CHAPTER 4
John

One of the most important aspects of cross dressing, is that the more you dress up, the more time you want to spend dressed up and the greater the need to dress more often.

Unfortunately, as a 17 year-old boy whose testosterone hormones started kicking in, it became more and more frustrating not being able to pass on as a girl anymore. My greatest heartbreak came when my mom’s clothes finally didn’t fit. I’d find a way to slip into something of hers, but now the reflection in the mirror had radically changed. It was no longer the reflection of a girl, but the reflection of a boy dressed as a woman.

To make matters worse my beard was getting thicker and thicker, and trying to convince people that I was hairless was becoming more and more difficult every day.

To my great horror and unbelievable frustration, my senior year in high school was one in which I had to face the fact that I didn’t look good as a girl, that I did not have a female figure and that I was not looking all that believable in women’s clothes anymore. This despite the fact that I was 5’10 and weighed 145 lbs. As slim as you may be, testosterone increases body hair, muscle mass and bone density.

The feelings were still there: I wanted to fuck my mom. I was attracted to her. But she would never sleep with me. And I still wanted to wear her clothes. But I didn’t look good in them anymore, and furthermore, they didn’t fit with my male-developing body.

But it was my senior year, and I was getting ready to go to college next year. Unlike my father, who was big in science, I was more oriented towards other interests: business administration, for instance.

Although my parents were hoping that I would follow in their footsteps towards a more academic career, I wanted to make good money in business. So I chose a good, Ivy League college in the Midwest and I applied for business school.

With my grades and my family’s academic record, I didn’t have any problems getting in, and the thought of becoming independent from my parents and leaving home was a great distraction to forget my sexual frustrations for a while.

After graduation, the summer before I left for college, I met someone who would change my life forever. A very wealthy sponsor of the science division at my dad’s university invited us to his summer home at Martha’s Vineyard to celebrate a breakthrough in my dad’s research.

This gentleman was in his early forties and was in the billionaire boy’s club in the same league as Donald Trump or Bill Gates. He was twice divorced and was a really nice guy.

John’s house at Martha’s Vineyard was one of those beautiful, classic, early American cottages with four bedrooms, swimming pool, sun decks, hot tub, private beach, etc.

That summer we arrived just a few days after I graduated from high school, and we were going to spend four weeks at John’s house.

The day we arrived I became very fond of John. Here was a guy with hundreds of millions of dollars in his bank account, and still managed to be a down-to-earth, nice guy. I guess it was mutual, because as we spent time together we developed a great friendship. This was nothing sexual or kinky. We just became good friends.

John was ten years younger than my dad, and he had made his fortune in software development and later expanded into real-estate ventures. As part of his business divisions he had donated millions of dollars to research (medical, electronic, etc.) because he would get a percentage of the patents, making him even richer.

But John was neither athletic nor exceedingly handsome. Like me, he had been a nerd in school and like me, he was never very good with women. But he was very bright and had an excellent eye for business.

By the time we arrived at his beach house I had returned to a relatively normal teenage life. I had not cross dressed for months and although I still had those feelings I had managed to keep them under control.

Unfortunately, the room John gave me belonged to one of his ex-wives and her closet was full of stuff she left behind. Suddenly, all these frustrations kicked in again, and I was facing a difficult situation. I wanted to wear them, but I was trying to have a normal life and putting on dresses would be a step back.

As a feeble attempt to keep my cross-dressing suppressed, I’d leave the door to my room open, even during the nights. That would project an “open” personality and would keep me from snooping around in the closet.

A full week into my trip to John’s house, he invited us to a bar. Although I was still well under 21, he managed to get me drinks, and I wound up pretty drunk. John was somewhat shit-faced too and as a bond between us had developed, he started telling me how his two wives simply married him for his money. He went on to confess that although they were very beautiful and he had fallen in love with both of them, his two ex-wives had been unfaithful to him, but he had outsmarted them by drawing these pre-nup agreements and hired a crack team of shark-divorce lawyers, so they had gotten nothing.

I told him that women usually made me very nervous and I’d never had any girlfriends. That night actually brought us closer as friends.

The following morning, everyone got up really early because John had set up a special trip out to sea to see whales swim in their natural habitat. His personal yacht would leave pretty early. Mom and dad were ready to go, but I had such a hangover, that when my mom came into my room to tell me to get ready, I excused myself because I had a terrible headache.

Mom insisted I should go, because it would take them 3 hours to get out to sea, a couple of hours to find and see the whale,s and 3 hours to get back. If I chose to stay, I’d be alone all day. At the moment, the headache didn’t let me think, so I simply shrugged her off and turned around to sleep.

When I finally woke up, the house was dead quiet. Not a single noise came from any of the rooms. So after drinking some coffee to bring my hangover down, I went back to bed and turned the television set on.

As I tried to focus on the TV, my eyes started wandering around the room until they landed on the closet. I knew that there were a bunch of wonderful clothes in there, and as much as I tried to fight off the feeling, I knew I was alone and this was the perfect moment to try them on.

Finally, I couldn’t take it any longer and I started snooping around. Even before I opened the closet door, I had a boner the size of the Washington Monument. So I simply took off my boxers and my tee shirt and I opened the door, buck naked.

The mere sight of all these wonderful clothes was enough to almost made me have an orgasm right there. I immediately went for the drawers and started going through the underwear. I picked out a pair of black, silk panties and some black stockings. There was a black corset that would give me a nice feminine figure and I ended up picking out a black, satin, cocktail dress. As the smoothness of the fabric draped over me, I couldn’t help rub my cock as fast as I could. I topped it off with a pair of black, stiletto high-heeled shoes.

The clothes fit rather snuggly, but in the end, I managed to get inside. I closed the closet door and looked at myself in the mirror. Oh, how I had missed that. As a transvestite who has repressed his feelings for months, being back in women’s clothes was like returning home after a long trip.

I started rubbing my cock as I contemplated the sight in front of me, and sure enough, I came almost immediately. The orgasm was long and wonderful. I shot a lot of semen into the panties, but since no one was wearing them, I didn’t care I had soiled them.

Strangely, the feeling of awkwardness also returned. As soon as I finished my orgasm, I looked at myself in the mirror and I felt silly. I felt ridiculous. And this awful feeling of guilt washed over me. I had gone for months without dressing up, and there I was again, looking like a fucking fag. My first reaction was to take the dress off, but I convinced myself that if I could hold on for a little while, everything would be okay again. After all, I had been away from these clothes for a long time. It was only fair that I spend a little longer time in them.

To distract myself, I decided to go downstairs and get something to eat dressed as a woman. As I walked down the stairs, the awkwardness disappeared, and once again I was enjoying my femininity to the fullest.

I was so caught up in my cross dressing, that the hangover disappeared and I actually felt hungry. I went to the fridge and started taking things out and putting them on the table. Once in a while I’d rub my cock to feel the soft, silky feel of the satin against my skin.

I was enjoying myself so much, that I didn’t care that my legs, arms and chest were hairy, or that I was even developing “five-o-clock shadow” on my cheeks and chin.

Just as I was ready to fix myself an omelet, I heard a noise upstairs. I froze and listened carefully. Maybe it was the wind. But no. It definitely sounded like footsteps. Then a door opened, and there was a voice crying out, “Hey, there! Are you downstairs getting something to eat? Hold on! I want some brunch too!” It was John! He didn’t go to see the fucking whales! He was home!

I looked at my reflection against a glass door. I was dead! If John came down and saw me, I’d never live this down. It would be a family scandal, and I’d get on the wrong side of a powerful billionaire.

As I heard him come down the stairs, I panicked. I had to hide! I ran as fast as I could to the bathroom, and I locked the door.

“Are you okay?” I heard through the door.

“Yeah. I’m fine. It’s just the hangover.” I replied.

“Been there… done that. I’ll start breakfast, if you’re still up to it”, he said.

“I’ll be out in a few minutes”, was all I could think of to say. Then I looked down. How the hell was I going to get back upstairs without him noticing? The dress ruffled too much and the stiletto heels clicked too loudly.

I decided to take the shoes off so I would make as little noise as possible and took a deep breath. I would have to make a run for it. The kitchen door was open and it faced the stairs. If he looked as I ran upstairs, I’d get caught.

I quietly opened the door to the bathroom and saw John scrambling the eggs. As I saw him from inside my dress, I got a huge hard on. Not because I was in love with him or anything like that. But the thought of having someone INSIDE THE ROOM while I was wearing a dress made me very hot.

As soon as he turned around towards the stove, I made my move. I quietly opened the door, and tiptoed as fast as I could towards the stairs. As soon as I reached them, I darted upstairs. I ran so fast that I dropped a shoe half-way up the stairs.

“Are you okay?” shouted John from the kitchen.

“Yeah. Fine. I’ll be right down”. Was my response. But then I heard him walk out of the kitchen. I felt like I was trapped. If he came to the foot of the stairs, he would see the shoe. But if I went down to get it he would see ME. I decided to take a chance and leave the shoe. I ran inside my room and took the stockings and the dress off. I kept the panties and the corset because I would never have time to get those off in time. I put on a shirt and a pair of jeans and raced out to get the shoe.

As I picked up the shoe, I saw John come around and start up the stairs. I managed to put the shoe behind my back and tuck the heel inside my jeans. As John saw me standing there he stopped and looked at me.

“What’s the matter?” he asked.

“Nothing” I said.

“Really? You look flustered. You’re sweaty and pale. Are you sure you’re okay?”

“I’m fine, really. It’s just my stomach. Too much vodka last night.”

John gave a thin smile. “I hear you. It’s happened to me too.” Then he started walking towards me.

I was in real trouble. I had left the door to my room open. If he walked by and looked in, he’d notice the dress on the bed. But if I turned around to close the door, he’d spot the shoe hanging from the back of my pants. Once again, I was trapped. As John passed in front of me, I stood against the wall and closed my eyes. If I was going to get caught, at least I wasn’t wearing the dress. I figured I’d talk my way out of it.

But John simply walked by the door to my room without looking in. He was too busy looking at some bits of skin around his fingernails and biting them off. I quickly ran into my room, tossed the dress and the shoes under the bed, then walked out to he hall to wait for him.

He walked out of his room very casually, then looked at me. I guess I was looking better, because he said, “Are you still up for some eggs? I made this killer quiche”.

“Yeah. I could eat something”.

“Great. Let’s go”.

I followed him downstairs and we had a great brunch. We talked about the previous evening and laughed at the stupid things we said and did.

After brunch we went upstairs, showered and got dressed. We spent the rest of the day hanging out and relaxing after the previous night. Not once, during the entire day, did he show any hints of my cross dressing. I figured I had gotten away with it. And that feeling only made me feel very horny and excited. As soon as John would turn around, I start rubbing my cock as I looked at him. But this wasn’t because HE made me hot. It was because I liked the idea of releasing my sexual frustrations IN FRONT of someone, without that someone knowing it.

Once again, the bar on my cross-dressing had raised another notch. For the rest of the three remaining weeks, I would wear John’s ex-wife’s clothes underneath mine. I would even wear her bikini bottoms under my swimsuits. Every chance I had, I would jack off behind my parent’s back or behind John’s back.

Once again, an event that had given me such intense emotions, would change my life forever.