Jennifer's Tale: My Life as a Crossdresser

In my wife's attempt to accept my crossdressing, she said that she felt that I was more feminine than she is because she normally doesn't wear makeup or enjoy dresses. In this episode, I discuss whether or not there is a competition between a crossdresser and a significant other to be more feminine and how I feel about this topic.

The term trans is often used to encompass a variety of people in the LGBTQ+ spectrum. As to whether a crossdresser falls into that category varies, depending on who you talk to. In this episode, I talk about my interpretation of the word trans and how I feel I land in this broad word.

Sometimes after not dressing for a while, it can be a challenge "getting back into the swing of things." Since I myself have had a couple months of downtime, in this episode I discuss how to get back to being the woman you enjoy being after an extended hiatus.

Do you believe in fate or coincidence? In this episode, I tell a story about my best friend growing up, how our lives kept crossing paths and how two people from a small town had more in common than they could have imagined.

Gender fluidity is a term that wasn't around years ago. Boy George and David Bowie would fit that category - someone who exhibits or dresses as both sexes - and some crossdressers do this too when not fully dressed as a woman. Here is my take on gender fluidity and where I fall into this rather broad term.

A listener wrote in with a question for me: Where do you see yourself in 25 years? Would you be Jennifer fulltime? In this episode I send a message back to my 2024 self as I try to guess what Jennifer will be doing in 25 years' time.

What can a crossdresser do when you don't have an opportunity to fully express yourself? Underdressing, or wearing women's clothing under your regular male clothes, is an option many use. In this episode I talk about underdressing, the pros and cons and how it's a viable option for many people.

As a crossdresser figuring myself out in the early 1990s, there were many talk show episodes that featured crossdressers and female impersonators. In this episode, I talk about three women from this era who helped me to feel better about myself as Jennifer and made me more confident in who I am now.

One of the most important parts of being a crossdresser - and sometimes the hardest - is having confidence. Whether it be confidence in how you look or faith in yourself to be out in public, being confident helps any crossdresser not only enjoy your time out but also will help you feel better about who you are. Learn all about it in this episode!

In having a conversation with a family member I was reminded of my childhood. Certain aspects and memories could be looked at as possible causes of my crossdressing. Is dressing like a woman inherent to some girls? Are some girls created? Or can both circumstances hold true?