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…
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.
If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
And please, remember to comment, too! Thanks.