Chapter 1

Transsexuals have always been a passion of mine, ever since I first became of aware of their existence when I was 14 or so. Men never attracted me, and women are alright, but give me a transsexual and I'm in heaven.

I suppose I should back up. My name is Dave and I'm retired now from the Air Force, having done my 30 years and I live abroad, traveling as I desire. I have a good income and right now I'm sitting in Thailand, in a house I've rented, just relaxing with Erika, my new wife. I've never tried writing anything, but I've enjoyed some of the stories I've read on different sites, like A.S.S.M. and Kristen's Archive, Nifty, etc. But largely only the ones that are true, or at least sound believable. What I put here may perhaps get boring, no promises about my skills as an author, but it will be the truth also.

My father had a small collection of pornography; this was in the 60's mind you, when magazines were about the only thing available. His only hardcore magazine was something from Holland which was supposed to be 'educational' and it covered everything with very graphic pictures and scientific text. But it was porn, just masquerading as literature. One section dealt with transsexuals and the first picture was of an attractive woman with a large, but flaccid uncircumcised cock. Just sitting there naked. The captions said something like "Is this a man? Or a woman with an over-developed clitoris?" I was fascinated by her and there were perhaps a dozen pictures of this transsexual, both alone and giving oral sex to a man. There was one picture, the last, in which she was getting anal. I jerked off to that magazine every day for years, until I guess my dad, or perhaps my mom, threw it away. But it had me started and I never looked back.

My first experience with a transsexual was predictably not with a TS, but with a passable transvestite. I was 18 then, just getting ready to go to college for the air force when I was at a party. This was 1971 and everything was kind of weird anyway, even in the Midwest where I was growing up. I didn't know a whole lot of people at the party, I'd come with a couple buddies and they'd hit on some girls and done pretty good. I'd talked to a few, but when I saw these two girls sitting close together and relatively alone, I did a bit of a double take.

One of them was obviously a guy in drag, there was little doubt. He must have still been learning and didn't appear very feminine at all, but it was interesting to me. Everyone at the party was getting high and on this love everybody kick, so nobody messed with him. Not like a few years later when you'd never see anyone doing that, being so brave as to at least try and be themselves. That was one thing that little period in history had going for it, I will admit.

The guy in drag was sitting with a girl, at least she looked like a girl, and not all that bad either, at least from across the room. I figured I'd go over and talk to the girl, just to get a closer look at the TV, because like I say, it was interesting. As I got closer I realized that the girl was a guy in drag as well, he'd just done a better job of passing herself off. This didn't put me off at all, although I did feel a small bit of concern over my buddies seeing me talking to a couple of transvestites. But it was just going to be talk, and besides, my friends had disappeared with their girls anyway.

The attractive one was wearing a blouse and long skirt to cover her legs. She had a blonde wig and a lot of make-up, although not as much as her friend and it was much better applied. She looked feminine enough and wore a maiden form bra, I imagined, under blouse to give her some shape.

I walked up and said hello, introducing myself to them. I was 18, like I said, and a bit of a jock in high school. I had short hair and a strong body, defined if not truly muscular. Most of the people there were hippies, with long hair and skinny bodies. Some of them looked at me even more strangely than they looked at the two transvestites.

A lot of transvestites are just into the clothes. That's something a lot of people don't realize or respect, and truthfully, I didn't know anything about it at the time. A lot of stories I read are total BS because they assume every TV is gay and they're not, but I have found that even the straight ones enjoy attention from other men. Even if they have no desire to have any sort of physical contact, just being treated as a female is very enjoyable ... or humiliating, in the case of those who are into forced feminization. But that again is just another form of pleasure.

The two girls, I'll refer to them that way just to make it easier, were calling themselves Denise and Kathy. Denise was the more attractive one and I admit I focused most of my attention on her, but of course the way to a girl's heart is often made easier through her friends, so I was equally nice to Kathy. I found them some drinks and sat down with them, sitting next to Denise, so that she was in the middle, and we talked for awhile. They had adopted soft whispery voices and their gestures and postures were meant to imitate women. It was cute, I thought, but not entirely persuasive.

They were both 20 years old and best friends, attending the local junior college. I told them I was leaving for college soon and planned on joining the air force. They seemed mildly impressed by that, which was a little surprising because the military wasn't very highly regarded in those days of Vietnam at all. I asked Denise if she'd like to dance, but it was probably a good thing she declined, dancing to The Doors is all but impossible unless you're on acid or something. She countered by asking me if I wanted to go out to their car and smoke a joint. I didn't do drugs at all, never wanted to, so I declined, but I did say I'd go with them just to keep them company if they wanted.

I think Kathy was getting bored by that point though and was pressing her friend just to go home. I think Denise wanted to stay, at least she seemed to be looking at me like she was interested, but she told me it was Kathy's car, so she kind of needed to go. I had ridden with my friends and I decided to be a little bold, I asked them if I could get a ride. They agreed and we left the party together. I told them as we were leaving that I hadn't enjoyed the party very much, but meeting them had made it all right. I meant it too, I really had nothing in common with those people once my friends had disappeared, and the girls told me the same thing, that it was hard going out as they were and had only done it because they were really trying to 'find themselves' and they were both glad they'd met at least one person who'd accepted them.

As we walked the half block or so to their car I slipped my hand around Denise and she didn't protest, but she didn't seem to move closer either, the way a girl will sometimes. It was kind of a neutral reaction and I was wondering if I was screwing it up. Well, I was wondering about a lot of stuff really. I wasn't entirely sure what I was doing, or even why, but my heart was going a mile a minute. The car was a big old Chevy with a bench type front seat and Kathy drove with Denise in the middle. I kept my arm around her and I was pretty sure she wasn't going to let me do much more than that, especially with her friend there, but I was pretty excited just being close to a transvestite for the first time, so I couldn't help myself really.

I brought my other hand to rub her thigh through the skirt she wore and Kathy didn't seem to notice but Denise obviously did and she put a hand on top of mine and leaned close to me.

"David, I'm not sure I want to do anything, you know?" She spoke softly and I could smell the perfume she wore. She looked much better in the dim light of the car anyway, more like a real girl than she had at the party and I just nodded.

"Okay, sure." I tried to put a happy face on it. "I'm sorry; it's just that I think you look very nice."

"Thanks." She smiled and squeezed my hand.

The drive was kind of long, about 30 minutes back to town. I was still living with my parents and my house was a few miles out of the way, but not bad. It gave me enough time to try again. I moved my face closer to Denise, until I was almost kissing her ear and I breathed softly, feeling her go a little stiff next to me and she turned her head. I kissed her then, impulsively, without thinking, just a little one on her lips and I think if it hadn't been dark I'd have seen her blushing sweetly.

"David!" she whispered, and Kathy looked over at me, a little disproving I think.

"What?" I smiled and decided I'd just do it. It would be a long walk if I got kicked out, but I was just too excited to stop. I kissed her again; trying to French her and my tongue licked her closed lips as I pulled her a little closer.

For a moment I really thought she wasn't going to kiss me back. I figured that was it, I'd gone too far already, and it was over. But gradually her mouth opened and I started tickling her tongue with mine. After that we made out the rest of the way back, a good 15 minutes or so and I totally forgot about Kathy. We were Frenching and getting very warm and my hand was sliding up and down Denise's leg slowly.

The car stopped suddenly and we broke our kiss, Denise pulling away from me with a little jerk and I looked around, seeing my house across the street. I didn't want to get out of that car for anything, but it didn't seem like I had much of a choice. Denise wasn't looking at me and Kathy just kind of stared at me. It felt really weird and asked Denise if I could have her phone number. She glanced at her friend and then looked at me.

"Do you have to go in?" she said, real softly, and I felt my heart speeding up even more, if that was possible.

"No, I can do whatever I want," I answered, maybe smiling prematurely, but I couldn't help it. "What about you?"

"Do you want to come to my house?" she asked.

I nodded over Kathy's objections: "Denise, we should just go, it's late, huh?"

"We can go to my room," I suggested. "We have a room over the garage, kind of a spare bedroom." I looked at her hopefully. "I mean both of you, if you want, just to talk or something." I hadn't meant to include Kathy, but I really wanted Denise to say yes.

"Okay." Denise was agreeing and she told her friend she'd be okay. Kathy didn't want to leave her, but I think she was a little miffed by then and just waited until we got out of the car and then drove off. I suspected that maybe they were lovers or something, it seemed like a reasonable expectation, and I felt a little bad maybe that I might be taking someone else's girl, but I wasn't forcing her, and I didn't worry about it a whole lot.

We went up to the room above the garage that was basically just a bedroom with a very small toilet and shower adjoining it. There was a daybed in there, a dresser, a small radio and some books and games, not much else. We sat down on the bed and it was a little awkward at first. I wanted to jump right back to where we'd been in the car, and I think Denise did too, but she was very nervous about it and I could see she was having second thoughts.

I put my arm around her again and started kissing her neck and ear, rubbing her leg again, when she turned her head and we started kissing. We just did that for a long while, kissing and getting warmed up. I rubbed her body a little and she wrapped her arms around me, but I was a little slow to do much more.

When I did finally slide my hand under her blouse, feeling her warm skin and the firm, but empty shells of her bra, she stopped our kiss and looked at me.

"David, I'm not gay," she said. "I mean, I've never done it. I didn't even know I wanted to."

"Me neither," I told her. "But I think you're a girl, right? So it's okay?" I really was thinking of her as a female, I wasn't just saying that, and she wanted to believe me.

"Are you sure, because I'm scared, you know?" She giggled nervously at herself and I just nodded.

"It's okay Denise." I gently kissed her. "I'm not going to hurt you, okay?"

She nodded and we kissed some more and I was slowly getting her undressed, removing her blouse but leaving her bra on, because it looked sexy in the soft light. I managed to get my hand up her skirt finally, and we were basically lying on the bed by then. I felt her hand rubbing my bulging cock through my jeans and I was dying to feel hers. But every time I came near Denise would close her legs and push my hand away.

"It's okay," I breathed at one point and basically forced my hand past her resistance until I could feel her penis beneath her panties. She was as hard as I was and there was a wet spot on the soft cotton from her precum. I slipped my fingers inside to feel the hot slightly damp flesh and she moaned and fumbled at my pants, getting them open enough so she could get her hand inside. We kissed for a long time, just rubbing each other and it was the first time either of us had touched another man's cock, I think. If she'd been a regular guy I would have been repulsed by it, not turned on at all, but dressed as she was, made up like a girl and acting so effeminate, I loved it.

I was soon naked after that and Denise played with my free cock for awhile while I fondled her and finally she got up enough nerve and desire to move her mouth to my penis. I'm not overly large, a little bigger than average I suppose, but I must have looked huge to Denise. Her penis was smaller than mine, but it felt nice, and I rubbed it while she took her first tentative licks. This was the first blowjob of my life, although I wasn't a virgin by any means. And so maybe it wasn't the best blowjob I would ever get, but in my mind it is. I had nothing to compare it to, and time has a way of exaggerating things.

Denise started sucking me, wrapping her lips around my cock and bobbing up and down, gagging and coughing once in awhile, but getting better as she went along. She'd turned her body so that I could feel her ass, and it was nice. I had a hard time even thinking that butt belonged to a guy, it was so nice and round, and smooth. I pulled her panties down far enough so I could massage her ass, squeezing and pushing a finger into the crack, feeling her tight little hole. Denise really seemed to like that and she sucked a little harder, starting to get into it I think.

It certainly wasn't going to take me very long to cum and I told her that I was close. She either didn't hear me or didn't care and I was fingering her ass gently when I told her again, hunching my hips a little because I was so close I couldn't help it. She did pull off of me then, just pumping me with her hand, her face inches away as my cock swelled even more and then erupted, spraying cum in little hot creamy jets across her pumping hand and onto my stomach.

I was breathing hard and so was Denise, staring at my cock as she worked her fingers slowly up and down the shaft. I'd shot out quite a bit and I just sank back, gasping. She kept playing with my penis and I grabbed my t-shirt to wipe up the mess and I wasn't surprised that I hadn't gone soft at all. In those days my cock was perpetually hard, and I used to jack off like 3 times in a row, without ever losing my erection. Ah, glorious youth, as they say.

We started kissing again and this time I got Denise's panties off, leaving her in her skirt and bra. I played with her cock, moving around so she was on her back and her skirt bunched around her waist. I stroked her penis until it was very hard, but I didn't go down on her. I was too eager to make love to her. I brought my body up, laying on top of her and pressing my own hard cock against hers, humping her while we kissed. It felt really good and we were both very hot when I asked her if we could go all the way. She was frightened I think, probably by the size more than anything, but she nodded and we kissed again until I lifted myself off.

I knelt between Denise's spread legs and for a moment or two I watched as she used both hands to squeeze our cocks together, sliding her hands up and down them both at the same time. I was ready to get inside her, but Denise surprised me by cumming suddenly like that, her own semen pulsing out the tip of her cock and down over the both of us. She massaged her sperm onto my straining penis for a few minutes and I was almost afraid I was going to cum again, but she wasn't doing it hard enough to really bring me off, thank goodness.

It did have the effect of giving us some lubrication though, which was a good thing. I had her put her legs over my shoulders and I rubbed my leaking penis around her anus until it felt about right and then I started pushing until I could feel her body giving way. Denise was holding her breath and I felt her tense up and every now and then she'd give my back little slaps, breathing for me to stop, and I would. It was a long slow process getting my cock inside her ass, because I didn't want to hurt her at all. But even so, it was obvious that there was lot of discomfort. She was extremely tight inside and being dry didn't help at all, my cock was dripping precum like crazy and that helped a little, but not much.

After several minutes though, I was in as far as I could go and my balls pressed against her ass and we were able to relax, or at least I was. It took Denise a little longer, but I waited patiently, kissing her and telling her it was going to be okay. We started fucking slowly at first, just little movements and I'd ask Denise how she was doing and soon she was saying it was good. We'd move more and when that was okay, we'd go a little harder until finally I was fucking her with long hard strokes and she'd wince a little, bite her lip and gasp, but she swore to me that she was enjoying it.

"Fuck me, David. It's okay ... It's okay ... Fuck me now..." Denise reached down to play with her cock, which was soft now, but she didn't seem to mind. I just concentrated on driving my cock in and out of that sweet tight hole as well as I could, it was fantastic, better than any of the real girls I'd had sex with and it took a very short time before I started cumming deep inside Denise's sweet little ass.

We lay there breathless for a little while, kissing and smiling until my penis fell out of her and she got up to use the bathroom. I heard water running for a long time and I drifted off to sleep only to be awakened when she climbed back into bed with me.

"I'm bleeding down there," she whispered. She sounded a little frightened and I hugged her tight.

"Are you okay? I'm sorry. I'm so sorry." I apologized and she was nodding, telling me it was alright. We fell asleep like that. But I kept waking up, I think Denise did too. After our sex, when we'd cooled down, we were both a little self-conscious maybe, unsure of what we were supposed to do now. Obviously Denise did not live as a woman, she was just a college guy who dressed up. She wasn't even gay, or at least hadn't admitted it to herself until she'd slept with me. I was feeling a little strange too, guilty maybe, and I wondered if I wasn't in fact gay, since I had just fucked a guy in the ass and enjoyed it. I was 18, but I felt like a little kid again, very insecure about myself.

When it started getting light outside I was awake again and I woke up Denise, who now looked like a guy in a bra and skirt. She'd washed her face and her wig had come off. The illusion was gone and with it any attraction she held for me, but I was nice, if not exactly loving. I woke her up and told her I'd get my dad's car keys and drive her home before all the neighbors were up. She thought that was a good idea and neither of us said very much as I took her home.

I did get her phone number, and I promised her I'd call, but I never did. That probably bothers me the most, because I had over a month before I left and I could have spent some of it with Denise, but I was so childish and insecure I couldn't bring myself to call her. I spent many a night alone after that, jerking off to fantasies of what could have been during that month.

I went to college as part of the new program to recruit officers for the military. I was ostensibly in the Air Force already, although technically a civilian. I had some military functions to perform outside my normal school routine, mostly just drilling on weekends once in awhile.

I had a girlfriend soon after I arrived, having met a nice girl in one of my classes, and that was enjoyable, but when we had sex I usually fantasized that she was a transsexual. I tried to picture her with a hard throbbing cock between her legs, instead of the little pussy she sported. I preferred fucking her from behind, spoon fashion, or doggy style, as that let me see just her ass and let my imagination run where it wanted.

It was several years before I had another encounter with a transvestite; again it was more or less an accidental meeting. I was in a bar, waiting for my girlfriend to show up. We were rather serious at that time, having been together over 18 months and she was hinting at getting even more serious. I was resisting her overtures at marriage though, and it wasn't hard to put her off. I had a very small allowance from my parents as my only source of income and I would be obligated to the Air Force for 6 years after I got my degree. It was awfully hard to make any kind of commitment based on that.

Anyway, I was waiting for her and I saw a rather attractive woman sitting alone at the other end of the bar. She'd caught my eye and apparently I'd caught hers, because she noticed me looking at her and smiled. I turned away a little embarrassed, but naturally enough I looked back and we played little eye games like that while we had our drinks. This was in a hotel bar, rather quiet and slow, and the thought did occur to me that the woman could be a prostitute, but I wasn't going to do anything anyway. My girlfriend was coming any moment, so I just sat there.

The woman was motioning for another drink and I decided what the hell, I was looking at my watch and figured I might as well do something. The bartender was passing me on his way to her and I stopped him, telling him I'd pay for her drink, if she'd let me. I ordered another for myself as well, and he nodded. He set her up and then came back to fix mine. The girl gave me a little salute with her glass and a smile and as I was smiling back the bartender leaned close.

"That's a guy, pal."

"Are you serious?" I looked back at her. She looked mid-twenties, with light brown hair to her shoulders, a nice shape beneath a plain white blouse and a pair of red bell-bottom pants made of some stretchy material. She looked pretty good, like I said, even in the fashion disaster decade of the seventies.

"Yep." The bartender chuckled and I sat there feeling a very hard stab of excitement.

My girlfriend was going to arrive and now there was a transvestite that looked great sitting less than 20 feet away, sipping a drink I'd bought for her. A moment later she wasn't sitting at all, but walking towards me, carrying her drink.

"Do you mind if I join you?" she asked and her voice was soft and slightly high-pitched, but not bad for a falsetto. I could see her Adam's apple now that she was closer and I was looking for it. But the rest of her was nice. She was about 5'8" and 140lbs maybe, a little heavy, but not terribly so. She had a good shape and I thought she was probably wearing a girdle. She was definitely passable and it turned me on quite a lot.

"No, I don't mind," I said. "But I'm waiting for someone, so..." I shrugged.

"Oh." She nodded. "Well, thank you for the drink. It was nice of you." She looked like she was going to leave and she must have thought I wasn't interested in her since I'd gotten a closer look.

"No, really, please sit down," I reassured her. "My girlfriend is coming but, um, I'd like to talk to you anyway. I mean, if you want to."

I suppose it was kind of funny really, because once she did sit down I wasted no time. All I could think of was that I'd have to ditch my girlfriend. "Are you staying here?" I asked her, even before introductions. I was keeping an eye on the door.

"No." She shook her head. "But ... I could be."

"I want to see you." I was just bludgeoning ahead, I knew, but I was feeling desperate. "I can come back here, later, I mean after a little while I just need to..." Just then my girlfriend was coming through the door. "Oh. There she is."

"I'll wait for you," the woman promised. She stood quickly and walked away, carrying her drink to a booth while I rose to say hi to Karen, my girlfriend.

"Who was that, Dave?" she asked me after I kissed her cheek.

"Who?" I turned. "Oh, her? I don't know, some girl. I think you scared her off." I shrugged and took Karen's hand and we left.

I figured I had about an hour before I'd need to get back, otherwise I was afraid the girl would be gone. She'd get tired of waiting, or picked up by someone else. Even an hour seemed too long, but I couldn't think of a good excuse to get rid of Karen. We were supposed to go eat and then see a movie, but during our dinner I hardly touched my food at all and I said very little. I hadn't done it intentionally, but it did the trick.

"Are you feeling okay, David?" Karen looked concerned and I saw my opening.

"No, I feel kind of ... Mmmm ... not too good. I don't know." I tried to put a grimace on my face, like I was suffering from some terrible malaise.

Karen's protective nature kicked in and at first I was afraid that she was going to insist on coming back to the dorm with me and taking care of me, but I managed to tell her I'd be fine. I just needed to relax a little, take some Pepto-Bismol or something, aspirin maybe, and rest. I got her in a cab to go back to her dorm, telling her I'd take the next, but it wasn't back to my room I went, it was back to the hotel.

It had been a little over an hour when I walked back into the bar and I looked around for the woman, not seeing her at first, and I frowned, feeling very disappointed. But then I saw her, sitting in a corner booth, nursing a drink and she smiled when she saw me walking over.

"I'd almost given up!" She giggled softly. "I've been hiding here since you left, wondering if you were playing a joke on me."

I sat down and shook my head. "I'm sorry, really, I..." I shrugged. "I had to figure out how to get rid of my girlfriend." That sounded pretty bad and I frowned as I said it.

"Do you treat all your girlfriends like that?" She was teasing me I hoped.

"No, not usually, but well..." I didn't know what to say. "My name is David."

"I'm Marie. It's nice to meet you." I touched her hand and held it for a long moment.

"Do you have a boyfriend?" I asked her.

"No, not really, it's hard finding someone who ... understands, you know?" She gave me a brave little smile and I thought it really made her cute.

"Do you want to go out, someplace? Um, dinner or dancing or something?" I just really wanted to be with her, I didn't care where or how, particularly. It was just exciting to be talking to her like that.

"We could just get a room," she said quietly, as if expecting rejection. "If you wanted."

I swallowed, feeling a little nervous myself. "Yeah. Oh yeah, I do. Yes." I laughed at how stupid I must have sounded. I rolled my eyes a little. "I just didn't want to seem like I was..."

"Horny?" She leaned over the table and smiled at me.

"Yeah," I agreed. "That."

"Me too." She laughed too. "Can you get it? I can pay half if you want." That made it seem very awkward and I shook my head. "No it's okay. I'll be right back."

"I'll be waiting," she sang softly, smiling.

This would be the first time I'd ever bought a hotel room just so I could have sex with someone. It felt strange, a little embarrassing almost, but I ignored it. I think it was the little bit of guilt I was feeling that I was cheating on my girlfriend like that, and not just with another woman, but with a transvestite. I knew she would never, ever understand or forgive me for that.

I returned to Marie and smiled, asking if she was ready and she was. We went to the elevators and there was an operator inside it. He gave us a look, but I didn't care at all and I just put my arm around Marie's waist while the doors closed and we started going slowly up. I think that reassured her quite a bit, that I at least wasn't afraid to be close to her in front of other people. I was sure she'd had her share of embarrassing moments, but I wouldn't be one of them.

We found our room, a small one with a double bed, a small desk, and a bathroom. As soon as the door was closed Marie surprised me, putting her arms around my neck and kissing me. I didn't try and stop her, I just went with it, putting my arms around her waist and sucking her tongue as it slipped eagerly into my mouth.

Marie was the most aggressive girl I'd ever met up to that point, certainly much more so than my only previous experience with Denise. Marie kissed me hungrily, pressing her body to mine and rubbing excitedly. I moved my hands up and down her back and finally low enough that I could cup her ass beneath the tight polyester, squeezing and pulling her to the hardness growing in my trousers.