INTRODUCTION

As I write these lines, I can’t help but think of the extraordinary events that have brought me here, and one question keeps popping into my head: what makes a man be a man, and what makes a woman be a woman?

You see, we may think that because a man has a penis, that makes him a man. But in reality, there are times when women are born as men, and they don’t realize that until someone comes along to show them the way.

At times, that way can be glorious, wonderful and exhilarating.

Other times, it can be a rude awakening.

But just like any other aspect of life, once you realize who you are in this world, then it is so much easier to find your place in it.

And that is precisely what happened to me.

For many years I have been keeping my story to myself. But now that I realize who I am, and what I want in life, if I don’t share it with others, I feel like I will go crazy.

If you are a cross dresser or a transsexual and you’re reading this story, you’ll be able to identify with many of the emotions and feelings described here. If you’re neither a cross dresser nor a transsexual, please take the time to think about what it means to be one. This story will help you do that.

You be the judge…

CHAPTER 1
My First Time

Have you ever felt nylon stockings press against your smooth, shaven legs? Or the softness and tightness of silk panties against your penis? Or how about the delicate, silky sensation of a satin dress as it presses against your chest and drapes down your waist?

How can you NOT be a transvestite?

The feel, the touch, the smell of women’s clothes can provide sexual rapture beyond any man’s desires. And any man who denies that is a liar. All men, by nature are attracted to well-dressed women. But it’s not only the woman that attracts men: it’s the clothes they wear. That’s why women take so much time buying clothes and figuring out what they’ll wear for the day.

This is what I found out the very first time I tried on my mother’s dresses. I was 13.

I could go on and on about my family, but I think that it’s enough to say that we were a typical, upper middle class family living in the northeastern United States.

My father was a research scientist at a genetics lab in a prestigious university and my mom was a typical housewife who started to look for something else to do once, I was old enough to take care of myself. She got involved with all my school activities, (PTA meetings, school plays, bake sales, etc.) as well as volunteer work in the community and things like that..

I didn’t have any brothers or sisters and I didn’t have many friends because I was neither popular nor sports-oriented at school. In other words, I was your classic, average nerd. Although my mom tried to encourage me to have greater school spirit, I was shy and introvert. The fact that the school bullies kept torturing me in gym class or during recess didn’t help me much to build a lot of school spirit or to have greater interest in extra curricular activities.

I had a relatively lonely childhood, because after my 13th. Birthday I saw my parents less and less. Dad spent all day at his research lab and mom was out of the house every afternoon. As a result, I spent most afternoons alone at home watching TV, surfing the web or playing video games.

Because I was so shy, I never had any girlfriends, and I had the most difficult time trying to talk to girls. When I did, they would usually make fun of me, and they would have their jock boyfriends torture me to death.

Like any normal boy, as I went into puberty my hormones started to kick in, and naturally I discovered the joys of masturbation. You could say I was a real champ at that and I was going for a world-record. Or at least it felt that way. As soon as my mom would leave for her afternoon activities, I would go into my room, flip open a few magazines (Playboy, Penthouse, etc.) and I would jerk away.

I spent so much time alone and I did it so often, that I got to the point of removing my pants and my boxers to make it easier and more comfortable to me.

I would get aroused by looking at girls in their cheerleader uniforms, or strut around in mini skirts around the mall. But since I never had the nerve to ask any of them out, I’d close my eyes, think of them in their sexy outfits, and jerk away.

Basically, that became my routine and those were my sexual habits.

Until one night… Then everything changed.

A couple of months after my 13th birthday, my dad had this big fancy, university dinner. You know… the typical party where awards are presented, speeches are read and people spend the rest of the night having dinner and getting drunk. Since I was 13, they figured I was old enough to take care of myself and they simply dressed up, kissed me good night and left for their big, fancy ball.

I was watching TV, and as I heard the car drive away, I took off my pants and my boxers and started jacking off. By then, I had managed to hack into the porno channels without my parents knowing about it. I flipped on the X-Rated networks and started jerking away.

But suddenly the phone rang, interrupting my concentration. It was my mom. I quickly fumbled with the remote to mute off the moans and groans and I picked up the phone.

My mom’s voice came over in a rapid, almost mechanical tone. “Hi, honey. Listen, I need you to do me a favor. I have to leave really early tomorrow morning, so I want you to take all the clothes from the hamper and put them inside the washing machine. Can you do that for me?”

“Sure. No problem”. My dreary voice seemed almost robot-like.

I hung up the phone, somewhat upset at the fact that my mom had broken my special moment. Since my penis had deflated, I decided to take care of what she asked me to do, so I could get back to my masturbating undisturbed.

I went inside my parent’s walk-in closet, I opened the hamper and I grabbed a whole bunch of clothes. There were several days of dirty laundry piled up in there, and I wanted to make as few trips as possible to the laundry room. So I tried to grab as much as possible, and naturally, the clothes would spill over the sides of my arms. As I started making my way towards the laundry room, this long, nylon nightgown started brushing against my penis. The softness of the fabric immediately caused a reaction.

I had to stop. I looked down, and noticed the gown touching my hard cock. It was a wonderful, new sensation. I dropped the clothes on the floor and grabbed the gown. I took it and started to rub it against my cock, discovering a marvelous new way to jack off. The feeling was incredible! The softness of the fabric. How smooth it felt against my crotch and my belly.

The feeling was so incredible, that suddenly I felt like I needed more. Simply rubbing it against my cock wasn’t enough.

I started looking very closely at the gown — It was soft pink and had lace surrounding the breasts. The nylon felt really soft, and I noticed how thin were the shoulder straps. This was nothing like the clothes I was used to wear. Heavy, cotton shirts and jeans. I never realized how important the TOUCH of the clothes was until that very moment.

I started wondering what it would feel like if I had it on. After all, the feeling of the gown against my penis was fantastic. I figured, that by putting it on, it would feel even better. Since I was thinking about the softness of the fabric, I really wasn’t thinking about the fact that I would be wearing women’s clothes.

I took off my shirt and my socks, and I put it on.

As I felt it drape over my body, I realized this was the best feeling in the world. I ran back into my parent’s bedroom and I looked at myself in the full-length mirror. I couldn’t believe what I saw. I looked like a GIRL. I didn’t look like a boy dressed as a girl… I looked like a girl without any make up on.

The reflection on the mirror made me feel very strange. After all, I was thin and not too tall. I never enjoyed sports, and so I had a small frame. My features were naturally soft and the lack of body hair and the rubber straps under the breasts suddenly gave me a girlish figure.

My legs began to shake. I got really aroused just staring at that girl looking back at me in the mirror. Without even thinking about it, my hands immediately went down to my crotch, and as I pressed the gown against my cock, my shaking legs started to buckle. Almost immediately I had an orgasm. But this orgasm was unlike any other I had before. This one seemed to last forever. My semen exploded inside the gown and the rapture almost made me faint. I fell on the bed, on my back, and I continued to rub the wet gown against my cock. The nylon felt almost painful, but I didn’t want the feeling to end.

I laid there, for what seemed an eternity. I was spent. I couldn’t move. All I could do was re-live the moment the soft, nylon fabric had grazed my cock and how I loved that feeling.

Slowly, my strength began to return and I sat on the bed. The vision before me was uncanny. I actually looked like a girl. I looked down, and I realized in horror that I had soiled the front of the gown. That made me feel silly and stupid. I started to panic and suddenly the gown made me feel stupid, instead of sexy. I figured I was going to get caught so I took it off quickly, and ran towards the bathroom sink.

There I was, buck-naked crouching over the sink with a bar of soap and my mom’s sexy, pink nightgown under the water. As I started to wash it, a thought struck me: I WAS SUPPOSED TO PUT IT IN THE WASHER MYSELF! My mom would never notice it.

As that thought relieved me, I shut off the water and rinsed the gown. Slowly, I walked over to the pile of clothes I had dropped earlier, thinking how stupid I was to get the gown all wet. I started picking up the clothes, and once again, the softness of my mother’s clothes against my bare chest started to have an effect on me.

If a simple night gown had caused that exquisite feeling, what would a pair of panties feel like? For that matter, how would it feel if I had a bra and pantyhose on?

As that idea started developing inside my head, I looked at myself in the mirror, and I realized that I still had the body of a small boy. I didn’t have a waist, or breasts, but my hairless body could easily pass for a girl.

As I thought about this, I remembered how turned on I was at my own reflection. If I looked like a girl with a simple nightgown on, how would I look if I put on an entire outfit? After all, it seemed that I looked better as a girl than as a boy. And that thought alone started gave me a twinge down my crotch.

The feeling of silliness and stupidity had long since left my head, and just by THINKING about wearing a full outfit I started to get another hard on.

I started separating my dad’s clothes from my mom’s clothes. I put my dad’s clothes in a big pile and then I started sorting out my mom’s clothes. I started putting the panties in one place, then the bras in another, and so on.

I was so caught up in the sorting, that suddenly the phone rang and it scared the hell out of me. I felt as if I had been caught. But I calmed down, and picked it up.

“Hello?” I found myself saying. My voice seemed almost distant.

“Hi, honey”. It was mom again.

“Hi, mom. How’s everything?”

“We just got here. Traffic was terrible. We’re still going to be here for a while. Don’t wait up. But I wanted to ask you, have you started washing the clothes, yet?”

I felt as if she had a video camera hidden somewhere and she had seen my entire act. I closed my eyes, and answered, expecting the worst.

“Uhm… No, not yet. I was playing video games and time kind of…”

“Oh, fabulous” she interrupted, without even letting me finish the sentence. “I forgot to mention something important. Before you turn on the washing machine, you have to separate all my pantyhose. There’s a special bag hanging next to the washing machine. Put my pantyhose in that bag before starting to wash them, otherwise you’ll ruin them. Okay?”

“Sure mom. No problem. Bag next to the washer. Pantyhose. Got it.”

“Honey, I’m sorry for making you do this, but I promise I’ll make it up to you. Bye”. And with that, she hung up without even waiting for me to answer back.

I looked around and saw my mom’s clothes spread out all over the floor of the bedroom. I started picking up each piece of clothing and I would feel it with my hands. Then I’d rub it against my chest. I had an incredible boner and I figured this was the best time of my life.

When I got to her panties, something struck me. It was the smell. The crotch had a strong smell to them. At first I found it somewhat pungent and disgusting. The crotch had these little yellowish-brown stains that had this very strong odor.

But I started getting used to the smell rather quick. Then it hit me: that’s my MOM’S SMELL. That’s what my mom’s pussy smells like. That thought almost made me have an orgasm right there, and suddenly I started finding the smell very pleasant an arousing.

Excited at the notion of having her pussy next to my cock, I immediately put on her silky, nylon white panties.

My penis made it look like a circus tent, but the feeling of the panties hugging my ass was more than anything I could ever imagine. I rushed over to the bras, picked out a white, lace bra and started fumbling with it. Being my first time, it felt as if it took me forever, but I finally got it on straight. Then I moved on to the pantyhose. I picked a regular, taupe-colored hose and I sat on the bed. At first, I tried to put my foot inside as if I were putting on a pair of pants. But I quickly realized that was not going to work. I remembered watching movies where girls would put on pantyhose by rolling them up, first. So I started rolling each leg, and as I started putting the pantyhose on, my legs started to shake uncontrollably.

I was excited beyond words. This was my real sexual awakening, and I didn’t want it to end. By the time I pulled the pantyhose on, I was so aroused that I had an orgasm right there. I dropped to the floor and started shaking. The idea of my semen in contact with my mom’s pussy-smell was too much.

I cried out in complete rapture. I was in heaven. I felt as if I had fucked my mom.

Once again, I lay there, on the floor, wearing a bra, panties and nylon pantyhose. I couldn’t move, and my body was shuddering. I felt as if I had no strength left in me. Then that feeling began again. It was a feeling of remorse. I felt stupid. I felt silly. I felt like a fucking pervert. I was ashamed of myself, and I wanted to get rid of those clothes and wear my own.

But I was too weak to get up. Even now, as I look back on this, I believe I may have fainted briefly on account of the incredible orgasm I felt.

It took me so long to sit up, that by the time I sat on the bed, the feeling of silliness was gone, and once again I was comfortable wearing the bra and pantyhose. I looked at the clock on the bedside table, thinking that my parents would come through the door any minute. But to my great surprise, only two hours had passed since they had left! I still had all night to continue experimenting with this new, fantastic thrill of wearing my mom’s clothes.

My penis was completely drained. It was small and flaccid. The panties and pantyhose were drenched in my semen. I decided to remove those and put on another pair.

I grabbed another pair of panties. These were a gentle tone of ivory. Before putting them on, I took a great whiff at the crotch. Oh, yes. There it was: my mother’s smell. I even stuck my tongue and licked it. It was salty and delicious.

I put on these new panties, and went for another pair of pantyhose. My dick was still spent and I couldn’t get an erection. Because it was so small at the moment, when I finished putting on the pantyhose I looked FLAT. I looked at myself in the mirror, and there she was again: this young girl in her underwear.

I was so excited that I felt I had to finish the outfit. I picked a white, satin blouse and started buttoning it all the way to the top. It was the first time I noticed that women’s clothes have the buttons on the opposite side. So it took me a while to button it up, but I finally managed.

Then came the final touch. I grabbed a black, rayon, pleated skirt that came about an inch above my knees. As it turns out, I was almost the same waist size as my mom. She was still a little bit slimmer, so the skirt was a bit snug. But when I finished putting it on, the skirt forced my waist in, and the illusion was perfect: I WAS A GIRL!.

I rushed over to the closet and put on a pair of black, leather pumps. When I returned to the mirror, the vision was perplexing. I was a girl. I didn’t have a drop of makeup on, and my hair was short and styled as a boy. But with my hair all mussed as it was and my soft, 13-year old features, I DEFINITELY looked like a 15 year old girl.

I didn’t want this to end. I kept rubbing my cock, but I had had three incredible orgasms (one in which I had fainted) it simply wouldn’t react. Since I couldn’t jack off, and I didn’t want this to end, and I still had a lot of time before my parents arrived, I decided to remain in my mom’s clothes for the rest of the evening.

I picked up my dad’s clothes, and suddenly I realized how rough and heavy men’s clothes are. I dumped them inside the washing machine, then I started picking up the rest of my mom’s dirty clothes. I put the pantyhose I wasn’t wearing in the nylon, net bag hanging by the washing machine, then I went to the kitchen to fix myself something to eat.

It was 11:30 PM and I started fixing a sandwich. Before I realized it, I had gotten so used to my new clothes, that they felt RIGHT. They felt GREAT. My cock started to move once again, and after I had my sandwich and had cleaned the dishes, I returned to my porno channels.

Only this time, as I started rubbing my hardening cock watching porno flicks, I started getting aroused by imagining I was the girl getting fucked in those shows. Very quickly I had another extraordinary orgasm, and once again, that silly feeling washed over me. Once again, I felt like a fucking pervert and looking at myself in that skirt made me sick. But this time, I knew that all I had to do was get used to it, and in a few minutes, that feeling would disappear and my body would feel wonderful covered in women’s clothes.

I changed channels and turned the TV off, then I went over to the washing machine and took off my mom’s clothes. My dick actually hurt from all those wonderful orgasms. I put the rest of the clothes in the washer, then I went to my room, put my pajamas on, got in bed and drifted into a heavy, restful sleep.

CHAPTER 2
A Transvestite is Born

The following morning I woke up with a wonderful feeling over me. I felt as if I had something to look forward to in my life. I literally sprang out of bed and went into the shower.

My cock still hurt a little and I had a sore groin from those extraordinary orgasms. But I felt invigorated. My mind was racing with all kinds of thoughts and emotions.

Was I really a freak? Do all kids go through what I had gone through the night before? Was I a pervert for getting aroused by my mom’s smell?

But at the same time, the idea of going through another dress up session filled me with eager anticipation.

I really hadn’t noticed how empty and lonely my life was up to that point. I barely had any friends. I never went out. All I did was watch TV, surf the net and play video games.

Suddenly, I had something to look forward to every afternoon. Dressing up in women’s clothes was a revelation to me. I wanted to walk into my mom’s closet to pick out the clothes I would wear to school. But I knew that was impossible.

I dressed quickly and went downstairs to have breakfast. My parents were still in their bedroom. Apparently, they had arrived pretty late, and they were still asleep.

I went to the fridge and poured myself a glass of orange juice. As I sat down and started drinking it, my mom came into the kitchen. She kissed me lightly on my head and started fixing some coffee.

She looked spent.

“’Morning, mom,” I said cheerfully. I was feeling fantastic. I couldn’t wait to get home that evening and go through her closet to try on some more of her clothes.

“You’re quite cheerful this morning.” She replied making an effort to stay awake.

“Do you want me to help you? You look beat.”

“We got home at 2:00 AM last night. I’ve hardly slept.”

I got up and started making the coffee for her.

“I’ll do that.” I grabbed the pot from her hand, and started filling it with water. She simply sat down and put her head across the table.

“Ooooh. I’m so tired.” She spread over the kitchen table and closed her eyes.

As I made the coffee, I would look at her from time to time, and I would notice how her nightgown would cling to her figure. I noticed how the nightgown would hug her at the waist and hips, but how the skirt flowed down. Her breasts were supple and firm and filled the top of the nightgown beautifully. As she turned her head over her arm, her weight shifted and I caught a glimpse of her nipples.

I started to get an erection and blushed. I felt embarrassed and ashamed. What was wrong with me? Was I falling in love with my own mother? That was sick. I knew it was wrong. But I couldn’t keep my eyes away from her.

I knew it was really dangerous. What If she opened her eyes and caught me staring at her breasts with a huge hard-on? I would spend the rest of my childhood in therapy. So I snapped out of it and put a cup of coffee in front of her.

“Thanks sweetheart” she simply said without even opening her eyes. “Have a good day at school, today.”

“Thanks. Bye, mom”. I ran out of the kitchen and went outside towards the bus stop.

As I sat on the bus, I knew my life had changed and it would never be the same. Everything felt and looked different. Suddenly I realized that I was staring a lot at girls. But I was looking at how their clothes fit. I checked the different styles of skirts, blouses and pants.

As I looked out the window into the street, I was noticing which women were wearing pants, which ones were wearing skirts, which ones were wearing dresses. I noticed if they were wearing pantyhose or had their legs bare. I would notice which ones had make up on and which ones didn’t.

Suddenly, I was noticing everything about women. How they wore their hair. How they wore their makeup. And I realized that I was noticing all these things to try and recreate them later that evening when I was home alone.

When I got to school, suddenly I was aware of every single girl around me. I saw how the skirts would cling to their waist, but drape down their legs. I would notice the way they walk, they way they move, and how their clothes would respond and sometimes enhance their movements.

The rest of the day was a blur. I didn’t pay attention to any of my classes, and all I wanted to do was to race home and try on some dresses.

After what seemed like an endless day, I arrived home at 3:00 PM to find mom waiting for me in the kitchen. She was wearing a green, plaid, pleated skirt with tall, black boots and a green turtleneck sweater that enhanced her breasts.

“Hi mom.” I tossed my backpack in the living room and went into the kitchen to kiss her hello.

“Hi, honey. Can I talk to you for a minute?” She asked in a very serious tone.

I froze. For a minute, I thought she had somehow noticed that her clothes had my semen, or something like that. My heart sank.

“Here. Sit down. Can I get you something to eat?” I wanted to die.

“No, I’m fine. What’s wrong?” I asked almost pleadingly.

“Nothing. I just wanted to talk to you about some things.”. I started to relax. “I wanted to thank you for helping me out last night with the laundry. And this morning with the coffee”. I was all ears. “It seems that you’re growing up really fast. Sometimes it’s tough on a mom to realize that her little boy is becoming a teenager. It makes her feel old.”

“You’re not old. Quite the opposite. You look great!” I found myself hitting on my mom, and she didn’t even realize it.

“Thanks, honey. But I was thinking that maybe you could help me out more around the house. You’re home a lot, and I got all these activities at your school and at the community center. If you could continue to help me with the laundry and cleaning up, I would really appreciate it”.

“Sure. No problem”. I was beside myself. Outwardly, I was calm and in control, but inside I was thinking to myself; “wow! Unlimited access to all her clothes every day with no interference”.

“Just don’t let it get in the way of your homework”.

“Don’t worry. I won’t.” I was feeling incredible. I was so glad and was so falling in love with her, that I decided to probe her to see how she’d feel if she knew I wore her clothes.

“You know, mom. I wanted to ask you something.”

“What is it?” She was genuinely intrigued and was giving me her full attention.

“Well, it’s kind of weird.” She frowned. “On the bus ride home, I heard these kids talking behind me. One of them was saying how she caught her brother dressed in his mom’s clothes last night. Then they found a bunch of love letters all addressed to his mother saying how much he loved her. The girl said that the entire family is in shock and they don’t know what to do with that kid.”

“Oh, my God. How terrible! Who is it?” she asked. Her face was in real shock.

“I don’t know. Just some kid at school, I guess.”

“That’s awful. They should put him in a psychiatric institution. That boy is sick. Imagine falling in love with his own mother… And wearing her clothes too. I only thank God that you’re normal. I don’t know what I’d do if I found you in my dresses.”

My heart sank. “Yeah. Imagine that…”. I was heartbroken. I couldn’t tell her what I had done, nor what I wanted to do. I couldn’t share my feelings about her. But at least I knew where I stood. I would have to be extra careful about my cross-dressing. “I wanted to tell you about it because I thought it was too weird.”

“It’s not weird. It’s sick. It’s perverted. It’s wrong. I can’t think of anything more repulsive than a man in woman’s clothing. And a son in love with his mother? Oh, God. I want to throw up. Whoever they are, please stay away from them, okay? Bye, honey. I’ll be back at six to start fixing dinner.”

She kissed me and left me sitting there. I was really sad. But at the same time that conversation snapped me back to reality. I decided to cope with the fact that I would never have my mom, but at least I could have her clothes.

With that, I went upstairs, and took off all my clothes, moving into her closet. I needed to make sure that last night’s events were not a dream.

I opened the panties drawer and pulled out a pair of white, satin panties and put them on immediately. Then I found a matching bra and I fumbled with it until I put it on. Then I opened the drawer were the stockings were and I pulled out a pair of taupe, nylon pantyhose. All of the feelings from the previous night rushed in and once again I found myself in heaven.

From there, I moved onto where the clothes were hanging neatly in racks. I started to look at everything, one by one, and finally chose to wear a pistachio green suit. That suit had a mini skirt and a jacket. I went to where the blouses were and I picked a white, spandex turtleneck blouse.

There was a pair of green pumps that I put on after that. I looked at myself in the mirror, and the girl was there again. Only this time, I felt that I really needed to put on some makeup.

I went to the dresser and started to put on some mascara and some lipstick. When I finished, I definitely looked like a young girl trying to imitate her mom.

I knew I didn’t have as much time as last night, and proceeded to jack off. Once again, the orgasm was fabulous. And once again, as soon as it was over, I got that weird feeling over me. Suddenly I felt like I looked stupid. Stupid and sick and perverted and my mom’s words seemed to ring true.

To distract myself, I fought off the impulse of taking off the clothes and wiping off the makeup, and instead I went into the den and started doing my homework. And just as I expected, a few minutes later, I found myself totally comfortable in my outfit once again.

I spent the rest of the afternoon dressed in that green suit until I looked at the clock. It was 5:30 PM. Mom would be coming home soon. I went into her bedroom, went into the hamper, and took out the panties she had worn at the party last night. Her wonderful smell was there. And as I ran my tongue over the crotch, I rubbed my hard cock against the skirt until I exploded in a tremendous and enrapturing orgasm that almost made me faint again.

I realized that the awkward feeling that came right after my orgasms was helpful so I could actually get these wonderful clothes off. Otherwise, I wouldn’t have minded getting caught.

As I started to take off the suit I noticed in horror that I hadn’t worn any protection, and that the panties and pantyhose were wet with my cum. I put the green suit away and ran into my room to hide the bra, panties and hose. I started to get dressed in my own clothes, and just as I was tying the laces of my shoes I heard the front door open and my mom walk in.

“Honey, I’m home. Would you give me a hand fixing dinner?”

“Sure thing, mom.” I made sure no tales of the make up were visible, then I went downstairs to help my mom with dinner.

As of that day, I knew my life would never be the same. I had to accept that I was a cross dresser. I enjoyed dressing in my mom’s clothes. And I also lusted after my mother. I found her to be the sexiest creature on earth and more than anything I wanted to penetrate her pussy with my cock.

But for now, I would have to accept the fact that she would never be mine and that the closest I’d get to her pussy, would be to lick the crotch of her used panties. After all, she had put me in charge of them. I couldn’t think of anything more rewarding.

As I walked down the stairs to help her with dinner I felt happy to face this new phase in my life. The years to come would be full of excitement and exploration.

But little did I realize, that this path would lead me into a future that I never imagined in my wildest dreams could be possible. It would put me face to face with my real sexuality.

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.

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.

CHAPTER 5
A Son’s Farewell

That summer I spent with John at Martha’s Vineyard was the last time I would be in control of my own life. But at the time, I didn’t know it.

When I returned home, I simply spent one week packing to leave for Chicago where I would be starting college in the fall. It was now late July and I had a lot of things to do before fall term began. As a graduation present, my parents gave me a brand-new car, so I packed, said my farewells and drove off to Chicago.

Just as I was about to leave, I found myself alone with mom in the living room. Dad had gone back upstairs after wishing me luck and mom was staring at me with a guilty look in her face.

“Honey, I’m sorry I neglected you all these years. I know I was very wrapped up in my things and you must’ve been very lonely staying home... alone.”

“It’s okay mom. I really didn’t mind”. I actually meant it. I was thinking that if I had spent more time with her, I would’ve eventually made a move on her or I would’ve revealed my little secret to her and tragedy would ensue. For now, I had to keep my secrets to myself and enjoy her presence these last few moments. She looked very hot. She was wearing tight black pants that accentuated her figure and a pink, Halston, silk top.

“I should’ve given up all those stupid activities that kept me from spending more time with you. I feel like I don’t know you anymore. Your friends, your interests, your girlfriends... if you even had any of them.”

As she mentioned the word “girlfriends” I looked away. I was never interested in any girl... except for her. And I didn’t want her to know that.

“I’m sorry, Ashton. I promise I’ll make it up to you...” She walked over and hugged me. It was a magic moment. She was vulnerable and opening up to me and I was more attracted to her than ever before. As I felt her breasts push against my chest and the softness of the silk against my hands, I got a huge erection. It was beyond my control. Every fiber in my body wanted to kiss her and fuck her brains out on the couch. I obviously had to restrain myself, but despite every thought of restraint, I put my arms around her and held her tight. As I pressed her against me, my dick pushed against her crotch and my hands began to make their way down her back to her ass. I reached her butts and I began to cup her ass as I slowly turned my lips and kissed her softly behind the ear.

To my huge surprise, she let out a grunt of pleasure. She closed her eyes and slowly began to turn her head. I closed my eyes and made my way to her face. I wasn’t thinking anymore. I was letting my inner feelings take over. So I ran my lips over her face until I found her mouth. By now, she was letting herself enjoy the moment. Our lips met and we fused in a passionate, deep, long kiss. Our tongues would play with each other in loving embrace. My hand made its way and cupped her breast. She sighed in pleasure and my dick got harder so I pushed my pelvis against her, dry-humping her pussy. But suddenly, she freaked out, pulled back and stared at me. I was helpless. I couldn’t hide my feelings anymore. I guess she must’ve seen right through me, because suddenly she blushed and ran upstairs without saying another word.

I felt dumbstruck. I couldn’t move. Everything felt weird. Without saying a single word, and with a simple gesture of love and lust, I had revealed my true feelings for her. I was totally embarrassed and the situation had turned awkward. Should I go upstairs and talk about it? Or should I simply go, let things cool down, then talk to her on the phone? I chose the latter, and simply walked out the door.

Little did I know that it would be the last time my mom would see me the way I was. Little did I know that I was about to die… and be reborn.

On the car ride I kept going over the incident in my head. When I felt her firm, supple breasts against my flat chest I pulled her in and at that moment she didn’t pull away. Then I moved my hands down her back and cupped her ass, and she didn’t move away, either! In fact, now that I was thinking about it, she was responding to my touch. It wasn’t until I pushed my dick into her pussy that she backed away. And then she blushed! SHE BLUSHED! That meant that she ENJOYED IT! She wanted more. And she knew that I wanted more.

I wanted to turn the car around and go back home, but I knew that was impossible. I mean, what about dad? How would I explain it to him? I just had to keep driving to college.

A day later I arrived in Chicago, and before the week was up, I was already settling into my new apartment. I eagerly called home. The excuse was to give my parents my phone number. But I really wanted to talk to mom. I was hoping she would pick up the phone. Sure enough, Mom answered the phone. Although several days had passed, the situation was still awkward between us.

“Mom, I... I want to explain something.” I said.

“Look, Ashton. There’s no need. Really. I know your dad and I have grown apart over the years and I haven’t had sex in a while, and I may be a little... confused. I don’t know. I don’t know if I sent any signals out to you that you may have mis...understood. I certainly didn’t mean to. But I... I... felt... you...” She sighed, “Oh, my God. I... felt your... against me. It felt so hard... And the worse thing is that I have missed it so much that I... But you’re my son and it’s so wrong...” Suddenly she started crying over the phone. “But I don’t want to ever discuss that again. Understand? Never. It was a brief moment. It was wrong. It’s sick. It’s so wrong that I can’t even begin to tell you why it’s so wrong on so many levels. So let’s leave it at that. Maybe it’s best that you moved out to college now.”

“Mom, please. I can explain. Really.” I pleaded with her.

“No. Some things are better left unsaid. I said I never want to talk about this again. You’re my son and I love you. But not like that. I hope you respect that. I’ll see you for Thanksgiving... maybe. Good bye, SON.” Then she hung up and the line went dead.

I hung up the phone. I put my face in my hands. I felt awful. It was like I had been caught crossdressing. Thank God that part of me was still safe. I knew that after revealing my feelings for her, mom would distance herself from me. But if she knew I was a crossdresser, I’d lose her for good. To distract myself from these thoughts I began unpacking.

As you might’ve guessed, I had stolen a few dresses from John’s house, and I still had my mom’s old dresses. I couldn’t wait to wear them all the time in the privacy of my own apartment. Nevertheless, as I was still settling in, and had various people coming in and out of my apartment (such as the cable guy, the phone co., etc.) I exercised some level of self control before indulging in my private habits.

That summer was particularly hot, and as much as I wanted to shave my body, I chose to wait for a couple of months, otherwise, I wouldn’t be able to wear Bermuda shorts or swimsuits without getting weird stares or having to provide needless explanations to strangers.

By the beginning of my second week, my apartment was beginning to look half-way decent. My special clothes had been hidden behind a wood panel in my closet and most of my regular clothes had been put away.

The cardboard boxes had been thrown away and aside from a few books, magazines and dishes, I was finally settling down into my new college life. I was two weeks away from the first day of class, and mostly I had been going to the university to register, and get most of the info I would need for the next few years.

The saturday prior to my first day in college, I was so tired from the move, that I ordered a pizza. I sat down in front of my TV. ready and started eating my mushroom and pepperoni with double cheese. I was half-way through my third slice, when the phone rang.

“Hello?”

“Hi, buddy! How are you doing?”, the voice came from the other end.

“John?”, I asked in disbelief.

“Hey! You still remember me! I’m touched!”, he said jokingly.

“Hi. It’s great to hear from you. Are you looking for my dad?”

“No. I know your dad is back East. I just saw him a couple of days ago. He’s the one who gave me your number. Actually, I’m in town, and I was wondering if you’d like to join me for dinner”.

“Yeah, sure. That’d be great”.

“Terrific! I’ll pick you up in 20 minutes.”.

“Okay”. I changed my tee shirt and put on a pair of jeans, then put the rest of the pizza away and waited for John. I was really glad to know he was coming over. I had been alone for so long, that I welcomed the company of a good friend.

A few minutes later John came by and we went to a nice restaurant in downtown Chicago. During dinner, John explained to me that he was in town for a quick business trip, but that he had found out where I was and he thought it would be a good idea to spend the weekend together. Naturally, I agreed, thinking it would be a great way to spend some time before I started classes.

After dinner, John invited me over to his fancy home for a drink, and once again, I had no reason to refuse. In fact, it would be a welcome change of scenery.

His Chicago estate was huge. In fact it had a small bungalow on end of the property. The house had a swimming pool, tennis courts and huge gardens that were perfectly groomed.

By the end of the evening, after we had shared a great time together, he suggested that I stay the night in the bungalow. I was so tired that I agreed. He walked me over and quickly showed me where everything was, then he excused himself and I crashed on the bed. I was so tired, that I didn’t even get under the covers, I simply drifted into a heavy, restful sleep.

CHAPTER 6
The First Day of the Rest of my Life

The next morning I woke up around 9:30 AM. I stirred around in bed trying to catch my bearings. I stretched around, then walked over to the window and opened the curtains to see John’s house during the day.

The place was palatial. The bungalow was located across a huge yard. To enter the bungalow, you first had to go through a metal gate inside the compound. That gate was on the far end of the swimming pool, giving the bungalow complete independence from the main house.

The bungalow had a small living room with a 32 inch TV, stereo and DVD, a kitchen, a patio and a phone. It had a small, one-car garage and there was a door that led to the street. It was, in fact, like a small apartment inside the property.

As I checked out my surroundings, the phone next to the bed rang. I jumped on the bed and picked it up.

“Hello?”

“Good morning. Good to see you’re up. Are you hungry?”

“Yeah. As a matter of fact, I am. But I was just wondering where to go to get some.”

John laughed at the other end of the line. “Don’t worry. I’ll come right over and bring you a tray”.

The line clicked, and the phone went dead. I hung up and I turned on the TV to see what was on. Most of the channels had been blocked, except the gay porno channels, Cosmo, Hallmark and a few others like Discovery Health.

A few minutes later, John walked in with a tray, and two DVD’s. He was wearing sweats and had a big smile on his face. He was as cheery as I had ever seen him. He greeted me warmly and set the breakfast tray on the kitchen table. Then he took one DVD and moved over to the living room. As he turned on the television he asked me to join him.

“Sorry. But before we eat there’s something I want you to see. And I also need to talk to you about a couple of things.”

I sat down in front of the television set, but before he turned it on, he looked a me. His smile faded, and although his eyes were still warm, he went very serious. He looked straight at me as he spoke.

“You know why I divorced my second wife?”, I simply shook my head softly. “The fucking bitch cheated on me. And you know with whom?” I shook my head again. “She was screwing the pool guy. The fucking pool guy. Some spic who hardly spoke any English. Can you believe that?”

“I’m sorry, John. But I see you’ve...” he put his hand up interrupting me.

“Do you have any idea at how pissed off I was? Some greasy wetback was trying to make a fool out of me. He thought he could get away with it. But I showed him.”

I was starting to get worried. John was suddenly very dark and sinister. Not at all the guy I was used to hang out with. He continued.

“That really scarred me. Now, I don’t trust women. Not a single fucking one. They’re all whores trying to milk me for every penny I’ve got. On the other hand, I’m not queer. And I don’t get hard-ons thinking about guys, you know? So what do I do now? I really didn’t know. Until that day at Martha’s Vineyard.”

My heart sank. The mention of Martha’s Vineyard made me very uneasy. He noticed the look on my face, then he smiled.

“Don’t worry. Everything’s fine. Trust me. I know I sound mad, but you shouldn’t have to worry. I’m not mad at you. I’m mad at them. But that morning at my place, when you put on my wife’s dress I got an idea.”

Oh, shit! He KNEW. He had seen me. I felt completely naked. Terror struck me, and I guess he saw it on my face.

“Don’t be afraid. Relax. Just hear me out. Anyway, when I saw you in that dress I got an idea. Women are whores. And I’m not into guys. But what if I could make a woman of my own? Someone I could trust? Someone I KNEW was not after my money, but who really liked me for who I am, and not for the money I own.”

I simply stared at him with a blank look in my face. What the hell was he talking about?

“And that’s where you come in. Seeing you in that dress caught me by surprise. I mean, it did fit you nicely, and you seemed to enjoy wearing it. Besides, I know you started wearing her underwear all the time you were there.”

I covered my face with my hands, and all I could say was, “Shit. I’m sorry. Let me try to explain. See…” But he interrupted me again.

“Buddy, I don’t give a shit. What matters is, that after that I checked you out. You’ve never had a girlfriend. Never. By your own admission, you’ve never been laid. And you look at me with droopy-dog eyes. I don’t know if you’re gay, per se. But I believe that you might be a woman in a man’s body. I like you. I really do. I think we hit it off great over the summer. I didn’t think of you sexually, but you were good company to hang out with. You weren’t sucking up to me or trying to get to my money. So, as far as I can tell: you don’t have a girlfriend, you’ve never been laid, and you wear women’s clothes. I think you may be a woman in a man’s body.”

“What? NO! Look, John. It’s not like that. Really. I swear. It’s just that I…”

“Please. Sit down and shut up.” His voice was commanding. It was hard not to do as he said. “Just answer me this, okay? And I’ll know if you’re bullshitting me. How long have you been dressing up?”

He stared at me, drilling me with his eyes. I was dumbfounded. I couldn’t think. “Since I was 13”.

“See? I knew it! I bet you anything you want that I’m right! You ARE a chick in a guy’s body”.

“John, please.” He wasn’t even listening to anything I said.

“So here’s what we’re going to do. I’m going to help you find your true self. I’m going to help you bring that woman OUT! Okay?”

“No. It’s not okay. I’m not a woman! I’m a man! I may have some unusual sexual needs, but then again, who doesn’t? I won’t do it!”.

Suddenly, John stood up. His smile had faded, and his eyes turned icy-cold. I started to shiver.

“Ashton, I want you to shut the fuck up and listen to me very carefully. I’m a very wealthy, powerful and influential man. And I’m really, really pissed. If you refuse me, I swear you’ll regret it.”

I tried pleading with him. “John, “ I started in a begging tone, “you have to believe me. I don’t see myself as a woman. I’m a man. In fact, if I’m to be completely honest, I want to fuck my own mom. In fact, I started to make a move on her. I want to see if she’ll have me. I’m a sick person. I need help, not dresses.”

John was very serious and started speaking in a icy tone. “Listen Ashton, the life you knew, the life you were living… is OVER. As of today. As of right now. It’s gone. You have two choices: one, you can become a woman. My woman. Fashioned after what I think a woman should be. Surrounded by riches and wealth and with everything you want, simply a phone call away. Or two: you may go to jail. You will be arrested and convicted for the murder of Hector Andujar, a pool cleaner who was shot dead a few days ago. The police will find uncontested evidence of your involvement of the crime, and you will spend the next 20 years on death row before you get a lethal injection. Is that clear?”

He went over to the television set and popped in a DVD. The screen filled out with a black and white picture of a surveillance camera. The room on the screen was the room I had used on Martha’s Vineyard.

“When I found out my wife was cheating on me, I put these surveillance cameras to get evidence for our divorce hearing.” John said calmly.

As I looked at the screen, my heart sank. The figure on the screen was not his wife. It was ME. I was putting on dresses and masturbating in them. I would wear panties and bras underneath my clothes. All was captured on camera.

I closed my eyes and dropped on the couch. John pushed stop and eject. Then he put the other disc inside. What I saw, shocked me even worse. A Hispanic guy entered the room and sat on the bed waiting for someone. Then another figure entered the room. It was a man dressed in the same dress I was wearing. In fact, he looked a lot like me. He raised a gun, and shot the Hispanic guy twice. Then he masturbated, JUST LIKE ME, and left the room.

It looked as if I had put on a dress and shot that guy on the bed. John turned around and saw my face.

“Pretty convincing, eh? It looks like you shot Hector. And if you’re wondering about fingerprints, last night as you were sleeping, I came inside and put the gun to your hand.”

I couldn’t believe it. I was being framed by one of the richest men in the country. Possibly in the world.

“You see, Ashton. I already took care of my ex-wife. She’s now working as a two-bit cocktail waitress in some sleazy dive a few miles north of Las Vegas. She gets fucked by every Tom, Dick and Harry and barely makes minimum wage. But Hector was different. He’s an illegal. I couldn’t destroy his life because his life is pretty pathetic anyway. So I had him killed. And seeing you in my wife’s clothes inspired me to do it this way.”

“But, what about college? My parents?”

“Don’t worry about that. I can’t have that guy running around with the knowledge that he murdered some spic on my orders. He could have me framed. So I’ll take care of him too. He will have a car accident… IN YOUR CAR. He will be wearing your clothes and he’ll have your ID on him and I can assure you the police will conclude it was you who died in that car.”

He removed the other DVD and sat down next to me.

“So, the question now comes back to you. You may choose to go back to your appartment and get arrested within a few hours, after which you will be humiliated in front of everyone you know and will end up getting fucked up the ass for 20 years before getting a lethal injection, or you can stay here and live a new life. I promise you a life of absolute comfort and unimaginable wealth.”

I simply sat there. My mind was racing in a million directions. I couldn’t think clearly.

“Why don’t you have breakfast? Calm down. Think about it. I’ll be back in an hour and you can tell me what you chose.”

John got up and left, taking his videos with him. I just sat there staring at the blank television screen. My entire life had come crashing down, and I didn’t know what to do.

CHAPTER 7
The End of Manhood

I felt as if several hours had passed. But in fact, only one had gone by after John had dropped that bomb on me. I couldn’t eat a bite, and the omelet and toast simply sat there untouched. I held my head between my hands, feeling a burning sensation in the pit of my belly. My mouth was dry and I couldn’t think.

Suddenly, the door opened and John came back. He had two bottles of pills, a yellow manila envelope and a small suitcase.

“So, have you made up your mind, yet? The clock is ticking and I need an answer now.”

I turned around to face him. I was pale and terrified.

“John, please. I…”

“Ashton, I’m getting really tired. If you don’t give me an answer now, I’m going to throw you out into the street. Then I’m going to call the Chicago P.D. and deliver the tapes, the panties soiled with your semen and the gun. How long do you think it’ll take them to pick you up?”

“Please don’t. Really, I…”

“So you want to stay?”

“No, I mean yes… I mean…” I broke down and started crying. John was unmoved by my tears.

“Another confirmation of your true self, Ash. Real men don’t cry. They stand up. They fight. If you would’ve fought me, at least I would’ve doubted my original theory. But this display…”

I simply sat there and sobbed.

“Okay. That’s it. Get out. Just start getting used to the idea of getting arrested. Get used to the idea of being exhibited in court as a homosexual transvestite who shot his lover. Get used to the idea of getting wildly fucked up the ass for the rest of your soon-to-be short life in prison.”

He started going for the phone.

“NO! Please!” I cried. “I’ll do it! I’ll stay!”

John put the phone down and smiled at me. “I knew you would make the right choice”.

I slumped on the couch. I was drained. Defeated. But I figured I’d buy some time and figure out a way out later. For now, I had to avoid prison.

John sat next to me. “Okay. Here’s the deal. You’ll live here. Alone. I will tell the servants that you’re a college student working on some research project and they are not to disturb you. They will only drop off your meals by the porch. Leave the tray outside as soon as you finish.”

He stood up and put on a thin, cotton glove, then extended his open palm at me. “Now, I need your wallet.”

I reached into my back pocket and slowly handed it to him. He then took out a small plastic bag and sealed my wallet inside. Then he took a piece of paper out of the manila envelope and handed me a pen. “Now sign this. Don’t bother reading it, just sign it”.

I took the pen, and started reading it. “I said, don’t bother reading it. Just SIGN the fucking paper!” I stopped reading and signed it. I only caught a glimpse of the first few lines. It was a letter addressed to some doctor at John Hopkins Hospital. He took the paper and placed it in the envelope again.

“Okay, good. Now, pay attention because this is very important. As of this minute, you’re no longer Ashton. You’re Ashley. Got it? Start getting used to your new name.”

“What are you going to do with me?”

John smiled. “You got it wrong. It’s not what I’m going to do with you. It’s what I’m going to do TO you.”

I simply stared at him with a blank look on my face. He went on to explain in detail.

“Your transformation… or shall we say… your blossoming into womanhood will take place in three stages. Stage one will begin right now. You will undergo a rigorous diet and exercise agenda and you will begin an aggressive hormone therapy program.” He put the pills on the kitchen table, opened them and took a pill from each bottle. “You will take one of these with every meal for the next six months. Starting today. In fact, starting right now.”

He went over to the kitchen and poured me a small glass of water. Then he gave me the pills. I held them in my shaking hands.

“Take them. Go on. It’s with every meal.”

I couldn’t do it. I couldn’t bring myself to taking them. Suddenly he yelled at me, “TAKE THE FUCKING PILLS, NOW!”. I was so scared, that I popped the pills in my mouth and drank the water.

I almost choked as I asked what kind of hormones they were. He answered quickly, “they’re a new brand of concentrated hormones. One of my pharmaceutical companies is working on the protocol. They give these to women in fertility programs. They are more easily and rapidly metastasized into your system. It's not magic of anything. It's just a new generation of hormones. Not synthetic, actually. They have natural ingredients. Anyway... the eggheads at the lab told me how they work and they're supposed to work faster and safer. The other pill is a testosterone-inhibitor, so your transformation will be even quicker.

“Now. Stage one will last about six months. We will begin to mold and shape your body naturally as much as we can. You’re 18. That’s a good age. Your body will begin to adjust to its new hormones quite rapidly. But after six months, that’s as much as your body will change in a natural way. That’s when we will begin stage two.

“Stage two will involve your first set of surgeries. I will evaluate your breast, waist and hip size and will adjust them accordingly. We will begin with breast augmentation surgery. I will give you *B* or C-size cups depending on how your body responds to treatment.”

The burning sensation in the pit of my stomach bolted again. My mouth was parched, even though I had just taken a glass of water and my hands were sweating beyond belief. I was terrified. I was going to be deformed! He was going to give me tits! I would be forced to wear bras for the rest of my life!

“Don’t look so scared. I guarantee you’ll beg for them after six months. Furthermore, I’d like you to have a 26 inch waist. If after your exercise and hormone therapies you don’t get one, the second surgery will involve the removal or your lower ribs and liposuction around your waist area to give you with a beautiful and sexy hourglass shape”.

My eyes started watering again, and I started sobbing.

John gave me a warm smile and continued. “Finally, we will remove your Adam’s apple and tighten your vocal chords to provide you with a higher-pitch voice.

“A few months after stage two’s surgeries have healed completely and no tissue scarring remains, we will move on to stage three.” He stopped and looked at me with those steely-ice-cold eyes.

“What’s stage three?” I asked stupidly.

“I think you know what it is. You just signed an application for sex reassignment surgery at John Hopkins. Your testicles will be removed and you will have a vaginoplasty performed. You will, in fact, become a full-woman. I have a bunch of shrinks and doctors on my payroll. They'll have all the necessary documentation. But just in case you try to expose this little... research program, I'd really like to see how you explain your signature on a real, LEGAL, sex-reassignment-surgery application."

I felt dizzy. I was about to pass out. I was trying to swallow, but my mouth and throat were totally dry.

“Approximately one year from today, you will be a woman. My woman. And I expect you to behave as one.”

I started hyperventilating. I was going to be castrated! My dick was going to be sliced open!

“Don’t be so dramatic. I guarantee you’ll enjoy it.” He walked over to the bed and opened the small suitcase. He pulled out a bunch of sport bras and thongs along with some pink, cotton uniforms, lycra gym clothes for women and a few panties.

“These will be your clothes for the next six months. You will wake up at 7;00 AM every day.” He pulled out a DVD from the suitcase. “Then you will follow these exercise routines to the letter.” He pulled out a second DVD. “Then you will learn to apply make-up, and learn the basic concepts of female fashion: accessories, jewelry, hair styles… the works!” He proceeded to take out a bunch of magazines: Cosmo, Vanity Fair, etc.

“I… please, John.” I stammered.

He didn’t even notice me. He simply continued. “Right now, I want you to stand up.” I complied. “Now strip.”

“What?”

“You heard me. Strip. To your bare ass.”

I slowly took off all my clothes. I stood there, completely naked in front of him. I shyly cupped my dick and my balls in a feeble attempt at holding on to some shred of dignity. John went back inside the suitcase and extracted a small leather bag. He handed it over to me.

“Take this bag and go and take a shower. As you shower, I want you to shave every follicle of hair on your body, except your face. After you shave, you will use hot wax and tweezers and you will remove every single beard on your face. I’ll be back in an hour and we’ll pick it up from there.”

As I stretched out my hand to grab the bag, I revealed my balls. John looked at them and raised his eyebrows. Then he smiled and gave me an “ok” sign with his hand. Then he picked up my clothes, and disappeared behind the door.

As I stood there, cold, naked and terrified, I couldn’t help feeling completely at a loss. For years, I had wanted to dress full-time as a woman. But this was going too far. Nevertheless, John’s little remark at my balls didn’t go unnoticed. My dick stirred, and before I knew it, I had a hard-on. I helplessly felt my manhood slipping away between my legs, and the more I thought of myself as a woman, the harder my dick got…

There I was, standing completely naked. Stripped of all dignity. Stripped of my manhood. And yet, I was sexually aroused at a man complimenting my genitals.

I sat down for a moment and looked inside the bag. There was a lady razor along with lady shaving gel, a Nair waxing kit and a pair or tweezers. I took out the pink razor and stared at it. How long had I waited to do this again. But now I was afraid I would lose myself and be forever gone if I did it.

I knew I had no choice. One way or another I was trapped. I summoned all my strength and moved into the shower, I turned the hot water on and stepped in. I let the water wash over me. I felt dirty. Used. Violated. The water was a welcome relief.

As I let the water run down my naked body, I blocked out any thought and concentrated on the feeling the water provided. I pressed the button on the gel can and the sweet, strawberry-smell filled my nostrils. At once, my dick reacted and began to get hard. I closed my eyes, and began lathering my chest. I turned off the water then I put the razor against my chest, and gave a firm stroke. There was a rustling sound. Then I looked down and saw the shaved track in the middle of my chest. My dick began throbbing. I rinsed the razor, and looking straight at my chest, I took the blade cartridge against my skin, and moved it again. The rustling sound of the hairs being shaved sent pangs of ecstasy down to my throbbing cock.

I took a deep breath and looked down. My chest was beginning to strip of any hair. I rinsed, took another deep breath and shaved again. This time, as I heard the rustling of the hairs being shaved, my left hand moved down and grabbed my throbbing cock. I started to rub it gently as I rinsed the razor again.

Another rustling sound and my legs started to shake. I opened my eyes and took another deep breath. Two thirds of my chest were still covered in sweet-smelling lather. But one third was bare. Nice and clean. I took the razor back to my chest and shaved another strip. The rustling sound made me sigh in deep anticipation. I was masturbating strongly now. I looked down, and my chest looked like a 50-50 bar. I frantically started to shave the rest of my chest as I stroked my cock.

Before I had finished, I burst with an orgasm I hadn’t felt in a long time. My legs buckled and I almost fell inside the shower. My left hand was filled with my cum and my right hand held a razor full of lather and chest hair. By now, my chest was shaven. No more hair on it.

At once I felt sick. That guilt-ridden feeling I got after an orgasm was back, but it was much stronger now and all I could think of, was that I was going to get castrated. I was going to have my penis cut open and scraped. I was going to get breast implants. And here I was, jacking off. That awkward sensation returned and I was pissed at myself. How could I possibly enjoy this shit if I was going to be changed forever? I didn’t want to become a woman. I wanted to fuck my mom’s brains out.

I turned the shower back on and rinsed my left hand. Then I leaned against the wall as I let the water hit me in the back of my head. I felt ridiculous. I turned off the water and sat down on the floor of the shower. I put my head between my arms and I started to cry again.

As I calmed down, I felt the water droplets run down my bare chest. They felt nice. Almost sensual. I looked at my chest. It wasn’t quite as smooth as i first thought. There were still small traces of body hair. I ran my fingers down my chest and it felt a little like peach-fuzz. I took the razor, and without thinking I started fine-shaving those areas. As i concentrated on the task the awkward feeling disappeared and suddenly I wanted to have an extra smooth shave for the rest of my body. I wanted that lovely feeling of nylon stockings against my bare legs.

I stepped out of the shower and went over to the kitchen. I looked under the sink, and there was a small bucket. I filled it half-way with warm water, then I returned to the shower and sat down again. I was still drenched from the shower as I lathered up again using the gel. The sweet smell of ladies’ shaving gel filled me up and I started to enjoy it again.

My cock was spent, but I was feeling very excited. I started shaving rapidly, rinsing the razor inside the bucket after each stroke. In a few minutes, my entire body was as lean and smooth as a baby’s butt. No short hairs remaining.

I toweled dry and looked inside the suitcase. There was a jar of moisturizing cream which I opened. The sweet smell kept me completely aroused. My cock’s strength was returning slowly and I started to apply the cream all over my body, especially in the belly and groin area. There was also talcum powder with I immediately applied in my groin. My earlier experiences with shaving had taught me to moisturize that area or i would suffer a bad case of chaffing.

The feeling of my soft, smooth skin sent chills down my spine as my cock started to get hard again. I dropped on the bed and started jacking off again. This time it took longer, but my cream-filled hands felt awesome against my cock and I came again in a rapture of bliss. Although I had very little semen coming out of me, I was so wrapped up in my female personification ecstasy that it seemed like the orgasm lasted for minutes.

I lay there, spent and weak. My head hurt. I hadn’t eaten anything and I was thirsty as hell. I started to get that strange after-orgasm feeling again. I felt ridiculous and silly. To distract myself, I got up and I went over to the kitchen. I drank the orange juice with one gulp. Then I sat down for a while.

Everything felt surreal. I was totally naked with a shaved body inside a strange house. I was frightened as hell that I was going to have my dick and my balls cut off. But at the same time, it seemed unreal. as if it wouldn’t happen for a long time, yet. So I started to relax a bit.

I went inside the leather suitcase and got the Nair waxing kit out. Curiously I started to read the instructions as I examined the contents. I forgot about the fact that I was naked -- and shaved. The awkward feeling had dissipated and now I was deep into learning how to wax my face. As I was reading, unconsciously I shifted on the chair and crossed my legs -- ladylike. The sensation of my shaved legs, one against the other, began exciting me immediately. I wanted that feeling for my face, too.

I opened the wax jar and placed it inside the microwave. Then I applied a strip of hot wax on my face. At first it burned. But as it cooled, it felt nice. Then I tore it off and yelled in pain.

I looked at the strip and I noticed that I had torn the beards from its roots. I looked at my face in the mirror and I noticed a red stripe of skin where the wax tore off the beard.

I took a deep breath and waxed the rest of my face. Each time I pulled the strip I was hit by an intense pain. But after I finished, my face felt unbelievably soft. Softer than any close shave I had ever given myself. The problem was that my entire face underneath my nose was blood-red. I knew that would disappear in a couple of days. In the meantime, I took the tweezers and fine-plucked any remaining beards left behind.

The door opened and John came back. As I heard him walk in the room, I instinctively grabbed a towel to cover my body. Without realizing it, I had pulled the towel over my chest... just like a girl would... A question that still remains to this day is this: was I embarrassed to be seen in a shaven body, or was I starting to revert to my female self? Even today, as I look back I keep wondering why I covered my chest with that towel that morning...

“I knew it. Underneath, you’re a true woman”, he said. I sat on the toilet seat, clutching to the towel. Feeling humiliated. John simply said, “get up. Let me look at you.”

I stood up, still holding on to the towel. With his eyes John ordered me to drop it. His gaze was very commanding and cold. I had no choice but to obey. I dropped the towel. John grabbed his chin as he examined me.

“Very good. Very smooth. No nicks or cuts. You’re very good at it”, he said as his eyes ran up and down my body. I was still covering my dick. “Let me see your dick”. Slowly I removed my hands. John shook his head. “You didn’t shave there. Get in the shower and finish up. I don’t want a bushy area. In fact, give yourself a French wax”.

He left for the kitchen. Slowly I put a strip of how wax right above my dick. I pulled on it and screamed in pain and terror. John came running in and started laughing at me.

“I can’t do it. It hurts too much!” I pleaded.

John walked over and looked at my genitals. “Mmmm. Very soft. Let me help”.

He picked up the wax kit and I yelled “no!” but he went ahead and applied a second strip. He held me back and then ripped it out. I screamed and writhed in pain holding my waxed area. Tears were rolling down my face. John smiled. But in the midst of all that pain, having his hands so near my genitals had an arousing effect. As the pain began to subside, my dick started to get hard. John simply whispered, “patience, my dear. Soon you will fully enjoy the touch of a man...” With those words he tore another strip. I almost came, but I rolled around the bed screaming in pain. This went on until my genital area was totally smooth and free of any hair.

“There you go. See? Isn’t that better?”

All I could say was, “I need the lotion so I don’t get a rash”.

“Let me. I’ll do it”. John grabbed the body lotion and approached me. Without thinking, he put some lotion on his hands and began spreading it around my crotch. As his hands were spreading the lotion, he said very nonchalantly, “Don’t think that I’m gay, or anything. You’re my woman. I’m simply getting to know you a little better. I don’t want any surprises later on.”

As John touched my groin, the feeling in my gut got stronger. It was a warm feeling spreading through my belly. It was not uncomfortable. Actually it was a wonderful feeling of pleasure that started filling me up. I was trying very hard not to react, but for some reason, every time his hand came near my dick or my balls, I wanted those hands to hold my balls or to hold my dick. I tried to fight that feeling with all my strength, but naturally, my dick started to respond. By the time he finished, I was blushing from the huge boner. John stood up and slowly approached me. He whispered into my ear, “I knew you found me attractive. I can’t wait for you to have a pussy so I can fuck your brains out every night”.

There was a feeling of sickness in the pit of my stomach, but at the same time I also enjoyed the words. Having someone find me attractive was a first in my life. No one had ever said that to me. The fact that it was a guy didn’t matter very much at the time.

He slapped me gently on my butt and walked outside. As he left the room he said, “Get dressed and try out your new clothes. Put on a set and hang the rest in the closet. I’ll come back to check on you shortly.” Then he left.

I raced over to the suitcase. I wanted to put some clothes on. It didn’t matter if they were woman’s clothes. The humility of being naked in front of someone of great power, was unbearable. It had been so long since I had stripped that it felt like I had been naked for days... but only one hour had passed.

I pulled out a set of pink, cotton sweats and a white, lycra sleeveless shirt. I didn’t put on any panties of bras. I felt sick. I wanted to wear the least, feminine clothes at the time.

As I pulled the pants over my legs, I couldn’t help feel the soft, cotton fabric on my bare legs. As upset as I was at the situation, it felt good. I put on the shirt then I stared at myself in the mirror.

The clothes fit very snug. As slim as I was, I didn’t have a female shape at all. It was square, like a man. There was a bulge in my crotch that made me very self-conscious. I tried to reduce it as much as I could, but without any panties, it was difficult.

I took off the pants and put on a pair of white panties. They were pink, g-strings. They hardly covered my balls and my dick but it helped me a bit to push my dick and my balls back. Then I put the pants on again. They only came half-way down my calves, so part of my shaved leg was visible.

I looked up, and you could see my nipples through the white, lycra shirt. The touch of lycra against my nipples made them hard. I didn’t want John to think that I was horny or anything. That also made me self conscious, so in the end, I wound up putting on a sports bra to cover my nipples. Then, to cover the sports bra, I put on the sweats’ jacket. The sweats had a soft, pink tone that was very feminine.

There was still a bulge in my crotch and the clothes were very snug around my hips, thighs, chest and arms. I wasn’t fat, by any means. But my figure was a far cry from a girl’s figure.

I went over to the bed to sit down. As I walked, the g-string would ride up the crack of my butt. I felt silly and ridiculous. I lied in bed and started to cry.

CHAPTER 8
The Woman Inside Begins to Awaken

I must’ve lied there for about an hour. I has helpless. I was depressed. I was full of fear and anxiety. I felt the chilly morning air hit my naked, shaved calves. Every time I stirred or moved, I felt the g-string ride up my ass or my dick and balls shift in my crotch. I wanted to stay very still.

Suddenly, John came back. He had a few dumbbells and other female exercise equipment. He dropped the equipment and went over to the kitchen.

“You didn’t touch your breakfast,” he said in a dry voice. “I want you to keep your strength.” Then he smiled and his tone lightened. “But... I understand this has been a very emotional day. So, I guess we won’t be as strict. Just don’t let it happen again. I want you to have your three meals every day.” He went serious again. “I’ll know if you’re not eating”.

He walked over to the bed and sat down next to me. I lied there, with a blank expression staring into the ceiling. Slowly, he placed his hand on my thigh. I reacted and turned away from him.

Very calmly, he said, “Don’t reject me. I understand today is a special day. A difficult day for you. There’s a lot you have to take in. But don’t disappoint me. Or I’ll throw you out on the street right fucking now.”

I sat up and looked at him. His eyes were cold and scary. I was very afraid. I looked down and softly said, “Sorry.”

“That’s better. Now get started on your orientation videos. You got a lot of work to do. I have to leave now. But don’t worry. You’ll be taken care of. If you need anything, just pick up the phone. Someone will make sure you get what you need.”

“What if I need to contact you?” I asked. John smiled.

“Just pick up the phone and ask for me. They’ll direct the call to wherever I am.” He got up and looked straight at me. “It’s nice to know you’ll think of me when I’m away...”. I didn’t really think that way. I was just wondering what would I do if something in the house breaks down or something. But the fact that he felt I was thinking of him, made me blush for a moment and I felt a hot flash in the pit of my stomach.

He held my chin gently, then left. I dropped back on the bed and stared at the ceiling. The thought of my castration sent chills through my spine. I closed my eyes and tried to get the thought off my head. To distract myself, I figured it would be better to look at the videos. That would help me calm down so I could think more clearly. I thought that if I was calm, i would be able to figure out a way to get out of this mess.

Slowly I got out of bed. The sweat suit was very tight. The g-string was very uncomfortable. I kept pulling it out of the crack of my ass. I sat down in front of the television and popped a disc into the DVD player.

It was an exercise series. It showed how to do pilates, aerobic dancing... the works. Obviously these exercises were designed for women. I ejected that disc and popped in another. This one was about how to apply make up. I kept putting discs in the DVD player to check them out. All of them dealt with women things: exercising, accessoricing, hair, make-up, fashion, etc. There were a bunch of taped shows on pregnancies, hormone imbalances in women, mood swings, menopause... etc.

I turned it off and walked over to the trackmaster. I got on it and started running. i guess I must’ve ran for about 30 mins. I was out of breath and covered in sweat. I took advantage of that and took off the cotton sweats and the g-string and took a shower.

I must admit, that the water felt great running down my body. But when I got out of the shower and back into the bedroom, I had chills shoot down my spine. On the bed, there was a pink and gray, spandex suit with pink tennis shoes and a white, sleeveless dry-fit women’s top. I kept looking around for cameras. How in the hell did anyone get inside?

The phone rang. It startled me. I picked it up, and a female voice on the other end, simply said, “our orders are to attend you at all times. Your clothes are ready. Would you care for anything to drink?” I simply said, “no, thanks”, and hung up.

I was scared shitless. I was being watched all the time. I had to do what they said. I started to put on the spandex suit. The sheer feeling of the fabric clung to my legs and body. It started to give me a hard-on. But my crotch looked like a circus tent. I tried to cover it up, unsuccessfully. So I turned on the television and started to work out again, in an effort to tire my body into submission.

And so it began, my slow pace into establishing a routine that would dominate my life for the next six months.

Now, the thing about living in a routine is that you lose your sense of time. Every day my routine began as follows: I would wake up at 6:00 AM and I would run 7 miles on the trackmaster. Then I would shower and change my sweats. I would have a light breakfast and I would take my pills. Then i would exercise with Pilates or another body-shaping routine until 11:00 AM.

After that, I would start on the make-up videos. I had been self-taugh for many years, and I was no stranger to applying makeup. But the videos gave me the direction and expertise I lacked. It showed me how to combine colors and styles depending on the social situation involved. It’s not the same to wear makeup to the office or to an informal gathering. So I would sit at my dresser and I would begin to follow instructions. I would apply makeup, then take it off for about two hours. There was a part in the videos about plucking and shaping eyebrows. That is the only thing I didn’t do. I guess I was trying to hold on to any shred of manhood I could.

At that time, my lunch would appear at the door. Usually a light lunch made up of salads and low-fat food. I would take it along with my hormones. I must admit, that not thinking about it, made it easier for me to take them.

in the afternoons I would look at the DVD’s about fashion and accessories. Around 6:00 PM my dinner would appear at the door. Again, low-fat. Again, with my pills.

The rest of the evening I spent watching TV. Only a few channels were available: Hallmark, Cosmo, etc. Mostly women’s networks. I watched those shows until i would fall asleep around 10:30 PM.

Settling down into my routine gave me a small sense of security. I kept thinking to myself, “I have to figure out a way out of this.” But I kept distracting myself with the daily agendas of working out and learning all I could about how to look and how to behave as a woman. And since in a routine you lose your sense of time, I kept thinking that sooner or later I would be able to figure out an end to my predicament. But time simply passed. And I really didn’t think of anything i could do.

I didn’t have any full-bodied mirrors, so I couldn’t really see myself begin to change. I started to lose weight really fast, with the low-fat food and exercise. And the hormones were also working fast on me. At first, I had to shave my body every two or three days. As the days passed on, I started to shave once every week. I noticed my balls were shriveling and my dick was getting smaller. The g-strings weren’t as uncomfortable to wear as before. Also, my skin had become extremely soft, silky and smooth. My hair, which was long enough to begin with, was also growing longer and longer. it took me longer to blow-dry every day and it kept getting on my face. So I started to wear a pony tail to get it out of the way.

About a month into my regime, I got a surprise visit from a masseuse. I was getting out of the shower and suddenly there she was, standing in the middle of my bedroom.

“Hi.” she said. “I was asked to give you an exfoliation treatment and a body-shaping massage”.

I was stunned. I hadn’t seen anyone in a month, and suddenly, this hot chick was standing in front of me. Instinctively, I tried to cover myself. She simply smiled and pointed at her massage table.

I got on, and she started to massage me. I could feel her hands all over my butt, my legs, my back and my arms. It felt really good. I was aroused, but the hormones were working on me, and my dick wouldn’t get too hard. It stirred, but when it got hard, let’s say it was like a... soft erection. I was a little alarmed at first, but since I could still get an erection, I simply figured I was a little thrown by the surprise of a girl in my bedroom.

I didn’t know this at the time, but she was helping the hormones spread fatty tissue around my hips and into my butt, and away from my upper back and waist.

I tried to start a conversation with her. i wanted to know if she would help me out of my mess. But she remained quiet. She never answered back. The only thing she said was:

“John sent you this little present.” She opened her hands and showed me a pair of pearl earrings. “He wants you to wear them starting today. Have a nice day, sweetheart. He also told me you would be getting a body-shaping massage every week. So I’ll guess I’ll see you next week.” She dropped the earrings on my nightstand and walked away.

“Wait. Please.” She stopped and turned around to look at me. “Listen, I... It’s just that... You see, the thing about me and John...”

She interrupted. “I’m totally aware of your arrangement with John. He spoke with me at length before I came here. I’ve been in John’s payroll for five years now. If you’re wondering if I can help you out of here, you’re wrong. John made me. He gave me all my rich clients. He can break me if I do something he disapproves. So... no. I can’t help. But I look forward to see you next week.”

I couldn’t think of anything to say, so I simply watched her leave. Then I put the earrings on. It had been a while since I had pierced my ears, so the holes had begun to close up again. After I put the earrings on, it was a bit painful and there was a little blood. But I let them stay on my ears.

My routine went on for months. Every week this gorgeous girl would walk in and give me a massage. As hard as i tried to strike a conversation with her, she kept quiet and simply gave me a massage. She wouldn’t speak to me at all. In fact, if she wasn’t massaging me, she would hardly look at me.

With such a gradual change over an extended period of time and with no mirrors, I really didn’t notice the changes my body was going through. The only way for me to know that something was happening, was because the clothes, that were very snug when I first put them on, now felt comfortable and weren’t tight at all.

I did notice that my nipples were getting larger and my chest tingled. It was hard for me to notice at first, but as the days moved on, every time I put on my sports bra or tank top, they would feel more and more sensitive to the touch of fabric. And the tingling made it feel as if they were growing. But since it was so gradual, I wasn’t really noticing the growth of my breasts. Maybe I did, but I tried to fool myself into thinking everything was all right. And since the sport bra would push them in, that would give me confidence that everything was still normal.But I did notice that my dick wouldn’t get hard, even if I was aroused by something on the television. That scared me a lot. My dick was still sensitive. If I rubbed it, it felt nice. But it simply wouldn’t get hard. That worried me a lot. And I kept reassuring myself that it was the result of the stress I was under.

Another thing that I noticed was that my hips and butt were growing. I kept bumping into the edge of tables and furniture with my hips. The reason for this is, that we are used to our bodies. Unconsciously, we measure the distance between our extremities (hands, legs, etc.) and the objects around us. I hadn’t noticed how my waist had slimmed and my hips had expanded (in large part, thanks to the massages) until I started to bump into things.

And my hair was now shoulder-length. It was long enough to try different styles that the videos taught me. And I got into mood swings very often. I cried at commercials and got pissed off in a flash.

It’s important to mention one thing: my sex drive had gone really low. You see, when you begin a hormone treatment your body experiences an important shift in its development. Sex drive is regulated by testosterone. Since i hardly produced any, I had a very low sex drive. And even if I got aroused, that’s the reason my dick wouldn’t get hard anymore. So the shaving, waxing, makeup and hairstyling began to look normal instead of becoming the focus of my sexual escapades.

The routine and enclosed space eliminated any sense of time for me. I didn’t know if it had been two months or one year since the beginning of my “treatment”.

The only thing that told me how much time was passing, was when I would catch a mention of the date on TV.

And so it went. Slowly, but efficiently my body was changing. But I still felt like myself.

Until one day. When John returned. That was the day I stopped being a man. That was the day I realized, that without knowing, I had become a woman.

CHAPTER 9
Ashton is dead. Long live Ashley

I hadn’t realized that six months had gone by. So one morning, I got out of the shower, just like every day, and to my big surprise I ran into John. He was sitting on my bed. When I entered the room he stood up. I guess he was taken back by what he saw, because he simply stared at me for a long time without saying anything.

“Holy shit...” he whispered. “You look like...” but he never ended the phrase. He was speechless.

“Hi, John. It’s really great to see you again”. After all what he was putting me through, it was still good to see a familiar face and have a conversation. I mean, it had been six months and the only person I saw was a beautiful masseuse who wouldn’t speak to me once a week.

John snapped back to reality. “Listen, Ash. I need to talk to you. Let’s sit for a moment”. John’s voice was strangely warm. Like when we were friends. It was almost... apologetic.

We moved to the kitchen and sat at the table. This day, there were two trays and we started to have breakfast together.

“Look, Ashton...” I was taken by surprise. He was using MY name. None of this “Ashley” crap. “...It’s been six months since we started, and a lot has happened to me since then. I’m really sorry I put you through this hell. I was angry and irrational. I felt humiliated by my wife and his lover and I did things I’m not proud of.” i looked at him with great interest.

“So it finally dawned on me: I may be able to manufacture a woman... but not even I can tell her how to feel. And the last thing I want next to me is someone who is resentful and hateful towards me. She may not take my money. But I don’t want a ‘Lorena Bobbit’ next to me... if you know what I mean.” His words made me stop eating. He went on, “Love is a feeling that has to be given freely. It can’t be forced, or coerced. And in the end I love you. Not romantically. But as a friend. I actually miss you. I miss our conversations... the time we’ve spent together. So, after all this time, I have come to a decision. You may choose your life. Your choice. Not mine.”

John stood up and walked me over to the bedroom. On top of the bed, were two sets of clothes. On one side, were my old white tee shirt, boxers, jeans and tennis shoes. On the other side, was a pair of black panties, sheer, transparent black pantyhose, a black, lace bra, a black angora, turtle neck sweater, a gray, cashmere, pleated mini skirt with a large black belt and a pair of black, patent leather, high heeled boots. And on the corner of the bedroom, stood a large, full-length mirror.

I looked at the clothes, dumbfounded and only held my pink terrycloth robe tighter against my chest. John looked at me and gave me a warm, friendly smile.

“You may choose your life. No pressure. If you want, you can be Ashton again. I will do everything I can to restore your life. I’ll start you on a testosterone hormone program to return you to your old self. And we’ll figure something out so we can bring you back to life. No strings attached. Or you can move on to become Ashley. Whatever. But if you decide to move on, it will be YOUR decision. Not mine. Not anymore.”

I looked at John. I was in shock. I couldn’t speak. John kept his warm, friendly smile. He put his arm over my shoulder and said, “I’m giving you back your freedom. Whatever you choose, I’ll support you.”

He released me and started for the door. “Put on your clothes once you have chosen and meet me in the main house. I have a business associate coming over in about an hour to talk business. You may join us for drinks and... whatever, and after he leaves, we’ll figure out what to do with the choice you made”. He smiled at me and left.

I was standing by the door, looking at the clothes on the bed. But as soon as I heard John walk away, I threw away the robe and raced for my own clothes. I was overcome with joy! The nightmare was over! I could go home!

But the joy was extremely short-lived. As soon as I put on my boxers and jeans I was overcome with fear. I had lost so much weight, that the elastic on my boxers could barely hold on to my waist. My jeans were so loose, that I had to hold them in a grip with one hand to keep them from falling.

I tried to put on my tee shirt with one hand, but i couldn’t. So I let go of my pants... which immediately fell around my ankles. I put on my white tee shirt and I was struck with horror: I had tits! Small, but there they were. You could see them through my tee shirt, especially the enlarged nipples. I had to pull the shirt away to hide them. I pulled up my pants and waddled my way to the mirror. I looked ridiculous. I was trying to pull my shirt away from my chest with one hand and I had to hold my pants up with the other hand. My extremely long hair kept falling over my face because I kept looking down to hide my new tits. i looked stupid and I felt totally awkward and out of place.

I sat back on the bed. I looked down. I could see the lumps on my tee shirt. I hadn’t noticed how much my tits had grown with the hormones, because the sports bras are usually very snug around the breast area. But the tee shirt allowed them to fly loose and... there they were.

I couldn’t think straight. I had been terrified to lose my dick and my balls. But now that I had the chance to go back to that life, here I was even more afraid to return. I looked at my face in the mirror. I was completely androgynous. I was no longer a man. But I wasn’t completely a woman. I was stuck in the middle. No home. No life. Just the memory of my mom... and how I still wanted to make love to her. I wondered how she’d feel if she saw me now. Six months had passed since I made my move on her, and now I was completely terrified if she saw me. I had been evicted from my life. Ashton didn't have anything in his life to look forward to: a mother who would reject him, a father who would definitely cut him off... or even kill him... No place at the university. No job... Nothing.

I closed my eyes and began to cry. I didn’t know what to do.

Slowly I opened my eyes and looked over to the other side of the bed. I saw the skirt, blouse, panties and bra. I stood up and my pants and boxers dropped to my ankles. I walked over to the other side and saw myself in the mirror.

The tee shirt just barely hid my crotch. It looked like a gown. I looked at myself and I immediately saw the femininity I had grown into. I kept looking at the clothes. Then, without thinking, I took off the tee shirt and grabbed the panties. I felt the exquisite, silk through my fingers. I held it up between my hands to look at its shape. The clothes were new. The store tags were still attached. With my teeth, I broke off the tag and slipped into the panties.

My dick had shrunk so small and my balls had shriveled so much, that the panties actually fit nicely. There was a small lump, but it was hardly protruding. I stood up and ran my hands down my butt. The panties felt wonderful.

Then I took the bra. Again, I snapped the tags away and examined it. The soft, silky feel of the cups was incredible. it was a push-up bra. I put it on and looked at my breasts. The nipples were incredibly sensitive and I felt pangs of delight run through my body as my nipples grazed the bra... and they looked great. Small, but no need to pad the bra. They filled it up nicely. It was for A sized breasts, but being a push-up bra, it gave them more shape and volume.

Then I opened the pantyhose and began slipping my legs into them. I had almost forgotten how much I loved the feeling of pantyhose against my legs. And the fact that my legs were smooth, and toned made them look even better.

Then I grabbed the angora sweater. I tore away the store tags and looked at it. It was very feminine and beautiful. But it seemed to me that it was too small for me. I looked at myself, and without realizing it, I had closed my legs by putting my knees together... just like a girl. That made me very horny. My dick wouldn’t get hard anymore, but as I rubbed it, it still retained sensitivity and it felt good. I kept rubbing my crotch imagining how John and any other man who saw me would want to fuck me. That made me even hornier and I kept rubbing harder. I rubbed and I rubbed until I came. I hardly had any cum left inside. In fact, only a few drops came out onto the panties. But the orgasm was fantastic. It was an orgasm that I had never felt before in my life. Not even the pleasure of my first orgasm as a crossdresser compared to what I had experienced. It felt as if it lasted for hours. I felt pleasure shocks throughout my body, not just in my crotch. I had almost forgotten how I craved orgasms. I hadn’t had one in six months. And this one seemed to make up for that lost time.

Then, the most amazing thing happened. I didn’t have any awkward feelings in me after my orgasm. If you remember, when I used to wear my mom’s clothes or John’s ex-wives' clothes, and I came inside of them, I used to feel ridiculous. That is, because I’d think that if a girl would walk in and see me, she’d never want to fuck me and I’d never live down her opinion that I was a sick, gay freak.

But now, I couldn’t fuck a girl, even if she begged me. I had tits. My body was shaven. I had been consumed with femeninity around me for six months and now it felt normal. So instead of feeling awkward and uncomfortable, I simply felt very relaxed. My horny impulse had subsided. I slumped on the bed, breathing heavily. I could see my newly-formed tits heaving under the bra. It was strange, but I didn’t feel scared. I didn’t feel awkward. I simply felt... satisfied.

A few minutes had gone by, but I felt it had been hours. I sat back up and put on the sweater. I was amazed to see how well it fit, considering that it was a size 2. It was nice and snug, without being too tight and it heightened my breasts. With the push-up bra, it almost seemed like I was a size B.

Then I stood up and grabbed the skirt. I examined it for a moment. The pattern, the pleats, the texture. It was a cotton/rayon blend. Smooth and almost silky. I slipped it on and fastened it. Again, to my surprise, it was a perfect fit. It wasn’t snug or tight. It was just right. Then I grabbed the belt and tried it on. It was a bit snug around the waist, but it wasn’t tight or uncomfortable. Actually, it helped slim my waist even further, making me look more feminine.

Finally, I sat back down and grabbed the patent leather, black boots. They were shiny and feminine. I put my right foot and began zipping it up. The silky lining felt wonderful against my panty-hosed leg. Then I put the left one on and stood up. I took a few steps back to look at myself in full-length the mirror but I wanted it to be a surprise, so I kept my eyes looking down.

Slowly, I raised my head and looked at the reflection in the mirror. When I saw it... I lost my breath. Across from me, inside that mirror, stood a beautiful woman. I remembered my first time in my mom’s bedroom when I tried on her gown and this pretty 13-year old girl had stared back at me. Today, that 13 year old girl had blossomed into a gorgeous woman.

There were no traces of my masculinity. The reflection in the mirror could never be mistaken for a cross dresser. The frame was smaller, the hips were larger, the face was smoother... It was a WOMAN. But it was weird, because it was a woman with MY face on it. It was still my face. But it was a female face.

The feeling went beyond incredible. That image had surpassed my wildest cross-dressing dreams. And suddenly, i found myself wanting MORE. I raced to my dresser and began plucking and shaping my eyebrows. Then I applied makeup: base, eye-shadow, eye-liner, mascara, lipstick...

Then I grabbed the blow dryer and began styling my hair as I had learned to do so in the videos I had been watching for six months. Finally, I put my pearl earrings on and stepped back in front of the mirror. I was in such a shock from that vision, that my legs actually buckled and I fell on the bed. I felt incredibly emotional at the vision of the beautiful young woman staring back across the mirror. I wanted to cry. But at the same time, I didn’t want to ruin my makeup.

Slowly, I stood up again. I turned around trying to look at myself from every angle. The skirt looked fabulous. It made my legs look incredible. The entire outfit felt like paradise. It was just my size. It wasn’t uncomfortable at all. Then I looked at my old clothes lying on the floor. I walked over and picked them up. I stared at them for a while. Then I remembered what I looked like in them. I looked awkward. Like a little girl trying on her daddy’s clothes. Slowly, but surely, this new feeling started inside of me. It was as if... now, my old clothes were the cross-dressing clothes. As I saw myself in the mirror, my female self felt and looked more natural than ever. Suddenly I felt repulsed at my male clothes. I felt... angry at myself for being such a coward. As Ashton, I had been a coward in facing the world. I kept hiding behind video games and the internet. And I used any excuse I could to stay home... inside a closet. Not socializing. Not doing much of anything. A feeling of hatred against myself began. but it wasn't at myself. Not anymore. It was at Ashton.

I went to the kitchen and pulled out a large, sharp knife. I raised the pants and began thrashing away with the knife until I had them reduced to shreds. Then the tee shirt and boxers followed.

I took a black, garbage plastic bag and threw the shreds inside. Then I walked back into my room to see myself in the mirror again. As I enjoyed my reflection, I kept thinking... Ashton is dead. I started to hate the name “Ashton”. It didn’t feel right anymore. The more I looked into myself I kept thinking, “Ashley”. Then I realized that my addam’s apple was still there. I was a little self-conscious about it. I pulled the turtleneck a little higher to try to hide it. I raised my skirt and looked at the tiny lump in my crotch. I wanted it cut out. Then I ran my hands through my breasts... It felt so good I wanted them to be bigger.

Six months ago, I was terrified at the notion of getting tits and having my dick and balls cut off. But John was right, back then. Now... I couldn’t wait. I wanted to beg for it. The more I thought about that, the more I realized that Ashton was indeed... dead. Now it was Ashley’s turn to take on the world. As that thought raced through my head, I found out wanting to be MORE of a woman. I wanted to share that womanhood with the rest of the world. Especially, with the man i admired most in the world... the one who had set me on this path. The man who had such an extraordinary vision or me, who knew me better than I knew myself, that I realized I was falling in love with him. I smiled and said in a low voice, “my dear John... get ready for the time of your life”.

I raced out the bungalow into the world. Ready to show the world who I really was. Ready to become the woman I always wanted to be.

CHAPTER 10
Meet Ashley

As I walked out into the world again, I was in an emotional high. It was now mid-January, and the weather was cold. But I didn’t feel cold. I felt ecstatic. As I walked down the garden path that led towards the main house, I tried to catch a glimpse of me anywhere I could... in the swimming pool reflection, in any bay window I passed... etc.

I was enjoying being outdoors. It was like a drug. The wind was hitting my face and playing with my hair. It seemed like the colors were brighter. I felt free. Renewed.... reborn.

But as I approached the main entrance, I started to feel extremely nervous. After all, I had never been dressed as a woman in the presence of anyone else. The incident with the cheerleader uniform in the locker room and Martha’s Vineyard don’t count, because I was HIDING. But I had never been dressed as a woman in a public, social event. And that thought crept into my head as I approached the door.

I stopped at the door wondering what should I do? Should I go back to the bungalow and wait for John? Should I go inside and just go with the flow? I was nervous and scared, but at the same time I was ecstatic and confused. All at once. Up to this point in my life I had been Ashton. The minute someone else saw me like this... there would be no turning back.

Suddenly the door opened. It was one of the cleaning ladies. She startled me. I froze. She simply came out of the house carrying a broom and a dustpan.

“Excuse me,” she said casually as she walked into the garden. I just stared at her. She hadn’t reacted strangely. She didn’t stare at me. Except that she suddenly stopped and turned around to look at me. I thought... “here it goes... she knows I’m really a guy and she’ll say something...”. But instead, she simply said, “It’s awful cold out here, miss. Maybe you would be more comfortable inside.” Then she smiled and walked away.

Her words began echoing in my head... “miss”... I took a deep breath then relaxed. A soothing feeling washed over me. It gave me strength. it gave me courage. So I stopped fidgeting, opened the door and walked inside.

It was the first time I stepped into the main house. I didn’t know which way to go. So I started to make my way across the hall towards the living room. I could hear John’s voice coming from there. I stopped quickly by a mirror hanging near the entrance and checked my hair and makeup. I still couldn’t get over myself how pretty and feminine I looked. I kept staring at my eyes. They were still MY eyes. But the rest of my face had become the face of a girl. I took a deep breath and made my way into the living room.

John was standing by the bar pouring himself a drink. Sitting on a chair, was his business associate. A tall, black, former NBA player called Kevin. They were talking shop... something about investment banking, stocks and stuff like that. But as soon as I came into the living room, Kevin suddenly fell silent. John looked up and suddenly he fell silent in mid-sentence. He was so taken by surprise, he actually froze. He didn’t notice that he was still pouring whisky into the glass and it was spilling over the bar.

There was a deafening silence hanging on the living room. Both men simply stared at me. Kevin was calm and curious as to who I was. But John looked like he had seen a ghost. His face went pale and his eyes widened like dinner plates. He quickly tried to regain control of himself. He noticed he was spilling his drink and began fumbling behind the bar. “Shit!”

I was incredibly nervous. All of my confidence suddenly flew out the window the second I realized I had become the center of attention. I tried to say something, but I became self-conscious that my voice would still sound male, so my mouth was just open and no sound came out. Finally, I was able to stutter, “I’m sorry... I didn’t mean to interrupt.”

Kevin immediately stood up to greet me. He was very tall, about 6.5 and lean. He had a Denzel Washington air about him, only taller, much taller. “That’s okay. We were finished talking about business.” His voice was deep and soft... It sounded a little like James Earl Jones.

I started to back away very shy. “I... guess I’ll leave you two alone”. Kevin suddenly looked at John. John had managed to get a grip and bolted from behind the bar towards me. “No, no. Please join us.” He grabbed me by the arm and led me into the living room towards Kevin. “Kevin. I want you to meet...” His voice trailed off as he examined me. Kevin was curiously awaiting the answer... “Yes?” he asked. John snapped out of his stupor when he heard Kevin. “Ashley! Sorry I was just... Um, she’s... my... a very special person...”.

Kevin held out his hand and I shook it. His grip was strong, but gentle. I could feel his strength through his hand. Suddenly I felt John’s hand go around my waist and I blushed. John seemed very nervous. And the way he put his arm around me when Kevin shook my hand was almost... possesive. As if he was jealous or something. He led me towards a sofa chair and invited me to sit. I sat down putting my knees together because I was very self conscious of what still lay inside between my legs.

John walked behind the bar once again. He was rapidly regaining his composure. When he talked to me, he seemed totally in control once again. “What’ll you have, Ashley?” I meekly replied, “club soda...”. John smiled as he began fixing me a drink. “Club soda? What’s the matter? Don’t you remember Martha’s Vineyard?” The memories of that summer at Martha’s Vineyard suddenly cascaded into my head and I blushed once again. John went on, “what was it that we drank that night?” I blushed. I was incredibly nervouse. I looked away and softly said, “margaritas...”.

Kevin just stared at me.I could tell right away that he was into me. But I didn’t know how John would react if I met Kevin’s gaze. So I kept avoiding eye contact with him. John handed me my drink and I started sipping it to calm down. Kevin finally asked John, “So, John. How did you to meet?”

John laughed. Then stared right into my eyes. “Well... we met last year. Through some very good friends of mine. I invited her last summer to Martha’s Vineyard. That was some summer, wasn’t it, Ash? Lot of new discoveries...”

I simply nodded. I kept drinking the club soda in order to avoid speaking. Kevin smiled and looked at both of us. “So.., are the two of you... dating? What’s the story John?”

John didn’t even look at Kevin. He kept his eyes on me. It was like he was taking in the way I looked. After all, I hadn’t given John any heads-up regarding my appearance. “I’m not sure, Kev. What do you think Ash? Are we dating?”

I looked directly at John. I had just finished a glass of club soda, but my mouth was suddenly parched. I looked at Kevin and then back at John. It was obvious that John was putting me in the spotlight and I wasn’t going to be able to sneak out of that question. I took a deep breath, put the glass aside, managed to grab on to all of the courage I could muster, and turned to Kevin.

“I’m not sure, Kevin. You see, John is a very, very special person. When I met him, I had to face some hard-fact about myself. As it turns out, John knew me better than I knew myself. I don’t know what we are... yet. But I can tell you something...” my voice trailed off, then I turned around and looked at John straight into his eyes. “I haven’t stopped thinking about him for the past six months”.

John never imagined I would face him like that. Suddenly, he was nervous again. And he had trouble swallowing. I stood up and walked towards John. His nervousness gave me the courage to push on. “I think I’ll have that Margarita after all...”. Then I slammed the empty club soda glass on the counter. As I stared into John’s eyes, I said, “what about you, Kevin? How long have you known John?”

“Since we were in college. I was the jock. He was the brains. We were roommates. So John. Ashely is your girlfriend, then? Certainly looks that way.”

John quickly regained his composure. He stared into my eyes and replied, “No. She’s not my girlfriend... yet. She’s just... a very special friend”. John put the Margarita in front of me and I drank it with one gulp. Suddenly I felt... safe. I finally relaxed. “May I have another?” John smiled and fixed the drink. I grabbed it and calmly walked back into the chair. John looked at me and winked. Kevin kept staring at me, but now, I felt safe enough to look back at him.

I looked down at my pantyhosed legs. I couldn’t believe it. Here I was in one of the most feminine outfits ever, looking like a million bucks, totally comfortable and feeling incredible. I ran my empty hand up and down my thigh totally ecstatic about the way I looked and felt. John said, “another Scotch, Kev?” “Sure!” Kevin stood up and walked over to the bar.

As John fixed Kevin his drink, I simply allowed myself to enjoy the evening. John and Kevin continued to talk about all kinds of stuff through dinner and I kept touching myself very discreetly enjoying my skirt, sweater and pantyhose. Kevin would stare at me from time to time and that would make me a little self-conscious about my makeup. So occasionally I would retouch it to feel more confident.

John would also keep staring at me. But unlike Kevin, every time John looked at me, I enjoyed it.

Kevin excused himself to go to the bathroom and John took advantage of the opportunity to finally talk to me on a more personal level. “Jesus Christ! You look amazing! I never imagined you would become such a gorgeous looking woman. I thought that you wanted to go back to...”.

“I know. But when you brought me my old clothes, suddenly they felt... wrong. I guess you were right all along.” I said.

“How do you like Kevin?” he asked.

“I think he’s great. But... he makes me a little nervous” I said. “Why?” asked John. “Well, he’s gorgeous and I don’t want him to know that I’m a... “ Suddenly, I couldn’t finish the phrase and I covered my mouth with my hands. John simply stared at me in disbelief. I couldn’t believe that I had made a reference about another man as “gorgeous”!

John said, “gorgeous? I... He... Of all the things you could’ve said, the first thing you say is ‘gorgeous’?” John suddenly stared at me without saying a word. I didn’t know what to say next. I felt exactly the same way as when I saw that video of me wearing John’s ex-wife’s clothes at Martha’s Vineyard. I tried to say something, but John simply put his hand up. A mischevious smile suddenly appeared across his face.

Kevin returned to the table. “Sorry... I had to take care of some personal phone calls. So... what were you talking about?”

“Well... “ John began to say, “it seems that Ashely has a little crush on you...”. I gasped and covered my mouth with both hands. Kevin suddenly whipped his head around to look at me. John simply smiled. Once again, his dark side had appeared. He was like a puppet master playing with me and Kevin. John looked at Kevin’s reaction. I wanted to crawl under the table and die. Then suddenly I noticed Kevin begin to blush and get very nervous. We all sat in silence.

John stood up and walked over to me. He began pulling the chair from under me, very gently but firmly as he spoke. “Excuse us for a minute, Kevin. I need to have a word with Ashley.” I stood up and literally raced out of the dining room. I could hardly look at Kevin anymore.

As John entered the next room he closed the door. I felt humiliated, angry and nervous. “Why the hell did you tell Kevin that I had a crush on him?” John suddenly grabbed me gently by the arms. Then he firmly sat me down and pinned me to the chair.

“Look. I never... and I mean NEVER imagined you would become an incredible-looking girl. Well... almost girl. I’m really, really glad you look like this. Because deep down, I know you’re mine. That means that I’m about to get my wish... the perfect woman. So don’t speak like that to me again, ok?” I calmed down and shook my head. He went on, “As I told you before, I need you to be 100% certain that this is what you want. I take it, you want to me MY woman. But... you’re not a woman yet. There’s one last test you have to pass. And your little remark gave me the perfect opportunity to put you to that test.” John backed away and sat in front of me. He smiled warmly again.

I looked at him curiously. “What are you talking about. What test?” I asked.

“You see... there is one slight problem about you becoming my girl. What if you don’t like it? I mean, I can see you enjoy looking like a woman. But... you still need to FEEL like a woman. And in the end... you’re a virgin. You’ve never had sex. Not as a boy... And certainly not as a girl... So... I want you to have sex. For the first time. I want you to have sex with Kevin. You said yourself that he’s gorgeous. So... you’ll spend the night with him. And after that... we’ll discuss the next steps. I will talk to him about what you have between your legs so you don’t have to explain anything. So... let’s go back in there.” He stood up and walked towards the living room.

I was shocked. I couldn’t move. I couldn’t say a word. I stared into space and let John’s words ring inside my head: “...I want you to have sex with Kevin...” I couldn’t believe it. How could he say something like that. As he got to the door he turned back to me. “Don’t take too long... I know I said I would support you in your decision. But like I also said, don’t cross me.”. Then he left me alone.