CHAPTER 3
The Road to Cross Dressing

One of the best moments for a cross dresser is to imagine the time he’ll have to enjoy his female clothes. The expectation of the feeling of the fabrics against his skin is something difficult to explain in words. The best analogy I can think of, is this: thinking about the moment you’ll be wearing women’s clothing is like thinking about the beer you’ll be drinking after you finish a 20 mile hike across the desert.

After accepting this new stage in my life I dedicated myself to dress as a woman practically every afternoon for five years. As my dad would become more involved in his research and as my mom afforded me greater independence and she would spend most afternoons away from home, I would indulge in my fantasies.

I was self-taught. I took fashion magazines and I began to experiment with every aspect of the female appearance: from combining different clothing styles, to the appliance of all kinds of make up.

Gradually, my feminization became second nature to me, and I started discovering the beauty and wonder of the female socialization process.

Have you ever noticed what the first and most noticeable difference between men’s clothes and women’s clothes is? Men’s clothes tend to be baggier, looser and tend to hide the shape of the body of a man. As a result, the materials from which men’s clothes are made of, are drab, simple and without texture (mostly cotton and polyester blends).

But women’s clothing ENHANCE a woman’s body. As a consequence, female clothes are snug where they have to be, and loose where it best accentuates the female figure. Women’s clothes tend to be more snug around the chest, belly and hip area, and is completely loose around the legs and calves. Also, the fabrics that make the female clothes are rich in texture and color (rayon, nylon, cashmere, polyester, soft cotton, etc.).

All this I learned by wearing it. Every afternoon, as soon as mom left the house, I’d strip, toss my clothes in the hamper and raid her closet. I’d wear dresses, skirts, blouses, high heels, silk stockings, nylon pantyhose — the works. And all of this would be accompanied by long make-up sessions in which I applied base, blush, mascara, eye liner, eye shadow, lipstick, etc.

I started letting my hair grow and I got my ears pierced, under the guise that it was a phase I was going through. Mom and dad didn’t approve too much, but they gave me enough room to express myself as a teenager, and pierced ears were not that bad, compared to other teenagers who would get nose rings, tattoos and shaven heads.

I was a full blown transvestite, enjoying every minute of it. By the time I was 15, I was able to transform myself into a beautiful young lady without thinking twice about it.

Unfortunately, at 15, my masculine side started fighting back and suddenly I noticed that I was starting to grow hair on my chest, arms, face and legs. At first, it was so small and blonde, that it wouldn’t show. But as I grew up, my body mass was increasing and my legs got hairier and hairier.

Two months before my 16th. birthday, I made the mistake of shaving my entire body under the claim that I was trying out for the swim team. Two terrible things happened. First of all, my mom freaked out. She called me a sissy and developed the notion that she was neglecting me and needed to spend more time with me. So my afternoons of feminization came to a halt. And secondly, I became the target of every single bully in school, that kept beating me up for being hairless in a sea of hormones that had guys trying to show off their newly formed body hair.

So suddenly, I found myself being deprived of the activity that I craved most, when I still had the body to really enjoy it.

Through the years, I had managed to hold on to clothes that my mom wanted me to donate to charity. I would keep a few skirts, dresses, panties, pantyhose and I would carefully hide them in my room and wear them when everyone was asleep.

But it wasn’t enough. I was frustrated not to be able to wear makeup. Or to be confined to the privacy of my room when I had gotten used to doing my homework and watching television in my favorite dresses and skirts.

To make sure that I got the most pleasure out of my private dressing sessions, I would continue to shave my body pretending that I was naturally hairless and that it was taking way too long to grow back.

My parents didn’t like the idea of a hairless son, but to their credit, they never outwardly expressed any resentment at my hairless condition for a while. And to be honest, I wanted to shave myself for the longest possible time to try to keep the effects of masculinization from dominating my body completely. I knew that at a certain given moment in my developmental stage, I would have to face up to the fact that my torso would be square and I would eventually lose my feminine figure.

Up to that point I had taken care of keeping my weight down as much as possible. I became a vegetarian, and although I was 5’11 I weighed only 125 lbs. I was a size 4 (my mom was size 2) and I enjoyed the fact that I had a better body than most girls at school.

In fact, shortly before summer vacation, a bunch of jocks decided to toss me into the girl’s locker room. Naturally, the girls freaked out, and regardless of whose real fault it was, the women’s volleyball coach had me stay after school as punishment for being such a pervert.

The good thing about it was that the new cheerleading uniforms had arrived and they had them in storage in the back room of the school’s basement. So naturally, when I was asked to put all the balls in their racks, and I found myself alone at 4:30 PM in the school basement, I went for those uniforms.

I slowly went from aisle to aisle making sure no janitors, students or coaches had stayed behind. When I was sure I was all alone, I ran towards the back of the basement and started looking for a size 4 uniform.

Sure enough, I found one.

The thrill of being on school grounds alone with a cheerleading uniform was enough to give me a huge boner before I even took my clothes off. I was about to take my tee shirt off, when I heard a few noises coming down the hall. I got a sting in the pit of my stomach, and I decided to look and see who it was.

I found no one, but the sound made me become more careful, and I went into the girl’s bathroom and went inside a stall, closing the door behind me. Although I didn’t have much room, I started taking off all my clothes as fast as I could. Before I knew it, I was stark-naked inside the stall, and I was looking a this uniform through a flimsy, transparent plastic bag.

I slowly lifted the bag and removed the sweater. It was a burgundy sweater with yellow and white stripes. I put it on, and the soft, cotton texture gave me an immediate hard on.

With my trembling legs, I grabbed the mini skirt and pulled it up. My hard, bulging cock almost didn’t let me raise it to my waist, but I maneuvered around it and fastened the soft, polyester skirt. IT WAS A PERFECT FIT! I closed my eyes and imagined I was out on the field prancing around in my outfit with 14 other girls… I got so emotional, I almost cried.

I couldn’t help myself and I opened the door to look at myself in the mirror. I was ecstatic. Right across from me in the mirror, stood a beautiful girl with a white mini skirt and a burgundy sweater. Almost as a reflex action, I started rubbing my hard cock.

Suddenly, I heard the women’s coach storm outside the bathroom looking for me. I panicked and ran back into the stall as quickly and quietly as I could. I knew that if she saw me, I’d be in the biggest problem of my life. I’d never live it down.

Very quietly, I closed the door of the stall, locked it and picked up all of my clothes. I stood up on the toilet, closed my eyes, and prayed to God that the coach wouldn’t find me.

The coach stormed into the bathroom cursing. “Goddamnit where the hell are you? If you left for home I swear I’ll have your coach have you running laps until you cough up a lung!”

I guess she simply looked under the stalls and never bothered to open the doors, because she stormed out pissed off and yelling at me.

Inside the stall I was in transvestite heaven. The thrill of almost being caught made me cum right there and then. I squirted into the skirt and soiled it inside. But there was nothing I could do. I simply put the uniform back on its hanger, covered it with the plastic bag and got dressed.

Very carefully I stepped out of the bathroom and returned the uniform to its rack. I went back towards the storeroom and finished placing the balls in their racks.

Just as I finished, the coach stormed inside.

“Where the fuck were you?” She barked at me.

“I went to the boy’s bathroom and took a dump”.

“Why didn’t you answer me, goddamnit?”

“Would you answer to someone if you were taking a shit?” I replied almost angrily.

The coach looked at me for a second in silence, then, very slowly a thin smile drew across her face. She liked my attitude, and after seeing that I had finished cleaning up, she dismissed me.

“All right. You can go home. Your mom is waiting for you in the gym. Just don’t let me catch you in the girl’s dressing room again…” she said, as she dismissed me.

My mom was waiting for me in the gym and we walked together to the parking lot where she parked the car.

During the ride back home, I kept thinking about the moment the coach almost caught me dressed in the cheerleader outfit. Just remembering it, was enough to give me another hard on.

My mom kept going on and on about school stuff and responsibilities and crap like that, but I was away thinking how exciting it was to be dressed as a woman when someone else was In the room. The thrill of almost being caught was like a drug that I was quickly becoming addicted to. I just kept thinking that I would start wearing women’s clothes all the time, at all hours, just to feel the thrill it provided.

As soon as we got home, my mom asked me to help her with dinner. But before that, I went upstairs and put on a bra, a pair of panties and nylon pantyhose under my clothes, then I went downstairs to help her.

I had an incredible hard on that I had to hide from her, and when dad arrived and we sat down, I kept rubbing my cock under the table right in front of them. They never noticed it, and as I went to my room for bed, I realized that I had yet arrived at a new stage of my cross dressing.

The following day, I stopped wearing my own underwear. Even on the days I had gym class, I’d arrive in school with my own underwear, then after gym class I’d go into a stall and put on my panties and bra, then cover them with my shirts or sweaters.

The thing about cross dressing is that it resembles taking drugs. It may feel almost like it, because it seems to be addictive and the more addicted you become the bigger the fix you need. Regardless of that, the truth is that cross dressing became a part of my own identity. And expressing my identity became an important part of my life. So I needed to express myself more and more to be happy. This translated into wearing women’s clothes more and more often, and more and more openly every single day of my life.

My cross dressing had evolved into an important aspect of my life, and I couldn’t relate to girls as a boy anymore, first of all, because they liked to torture me, and secondly, because I was more attracted to their clothes than their bodies.

I must stress, that at this point in my life, I had but one great sexual frustration. I wanted to fuck my own mother. I knew that was not going to happen. But for that matter, I never considered myself to be gay, or even bisexual.

To be perfectly honest, I didn’t feel attracted to men. My sexual inclination was very simple indeed: I wanted to fuck my mom, as I was wearing her clothes.

Little did I know, that this obsession had already placed me in a path from where I would never be able to return.