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    Default Straight guy seduced by a transvestite

    This is a story about Troy, a guy who's clever but very naive. He's clueless about being manipulated, and meets a "woman" named Roxy whom he thinks is a pre-op transsexual but is really a transvestite.

    Roxy sees through Troy immediately, and easily manipulates him into having sex with her. Troy never suspects a thing.

    Straight Guy Tricked Into Having Gay Sex

    Hello, my name is Troy. I'm going to tell you about my sexual experience with a member of the same sex. It happened last summer, two weeks after my 23rd birthday.

    I had never seriously considered having sex with a guy. Men didn't attract me, and cocks didn't interest me. I've always loved women and had always been straight as an arrow. I was pretty open-minded about homosexuality, though, and would never hold being gay against anyone. I even supported gay marriage.

    Anyway, I was between girlfriends and decided to go to the gym to work out and maybe meet someone new. I had a great workout, but didn't meet any women there who seemed interested in dating. As I left the gym, I once again saw the neon sign for The Gemini, a nightclub just down the street. Many times as I left the gym and saw that sign, I wondered what the place was like, but I had never gone in there because there are several bars and clubs near my apartment. Feeling horny, I decided to give The Gemini a try.

    It was pretty dark in there, even for a bar. All the seats at the bar were taken, so I sat at a table near the bar. I ordered a drink, and proceeded to look around. There were several reasonably attractive women in sight who weren't with a man. A couple of them had fake-looking breast implants. I love breasts, but implants are sort of a turn-off for me. Then I spotted one I really liked, standing at the bar talking to two women on barstools.

    She was about 5'6" or 5'7" and had straight, black hair that came down a few inches past her shoulders. Her skin was tanned and her eyes were big and dark brown. She was slender above the waist and her bra size was probably a B or C cup. Nothing wrong with that—I'll take smaller boobs over big fake ones any day! She had full lips and a cupid's-bow mouth.

    She also had a very round ass and well-toned legs, which were shown off well by her short skirt. She was talking to two other women, one of whom glanced at me and then did a quick double-take when she caught me checking out the raven-haired woman in the skirt. I was a little embarrassed, so I just smiled shyly at the one who did the double-take, then looked away. My waiter was bringing my drink from the other direction. I got my drink and set it on the table. The waiter asked me if I'd like to try any appetizer. I told him not now, but maybe later. He asked if I wanted menus, and I said no. He said, "Just the one drink, then?" I thought that was an odd thing to say. I replied, "No, I'll probably have a few more later, unless you were wanting me to leave as soon as I finish this one."

    The waiter looked up and past me, then looked back at me and said, flustered, "No, I didn't mean that, sir. I apologize, that's not what I meant at all, you're welcome to stay as long as you'd like."

    "what the hell was that about, then," I wondered. I picked up my drink and turned to look at raven-hair again, and damned near spilled my drink when I saw she was standing at my table looking at me! She smiled and said "Sorry, did I scare you?" I noticed that her voice was surprisingly deep. I said, "No, I just didn't know you were standing there. My name is Troy, can I buy you a drink?" Her smile widened and her eyes sparkled as she sat down and said "Well, Troy, I thought you'd never ask." I thought to myself, all right Troy! This one's hot and ready to go!!

    She told me her name was Roxy and she worked as a nurse. As she was speaking, I noticed a slightly larger-than-normal Adam's apple. I looked at Roxy's hands, and then I tried to decide how I should let on what I had just realized.

    I asked, "Roxy, have you been in the military, and have you ever played a rough sport like football or hockey?" His jaw dropped open for a second and he looked pissed, then the pissed look quickly passed and he started looking at my face intently. "Who are you and how the hell did you recognize me!?" he demanded. Now it was my turn to look surprised, then I realized what he thought. I replied, "Oh, no. It's nothing like that; I'm not someone from your past. It's just that I watch a lot of shows about medical procedures, like "Plastic Surgery: Before and After" and I've learned that male-to-female transsexuals often join the military and engage in very masculine activities in order to hide their desire to be feminine, which a lot of people have a problem with."

    He looked concerned and asked what gave his away. "Was it my voice?" he asked. I replied, "Your voice was the first clue. When I began to suspect, I looked carefully at your Adam's apple and your hands. They're all unusually large for a woman, but about normal for a man. Are you pre-op or post-op?" He replied, "I'm pre-op, handsome. Does that bother you?"

    I said, "Not at all, in the sense that I have no homophobia. Unfortunately I don't have a gay bone in my body, so it doesn't look like I'll be getting some tonight." Roxy seemed to look at me like I had just become more interesting to him. I didn't think anything about it at the time.

    He said, "How do you know? Have you ever tried it?" I replied "No, but I know because I've never wanted to try it. I've tried to imagine having sex with a guy just to understand what it would be like, and it never aroused me in the slightest." Roxy flashed me a huge grin and said, "Well, I guess I won't be getting any tonight either, then."

    After that we talked for a while and we each had our share of drinks. I wondered if he expected me to still pay for them, then decided I would pay regardless. I did invite him, after all, and it was nice to have some companionship. It turned out we liked a lot of the same things.

    About eleven PM, he said he'd probably be getting home soon. "I won't invite you to come home with me, because I don't want to scare you again," he said. I looked at his face for a trace of humor, but he seemed completely serious. I said, "That wouldn't scare me. I already told you, I'm not homophobic, I'm just not gay." He gave me a slightly pitying look and said, "Sweetheart, if you've never tried it, you don't know. Imagining it is different than trying it. If you really weren't scared of finding out, you'd have tried it by now." Well, that pissed me off. I don't like anyone telling me I'm scared of something I'm not scared of, or telling me I don't know myself.

    "Look buddy," I said, "You don't know me and you don't know what the hell you're talking about! I only came in this place because I didn't know what kind of bar it was. I'm not curious about my sexual orientation because I know exactly what it is! Don't try to tell me I don't know myself. Hell, you JUST met me, what could you possibly know about me!?"

    He smirked and said, "Well, if that's true, then why are you getting so upset about it? It seems to me you've got some emotional conflict there, and I just can't imagine what it could be." Now I was REALLY steamed, because he had me. If I responded with more anger, I'd just be proving his point. But I couldn't listen to him say that shit about me and just let it go, so I forced myself to act calm and I said, "All right, maybe I do have an 'emotional conflict' over people acting all smug and superior, like they know me better than I know myself, but it has nothing to do with any fear about being homosexual. I'm just not turned on my males, cocks and balls don't excite me in the slightest. I couldn't have sex with a man if I tried, because I'd never get hard—there's just no attraction there."

    He faced straight at me, looked disgusted and said sharply, "What utter bullshit. Enjoy living in your delusion, I'm going home." As I sat there with my jaw in my lap, he opened his purse, took out some money and put it on the table. "That should cover my drinks, hon. Have a nice, straight little life."

    I was still pissed, but now I was feeling quite a bit of shock over having been spoken to like that, and I had this feeling that if I let Roxy get away with having the last word, somehow he'd win and I'd lose. I couldn't let that happen! I thought of what I could say. I got an idea.

    "Look dude," I said, "I can easily prove you wrong. I'll go home with you and if you can get me fully erect, I'll have to admit you're right. But when you realize you can't give me a boner, you have to apologize to me."

    He narrowed his eyes and studied me for about ten seconds. Then he frowned and said simply, "That seems fair," and started walking toward the door at a very fast pace. I quickly took out more than enough money for my drinks and the tip, tossed it on the table and went after him. He was walking fast and I was behind so I didn't have time to stop and think about what I was doing. I jogged a bit to catch up, and by then we were at the entrance to his apartment building. He only lived half a block from the bar!

    Neither of us spoke as we entered the building. I followed him to his apartment and noticed his hands were shaking a bit as he unlocked the door. "He knows he's going to lose this bet and take back the shit he said about me," I thought. Later, I guessed he was thinking something else entirely at that time.

    As we entered the apartment, he turned on the lights about halfway, I'd guess. The light switch was one of those dimmer switches. "Have a seat and relax." He said, "I'll be right back." I sat on the couch and looked for the TV remote, but didn't see anything other than some magazines and a remote for the stereo on the end table. I clicked the stereo on, and it was set to a radio station I liked at medium-low volume. Nice. I then turned on the lamp on the end table and started looking through the magazines. Most of them were hardcore gay sex mags, big, beefy body-builder types with horse cocks sucking and fucking each other in every conceivable position, often with three or four guys in on the action. I admired the guys' builds, as I've worked on mine for some time and have a pretty hard body, but didn't feel in any way turned on. Then I saw a magazine titled "She-Male Sluts" and looked through it.

    I had to admit, some of the models in that mag were hot. If I couldn't see their dicks, I'd never have known they were male. In one photo layout, a particularly sexy shemale with realistic-looking tits and a nice, curvy ass was standing, slightly bent, and facing to the right. The "guy" guy in the photo looked a little like me, and he was standing behind the shemale with his dick in her ass. Er, I mean his ass. From the angle, you couldn't see the shemale's penis and I was thinking of him as though he were a woman. I realized that without the male genitals in sight, I could probably pretend he's a girl, get hard and fuck a guy that looked that deliciously female! On another page, "she" was straddling him, riding his pole, and again, "her" genitals weren't visible. I imagined fucking Roxy from behind like the first picture and started getting hard. "Dammit," I thought, "Now what do I do? Would I rather get my rocks off and let Roxy think he's right, or win the argument and make him apologize?" At that moment, someone touched my shoulder and I nearly jumped out of my skin—I could hear Roxy doing something in the kitchen and I thought we were alone!

    When my head jerked around, I could see it was just a cat. He was mostly black with some white. I scratched his ears and he purred appreciatively. Suddenly, he bolted for the kitchen. I didn't hear anything, but I bet the kitty's super-hearing picked up the sound of a can opener in the kitchen.

    A little while later, I heard a blender running. Shortly after that, Roxy came out with frozen Margaritas.

    As he approached and handed me my drink, I looked at him and wondered if I could I could pretend he was a woman. I tried it and realized that I probably could, and that the Margarita wouldn't hurt. "Fuck my pride," I thought, "I'm horny and I want to get off."

    He sat down about a foot away from me and we sipped our drinks for a while, making small talk. When we finished the drinks, he asked if I wanted another. "No thanks," I replied, "That was delicious, but I don't want to drink too much because I have to work tomorrow." We continued to make small talk for a few minutes and then Roxy said, "Well, I guess I'll be making the first move." He took my face in his hands and looked into my eyes. His face was amazingly feminine, and he was wearing just enough makeup to enhance the feminine features. I might as well have been looking into the face of a woman! I pretended he was a woman, and then he started to kiss me. I started to kiss him back. Something seemed wrong. Then I realized—Roxy smelled wrong. I had never noticed it before, but up close, women smell a certain way. They smell like women. Roxy had a barely detectable smell and was wearing a very small amount of perfume, but there was a guy smell. I couldn't pretend he was a woman as long as I was close enough to kiss him. Maybe my plan to fuck him wasn't going to work, and I'd win the bet after all. That was little consolation, as I had already mentally promised "Mr. Happy" that he'd be doing some butt-pumping tonight, and Mr. Happy doesn't like to be disappointed.

    Roxy could tell I wasn't into the kissing, so he stopped. He looked at me and said with genuine concern, "Are you sure you want to do this?" I said, "Well, I guess I'd like to show you that you're wrong about me. Can you handle not being able to get me aroused?" Roxy continued to look concerned and said, "Don't worry about me, sweetheart, think about whether or not you really want this question answered." I wasn't sure what he meant, so I shrugged. "All right then," he said, "Take off your clothes." I had a sudden impulse to bust out laughing but I hid it. This was so absurd, and he was being so serious about it. I stood up, took off all my clothes, and sat back down. Roxy gazed at me for quite a while and said, "You have a terrific build, and your cock looks delicious. Now it's my turn."

    He stood up and began taking off his clothes. First he took off his shirt and bra, and I was dismayed to see that what I thought were natural-looking implants or hormone-induced breasts were bra inserts. Roxy was completely flat-chested and unmistakably male. I was a bit disappointed--I thought he was a she-male or pre-op trenny, which if I understand correctly means a man who has begun altering his body with female hormones and/or breast implants. I was curious to see what his tits looked like, now I find out he doesn't have any. Well, at least I'd win the bet, I thought. Without his clothes, he's just a guy with a feminine-looking face and makeup!

    Then he took off his pants, and I saw he was apparently wearing a bra insert in his underpants, too. But when he took the underpants off and his cock flopped out, I saw that there was no insert—Roxy had a huge cock, much bigger than my own. He was completely hairless below the eyebrows, and the lack of pubic hair made his maleness all the more obvious. It was mostly soft, but as he stood there in front of me it started to swell and grow even bigger. Roxy was getting hard right in front of my face. I didn't feel any arousal. I liked up at him and shrugged. "Let's switch positions," he said. He sat on the couch and I stood up and faced him. He stared intently at my cock as though he could make it hard through sheer force of will. I didn't feel the slightest bit horny. He placed his palms on the front of my legs just above the kneed and slowly started to slide them upwards. He got to my waist and slid them back down. He repeated this a few times and I started to feel something. He then moved his palms to the insides of my legs and slid them slowly up and down my thighs. His hands felt very soft and slightly cool on my skin. I was definitely starting to feel something. He continued to do this, each time going up a little farther until he was touching my balls each time. I could feel Mr. Happy start to stiffen. At that point I actually considered saying "All right, you win, you proved your point" then grabbing my clothes and bolting for the door. I ended up staying right there, my cock getting harder and harder as this guy stroked my thighs and gently touched my balls. Soon I was rock-hard and throbbing with desire. I kept waiting for that "I-told-you-so" smirk, but it never came. As I looked down at Roxy, he seemed at the moment to be completely uninterested in anything above my waist. Pretty soon I was longing for his soft hands to caress my throbbing pole. Instead, he licked his lips and started sucking on it! I was reeling with desire and confusion. I'm not sure what I expected, but I was surprised to find that his mouth felt exactly the same as a woman's. Of course it would if you think about it, but for some reason I expected that a guy's mouth would somehow feel completely different!

    Pretty soon I realized that if he kept this up I was going to come. I was having very mixed feelings. I was horny, confused, and had a sort of sick feeling deep down. I never imagined anything could feel so right and so wrong at the same time. "All right, you win," I said. "I guess you were right. You can stop now." I started to pull out of his mouth but he grabbed my ass and forced my cock deeper into his mouth, bobbing his head faster as his hair swung back and forth. It felt so good, I couldn't resist any longer! I just let him keep sucking away furiously, and felt myself getting close to orgasm.

    Right at the point where I was just about start my climax, he stopped suddenly, and said "Lay down on the floor. I want you lying on your back when you come in my mouth." I couldn't have done anything else if I'd tried—I was so horny I was shaking all over, and practically fell on my way down to lying on the floor! I noticed Roxy's cock was fully erect and throbbing now. Roxy knelt by my head, facing my feet, then got down on his hands and knees He took my cock in his hand and started sucking very gently on the tip. I was going crazy with lust, there was a huge orgasm trying to bust through but Roxy wouldn't open the door to let it out. I tried to thrust into his mouth but he tipped his head back so I couldn't. "You want to come?" He asked. "Yeah! HELL yeah!" was all I could say. He moved one knee to the other side of my head, so one of his knees was on each side of my head, with that monster dong right over my face. "The only way you're going to come tonight is with my cock in your mouth." I was hornier than I've ever been in my life and RIGHT on the edge of orgasm, so I didn't think about it for a second, I immediately grabbed his pecker and put it in my mouth.

    He thrust it deeper into my mouth and at the same time began furiously sucking my own throbbing member. I started to come instantly. My whole body was contracting with each wave of orgasm and each contraction made me start to sit up slightly, involuntarily forcing Roxy's dong even deeper into my mouth. I had to make an effort not to clench my teeth on his dick, because every muscle in my body was trying to contract at once with each wave. I came screaming, a hundred times harder than I ever had before, and it felt like all the fluids in my entire body were gushing through my prick into Roxy's warm, soft mouth. It felt like it would never stop! My cries were muffled by the fact that my mouth was stuffed full of his dick. When it finally ended, every muscle in my body felt weak and tingly, and my head was spinning. Roxy held my cock in his mouth as I started to go soft. My mouth was still packed by his dong, and I wondered if he thought I was going to give him a blowjob as well. I suddenly felt the confusion and sick/wrong feelings I had before much more intensely, because all my horniness had drained out into Roxy's mouth. I out my hands on his belly to indicate I wanted him to move off me. Instead, he started flicking his tongue around my cock, which was now completely flaccid. The wrong/sick feeling intensified. I started to push him off me. He bit down on my dick gently but firmly, biting harder each time I tried to push him away. The message was clear, Roxy wasn't done with me and if I tried to resist, I'd be in a world of hurt! I thought he might at least let me get his schlong out of my mouth, but when I tried that, the teeth came back. I considered biting down on his, but didn't want to provoke him further. I decided to let him do what he wanted—he couldn't keep me there forever, and maybe I sort of owed him for that earth-shattering orgasm he'd just given me. He started thrusting in and out of my mouth then, while his tongue still worked on mine. Several minutes went by like this, and he started tickling my balls and playing with them too… Pretty soon I was amazed to find myself getting hard again!!

    Roxy sucked faster, and thrusted into my mouth faster too. Fortunately, he wasn't trying to get the whole thing in, I'd choke for certain! He had my cock as hard as a diamond now, and getting a boner so soon after such a powerful orgasm sort of ached. It wasn't a good kind of ache, either.

    Roxy stopped tickling my balls and began pressing my anus with a finger. I didn't want that so I clenched up, but he was persistent and wriggled it in. He started to finger-fuck me, and pretty soon he had two fingers in me.

    I decided to get this over with as soon as possible, so I firmed up my lips, making my mouth a tighter hole so he'd come more quickly. He started moaning, and I started moving my head in time with his thrusts, forcing that thick cock farther and farther into my mouth. I started gagging, but that seemed to turn him on even more so I just kept trying to get it deeper with each thrust. The ache in my cock was getting worse, and I tried to make my lips even tighter and take his pole deeper into my mouth so I could get this over with. Pretty soon, I could feel his shaft penetrate the back of my mouth and go a little ways into my throat with each pump! I really started to gag then, and something else was happening—that ache in my prick was turning into the feeling that I was going to come again!! Roxy seemed to sense this and started sucking harder and faster, and at the same time pumped my ass with his fingers more vigorously. I started breathing faster and let out a moan, and began to have a second orgasm. Without any warning, Roxy made a powerful, convulsive thrust deep into my throat, and I could feel his cock pulsating as he came at the same time as me. I can't even describe how hard I came as I felt his semen squirting down my throat! He shot such a heavy load, I could actually feel it starting to fill my stomach. My orgasm continued, and I felt like my whole body was exploding!

    That's all I remember for a while. I must have passed out from exhaustion after having two mind-blowing orgasms so close together.

    I woke up a good five hours later still on the floor, with a blanket covering me and a pillow under my head. The lights were much dimmer, and my clothes were folded now instead of just laying where I dropped them. Roxy was on the couch, sound asleep.

    I quietly got dressed and slipped out. As I walked back towards the bar to get to my car, I admired the sky—sunrise was still a half-hour away, but the sky was getting deep blue already, and the horizon where the sun would rise was glowing brilliantly in orange, pink and magenta. I was feeling a strange sense of giddiness, like I'd discovered an entirely new world, ready for me to explore—but at the same time, I was filled with doubt. I'd never thought of myself as gay or bi before, but I just had the best sex of my life by far, and it was with a man. I shook it off and decided it was just a fluke. I decided that come Saturday, I'd find a new woman, a real woman, and get my head back on straight. On some subtle level way down inside, I felt relieved, yet disappointed.

    When I got back to where my car was parked, I reached into my pocket for my keys and pulled out my keys and a piece of folded paper. I opened the paper and read the note in the pre-dawn twilight. It said,


    I hope you had as good a time last night as I did. It was the first time I've ever been a guy's first gay experience, and that made our night together extra special.

    You might be feeling confused or ashamed now, Troy. I assure you, there's no reason for that. Just as the world isn't black and white, people aren't either gay or straight. Every person is many things, and each person is capable of feeling anything that any other person can feel.

    I'm a sound sleeper, so I probably won't be up to see you off to work. Call me if you like, there's still a lot more things you have to try, if you're willing. You're a sweet guy and a wonderful lover. I hope you have a great day, and if you choose not to see me again, I wish you a wonderful life.

    It was signed:

    John "Roxy" Rockselle.

    Below the signature, it said,

    P.S., I TOLD YOU SO!!!

    There was his phone number, written right after the P.S.

    Why the hell did he have to add that P.S.?? What a smartass! Feeling like waking him up and giving him a piece of my mind, I pulled out my cell phone and flipped it open. I stood there for a half minute, feeling angry, confused and frustrated.

    Then I had a sudden realization, and all the negative feelings vanished. Roxy was right. Labels like "gay" and "straight" might be useful sometimes, but the labels don't make us who we are. People, like life, are ever-changing. I'd just met a wonderful person who liked me too, and we were in the beginning of what would probably be a wonderful relationship. I saw how ridiculous to let some label bother me to the point of not seeing him again. Judging by the note, Roxy was a caring and concerned friend in addition to being a great lover.

    Several seconds later, I flipped the phone closed and stuck it in my pocket along with Roxy's note.

    On my way to work, I was smiling. I knew what I was planning on doing after work. When I had my cell phone out, I'd put Roxy on speed dial.

    You'd be surprised how much it costs to look this cheap!

    --Dolly Parton

  2. #2
    5 Star Poster TJ347's Avatar
    Join Date
    Apr 2007


    Great story, J! The only way I could see it being any better would be if it was a true story... No chance of that, is there?

    "We are irritated by rascals, intolerant of fools, and prepared to love the rest. But where are they?"- Mignon McLaughlin

  3. #3


    Quote Originally Posted by TJ347
    Great story, J! The only way I could see it being any better would be if it was a true story... No chance of that, is there?
    I wish!

  4. #4
    Junior Poster
    Join Date
    Jun 2007


    Great story indeed many thanks I like your style!
    I'd like a 2nd part with Roxy seducing and finally fucking Troy with his/her huge hard cock
    Roxy shows him her hard throbbing cock sexily bulging under her nylon pantyhose, asking to lick it though the sheer fabric. He then could go on his knees and start to smell and lick her nyloned feet, savouring their sweaty pungent taste while her cock is getting hard as a rock and two times his size!
    She'll put one, two, three fingers into his still virgin anus, preparing him to receive her big tool deep inside.
    She teaches him how to give her pleasure licking her huge cock and hairless taurine balls, filled with hot creamy sperm. She rips her pantyhose on her crotch just to make him have her cock with her nylons on. Troy will receive the first cock of his life, and a very big one!
    These are some suggestions for the next part of your beautiful story, just in case you decide to write it!
    Thanks again and have a great day!

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