tagTranssexuals & CrossdressersMy Cross-Dressing Life

My Cross-Dressing Life


The first time I learned I might be different is when a friend of mine—we were both drying off after swimming in the college pool—told me my body looked like a girl's. I'd received some looks before, but that was the first time someone came right out and told me my physique was leaning a little toward "feminine." A few weeks later, while loitering in the college library's human sexuality bookshelves, I looked through an old copy of "Everything You Wanted to Know About Sex but Were Afraid to Ask." I read through the section of the book that addressed transvestism. It intrigued me. I was young and curious. I'd recently been told my body was suspect. So I thought I'd give it a try.

The following weekend, I visited my parents house to take care of their dog Bob while they were away in Florida, and while there I took the opportunity to pull on some of my older sister's undergarments—she was attending college on the west coast. Then I looked at myself in the full-length mirror in my parents' bedroom.

I remember actually trembling from the experience. My sister was a little fat, and I was pretty thin, so everything fit perfectly. It wasn't long before I couldn't wait for my parents to visit Florida some more so that I could try on other items from my sister's wardrobe. I put on her bathing suit and high heels. I learned how to apply makeup. I wore her dresses. I squeezed into her panty hose. I even put on the flimsy nighty she must have worn for her boyfriend on certain nights.

Seeing myself like that gave me an appreciation of what most other guys didn't have—gentler curves and the kind of proportions that made me suspect in the locker room. But, I actually loved looking like a woman. It was my secret, and I didn't share it with anyone. Just the opposite. When not cross-dressing, I tended to exaggerate my masculinity, as if to hide or disclaim my hidden self.

Of course, cross-dressing was more than a strange and wondrous exercise by which to charm myself. It became a way toward sexual gratification. My sexuality became inseparable from wearing women's clothes. Certainly, I was not attracted to other men. Only women caught my eye. Which is to say, if I saw a beautiful, sexy woman wearing something beautiful and sexy, it would excite me. In truth, I was imagining how that miniskirt or lingerie would look and feel on me!

It was the same with pornography. I loved seeing photographs and videos of women sucking men's cocks, and I wasn't the slightest bit interested in watching men suck men's cocks. But it was still the cock that was central. Today I'm pretty sure that I needed a woman to stand in for me, because what I really wanted was to suck cock. But I had no way of knowing that at the time, no way of knowing that by dressing up I was able to deny my homosexuality. In fact, I wouldn't know that until the first time I found myself with a man in a sexual situation. Then I found out very quickly. But I'll get to that later.

It does bring up the question though. Are most cross-dressers really straight? Perhaps not. Perhaps cross dressers internalize straight society's distaste for homosexuality and need to turn themselves into fictional women before they can express their true desires. Although that could be true only of myself, needless to say.

Sadly, I was a college student just before the internet became a big part of life. The only information about transvestism I could find were a few books in the library, but they weren't very encouraging. And I didn't know any other transvestites, obviously. As a cross-dresser I was pretty much alone in the world. My sense of isolation became even more pronounced after I bought my first car. That was in the summer before my junior year. I had one of my sister's sundresses tucked under the driver's seat. It was flowery and short and had a string that tied together behind my neck. Easy to get into and out of. I'd also "borrowed" a pair of her sandals, the ones with a medium heel. In the evening, I'd drive somewhere secluded—empty parking lots behind closed stores, the fields on the edge of town—and put those things on. Then I'd walk around a little in the moonlight, feeling impossibly delicate and vulnerable, swinging my hips as a cool evening breeze flowed up my dress and caressed the backs of my legs.

One day I made an illegal U-turn at the wrong time. The cops pulled me over, and when they saw I had a dress on they took me in. After leaving me in a holding cell for a couple of hours, they let me go. I guess they couldn't figure out what to charge me with.

But the episode traumatized me. From then on, I began to cross-dress in clothes that were transgressively feminine but were not technically women's clothes. For instance, I would put on a pair of cutoffs that were cut very, very short. I rolled them up even shorter so that they were halfway up by ass, knowing that if I were pulled over I could quickly roll them down. The shorts would raise eyebrows, but probably that would be all. I also wore a tee-shirt that was a couple of sizes too small, and, again, though it bared my stomach and waist, I couldn't be taken in for wearing it. And instead of women's sandals, I wore flip flops.

Eventually, I graduated from college, but that didn't stop me from cross-dressing. I moved to a bigger city and into an apartment of my own. It wasn't long before I learned how to relax when looking through the women's section at thrift shops and second hand stores. Some of the people working there were actually quite nice. One woman asked if the shoes I was holding, a pair of stiletto heels, were for me. When I admitted they were, she helped me pick out an entire outfit. But I was still very much alone. At night, I moved through my apartment wearing corsets and high heels. My hair was long enough to put up into a bun. I shaved my legs. I wore lipstick, eye shadow, and false eyelashes. I knew I was passable. But I never dared go out in public dressed up. Everything was done behind closed doors.

In addition to dressing up, I started using sex toys. I bought a large, flexible dildo, shaped like a penis. I had a good deal of fun with that thing. I would squat in front of the mirror in my apartment wearing a corset or a garter belt with stockings and high heels, and slide the dildo into my ass, moving up and down on it and masturbating until I came.

Of course, this all took a lot of preparation and time. It also made me feel guilty after a while, not about what I was doing so much as about how it was keeping my apart from the rest of humanity. I was existing as a ghost. Meanwhile, the denial of my homosexuality began to crumble. I wanted to replace that mirror. I wanted to replace it with the actual eyes of someone watching me. I wanted to perform what I was doing in front of the mirror for someone who would be turned on. I wanted that mirror to be another man.

In the end, it unfolded like this: I put an ad in the Yahoo adult personals. By this time, the internet had really taken off and was still supremely anonymous. I think the ad went something like this: "Young, good looking exhibitionist would like to strip naked and masturbate while being watched by another man." I also requested an age range, making sure the guy would be older than me, and I gave my "stats."

I got three replies, and I chose the second based on its tone and the fact that the guy had a condo for us to play in. The next day I was at his door. I just put one foot in front of the other. He was a little older than I'd thought he'd be, he was in his late 50s, but otherwise I was not displeased. After all, I had no intention of touching him or being touched by him. I just wanted him to watch me.

For a while we sat in his living room, chatting. He seemed like a nice enough guy. He was recently divorced. There were pictures of his college age sons on the cabinet behind him. He explained that he saw a couple of guys routinely, and he mentioned that one of them just loved to get fucked. It was all a little bizarre. I'd never had a conversation like this before. But when he asked if I was ready to get started and whether I'd like to perform here in the living room or move upstairs into the bedroom, I was more than ready.

Upstairs seemed like a good idea. We walked up a flight of stairs into quite a big bedroom—the sheets neatly turned back, beige carpet on the floor, blinds closed. I took off my clothes, and right away he took his off as well. That surprised me, because I thought he was just going to watch. He began to jerk himself off. I got hard and started jacking off as well. I sat on the edge of his bed, and then I did something which turned everything around. I have no idea where it came from, it was completely unplanned, but suddenly I wanted to make out with this guy. He understood somehow. He leaned down and French kissed me. Then he rubbed his cock over my nipples. It came as a big surprise, but I desired this man, desired his cock, desired his touch. It was a far more intense desire than just the desire to be watched.

As if it was the most natural thing in the world to do, I took his cock in my mouth. He moaned. I licked his balls. I moved my tongue up the shaft of his cock, I circled his glans, then I sucked him fast and furious. Not wanting him to come yet, I pulled back and slid my hand up and down his cock, wet with saliva. He was a hairy guy, with a pot belly and breasts that sagged a little. Bearish. But I liked that. I stood up and moved myself against him. He put his hands on my waist. We kissed again. Of course, I knew what was going to happen next. It was inevitable. He pushed me back on the bed and spread my legs. I don't know where he got the condom and lube from, but he had the condom on in a second, then he was putting his finger into me, then two fingers.

The rest was like magic. My anus relaxed, and I heard myself pleading with him to fuck me. So this was what easy, uninhibited, sex was like! With my hard cock jumping against my belly, I put my hands behind my head. He positioned his cock over my hole and slowly pushed forward. I'd put things in my ass before, but this was nothing like that. His cock was both hard and soft, and, most important, it was alive. It felt hot. He leaned forward. With his cock sunk deep into me, he put his tongue in my mouth. I sucked on it greedily. He moved himself in and out, forcefully yet gently. Soon, I was making sounds I never knew I could make. A clear liquid spilled out of my cock, even though I hadn't come yet. He began to thrust faster. Everything felt sticky and wet. Then he pulled out of me and tore off the condom. A great geyser of cum slapped onto my stomach, hot as lava. I came as well. Our cum mixed together until great gobs of it slid over my bare skin and onto the bed sheets. We were breathing heavily.

"Well, that was a pleasant surprise," he said at a last.

It was a pleasant surprise for me as well. I managed to tell him it was the first time I'd ever kissed a guy, sucked a cock, been fucked. He raised an eyebrow.


I swore it was. We hugged, the wet cum squishing between us. Then we took a shower together. Once we were dried off, we had sex again and took another shower. After that, I took off. He gave me a kiss on the cheek, which I thought was cute.

Outside, a crew of city workers were clearing a drain. As I walked past, they looked up. I felt terribly self-conscious. They smirked, as if they knew my ass had just been filled by a delicious, hot cock. Something in the way I was walking or holding myself maybe. But I didn't care. No need to shore up a fake masculinity anymore. I got in my car and gave them a big smile. Then I drove away, knowing I'd soon be back.

And that's where things are now. Roy (yes, he has a name) is my lover and mentor. Cross-dressing is no longer as important, but it's still a part of me. I especially like to wear heels, and nothing else. Roy has introduced me to some other men. I 'm expanding my vocabulary. We're going out. We have dinner together. I'm living in a heightened state of eroticism. I'm having a lot of fun. And, most important, I no longer feel like a ghost.

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byroberty© 9 comments/ 15028 views/ 12 favorites
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by Anonymous

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by Anonymous04/22/18

Cross 👗

I'm bi and love to wear women's clothing. It just feels right

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by hobbnobb7710/16/17

nice story

i enjoyed reading this story, easy to follow and looking for next chapter

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by TVlvr198410/12/17



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by MarieJoanne10/06/17


Loved it. And for what it's worth, I have similiar desires as soon as I dress as Marie. Xxxxx

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by IcelandSpar10/06/17

Thanks for writing

A very refreshing read, short and sweet, please write more!

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