasize about someone who hasn’t… invited me to. I can’t help what images pop into my head and try to ignore the inappropriate ones. That’s why I feel okay about looking at porn. Those people have given permission to be fantasized about.”Anna squeezed his hand and was silent for a while in thought. “For me, I also got the message, as you said, that I shouldn’t touch myself that way. And I didn’t. I’ve since accepted, intellectually, there is nothing wrong with it. But I can’t seem to shake this latent shame. I’ve tried, and it just doesn’t work for me.”“What doesn’t work?” Jake asked.“Touching myself. Masturbating. Every time I try it, I can’t overcome the feelings of shame.”“You’ve never masturbated?” Jake tried to not sound incredulous.“Not really, no.”Jake hesitated a moment, and then asked, “Is it different when you… have sex?”“Oh, I’ve never had sex,” Anna said. “Never really been close. Have you?”Jake shook his head. “No, me neither.”They sat together in silence, the picture of the nude model on the computer forgotten.Anna took a breath and asked, “What does it feel like to… have an orgasm?”Part of him was expecting this question. He thought about the countless times he’d masturbated. What was it like to not know?“It’s okay,” Anna said with disappointment. “I didn’t mean to pry.”“You’re not prying!” Jake said quickly. “Sorry, I’ve never talked about this with anyone. I’m not sure how to describe it. I’m happy to share it with you, but please be patient with me.”Anna’s face relaxed. She waited patiently while Jake thought.“I think it’s kind of like sneezing,” he said.Anna looked confused. “What?”Jake smiled. “Well, kind of. You know that tickle in your nose before a sneeze? It’s annoying, and not a strong sensation, but you know unmistakably a sneeze is coming. The feeling builds, and builds, and then suddenly there’s this out of control explosion that somehow your whole body is involved in. The explosion is related to the tickle, it comes from it, but is orders of magnitude more powerful. More intense. And then afterwards it feels like relief, like all this tension was suddenly released.”Anna looked doubtful. “You’re not really selling it.”Jake laughed. “Well the difference is, unlike a sneeze, it’s all pleasure. It starts as mild pleasure. It feels good, and it builds. It can continue building, and just feels amazing. Sometimes it’s nice to take it slow and enjoy that feeling. When the orgasm hits it feels like the pleasure-o-meter goes off the scale.”Anna laughed. “If it’s that great, why aren’t you masturbating, like, every day?”Jake’s cheeks turned red. “It’s not necessarily every day.”Anna’s eyes widened. “Oh.” She giggled nervously.Jake nodded. Anna sat in quiet thought.“What I’m wondering is,” Anna finally said softly, haltingly, “for me, would it be different if I was… masturbating… with a… friend?”Jake could only see one interpretation for what she just said to him, and yet it seemed impossible.“What do you mean?” Jake asked, studying her face for any sign of joking.“Would you be willing to… masturbate with me?”Jake stared at her stupidly.Anna turned away and moved to stand up. “Sorry, I know that was weird. Please forget I asked.”Jake held tight to her hand. “YES!” he blurted out.Anna turned back toward him.“I mean, no that’s not weird,” Jake continued. “Yes, I will do that with you. Masturbate.” Anna smiled. “After all, that’s an extremely normal thing for friends to do together.”They both laughed. “What’s your vision?” Jake asked. “How will this work?”Anna gestured at the computer in Jake’s lap. “Do you think you could find a movie of something we could both, um, enjoy?”Jake laughed. “Can you be more specific?”“A man and a woman having sex?”“Okay. Any turn offs?”“What do you mean?”“You haven’t watched much porn, have you?”“No,” Anna answered.“That’s okay. Let me sketch a typical ‘plot’ for you. Couple kisses. Couple undresses. Couple takes turns performing oral sex on each other. Man puts penis in woman’s vagina. Lots of thrusting and then, usually, pulling out and ejaculating on the woman.”Anna made a face of disgust. “ON her? Why do they pull out like that?”Jake laughed. “Okay noted, what penises do is disgusting. This brings up another issue we should discuss. If we do this together, I feel I must point out to you I have a penis, and when I orgasm my penis ejaculates semen. If that is gross to you, maybe this isn’t a great idea?”Jake felt a little bad confronting her so directly on this. He thought it was disgusting too, but she hurt his feelings.“I’m sorry, you’re right. But I am curious–why is it normal for the man to pull out?”“I don’t know, I think just so the camera can see the climax? Anyway, I’ll find one where the penis stays inside. Any other concerns?”“Do they always do oral sex? It seems gross to put your mouth where someone pees.”“Not always,” Jake said, “though it’s very common.”“Why is gross stuff common in porn? That doesn’t seem sexy.”Jake thought about how much he’d like to put his mouth on her. “I think it depends on the relationship. A stranger, or someone you’re not attracted to, then I agree it’s a big yuck. Someone you are attracted to, someone you care for deeply and find beautiful and appealing, well, maybe it’s a special intimacy? I’d also guess it feels good in a unique way. I have no personal experience, though. Just speculating.”“Hmmm.” Anna seemed doubtful.“You’d prefer something without oral sex?” Jake asked.“At least to start, please.”Jake found a suitably tasteful example of the genre, put the laptop on the coffee table in front of them, and started the video. Sitting beside Anna, Jake became very conscious of his shrunken dick. He was too embarrassed to be aroused or to touch himself, and his hands rested on his thighs. Anna sat in about the same position, hands on her thighs.The woman in the video took her bra off. She had small breasts with big nipples.“I like her breasts,” Anna said. “She has great nipples. Do you like them?”“Yes, they’re nice.” Jake would have preferred to be looking at Anna’s, though.The woman in the video pulled down the man’s pants and stroked his dick with her hands. “What a beautiful cock,” the woman said in a sultry voice.Anna giggled. “Do people really talk that way?”Jake shrugged. “They do in porn, at least.”“Cock is such a funny word,” Anna said. “Is that what you call your penis?”Jake let out a short laugh. “Believe it or not, I don’t talk to my penis that often.”“I think you mean you don’t talk to your COCK,” Anna said. She nodded toward the screen. “His cock seems to like her,” she said, clearly enjoying the word. She looked over at Jake’s shrunken dick, stark evidence of how uncomfortable he was in this unusual situation. “But yours doesn’t seem so interested. Do you want to try a different video?”“Sorry,” Jake said. “It’s not the video. This just feels weird. I feel a bit paralyzed.”“It is awkward, but we can overcome it,” Anna said. “How do you, normally, how do you touch yourself?”Jake spoke slowly, feeling nervous. “I hold my… penis…”“Cock,” Anna corrected with a smile.“Okay, I hold my cock, and I squeeze until it is hard. Once hard I… I stroke up and down the length of it.”Anna nodded, staring at his limp dick.“How about…” Jake swallowed. “How about you?”Anna laughed. “Well as I explained I don’t really know what I’m doing.”“Okay, I know, but what have you tried? What is your… plan for this attempt?”Anna frowned. “Just general rubbing around my vulva, I suppose.”“Any particular places?”“I’ve read I should focus on my clitoris, but that’s way too sensitive so I kind of rub around it.”“Do you put your finger… inside?” Jake asked.“Oh no,” Anna said, shaking her head. Then, quietly, “I’ve never put anything inside.” She turned to face him. “My gynecologist has, of course, but it was uncomfortable, and I’ve always been a little afraid of doing it on my own. I suppose that sounds stupid.”Jake shook his head. “Not at all. There’s nothing stupid about listening to your feelings. The whole point of masturbating is to feel good.”For a moment they sat in silence watching the video. Finally, Anna put her hand between her legs.“Come on, slow poke,” she said with a smile. “Catch up!”Jake took hold of his shrunken dick.“This isn’t so bad,” Anna said. “How are you doing?”“Doing okay,” Jake said.“Then let’s start stroking.”Jake started rolling his limp dick between his fingers while, out of the corner of his eye, he saw Anna rubbing between her legs. He wanted to watch Anna instead of the video, but he kept his eyes on the screen. The man in the video was now stroking the woman’s pussy. Jake thought about when he had stroked Anna during shaving and moisturizing, which he found deeply erotic but wasn’t supposed to be about sexual pleasure. He wondered what it would be like to stroke her to make her feel good. Sharing his first explicitly sexual moment with her was powerfully arousing and soon he was fully erect.“That’s more like it,” Anna said, nodding at his erection. “Look at that beautiful cock! Feeling better?”Jake took this opportunity to look over at Anna, her friendly face and her bare breasts making his heart long with desire as he stroked himself.“Much,” he answered. “How are you doing? Is it working better having company?”“I think so. It’s still weird, isn’t it?”“Pretty weird!” Jake agreed.In the video, the man was now fingering the woman. She was shaved except for a small patch.“Wow,” Anna said.Eager for any opportunity to turn his head in her direction, Jake asked, “What?”“That woman’s labia are enormous!”“Hmmm, I suppose they’re reasonably prominent,” Jake replied.“Reasonably prominent? They don’t even fit in her vulva, they’re just hanging outside like, 'Hey, what’s up?’”Jake laughed. “Okay, yes. But based on my, uh, experience examining imagery of such things, they’re not unusually large.”Anna sat up a little and leaned down to look between her legs. Jake followed her gaze and was amazed to see she had pulled her outer lips apart, spreading open the petals of her labia.“But look, they’re so much bigger than mine!”Jake took in the sight of her inner pinkness glistening with moisture. Spread open like this, Jake was pretty sure her clitoris wasn’t erect, but his heart thrilled to be seeing in there. His hungry cock throbbed.“You’re so beautiful,” Jake blurted out.Anna laughed. “Right,” she said with sarcasm.“Beautiful,” Jake repeated, looking her in the eye to make his point.Anna looked away in embarrassment and leaned back on the couch, resuming her gentle rubbing while watching the video.“She seems to like that,” Anna said. The woman in the video moaned with pleasure as the man pushed two fingers into her. “She sure talks about her 'pussy’ a lot. Pussy, pussy, pussy! It feels naughty. Say it!”Jake giggled.“Come on, Jake!”“Pussy,” Jake said, quietly.“Pussy!” Anna said, louder.“Pussy!” Jake matched her.“PUSSY!!” Anna nearly yelled. The woman in the video orgasmed loudly while they giggled. “Well she either really enjoyed that or did a good job acting like she did,” Anna said. “I wonder if an orgasm really feels that good.”“It totally does,” Jake said. “Or it can. Speaking of, how are things going in your quest?”Anna sighed. “I don’t know. It feels nice touching myself. I don’t hate the video. I like doing this together, with you, but I don’t feel like the physical sensations are building toward anything.”In the video the man pulled his dick up to the woman’s opening, and then slowly pushed it inside.“That’s kind of beautiful,” Anna said.“It is,” Jake agreed, thinking about Anna.They watched together while the couple in the video had sex, the man thrusting faster and faster while the woman moaned in pleasure. Finally, he grunted, and his body jerked as he ejaculated inside of her, and the video ended.“Oh,” Anna said as she looked over at Jake. “What about your orgasm? Did that video not do it for you?”“It’s not that, exactly,” Jake said while idly gripping his shaft. “It’s more that I wanted to go there with you.”“That is sweet of you, but I’m afraid my equipment might not really work. Honestly, I’m not feeling anything building. But it was very helpful for you to do this with me, because I didn’t feel the shame this way.”“Are you sure you want to give up right away?” Jake asked.Anna’s face looked determined. She shook her head.“No, I’m not giving up,” Anna said. “But, well… do you have another suggestion?”“Have you ever tried, um,” Jake regretted his idea but didn’t know how to back out now. “Water? Like, the tub faucet or shower head?”Anna laughed. “You mean, like, shoot a stream of water into my vagina?”“Well, not so much 'into’ as 'at.’ I don’t know, it was just a thought. I’ve heard some women enjoy it.”“Heard? From who?”“I guess what I should say is I’ve seen videos of women pleasuring themselves with the stream from tub faucets. It could be fake, I certainly don’t know.”“Show me,” she said, nodding toward the computer. Jake found an example. In the video a woman climbed into a bathtub, adjusted the water temperature, and arranged her body so her vulva was in t

Her Inverted Intimacy Challenge: Part 3

Play Episode Listen Later Mar 2, 2026

Porn, masterbation, confessions, and demonstrations.By darrenr. Listen to the ► Podcast at Steamy Stories.One evening, Anna sat beside him on the couch with a serious look on her face.“Jake, listen, I know I've already put a lot of burden on our friendship these past weeks. There's something else I want to ask you about. I don't want to do a cycle of agonizing self-doubt this time, so I'm just going to go out on a limb and ask you. Do you promise to tell me if my question makes you uncomfortable?”“Of course I'll tell you,” Jake said.“You know that model you showed me earlier, the one with the inverted nipples?”“Yes,” Jake laughed. “Yes, I remember.”“You found those pictures pretty quickly. Have you looked at pictures of her before?”“Well, yes,” Jake admitted.“And when you looked, it made you feel… aroused?”Jake felt his face turn red. There didn’t seem to be any point in denying the obvious. “Yes.”“Even though she has weird nipples?”“Anna, look. I don’t see her nipples as a negative. It just made her more enticingly unique and fascinating.”Anna nodded. “And when you felt aroused, looking at her pictures, did you… well did it make you want to… touch… yourself?”“Anna, are you asking if I masturbate when I look at porn?”Anna nodded.“The answer is yes, of course I do. I’m not proud of it, and I’ve never talked with anyone about it before. But you seem to sincerely want to know. I’m… I’m not really interested in being teased about this.”“Why would I tease you? I wouldn’t do that.”Jake gave her a doubtful look but saw only sincerity in her expression.“Do you mind if I ask you more questions?”Jake laughed. This woman bared her beautiful body to him every day. How could he say no? With a sigh, he said, “Go for it.”“How did it start? Wasn’t it weird?”“It started quite innocently. I somehow noticed it felt good to touch myself there, and it seemed like all positives and no negatives.”“Were you looking at porn then?”“Oh no, not at first. I’m not even sure I thought about girls at first. That connection came later.”“Did you hide it?”“Well, yes. I clearly sensed this was a private thing.”“And that’s it? All positives, no negatives from the start? No shame involved?”“Oh, I didn’t mean to suggest that. I said it started quite innocently.” Jake paused briefly, and then continued very quietly. “Eventually I got the message it was something to be ashamed of, and I associated profound guilt with it.”“Then you stopped?”Jake shook his head. “Of course not. It felt so good! I simply internalized the shame and self-loathing.”Anna squeezed his hands in hers. “Do you still feel shame?”Jake took a deep breath. “Not the same way. Eventually I realized I wasn’t hurting anyone, and while it isn’t the most productive use of time it’s not worth beating myself up over. The only thing I struggle with anymore is keeping my fantasies respectful.”“What do you mean?”“Well, like… I used to try to imagine what every girl in my school looked like naked. But it didn’t seem right to fantasize about someone who hasn’t… invited me to. I can’t help what images pop into my head and try to ignore the inappropriate ones. That’s why I feel okay about looking at porn. Those people have given permission to be fantasized about.”Anna squeezed his hand and was silent for a while in thought. “For me, I also got the message, as you said, that I shouldn’t touch myself that way. And I didn’t. I’ve since accepted, intellectually, there is nothing wrong with it. But I can’t seem to shake this latent shame. I’ve tried, and it just doesn’t work for me.”“What doesn’t work?” Jake asked.“Touching myself. Masturbating. Every time I try it, I can’t overcome the feelings of shame.”“You’ve never masturbated?” Jake tried to not sound incredulous.“Not really, no.”Jake hesitated a moment, and then asked, “Is it different when you… have sex?”“Oh, I’ve never had sex,” Anna said. “Never really been close. Have you?”Jake shook his head. “No, me neither.”They sat together in silence, the picture of the nude model on the computer forgotten.Anna took a breath and asked, “What does it feel like to… have an orgasm?”Part of him was expecting this question. He thought about the countless times he’d masturbated. What was it like to not know?“It’s okay,” Anna said with disappointment. “I didn’t mean to pry.”“You’re not prying!” Jake said quickly. “Sorry, I’ve never talked about this with anyone. I’m not sure how to describe it. I’m happy to share it with you, but please be patient with me.”Anna’s face relaxed. She waited patiently while Jake thought.“I think it’s kind of like sneezing,” he said.Anna looked confused. “What?”Jake smiled. “Well, kind of. You know that tickle in your nose before a sneeze? It’s annoying, and not a strong sensation, but you know unmistakably a sneeze is coming. The feeling builds, and builds, and then suddenly there’s this out of control explosion that somehow your whole body is involved in. The explosion is related to the tickle, it comes from it, but is orders of magnitude more powerful. More intense. And then afterwards it feels like relief, like all this tension was suddenly released.”Anna looked doubtful. “You’re not really selling it.”Jake laughed. “Well the difference is, unlike a sneeze, it’s all pleasure. It starts as mild pleasure. It feels good, and it builds. It can continue building, and just feels amazing. Sometimes it’s nice to take it slow and enjoy that feeling. When the orgasm hits it feels like the pleasure-o-meter goes off the scale.”Anna laughed. “If it’s that great, why aren’t you masturbating, like, every day?”Jake’s cheeks turned red. “It’s not necessarily every day.”Anna’s eyes widened. “Oh.” She giggled nervously.Jake nodded. Anna sat in quiet thought.“What I’m wondering is,” Anna finally said softly, haltingly, “for me, would it be different if I was… masturbating… with a… friend?”Jake could only see one interpretation for what she just said to him, and yet it seemed impossible.“What do you mean?” Jake asked, studying her face for any sign of joking.“Would you be willing to… masturbate with me?”Jake stared at her stupidly.Anna turned away and moved to stand up. “Sorry, I know that was weird. Please forget I asked.”Jake held tight to her hand. “YES!” he blurted out.Anna turned back toward him.“I mean, no that’s not weird,” Jake continued. “Yes, I will do that with you. Masturbate.” Anna smiled. “After all, that’s an extremely normal thing for friends to do together.”They both laughed. “What’s your vision?” Jake asked. “How will this work?”Anna gestured at the computer in Jake’s lap. “Do you think you could find a movie of something we could both, um, enjoy?”Jake laughed. “Can you be more specific?”“A man and a woman having sex?”“Okay. Any turn offs?”“What do you mean?”“You haven’t watched much porn, have you?”“No,” Anna answered.“That’s okay. Let me sketch a typical ‘plot’ for you. Couple kisses. Couple undresses. Couple takes turns performing oral sex on each other. Man puts penis in woman’s vagina. Lots of thrusting and then, usually, pulling out and ejaculating on the woman.”Anna made a face of disgust. “ON her? Why do they pull out like that?”Jake laughed. “Okay noted, what penises do is disgusting. This brings up another issue we should discuss. If we do this together, I feel I must point out to you I have a penis, and when I orgasm my penis ejaculates semen. If that is gross to you, maybe this isn’t a great idea?”Jake felt a little bad confronting her so directly on this. He thought it was disgusting too, but she hurt his feelings.“I’m sorry, you’re right. But I am curious–why is it normal for the man to pull out?”“I don’t know, I think just so the camera can see the climax? Anyway, I’ll find one where the penis stays inside. Any other concerns?”“Do they always do oral sex? It seems gross to put your mouth where someone pees.”“Not always,” Jake said, “though it’s very common.”“Why is gross stuff common in porn? That doesn’t seem sexy.”Jake thought about how much he’d like to put his mouth on her. “I think it depends on the relationship. A stranger, or someone you’re not attracted to, then I agree it’s a big yuck. Someone you are attracted to, someone you care for deeply and find beautiful and appealing, well, maybe it’s a special intimacy? I’d also guess it feels good in a unique way. I have no personal experience, though. Just speculating.”“Hmmm.” Anna seemed doubtful.“You’d prefer something without oral sex?” Jake asked.“At least to start, please.”Jake found a suitably tasteful example of the genre, put the laptop on the coffee table in front of them, and started the video. Sitting beside Anna, Jake became very conscious of his shrunken dick. He was too embarrassed to be aroused or to touch himself, and his hands rested on his thighs. Anna sat in about the same position, hands on her thighs.The woman in the video took her bra off. She had small breasts with big nipples.“I like her breasts,” Anna said. “She has great nipples. Do you like them?”“Yes, they’re nice.” Jake would have preferred to be looking at Anna’s, though.The woman in the video pulled down the man’s pants and stroked his dick with her hands. “What a beautiful cock,” the woman said in a sultry voice.Anna giggled. “Do people really talk that way?”Jake shrugged. “They do in porn, at least.”“Cock is such a funny word,” Anna said. “Is that what you call your penis?”Jake let out a short laugh. “Believe it or not, I don’t talk to my penis that often.”“I think you mean you don’t talk to your COCK,” Anna said. She nodded toward the screen. “His cock seems to like her,” she said, clearly enjoying the word. She looked over at Jake’s shrunken dick, stark evidence of how uncomfortable he was in this unusual situation. “But yours doesn’t seem so interested. Do you want to try a different video?”“Sorry,” Jake said. “It’s not the video. This just feels weird. I feel a bit paralyzed.”“It is awkward, but we can overcome it,” Anna said. “How do you, normally, how do you touch yourself?”Jake spoke slowly, feeling nervous. “I hold my… penis…”“Cock,” Anna corrected with a smile.“Okay, I hold my cock, and I squeeze until it is hard. Once hard I… I stroke up and down the length of it.”Anna nodded, staring at his limp dick.“How about…” Jake swallowed. “How about you?”Anna laughed. “Well as I explained I don’t really know what I’m doing.”“Okay, I know, but what have you tried? What is your… plan for this attempt?”Anna frowned. “Just general rubbing around my vulva, I suppose.”“Any particular places?”“I’ve read I should focus on my clitoris, but that’s way too sensitive so I kind of rub around it.”“Do you put your finger… inside?” Jake asked.“Oh no,” Anna said, shaking her head. Then, quietly, “I’ve never put anything inside.” She turned to face him. “My gynecologist has, of course, but it was uncomfortable, and I’ve always been a little afraid of doing it on my own. I suppose that sounds stupid.”Jake shook his head. “Not at all. There’s nothing stupid about listening to your feelings. The whole point of masturbating is to feel good.”For a moment they sat in silence watching the video. Finally, Anna put her hand between her legs.“Come on, slow poke,” she said with a smile. “Catch up!”Jake took hold of his shrunken dick.“This isn’t so bad,” Anna said. “How are you doing?”“Doing okay,” Jake said.“Then let’s start stroking.”Jake started rolling his limp dick between his fingers while, out of the corner of his eye, he saw Anna rubbing between her legs. He wanted to watch Anna instead of the video, but he kept his eyes on the screen. The man in the video was now stroking the woman’s pussy. Jake thought about when he had stroked Anna during shaving and moisturizing, which he found deeply erotic but wasn’t supposed to be about sexual pleasure. He wondered what it would be like to stroke her to make her feel good. Sharing his first explicitly sexual moment with her was powerfully arousing and soon he was fully erect.“That’s more like it,” Anna said, nodding at his erection. “Look at that beautiful cock! Feeling better?”Jake took this opportunity to look over at Anna, her friendly face and her bare breasts making his heart long with desire as he stroked himself.“Much,” he answered. “How are you doing? Is it working better having company?”“I think so. It’s still weird, isn’t it?”“Pretty weird!” Jake agreed.In the video, the man was now fingering the woman. She was shaved except for a small patch.“Wow,” Anna said.Eager for any opportunity to turn his head in her direction, Jake asked, “What?”“That woman’s labia are enormous!”“Hmmm, I suppose they’re reasonably prominent,” Jake replied.“Reasonably prominent? They don’t even fit in her vulva, they’re just hanging outside like, 'Hey, what’s up?’”Jake laughed. “Okay, yes. But based on my, uh, experience examining imagery of such things, they’re not unusually large.”Anna sat up a little and leaned down to look between her legs. Jake followed her gaze and was amazed to see she had pulled her outer lips apart, spreading open the petals of her labia.“But look, they’re so much bigger than mine!”Jake took in the sight of her inner pinkness glistening with moisture. Spread open like this, Jake was pretty sure her clitoris wasn’t erect, but his heart thrilled to be seeing in there. His hungry cock throbbed.“You’re so beautiful,” Jake blurted out.Anna laughed. “Right,” she said with sarcasm.“Beautiful,” Jake repeated, looking her in the eye to make his point.Anna looked away in embarrassment and leaned back on the couch, resuming her gentle rubbing while watching the video.“She seems to like that,” Anna said. The woman in the video moaned with pleasure as the man pushed two fingers into her. “She sure talks about her 'pussy’ a lot. Pussy, pussy, pussy! It feels naughty. Say it!”Jake giggled.“Come on, Jake!”“Pussy,” Jake said, quietly.“Pussy!” Anna said, louder.“Pussy!” Jake matched her.“PUSSY!!” Anna nearly yelled. The woman in the video orgasmed loudly while they giggled. “Well she either really enjoyed that or did a good job acting like she did,” Anna said. “I wonder if an orgasm really feels that good.”“It totally does,” Jake said. “Or it can. Speaking of, how are things going in your quest?”Anna sighed. “I don’t know. It feels nice touching myself. I don’t hate the video. I like doing this together, with you, but I don’t feel like the physical sensations are building toward anything.”In the video the man pulled his dick up to the woman’s opening, and then slowly pushed it inside.“That’s kind of beautiful,” Anna said.“It is,” Jake agreed, thinking about Anna.They watched together while the couple in the video had sex, the man thrusting faster and faster while the woman moaned in pleasure. Finally, he grunted, and his body jerked as he ejaculated inside of her, and the video ended.“Oh,” Anna said as she looked over at Jake. “What about your orgasm? Did that video not do it for you?”“It’s not that, exactly,” Jake said while idly gripping his shaft. “It’s more that I wanted to go there with you.”“That is sweet of you, but I’m afraid my equipment might not really work. Honestly, I’m not feeling anything building. But it was very helpful for you to do this with me, because I didn’t feel the shame this way.”“Are you sure you want to give up right away?” Jake asked.Anna’s face looked determined. She shook her head.“No, I’m not giving up,” Anna said. “But, well… do you have another suggestion?”“Have you ever tried, um,” Jake regretted his idea but didn’t know how to back out now. “Water? Like, the tub faucet or shower head?”Anna laughed. “You mean, like, shoot a stream of water into my vagina?”“Well, not so much 'into’ as 'at.’ I don’t know, it was just a thought. I’ve heard some women enjoy it.”“Heard? From who?”“I guess what I should say is I’ve seen videos of women pleasuring themselves with the stream from tub faucets. It could be fake, I certainly don’t know.”“Show me,” she said, nodding toward the computer. Jake found an example. In the video a woman climbed into a bathtub, adjusted the water temperature, and arranged her body so her vulva was in t

Her Inverted Intimacy Challenge: Part 3

Play Episode Listen Later Mar 2, 2026

Porn, masterbation, confessions, and demonstrations.By darrenr. Listen to the ► Podcast at Steamy Stories.One evening, Anna sat beside him on the couch with a serious look on her face.“Jake, listen, I know I've already put a lot of burden on our friendship these past weeks. There's something else I want to ask you about. I don't want to do a cycle of agonizing self-doubt this time, so I'm just going to go out on a limb and ask you. Do you promise to tell me if my question makes you uncomfortable?”“Of course I'll tell you,” Jake said.“You know that model you showed me earlier, the one with the inverted nipples?”“Yes,” Jake laughed. “Yes, I remember.”“You found those pictures pretty quickly. Have you looked at pictures of her before?”“Well, yes,” Jake admitted.“And when you looked, it made you feel… aroused?”Jake felt his face turn red. There didn’t seem to be any point in denying the obvious. “Yes.”“Even though she has weird nipples?”“Anna, look. I don’t see her nipples as a negative. It just made her more enticingly unique and fascinating.”Anna nodded. “And when you felt aroused, looking at her pictures, did you… well did it make you want to… touch… yourself?”“Anna, are you asking if I masturbate when I look at porn?”Anna nodded.“The answer is yes, of course I do. I’m not proud of it, and I’ve never talked with anyone about it before. But you seem to sincerely want to know. I’m… I’m not really interested in being teased about this.”“Why would I tease you? I wouldn’t do that.”Jake gave her a doubtful look but saw only sincerity in her expression.“Do you mind if I ask you more questions?”Jake laughed. This woman bared her beautiful body to him every day. How could he say no? With a sigh, he said, “Go for it.”“How did it start? Wasn’t it weird?”“It started quite innocently. I somehow noticed it felt good to touch myself there, and it seemed like all positives and no negatives.”“Were you looking at porn then?”“Oh no, not at first. I’m not even sure I thought about girls at first. That connection came later.”“Did you hide it?”“Well, yes. I clearly sensed this was a private thing.”“And that’s it? All positives, no negatives from the start? No shame involved?”“Oh, I didn’t mean to suggest that. I said it started quite innocently.” Jake paused briefly, and then continued very quietly. “Eventually I got the message it was something to be ashamed of, and I associated profound guilt with it.”“Then you stopped?”Jake shook his head. “Of course not. It felt so good! I simply internalized the shame and self-loathing.”Anna squeezed his hands in hers. “Do you still feel shame?”Jake took a deep breath. “Not the same way. Eventually I realized I wasn’t hurting anyone, and while it isn’t the most productive use of time it’s not worth beating myself up over. The only thing I struggle with anymore is keeping my fantasies respectful.”“What do you mean?”“Well, like… I used to try to imagine what every girl in my school looked like naked. But it didn’t seem right to fantasize about someone who hasn’t… invited me to. I can’t help what images pop into my head and try to ignore the inappropriate ones. That’s why I feel okay about looking at porn. Those people have given permission to be fantasized about.”Anna squeezed his hand and was silent for a while in thought. “For me, I also got the message, as you said, that I shouldn’t touch myself that way. And I didn’t. I’ve since accepted, intellectually, there is nothing wrong with it. But I can’t seem to shake this latent shame. I’ve tried, and it just doesn’t work for me.”“What doesn’t work?” Jake asked.“Touching myself. Masturbating. Every time I try it, I can’t overcome the feelings of shame.”“You’ve never masturbated?” Jake tried to not sound incredulous.“Not really, no.”Jake hesitated a moment, and then asked, “Is it different when you… have sex?”“Oh, I’ve never had sex,” Anna said. “Never really been close. Have you?”Jake shook his head. “No, me neither.”They sat together in silence, the picture of the nude model on the computer forgotten.Anna took a breath and asked, “What does it feel like to… have an orgasm?”Part of him was expecting this question. He thought about the countless times he’d masturbated. What was it like to not know?“It’s okay,” Anna said with disappointment. “I didn’t mean to pry.”“You’re not prying!” Jake said quickly. “Sorry, I’ve never talked about this with anyone. I’m not sure how to describe it. I’m happy to share it with you, but please be patient with me.”Anna’s face relaxed. She waited patiently while Jake thought.“I think it’s kind of like sneezing,” he said.Anna looked confused. “What?”Jake smiled. “Well, kind of. You know that tickle in your nose before a sneeze? It’s annoying, and not a strong sensation, but you know unmistakably a sneeze is coming. The feeling builds, and builds, and then suddenly there’s this out of control explosion that somehow your whole body is involved in. The explosion is related to the tickle, it comes from it, but is orders of magnitude more powerful. More intense. And then afterwards it feels like relief, like all this tension was suddenly released.”Anna looked doubtful. “You’re not really selling it.”Jake laughed. “Well the difference is, unlike a sneeze, it’s all pleasure. It starts as mild pleasure. It feels good, and it builds. It can continue building, and just feels amazing. Sometimes it’s nice to take it slow and enjoy that feeling. When the orgasm hits it feels like the pleasure-o-meter goes off the scale.”Anna laughed. “If it’s that great, why aren’t you masturbating, like, every day?”Jake’s cheeks turned red. “It’s not necessarily every day.”Anna’s eyes widened. “Oh.” She giggled nervously.Jake nodded. Anna sat in quiet thought.“What I’m wondering is,” Anna finally said softly, haltingly, “for me, would it be different if I was… masturbating… with a… friend?”Jake could only see one interpretation for what she just said to him, and yet it seemed impossible.“What do you mean?” Jake asked, studying her face for any sign of joking.“Would you be willing to… masturbate with me?”Jake stared at her stupidly.Anna turned away and moved to stand up. “Sorry, I know that was weird. Please forget I asked.”Jake held tight to her hand. “YES!” he blurted out.Anna turned back toward him.“I mean, no that’s not weird,” Jake continued. “Yes, I will do that with you. Masturbate.” Anna smiled. “After all, that’s an extremely normal thing for friends to do together.”They both laughed. “What’s your vision?” Jake asked. “How will this work?”Anna gestured at the computer in Jake’s lap. “Do you think you could find a movie of something we could both, um, enjoy?”Jake laughed. “Can you be more specific?”“A man and a woman having sex?”“Okay. Any turn offs?”“What do you mean?”“You haven’t watched much porn, have you?”“No,” Anna answered.“That’s okay. Let me sketch a typical ‘plot’ for you. Couple kisses. Couple undresses. Couple takes turns performing oral sex on each other. Man puts penis in woman’s vagina. Lots of thrusting and then, usually, pulling out and ejaculating on the woman.”Anna made a face of disgust. “ON her? Why do they pull out like that?”Jake laughed. “Okay noted, what penises do is disgusting. This brings up another issue we should discuss. If we do this together, I feel I must point out to you I have a penis, and when I orgasm my penis ejaculates semen. If that is gross to you, maybe this isn’t a great idea?”Jake felt a little bad confronting her so directly on this. He thought it was disgusting too, but she hurt his feelings.“I’m sorry, you’re right. But I am curious–why is it normal for the man to pull out?”“I don’t know, I think just so the camera can see the climax? Anyway, I’ll find one where the penis stays inside. Any other concerns?”“Do they always do oral sex? It seems gross to put your mouth where someone pees.”“Not always,” Jake said, “though it’s very common.”“Why is gross stuff common in porn? That doesn’t seem sexy.”Jake thought about how much he’d like to put his mouth on her. “I think it depends on the relationship. A stranger, or someone you’re not attracted to, then I agree it’s a big yuck. Someone you are attracted to, someone you care for deeply and find beautiful and appealing, well, maybe it’s a special intimacy? I’d also guess it feels good in a unique way. I have no personal experience, though. Just speculating.”“Hmmm.” Anna seemed doubtful.“You’d prefer something without oral sex?” Jake asked.“At least to start, please.”Jake found a suitably tasteful example of the genre, put the laptop on the coffee table in front of them, and started the video. Sitting beside Anna, Jake became very conscious of his shrunken dick. He was too embarrassed to be aroused or to touch himself, and his hands rested on his thighs. Anna sat in about the same position, hands on her thighs.The woman in the video took her bra off. She had small breasts with big nipples.“I like her breasts,” Anna said. “She has great nipples. Do you like them?”“Yes, they’re nice.” Jake would have preferred to be looking at Anna’s, though.The woman in the video pulled down the man’s pants and stroked his dick with her hands. “What a beautiful cock,” the woman said in a sultry voice.Anna giggled. “Do people really talk that way?”Jake shrugged. “They do in porn, at least.”“Cock is such a funny word,” Anna said. “Is that what you call your penis?”Jake let out a short laugh. “Believe it or not, I don’t talk to my penis that often.”“I think you mean you don’t talk to your COCK,” Anna said. She nodded toward the screen. “His cock seems to like her,” she said, clearly enjoying the word. She looked over at Jake’s shrunken dick, stark evidence of how uncomfortable he was in this unusual situation. “But yours doesn’t seem so interested. Do you want to try a different video?”“Sorry,” Jake said. “It’s not the video. This just feels weird. I feel a bit paralyzed.”“It is awkward, but we can overcome it,” Anna said. “How do you, normally, how do you touch yourself?”Jake spoke slowly, feeling nervous. “I hold my… penis…”“Cock,” Anna corrected with a smile.“Okay, I hold my cock, and I squeeze until it is hard. Once hard I… I stroke up and down the length of it.”Anna nodded, staring at his limp dick.“How about…” Jake swallowed. “How about you?”Anna laughed. “Well as I explained I don’t really know what I’m doing.”“Okay, I know, but what have you tried? What is your… plan for this attempt?”Anna frowned. “Just general rubbing around my vulva, I suppose.”“Any particular places?”“I’ve read I should focus on my clitoris, but that’s way too sensitive so I kind of rub around it.”“Do you put your finger… inside?” Jake asked.“Oh no,” Anna said, shaking her head. Then, quietly, “I’ve never put anything inside.” She turned to face him. “My gynecologist has, of course, but it was uncomfortable, and I’ve always been a little afraid of doing it on my own. I suppose that sounds stupid.”Jake shook his head. “Not at all. There’s nothing stupid about listening to your feelings. The whole point of masturbating is to feel good.”For a moment they sat in silence watching the video. Finally, Anna put her hand between her legs.“Come on, slow poke,” she said with a smile. “Catch up!”Jake took hold of his shrunken dick.“This isn’t so bad,” Anna said. “How are you doing?”“Doing okay,” Jake said.“Then let’s start stroking.”Jake started rolling his limp dick between his fingers while, out of the corner of his eye, he saw Anna rubbing between her legs. He wanted to watch Anna instead of the video, but he kept his eyes on the screen. The man in the video was now stroking the woman’s pussy. Jake thought about when he had stroked Anna during shaving and moisturizing, which he found deeply erotic but wasn’t supposed to be about sexual pleasure. He wondered what it would be like to stroke her to make her feel good. Sharing his first explicitly sexual moment with her was powerfully arousing and soon he was fully erect.“That’s more like it,” Anna said, nodding at his erection. “Look at that beautiful cock! Feeling better?”Jake took this opportunity to look over at Anna, her friendly face and her bare breasts making his heart long with desire as he stroked himself.“Much,” he answered. “How are you doing? Is it working better having company?”“I think so. It’s still weird, isn’t it?”“Pretty weird!” Jake agreed.In the video, the man was now fingering the woman. She was shaved except for a small patch.“Wow,” Anna said.Eager for any opportunity to turn his head in her direction, Jake asked, “What?”“That woman’s labia are enormous!”“Hmmm, I suppose they’re reasonably prominent,” Jake replied.“Reasonably prominent? They don’t even fit in her vulva, they’re just hanging outside like, 'Hey, what’s up?’”Jake laughed. “Okay, yes. But based on my, uh, experience examining imagery of such things, they’re not unusually large.”Anna sat up a little and leaned down to look between her legs. Jake followed her gaze and was amazed to see she had pulled her outer lips apart, spreading open the petals of her labia.“But look, they’re so much bigger than mine!”Jake took in the sight of her inner pinkness glistening with moisture. Spread open like this, Jake was pretty sure her clitoris wasn’t erect, but his heart thrilled to be seeing in there. His hungry cock throbbed.“You’re so beautiful,” Jake blurted out.Anna laughed. “Right,” she said with sarcasm.“Beautiful,” Jake repeated, looking her in the eye to make his point.Anna looked away in embarrassment and leaned back on the couch, resuming her gentle rubbing while watching the video.“She seems to like that,” Anna said. The woman in the video moaned with pleasure as the man pushed two fingers into her. “She sure talks about her 'pussy’ a lot. Pussy, pussy, pussy! It feels naughty. Say it!”Jake giggled.“Come on, Jake!”“Pussy,” Jake said, quietly.“Pussy!” Anna said, louder.“Pussy!” Jake matched her.“PUSSY!!” Anna nearly yelled. The woman in the video orgasmed loudly while they giggled. “Well she either really enjoyed that or did a good job acting like she did,” Anna said. “I wonder if an orgasm really feels that good.”“It totally does,” Jake said. “Or it can. Speaking of, how are things going in your quest?”Anna sighed. “I don’t know. It feels nice touching myself. I don’t hate the video. I like doing this together, with you, but I don’t feel like the physical sensations are building toward anything.”In the video the man pulled his dick up to the woman’s opening, and then slowly pushed it inside.“That’s kind of beautiful,” Anna said.“It is,” Jake agreed, thinking about Anna.They watched together while the couple in the video had sex, the man thrusting faster and faster while the woman moaned in pleasure. Finally, he grunted, and his body jerked as he ejaculated inside of her, and the video ended.“Oh,” Anna said as she looked over at Jake. “What about your orgasm? Did that video not do it for you?”“It’s not that, exactly,” Jake said while idly gripping his shaft. “It’s more that I wanted to go there with you.”“That is sweet of you, but I’m afraid my equipment might not really work. Honestly, I’m not feeling anything building. But it was very helpful for you to do this with me, because I didn’t feel the shame this way.”“Are you sure you want to give up right away?” Jake asked.Anna’s face looked determined. She shook her head.“No, I’m not giving up,” Anna said. “But, well… do you have another suggestion?”“Have you ever tried, um,” Jake regretted his idea but didn’t know how to back out now. “Water? Like, the tub faucet or shower head?”Anna laughed. “You mean, like, shoot a stream of water into my vagina?”“Well, not so much 'into’ as 'at.’ I don’t know, it was just a thought. I’ve heard some women enjoy it.”“Heard? From who?”“I guess what I should say is I’ve seen videos of women pleasuring themselves with the stream from tub faucets. It could be fake, I certainly don’t know.”“Show me,” she said, nodding toward the computer. Jake found an example. In the video a woman climbed into a bathtub, adjusted the water temperature, and arranged her body so her vulva was in t

Her Inverted Intimacy Challenge: Part 2

Play Episode Listen Later Mar 1, 2026

Platonic friends help with Intimate shaving, complicated by arousal.By darrenr. Listen to the ► Podcast at Steamy Stories.“There's one thing, though,” Anna said hesitantly. “I'm nervous about wielding a razor in such a tender place when I can't see very well down there. Would you, would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it's a big favor. It's no problem if you'd rather not.”Jake couldn't think of anything he wanted to do more than spend some quality time with Anna's vagina.“There’s one thing, though,” Anna said hesitantly. “I’m nervous about wielding a razor in such a tender place when I can’t see very well down there. Would you… would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it’s a big favor. It’s no problem if you’d rather not.”Jake couldn’t think of anything he wanted to do more than spend some quality time with Anna’s vagina.“It’s not that! I’m happy to help. It’s just, I’ve never shaved a, um, you know, a…”“Vulva?” Anna said with a smirk. “It’s okay to use the word. Anyway, neither have I! But you have the advantage of being able to see down there.”“Okay, fair point,” Jake said. “But it also means… well in order to do this, I’ll need to…” Anna raised her eyebrows waiting for him to finish.“I’ll be clean,” Anna said. “I’m going to shower first, of course.”Jake wasn’t expecting that. He shook his head. “Oh, no, I’m not concerned about that. I just mean I’ll need to… touch… you. There. You know, to shave you.”Anna frowned. “Yes, hmm, I see the difficulty now. You’ve got a friend sincerely asking for your help with her most private place, and you’re balking because even a clean vulva is, let’s face it, pretty gross.”“NO!” Jake said. “That’s not it at all!” Anna looked hurt. “I’m sorry, I don’t mean to yell. You’re completely misunderstanding me. I don’t think you’re gross in any way. I don’t think your… vulva is gross. At all. Not to be too corny about it, but I think your whole body is beautiful. Including your vag–, I mean, vulva.” Anna looked skeptical. Jake grimaced. “I’m nervous because… well, you’ve said our relationship isn’t sexual. I have to be honest with you. There’s no way I can touch your body… your vulva… and not be affected. Sexually.”Anna bit her lip and looked down, nodding. “I’m still figuring myself out. I think that experience with Andrew all those years ago affected me more than I realized. I don’t know what I want, or what I feel. I just know I feel safe with you.” She lifted her head to look him in the eye. “Do you think it’s possible to just pretend that it’s not sexual between us?”“Yes, I can do that,” Jake said. “Though my body might react differently.”Anna smiled in relief. “Then there’s nothing to worry about. Once the novelty wears off, you’ll realize what a tedious task you’ve volunteered for. Now come ON already.” Her face bright with happiness, she jumped up from the couch, pulling him by the hand to the bathroom. “I’m happy to help shave you in return, of course.”“That’s probably safest,” Jake said, trying to play it cool as he realized where she would be touching him.They showered together like normal. Anna got two fresh towels, spreading one on the floor of the bathroom and keeping the other folded as a pillow. She unwrapped a new razor and put it, along with a can of shaving cream, beside the towel. Lying down on her back, she stretched her legs out and spread them apart.“Do you think I should shave it all or keep a patch of hair?” she asked.Jake stood transfixed by the sight, contemplating her lovely bush. It was full and fluffy and beautiful, with light brown hair looking impossibly soft. Part of him didn’t want her to shave it, but only part of him.“We could definitely leave a patch of hair if you want. Though even if you start fully shaved it would grow back soon.”“Good point. Let’s just shave it all to start.” She reached for the can of shaving cream.“Wait,” Jake said. “When I’ve shaved my beard in the past it worked much better when I clipped the hair short first. Otherwise the razor gets clogged. I have some small mustache scissors, if you want?”“Good idea,” Anna agreed.Jake dug in his drawer until he found the scissors, and then turned to face her and froze. Could he really do this? He felt a bit faint at the thought of accidentally cutting her.“It’s okay, Jake. I know you’re going to be gentle. Go ahead and start!” She smiled nervously at him. “But please be careful.”Jake took a deep breath and knelt between her open legs. He’d never been this close, and his greedy eyes took in every detail. He looked up to her face, framed at this angle by her lovely breasts, and she gave him an encouraging nod. Taking a deep breath, Jake raised his empty hand toward her and gently grabbed a tuft of hair. It was even softer than it looked.“Your hair is beautiful. Are you sure you want me to cut it?”Anna rolled her eyes. “Yes, I’m sure. Let’s do it!”Slowly, Jake brought the scissors up and snipped off a chunk of hair. Realizing he needed a place to collect it, he spread out a tissue. Anna watched him intently, propped up on her elbows. Carefully he worked, gathering and snipping, gathering and snipping. He gently brushed the loose hairs off her after trimming everything above her cleft.“How are you doing?” Jake asked.“Thank you for being so gentle. I would be a nervous wreck doing this myself.”“It’s my pleasure,” Jake said automatically, before realizing how intensely true the statement was. Quickly, he added, “Are you ready for me to continue working down… lower?”“You mean on my vulva?” She laughed. “Please use the names of my body parts, you silly.”“Sorry, you’re right. Are you ready for me to trim your vulva?”“Absolutely, please go ahead,” Anna said with a smile, though he still saw nervousness in her eyes. She dropped back onto the towel pillow, her breathing only a little shaky.Looking at her tender folds, Jake felt his palms sweating and his heart beating furiously. Gently, so gently, he touched his finger to the top of her cleft and drew it down to tease out the hairs trapped within. It took a few tries to get the hairs pulled off the bit of her inner labia that sat flush with her cleft. Careful to hold the scissors so he could see exactly where they cut and terrified of hurting her, he trimmed down the length of her outer lips.Anna’s hips twitched a little. “That tickles!”“Sorry! I’m not trying to tickle you.”“I know, it’s just a bit of sensory overload. Can you please just pause for a minute and press your palm against my skin, just to give my nerves a minute to calm down?”“Skin? Don’t you mean ‘vulva’?” Jake said.Anna laughed. “Fair point! Yes, please put your hand over my vulva to calm it down.”Jake put his palm against her cleft and felt its warmth, relishing the intimacy. Anna sighed and took a few deep breaths. “Okay, I’m good. Keep going.”“Could you please spread your legs a bit wider, so I can trim at the base of your legs?”“Sure thing!” Anna said. She bent her knees, bringing her feet up to rest against the sides of Jake’s legs as he knelt before her. Her outer lips were pulled apart, revealing moist pinkness inside. Her lovely scent grew stronger in his nose. Jake felt his erection jump. At least she couldn’t see his obvious arousal now. A few more minutes of careful clipping and he was done. He couldn’t be sure, but her inner lips looked wetter than before. He gently brushed the loose hairs away from her cleft and onto the tissue. Remembering how it might tickle, he placed his palm over everything again to relieve her.“Would you like me to clip, um, further down?” Then, remembering her earlier admonishment, added, “Around your, uh, anus?”Anna giggled as she sat up, her cheeks a little red. Anna bit her lip. “I suppose getting embarrassed at this point is silly. Yes, please trim down there, too.” She turned over onto her knees and pushed her bottom into the air, giving Jake his first clear view between her cheeks. His heart yearned with affection for her, the desire to care for her, even her cute little butthole. Only a few wisps of hair grew back there, and he was soon finished clipping.“Okay, I think we’re ready to start shaving,” Jake said. “Does it make sense to do that in the tub with lots of warm water?”“Definitely the tub, but we’re not ready yet. I need to clip you!”“Oh!” Jake said, “I forgot.” It was true. He was disappointed to realize he was quite erect, and with no way to hide it.“Well come on, trade places with me!” Jake stood up, his massive erection hanging out in the open air. He lay on his back feeling exposed and embarrassed. Anna knelt between his legs, and then she picked up his feet and brought them against the sides of her legs, so he was spread apart like she had been. His straining dick pointed up at the wall somewhere above his head.“Sorry about that,” he said, gesturing toward his erection.“Don’t be!” Anna replied. “I think it actually works better to have the skin stretched out for this. See if you can keep it that way. Are you ready?”“Sure, go ahead,” Jake answered. He didn’t expect it to be difficult to stay hard with her breath gently tickling his shaft. Sitting up on his elbows, he watched her gently grab a tuft of hair and clip it. She looked up to make sure he was okay, and then resumed careful clipping. Her breasts hung down in a lovely way as she bent over him clipping. Jake put his head back on the towel pillow and tried to relax, her every touch thrilling him.“I didn’t realize hairs grew up the shaft of your penis.”“Yeah it’s pretty nasty.”“No, it’s not nasty,” Anna said. “Just interesting.” He felt her fingers gingerly wrap around his shaft. “Wow, the skin is so soft. It’s a weird contrast with the hardness beneath the skin.” Jake relished the feel of her hand on him and listened to the soft swish of the scissors.“Are you doing okay?” Anna asked. She paused and kept her hand still on his hardness, the same anti-tickling strategy he’d used on her. It felt so nice. Jake was far more than okay, though he didn’t dare say that.He tilted his head up to look at her. “Perfectly comfortable. Thank you for being so careful.” She smiled at him, and then returned to her trimming. Her tongue poked out between her lips the same way it did when she was focused on some electronics soldering project. Seeing her so dedicated to caring for him made his ridiculous dick strain against her fingers.“Everything is more dynamic down here than I thought,” Anna said.Jake sat up again to give her a questioning look.“I suppose it’s obvious. It just hadn’t occurred to me. Like, when you’re hard it’s not simply rigid. It’s constantly softening a bit and re-hardening. I can even feel your pulse! And your scrotum moves!”Jake laughed. “Yeah I guess it’s all pretty weird.”“Not weird! Interesting.”Anna moved her hand down to his scrotum, her fingers gently stroking it as she trimmed hairs.“Alright, flip over so I can trim your… um,” Anna giggled for a second before continuing. “Your anus.” Jake dreaded this, but he complied. “Oh, I like how this seam of skin connects to your scrotum. This is so interesting!” A few more minutes of trimming and then she was done.“Okay NOW we’re ready for the shaving part,” Anna said brightly.Jake righted himself and helped clean up the tissues of trimmed pubic hair. There was a lot of hair.“Wow, look at us all trimmed!” Anna said, looking back and forth between the two trimmed crotches. “It feels cooler already. This is going to be great!” She started the water running and moved the new razor and can of shaving cream to the edge of the tub. They climbed in together and sat facing each other in the rising water.“This is fun,” Anna said. “I know it must be weird and tedious for you. I really appreciate you doing this with me.”“Are you kidding?” Jake said. “I’m having fun too. It’s not tedious at all.”Anna pulled herself up to sit on the edge of the tub and handed Jake the can of shaving cream. Still sitting in the water, he scooted toward her as she spread her legs apart. Jake squirted some shaving cream into his hand.“Ready?” he asked. Anna nodded, but he could see that her smile was a bit forced. He didn’t blame her for being nervous. He knew he felt more than nervous, and was grateful his hands remained steady. Jake dabbed the cream on the clipped-short hairs above her cleft and massaged it in with circular motions of his fingertips. Then he carefully dragged the razor in downward strokes, with the grain of her hair, stretching her skin flat as needed. Rinsing the razor often, he made sure to avoid re-shaving the same patch of skin. Finally, he was done with her pubic mound and rinsed her with cupped handfuls of water.“Nicely done, Jake!” Anna said, stroking the smooth skin with her hand. “Very nicely done.”Jake smiled, feeling pleased with his work. “Are you ready for me to shave your vulva now?”“Yes please!” Anna replied, though he could tell her enthusiasm was trying to conceal her nervousness.Jake squirted more cream in his hand and dabbed it on either side of her cleft. With both hands he gently rubbed cream along the inside of her legs and along her outer lips. Glancing up to check on her, he saw her cheeks were flushed. Did his touches feel good to her, or was that simply terror? Anna gave him a reassuring smile. Jake tried to focus.Continuing the short downward strokes, Jake gently drew the razor along her outer lips. Terrified of hurting her, with his other hand he stretched the skin flat and pulled it away from her inner labia as he shaved. After several minutes of careful work, she was shaved as far down as he could work at this angle. He brought up cupped handfuls of water to rinse and carefully stroked her skin feeling for any spots he might have missed. After a few touch-up strokes, he felt satisfied.“How is that?” Jake asked, looking up to her face. Anna’s cheeks were even more flushed, and she bit her lower lip. She broke out into a big smile.“Wow, Jake, you did a great job!” She explored all the shaved places with her fingers. “It feels so strange.”“I didn’t do a perfect job,” Jake said. “I was afraid of giving you a razor burn, so I went for gentleness over thoroughness.”“Thank you for being so careful. The whole time I knew I was in safe hands.”“You’re beautiful,” Jake said softly, lost in thought staring at her smooth cleft. Then, catching himself, “I think it looks great! Want me to finish your, uh, anus?”“Definitely!” Anna said. She dipped her bottom in the tub water to get everything freshly wet and turned over on her knees to present her bottom to him. Jake put shaving cream along the inside of each bottom cheek. A few careful strokes of the razor later he was finished, and he stopped to admire his work on her beautiful body.“All done!” he announced.Anna sat back down in the tub. “Alright, your turn now. Up on the edge of the tub!”While shaving Anna, Jake was so focused on being careful that his misbehaving dick shrunk down to nearly normal. Spreading his legs and presenting himself to Anna, however, quickly brought it back to fully erect.“Thank you,” she said. “I was worried how I would do this properly if your penis wasn’t erect. Are you ready?”Jake nodded, and Anna started rubbing shaving cream into his pubic hair. Looking down he watched her beautiful face, completely focused on her task. Her breasts, so comforting to see, jiggled as she moved. Part of him was very present, relishing her touches and attention. Another part of him was so deep in thought it was almost like having an out of body experience. Anna was the one person he cared most about in the whole world. She was his closest friend, the person who most understood him. When he was away from her, he missed her. When he was with her, he felt utterly content. His place didn’t feel like home unless she was there too. This wasn’t mere physical lust, though there was plenty of that as well. He truly loved her. The trouble was he didn’t see a way to tell her this, without risking messing up what he already had. The thought of frightening her off, of not sharing this intimacy with her, was too horrible to consider.Seeing the way she touched him, though, so carefully and tenderly, it was hard to believe she didn’t have any sexual feelings for him.“There we go,” Anna said, waking him from his reverie. Jake looked down to see himself thoroughly hairless. He didn’t get time to really look before she turned him over to shave between his butt cheeks. A minute later she was finished. They rinsed off in the shower and stood next to each other in front of the mirror to admire the results.“We look fantastic. I love this!” Anna said.“You look amazing,” Jake said.“So do you!” Anna was striking poses in the mirror. “Oh, I almost forgot. We need to moisturize.” She dug in her drawer and pulled out a bottle of lotion. “It’s a very gentle lotion suitable for the whole body. Do you mind if I apply it?” Jake shook his head and Anna straightened the towel on the floor for him to lie down upon. Anna used both hands on him to gently massage lotion everywhere she had shaved, including the shaft of his rock-hard dick and his smooth ball sack. Unlike shaving, he was obviously capable of applying lotion to himself without danger. But if she wanted to touch him and be touched by him, he certainly wasn’t going to argue. He was surprised to find Anna spreading the lotion beyond the sha

Her Inverted Intimacy Challenge: Part 2

Play Episode Listen Later Mar 1, 2026

Platonic friends help with Intimate shaving, complicated by arousal.By darrenr. Listen to the ► Podcast at Steamy Stories.“There's one thing, though,” Anna said hesitantly. “I'm nervous about wielding a razor in such a tender place when I can't see very well down there. Would you, would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it's a big favor. It's no problem if you'd rather not.”Jake couldn't think of anything he wanted to do more than spend some quality time with Anna's vagina.“There’s one thing, though,” Anna said hesitantly. “I’m nervous about wielding a razor in such a tender place when I can’t see very well down there. Would you… would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it’s a big favor. It’s no problem if you’d rather not.”Jake couldn’t think of anything he wanted to do more than spend some quality time with Anna’s vagina.“It’s not that! I’m happy to help. It’s just, I’ve never shaved a, um, you know, a…”“Vulva?” Anna said with a smirk. “It’s okay to use the word. Anyway, neither have I! But you have the advantage of being able to see down there.”“Okay, fair point,” Jake said. “But it also means… well in order to do this, I’ll need to…” Anna raised her eyebrows waiting for him to finish.“I’ll be clean,” Anna said. “I’m going to shower first, of course.”Jake wasn’t expecting that. He shook his head. “Oh, no, I’m not concerned about that. I just mean I’ll need to… touch… you. There. You know, to shave you.”Anna frowned. “Yes, hmm, I see the difficulty now. You’ve got a friend sincerely asking for your help with her most private place, and you’re balking because even a clean vulva is, let’s face it, pretty gross.”“NO!” Jake said. “That’s not it at all!” Anna looked hurt. “I’m sorry, I don’t mean to yell. You’re completely misunderstanding me. I don’t think you’re gross in any way. I don’t think your… vulva is gross. At all. Not to be too corny about it, but I think your whole body is beautiful. Including your vag–, I mean, vulva.” Anna looked skeptical. Jake grimaced. “I’m nervous because… well, you’ve said our relationship isn’t sexual. I have to be honest with you. There’s no way I can touch your body… your vulva… and not be affected. Sexually.”Anna bit her lip and looked down, nodding. “I’m still figuring myself out. I think that experience with Andrew all those years ago affected me more than I realized. I don’t know what I want, or what I feel. I just know I feel safe with you.” She lifted her head to look him in the eye. “Do you think it’s possible to just pretend that it’s not sexual between us?”“Yes, I can do that,” Jake said. “Though my body might react differently.”Anna smiled in relief. “Then there’s nothing to worry about. Once the novelty wears off, you’ll realize what a tedious task you’ve volunteered for. Now come ON already.” Her face bright with happiness, she jumped up from the couch, pulling him by the hand to the bathroom. “I’m happy to help shave you in return, of course.”“That’s probably safest,” Jake said, trying to play it cool as he realized where she would be touching him.They showered together like normal. Anna got two fresh towels, spreading one on the floor of the bathroom and keeping the other folded as a pillow. She unwrapped a new razor and put it, along with a can of shaving cream, beside the towel. Lying down on her back, she stretched her legs out and spread them apart.“Do you think I should shave it all or keep a patch of hair?” she asked.Jake stood transfixed by the sight, contemplating her lovely bush. It was full and fluffy and beautiful, with light brown hair looking impossibly soft. Part of him didn’t want her to shave it, but only part of him.“We could definitely leave a patch of hair if you want. Though even if you start fully shaved it would grow back soon.”“Good point. Let’s just shave it all to start.” She reached for the can of shaving cream.“Wait,” Jake said. “When I’ve shaved my beard in the past it worked much better when I clipped the hair short first. Otherwise the razor gets clogged. I have some small mustache scissors, if you want?”“Good idea,” Anna agreed.Jake dug in his drawer until he found the scissors, and then turned to face her and froze. Could he really do this? He felt a bit faint at the thought of accidentally cutting her.“It’s okay, Jake. I know you’re going to be gentle. Go ahead and start!” She smiled nervously at him. “But please be careful.”Jake took a deep breath and knelt between her open legs. He’d never been this close, and his greedy eyes took in every detail. He looked up to her face, framed at this angle by her lovely breasts, and she gave him an encouraging nod. Taking a deep breath, Jake raised his empty hand toward her and gently grabbed a tuft of hair. It was even softer than it looked.“Your hair is beautiful. Are you sure you want me to cut it?”Anna rolled her eyes. “Yes, I’m sure. Let’s do it!”Slowly, Jake brought the scissors up and snipped off a chunk of hair. Realizing he needed a place to collect it, he spread out a tissue. Anna watched him intently, propped up on her elbows. Carefully he worked, gathering and snipping, gathering and snipping. He gently brushed the loose hairs off her after trimming everything above her cleft.“How are you doing?” Jake asked.“Thank you for being so gentle. I would be a nervous wreck doing this myself.”“It’s my pleasure,” Jake said automatically, before realizing how intensely true the statement was. Quickly, he added, “Are you ready for me to continue working down… lower?”“You mean on my vulva?” She laughed. “Please use the names of my body parts, you silly.”“Sorry, you’re right. Are you ready for me to trim your vulva?”“Absolutely, please go ahead,” Anna said with a smile, though he still saw nervousness in her eyes. She dropped back onto the towel pillow, her breathing only a little shaky.Looking at her tender folds, Jake felt his palms sweating and his heart beating furiously. Gently, so gently, he touched his finger to the top of her cleft and drew it down to tease out the hairs trapped within. It took a few tries to get the hairs pulled off the bit of her inner labia that sat flush with her cleft. Careful to hold the scissors so he could see exactly where they cut and terrified of hurting her, he trimmed down the length of her outer lips.Anna’s hips twitched a little. “That tickles!”“Sorry! I’m not trying to tickle you.”“I know, it’s just a bit of sensory overload. Can you please just pause for a minute and press your palm against my skin, just to give my nerves a minute to calm down?”“Skin? Don’t you mean ‘vulva’?” Jake said.Anna laughed. “Fair point! Yes, please put your hand over my vulva to calm it down.”Jake put his palm against her cleft and felt its warmth, relishing the intimacy. Anna sighed and took a few deep breaths. “Okay, I’m good. Keep going.”“Could you please spread your legs a bit wider, so I can trim at the base of your legs?”“Sure thing!” Anna said. She bent her knees, bringing her feet up to rest against the sides of Jake’s legs as he knelt before her. Her outer lips were pulled apart, revealing moist pinkness inside. Her lovely scent grew stronger in his nose. Jake felt his erection jump. At least she couldn’t see his obvious arousal now. A few more minutes of careful clipping and he was done. He couldn’t be sure, but her inner lips looked wetter than before. He gently brushed the loose hairs away from her cleft and onto the tissue. Remembering how it might tickle, he placed his palm over everything again to relieve her.“Would you like me to clip, um, further down?” Then, remembering her earlier admonishment, added, “Around your, uh, anus?”Anna giggled as she sat up, her cheeks a little red. Anna bit her lip. “I suppose getting embarrassed at this point is silly. Yes, please trim down there, too.” She turned over onto her knees and pushed her bottom into the air, giving Jake his first clear view between her cheeks. His heart yearned with affection for her, the desire to care for her, even her cute little butthole. Only a few wisps of hair grew back there, and he was soon finished clipping.“Okay, I think we’re ready to start shaving,” Jake said. “Does it make sense to do that in the tub with lots of warm water?”“Definitely the tub, but we’re not ready yet. I need to clip you!”“Oh!” Jake said, “I forgot.” It was true. He was disappointed to realize he was quite erect, and with no way to hide it.“Well come on, trade places with me!” Jake stood up, his massive erection hanging out in the open air. He lay on his back feeling exposed and embarrassed. Anna knelt between his legs, and then she picked up his feet and brought them against the sides of her legs, so he was spread apart like she had been. His straining dick pointed up at the wall somewhere above his head.“Sorry about that,” he said, gesturing toward his erection.“Don’t be!” Anna replied. “I think it actually works better to have the skin stretched out for this. See if you can keep it that way. Are you ready?”“Sure, go ahead,” Jake answered. He didn’t expect it to be difficult to stay hard with her breath gently tickling his shaft. Sitting up on his elbows, he watched her gently grab a tuft of hair and clip it. She looked up to make sure he was okay, and then resumed careful clipping. Her breasts hung down in a lovely way as she bent over him clipping. Jake put his head back on the towel pillow and tried to relax, her every touch thrilling him.“I didn’t realize hairs grew up the shaft of your penis.”“Yeah it’s pretty nasty.”“No, it’s not nasty,” Anna said. “Just interesting.” He felt her fingers gingerly wrap around his shaft. “Wow, the skin is so soft. It’s a weird contrast with the hardness beneath the skin.” Jake relished the feel of her hand on him and listened to the soft swish of the scissors.“Are you doing okay?” Anna asked. She paused and kept her hand still on his hardness, the same anti-tickling strategy he’d used on her. It felt so nice. Jake was far more than okay, though he didn’t dare say that.He tilted his head up to look at her. “Perfectly comfortable. Thank you for being so careful.” She smiled at him, and then returned to her trimming. Her tongue poked out between her lips the same way it did when she was focused on some electronics soldering project. Seeing her so dedicated to caring for him made his ridiculous dick strain against her fingers.“Everything is more dynamic down here than I thought,” Anna said.Jake sat up again to give her a questioning look.“I suppose it’s obvious. It just hadn’t occurred to me. Like, when you’re hard it’s not simply rigid. It’s constantly softening a bit and re-hardening. I can even feel your pulse! And your scrotum moves!”Jake laughed. “Yeah I guess it’s all pretty weird.”“Not weird! Interesting.”Anna moved her hand down to his scrotum, her fingers gently stroking it as she trimmed hairs.“Alright, flip over so I can trim your… um,” Anna giggled for a second before continuing. “Your anus.” Jake dreaded this, but he complied. “Oh, I like how this seam of skin connects to your scrotum. This is so interesting!” A few more minutes of trimming and then she was done.“Okay NOW we’re ready for the shaving part,” Anna said brightly.Jake righted himself and helped clean up the tissues of trimmed pubic hair. There was a lot of hair.“Wow, look at us all trimmed!” Anna said, looking back and forth between the two trimmed crotches. “It feels cooler already. This is going to be great!” She started the water running and moved the new razor and can of shaving cream to the edge of the tub. They climbed in together and sat facing each other in the rising water.“This is fun,” Anna said. “I know it must be weird and tedious for you. I really appreciate you doing this with me.”“Are you kidding?” Jake said. “I’m having fun too. It’s not tedious at all.”Anna pulled herself up to sit on the edge of the tub and handed Jake the can of shaving cream. Still sitting in the water, he scooted toward her as she spread her legs apart. Jake squirted some shaving cream into his hand.“Ready?” he asked. Anna nodded, but he could see that her smile was a bit forced. He didn’t blame her for being nervous. He knew he felt more than nervous, and was grateful his hands remained steady. Jake dabbed the cream on the clipped-short hairs above her cleft and massaged it in with circular motions of his fingertips. Then he carefully dragged the razor in downward strokes, with the grain of her hair, stretching her skin flat as needed. Rinsing the razor often, he made sure to avoid re-shaving the same patch of skin. Finally, he was done with her pubic mound and rinsed her with cupped handfuls of water.“Nicely done, Jake!” Anna said, stroking the smooth skin with her hand. “Very nicely done.”Jake smiled, feeling pleased with his work. “Are you ready for me to shave your vulva now?”“Yes please!” Anna replied, though he could tell her enthusiasm was trying to conceal her nervousness.Jake squirted more cream in his hand and dabbed it on either side of her cleft. With both hands he gently rubbed cream along the inside of her legs and along her outer lips. Glancing up to check on her, he saw her cheeks were flushed. Did his touches feel good to her, or was that simply terror? Anna gave him a reassuring smile. Jake tried to focus.Continuing the short downward strokes, Jake gently drew the razor along her outer lips. Terrified of hurting her, with his other hand he stretched the skin flat and pulled it away from her inner labia as he shaved. After several minutes of careful work, she was shaved as far down as he could work at this angle. He brought up cupped handfuls of water to rinse and carefully stroked her skin feeling for any spots he might have missed. After a few touch-up strokes, he felt satisfied.“How is that?” Jake asked, looking up to her face. Anna’s cheeks were even more flushed, and she bit her lower lip. She broke out into a big smile.“Wow, Jake, you did a great job!” She explored all the shaved places with her fingers. “It feels so strange.”“I didn’t do a perfect job,” Jake said. “I was afraid of giving you a razor burn, so I went for gentleness over thoroughness.”“Thank you for being so careful. The whole time I knew I was in safe hands.”“You’re beautiful,” Jake said softly, lost in thought staring at her smooth cleft. Then, catching himself, “I think it looks great! Want me to finish your, uh, anus?”“Definitely!” Anna said. She dipped her bottom in the tub water to get everything freshly wet and turned over on her knees to present her bottom to him. Jake put shaving cream along the inside of each bottom cheek. A few careful strokes of the razor later he was finished, and he stopped to admire his work on her beautiful body.“All done!” he announced.Anna sat back down in the tub. “Alright, your turn now. Up on the edge of the tub!”While shaving Anna, Jake was so focused on being careful that his misbehaving dick shrunk down to nearly normal. Spreading his legs and presenting himself to Anna, however, quickly brought it back to fully erect.“Thank you,” she said. “I was worried how I would do this properly if your penis wasn’t erect. Are you ready?”Jake nodded, and Anna started rubbing shaving cream into his pubic hair. Looking down he watched her beautiful face, completely focused on her task. Her breasts, so comforting to see, jiggled as she moved. Part of him was very present, relishing her touches and attention. Another part of him was so deep in thought it was almost like having an out of body experience. Anna was the one person he cared most about in the whole world. She was his closest friend, the person who most understood him. When he was away from her, he missed her. When he was with her, he felt utterly content. His place didn’t feel like home unless she was there too. This wasn’t mere physical lust, though there was plenty of that as well. He truly loved her. The trouble was he didn’t see a way to tell her this, without risking messing up what he already had. The thought of frightening her off, of not sharing this intimacy with her, was too horrible to consider.Seeing the way she touched him, though, so carefully and tenderly, it was hard to believe she didn’t have any sexual feelings for him.“There we go,” Anna said, waking him from his reverie. Jake looked down to see himself thoroughly hairless. He didn’t get time to really look before she turned him over to shave between his butt cheeks. A minute later she was finished. They rinsed off in the shower and stood next to each other in front of the mirror to admire the results.“We look fantastic. I love this!” Anna said.“You look amazing,” Jake said.“So do you!” Anna was striking poses in the mirror. “Oh, I almost forgot. We need to moisturize.” She dug in her drawer and pulled out a bottle of lotion. “It’s a very gentle lotion suitable for the whole body. Do you mind if I apply it?” Jake shook his head and Anna straightened the towel on the floor for him to lie down upon. Anna used both hands on him to gently massage lotion everywhere she had shaved, including the shaft of his rock-hard dick and his smooth ball sack. Unlike shaving, he was obviously capable of applying lotion to himself without danger. But if she wanted to touch him and be touched by him, he certainly wasn’t going to argue. He was surprised to find Anna spreading the lotion beyond the sha

Her Inverted Intimacy Challenge: Part 2

Play Episode Listen Later Mar 1, 2026

Platonic friends help with Intimate shaving, complicated by arousal.By darrenr. Listen to the ► Podcast at Steamy Stories.“There's one thing, though,” Anna said hesitantly. “I'm nervous about wielding a razor in such a tender place when I can't see very well down there. Would you, would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it's a big favor. It's no problem if you'd rather not.”Jake couldn't think of anything he wanted to do more than spend some quality time with Anna's vagina.“There’s one thing, though,” Anna said hesitantly. “I’m nervous about wielding a razor in such a tender place when I can’t see very well down there. Would you… would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it’s a big favor. It’s no problem if you’d rather not.”Jake couldn’t think of anything he wanted to do more than spend some quality time with Anna’s vagina.“It’s not that! I’m happy to help. It’s just, I’ve never shaved a, um, you know, a…”“Vulva?” Anna said with a smirk. “It’s okay to use the word. Anyway, neither have I! But you have the advantage of being able to see down there.”“Okay, fair point,” Jake said. “But it also means… well in order to do this, I’ll need to…” Anna raised her eyebrows waiting for him to finish.“I’ll be clean,” Anna said. “I’m going to shower first, of course.”Jake wasn’t expecting that. He shook his head. “Oh, no, I’m not concerned about that. I just mean I’ll need to… touch… you. There. You know, to shave you.”Anna frowned. “Yes, hmm, I see the difficulty now. You’ve got a friend sincerely asking for your help with her most private place, and you’re balking because even a clean vulva is, let’s face it, pretty gross.”“NO!” Jake said. “That’s not it at all!” Anna looked hurt. “I’m sorry, I don’t mean to yell. You’re completely misunderstanding me. I don’t think you’re gross in any way. I don’t think your… vulva is gross. At all. Not to be too corny about it, but I think your whole body is beautiful. Including your vag–, I mean, vulva.” Anna looked skeptical. Jake grimaced. “I’m nervous because… well, you’ve said our relationship isn’t sexual. I have to be honest with you. There’s no way I can touch your body… your vulva… and not be affected. Sexually.”Anna bit her lip and looked down, nodding. “I’m still figuring myself out. I think that experience with Andrew all those years ago affected me more than I realized. I don’t know what I want, or what I feel. I just know I feel safe with you.” She lifted her head to look him in the eye. “Do you think it’s possible to just pretend that it’s not sexual between us?”“Yes, I can do that,” Jake said. “Though my body might react differently.”Anna smiled in relief. “Then there’s nothing to worry about. Once the novelty wears off, you’ll realize what a tedious task you’ve volunteered for. Now come ON already.” Her face bright with happiness, she jumped up from the couch, pulling him by the hand to the bathroom. “I’m happy to help shave you in return, of course.”“That’s probably safest,” Jake said, trying to play it cool as he realized where she would be touching him.They showered together like normal. Anna got two fresh towels, spreading one on the floor of the bathroom and keeping the other folded as a pillow. She unwrapped a new razor and put it, along with a can of shaving cream, beside the towel. Lying down on her back, she stretched her legs out and spread them apart.“Do you think I should shave it all or keep a patch of hair?” she asked.Jake stood transfixed by the sight, contemplating her lovely bush. It was full and fluffy and beautiful, with light brown hair looking impossibly soft. Part of him didn’t want her to shave it, but only part of him.“We could definitely leave a patch of hair if you want. Though even if you start fully shaved it would grow back soon.”“Good point. Let’s just shave it all to start.” She reached for the can of shaving cream.“Wait,” Jake said. “When I’ve shaved my beard in the past it worked much better when I clipped the hair short first. Otherwise the razor gets clogged. I have some small mustache scissors, if you want?”“Good idea,” Anna agreed.Jake dug in his drawer until he found the scissors, and then turned to face her and froze. Could he really do this? He felt a bit faint at the thought of accidentally cutting her.“It’s okay, Jake. I know you’re going to be gentle. Go ahead and start!” She smiled nervously at him. “But please be careful.”Jake took a deep breath and knelt between her open legs. He’d never been this close, and his greedy eyes took in every detail. He looked up to her face, framed at this angle by her lovely breasts, and she gave him an encouraging nod. Taking a deep breath, Jake raised his empty hand toward her and gently grabbed a tuft of hair. It was even softer than it looked.“Your hair is beautiful. Are you sure you want me to cut it?”Anna rolled her eyes. “Yes, I’m sure. Let’s do it!”Slowly, Jake brought the scissors up and snipped off a chunk of hair. Realizing he needed a place to collect it, he spread out a tissue. Anna watched him intently, propped up on her elbows. Carefully he worked, gathering and snipping, gathering and snipping. He gently brushed the loose hairs off her after trimming everything above her cleft.“How are you doing?” Jake asked.“Thank you for being so gentle. I would be a nervous wreck doing this myself.”“It’s my pleasure,” Jake said automatically, before realizing how intensely true the statement was. Quickly, he added, “Are you ready for me to continue working down… lower?”“You mean on my vulva?” She laughed. “Please use the names of my body parts, you silly.”“Sorry, you’re right. Are you ready for me to trim your vulva?”“Absolutely, please go ahead,” Anna said with a smile, though he still saw nervousness in her eyes. She dropped back onto the towel pillow, her breathing only a little shaky.Looking at her tender folds, Jake felt his palms sweating and his heart beating furiously. Gently, so gently, he touched his finger to the top of her cleft and drew it down to tease out the hairs trapped within. It took a few tries to get the hairs pulled off the bit of her inner labia that sat flush with her cleft. Careful to hold the scissors so he could see exactly where they cut and terrified of hurting her, he trimmed down the length of her outer lips.Anna’s hips twitched a little. “That tickles!”“Sorry! I’m not trying to tickle you.”“I know, it’s just a bit of sensory overload. Can you please just pause for a minute and press your palm against my skin, just to give my nerves a minute to calm down?”“Skin? Don’t you mean ‘vulva’?” Jake said.Anna laughed. “Fair point! Yes, please put your hand over my vulva to calm it down.”Jake put his palm against her cleft and felt its warmth, relishing the intimacy. Anna sighed and took a few deep breaths. “Okay, I’m good. Keep going.”“Could you please spread your legs a bit wider, so I can trim at the base of your legs?”“Sure thing!” Anna said. She bent her knees, bringing her feet up to rest against the sides of Jake’s legs as he knelt before her. Her outer lips were pulled apart, revealing moist pinkness inside. Her lovely scent grew stronger in his nose. Jake felt his erection jump. At least she couldn’t see his obvious arousal now. A few more minutes of careful clipping and he was done. He couldn’t be sure, but her inner lips looked wetter than before. He gently brushed the loose hairs away from her cleft and onto the tissue. Remembering how it might tickle, he placed his palm over everything again to relieve her.“Would you like me to clip, um, further down?” Then, remembering her earlier admonishment, added, “Around your, uh, anus?”Anna giggled as she sat up, her cheeks a little red. Anna bit her lip. “I suppose getting embarrassed at this point is silly. Yes, please trim down there, too.” She turned over onto her knees and pushed her bottom into the air, giving Jake his first clear view between her cheeks. His heart yearned with affection for her, the desire to care for her, even her cute little butthole. Only a few wisps of hair grew back there, and he was soon finished clipping.“Okay, I think we’re ready to start shaving,” Jake said. “Does it make sense to do that in the tub with lots of warm water?”“Definitely the tub, but we’re not ready yet. I need to clip you!”“Oh!” Jake said, “I forgot.” It was true. He was disappointed to realize he was quite erect, and with no way to hide it.“Well come on, trade places with me!” Jake stood up, his massive erection hanging out in the open air. He lay on his back feeling exposed and embarrassed. Anna knelt between his legs, and then she picked up his feet and brought them against the sides of her legs, so he was spread apart like she had been. His straining dick pointed up at the wall somewhere above his head.“Sorry about that,” he said, gesturing toward his erection.“Don’t be!” Anna replied. “I think it actually works better to have the skin stretched out for this. See if you can keep it that way. Are you ready?”“Sure, go ahead,” Jake answered. He didn’t expect it to be difficult to stay hard with her breath gently tickling his shaft. Sitting up on his elbows, he watched her gently grab a tuft of hair and clip it. She looked up to make sure he was okay, and then resumed careful clipping. Her breasts hung down in a lovely way as she bent over him clipping. Jake put his head back on the towel pillow and tried to relax, her every touch thrilling him.“I didn’t realize hairs grew up the shaft of your penis.”“Yeah it’s pretty nasty.”“No, it’s not nasty,” Anna said. “Just interesting.” He felt her fingers gingerly wrap around his shaft. “Wow, the skin is so soft. It’s a weird contrast with the hardness beneath the skin.” Jake relished the feel of her hand on him and listened to the soft swish of the scissors.“Are you doing okay?” Anna asked. She paused and kept her hand still on his hardness, the same anti-tickling strategy he’d used on her. It felt so nice. Jake was far more than okay, though he didn’t dare say that.He tilted his head up to look at her. “Perfectly comfortable. Thank you for being so careful.” She smiled at him, and then returned to her trimming. Her tongue poked out between her lips the same way it did when she was focused on some electronics soldering project. Seeing her so dedicated to caring for him made his ridiculous dick strain against her fingers.“Everything is more dynamic down here than I thought,” Anna said.Jake sat up again to give her a questioning look.“I suppose it’s obvious. It just hadn’t occurred to me. Like, when you’re hard it’s not simply rigid. It’s constantly softening a bit and re-hardening. I can even feel your pulse! And your scrotum moves!”Jake laughed. “Yeah I guess it’s all pretty weird.”“Not weird! Interesting.”Anna moved her hand down to his scrotum, her fingers gently stroking it as she trimmed hairs.“Alright, flip over so I can trim your… um,” Anna giggled for a second before continuing. “Your anus.” Jake dreaded this, but he complied. “Oh, I like how this seam of skin connects to your scrotum. This is so interesting!” A few more minutes of trimming and then she was done.“Okay NOW we’re ready for the shaving part,” Anna said brightly.Jake righted himself and helped clean up the tissues of trimmed pubic hair. There was a lot of hair.“Wow, look at us all trimmed!” Anna said, looking back and forth between the two trimmed crotches. “It feels cooler already. This is going to be great!” She started the water running and moved the new razor and can of shaving cream to the edge of the tub. They climbed in together and sat facing each other in the rising water.“This is fun,” Anna said. “I know it must be weird and tedious for you. I really appreciate you doing this with me.”“Are you kidding?” Jake said. “I’m having fun too. It’s not tedious at all.”Anna pulled herself up to sit on the edge of the tub and handed Jake the can of shaving cream. Still sitting in the water, he scooted toward her as she spread her legs apart. Jake squirted some shaving cream into his hand.“Ready?” he asked. Anna nodded, but he could see that her smile was a bit forced. He didn’t blame her for being nervous. He knew he felt more than nervous, and was grateful his hands remained steady. Jake dabbed the cream on the clipped-short hairs above her cleft and massaged it in with circular motions of his fingertips. Then he carefully dragged the razor in downward strokes, with the grain of her hair, stretching her skin flat as needed. Rinsing the razor often, he made sure to avoid re-shaving the same patch of skin. Finally, he was done with her pubic mound and rinsed her with cupped handfuls of water.“Nicely done, Jake!” Anna said, stroking the smooth skin with her hand. “Very nicely done.”Jake smiled, feeling pleased with his work. “Are you ready for me to shave your vulva now?”“Yes please!” Anna replied, though he could tell her enthusiasm was trying to conceal her nervousness.Jake squirted more cream in his hand and dabbed it on either side of her cleft. With both hands he gently rubbed cream along the inside of her legs and along her outer lips. Glancing up to check on her, he saw her cheeks were flushed. Did his touches feel good to her, or was that simply terror? Anna gave him a reassuring smile. Jake tried to focus.Continuing the short downward strokes, Jake gently drew the razor along her outer lips. Terrified of hurting her, with his other hand he stretched the skin flat and pulled it away from her inner labia as he shaved. After several minutes of careful work, she was shaved as far down as he could work at this angle. He brought up cupped handfuls of water to rinse and carefully stroked her skin feeling for any spots he might have missed. After a few touch-up strokes, he felt satisfied.“How is that?” Jake asked, looking up to her face. Anna’s cheeks were even more flushed, and she bit her lower lip. She broke out into a big smile.“Wow, Jake, you did a great job!” She explored all the shaved places with her fingers. “It feels so strange.”“I didn’t do a perfect job,” Jake said. “I was afraid of giving you a razor burn, so I went for gentleness over thoroughness.”“Thank you for being so careful. The whole time I knew I was in safe hands.”“You’re beautiful,” Jake said softly, lost in thought staring at her smooth cleft. Then, catching himself, “I think it looks great! Want me to finish your, uh, anus?”“Definitely!” Anna said. She dipped her bottom in the tub water to get everything freshly wet and turned over on her knees to present her bottom to him. Jake put shaving cream along the inside of each bottom cheek. A few careful strokes of the razor later he was finished, and he stopped to admire his work on her beautiful body.“All done!” he announced.Anna sat back down in the tub. “Alright, your turn now. Up on the edge of the tub!”While shaving Anna, Jake was so focused on being careful that his misbehaving dick shrunk down to nearly normal. Spreading his legs and presenting himself to Anna, however, quickly brought it back to fully erect.“Thank you,” she said. “I was worried how I would do this properly if your penis wasn’t erect. Are you ready?”Jake nodded, and Anna started rubbing shaving cream into his pubic hair. Looking down he watched her beautiful face, completely focused on her task. Her breasts, so comforting to see, jiggled as she moved. Part of him was very present, relishing her touches and attention. Another part of him was so deep in thought it was almost like having an out of body experience. Anna was the one person he cared most about in the whole world. She was his closest friend, the person who most understood him. When he was away from her, he missed her. When he was with her, he felt utterly content. His place didn’t feel like home unless she was there too. This wasn’t mere physical lust, though there was plenty of that as well. He truly loved her. The trouble was he didn’t see a way to tell her this, without risking messing up what he already had. The thought of frightening her off, of not sharing this intimacy with her, was too horrible to consider.Seeing the way she touched him, though, so carefully and tenderly, it was hard to believe she didn’t have any sexual feelings for him.“There we go,” Anna said, waking him from his reverie. Jake looked down to see himself thoroughly hairless. He didn’t get time to really look before she turned him over to shave between his butt cheeks. A minute later she was finished. They rinsed off in the shower and stood next to each other in front of the mirror to admire the results.“We look fantastic. I love this!” Anna said.“You look amazing,” Jake said.“So do you!” Anna was striking poses in the mirror. “Oh, I almost forgot. We need to moisturize.” She dug in her drawer and pulled out a bottle of lotion. “It’s a very gentle lotion suitable for the whole body. Do you mind if I apply it?” Jake shook his head and Anna straightened the towel on the floor for him to lie down upon. Anna used both hands on him to gently massage lotion everywhere she had shaved, including the shaft of his rock-hard dick and his smooth ball sack. Unlike shaving, he was obviously capable of applying lotion to himself without danger. But if she wanted to touch him and be touched by him, he certainly wasn’t going to argue. He was surprised to find Anna spreading the lotion beyond the sha

Her Inverted Intimacy Challenge: Part 2

Play Episode Listen Later Mar 1, 2026

Platonic friends help with Intimate shaving, complicated by arousal.By darrenr. Listen to the ► Podcast at Steamy Stories.“There's one thing, though,” Anna said hesitantly. “I'm nervous about wielding a razor in such a tender place when I can't see very well down there. Would you, would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it's a big favor. It's no problem if you'd rather not.”Jake couldn't think of anything he wanted to do more than spend some quality time with Anna's vagina.“There’s one thing, though,” Anna said hesitantly. “I’m nervous about wielding a razor in such a tender place when I can’t see very well down there. Would you… would you be willing to help me?”Jake swallowed. “Help, um, help you shave?”Anna nodded. “I know it’s a big favor. It’s no problem if you’d rather not.”Jake couldn’t think of anything he wanted to do more than spend some quality time with Anna’s vagina.“It’s not that! I’m happy to help. It’s just, I’ve never shaved a, um, you know, a…”“Vulva?” Anna said with a smirk. “It’s okay to use the word. Anyway, neither have I! But you have the advantage of being able to see down there.”“Okay, fair point,” Jake said. “But it also means… well in order to do this, I’ll need to…” Anna raised her eyebrows waiting for him to finish.“I’ll be clean,” Anna said. “I’m going to shower first, of course.”Jake wasn’t expecting that. He shook his head. “Oh, no, I’m not concerned about that. I just mean I’ll need to… touch… you. There. You know, to shave you.”Anna frowned. “Yes, hmm, I see the difficulty now. You’ve got a friend sincerely asking for your help with her most private place, and you’re balking because even a clean vulva is, let’s face it, pretty gross.”“NO!” Jake said. “That’s not it at all!” Anna looked hurt. “I’m sorry, I don’t mean to yell. You’re completely misunderstanding me. I don’t think you’re gross in any way. I don’t think your… vulva is gross. At all. Not to be too corny about it, but I think your whole body is beautiful. Including your vag–, I mean, vulva.” Anna looked skeptical. Jake grimaced. “I’m nervous because… well, you’ve said our relationship isn’t sexual. I have to be honest with you. There’s no way I can touch your body… your vulva… and not be affected. Sexually.”Anna bit her lip and looked down, nodding. “I’m still figuring myself out. I think that experience with Andrew all those years ago affected me more than I realized. I don’t know what I want, or what I feel. I just know I feel safe with you.” She lifted her head to look him in the eye. “Do you think it’s possible to just pretend that it’s not sexual between us?”“Yes, I can do that,” Jake said. “Though my body might react differently.”Anna smiled in relief. “Then there’s nothing to worry about. Once the novelty wears off, you’ll realize what a tedious task you’ve volunteered for. Now come ON already.” Her face bright with happiness, she jumped up from the couch, pulling him by the hand to the bathroom. “I’m happy to help shave you in return, of course.”“That’s probably safest,” Jake said, trying to play it cool as he realized where she would be touching him.They showered together like normal. Anna got two fresh towels, spreading one on the floor of the bathroom and keeping the other folded as a pillow. She unwrapped a new razor and put it, along with a can of shaving cream, beside the towel. Lying down on her back, she stretched her legs out and spread them apart.“Do you think I should shave it all or keep a patch of hair?” she asked.Jake stood transfixed by the sight, contemplating her lovely bush. It was full and fluffy and beautiful, with light brown hair looking impossibly soft. Part of him didn’t want her to shave it, but only part of him.“We could definitely leave a patch of hair if you want. Though even if you start fully shaved it would grow back soon.”“Good point. Let’s just shave it all to start.” She reached for the can of shaving cream.“Wait,” Jake said. “When I’ve shaved my beard in the past it worked much better when I clipped the hair short first. Otherwise the razor gets clogged. I have some small mustache scissors, if you want?”“Good idea,” Anna agreed.Jake dug in his drawer until he found the scissors, and then turned to face her and froze. Could he really do this? He felt a bit faint at the thought of accidentally cutting her.“It’s okay, Jake. I know you’re going to be gentle. Go ahead and start!” She smiled nervously at him. “But please be careful.”Jake took a deep breath and knelt between her open legs. He’d never been this close, and his greedy eyes took in every detail. He looked up to her face, framed at this angle by her lovely breasts, and she gave him an encouraging nod. Taking a deep breath, Jake raised his empty hand toward her and gently grabbed a tuft of hair. It was even softer than it looked.“Your hair is beautiful. Are you sure you want me to cut it?”Anna rolled her eyes. “Yes, I’m sure. Let’s do it!”Slowly, Jake brought the scissors up and snipped off a chunk of hair. Realizing he needed a place to collect it, he spread out a tissue. Anna watched him intently, propped up on her elbows. Carefully he worked, gathering and snipping, gathering and snipping. He gently brushed the loose hairs off her after trimming everything above her cleft.“How are you doing?” Jake asked.“Thank you for being so gentle. I would be a nervous wreck doing this myself.”“It’s my pleasure,” Jake said automatically, before realizing how intensely true the statement was. Quickly, he added, “Are you ready for me to continue working down… lower?”“You mean on my vulva?” She laughed. “Please use the names of my body parts, you silly.”“Sorry, you’re right. Are you ready for me to trim your vulva?”“Absolutely, please go ahead,” Anna said with a smile, though he still saw nervousness in her eyes. She dropped back onto the towel pillow, her breathing only a little shaky.Looking at her tender folds, Jake felt his palms sweating and his heart beating furiously. Gently, so gently, he touched his finger to the top of her cleft and drew it down to tease out the hairs trapped within. It took a few tries to get the hairs pulled off the bit of her inner labia that sat flush with her cleft. Careful to hold the scissors so he could see exactly where they cut and terrified of hurting her, he trimmed down the length of her outer lips.Anna’s hips twitched a little. “That tickles!”“Sorry! I’m not trying to tickle you.”“I know, it’s just a bit of sensory overload. Can you please just pause for a minute and press your palm against my skin, just to give my nerves a minute to calm down?”“Skin? Don’t you mean ‘vulva’?” Jake said.Anna laughed. “Fair point! Yes, please put your hand over my vulva to calm it down.”Jake put his palm against her cleft and felt its warmth, relishing the intimacy. Anna sighed and took a few deep breaths. “Okay, I’m good. Keep going.”“Could you please spread your legs a bit wider, so I can trim at the base of your legs?”“Sure thing!” Anna said. She bent her knees, bringing her feet up to rest against the sides of Jake’s legs as he knelt before her. Her outer lips were pulled apart, revealing moist pinkness inside. Her lovely scent grew stronger in his nose. Jake felt his erection jump. At least she couldn’t see his obvious arousal now. A few more minutes of careful clipping and he was done. He couldn’t be sure, but her inner lips looked wetter than before. He gently brushed the loose hairs away from her cleft and onto the tissue. Remembering how it might tickle, he placed his palm over everything again to relieve her.“Would you like me to clip, um, further down?” Then, remembering her earlier admonishment, added, “Around your, uh, anus?”Anna giggled as she sat up, her cheeks a little red. Anna bit her lip. “I suppose getting embarrassed at this point is silly. Yes, please trim down there, too.” She turned over onto her knees and pushed her bottom into the air, giving Jake his first clear view between her cheeks. His heart yearned with affection for her, the desire to care for her, even her cute little butthole. Only a few wisps of hair grew back there, and he was soon finished clipping.“Okay, I think we’re ready to start shaving,” Jake said. “Does it make sense to do that in the tub with lots of warm water?”“Definitely the tub, but we’re not ready yet. I need to clip you!”“Oh!” Jake said, “I forgot.” It was true. He was disappointed to realize he was quite erect, and with no way to hide it.“Well come on, trade places with me!” Jake stood up, his massive erection hanging out in the open air. He lay on his back feeling exposed and embarrassed. Anna knelt between his legs, and then she picked up his feet and brought them against the sides of her legs, so he was spread apart like she had been. His straining dick pointed up at the wall somewhere above his head.“Sorry about that,” he said, gesturing toward his erection.“Don’t be!” Anna replied. “I think it actually works better to have the skin stretched out for this. See if you can keep it that way. Are you ready?”“Sure, go ahead,” Jake answered. He didn’t expect it to be difficult to stay hard with her breath gently tickling his shaft. Sitting up on his elbows, he watched her gently grab a tuft of hair and clip it. She looked up to make sure he was okay, and then resumed careful clipping. Her breasts hung down in a lovely way as she bent over him clipping. Jake put his head back on the towel pillow and tried to relax, her every touch thrilling him.“I didn’t realize hairs grew up the shaft of your penis.”“Yeah it’s pretty nasty.”“No, it’s not nasty,” Anna said. “Just interesting.” He felt her fingers gingerly wrap around his shaft. “Wow, the skin is so soft. It’s a weird contrast with the hardness beneath the skin.” Jake relished the feel of her hand on him and listened to the soft swish of the scissors.“Are you doing okay?” Anna asked. She paused and kept her hand still on his hardness, the same anti-tickling strategy he’d used on her. It felt so nice. Jake was far more than okay, though he didn’t dare say that.He tilted his head up to look at her. “Perfectly comfortable. Thank you for being so careful.” She smiled at him, and then returned to her trimming. Her tongue poked out between her lips the same way it did when she was focused on some electronics soldering project. Seeing her so dedicated to caring for him made his ridiculous dick strain against her fingers.“Everything is more dynamic down here than I thought,” Anna said.Jake sat up again to give her a questioning look.“I suppose it’s obvious. It just hadn’t occurred to me. Like, when you’re hard it’s not simply rigid. It’s constantly softening a bit and re-hardening. I can even feel your pulse! And your scrotum moves!”Jake laughed. “Yeah I guess it’s all pretty weird.”“Not weird! Interesting.”Anna moved her hand down to his scrotum, her fingers gently stroking it as she trimmed hairs.“Alright, flip over so I can trim your… um,” Anna giggled for a second before continuing. “Your anus.” Jake dreaded this, but he complied. “Oh, I like how this seam of skin connects to your scrotum. This is so interesting!” A few more minutes of trimming and then she was done.“Okay NOW we’re ready for the shaving part,” Anna said brightly.Jake righted himself and helped clean up the tissues of trimmed pubic hair. There was a lot of hair.“Wow, look at us all trimmed!” Anna said, looking back and forth between the two trimmed crotches. “It feels cooler already. This is going to be great!” She started the water running and moved the new razor and can of shaving cream to the edge of the tub. They climbed in together and sat facing each other in the rising water.“This is fun,” Anna said. “I know it must be weird and tedious for you. I really appreciate you doing this with me.”“Are you kidding?” Jake said. “I’m having fun too. It’s not tedious at all.”Anna pulled herself up to sit on the edge of the tub and handed Jake the can of shaving cream. Still sitting in the water, he scooted toward her as she spread her legs apart. Jake squirted some shaving cream into his hand.“Ready?” he asked. Anna nodded, but he could see that her smile was a bit forced. He didn’t blame her for being nervous. He knew he felt more than nervous, and was grateful his hands remained steady. Jake dabbed the cream on the clipped-short hairs above her cleft and massaged it in with circular motions of his fingertips. Then he carefully dragged the razor in downward strokes, with the grain of her hair, stretching her skin flat as needed. Rinsing the razor often, he made sure to avoid re-shaving the same patch of skin. Finally, he was done with her pubic mound and rinsed her with cupped handfuls of water.“Nicely done, Jake!” Anna said, stroking the smooth skin with her hand. “Very nicely done.”Jake smiled, feeling pleased with his work. “Are you ready for me to shave your vulva now?”“Yes please!” Anna replied, though he could tell her enthusiasm was trying to conceal her nervousness.Jake squirted more cream in his hand and dabbed it on either side of her cleft. With both hands he gently rubbed cream along the inside of her legs and along her outer lips. Glancing up to check on her, he saw her cheeks were flushed. Did his touches feel good to her, or was that simply terror? Anna gave him a reassuring smile. Jake tried to focus.Continuing the short downward strokes, Jake gently drew the razor along her outer lips. Terrified of hurting her, with his other hand he stretched the skin flat and pulled it away from her inner labia as he shaved. After several minutes of careful work, she was shaved as far down as he could work at this angle. He brought up cupped handfuls of water to rinse and carefully stroked her skin feeling for any spots he might have missed. After a few touch-up strokes, he felt satisfied.“How is that?” Jake asked, looking up to her face. Anna’s cheeks were even more flushed, and she bit her lower lip. She broke out into a big smile.“Wow, Jake, you did a great job!” She explored all the shaved places with her fingers. “It feels so strange.”“I didn’t do a perfect job,” Jake said. “I was afraid of giving you a razor burn, so I went for gentleness over thoroughness.”“Thank you for being so careful. The whole time I knew I was in safe hands.”“You’re beautiful,” Jake said softly, lost in thought staring at her smooth cleft. Then, catching himself, “I think it looks great! Want me to finish your, uh, anus?”“Definitely!” Anna said. She dipped her bottom in the tub water to get everything freshly wet and turned over on her knees to present her bottom to him. Jake put shaving cream along the inside of each bottom cheek. A few careful strokes of the razor later he was finished, and he stopped to admire his work on her beautiful body.“All done!” he announced.Anna sat back down in the tub. “Alright, your turn now. Up on the edge of the tub!”While shaving Anna, Jake was so focused on being careful that his misbehaving dick shrunk down to nearly normal. Spreading his legs and presenting himself to Anna, however, quickly brought it back to fully erect.“Thank you,” she said. “I was worried how I would do this properly if your penis wasn’t erect. Are you ready?”Jake nodded, and Anna started rubbing shaving cream into his pubic hair. Looking down he watched her beautiful face, completely focused on her task. Her breasts, so comforting to see, jiggled as she moved. Part of him was very present, relishing her touches and attention. Another part of him was so deep in thought it was almost like having an out of body experience. Anna was the one person he cared most about in the whole world. She was his closest friend, the person who most understood him. When he was away from her, he missed her. When he was with her, he felt utterly content. His place didn’t feel like home unless she was there too. This wasn’t mere physical lust, though there was plenty of that as well. He truly loved her. The trouble was he didn’t see a way to tell her this, without risking messing up what he already had. The thought of frightening her off, of not sharing this intimacy with her, was too horrible to consider.Seeing the way she touched him, though, so carefully and tenderly, it was hard to believe she didn’t have any sexual feelings for him.“There we go,” Anna said, waking him from his reverie. Jake looked down to see himself thoroughly hairless. He didn’t get time to really look before she turned him over to shave between his butt cheeks. A minute later she was finished. They rinsed off in the shower and stood next to each other in front of the mirror to admire the results.“We look fantastic. I love this!” Anna said.“You look amazing,” Jake said.“So do you!” Anna was striking poses in the mirror. “Oh, I almost forgot. We need to moisturize.” She dug in her drawer and pulled out a bottle of lotion. “It’s a very gentle lotion suitable for the whole body. Do you mind if I apply it?” Jake shook his head and Anna straightened the towel on the floor for him to lie down upon. Anna used both hands on him to gently massage lotion everywhere she had shaved, including the shaft of his rock-hard dick and his smooth ball sack. Unlike shaving, he was obviously capable of applying lotion to himself without danger. But if she wanted to touch him and be touched by him, he certainly wasn’t going to argue. He was surprised to find Anna spreading the lotion beyond the sha

Inverted World w/ Shane Cashman

Nephilim Death Squad

Play Episode Listen Later Feb 28, 2026 133:22 Transcription Available

Is the world upside down — or are we finally starting to see it clearly?In this episode of Nephilim Death Squad, Raven and TopLobsta sit down with journalist and cultural commentator Shane Cashman for a deep conversation about modern media, inverted narratives, cultural manipulation, and the strange psychological moment defining our era.From journalism and storytelling to propaganda, perception, and the growing distrust of institutions, the discussion explores how reality itself can feel inverted in an age of information overload. Shane shares insights from his work covering controversial stories, fringe communities, and the shifting boundaries between mainstream and alternative media.Blending humor, philosophy, and cultural analysis, this episode examines whether society is experiencing confusion — or awakening.

Her Inverted Intimacy Challenge: Part 1

Play Episode Listen Later Feb 28, 2026

How long can naked friends resist becoming lovers?By darrenr. Listen to the ► Podcast at Steamy Stories.“Breasts, yes. I want to show you my breasts,” Anna said, making a simple request that complicated everything.Jake instinctively glanced down at her chest, before wrenching his gaze back to her face. His mind raced in useless circles around a single thought: Danger!“But you have to promise to tell me if that would make you uncomfortable,” Anna said. “I can only ask you this favor because our friendship is both close and solidly non-romantic. I completely understand if my request is just too flippin' weird!”Jake had never been less comfortable in his life. This felt like a bad idea.He wanted it anyway.Feeling ashamed of himself, Jake forced himself to think. Anna wouldn't ask unless it was important to her. He didn't want to hurt her feelings, so he tried a joke. “Compared to eating the terrible chicken dinner you made last night, this sounds like a walk in the park.”Anna erupted in giggling. She was clearly nervous, but it was comforting to hear her infectious laugh. That, at least, felt normal.They met about a year ago, neighbors moving in on the same day. She had a kind face. If she wore makeup, it wasn't enough to notice. She was an inch taller, had brown eyes and long blonde hair–brilliantly shining blonde–always in a ponytail. Her face seemed to have only two states: stern concentration or an easy smile. She had a solid aspect to her figure but wasn't fat. Her tight jeans revealed strong legs and a substantial bottom that her height proportioned nicely. A baggy flannel shirt hid any details about her breasts.Although Jake tended to be shy, an endless conversation began during their second shared elevator trip. Her name was Aine, but she went by Anna. She liked hiking and tinkering with electronics. They both just moved into town and it was their first time living on their own. Anna did some kind of computer engineering work that sounded much cooler than the business analysis work he did. They both used Excel spreadsheets extensively for work and shared many of the same frustrations with its quirks. They liked a lot of the same video games and movies and had plenty to talk about.That first night they shared take-out at Jake's place, which was the start of Anna's habit of visiting constantly. Jake insisted on paying. To repay him, the next night Anna made dinner in his kitchen. Jake then reciprocated the following night. Neither of them was a very good cook, but it worked out. They ate dinner together nearly every day, alternating cooking and cleanup. Anna declared it was more efficient to share food between two people. She also decided Jake's pot, pan, and dish situation was better than hers, so they used his kitchen. Jake gave her the spare key to his apartment and she came and went as she pleased. He started to develop real feelings for her. This stopped when, after a week hanging out together, Anna mused on the merits of their relationship.“I'm glad we're neighbors,” Anna said that day. “We've only known each other a week, and yet I already feel like we've been friends for years.”“I feel the same way,” Jake had said.“Best of all,” she added in a moment burned into his memory, “Is we don't have a trace of romantic tension between us. We're free to just be friends without all that bullshit.”Jake let her comment pass without challenge. What else could he do? But it was a blow. All his romantic and erotic fantasies about her fizzled, impossible to sustain if she didn't feel the same. At least he did genuinely like her, mostly.The “mostly” came down to her presumptuousness. She saw that, obviously, it made sense for them to share Jake's kitchen. Obviously, it made sense for her to set up her electronics workbench in Jake's apartment, and hadn't even asked him. He didn't complain because he liked their dinner arrangement and liked seeing her build crazy electronics. She wasn't wrong in her actions; he just wished she'd ask first.Watching movies, playing video games, and discussing politics solidified their friendship. Jake was eventually able to suppress most of his unwelcome feelings about Anna. He tried his best to think of her as just a friend. A pal.Which made this request so upsetting. He was dismayed to find that his efforts over the past year had only hidden the shameful ember of carnal desire in his heart. Her words now rekindled it into a bright flame, unthinking and ravenous. He refused to let it burn this person he cared about.“Anna, wait.” Jake was surprised to hear the words coming out of his mouth. Concern returned to her face. “Are you sure about this? It's not that I don't want to see, you.”“Then why don't you shut up and let me show you?” Anna asked, laughing nervously.“Believe me, I'm wondering myself. I just, we've been neighbors for almost a year now, and I like to think we've become friends. However, I never got the sense you saw me as more than a friend, so this whole ‘I want you to see me naked' thing is a bit of a surprise. Not an unwelcome surprise, but, well, can you please spell it out for this dummy?”Anna looked down and sighed. “You're right, I owe you an explanation. Please, please be patient with me. This isn't easy.”“Deal,” Jake said in agreement. He leaned back on the couch and crossed his arms and legs in an exaggerated manner. “I'm extremely patient.”Anna took a deep breath. “When I was eighteen I had my first serious boyfriend, Andrew. We were making out, and I let him take my shirt and bra off. It was a mistake. He was a mistake. I don't know what I saw in him. The thing is, I have inverted nipples.” Anna turn away from Jake and began to shyly fidget. “He freaked out when he saw them. He didn't want to touch them anymore, didn't want to touch me. Looking back, I think he was just a nervous kid frightened by something he didn't understand. Still, it really hurt.”“Fucking hell, Andrew. What a massive asshole,” Jake said.Anna's face showed relief at his reaction. “Yes,” she agreed, “especially when he told his friends and started calling me ‘NN anna' for ‘No Nipple Anna.'”“No way!” Jake said. “What the fuck?”“High school can be rough, right? It's not even accurate. I have nipples, they just go in instead of out. I think the whole school eventually heard. Plenty of people 'accidentally' called me Nnanna, even a teacher once. I was devastated at the time, but I've tried to forget about him, about his reaction, about the taunting. I've dated a few guys over the years, though I've always ended it before things got, intimate. I've come to realize, on some level, I'm still ashamed of my body. I'm still afraid of a repeat of Andrew's reaction.”“That is some bullshit. No person should be ashamed of their body.”“Yes,” Anna agreed. “Intellectually, I know that. I've been telling myself for years. My trouble is the difference between knowing in my head and really feeling it in my heart. That's what I'm hoping you can help me with.”“Got it,” Jake said. “You want to show me your breasts, so I can NOT freak out.”“Exactly! Which sounds silly when you say it out loud. I know this is a weird favor to ask, I just, I feel safe with you.” Doubt returned to her face. “It's totally okay if you'd rather not do this. I don't want to guilt you into this.”“Anna, it's okay. Thank you for explaining. I understand, I think.”“Oh, come on, it's not a big deal,” Anna said, trying to sound casual. “Right?”Jake shook his head. “I disagree,” he said. “A friend sharing something deeply personal and fraught with shame, trusting me. It's a big deal.”Anna gazed into Jake's eyes, her breasts dominating his thoughts as they rose and fell with her breaths. He wondered if he saw more than friendship flickering in her eyes, but then it vanished.“Thank you,” she said. “Now that we've reached an understanding and decided on a course of action, we have another problem: I don't see how I can work up the courage to actually, um, do it.” Her voice got very quiet at the end as she looked down and chewed her lip. “It just seems impossibly weird and awkward to undress in front of you.” She gave his arm a gentle shove like she did when they played video games.Jake thought for a second.“Well I'm certainly not going to pressure you. But if you're set on doing this, then I have a suggestion: What if we both pretend you're fully clothed? I'll set up the video game. When you're ready, you come in dressed however you want, and we'll both just pretend everything is normal. We can play Mario Kart like we planned, all very normal and unremarkable.” Jake couldn't help smirking a little bit at this last sentence.Anna's face brightened. “I like that idea. That might work.”Jake stood up. “Off you go, then,” he pointed at his bedroom. “I'll just set up the game and you can join me when you're ready.” He faced the TV and grabbed the remote. “I hope you are prepared to get trounced,” he added.Anna departed for his bedroom. Jake's heart raced, and his hands trembled a bit. He tried some deep slow breaths. They didn't help much. He visualized the bedroom door behind him and the woman he expected to emerge any second.Jake was ashamed to feel an erection start at just the thought of seeing Anna's breasts. His friend was trusting him to help her! He had to master himself and come through for her. He had to.He heard Anna take a quiet step into the open doorway behind him. He dared not turn around.On an impulse he pulled his own shirt off and tossed it. While he was very aware his own skinny chest was completely unremarkable, he hoped this would make her a bit more comfortable.Then he did something he knew she hated. “I hope you don't mind, I'm just going to start the race. I'm choosing your character, yes, Bowser on the biggest car so you can't do anything but go in a straight line…”Anna's hand snatched the controller out of his as she dropped beside him on the couch.“Don't you dare!” she said, laughing.Jake kept his eyes locked on the TV screen, trying to act casual while his mind reeled at the bare breasts just visible at the corner of his eye. She had done it!Part of him wanted to turn and stare directly at the first bare breasts he'd met in person. A bigger part of him was simply proud of his friend's courage. She'd identified a source of needless shame and took steps to overcome it. Jake wanted to make this a positive experience for her.That didn't mean he didn't take in as much as he could without looking directly. In addition to taking off her shirt and bra, she had taken out her ponytail. She parted her hair on either side of her head, and let it fall down her front. Through this inadequate screen of hair he thrilled at an impression of pale roundness, and maybe a hint of pink?It helped to have the game to concentrate on, though his playing was shit. Anna was never one to sit still and just push buttons on the controller. She moved her whole body with each turn of the race car. He kept his gaze glued to the TV even though her constant movement tickled the outskirts of his vision mercilessly.After several races, Jake started to feel close to normal. His game-play was back up to the level of “respectable.” His erection calmed down. He still hadn't gotten a look at Anna's bare breasts sitting right next to him, but he also no longer had to struggle to keep his eyes locked forward. He felt relaxed and happy, having fun with his friend. More than happy, he felt buoyant. It was as if Anna's bare chest was a beacon radiating warmth, bathing his heart in contentment. Just knowing that she trusted him with this made him feel closer to her.When Anna won the next race, Jake decided to check on her. He put the controller down, tilted his head far back on the couch to make it clear he could only see the ceiling, and leaned in her direction with one hand to his mouth in a conspiratorial gesture. Whispering, he said, “How are you doing?”Anna mirrored his pose and whispered in response. “Really good, actually. How are you doing?”“Really good, too,” Jake said, afraid to reveal how much more than just 'good' he felt.Anna nodded slightly and then she sat up and resumed talking in a normal voice. “I'm going to get us glasses of water.” And with that she stood up and walked to the kitchen.Jake took in the sight of her bare back as she walked away from him. She was beautiful. He longed to touch her and hated himself for it. Momentarily, she would be walking back toward him, and he had to keep his eyes on the TV. He had to.She returned from the kitchen with two glasses of water. Instead of sitting she stood directly in front of him, blocking the TV, and held one out. Jake's efforts at gaze discipline went out the window as he was forced to look up at the glass, which she held at the exact elevation to be in line between his eyeballs and her breasts. Jake did his best to keep his eyes moving up to her face where he looked her in the eyes and said a hoarse “thank you” as he took the glass.Anna tilted her head far back to take drink. With her eyes toward the ceiling, Jake understood she was giving him permission to look.Jake's eyes widened as he took in the sight, and his composure left him. The rest of the room faded out of existence as his brain took in every detail.The slightly tan color of Anna's face and arms was thanks to the sun, for her bare shoulders and upper chest were paler. Her breasts were paler still and revealed a faint tracery of blue veins around her shapely contours. Her hair covered the promised inverted nipples, though he could see the edges of puffy pink areolas.On the one hand, this was just another part of his friend's body. His friend Anna happened to be a woman, women have breasts, and these were simply Anna's breasts. Up close like this, Jake could see the subtle details on her skin. The fine hairs, sprinkling of moles, and minor asymmetries stressed the reality of what he beheld, in contrast to the airbrushed breasts in porn. Intellectually, Jake knew in the big picture all breasts, all bodies, were ultimately unremarkable.On the other hand, Jake couldn't help feeling these particular breasts were magical beacons of beauty, acceptance, trust, and intimacy. Anna's breasts emanated waves of warmth that bathed his heart in joy and evoked feelings of affection and protectiveness. It pained him to think of all those years of being ashamed of her body, avoiding physical intimacy for fear of rejection.After an eternity of taking in this sight, Anna sat on the couch again. He fastened his eyes on the TV and tried to regain his composure.Jake felt a flash of pain on his arm as Anna playfully hit him with the back of her hand. “Come on, slowpoke, press 'A' so we can start the next race. I'm enjoying destroying you.”“Oops,” Jake said, resuming the game. And then, feeling daring, he added: “I don't know where my mind was.”It was hard to tell without turning his head, but he thought he saw her smile.They played a few more races until it was their usual bedtime for a work night.Anna stood up. “Well, we both have work tomorrow. Better call it a night.” She walked into Jake's bedroom and then returned dressed normally. The light in the room felt weaker without the shining warmth of her bare breasts. He fought to hide his disappointment.“G'night,” she said, walking to the door.Jake leaped up to meet her at the door. “Thanks for the fun evening,” he said. Then, his face reddening, “I mean the Mario Kart.”Anna laughed, her face blushing too. “Thank YOU!” Then, hesitating, “for everything.”When the door closed behind her, Jake's apartment felt cold, lonely, and dark.The next day at work, Jake had trouble getting anything done with visions of Anna's breasts dancing in his head. He missed the feeling of being with her when she was topless. But on his way home, a new worry arose: How awkward would it be when he saw her again tonight? There was no going back to how things had been before.Opening the door to his apartment, he heard Anna working in the kitchen.“Hey,” Jake called out.“Hey yourself,” Anna answered from the kitchen.Jake relaxed when he saw she was wearing a shirt, though not without a pang of disappointment. What had he expected? Idiot. Anna cut vegetables, wearing the circuit-board-print apron she liked.“Get the waters, I'm almost finished.”Jake tried to act normal but couldn't stop thinking about her breasts as he set the coffee table in front of the TV. Anna put down plates of chicken salad and sat beside him on the couch.Normally, at this point they would watch something on TV while they ate. The remote control was on the arm of the couch next to Anna, ignored.“How was work?” Anna asked.“Oh fine, pretty normal,” Jake lied. “You?”“Actually,” Anna said, “I had trouble focusing at work today.” She paused there, as if giving Jake an opportunity to say more.“To be honest,” Jake admitted, turning to look her in the eye, “I had the same problem.”“Was there something on your mind?” Anna asked.“Technically two things were on my mind,” Jake said.Anna burst out laughing. Relieved, Jake laughed too.“I want to thank you,” Anna said, “for being so patient with me last night. And kind. I was close to running out of the room in tears. You helped me keep it together.” She took his hand. “That was very kind of you. I feel like a burden of shame was lifted. Thank you.”Jake blushed.“What I hadn't expected, though…” Anna looked down. “What I hadn't expected was how much I enjoyed it.”Anna slowly raised her eyes to meet Jake's. Panic came rushing back. Did she want to do it again? Did Jake want that? Confused thoughts swirled in his head. Did he want to kiss Anna? Yes, but she didn't want that. Did he feel romantic thoughts about her? Yes, but she didn't want that either. Did he want to see her breasts again, despite all his misgivings? Yes. Most definitely yes.“Did you…” Anna was studying his face. “Did you enjoy it, too?”“YES!” Jake blurted out, not exactly playing it cool.Anna smiled. “Do you, do you mind if we do it again?”“I would love that,” Jake answered.Anna hesitated. “It made me feel better when you took your shirt off first.”Jake nearly tore his shirt in his rush to pull it off. Anna's eyes on his chest made his skin feel warm.After a moment of staring, Anna started to unbutton her shirt. Feeling emboldened by Anna's unguarded staring at him, Jake watched her fingers work. The anticipation was intense, and he felt a reckless swelling between his legs.“Excuse me,” Anna said sternly, “my eyes are up here.”Jake blanched and tore his gaze up at the ceiling, his heart pounding in panic and his dick shrinking in shame. Incoherent apologies spilled out of his mouth as he tried to repair the damage his eager eyes had done.“Whoa, whoa, it's okay, I was just joking!” Anna said quickly. “I've never seen anyone go so pale. Are you okay? Jake, you didn't do anything wrong. The whole point is for you to look at me.” She grabbed his shoulders. “Jake, please, I'm sorry, I was only trying to be funny.” She gently pulled on the back of his head until it was tilted down at her chest again. “Your respectful instincts are part of why I trust you. It's okay. I want you to look.”He watched her shirt rise and fall with each breath, and eventually his breathing matched hers. Anna released his head and resumed unbuttoning. She wasn't wearing a bra. After t

Her Inverted Intimacy Challenge: Part 1

Play Episode Listen Later Feb 28, 2026

How long can naked friends resist becoming lovers?By darrenr. Listen to the ► Podcast at Steamy Stories.“Breasts, yes. I want to show you my breasts,” Anna said, making a simple request that complicated everything.Jake instinctively glanced down at her chest, before wrenching his gaze back to her face. His mind raced in useless circles around a single thought: Danger!“But you have to promise to tell me if that would make you uncomfortable,” Anna said. “I can only ask you this favor because our friendship is both close and solidly non-romantic. I completely understand if my request is just too flippin' weird!”Jake had never been less comfortable in his life. This felt like a bad idea.He wanted it anyway.Feeling ashamed of himself, Jake forced himself to think. Anna wouldn't ask unless it was important to her. He didn't want to hurt her feelings, so he tried a joke. “Compared to eating the terrible chicken dinner you made last night, this sounds like a walk in the park.”Anna erupted in giggling. She was clearly nervous, but it was comforting to hear her infectious laugh. That, at least, felt normal.They met about a year ago, neighbors moving in on the same day. She had a kind face. If she wore makeup, it wasn't enough to notice. She was an inch taller, had brown eyes and long blonde hair–brilliantly shining blonde–always in a ponytail. Her face seemed to have only two states: stern concentration or an easy smile. She had a solid aspect to her figure but wasn't fat. Her tight jeans revealed strong legs and a substantial bottom that her height proportioned nicely. A baggy flannel shirt hid any details about her breasts.Although Jake tended to be shy, an endless conversation began during their second shared elevator trip. Her name was Aine, but she went by Anna. She liked hiking and tinkering with electronics. They both just moved into town and it was their first time living on their own. Anna did some kind of computer engineering work that sounded much cooler than the business analysis work he did. They both used Excel spreadsheets extensively for work and shared many of the same frustrations with its quirks. They liked a lot of the same video games and movies and had plenty to talk about.That first night they shared take-out at Jake's place, which was the start of Anna's habit of visiting constantly. Jake insisted on paying. To repay him, the next night Anna made dinner in his kitchen. Jake then reciprocated the following night. Neither of them was a very good cook, but it worked out. They ate dinner together nearly every day, alternating cooking and cleanup. Anna declared it was more efficient to share food between two people. She also decided Jake's pot, pan, and dish situation was better than hers, so they used his kitchen. Jake gave her the spare key to his apartment and she came and went as she pleased. He started to develop real feelings for her. This stopped when, after a week hanging out together, Anna mused on the merits of their relationship.“I'm glad we're neighbors,” Anna said that day. “We've only known each other a week, and yet I already feel like we've been friends for years.”“I feel the same way,” Jake had said.“Best of all,” she added in a moment burned into his memory, “Is we don't have a trace of romantic tension between us. We're free to just be friends without all that bullshit.”Jake let her comment pass without challenge. What else could he do? But it was a blow. All his romantic and erotic fantasies about her fizzled, impossible to sustain if she didn't feel the same. At least he did genuinely like her, mostly.The “mostly” came down to her presumptuousness. She saw that, obviously, it made sense for them to share Jake's kitchen. Obviously, it made sense for her to set up her electronics workbench in Jake's apartment, and hadn't even asked him. He didn't complain because he liked their dinner arrangement and liked seeing her build crazy electronics. She wasn't wrong in her actions; he just wished she'd ask first.Watching movies, playing video games, and discussing politics solidified their friendship. Jake was eventually able to suppress most of his unwelcome feelings about Anna. He tried his best to think of her as just a friend. A pal.Which made this request so upsetting. He was dismayed to find that his efforts over the past year had only hidden the shameful ember of carnal desire in his heart. Her words now rekindled it into a bright flame, unthinking and ravenous. He refused to let it burn this person he cared about.“Anna, wait.” Jake was surprised to hear the words coming out of his mouth. Concern returned to her face. “Are you sure about this? It's not that I don't want to see, you.”“Then why don't you shut up and let me show you?” Anna asked, laughing nervously.“Believe me, I'm wondering myself. I just, we've been neighbors for almost a year now, and I like to think we've become friends. However, I never got the sense you saw me as more than a friend, so this whole ‘I want you to see me naked' thing is a bit of a surprise. Not an unwelcome surprise, but, well, can you please spell it out for this dummy?”Anna looked down and sighed. “You're right, I owe you an explanation. Please, please be patient with me. This isn't easy.”“Deal,” Jake said in agreement. He leaned back on the couch and crossed his arms and legs in an exaggerated manner. “I'm extremely patient.”Anna took a deep breath. “When I was eighteen I had my first serious boyfriend, Andrew. We were making out, and I let him take my shirt and bra off. It was a mistake. He was a mistake. I don't know what I saw in him. The thing is, I have inverted nipples.” Anna turn away from Jake and began to shyly fidget. “He freaked out when he saw them. He didn't want to touch them anymore, didn't want to touch me. Looking back, I think he was just a nervous kid frightened by something he didn't understand. Still, it really hurt.”“Fucking hell, Andrew. What a massive asshole,” Jake said.Anna's face showed relief at his reaction. “Yes,” she agreed, “especially when he told his friends and started calling me ‘NN anna' for ‘No Nipple Anna.'”“No way!” Jake said. “What the fuck?”“High school can be rough, right? It's not even accurate. I have nipples, they just go in instead of out. I think the whole school eventually heard. Plenty of people 'accidentally' called me Nnanna, even a teacher once. I was devastated at the time, but I've tried to forget about him, about his reaction, about the taunting. I've dated a few guys over the years, though I've always ended it before things got, intimate. I've come to realize, on some level, I'm still ashamed of my body. I'm still afraid of a repeat of Andrew's reaction.”“That is some bullshit. No person should be ashamed of their body.”“Yes,” Anna agreed. “Intellectually, I know that. I've been telling myself for years. My trouble is the difference between knowing in my head and really feeling it in my heart. That's what I'm hoping you can help me with.”“Got it,” Jake said. “You want to show me your breasts, so I can NOT freak out.”“Exactly! Which sounds silly when you say it out loud. I know this is a weird favor to ask, I just, I feel safe with you.” Doubt returned to her face. “It's totally okay if you'd rather not do this. I don't want to guilt you into this.”“Anna, it's okay. Thank you for explaining. I understand, I think.”“Oh, come on, it's not a big deal,” Anna said, trying to sound casual. “Right?”Jake shook his head. “I disagree,” he said. “A friend sharing something deeply personal and fraught with shame, trusting me. It's a big deal.”Anna gazed into Jake's eyes, her breasts dominating his thoughts as they rose and fell with her breaths. He wondered if he saw more than friendship flickering in her eyes, but then it vanished.“Thank you,” she said. “Now that we've reached an understanding and decided on a course of action, we have another problem: I don't see how I can work up the courage to actually, um, do it.” Her voice got very quiet at the end as she looked down and chewed her lip. “It just seems impossibly weird and awkward to undress in front of you.” She gave his arm a gentle shove like she did when they played video games.Jake thought for a second.“Well I'm certainly not going to pressure you. But if you're set on doing this, then I have a suggestion: What if we both pretend you're fully clothed? I'll set up the video game. When you're ready, you come in dressed however you want, and we'll both just pretend everything is normal. We can play Mario Kart like we planned, all very normal and unremarkable.” Jake couldn't help smirking a little bit at this last sentence.Anna's face brightened. “I like that idea. That might work.”Jake stood up. “Off you go, then,” he pointed at his bedroom. “I'll just set up the game and you can join me when you're ready.” He faced the TV and grabbed the remote. “I hope you are prepared to get trounced,” he added.Anna departed for his bedroom. Jake's heart raced, and his hands trembled a bit. He tried some deep slow breaths. They didn't help much. He visualized the bedroom door behind him and the woman he expected to emerge any second.Jake was ashamed to feel an erection start at just the thought of seeing Anna's breasts. His friend was trusting him to help her! He had to master himself and come through for her. He had to.He heard Anna take a quiet step into the open doorway behind him. He dared not turn around.On an impulse he pulled his own shirt off and tossed it. While he was very aware his own skinny chest was completely unremarkable, he hoped this would make her a bit more comfortable.Then he did something he knew she hated. “I hope you don't mind, I'm just going to start the race. I'm choosing your character, yes, Bowser on the biggest car so you can't do anything but go in a straight line…”Anna's hand snatched the controller out of his as she dropped beside him on the couch.“Don't you dare!” she said, laughing.Jake kept his eyes locked on the TV screen, trying to act casual while his mind reeled at the bare breasts just visible at the corner of his eye. She had done it!Part of him wanted to turn and stare directly at the first bare breasts he'd met in person. A bigger part of him was simply proud of his friend's courage. She'd identified a source of needless shame and took steps to overcome it. Jake wanted to make this a positive experience for her.That didn't mean he didn't take in as much as he could without looking directly. In addition to taking off her shirt and bra, she had taken out her ponytail. She parted her hair on either side of her head, and let it fall down her front. Through this inadequate screen of hair he thrilled at an impression of pale roundness, and maybe a hint of pink?It helped to have the game to concentrate on, though his playing was shit. Anna was never one to sit still and just push buttons on the controller. She moved her whole body with each turn of the race car. He kept his gaze glued to the TV even though her constant movement tickled the outskirts of his vision mercilessly.After several races, Jake started to feel close to normal. His game-play was back up to the level of “respectable.” His erection calmed down. He still hadn't gotten a look at Anna's bare breasts sitting right next to him, but he also no longer had to struggle to keep his eyes locked forward. He felt relaxed and happy, having fun with his friend. More than happy, he felt buoyant. It was as if Anna's bare chest was a beacon radiating warmth, bathing his heart in contentment. Just knowing that she trusted him with this made him feel closer to her.When Anna won the next race, Jake decided to check on her. He put the controller down, tilted his head far back on the couch to make it clear he could only see the ceiling, and leaned in her direction with one hand to his mouth in a conspiratorial gesture. Whispering, he said, “How are you doing?”Anna mirrored his pose and whispered in response. “Really good, actually. How are you doing?”“Really good, too,” Jake said, afraid to reveal how much more than just 'good' he felt.Anna nodded slightly and then she sat up and resumed talking in a normal voice. “I'm going to get us glasses of water.” And with that she stood up and walked to the kitchen.Jake took in the sight of her bare back as she walked away from him. She was beautiful. He longed to touch her and hated himself for it. Momentarily, she would be walking back toward him, and he had to keep his eyes on the TV. He had to.She returned from the kitchen with two glasses of water. Instead of sitting she stood directly in front of him, blocking the TV, and held one out. Jake's efforts at gaze discipline went out the window as he was forced to look up at the glass, which she held at the exact elevation to be in line between his eyeballs and her breasts. Jake did his best to keep his eyes moving up to her face where he looked her in the eyes and said a hoarse “thank you” as he took the glass.Anna tilted her head far back to take drink. With her eyes toward the ceiling, Jake understood she was giving him permission to look.Jake's eyes widened as he took in the sight, and his composure left him. The rest of the room faded out of existence as his brain took in every detail.The slightly tan color of Anna's face and arms was thanks to the sun, for her bare shoulders and upper chest were paler. Her breasts were paler still and revealed a faint tracery of blue veins around her shapely contours. Her hair covered the promised inverted nipples, though he could see the edges of puffy pink areolas.On the one hand, this was just another part of his friend's body. His friend Anna happened to be a woman, women have breasts, and these were simply Anna's breasts. Up close like this, Jake could see the subtle details on her skin. The fine hairs, sprinkling of moles, and minor asymmetries stressed the reality of what he beheld, in contrast to the airbrushed breasts in porn. Intellectually, Jake knew in the big picture all breasts, all bodies, were ultimately unremarkable.On the other hand, Jake couldn't help feeling these particular breasts were magical beacons of beauty, acceptance, trust, and intimacy. Anna's breasts emanated waves of warmth that bathed his heart in joy and evoked feelings of affection and protectiveness. It pained him to think of all those years of being ashamed of her body, avoiding physical intimacy for fear of rejection.After an eternity of taking in this sight, Anna sat on the couch again. He fastened his eyes on the TV and tried to regain his composure.Jake felt a flash of pain on his arm as Anna playfully hit him with the back of her hand. “Come on, slowpoke, press 'A' so we can start the next race. I'm enjoying destroying you.”“Oops,” Jake said, resuming the game. And then, feeling daring, he added: “I don't know where my mind was.”It was hard to tell without turning his head, but he thought he saw her smile.They played a few more races until it was their usual bedtime for a work night.Anna stood up. “Well, we both have work tomorrow. Better call it a night.” She walked into Jake's bedroom and then returned dressed normally. The light in the room felt weaker without the shining warmth of her bare breasts. He fought to hide his disappointment.“G'night,” she said, walking to the door.Jake leaped up to meet her at the door. “Thanks for the fun evening,” he said. Then, his face reddening, “I mean the Mario Kart.”Anna laughed, her face blushing too. “Thank YOU!” Then, hesitating, “for everything.”When the door closed behind her, Jake's apartment felt cold, lonely, and dark.The next day at work, Jake had trouble getting anything done with visions of Anna's breasts dancing in his head. He missed the feeling of being with her when she was topless. But on his way home, a new worry arose: How awkward would it be when he saw her again tonight? There was no going back to how things had been before.Opening the door to his apartment, he heard Anna working in the kitchen.“Hey,” Jake called out.“Hey yourself,” Anna answered from the kitchen.Jake relaxed when he saw she was wearing a shirt, though not without a pang of disappointment. What had he expected? Idiot. Anna cut vegetables, wearing the circuit-board-print apron she liked.“Get the waters, I'm almost finished.”Jake tried to act normal but couldn't stop thinking about her breasts as he set the coffee table in front of the TV. Anna put down plates of chicken salad and sat beside him on the couch.Normally, at this point they would watch something on TV while they ate. The remote control was on the arm of the couch next to Anna, ignored.“How was work?” Anna asked.“Oh fine, pretty normal,” Jake lied. “You?”“Actually,” Anna said, “I had trouble focusing at work today.” She paused there, as if giving Jake an opportunity to say more.“To be honest,” Jake admitted, turning to look her in the eye, “I had the same problem.”“Was there something on your mind?” Anna asked.“Technically two things were on my mind,” Jake said.Anna burst out laughing. Relieved, Jake laughed too.“I want to thank you,” Anna said, “for being so patient with me last night. And kind. I was close to running out of the room in tears. You helped me keep it together.” She took his hand. “That was very kind of you. I feel like a burden of shame was lifted. Thank you.”Jake blushed.“What I hadn't expected, though…” Anna looked down. “What I hadn't expected was how much I enjoyed it.”Anna slowly raised her eyes to meet Jake's. Panic came rushing back. Did she want to do it again? Did Jake want that? Confused thoughts swirled in his head. Did he want to kiss Anna? Yes, but she didn't want that. Did he feel romantic thoughts about her? Yes, but she didn't want that either. Did he want to see her breasts again, despite all his misgivings? Yes. Most definitely yes.“Did you…” Anna was studying his face. “Did you enjoy it, too?”“YES!” Jake blurted out, not exactly playing it cool.Anna smiled. “Do you, do you mind if we do it again?”“I would love that,” Jake answered.Anna hesitated. “It made me feel better when you took your shirt off first.”Jake nearly tore his shirt in his rush to pull it off. Anna's eyes on his chest made his skin feel warm.After a moment of staring, Anna started to unbutton her shirt. Feeling emboldened by Anna's unguarded staring at him, Jake watched her fingers work. The anticipation was intense, and he felt a reckless swelling between his legs.“Excuse me,” Anna said sternly, “my eyes are up here.”Jake blanched and tore his gaze up at the ceiling, his heart pounding in panic and his dick shrinking in shame. Incoherent apologies spilled out of his mouth as he tried to repair the damage his eager eyes had done.“Whoa, whoa, it's okay, I was just joking!” Anna said quickly. “I've never seen anyone go so pale. Are you okay? Jake, you didn't do anything wrong. The whole point is for you to look at me.” She grabbed his shoulders. “Jake, please, I'm sorry, I was only trying to be funny.” She gently pulled on the back of his head until it was tilted down at her chest again. “Your respectful instincts are part of why I trust you. It's okay. I want you to look.”He watched her shirt rise and fall with each breath, and eventually his breathing matched hers. Anna released his head and resumed unbuttoning. She wasn't wearing a bra. After t

Her Inverted Intimacy Challenge: Part 1

Play Episode Listen Later Feb 28, 2026

How long can naked friends resist becoming lovers?By darrenr. Listen to the ► Podcast at Steamy Stories.“Breasts, yes. I want to show you my breasts,” Anna said, making a simple request that complicated everything.Jake instinctively glanced down at her chest, before wrenching his gaze back to her face. His mind raced in useless circles around a single thought: Danger!“But you have to promise to tell me if that would make you uncomfortable,” Anna said. “I can only ask you this favor because our friendship is both close and solidly non-romantic. I completely understand if my request is just too flippin' weird!”Jake had never been less comfortable in his life. This felt like a bad idea.He wanted it anyway.Feeling ashamed of himself, Jake forced himself to think. Anna wouldn't ask unless it was important to her. He didn't want to hurt her feelings, so he tried a joke. “Compared to eating the terrible chicken dinner you made last night, this sounds like a walk in the park.”Anna erupted in giggling. She was clearly nervous, but it was comforting to hear her infectious laugh. That, at least, felt normal.They met about a year ago, neighbors moving in on the same day. She had a kind face. If she wore makeup, it wasn't enough to notice. She was an inch taller, had brown eyes and long blonde hair–brilliantly shining blonde–always in a ponytail. Her face seemed to have only two states: stern concentration or an easy smile. She had a solid aspect to her figure but wasn't fat. Her tight jeans revealed strong legs and a substantial bottom that her height proportioned nicely. A baggy flannel shirt hid any details about her breasts.Although Jake tended to be shy, an endless conversation began during their second shared elevator trip. Her name was Aine, but she went by Anna. She liked hiking and tinkering with electronics. They both just moved into town and it was their first time living on their own. Anna did some kind of computer engineering work that sounded much cooler than the business analysis work he did. They both used Excel spreadsheets extensively for work and shared many of the same frustrations with its quirks. They liked a lot of the same video games and movies and had plenty to talk about.That first night they shared take-out at Jake's place, which was the start of Anna's habit of visiting constantly. Jake insisted on paying. To repay him, the next night Anna made dinner in his kitchen. Jake then reciprocated the following night. Neither of them was a very good cook, but it worked out. They ate dinner together nearly every day, alternating cooking and cleanup. Anna declared it was more efficient to share food between two people. She also decided Jake's pot, pan, and dish situation was better than hers, so they used his kitchen. Jake gave her the spare key to his apartment and she came and went as she pleased. He started to develop real feelings for her. This stopped when, after a week hanging out together, Anna mused on the merits of their relationship.“I'm glad we're neighbors,” Anna said that day. “We've only known each other a week, and yet I already feel like we've been friends for years.”“I feel the same way,” Jake had said.“Best of all,” she added in a moment burned into his memory, “Is we don't have a trace of romantic tension between us. We're free to just be friends without all that bullshit.”Jake let her comment pass without challenge. What else could he do? But it was a blow. All his romantic and erotic fantasies about her fizzled, impossible to sustain if she didn't feel the same. At least he did genuinely like her, mostly.The “mostly” came down to her presumptuousness. She saw that, obviously, it made sense for them to share Jake's kitchen. Obviously, it made sense for her to set up her electronics workbench in Jake's apartment, and hadn't even asked him. He didn't complain because he liked their dinner arrangement and liked seeing her build crazy electronics. She wasn't wrong in her actions; he just wished she'd ask first.Watching movies, playing video games, and discussing politics solidified their friendship. Jake was eventually able to suppress most of his unwelcome feelings about Anna. He tried his best to think of her as just a friend. A pal.Which made this request so upsetting. He was dismayed to find that his efforts over the past year had only hidden the shameful ember of carnal desire in his heart. Her words now rekindled it into a bright flame, unthinking and ravenous. He refused to let it burn this person he cared about.“Anna, wait.” Jake was surprised to hear the words coming out of his mouth. Concern returned to her face. “Are you sure about this? It's not that I don't want to see, you.”“Then why don't you shut up and let me show you?” Anna asked, laughing nervously.“Believe me, I'm wondering myself. I just, we've been neighbors for almost a year now, and I like to think we've become friends. However, I never got the sense you saw me as more than a friend, so this whole ‘I want you to see me naked' thing is a bit of a surprise. Not an unwelcome surprise, but, well, can you please spell it out for this dummy?”Anna looked down and sighed. “You're right, I owe you an explanation. Please, please be patient with me. This isn't easy.”“Deal,” Jake said in agreement. He leaned back on the couch and crossed his arms and legs in an exaggerated manner. “I'm extremely patient.”Anna took a deep breath. “When I was eighteen I had my first serious boyfriend, Andrew. We were making out, and I let him take my shirt and bra off. It was a mistake. He was a mistake. I don't know what I saw in him. The thing is, I have inverted nipples.” Anna turn away from Jake and began to shyly fidget. “He freaked out when he saw them. He didn't want to touch them anymore, didn't want to touch me. Looking back, I think he was just a nervous kid frightened by something he didn't understand. Still, it really hurt.”“Fucking hell, Andrew. What a massive asshole,” Jake said.Anna's face showed relief at his reaction. “Yes,” she agreed, “especially when he told his friends and started calling me ‘NN anna' for ‘No Nipple Anna.'”“No way!” Jake said. “What the fuck?”“High school can be rough, right? It's not even accurate. I have nipples, they just go in instead of out. I think the whole school eventually heard. Plenty of people 'accidentally' called me Nnanna, even a teacher once. I was devastated at the time, but I've tried to forget about him, about his reaction, about the taunting. I've dated a few guys over the years, though I've always ended it before things got, intimate. I've come to realize, on some level, I'm still ashamed of my body. I'm still afraid of a repeat of Andrew's reaction.”“That is some bullshit. No person should be ashamed of their body.”“Yes,” Anna agreed. “Intellectually, I know that. I've been telling myself for years. My trouble is the difference between knowing in my head and really feeling it in my heart. That's what I'm hoping you can help me with.”“Got it,” Jake said. “You want to show me your breasts, so I can NOT freak out.”“Exactly! Which sounds silly when you say it out loud. I know this is a weird favor to ask, I just, I feel safe with you.” Doubt returned to her face. “It's totally okay if you'd rather not do this. I don't want to guilt you into this.”“Anna, it's okay. Thank you for explaining. I understand, I think.”“Oh, come on, it's not a big deal,” Anna said, trying to sound casual. “Right?”Jake shook his head. “I disagree,” he said. “A friend sharing something deeply personal and fraught with shame, trusting me. It's a big deal.”Anna gazed into Jake's eyes, her breasts dominating his thoughts as they rose and fell with her breaths. He wondered if he saw more than friendship flickering in her eyes, but then it vanished.“Thank you,” she said. “Now that we've reached an understanding and decided on a course of action, we have another problem: I don't see how I can work up the courage to actually, um, do it.” Her voice got very quiet at the end as she looked down and chewed her lip. “It just seems impossibly weird and awkward to undress in front of you.” She gave his arm a gentle shove like she did when they played video games.Jake thought for a second.“Well I'm certainly not going to pressure you. But if you're set on doing this, then I have a suggestion: What if we both pretend you're fully clothed? I'll set up the video game. When you're ready, you come in dressed however you want, and we'll both just pretend everything is normal. We can play Mario Kart like we planned, all very normal and unremarkable.” Jake couldn't help smirking a little bit at this last sentence.Anna's face brightened. “I like that idea. That might work.”Jake stood up. “Off you go, then,” he pointed at his bedroom. “I'll just set up the game and you can join me when you're ready.” He faced the TV and grabbed the remote. “I hope you are prepared to get trounced,” he added.Anna departed for his bedroom. Jake's heart raced, and his hands trembled a bit. He tried some deep slow breaths. They didn't help much. He visualized the bedroom door behind him and the woman he expected to emerge any second.Jake was ashamed to feel an erection start at just the thought of seeing Anna's breasts. His friend was trusting him to help her! He had to master himself and come through for her. He had to.He heard Anna take a quiet step into the open doorway behind him. He dared not turn around.On an impulse he pulled his own shirt off and tossed it. While he was very aware his own skinny chest was completely unremarkable, he hoped this would make her a bit more comfortable.Then he did something he knew she hated. “I hope you don't mind, I'm just going to start the race. I'm choosing your character, yes, Bowser on the biggest car so you can't do anything but go in a straight line…”Anna's hand snatched the controller out of his as she dropped beside him on the couch.“Don't you dare!” she said, laughing.Jake kept his eyes locked on the TV screen, trying to act casual while his mind reeled at the bare breasts just visible at the corner of his eye. She had done it!Part of him wanted to turn and stare directly at the first bare breasts he'd met in person. A bigger part of him was simply proud of his friend's courage. She'd identified a source of needless shame and took steps to overcome it. Jake wanted to make this a positive experience for her.That didn't mean he didn't take in as much as he could without looking directly. In addition to taking off her shirt and bra, she had taken out her ponytail. She parted her hair on either side of her head, and let it fall down her front. Through this inadequate screen of hair he thrilled at an impression of pale roundness, and maybe a hint of pink?It helped to have the game to concentrate on, though his playing was shit. Anna was never one to sit still and just push buttons on the controller. She moved her whole body with each turn of the race car. He kept his gaze glued to the TV even though her constant movement tickled the outskirts of his vision mercilessly.After several races, Jake started to feel close to normal. His game-play was back up to the level of “respectable.” His erection calmed down. He still hadn't gotten a look at Anna's bare breasts sitting right next to him, but he also no longer had to struggle to keep his eyes locked forward. He felt relaxed and happy, having fun with his friend. More than happy, he felt buoyant. It was as if Anna's bare chest was a beacon radiating warmth, bathing his heart in contentment. Just knowing that she trusted him with this made him feel closer to her.When Anna won the next race, Jake decided to check on her. He put the controller down, tilted his head far back on the couch to make it clear he could only see the ceiling, and leaned in her direction with one hand to his mouth in a conspiratorial gesture. Whispering, he said, “How are you doing?”Anna mirrored his pose and whispered in response. “Really good, actually. How are you doing?”“Really good, too,” Jake said, afraid to reveal how much more than just 'good' he felt.Anna nodded slightly and then she sat up and resumed talking in a normal voice. “I'm going to get us glasses of water.” And with that she stood up and walked to the kitchen.Jake took in the sight of her bare back as she walked away from him. She was beautiful. He longed to touch her and hated himself for it. Momentarily, she would be walking back toward him, and he had to keep his eyes on the TV. He had to.She returned from the kitchen with two glasses of water. Instead of sitting she stood directly in front of him, blocking the TV, and held one out. Jake's efforts at gaze discipline went out the window as he was forced to look up at the glass, which she held at the exact elevation to be in line between his eyeballs and her breasts. Jake did his best to keep his eyes moving up to her face where he looked her in the eyes and said a hoarse “thank you” as he took the glass.Anna tilted her head far back to take drink. With her eyes toward the ceiling, Jake understood she was giving him permission to look.Jake's eyes widened as he took in the sight, and his composure left him. The rest of the room faded out of existence as his brain took in every detail.The slightly tan color of Anna's face and arms was thanks to the sun, for her bare shoulders and upper chest were paler. Her breasts were paler still and revealed a faint tracery of blue veins around her shapely contours. Her hair covered the promised inverted nipples, though he could see the edges of puffy pink areolas.On the one hand, this was just another part of his friend's body. His friend Anna happened to be a woman, women have breasts, and these were simply Anna's breasts. Up close like this, Jake could see the subtle details on her skin. The fine hairs, sprinkling of moles, and minor asymmetries stressed the reality of what he beheld, in contrast to the airbrushed breasts in porn. Intellectually, Jake knew in the big picture all breasts, all bodies, were ultimately unremarkable.On the other hand, Jake couldn't help feeling these particular breasts were magical beacons of beauty, acceptance, trust, and intimacy. Anna's breasts emanated waves of warmth that bathed his heart in joy and evoked feelings of affection and protectiveness. It pained him to think of all those years of being ashamed of her body, avoiding physical intimacy for fear of rejection.After an eternity of taking in this sight, Anna sat on the couch again. He fastened his eyes on the TV and tried to regain his composure.Jake felt a flash of pain on his arm as Anna playfully hit him with the back of her hand. “Come on, slowpoke, press 'A' so we can start the next race. I'm enjoying destroying you.”“Oops,” Jake said, resuming the game. And then, feeling daring, he added: “I don't know where my mind was.”It was hard to tell without turning his head, but he thought he saw her smile.They played a few more races until it was their usual bedtime for a work night.Anna stood up. “Well, we both have work tomorrow. Better call it a night.” She walked into Jake's bedroom and then returned dressed normally. The light in the room felt weaker without the shining warmth of her bare breasts. He fought to hide his disappointment.“G'night,” she said, walking to the door.Jake leaped up to meet her at the door. “Thanks for the fun evening,” he said. Then, his face reddening, “I mean the Mario Kart.”Anna laughed, her face blushing too. “Thank YOU!” Then, hesitating, “for everything.”When the door closed behind her, Jake's apartment felt cold, lonely, and dark.The next day at work, Jake had trouble getting anything done with visions of Anna's breasts dancing in his head. He missed the feeling of being with her when she was topless. But on his way home, a new worry arose: How awkward would it be when he saw her again tonight? There was no going back to how things had been before.Opening the door to his apartment, he heard Anna working in the kitchen.“Hey,” Jake called out.“Hey yourself,” Anna answered from the kitchen.Jake relaxed when he saw she was wearing a shirt, though not without a pang of disappointment. What had he expected? Idiot. Anna cut vegetables, wearing the circuit-board-print apron she liked.“Get the waters, I'm almost finished.”Jake tried to act normal but couldn't stop thinking about her breasts as he set the coffee table in front of the TV. Anna put down plates of chicken salad and sat beside him on the couch.Normally, at this point they would watch something on TV while they ate. The remote control was on the arm of the couch next to Anna, ignored.“How was work?” Anna asked.“Oh fine, pretty normal,” Jake lied. “You?”“Actually,” Anna said, “I had trouble focusing at work today.” She paused there, as if giving Jake an opportunity to say more.“To be honest,” Jake admitted, turning to look her in the eye, “I had the same problem.”“Was there something on your mind?” Anna asked.“Technically two things were on my mind,” Jake said.Anna burst out laughing. Relieved, Jake laughed too.“I want to thank you,” Anna said, “for being so patient with me last night. And kind. I was close to running out of the room in tears. You helped me keep it together.” She took his hand. “That was very kind of you. I feel like a burden of shame was lifted. Thank you.”Jake blushed.“What I hadn't expected, though…” Anna looked down. “What I hadn't expected was how much I enjoyed it.”Anna slowly raised her eyes to meet Jake's. Panic came rushing back. Did she want to do it again? Did Jake want that? Confused thoughts swirled in his head. Did he want to kiss Anna? Yes, but she didn't want that. Did he feel romantic thoughts about her? Yes, but she didn't want that either. Did he want to see her breasts again, despite all his misgivings? Yes. Most definitely yes.“Did you…” Anna was studying his face. “Did you enjoy it, too?”“YES!” Jake blurted out, not exactly playing it cool.Anna smiled. “Do you, do you mind if we do it again?”“I would love that,” Jake answered.Anna hesitated. “It made me feel better when you took your shirt off first.”Jake nearly tore his shirt in his rush to pull it off. Anna's eyes on his chest made his skin feel warm.After a moment of staring, Anna started to unbutton her shirt. Feeling emboldened by Anna's unguarded staring at him, Jake watched her fingers work. The anticipation was intense, and he felt a reckless swelling between his legs.“Excuse me,” Anna said sternly, “my eyes are up here.”Jake blanched and tore his gaze up at the ceiling, his heart pounding in panic and his dick shrinking in shame. Incoherent apologies spilled out of his mouth as he tried to repair the damage his eager eyes had done.“Whoa, whoa, it's okay, I was just joking!” Anna said quickly. “I've never seen anyone go so pale. Are you okay? Jake, you didn't do anything wrong. The whole point is for you to look at me.” She grabbed his shoulders. “Jake, please, I'm sorry, I was only trying to be funny.” She gently pulled on the back of his head until it was tilted down at her chest again. “Your respectful instincts are part of why I trust you. It's okay. I want you to look.”He watched her shirt rise and fall with each breath, and eventually his breathing matched hers. Anna released his head and resumed unbuttoning. She wasn't wearing a bra. After t

Her Inverted Intimacy Challenge: Part 1