OK, kids, here's my first Trannie story. Hope you like it! ==============================================================
It was my first night in Washington, D.C. I was on my way to an Army base in Maryland and hand flown in to D.C. to see what the city was like. I'd taken a shuttle bus from the airport to downtown where my hotel was. I had about $500 in my wallet so my first priority was to get to my hotel room and stash most of the cash. I had a hollow bible that I hid my cash in when I traveled. I would place it in a nightstand drawer and it never got touched, no matter who spent the night with me. I was seriously horny. I'd visited my girlfriend, actually my ex-girlfriend while I was on leave. She broke up with me the first day home so we had not spent any "quality time" together. I had decided to hit the streets and find me a willing hooker to spend the night with. It was after 9:00 on a Saturday night when I checked into my hotel room. I got my room key, unpacked my bags and freshened up. I checked the phone book to find out where the majority of X-rated movie arcades were. Having found the area, I looked it up on the map and found it to be only 3 or 4 blocks from here. I set out in the cold, January air. When I turned the corner, the first thing I noticed was two black men kissing each other. There wasn't any mistaking it, either. This was not some "Nice to see you, pal" kiss. Their lips were locked and there was some heavy tongue action going on. I figured "To each their own" and that I must be at least close. I saw the neon signs for the arcades and then the women walking the street. I wet my lips and joined the crowd. I wanted a woman who would come back to my room, preferably someone who was willing to spend the night. I didn't want to go to someplace that she picked. I'm kind of a neat freak and I figured I had less of a chance to get mugged by a pimp or something if she didn't choose the place. I talked to a few girls. There weren't many out, it was pretty cold. Of the ones I met, most wanted to go to their places for an hour or so. A couple agreed to come back with me but only if we stopped at their "managers" place first. That didn't sound too safe so I kept looking. I was just about to call it a night and head back to my hotel when I saw her. She was tall, very dark skinned and beautiful. From what I could see under her heavy coat, she was small-breasted, but her legs were to die for! She walked up to me as I was looking at her and said, "Like what you see, honey?" I, of course, told her I did and that I'd love to see more. She quoted me a price that was fair. I asked her how much for the rest of the night at my hotel room. She blinked a couple of times, looked at me for a minute and then told me $150. I promised her more than that if we had a good time. Or bargain sealed, we started to walk back to my hotel. She didn't get a block in her heels so I hailed a cab to take us the rest of the way there. In the back of the cab, I rested my hand on her knee. She smiled, kissed my cheek and told me the attention was sweet, but she wasn't the kind of girl who made out in taxicabs. When we got to my hotel, we took the elevator up to my floor. She held my hand and kissed me lightly on the cheeks and lips during the ride. The elevator wasn't the only thing going up at that point! Inside my room, I poured us each a glass of wine as she took off her coat. She had on a blouse and skirt that showed off her lovely legs to good effect. After we each took a drink of wine, I asked her if she wanted to take care of financial arrangements now or in the morning. She replied that she trusted me and wanted to postpone that until later. Delighted, I took her into my arms and kissed her passionately "Not too many men are willing to kiss a whore." She said. "You're a beautiful woman. How you make your money is nobody's business but your own." I told her. With that, she kissed me back with even greater passion, her tongue finding mine. We fell to the bed in a tangle of lips and hands. Soon, her blouse was off and I could tell that her breasts were quite small. It didn't matter to me. I was naked at that point with my painfully erect cock waving in the air. I reached for her skirt but she instead moved out of the way and took my cock in her warm, wet mouth. I'm not all that long, only about 7 inches, but I'm fairly thick. She quickly had me down to the base and my cock-head was in her throat. She proceeded to give me the best blowjob I'd ever had. She held the base of my cock with one hand while she licked at the head. Then she slowly engulfed the entire cock and moved the head in and out of her throat. She massaged my balls and let one long finger slip between my cheeks to play with my asshole. Before I could warn her, I was spurting into her mouth. She took it all and seemed to enjoy the taste. Before lieing down next to me to cuddle and kiss, she got us both another glass of wine which we sipped in a wonderful afterglow. I thanked her for such a fantastic blowjob and told her that now that the tension was relieved, I'd last quite a long time as we made love. She smiled and told me how much she wanted to do that but suggested we try something else since it was her time of the month. At that point, I noticed that there was something wrong with her hair. I'd grabbed it while she was giving me head and it looked^Å She was wearing a wig. I reached out and gently removed her wig. I don't know what I expected at that point, a bald head? I was still thinking that I was with a woman at that point. What I found was a short, mans hairstyle. I was with a man. A very pretty man but a man. I'd never had sex with a man before. It wasn't that I was a homophobe, I'd never been approached. And I was in the military and you could get kicked out back then for such a thing. "You must hate me now." She^Åno he said. "I don't hate you. I don't understand everything that's going on, but I don't hate you. Want to tell me about it?" He told me how he had always felt more like a girl than a boy when growing up. How he had never fit in, never been interested in girls. He had been undergoing treatments for an eventual sex-change operation until the money ran out. At that point, he had turned to street walking. I had been his first customer. "I'd been with men before, just never for money. I don't think I'm cut out for this job." He said. I then noticed that I was still holding him next to me as we spoke. I blurted out the next question I had, "Do you still get hard?" Without saying anything, he undid his bra, letting his small breasts free. Yes, the nipples were hard. Without thinking, I reached out to play with one as he slipped his skirt off. Underneath his skirt was a very tight jock-strap type affair. "This keeps my cock from spoiling the illusion." He said as he slipped it down. With that, a small but hard cock sprang out. It looked to be around 4 inches but very hard. I was massaging his breasts and gently tweaking his nipples at that point. I pulled him down onto the bed next to me and started to suck on his hard nipple. As I sucked his nipple, I reached out and took hold of his cock. It was the first cock I'd felt other than my own. It felt good in my hand. He moaned and pulled my face up to his and we began to kiss again. He broke the kiss long enough to ask me if I wanted the wig back on. I told him he was beautiful with or without the wig. After kissing him and stroking him, I wanted to taste his cock. I needed to do it. I took him in my mouth and ran my tongue up and down his shaft, trying to do for him what he had done for me. After a few minutes of this he begged me to fuck him instead. He reached into his purse and lubed us both up.He then grabbed his knees and spread himself for me so that I could mount him from the front. It was awkward at first but soon we were kissing deeply and I was buried to the hilt in his ass. I plunged hard and fast into him and he loved every second. After a while I came hard and felt him shoot as well. We slept together that night. In the morning he was gone. So was $200 out of my "hidden" stash! I didn't begrudge him though. It was more than worth it.