Jennifer's Tale: My Life as a Crossdresser

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If you're a crossdresser please join me as I journey through my life - my thoughts, feelings, experiences and more - as I try to figure out why I'm this way, why I'm okay with who I am and why I enjoy spending time as Jennifer!

Jennifer


    • Jun 16, 2025 LATEST EPISODE
    • weekly NEW EPISODES
    • 11m AVG DURATION
    • 101 EPISODES


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    Latest episodes from Jennifer's Tale: My Life as a Crossdresser

    Episode 101 Finding Your Tribe

    Play Episode Listen Later Jun 16, 2025 10:14


    Whether you're a gamer, sci-fi fan or a crossdresser, finding others like yourself makes you feel better about who you are. Hear how I found my tribes throughout my life and what you can do to find yours!

    Episode 100 Sex and the Single/Married Crossdresser

    Play Episode Listen Later Jun 9, 2025 11:34


    Time to celebrate! In this anniversary episode I break the barrier and chat about crossdressers' sex lives - from what they say they like to their secret desires.

    Episode 99 Don't Be Afraid of Change

    Play Episode Listen Later Jun 2, 2025 10:37


    Over the years you may have worked hard to develop your look. But should you stop experimenting with your appearance? In this episode I talk about why it's a good thing to try new outfits, new makeup techniques and even new hair!

    Episode 98 Different Shapes and Sizes

    Play Episode Listen Later May 26, 2025 12:38


    If you pay attention, you will notice that women come in all shapes and sizes. You may think you need padding, cinchers and forms in order to make you look feminine. But is that really true?

    Episode 97 Oops!

    Play Episode Listen Later May 19, 2025 16:41


    Have you ever accidentally left out a pair of pantyhose after you've dressed? Maybe posted a pic of your femme self on your male Facebook page? Here are some stories of times I slipped up or was found out and what happened because of it!

    Episode 96 Don't Embarrass Me

    Play Episode Listen Later May 12, 2025 13:23


    One of the greatest fears a spouse or significant other of a crossdresser has is someone finding out who they are in real life. They love you but don't want to be embarrassed by your crossdressing. In this episode I discuss this topic and what you can do to help avoid these situations.

    Episode 95 Let's Be Casual

    Play Episode Listen Later May 5, 2025 10:19


    We all enjoy dressing up and looking sexy in sparkly dresses, short skirts and dazzling outfits. But many times we are better served by toning things down. It's time to discuss how you can dress "casual" and still feel sexy and feminine in this episode.

    Episode 94 Julie Does It Again!

    Play Episode Listen Later Apr 28, 2025 13:57


    I told Julie, the friendly lady at my local coffee shop, about Jennifer and wanted to stop by and have her meet me in person. What happened that day was wonderful and almost magical! Hear what happened and how there are caring people out there for us to meet in this episode.

    Episode 93 How Much is Too Much?

    Play Episode Listen Later Apr 21, 2025 13:09


    Can you have too much of a good thing? Can dressing as your femme self harm your marriage or relationship? I discuss the trials and tribulations of the fine line between success and excess in this episode.

    Episode 92 Another Jennifer Day

    Play Episode Listen Later Apr 14, 2025 12:18


    A day off means another Jennifer Day! Hear about my trip out and about - including a stop at my favorite coffee shop and possibly being figured out...

    Episode 91 Dealing With the Negative

    Play Episode Listen Later Apr 7, 2025 10:12


    How do you deal with a negative interaction or comment when you're out as your femme self? In this episode I discuss this matter and share my thoughts and tips on how to handle such a situation.

    Episode 90 A Little Spicy

    Play Episode Listen Later Mar 31, 2025 15:42


    In honor of Valentine's Day, here's a story of a first-time meeting I had with a lovely gentleman that proved to be a little spicy!

    Episode 89 Lack of Support (And I Don't Mean a Bra)

    Play Episode Listen Later Mar 24, 2025 11:35


    For many crossdressers, not having family or friends to share their secret with can be an issue. It's hard to hold in something so special that some may see as bad. In this episode I talk about what you can do to find that support we all need to make it through life.

    Episode 88 An Admiring Glance

    Play Episode Listen Later Mar 17, 2025 14:23


    Want to know how easy it can be to have someone make you feel amazing? Hear how I had a wonderful Jennifer Day and how one little thing made me feel validated and special.

    Episode 87 What's in a Name?

    Play Episode Listen Later Mar 10, 2025 10:59


    For some crossdressers choosing your feminine name is an easy task. For others it takes time and thought to capture who you are. Hear how I chose my feminine name here!

    Episode 86 Julie the Barista

    Play Episode Listen Later Mar 3, 2025 12:19


    It was a chilly day out but that didn't stop me! Hear about how I spent the morning recently as Jennifer - including going to my local coffee shop (which may not have been the best idea...)

    Episode 85 Dressing Around My Wife

    Play Episode Listen Later Feb 24, 2025 18:51


    A listener asked me "What's it like to dress around your wife?" In this episode, I talk about the history of my crossdressing and my wife - from telling her my secret and how she reacted to seeing Jennifer for the first time to how things are today.

    Episode 84 To Tuck Or Not to Tuck

    Play Episode Listen Later Feb 17, 2025 10:58


    It's a question every crossdresser has and a question everyone asks a crossdresser... Do you tuck? Where does "it" go? In this episode I answer this from my perspective.

    Episode 83 Lunch With a Friend

    Play Episode Listen Later Feb 10, 2025 9:01


    It may only be 14 degrees out but that's not stopping me from having a Jen Day! Here's the story of how I had lunch with a friend and the lesson that I, and maybe you, can learn from it.

    Episode 82 I Have Questions!

    Play Episode Listen Later Feb 3, 2025 12:53


    Many girls ask me for advice and have questions. In this episode I ask questions of my own in hopes of getting answers from you out there!

    Episode 81 What the Critics Say

    Play Episode Listen Later Jan 27, 2025 14:18


    Four years ago I fully accepted my crossdressing and started sharing this part of myself with friends and family. Here are some of the comments I received which have helped to boost my confidence and make me a more fulfilled person.

    Episode 80 Christmas Shopping with Jennifer

    Play Episode Listen Later Jan 20, 2025 11:38


    It's the holiday season with last-minute shopping to do! Hear about my time out as Jennifer including what I did and what you can learn from my experience.

    Episode 79 My Day Out in the Cold

    Play Episode Listen Later Jan 13, 2025 11:38


    It was in the 20s today but that didn't stop me from having a girl day. Hear about my adventure out as Jennifer - including a stop at Jiffy Lube!

    Episode 78 My Friend Tracy

    Play Episode Listen Later Jan 6, 2025 13:29


    Everyone likes real life stories right? In this episode I talk about Tracy, a friend I came out to years ago who helped to encourage me to go out in public and not be scared of who I am.

    Episode 77 Looking Back

    Play Episode Listen Later Dec 30, 2024 11:15


    Not too long ago, I found some old pics of myself as Jennifer. This caused me to look back at how far I have come as a crossdresser since those days and how everyone should take time to see how much they have grown as a person over time.

    Episode 76 Day-to-Day Mentality

    Play Episode Listen Later Dec 26, 2024 9:47


    If you're a crossdresser, chances are you will notice that you have a different mentality or state of mind when you're en femme. Does this affect your regular thoughts or mental state on a daily basis? Find out what I've discovered about myself in this episode!

    Episode 75 A Grand Day Out

    Play Episode Listen Later Dec 23, 2024 15:17


    How did I spend a day out as Jennifer? In this episode, hear what I wore from head to toe and hear about my adventure enjoying a morning as a woman. If you enjoy hearing about being out in public, this one's for you!

    Episode 74 I'm a Hypocrite

    Play Episode Listen Later Dec 19, 2024 10:54


    In this episode, hear me explain why I think I'm a hypocrite and don't always practice what I preach. It's a shameful confession I wanted to get off my chest.

    Episode 73 Sexy Soccer Mom

    Play Episode Listen Later Dec 16, 2024 8:22


    In this episode, I talk about dressing not only to fit the occasion but also to fit the weather conditions. Sometimes it's better to be practical than glamourous.

    Episode 72 A Cold Day in November

    Play Episode Listen Later Dec 12, 2024 20:04


    What is a girl to do when you have a day planned only to have it be chilly and rainy? In this episode, find out how my day was made special as I went out for a Jennifer Day!

    Episode 71 How I Feel Feminine

    Play Episode Listen Later Dec 9, 2024 9:08


    For some wearing pantyhose is what it takes to put the icing on the cake of feeling feminine. For others it may be high heels, a wig or (for me) bouncing boobs. I talk about what triggers the ultimate feminine feeling in me and why each of us is different.

    Episode 70 Wearing Women's Clothing as a Guy

    Play Episode Listen Later Dec 5, 2024 6:13


    A listener wanted to know if I ever wear clothing made for women while I'm in guy mode. In this episode I answer that question and also discuss whether sneaking a feminine article of clothing into your everyday male wardrobe is for everyone.

    Episode 69 Finding Friendship

    Play Episode Listen Later Dec 2, 2024 11:19


    Recently I had a nice sit-down first meeting with another crossdresser I met online. How I make friends via social media and why face-to-face meetings are so much more fulfilling are the topics of this episode!

    Episode 68 Flirting

    Play Episode Listen Later Nov 28, 2024 9:40


    A crossdresser recently said that a woman needs to be actively flirting in order to get hit on by a guy. In this episode, I talk about why I don't think this is necessarily the case.

    Episode 67 Gene Simmons is Wrong

    Play Episode Listen Later Nov 25, 2024 9:56


    Dancing With the Stars had Kiss' Gene Simmons as a guest judge recently and his comments caused quite a stir. Here I discuss why he is wrong in what he had to say.

    Episode 66 A Trip to the Grocery Store

    Play Episode Listen Later Nov 21, 2024 12:51


    For those of you who enjoy real life stories, here's one about one of the first times I braved people - by going to a small grocery store in Iowa.

    Episode 65 Happy Halloween

    Play Episode Listen Later Nov 18, 2024 8:33


    Halloween is like Christmas for crossdressers! In this episode, I chat about Halloween and how even just going out en femme is okay on this holiday.

    Episode 64 Sex Sells

    Play Episode Listen Later Nov 14, 2024 10:39


    In this follow-up to Episode 63, I spend a bit more time discussing my sex life - from my first attraction to someone through present day and how sex factors into my crossdressing.

    Episode 63 My Feminine Desires

    Play Episode Listen Later Nov 11, 2024 19:01


    It's time to come clean about my feminine thoughts and desires. When I dress as a woman, what desires do I have? Do I hope to get more than a guy's attention? Find out in this episode!

    Episode 62 She's Got Legs

    Play Episode Listen Later Nov 7, 2024 9:16


    Most crossdressers - myself included - love the feeling of wearing a skirt or dress and showing off our legs. It's one of the highlights of being a woman. Why do we find having smooth legs and wearing a skirt so appealing? I attempt to explain why going out in a miniskirt makes me feel so feminine in this episode.

    Episode 61 Meeting Other Crossdressers

    Play Episode Listen Later Nov 4, 2024 9:29


    One of the worst things about being a crossdresser is the feeling that you're alone. Many girls think they are the only one who feels this way or enjoys dressing as a woman. Finding others that feel the same way used to be very hard but has gotten easier over time. Listen to me talk about ways I have found other girls and sisters and how you can do the same thing!

    Episode 60 Things to Learn

    Play Episode Listen Later Oct 31, 2024 11:05


    For many of us girls, we have been dressing for years and years. Throughout our journey we have learned tips and tricks to becoming a woman from head to toe. However, it's impossible to learn everything or be an expert on it all. Here are some areas that I could develop more and become better at.

    Episode 59 Shopping for a Girl as a Guy

    Play Episode Listen Later Oct 28, 2024 9:06


    If you're just starting out on your feminine journey, you'll need to go shopping for makeup, clothes, shoes and more. Can it be embarrassing to shop for women's items when you're a guy? Are there ways to get everything you need without revealing that your items are for you? Hear about my experiences shopping as a guy for women's clothes, as well as tips to help make the experience easier right here!

    Episode 58 Wanting Attention

    Play Episode Listen Later Oct 24, 2024 10:39


    Sometimes when women go out, they dress provocatively in hopes of attracting attention from the opposite sex (or the same sex in some cases.) As a crossdresser most times you don't want to draw attention to yourself, but there are times when you do want to experience what a real woman does. Why do I sometimes want attention from men when I go out? Find out in this episode.

    Episode 57 Dress for Sex-Cess

    Play Episode Listen Later Oct 21, 2024 10:58


    One day while I was out as Jennifer wearing a low-cut top and fairly short skirt, I started wondering if how I dressed was a disservice for real women. Am I demeaning women if I dress sexy or somewhat slutty? This question turned into a discussion with a female friend of mine - as well as this episode!

    Episode 56 The Boobs Have It

    Play Episode Listen Later Oct 17, 2024 8:48


    Most crossdressers would say that having boobs is one of the important parts of their dressing. I think most biological women would agree that their breasts are symbols of the power they have in a male-dominated world. For me, having boobs when I go out as Jennifer is both a turn-on and important to have and show. Hear me discuss why this is and more in this episode.

    Episode 55 Courage

    Play Episode Listen Later Oct 14, 2024 10:32


    Guts, intestinal fortitude, courage - it takes a lot of all these for a crossdresser to get dolled up and go out in public. Even veteran girls have times when they feel frightened when going out. In this episode, I talk about what I do to chase these fears away and enjoy being out in the world as Jennifer.

    Episode 54 Musings

    Play Episode Listen Later Oct 10, 2024 9:02


    Do you ever wonder what I think about when I'm out as Jennifer? In this episode I discuss a couple of random topics I thought about recently while I was enjoying a girl day.

    Episode 53 Where Do I Go?

    Play Episode Listen Later Oct 7, 2024 16:14


    So you're finally ready to leave your home all dressed up en femme for the first time. Where do you go? What are some good locations to venture out to and experience being out as your feminine self and not be afraid? Here are some places I enjoy going and other ideas to make those times out not so frightening.

    Episode 52 Dressing on a Limited Wardrobe

    Play Episode Listen Later Oct 3, 2024 11:39


    For many girls out there a wardrobe can be rather limited due to finances or space to store it. What are essential items to have in your closet if you can't have 20 pair of shoes, 50 dresses and 75 outfits? I give you some ideas and tips of what are must-haves in this episode.

    Episode 51 The Eyes Have It

    Play Episode Listen Later Sep 30, 2024 8:58


    The eyes are the windows to the soul, and for most people making eye contact is one of the first things they do when meeting you. In this episode, I talk about why getting your eye makeup on point is important to your overall appearance and one of my top things to do when dressing.

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