Jennifer's Tale: My Life as a Crossdresser

Jennifer's Tale: My Life as a Crossdresser

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!

Episodes

August 4, 2025 9 mins

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!

Mark as Played

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.

Mark as Played
July 21, 2025 10 mins

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.

Mark as Played

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.

Mark as Played
July 7, 2025 10 mins

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.

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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.

Mark as Played
June 23, 2025 9 mins

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.

Mark as Played
June 16, 2025 10 mins

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!

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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.

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June 2, 2025 10 mins

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!

Mark as Played

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?

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May 19, 2025 16 mins

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!

Mark as Played
May 12, 2025 13 mins

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.

Mark as Played
May 5, 2025 10 mins

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.

Mark as Played
April 28, 2025 13 mins

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.

Mark as Played
April 21, 2025 13 mins

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.

Mark as Played
April 14, 2025 12 mins

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...

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April 7, 2025 10 mins

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.

Mark as Played
March 31, 2025 15 mins

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!

Mark as Played

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.

Mark as Played

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