Caution: This Erotica Sex Story contains strong sexual content, including Consensual, Romantic, TransGender, First, Oral Sex, Anal Sex, Masturbation, Petting, .
Desc: Erotica Sex Story: Chapter 1 - A former Air Force officer relates the personal story of his lifelong infatuation with transsexuals. More or less a true story as related to me by a reader who wondered if I wouldn't care to write on the subject.
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.
"Oh, God..." she breathed. "You've got no idea how hot you make me!"
I smiled at her, assuring Marie that the feeling was mutual. We made our way to the bed and she pushed me down, so I was sitting on the mattress. "Here..." She was working a the little clasp on the side of her pants, unzipping them down her hip as I rubbed her leg. It didn't bother me that she was assuming a more dominant role; in fact I found it exciting since I'd always been the one to initiate things in my previous experiences.
Marie worked her pants down and kicked them off her long legs, pressing her hands to my shoulders as she kept her balance. She wore a pair of lace red panties underneath and I could see the evident swell of her penis. She started to pull those down as well, but I stopped her.
"Leave them on, okay?" I asked and she just smiled and pulled the crotch to the side so her balls and penis came free.
She was semi-erect already and it was a good sized penis, as large as my own and she was shaved completely, even her balls. It looked incredible sexy like that and she pulled my head closer.
"Suck me!" she urged in a husky voice and I opened my mouth for her, taking the head of her cock between my lips and running my tongue around it. "Oh yeah, that's it, deeper baby ... suck my big clit for me."
Marie pushed a little with her hips and I felt it going deeper, hitting the back of my mouth and bringing a little gagging sensation. But she backed off and we tried again. It was nice and much better than what I'd expected. The idea of sucking a cock had never been foremost in my mind, but I didn't mind at all. I was so turned on by this pretty woman, sucking her cock while she stood over me, I could feel my own prick throbbing as it strained almost painfully in my now too tight pants.
I moved my hands around to her ass, squeezing her soft flesh and pulling her against me.
"Open your throat baby, come on. I want you to take it all." She kept talking to me softly and I was enjoying that too. It took a little time but I finally did get her to catch me as if I were swallowing her penis and it just seemed to pop into my throat, sliding suddenly all the way inside easily so that I could feel the silky softness of her balls against my chin.
"Ohhhh ... God! Dave ... Yeah, darling ... That's good ... Ohhh yes!" She started fucking my mouth then, every now and then causing me to gag and choke, but mostly I was able to keep my throat open and she worked her beautiful cock in and out easily. "Finger my ass, baby ... make me cum ... please! I want to cum in your mouth!" She held my head tightly while I caressed her ass, working my fingers around to her anus, probing her and finally pushing a finger against her tight little hole so that Marie arched her back and gasped.
It took her perhaps 3 or 4 minutes after that before I felt her body tightening, her ass clenching around my finger tightly. "I'm gonna cum, darling ... Swallow it for me ... Drink it all, baby!"
I wasn't too sure about swallowing sperm, but I was so into this woman by that time, so hot for her, it didn't matter. I felt her cock jerking and my mouth was suddenly filling with her hot creamy semen. It was a little salty, almost musky and the texture was a little hard to enjoy, but I swallowed it down as well as I could, spilling some and choking a little. As she finished, her spurts lessening to a slow small trickle, I kept sucking and swallowing while she rubbed my head affectionately.
"Oh that was sweet. I needed that so bad, baby!" Her cock slipped free of my lips and she hugged me to her body, thanking me.
"Now let me do you." Marie said, grinning as she pushed me onto the bed. She began undressing me as I watched her face and fingers, and lively eyes, licking my lips and tasting her sperm. It wasn't as bad as I'd feared it would be, in fact the texture of it was the only thing I didn't like, but I thought I could even get used to that.
She had me naked quickly and knelt on the bed, wearing only her blouse still, and her panties, pulled over to show her cock. She took my penis in her mouth and gave me what was a wonderful blowjob, one of the best I've ever gotten, and certainly up to that point in my life it was incomparable. She worked my cock up and down with her tongue, kissing and nibbling, even dragging her teeth lightly across my shaft until I was practically begging for her to take it in her mouth.
Instead Marie went lower, sucking my balls into her warm wet mouth one at a time, rolling them gently and using her tongue to bathe them. It was only after several minutes of that delightful torture that she returned to my cock and finally took the head in her mouth. It was so good I thought I'd cum any second, but each time I got close, Marie would pull away, squeezing the base of my cock and giggling at me as I moaned. This went on for many minutes, but I wanted her too badly to be content with that. I think the same was true of Marie as well.
She slipped herself up, straddling my body and reaching down to guide my penis to her ass. She pushed down slowly, giving her hips small circular rocking motions as it went deeper inside her tight hot ass. She was facing me and I could see her cock growing hard again, stiffening so it was about half erect. When she finally settled her ass against my hips, my cock buried to the hilt inside her rectum, she started playing with her cock for me. Stroking it while she just squeezed her ass against my hardness. I wanted to move so badly, to fuck the daylights out of her, but we didn't. We were very still; except for my hands digging into her hips and her own hand rubbing her cock slowly up and down.
"Do you like my cock, baby?" she'd ask me, rolling her ass slightly and making me groan with pleasure. "Do you want me to cum all over your hot body?"
"Oh yeah, do it." I was in heaven right then, staring at her as she teased me.
"Mmmm ... your cock feels so good in my ass. Fuck me now, baby. Fuck my tight little ass..." She started lifting up and pushing back down, riding my cock as I held her hips, now free to thrust up inside her. It felt deliciously wonderful to be doing that, stuffing her tight ass with my prick over and over.
"I'm going to cum!" I told Marie all too soon, pulling her down hard against me as I lifted my ass off the bed, trying to drive my dick as far inside as it could possibly go before unleashing a flood of semen. I was panting as my balls emptied and Marie fell forward, her mouth finding mine and we kissed hard while I came. I held her ass in my hands and it felt truly wonderful.
A few minutes later, once we'd regained our senses, Marie climbed off me and went into the bathroom, returning with a washcloth wet with warm water. She washed my penis gently and then smiled down at me as she removed her blouse and then her lacy red bra. She had no breasts of course, but she still looked beautiful to me, standing there naked now but for her panties. Her cock was hard again and she massaged it slowly.
"Have you ever been fucked, David?" She grinned and I shook my head no. "Roll over then, I want to do you like a little bitch." She giggled and I wondered if it was going to hurt, remembering how Denise had reacted when I'd taken her anal virginity. But I knew she'd been enjoying it by the end also and I wanted to please Marie.
I rolled over and Marie had a small tube of lubricant that she got from her purse and squirted some onto her fingers, massaging it into my ass. "I haven't fucked a virgin in a long time," she told me. "This is going to be nice!"
I was nervous and my body was stiff, despite Marie's attempts to get me to relax. "Shhh ... It's gonna be fine, baby. You'll see. Just relax and let me get inside." I could feel her cockhead pressing insistently at my anus and it seemed as if she was trying to push a baseball bat inside me.
"No, stop, please ... This isn't going to work, Marie." I groaned, and actually tried to crawl away a little, but she just laughed softly and held me tight.
"Yes it will, you're going to be a little bitch for me now, okay? Just a little girl for my big cock ... Come on, darling ... that's ... uh! ... it!" And suddenly I felt the head pushing me open and popping in. I gasped loudly and with that Marie started applying pressure that never seemed to ease up. It burned slightly and I felt as though I was being split apart, but it wasn't totally terrible either. "Oh yeah, baby ... you're ass is so nice ... give it to me ... Give me that tight ass ... Uh-huh ... Push it, baby. Push against my cock! Fuck yourself on it!" She slapped my ass and giggled when I jerked slightly.
"Oh fuck!" I gasped, wriggling beneath her. "It hurts Marie ... stop ... just ... wait ok? It hurts a little."
"Just a little?" She shifted her body and got a better grip on my hips with her strong hands. "Here it comes, baby!" And then she suddenly started fucking hard, really working her cock inside me so that every push felt like a sharp little stab in my bowels. "Almost there, baby ... Almost ... Take it for me!" She pushed a few more times and then stopped. I was bathed in sweat and she was all the way inside me. I reached back, between my legs to feel her balls pressed against me.
"That's not so bad, is it?" she whispered and rubbed my back, letting me get used to her.
"No," I breathed. "I like it." And I did like it, that was the thing. It hurt a little and I was afraid she'd torn something inside me, but it felt great now, being filled with her cock like that.
When she started fucking me, it was only mildly uncomfortable and I was soon taking her easily. She'd done this before, obviously, and she had a nice way of moving that seemed to find the right spot inside me, stimulating my prostate and making my shiver a little with the sensation. Marie fucked me slowly at first, but soon we were fucking hard, and I loved it, pushing my ass back to meet her cock and arching my back with the effort while she pushed and pulled my hips. It was a wild fuck and she kept talking to me the whole time, calling me her little bitch and cock slut, telling me how she was going to cum inside my ass and make me her little cum whore. It was outrageous and nasty and an incredible turn on. No one had ever spoken to me like that during sex.
When Marie finally did cum, it was an intense sensation. My bowels suddenly filling with a wet warmth that just seemed to spread out. She pulled out afterwards and I could still feel it, kind of a weird greasy feeling that felt rather dirty, considering it was in my ass. But I largely ignored it because Marie had washed her penis and we were just lying on the bed cuddling for awhile.
We talked for while and I found out Marie worked for the local newspaper. She was openly gay and lived as a woman, but had no plans to have a sex change or anything. That was a much bigger deal back then and enormously expensive, but she was happy being what she was. She told me the only thing she wished she could change was her breasts, she really wanted to have tits someday, but even that was a rather exotic operation in 1974 so she doubted it would ever happen. I told her I thought she was very attractive any way and she laughed at me, reminding me that I'd still wanted her to keep her panties on. She understood that it was to help keep the illusion for me, but she didn't mind.
Marie had been with a few straight guys and she said she actually preferred them over gay men, simply because it was more satisfying for her. A gay guy just saw her as another guy who dressed funny, but a guy like me, she said, saw her as a woman first, who just happened to have a penis. That was how she liked to think of herself as well. It was interesting, just talking like that, because I really didn't know what my thought processes were, but Marie seemed to understand me pretty good.
I made love to her again that night and then in the morning I gave her another blowjob before we went our separate ways, Marie home to change for work, and me to get to school. I had her phone number and I promised to call her, but I wasn't sure she believed me. She told me she'd had a lot of one night stands, so if I was going to be just another one, she could deal with it. She seemed a lot more defensive when we parted and I think it was just her way of preparing for the worst. I've found that most TS/TV's have had more than their share of disappointments and it tends to make them a little wary of anything that seems like a good thing.
I spoke to Karen that afternoon and she pretty much nailed me. She'd tried to get in touch with me at the dorm the night before and when she couldn't, she was worried and came over personally. Obviously I hadn't been home all night and she asked me where I'd been. I've always been a real crappy liar, that's why I don't play poker. She knew I'd been with someone else, but I refused to say who. It didn't matter; she told me she needed some time. Basically breaking up with me without breaking up, the way women do. They don't dump a guy until they have another one lined up I think, or maybe I'm just cynical when it comes to girls. Transsexual have always treated me a lot better. Of course, who am I to talk? I did cheat on her.
I called Marie that night though, conscience or no conscience, and we started dating. We kept it very low profile of course, more for my sake than hers, since she was out already. I had to worry about someone finding out and reporting it to the Air Force, because being gay, which is what they would have called it without question, was a big no-no. This was a long time before 'don't ask, don't tell' and if that happened I'd have to repay my tuition up to that point and basically drop out of college, because I couldn't afford it on my own.
But it worked out though, because once we'd gone out maybe 6 or 7 times over the next month, getting a hotel room every time, Marie became comfortable enough that I could stay at her apartment. I really enjoyed being with her, and I spent almost all my money buying her lingerie, believe it or not. I loved seeing her dressed in stockings especially. Perhaps the only thing I had problems with, and I didn't bring it up for several months, was the way she could get very dominant.
I didn't mind so much the talk, it was kind of exciting, but sometimes it went beyond that and she would enjoy spanking me while she fucked my ass, or really hurting my nipples, pinching and twisting them, even biting them sometimes, so that they would become very tender and puffy for days afterward. I enjoyed it to some extent, but Marie loved it a lot. She also wanted to see me dressed, in panties usually, which I resisted because I just had no urge to cross dress at all. I did it a few times, and when I did Marie would really say the most degrading things, calling me her faggot cocksucker, sperm drinker, and worse. It kind of bothered me a little and when I tried talking to her about it she shrugged it off, telling me she was only kidding and that she really loved me, so I should be enjoying it too. But I wasn't.
I think part of her thing was that I was fundamentally a straight guy, in as much as men did nothing for me at all. Even transvestites, unless they were passable in public, like Marie was, turned me off completely. So for Marie I was just a straight guy that she could humiliate, maybe representing all the guys who'd given her a hard time as she grew up being gay, or something, I don't know. But it didn't seem entirely healthy to me.
Our break came about 6 months after we'd started dating, it was a little thing really, but we'd argued the way people sometimes do. The difference was neither of us was willing to get over it, the way normal people would. I was maybe looking for an excuse not to see her anymore, and I don't know what Marie's reasons were, but either way we didn't talk for almost a month. Then she called me and we went out and talked, and ended up in a hotel room, but the sex wasn't really great, like it had been before. But we were at least friends again, which was good because a few weeks later she introduced me to a friend of hers who lived in a city about an hour away.
Heather was a pretty girl, one who probably should have gotten a sex change, but didn't. (As far as I know – she might have by now) She was 28, quite a bit older than my 21 years, but that didn't matter at all. I met her at Marie's apartment and they knew each other through a transgender support group, which was the first I'd ever heard of one of those. Marie had called me and told me one of her best friends was in town and she thought I'd like to meet her. I was kind of iffy on it, not really sure what was going on, but I agreed to come over.
Heather was about the same size as Marie, 5'8" and 135lbs if I had to guess, with a great body, especially her legs and ass. She was wearing a little white miniskirt and sheer nylons, which I liked a lot. A blue tube top with very small breasts, like barely A cups, but they were real and they were hers. She had blond hair, wavy and falling down past her shoulders, and bright blue eyes. Her face was very attractive, completely feminine and she looked great.
Marie introduced us and we spent the evening talking, having a little dinner and drinking some wine. Heather was a beautician and had been living as a woman for almost 10 years. She had a lot of great stories, some sad ones, but mostly funny ones about her experiences. She'd started cross dressing when she was about 6 years old, she said. Her mother would dress her and she'd go to her sister's room and change as soon as she could. She knew she was supposed to be wearing dresses and couldn't understand why her parents didn't.
Heather had just broken up a few weeks before with a boyfriend she'd had for about 3 months. She laughed and said three months was about average, so maybe she shouldn't complain, but it was still hard. It took her a long time to meet an understanding guy. She was very passable and she'd been hit on a lot, but when guys found out about her little secret ... that was it.
We seemed to be hitting it off pretty good and Marie was encouraging us, letting Heather and I carry the conversation, interrupting once in awhile just to point out that one or the other of us had a similar interest, or experience. Marie was totally cool that night and it really is a testament of her friendship, not just to Heather, but to me as well, that she went to so much effort to get us together. I have a hard time imagining any of my real girlfriends doing that.
By the time it started getting late enough that I figured I should be going I realized we'd drunk so much wine that I was in no condition to drive, or maybe that was just a good excuse, because I felt very lucid. Either way, Marie insisted that I stay the night. She and Heather would have the bedroom and I could sleep on the couch. It seemed reasonable to me. Heather protested a little, wondering if Marie and I shouldn't share the bed, but I said I was fine on the couch.
I was having a hard time falling asleep, thinking about Heather, and a little bit about Marie, but mostly Heather and how wonderful she had seemed. It was a half-hour or so later that I was surprised to see Heather walking into the living room in the darkness. The only light came from a small light above the stove in the kitchen and it took me a moment to recognize her. She was wearing a big t-shirt that fell down about mid-thigh and she looked incredibly sexy like that. I sat up and she sat down next to me.
"Hi," she said. "I couldn't sleep. I didn't wake you up did I?"
"No, uh-uh, I couldn't sleep either." I smiled a little sheepishly.
"Marie was telling me you guys were kind of breaking up."
"Yeah, a little I guess, but we'll always be friends," I told her, despite how corny it probably sounded. "I like Marie a lot."
"Yeah, me too." Heather nodded and we kind of sat there in silence for a long minute or two. "Look, um, I think you're really nice."
"I think you're great," I said quickly, maybe too quickly and I felt kind of tongue tied and nervous. I was trying to think of what I should say when Heather just leaned over and started kissing me.
I soon had my arms around her and I leaned back on the couch, pulling her on top of me. Her mouth tasted sweet and fresh, she'd just brushed her teeth I realized and I wished I had, but it didn't seem to bother her and I soon forgot about it. We were moving around a little and she worked the sheet that was covering me off so that I was just in my briefs underneath her. I pulled her t-shirt over her head so heather was just in her panties, and I loved the way her small breasts felt against my chest.
I rubbed her back, moving my fingers along her spine as we kissed and I could feel my cock already hard and pressing against her crotch. I slipped my hands down to her hips and started working her panties down and she lifted herself up to help me, sliding off me momentarily and she removed her panties while I quickly got out of my briefs, freeing my stiff penis.
She moved back on top of me and this time I became aware of her own penis, smaller but no less hard than mine, trapped between us like mine was. We kissed a long time, humping our bodies together slowly and I loved the feeling of our cocks sliding together. I pulled her up a little, so I could play with her tiny breasts. They were the size of tangerines maybe, just bare handfuls with dark hard nipples and I sucked them gently while she rubbed her cock against my stomach, moaning softly and cradling my head to her body.
"Do you want to make love to me?" she asked, and of course, just then I wanted that more than anything.
She got up and went to the bedroom, getting the tube of KY that Marie kept next to the bed and came back smiling. She got my cock nice and slick and then applied some to her ass. Heather got back on top of me and guided my cock into her warm ass and pushed herself down on it slowly, while I just lay there quietly, letting her take me at her own pace.
"You're nice sized," Heather decided. "Just what I need. Not too big, not too small ... Mmmmm..." She sighed as her body settled against mine. "Perfect."
"You're perfect!" I pulled her down so I could kiss her while I started thrusting my hips, working my cock in and out of her slowly. She was so different than Marie. Quiet and controlled, very passionate the way she kissed, working her tongue delicately around my mouth and her body felt so good wrapped around my cock. Neither of us was in a hurry that first time, we just moved slowly, really enjoying the sensuality of it.
After a good 10 minutes though, I think we were both ready for more and we shifted around, keeping my cock inside her, so that I was sitting up and Heather was straddling me, facing me with my hands on her ass. She started grinding me hard while I pushed and pulled my straining cock rapidly in and out of her hot hole. I sucked her little tits, moving from one to the other until she was gasping loudly. If I hadn't known better I'd have thought she was cumming right then. The thought turned me on completely and it didn't take long until I was trying to hold back, feeling my balls tightening and then letting go finally, spilling my seed into her wonderful ass and making me groan with the pleasure of it. Heather continued to rock her hips against me even after I'd stopped and the motion kept me from going soft.
I smiled and kissed her hard and we were fucking again, as if I hadn't cum at all, it was incredible. I could feel how hot she was, and tight, and now my cum was inside her, adding a wonderful wetness. We moved around again, getting down on the floor so we could do it on her back, with her long beautiful legs over my shoulders. She stroked her cock while I fucked her and soon she was hard as a rock, her hand flying up and down the shaft while she panted beneath me. I was going to cum quickly this way, really fucking her hard as there was no resistance at all. Her ass felt just like a pussy then, wet and hot and just tight enough to feel good.
Heather brought herself off, shooting her cum up onto her heaving body and a moment later I was cumming again too, spraying more of my seed into her ass to mix with my previous load. It was a great fuck, one of the best I'd ever had, and I leaned down to kiss her and tell her so. She agreed, smiling and kissing me, telling me it had been wonderful for her too. I pulled the pillows and the sheet and blanket down off the couch and we wrapped ourselves up, snuggling close and falling asleep together.
When I woke up, Heather was still beside me, lying on her side facing away from me. I turned towards her, getting close and enjoying the warm softness of her body. I had my usual morning erection and it pressed quite naturally into the crack of her ass and I just put my face in her hair, smelling her and giving tiny little pushes with my hips, because it felt just too good not to. I don't know when Heather woke up, but I could feel her moving her legs slightly, spreading them just a fraction so my cockhead could find her anus and I felt her pushing back a little.
I gave a hard little push and felt her sphincter giving way reluctantly, but soon my cock slipped inside her ass and as it did she turned her head, smiling sleepily at me. "Mmmm ... good morning to you too." She said and I gave her a little kiss as I pushed my cock slowly all the way inside her. We fucked leisurely for some minutes and then gradually began picking up speed until I was thrusting hard inside her and finally cumming, pulling her tight to me as my balls emptied for a third time into her sweet little ass.
"That was a nice way to wake up." Heather smiled at me a minute later. "Thank you."
"Yeah. For me too," I said, returning her smile. I couldn't believe how lucky I was. I never wanted to let this little girl go.
She finally did get up though, when we heard Marie moving around in the bedroom. I looked at Heather and she looked at me and I think we were both a little worried about Marie's reaction. Heather went into the bathroom to shower and I put on my underwear and pants and went to the kitchen to start some coffee.
Marie came out a few minutes later, smiling and giving me a cheery good morning and a kiss on the cheek. "So? How did you sleep?" she teased, knowing I was sure that I'd slept pretty good, after a fashion. "Don't worry, I'm happy for you guys," she said, before I could answer. "Why don't you go get a shower, you smell like sex."
"Uh, Heather's in there..." I must have looked like an idiot.
"Yeah? So?" Marie shook her head with a wry grin. "Hurry up, I want a shower too."
I went to the bathroom, knocking on the door and opening it. "Just me." I said.
"Oh. Where's Marie?" Heather peeked around the shower curtain.
"In the kitchen. She's okay. She told me I needed a shower." I grinned and took off my pants and briefs.
"Oh, um, well..." She laughed a little self-consciously as I slipped into the shower with her. We both looked down at her erect penis; it seemed pretty obvious she'd been masturbating.
"Oh." I smiled and maybe blushed a little. I'd been caught by Karen, my old girlfriend before, jerking off in the shower, and it had always embarrassed me, although she'd just rolled her eyes. But I thought I'd try something else. I went down to my knees and took her hard cock in my hand. It was maybe 5" long and uncircumcised. I pulled the foreskin back and brought my mouth to it, kissing it gently.
"You don't have to do that," Heather started saying. "If you don't want to, I mean..."
"It's okay. I want to make you feel good." I smiled up at her and took her in my mouth, sucking as gently as I knew how. I was actually pretty good at it after being with Marie for so long and it was a lot easier with Heather's smaller penis. It only took a few minutes to make her cum and she tasted good, different than Marie, a little sweeter I thought, a little lighter, but perhaps that was caused by the hot water running over us too, I didn't know.
I stood up and we kissed long and hard, Heather didn't seem to mind that I'd just had my mouth full of her cum. "I can't believe you did that for me," she said, smiling. "Marie told me you were straight."
"Yeah, I am," I said. "I don't mind though, I wanted to make you feel good." I guess Marie hadn't told her about all the times I'd sucked her off and I felt a little grateful for that, although I didn't understand completely why. I'd pretty much assumed that Marie had told Heather everything.
"Oh yeah, you did, you did!" She kissed me again.
I'd have to say that Heather was the first transsexual I could have seriously fallen in love with. In fact, I was in love with her. We were together all the way up until I left for officer training after I graduated college. For nearly two years we spent pretty much every weekend together when I wasn't off for training and every school break I'd go up to her place, only to return with great reluctance. We spent our summers together, although between my junior and senior years I had to spend 6 weeks at an air force base in California, and that separation was almost unbearably difficult.
After I went to the Air Force we stayed in touch, mostly through letters, but it was hard, and after a few years we gradually fell out of the habit. Heather made no demands whatsoever on me to do the things Marie had. She didn't particularly want me to go down on her penis, although she was a huge fan of analingus and I ate her ass regularly before we had sex. She never once had me anally, although I offered to let her do it if she wanted. Heather was just into being a woman for me and that was perfect, really, exactly what I was looking for as well, and she really set the standard by which I judged all my other experiences.