Jennifer's Tale: My Life as a Crossdresser

Nov 18 2024 65 ep. 10 mins
Jennifer's Tale: My Life as a Crossdresser Podcast artwork

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!

  Society & Culture
RSS feed Share
Copy RSS


Subscribe on Podcast Addict


Episode 65 Happy Halloween

Nov 18 2024 8 mins  
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

Nov 14 2024 10 mins  
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

Nov 11 2024 19 mins  
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

Nov 07 2024 9 mins  
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

Nov 04 2024 9 mins  
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

Oct 31 2024 11 mins  
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

Oct 28 2024 9 mins  
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

Episode 58 Wanting Attention

Oct 24 2024 10 mins  
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

Oct 21 2024 10 mins  
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

Oct 17 2024 8 mins  
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.