Transgender
2010-06-20

My roommate has been in the shemale world for several years. It started a year after I movedin with him. He used to dress in mens clothes, but about 6 months after me moving in, he told me he was gay. I thought no big deal, but I noticed he was ordering womens clothes, and shaving his body. I also noticed that he was getting tanner and tanner even though outside it's the heart of a vancouver winter. I asked him one day after work, "are you crossdressing?"

He told me to stay right there. He went into his room, and came out maybe two or three minutes later wearing an all white dress. The bottom have clung tight from his waist down about five inches (really low cut) while the tophung loosely, but still fit slim. His shoes were black pumps, straps this way and that. His legs were shaved smooth and, and when he gave a 360, I could see his black thong under the tight white skirt. "What do you think?" he said. I stood up, and even though his hair wasn't long like a girls, he still looked like a woman. "What are you?"

He smiled, and told me to sit. He sat next to me, and told me all about his wanting to be a shemale. He told me he has plans for breast implants the following summer. I wasn't stunned.

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   He was so incredibly gay, I kind of guessedthis would happen. His friend Ellen (also a shemale) came to the house and (after having sex) sat in the living room and discussed the shemale way of life.

After our discussion, he was free to wear womens clothes throughout the house. I would come home from work, and find him sitting in tight yoga pants, and tight top that ends just below his belly-vutton, leaving a few inches of tan skin exposed. His belly-button was pierced with a ring that hung down an inch or so. He was growing his hair out, which made him look even more like a girl, he wore some make-up but not a lot. Attractive at time, sometimes extremely like when he would dress to go out with his friends.

One night, I brought a girl home from a party I attended, things were going well until I must've said something wrong and she hurried to leave. Once she left I sat out in the living room with my roommate. He was wearing a pair of tight white pants, and a grey hoody. We talked, and I ended up telling him that my sex life hasn't been the same since I broke up with my girlfriend a few years back. He asked me how I am in bed, and I couldn't answer him honestly.

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"Show me," he said. I looked at him and said, "what?" He looked at me smiling, his teeth so white, and said, "come over here, and show me your moves," and he stood up, "like dry-hump kind of. "

I said, "OHHH.

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   Ohh, okay," and got up. He turned around, and said, "take me from behind," in his sexy girl voice and laughed. I said, "that's porn shit, I usually end up doing the boring sex. " He looked at me, laid down on the ground and spread his legs, and said, "show me, then. " I got on the ground, positioned myself over him, and began to dry-hump. "So this it it?" he asked. I grabbed him by the waist, and rolled over, no he was on top, he began to rub his waist up and down on me, and said, "That wasn't bad," and turned himself around into the reverse cowgirl position. He bounced on me, and I found myself getting surprisingly hard. "You should try it like this," he said. I grabbed the back of his pants, and peeled the top down revealing his grey thong. I kept peeling for some reason until I reached the rack of his ass, the string of the thong buried deep between his cheeks.

I snapped his pants back inplace, and pulled the both of us up. He turned, and laughed and said, "well?" I could see he was wearing his make-up, his eyes looked like a womans, and I moved down to his chest. Although he was still boobless, he still had small buds (dont ask me how). I picked him up by his waist and carried him into my bedroom, the whole way he was laughing, and I set him down on my bed.

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   "Show me first hand," he said and pulled his hoody off. He was topless, little buds of breasts there, and I was naked in almost 5 seconds. I pulled his pants off, and turned him over. I pulled his thong down, and he turned over. His penis was small, slightly erect, and shaved except for a small pants above the base of the penis. I slipped a condom on, and he applied lube to his hand and work it in on himself.

I watched him spread his legs, and I positioned myself over him. I put myself in, I slid in with ease, and he put my hands on his chest. I squeezed, and I rolled us over. He began to move himself up and down on my erection, and said, " you're doing fine so far," and we had sex in silence for a few minutes.

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I sat up, and stood, still inside of him, and put him down. He pulled me out, giggled, and turned around. I put myself back in him as he leaned over my dresser. I finally made him moan his girlish moans for five minutes. If it was one thing I was good at, it's stamina in bed.

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   I could last for a long time. Even he was impressed when he pulled me out again, sat on the edge of the dresser, and let me out myself in him again. I was staring at his cock, now almost soft, and we had sex in that position fir another 4 or 5 minutes.

We walked to the living room, and he sat me on the couch, and he turned, and sat on my lap. Bouncing on me, he jerked himself hard, and a few more minutes later he was squealing as he came. He let me keep going for another 3 or 4 minutes in this position, and then we changed again into lying face down on the carpet with me behind him, and that went on for another 2 minutes until I went faster, and had to come. I whispered this in his ear, "I have to come," and he rolled me off of him, and tore the condom away. He didn't give a blowjob like I had ever gotten before. He let the tip of me slid in his mouth, and jerked me. I came a few seconds later, and he didn't spill a drop as he let me come out. He stood up, and said, "How was that?" and gave me a hug. I looked at him, and we stood there naked, hugging. I sat down, still hugging him, and we talked.

We had sex once more that night, this time lasted longer, and meant more. In the morning we showered together, and afterward we madeout in the living room for several hours before having sex again.

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   I asked him if he would be my girlfriend, and he said we should wait until after he gets his brest implants. I told him that no one would are if we didn't wait, and he finally agreed. We live together, and we're dating, and it's been a few months, but things have been great. He's getting his breasts in a few weeks, and I camt wait to see how they turn out. .