Jennifer's Tale: My Life as a Crossdresser

Many people suffer from an addiction, whether it be smoking, alcohol or drugs. Could crossdressing be considered an addiction? In this episode I take a look at addiction and debate if the desire to dress as a woman can be looked at as an addiction or not.

Many crossdressers who don't have the opportunity to dress are always looking for a way to feel feminine. Getting a pedicure - even as a guy - is a great way to indulge yourself, feel feminine and not have to worry about what others think. Hear me discuss why this is a great option!

Many years ago I had a girlfriend who helped encourage my crossdressing along with my desire to be out in public. Hear a story about a time when we went out on a journey, my apprehension to do so and the lesson I learned from this adventure.

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.