Jennifer's Tale: My Life as a Crossdresser

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!

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.

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!

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.

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 make the experie...

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.

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!

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.

Guts, intestinal fortitude, courage - it takes a lot of all these for a crossdresser to get dolled up and go out in public. Even veteran girls have times when they feel frightened when going out. In this episode, I talk about what I do to chase these fears away and enjoy being out in the world as Jennifer.

Do you ever wonder what I think about when I'm out as Jennifer? In this episode I discuss a couple of random topics I thought about recently while I was enjoying a girl day.

So you're finally ready to leave your home all dressed up en femme for the first time. Where do you go? What are some good locations to venture out to and experience being out as your feminine self and not be afraid? Here are some places I enjoy going and other ideas to make those times out not so frightening.

For many girls out there a wardrobe can be rather limited due to finances or space to store it. What are essential items to have in your closet if you can't have 20 pair of shoes, 50 dresses and 75 outfits? I give you some ideas and tips of what are must-haves in this episode.

The eyes are the windows to the soul, and for most people making eye contact is one of the first things they do when meeting you. In this episode, I talk about why getting your eye makeup on point is important to your overall appearance and one of my top things to do when dressing.

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.

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!