Jennifer's Tale: My Life as a Crossdresser

Many followers have complimented how genuine and authentic I am on my podcast. But how authentic can a crossdresser truly Be? From our outside appearance to how secretive we are about our dressing, it can be tough to be your true self. In this episode I tackle this big subject and try to dissect it a bit!

Since I became comfortable with being a crossdresser I have shared this side of myself with many friends and family. Most of the women I have told have been supportive of me, but there are several who have become closer friends because of it. In this episode I personally thank several girls who have gone above and beyond to make me feel loved and show you that you probably have the same type of people in your life.

Every crossdresser starts out be dressing within their four walls. But the urge to go outside is strong. In this episode I discuss how I began my journey to go out in public and how you can take "baby steps" on your way to a more fulfilling life.

Pride Month has come and gone for this year. It was great to see so many people out and proud, being themselves. But do some people take it a little too far in their appearance and flamboyant dress? In this episode I ask which is better for representing ourselves, being loud and proud or more subdued and everyday.

Everyone has regrets. In this episode I talk about some of my regrets I have regarding my crossdressing - from missed opportunities to dress more over the years to people I wish I would have come out to in the past.

If you're like me and have a wife or girlfriend, it can be really tough to discuss your crossdressing, feelings and thoughts with them. In this episode I talk to the wives and significant others out there and try to help you tell them how much you appreciate them.

If you follow me on social media you may know that Jennifer's Tale is an audio and video podcast. The video feed (which can be found on Youtube) is a few episodes ahead of the audio feed so I'm going to give my audio listeners an extra episode every week until both feeds sink up! Thanks for listening and hope you enjoy!

Courage comes in all forms. Whether it's courage under fire, standing up to a bully or facing a fear of flying it takes something special to be courageous. But have you ever thought about how courageous it is to be a guy who dresses as a woman? In this episode I remind myself and you how courageous you are!

I've discovered over the years that if you want to get someone talking, ask them about their kids (if they have any) or what they enjoy doing in their free time. I've shared a lot about myself during my podcast. This time around I talk about my hobbies and where my passions lie. Hopefully you will share yours with me!

Sometimes putting words down on paper helps. Whether its a post-it of encouragement to yourself, a note to a friend thanking them for being there for you or a letter to a loved one who has passed on telling them about your feminine side being able to express yourself does wonders. In this episode I talk about letter writing!

Summer is here and while there are benefits of vacation and other things, having your kids home for three months can cut into crossdressing time. What can you do to get some time for your femme self? The title to this episode says it all!

It's a feeling every crossdresser has - being ashamed of who they are and why they have the desire to wear women's clothing. Coping with this can range from guilt to purging. In this episode I discuss how I've dealt with shame and why you shouldn't be afraid of who you are.

Some trans girls don't feel that crossdressers are a part of their "group" for whatever reason - maybe it's because they aren't women 24 hours a day or maybe because they don't have the desire to be a woman full time. But does a crossdresser qualify as a trans individual? Here are my thoughts.

There are times when I realize that, even though I may not be dressed as Jennifer, I'm spending a lot of time thinking about my femme self and girl things. Is there such a thing as not having enough "guy time" or thinking more about your crossdressing than your real life? It's something that many girls have an issue with and I discuss it in this episode.

Are you a crossdresser that keeps your feminine side a secret? Do you have a storage locker or somewhere you keep your makeup and clothes? What would happen if something bad unexpectedly happened? In this episode I talk about planning ahead i case you meet an untimely demise.

For many crossdressers, sensory stimulation is one of the perks of dressing. From the smell of perfume to the gentle pull of dangly earrings, having the sense aroused can be very erotic. IN this episode I talk about my favorite way to stimulate my feminine senses - wearing pantyhose.

For some girls, getting ready to be their femme selves takes hours. Is it worth all the time and effort to feel your feminine best? In this episode I discuss preparation versus reward in my own experience.

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!

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.

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!

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?

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!

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.

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.

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.

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.

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...

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.

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!

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.

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.

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!

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...)

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.

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.

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.

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!

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.

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.

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!

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.

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.

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!

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!

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.

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.

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!

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.

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.

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!

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.