Some of my best times in life are when I’m dressed as a female and a guy’s cock is sliding in and out of my ass. I like to feel it swell and shoot its load inside me, making my ass tingle. I also like to feel a cock in my mouth as it swells and shoots and I gulp it down. My favorite position is doggie style. I love how well I’m filled in that position. I always shoot all over the bed as I’m being drilled from behind.
This all started when I was 18 and I dressed as a girl for a costume party. For some reason I liked the feel of the fabric rubbing up against my skin, and by the end of the night I was hooked. I used to sneak into my girlfriends’ stuff as I grew older, and when I started working, I began creating my own sexy wardrobe.
I’m small to start with, and people say I have feminine features anyway. Over time, I’ve learned about makeup and hairstyles, and I shave all of my body hair. I began passing as a girl in public, too.
A few years ago, my cousin was dating a guy from a nearby army base who had a friend named Chuck. One night they set me up with Chuck as a blind date. Of course my cousin knew I’m really male, and so did her boyfriend, but Chuck didn’t.
We all went out together, and my cousin helped me dress upstairs as the guys arrived and waited downstairs. I wore a baby blue dress cut mid thigh, a lace trimmed garter and sheer nylon stockings. My false boobs looked perky, and my cock was tucked under a feminine pad that was secured by a pair of powder blue panties. I wore heels to complete the ensemble.
After going to eat, we went to a club to dance. Chuck’s hands traveled freely over my body, but I strategically kept him from my crotch.
When we left the club, we went to a local Lovers’ Lane and parked. Chuck and I were in back, and my cousin was in front with her man. Eventually they took a blanket and went for a walk, leaving us alone. We began kissing and he felt my legs, caressing and rubbing them. I loved how his hands felt on my nylon covered skin.
Before I could stop him, his hand was on my crotch. I explained the pad by telling him I was on my period. Then I felt his huge cock and said it must be difficult to be so excited and need release. I let him guide my head down to his now exposed cock and began to open my mouth. I licked and kissed it briefly, then opened my mouth totally and began giving him the best blowjob I knew how.
My head bobbed up and down, and I tickled his balls while his cock swelled in my mouth, building to a release. I sucked harder, and the tip of his cock was now touching the back of my throat. He exploded, coming with such force that I nearly gagged. I drank his load down as he held my head, my throat muscles working to swallow it all. I sucked him till he was dry, then sat up and licked my lips.
Not long afterward, my cousin and her guy returned, so we went home. I told my cousin the next day about what happened. She loved it. She then told me she got fucked that night and wished I could experience that feeling.
It wasn’t until nearly six months later that I gave away my anal cherry to a guy who was a perfect stranger.
I was dressed in female attire, wearing a pair of heels, a skirt, blouse, some makeup, etc. I was walking to my cousin’s place three or four blocks away. A man of about 45 pulled up in a car and asked if I needed a ride. It had started to rain, so I accepted. Since he knew I wasn’t going far, he acted fast. He quickly put a hand on my leg, caressing it, and asked if I was looking for some fun. I got a thrill out of that and said yes, then asked what he had in mind. He drove us to a popular parking spot, then he took out his cock. He told me to suck him, so I bent down and gave him a blowjob. Before he could come, he stopped me and told me to get in back, so I did. As I climbed over the seats to get in back, he grabbed my hips and began rubbing my thighs and ass. I loved the feeling of his hands on me and didn’t want him to ever stop. He asked if I was a dirty girl, and I told him I was. Then he asked how dirty and if I liked it in the ass. As he said this, his hand was busy under my skirt, slipping into my panties to caress my ass. When he used a finger to gently probe my asshole, I told him I was a virgin.
He went nuts, and as I was hung up there, he climbed over my body and pushed my skirt up, then yanked my panties down and told me to relax. Soon I wouldn’t be a virgin anymore.
I was nervous when I felt him probing my tight hole with his cock, but I was also excited. I squirmed and he said to relax. He started to push in and my outer ring gave way, letting him slip inside. I begged him to go easy, and with a steady push, he slid completely inside my asshole. I was on fire. And it felt great!
He began thrusting into me with hard, forceful strokes. Then he picked up his pace. Gradually my ass stretched, and I got used to it just in time to feel him shooting in me. I felt the spurts, and the warmth made me tingle. I shot my own come all over his seats. He pulled back and yanked up his pants as I slid back to the front seat, come leaking out of my tender ass.
When he was ready, he took me to my cousin’s house and left. My ass was tender for a week.
After that night, I started picking up all sorts of guys, but mostly older guys who are married, since they never seem to care that I’m not really a girl. I now love having a cock deep in my ass, and it’s even better with one in my mouth at the same time. Gang bangs are incredible, too! I’m a total come slut and I love it. Name and address withheld

Something Very New

I’m a single 26 year old guy who’s been curious about cross dressing and transgenders for some time now. One Saturday night a local alternative club featured female impersonators so I decided to go check it out.

A woman was on stage in a skimpy outfit singing “Like a Virgin,” and she looked pretty good, actually. I watched for a while then sat down to have a beer. After the show I saw her sitting at the bar, her sexy legs crossed casually to expose her thigh.

At close range I still couldn’t tell her true gender since her whole outfit was flawless. I asked if I could buy her a drink and sat down next to her to chat. Her voice was soft and sweet and I knew that anywhere else she would easily pass as a true female.

She introduced herself as Missy and said she was glad I liked her dance. She casually laid a perfectly manicured hand on my crotch as she spoke. This had me hard in record time as she sat close to me and asked if I lived nearby. I nodded quickly and off we went.

Missy sat close to me in the car, her hand resting on my bulge the whole way. We kissed and groped each other at each traffic light. She smelled and tasted so good! By the time we got to my place we were more than ready to go. I couldn’t believe this was happening so fast!

We had barely gotten through my front door before Missy was down to her silky panties and bra. Due to a year of hormone therapy she’d developed small breasts and the rounded hips of a woman. She was a beautiful, sexy sight to behold.

We didn’t waste much time and ran to the bedroom. I climbed on top of her, dry humping her with all my clothes on as I devoured her pretty mouth. She moaned underneath my kisses and writhed beneath me.

I worked my way down her body, kissing every bit of her soft skin. When I got to her waist I slid her panties off and tossed them aside. She still had a cock, which was just fine by me. I’d always been curious about how transgenders had sex, and now I was about to find out.

I licked my finger and gently worked it into her ass. Then I spit on my hand and grabbed her cock, stroking it tentatively at first. It felt wonderful, soft, yet as strong as iron. I licked the tip, then slid the whole thing into my mouth. She gasped as my finger worked in her asshole and my lips caressed her shaft.

It must have been obvious to her that I’d never done this before. She held my head and guided me.

“That’s right, baby,” she whispered, “take it all in. Suck that big dick. You know you love it.”

I did love it, and I greedily licked and sucked as much as I could.

After a few minutes of this she pushed me back and rolled over onto her belly.

“You know just what to do,” she moaned.

I started on her smooth curved cheeks, kissing and squeezing them all over. My tongue went to her tight, puckered hole and probed it briefly before I replaced it with one of my fingers. She squirmed and moaned under my touch. I slipped my other hand down underneath her to stroke that hard cock a little more. My own cock was harder than granite.

Missy reached into her purse and pulled out some lubricant. She grabbed my cock and lubed it up before getting on her hands and knees. She wiggled her ass at me teasingly.

“Come and get it, big boy,” she giggled coyly.

I moved behind her and slowly penetrated her, inch by inch, giving her time to stretch and accommodate me. She squirmed and moaned a lot and finally I was all the way in. She moaned in pleasure as I began sawing in and out of her.

She begged me to go harder so I did. I reached around to jerk her off and in 30 seconds she shot come all over my sheets. I came too, exploding deep inside her ass.

I’ve seen her a few times since then but that first time with my Missy was the most memorable by far. For anyone who’s interested in transgenders, I say, go for it! C.J., Myrtle Beach, South Carolina

Totally Exposed

Well, last week it finally happened. At my wife’s insistence, I went to a doctor’s appointment wearing a pair of white panties with a pink butterfly on them, above the crotch. It was very nerve wracking for me, much to my wife’s pleasure, to know my doctor was going to see me this way.

But since I don’t own any men’s underwear, I really had no choice. She made the appointment and insisted I keep it. You won’t believe how relieved I was when I got there and was told that my doctor was out of town and his colleague would be doing my exam.

A nurse showed me to an exam room and pointed behind a curtain. She told me to strip to my underwear and put on one of those paper gowns with the opening in the back. Soon the doctor walked in and began asking me all the normal questions.

I was shocked at first to see that my doctor was a woman, but I kept my surprise to myself as she checked my eyes, ears, and throat and listened to my heart and lungs with the stethoscope. She then loosened the tie on my gown and let it fall to my waist, exposing my panties.

Acting very professionally, she asked me to lay back and relax. Then she checked my abdomen area, tracing her fingers down my chest and firmly pressing on my belly. Then she said the words that I’ll never forget as long as I live. “Sir, would you pull your panties down to your knees, please?” While I was pulling my panties down, she put on a rubber glove with a sharp snap.

She then started probing around my cock, checking for everything she could. Then came the part I love the most: She asked me to roll on my side as she greased up my ass with some lubricant. Then she inserted a finger in me and probed around until my penis was rock hard.

Finally she pulled out and wiped away the grease. She put her hand on my shoulder and moved me onto my back again. I’m sure she could see the effect she had on me, but she said nothing. She pulled my panties up to where I could reach them and I lifted my butt and pulled them up the rest of the way.

She said nothing to me and left the room. In a moment she returned and sat down and started writing in my file. She told me I could sit up, and I quickly did. My gown had fallen to the floor, so I was quite exposed.

She finished writing in my file and asked me if I had any questions. I told her no. Then she said that she was done and I could get dressed. But as she opened the door to leave, she looked back at me and said, “By the way, I love pink butterflies.”

When I got back to the waiting room my wife asked how my exam went and I told her all that happened. She told me that next time, I might get more than just a compliment on my panties. Name and address withheld

Delight in the Dark

I’m a 28 year old single male who’s into crossdressing. I like to go out to certain bars and adult theaters dressed up as a hot female. I love short skirts, dresses and lingerie, and I always wear stockings or hose. I have a small, kind of girlish frame to begin with, and I look totally female when I wear a wig and makeup.

A while ago I went to an adult theater dressed in drag, and as always, guys were all over me. Normally when I’m in a dark theater I give a bunch of handjobs, and maybe a few blowjobs. A lot of guys just like to feel me up, and some like to give me a handjob or blowjob too.

On this particular night I was wearing a long red wig, a black minidress, stockings, heels and full makeup, but no panties. I stood at the back of the theater when I first got there, allowing my eyes time to adjust to the darkness. Suddenly I felt a hand brush against my thigh, just below the hem of my dress. I looked over my shoulder and saw several guys standing behind me, though I couldn’t tell which of them it was. I soon felt it again, but this time the hand rubbed over my ass. I parted my legs a little, and the hand moved down to slide under my skirt and onto my bare smooth ass cheeks. Then I felt him push my skirt up over my butt, and I heard the unmistakable sound of a zipper being pulled down. A moment later I felt his cock pressing against my buttocks.

Before things got too far, I reached into my padded bra, pulled out a condom and handed it back over my shoulder. The guy quickly took it, and there was a moment’s pause before I felt his now sheathed hardness again rubbing my ass. Then it started to penetrate me, very slowly, and as I bent forward slightly he gripped my hips and pushed inside. I relaxed and pushed back at him, but that cock felt huge. Slowly it went into me, and finally he held me tight and let out a grunt as he buried the last inch of himself inside me.

He began fucking me then, and as he did I became aware of a guy standing to my left and another to my right, both with their cocks out. I reached out to take them in my hands. Another guy, who was sitting in front of me in the last row of seats, now turned around, knelt up on his seat and took my cock into his mouth, then started sucking me. This was all too much, and I soon shot my come down this guy’s throat, and he swallowed it all. The guy fucking me lurched into me and filled his condom, and as soon as he pulled out, one of the guys beside me took his place. I handed him my next to last condom, and he was soon fucking my stretched ass. The guy in front of me had his cock out now, slowly stroking it as he watched.

The guy now fucking me had a smaller cock then the first guy, and he didn’t last very long. After he pulled out the guy who’d been on my other side jumped in and took my last condom. His cock was a little bigger than the second guy, and his thrusts were a little more forceful, but he didn’t last long either.

When he pulled out the guy in front of me stood up and beckoned me to follow him. He led me to the very front row of the theater, over to one side where it was especially dark. He sat in a seat and pulled me down so I was kneeling between his legs. I took his cock in my hands and began to give him a blowjob.

More guys had followed us there. I soon felt hands on my ass again, and a finger slid into me. I spread my knees on the floor and arched my back for easier access. When I felt a cock at my ass I realized that I didn’t have any more condoms, but at that point I was too turned on to care. I felt a very big cock sliding into my ass, so big that I wasn’t sure I could take it, but I did. This guy fucked me hard, and I gasped with pleasure around the cock in my mouth, which soon twitched and poured its jism down my throat. I swallowed it all, and just then the guy in my ass stiffened and I felt his hot come shoot deep into my back passage.

As that cock slid out of me I felt it being replaced by another. I looked over my shoulder and saw that there were three or four more guys waiting for a turn at me. Then somebody pulled me away from the seats so he could stick his cock in my mouth, and soon there was a line in front of me too as I knelt doggie style on the floor. I was fucked in my ass and my mouth for at least an hour, and I would have gladly done more if the supply of guys hadn’t run out.

Finally I stood up, rather unsteadily, pulled my skirt back down and made my way out of the theater on wobbly legs. Come was leaking out of my asshole, and it felt stretched and tender, but I couldn’t have been happier.

As I went out to my car a guy walked up to me, offered me his number and said that if ever wanted to hook up with him, I could make a lot of money doing what I had just done. I said I’d think about it. A few days later I called him, and he’s been hooking me up ever since. I’ve made enough money for a boob job, and now sport brand new 36Cs. I’m now saving up for a total transgender operation to become a complete woman. G.B., Buffalo, New York


I cannot recall the first time that I was attracted to women’s legs, but I know that it has been as long as I can remember.

There is something that comes over me when I am confronted with a great pair of legs, especially if there is a nice ass at the end of them. Over the years I have been held spellbound by teachers, classmates, friends, strangers and lovers alike when they present their legs, especially when they are encased in black stockings and heels.

I am thirty eight years old, so my puberty years of the late sixties and early seventies were filled with women in miniskirts. I loved the female form of shapely legs and ass in heels and dark stockings so much that I tried to become that form.

When I was alone at home, I began to experiment with crossdressing. My parents were divorced and I had only one sibling, a sister who was a year and a half older than myself. I liked the way her clothes fit me.

I had then, and I still do have, a pretty, feminine body. My hips flare out from a small waist, and my ass looks so much like a girl’s that I have been teased about it quite often. And as I discovered the first time I gazed at myself in the mirror wearing pantyhose and heels, I happen to have a great pair of legs.

As I grew up, I “dressed” more and more often when the opportunity lent itself. I put on my sister’s pantyhose, high heels and minidress and basked in the glow of sexy femininity. I was a beautiful young “lady,” and I spent hours practicing my makeup skills and walking in high heels in front of a mirror.

As I got older, a persona developed to this image in front of a mirror. I knew that I was more than passable, and thinking about what I could do to the minds of men if they saw me really started to turn me on. I had always been attracted to women, but I grew to have more and more fantasies about men, though only when I was “dressed up.”

I had such conflicting feelings that it is still hard to deal with them. I knew that when I “dressed up,” I not only looked like a woman, I felt like a woman and I wanted a man.

I could almost come just by thinking about a handsome man taking me in his arms and passionately kissing me. To feel his hardness pressing against my “pussy,” to hungrily take his cock in my mouth and ultimately to be fucked. Not in the ass, but in my pussy, a pussy I didn’t have. I was afraid to take any steps toward this, though, because I knew that most people would think of me as a freak.

I blossomed into a full grown “woman” with all of my feminine attributes intact. Aside from light facial hair, it looked like God had made a mistake. Take my penis away and add breasts, and I was a woman, and a singularly attractive one at that.

Eventually I began to venture out in public, though at first it was only after dark for some innocent errands. The first time I got up the courage to walk the mall as a woman, I thought my heart would pound right through my chest. But I got plenty of lustful stares from men as I paraded from shop to shop in an attention drawing short dress.

My confidence grew, and so did my fantasies. I felt unfulfilled. I took to answering the door in drag during the day when solicitors called, and this further enhanced my confidence. Now, several days a week I would go all the way dress sexy, in full makeup, and go about my business the whole day as a woman.

One day there was a knock on the door, and I peeked out to see a handsome guy who appeared to be in his late twenties standing there with some literature under one arm and a clipboard in the other. I raced to the bedroom and looked in the mirror to make sure everything was in place and then hurried back to the door and greeted my visitor.

He started to talk about how he was out trying to get signatures to get an initiative on the ballot for an upcoming election. All the while he was looking me over in a most appreciative way. This guy was a real dream! He was about six two, with blondish hair, a deep tan and a very muscular chest and arms. He was dressed casually.

Finally, in my best feminine voice, I asked the man in. I was wearing black pantyhose, sheer to the waist, as I think this adds to a nice ass. My dress barely covered my butt, and the flare from the hips down hid my growing erection. This type of dress works for me because it is tight to the hips, then flares loosely like a skirt.

I always liked the way it draped over my ass and accentuated my feminine spine curvature and protruding round ass. Anyway, it felt better to allow any erection I might have to range freely inside my pantyhose instead of having it squeezed between my legs as I must do in other dresses.

Also, since my sister is several inches shorter than me, the old dresses of hers that I wore, which were already short on her, were really short on me! I also had on moderately high heels. By this time, I could walk in them with a feminine sway better than most women.

I had never been that excited in my life as I paraded around getting coffee while Dave he quickly told me his name made himself comfortable. He explained what he was doing with the initiative and why. All this while I could see that he had not taken his eyes off me.

Finally he said, “I’m sure you hear this all the time, but you sure are a beautiful young lady.”

I just smiled as I set our coffee down. Seeing as how I was apparently not offended, he went on to tell me he considered himself quite a leg man, and mine were as fine as any pair he had ever seen. I still had not sat down. I was going to make the most of this, and I strutted back for the cream and then the sugar.

During this time, I was admiring Dave as well, and one look at his crotch told me that he was both large and hard. He noticed me staring at his groin as I just stood there, and he seemed kind of shy and embarrassed. I finally got up the courage to speak.

“Did I do that to you?” I asked.

In a shaky voice he said, “Just looking at you takes me to heaven.”

“Well, if you behave, I’ll show you more,” I replied.

I put a sexy song on the stereo and proceeded to dance seductively for him, just as I had done in the mirror so many times before. I turned and raised my dress so he could get a full view of my ass and legs, and I swayed sensuously to the music.

When the song ended, I turned and told him I wanted to see “the damage.” He undid his pants and pulled his fully engorged dick out. I was mesmerized by it. I told him I was a virgin and wouldn’t fuck him, but then I smiled and said that I would like to please him. With that, I pulled his shirt off and knelt beside him.

I savored his muscular chest and arms and ran my hands all over them, then lightly fondled his cock. It was so hard, I couldn’t resist squeezing. My eyes glazed over as my head descended for my first taste of cock. I wrapped my lips around the head and started to take him in, as I had fantasized doing so many times.

I have seen many hard cocks in my life in pictures and movies, and I was pleased that my first was on the very large side. I could only take in about half of his shaft, so I did the best I could. It seemed so natural, and I was really getting into it when I felt him tense up, moan and start ejaculating his warm semen in my mouth and throat.

I swallowed and savored the taste, but I was not finished. I licked his nipples and belly for a while, then sucked and licked his balls till he was satisfiably hard again. He laid his head back and closed his eyes as I proceeded to once again orally massage his beautiful cock.

I was more aggressive this time as I wrapped my hand around the base and attended to the rest with my lips and tongue. I massaged his balls with my free hand as I passionately fucked his dick with my mouth. Soon he came again, with as much enthusiasm as the first time. When he left shortly after, I lay back and fantasized him lying on top of me, fucking my imaginary pussy, and I came like never before.

Since then I have had many sexual experiences both with beautiful women and as the beautiful woman, but there will never be anything like my first experience with cock.

E.W., Princeton, New Jersey