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!

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Jaksot(173)

Episode 156 Tales From the Car

Episode 156 Tales From the Car

Sometimes whatever can go wrong will go wrong. In this episode hear how my usual plans for a Jennifer morning go astray and what happens by the end of it. Do I have a good day or bad?

29 Touko 16min

Episode 155 AI vs Reality

Episode 155 AI vs Reality

In today's world AI-generated art is getting more and more prevalent. For many crossdressers using AI pictures and videos is an easy way to represent who they wish they were or desire to be. Here is w...

22 Touko 11min

Episode 154 Deal With the Hand That's Dealt to You

Episode 154 Deal With the Hand That's Dealt to You

Life can be compared to many things - a marathon, a race, a game et. For many life is like a poker game and you have to play with the hand you're dealt. In this episode (and thanks to my friend Michel...

15 Touko 11min

Episode 153 What My Wife Knows (But Doesn't Say)

Episode 153 What My Wife Knows (But Doesn't Say)

My wife knows about my crossdressing but prefers not to know where I go or what I do. However, there are hints and questions she says that makes me wonder. What secrets do you keep and what do you rev...

8 Touko 11min

Episode 152 Makeup Tips and Simplicity

Episode 152 Makeup Tips and Simplicity

Many crossdressers have a tough time learning how to do makeup. While it's not an easy feat, it can be a lot simpler than most girls think. In this episode I share some of my secrets for making your m...

1 Touko 18min

Episode 151 Friendship

Episode 151 Friendship

There are times when life can be bad. Really bad. When times take a turn for the worst sometimes you need a reminder or a blessing to show you how lucky you are. Here's an example of how that happened...

24 Huhti 12min

Episode 150 My Biggest Challenge

Episode 150 My Biggest Challenge

For my 150th episode, listener Julie Shaw asked me a doozie of a question! What has been my biggest challenge as a crossdresser? Find out my answer in this anniversary episode.

17 Huhti 14min

Episode 149 What is Two-Spirit? CORRECTED

Episode 149 What is Two-Spirit? CORRECTED

The term "two-spirit" is something I found out about relatively recently. As a crossdresser you may find this idea fits you like I think it does me. Learn more about it in this episode.

14 Huhti 11min

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