Jennifer's Tale: My Life as a Crossdresser

For those of you who enjoy real life stories, here's one about one of the first times I braved people - by going to a small grocery store in Iowa.

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.

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.

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 experience easier right here!

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!