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

June 30, 2025 7 mins

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.

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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.

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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!

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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!

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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.

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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.

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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.

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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.

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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.

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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!

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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.

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March 17, 2025 14 mins

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.

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March 10, 2025 10 mins

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!

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March 3, 2025 12 mins

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...)

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February 24, 2025 18 mins

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.

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February 17, 2025 10 mins

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.

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