The Ultimate Crossdresser/Transvestite Guide

About Wanda 

Hello my friend!  My pen name is Wanda Wilson, and my femme naughty name is Wicked Wanda.  I have been crossdressing for about twenty years and thoroughly enjoy the experience.  I was a classic case.  I remember when I was as young as five years old, having a fascination for bras.  I once got into my mother’s laundry and began playing with her bra.  As I got older at about eight or nine years of age, I began to really notice the difference between men and women.  A female cousin of ours came to stay with us and I could not help peaking at her cleavage.  I also could not resist looking at her crotch.  I was curious as to why hers was so smooth.  There was no bulge even when she wore tight pants.

As an adolescent, I didn’t think much about this subject, except that I wondered what it would be like to get a kiss from a real girl.  Most of my adolescence was occupied by playing sports, and hanging out with my friends.  I was just an average boy.

When I became a teenager, my life was primarily focused on sports.  I was a pretty good baseball, and basketball player.  I was short, had a slight build, but I was strong, and would not let bigger guys push me around.  My fantasies at this time, or should I say my “wet dreams” came when I thought about getting to “second base” with a girl. I imagined what it would feel like to have a nice firm breast in my hands! I was a typical teen-aged boy with raging hormones. All I thought about was getting a girlfriend and fantasizing about when I was going to lose my virginity!

During my college years, I was going to school, partying, and having as much sex as I could with as many girls as I could have it with.  I finally got my first taste of sex and I loved it!  I wanted more and more and more.  I didn’t think much about crossdressing at this time.  I was too busy trying to pick-up girls, and trying to get through school.  It was the 70s.  Disco was king, the nightclubs were hot and the women were hotter!

At the end of the 70s, I got married, had a full-time job as a psychologist, and had a daughter.  I was focused on family life.  Two years after my daughter was born, I got divorced.  I hooked up with another woman and life became great again.  She was fun to be with, we traveled and we had great sex!  It was at this time that the cross-dressing urge started to surface.  When I was married, I started to try on some of my wife’s spandex tops.  I would stuff them with rolled-up socks to create breasts.  When I was with my girlfriend, she would go to work and I would sit alone in her house.  When she was gone, I would pull out her silicone breast enhancers and play with them under my T-shirt.  For some reason, I have always had a fascination with breasts!  To this day I still love a great pair of firm tits!

I had a great time during the 80’s!  Since I now had some play money, I could afford to travel, go to nice restaurants, and socialize with friends.  My girlfriend and I spent a lot of time together, but I never let on that I had a desire to wear her clothes.  I only fantasized about it in private.  The most daring that I ever got was to wear some makeup and paint my nails for a Halloween outfit. 

By the late 90’s I had a new girlfriend and my crossdressing life began to bloom.  I decided that since I was now in my 40’s, I should just experiment and go with the urges that were always inside me.  I bought a wig, some foam breast forms (they were terrible), some high heeled pumps, and a tight, black dress.  Sometimes a girlfriend would spend the night and forget her lipstick the next day, so I would just happen to forget to return it.  I bought a little makeup, and started to explore the possibilities.  I had my own house, and I lived by myself so I could indulge my fantasies whenever I wanted.  I discovered that I enjoyed the experience. I did not dress very often, but I really got a strong sexual feeling when I did.

One day my girlfriend and I were playing around at her apartment.  She suggested that because I was about her same size, that she should put one of her dresses on me, and put some makeup on me.  I tried to act reluctant and said “no, no”, but on the inside I was saying “YES, YES!”  I couldn’t believe it!  A fantasy was coming true! I loved it!

Then, one night, my girlfriend was at my house.  We were playing around and again she suggested that she should dress me up and put some makeup on me.  It was then that I revealed that I happened to have a wig and some clothes that she could put on me.  She dressed me and made me up completely.  We even took pictures of my femme image.  I was delighted! It was also difficult to hide my erection!  I couldn't help myself!

As we went along, my girlfriend encouraged me to express my feminine side.  We would shop for clothes together, and we would experiment with different ‘looks’.  She gave me the freedom to express myself, so I went with it.  I started to buy better-looking wigs, high quality silicone breast forms, shoes, and complete outfits.  We started to perfect the makeup techniques.  Eventually, we started to go out in public.

I remember the first time out was just going through the drive-up window of McDonald’s.  My girlfriend was driving my car and I was on the passenger side all made-up and looking hot!  I thought it was a nice feeling to have the seatbelt situated between my breasts.  The jiggling sensation of my breasts was driving me crazy!  As we drove in my car, my heart was racing.  I was sure that we would be stopped by a police officer and I would be discovered.  We finally got to the drive-up window and the clerk said “Good evening ladies can I take your order?”  Wow!  She said “ladies.”  I was thrilled!  I wanted to stay out all night!  It was fun, scary, and exciting all at once!

As we went on, I progressed to dressing more often, and going out in public more often, to movies, galas, and just being out and about in large cities.  It’s been fun! I have been lucky enough to have a girlfriend that allows me to express this feminine side.  She accepts it, and I even think that it turns her on although she does not want to admit it.  We’ve had some of the best sex with both her and me dressed in wigs, hot makeup, nylons and garter belts!

I developed this website because I know there are many other males out in the world just like me with similar stories.  This hasn’t been an easy road.  There is often much guilt, anxiety and perhaps depression involved.  There can be very complicated issues that can arise in a relationship between a wife or girlfriend, and a crossdressing husband or boyfriend.  

American society has not completely accepted the phenomenon of cross-dressing.  There continues to be much confusion and misunderstanding about this practice.  As a psychologist, I felt that I needed to provide information and resources to answer the many questions about transvestism for both the crossdresser and the crossdresser’s significant others. I also wanted to provide emotional support and practical information to my many “girlfriends” out in the world who are beginning to explore this side of their personality. I'm always looking for new tips to share that will help you not only  to become a passable crossdresser, but to help you become an "ultracrossdresser" with the goal being to perfect your feminine image, and to help you to maximize your enjoyment of the overall experience.

Have fun and play with yourself,

Wicked Wanda