Author: wolfcub Title: Transgender Boy Summary: A cross-dressing boy becomes a little too much like a girl. Keywords: bb exhib tg 1st oral anal My parents are weird. I mean, everyone's parents are weird, but mine are extra, beyond-normal-weirdness, weird. And I'm an only child, so I get more than my fair share of their weirdness. My dad likes showing off my body. When I was a baby, I rarely wore anything more than a diaper. Once I was out of diapers, I became Naked Boy (a nick name my aunt gave me that was used by most of our family and my parents' friends). I rarely wear more than a pair of shorts outside, and I'm always naked at home. Even when my parents' friends--and their children--are visiting, I'm still completely starkers. The kids used to play naked with me, sometimes, but around age 7, they started to keep their clothes on, as do my current friends, when they're over. When I do wear clothes, its usually loose-fitting shorts (really short shorts--not those below-the-knee kind that most boys wear) and a tank top, muscle shirt, or some kind of mesh thing that only technically qualifies as a shirt. My mom's into photography (she's really good at it, too), so the walls of our house are plastered with pictures of me--mostly either completely naked or mostly so. She even posts pictures of me naked on her online photo journal. When I was four years old, my parents decided to go on a vacation to the Caribbean. Their last real vacation had been shortly after my mom got pregnant with me, so they were really looking forward to the trip. Not to let an opportunity to be weird slip by, my mom decided it would be fun if I were to "take a vacation from being a boy." She found a bikini bottom with a frilly skirt in the front to cover the bulge that shouldn't be there. That and a white sundress were my only clothes for the week. I had wavy, blond hair that came down to my shoulders (like I still do, now) so I did a fair job of passing for girl. I was four, so what did I care? My dad was a little disappointed that he couldn't undress me at the beach showers, like he did at home, but I think the fun of showing off his topless "little girl" made up for it. My parents enjoyed the vacation spot so much that they decided to return the next year. At five, I had to be let in on the pretend-to-be-a-girl gig, but Mom made it fun, so I was game. It became an annual event, and I actually enjoyed hanging out with girls, for one week out of the year. At eight, it became a little weirder. Eight-year-old boys don't talk about girls--except the odd comment about how icky they are--so I was surprised to find that that was a primary topic of conversation among my eight-year-old girl playmates. Most of the girls, including me, went topless and wore skimpy, string-bikini bottoms. (Mom had found me one with a frilly little flap in the front to conceal the fact that I was a boy, but otherwise, I was as near-to-naked as my girl companions.) A much-discussed topic was the fact that most of the boys here wore racer or square-cut swimsuits--unlike the ubiquitous board shorts common at home. I learned quite a bit about what girls find attractive about boys (at that age, hair, eyes, smile, and muscular arms and chest were popular with almost no mention of butts or bulges; those came later), and I later made use of that knowledge to attract quite a few girls--once I was old enough to be interested. At ten, the talk turned from attraction to sex. If you've never hung around ten-year-old girls, you may be surprised to learn that they talk about sex--but they do. And marriage. And making babies! The first time I heard a ten-year-old girl say, "He's hot! I'd like to have his baby!" I choked on my fruit punch and almost spit it out. The next big change came at eleven. That's when the boys started showing interest in the girls. The first time an eleven-year-old boy came up to talk to me, I didn't think anything of it--at first. I talked to eleven-year-old boys all the time. It was when I realized he was acting sheepish, and his friends were giggling, that it occurred to me that he was hitting on me (in that awkward, eleven-year-old way)! I had been on the other end of a similar encounter several times, myself, recently, and I felt for the boy. Plus, Mom had always played up the fun aspect of pretending to be a girl, so I decided to play along, not considering the implications of my actions. "Is this your first time here?" the boy had asked, with all the weary of any "Do you come here often?" line. I'm pretty sure my smile came across as a sign that I was tickled to be taking to a boy rather than an indication of my amusement. "No, my parents and I have been coming here every year since I was four. Is this your first time?" (Okay! Being the same age, I'm allowed to use the same, lame lines! Gimme a break!) "Maybe you can show me around!" he said, with rather a lot of hopeful enthusiasm. "This is my first time here." "Maybe," I answered, coyly, sizing him up with my eyes. His strait, light-brown hair came over his ears and almost hung in his eyes, but it didn't reach as far as his shoulders. He had green eyes--like me--and a cute nose. His shoulders where broad, and his chest somewhat muscular--but not overly so. He had a taut belly and long, muscular legs. From the outline on the front of his shiny, blue racer, I could tell his testicles were a little large for a boy his age, and his stiff penis was about average girth and length. I felt my own penis stir and worried that I'd blow my cover if I tented the skirt on my bikini bottoms. "Let's go for a walk!" I said, taking his hand and almost dragging him from his friends. I didn't have any particular destination in mind--I was just avoiding giving him the opportunity to discover my secret. There was lots of giggling behind us--from both boys and girls--but none of either of our friends followed us. When the giggling was out of range, I slowed our pace so that I was no longer dragging my companion. We were nearing the pool area of the hotel where my parents and I were staying, so I led him to the bar and asked, "What some ice cream?" Without waiting for an answer, I hopped up on one of the stools; my friend sat beside me. While watching our sundaes being made, we chatted about nothing. Turns out he was staying with his parents in the same hotel. With our legs dangling from the bar stools, I found myself idly playing with his legs and feet with my own while we talked. When I realized what I had been doing, I saw that he was blushing, and the front of his swimsuit was fully bulging. I blushed, myself, and we were both thankful to be distracted by the arrival of our sundaes. We continued talking while we ate. This time, I intentionally brushed my legs and feet against his. The stools were close enough that I was able to spread my legs and just touch his bare thigh with my own. Seeing the reaction I was getting--and thoroughly enjoying it--I put my hand on his shoulder, leaned into him, and whispered into his ear, "You're cute!" I sat back and enjoyed the embarrassed smile on his face. Next, I swiveled by stool to face his and made a more deliberate effort at massaging his legs with my feet. After a quick look around the bar to see that no one was looking our way, I pressed my foot into his crotch, curled my toes around his stiff penis, and gave a playful shove. He quickly brushed my foot away with one hand and adjusted himself in his swimsuit with the other. Undeterred, I placed a hand on the upper inside of his thigh and gave a gentle squeeze. I teased him, mercilessly, doing all the things I wished a girl would do to me. By the time we had finished our sundaes, I was surprised he hadn't wet himself. I took my new boyfriend by the hand and led him away from the bar, following the path that led to the bungalows. I let go of his hand and slipped my arm around his waist, hugging him towards me as we walked. His body stiffen, at first, but then he quickly relaxed, slipping his own arm around my waist. I noticed a small clearing in the bushes, just off the path. On impulse, I led my boyfriend into the somewhat secluded cranny. I turned toward him, drawing him to me, and pressed my nose against his. We both had huge smiles on our faces. His hands slid down my back and cupped the exposed flesh of my cheeks. I kept my hands on his hips so that I could prevent him from pressing his crotch against mine, as I was certain he'd immediately detect the bulge of erection raging beneath the thin skirt of my bikini. I was surprised when he kissed me on the lips, but I kissed him back. Then, I tentatively pushed my tongue forward. Without objection, he pushed back with his, and we were quickly making out like horny teenagers. His hands were all over my body, but I kept my own securely on his hips to protect my secret. Suddenly, I realized that he was trying to pull my bikini down. I grabbed his wrist and pulled away from him, ending up on my knees. I had heard lots of talk about what girls do for boys. I had often thought about having a girl do those things to me, but I had never considered doing them to another boy; however, I knew that if I didn't do something quickly, this boy was going to push me onto my back and climb on top of me. So, without really any thought, I hooked my fingers into the front of his swimsuit, pulled them down, and caught his springing penis in my mouth. Fortunately, the surprise checked his advance. I finished pulling his swimsuit to his ankles as I sucked vigorously on his penis. I then cupped his buttocks with one hand and fondled his testicles with the other, all the while sucking for all I was worth. After having teased him so viciously, he didn't last long. I was surprised by the quantity and force of his ejaculation. I had just started squirting, myself, a few months ago, but mine was just a few drops of thin, watery fluid. I now had a considerable amount of thick fluid in my mouth. Again, without really thinking about it, I swallowed to keep from choking. A few more, much smaller squirts followed, and I swallowed them, too. It was then that I fully realized what had just happened--and that I had rather enjoyed it! I gave a long, hard draw on his softening penis and let it slip from my mouth. The boy collapsed to his knees and pressed his nose against mine. We were both giddy with laughter and breathing heavily--his exhales timed to my inhales so that we were both breathing the same air. After a minute or so, he asked, softly, "Do you want me to do you?" I was puzzled, at first, then I realized what he meant. I tried to quickly think of a reasonable excuse for saying no, but then we heard the voices of some people approaching along the path. He hurriedly tugged on his swimsuit, and we emerged from the bushes just as two adult couples rounded the curve in the path. They smiled, and nodded a greeting to us, but they were too involved with each other to give us much notice. On the way back to the hotel, we ran into his friends and mine. Both were anxious to hear what had gone on. We clustered in two separate groups, and while the girls peppered me with questions, I could tell from the reactions from his friends that the boy wasn't holding back any details. "So, what's his name? You don't even know his name? Damn, girl!" That night at dinner, I slipped out to the pool while my parents were dancing and ran into the boy. I was, as usual, wearing only a sundress; the boy was wearing khaki shorts and a light-blue polo shirt. Like me, he was barefoot. He walked up to me and shyly said hello. "You know," I said, just as shyly, "We don't even know each other's names! Mine's Jayden." (My real name--which, conveniently, works for both a boy and a girl.) "I'm Josh." He smiled when I placed my foot on top of his. "Are you going to the dance, tonight?" I asked. "What dance?" "There's always night-time activities for kids and teenagers--so the parents can have some alone time." I cringed at my unplanned use of my parents' corny, embarrassing phrase. "I'll have to ask my parents." "Cool! Where are they?" He led me to the opposite side of the dining room from where my parents and I were seated. His parents were considerably younger than mine. They immediately noticed that I was holding their son's hand--and they seemed quite pleased about it. They gave their consent without hesitation. My own parents gave me their "Are you sure you want to do this?" look; I replied with my best, "This whole thing is your fault" scowl, then Josh and I were on our way. This dance was for the eight- to twelve-year-olds, so there wasn't as much dancing as there was standing close to each other and shuffling. The hotel chaperones saw to it that the boys and girls didn't congregate on opposite sides of the hall for too long. Josh and I were soon shuffling together with our hands on each other, but the presence of so many other kids kept them from roaming around--too much. If I had had a pair of panties, I would have worn them that night, as I was deathly afraid of tenting out my dress; however, even at eleven, I had a scant two inches stiff, so it turned out it wasn't a problem. Josh had no problem tenting his shorts with his beautiful four inches. Did I say beautiful? Maybe playing the part of a girl makes me think like one, but I didn't just think his penis was beautiful. He was beautiful! And I was proud to be dancing with him in front of so many other boys and girls. Of course we ran into my girl friends--all the girls always went to all the dances--but we didn't run into any of the boys Josh had been hanging with earlier that day. There were enough boys so that my friends found dance partners without cutting in on me and Josh--which they sorely wanted to do and which I wouldn't allow. "You're so lucky!", my friend Sierra gushed, after dragging me away from Josh to get some punch. "So, are you going to do more with him besides what you've already done?" "Sierra!" "Don't, 'Sierra!' me! I'm not the one who sucked off a guy I just met! I figured, if you moved that fast, you'd be spreading your legs for him, tonight." "Don't!" I said, with my best girl-squeal, which I could do now without even trying. "My parents are on that moonlight cruise," Sierra rolled her eyes as she said it, "So I'm hanging with Katelyn and her parents, tonight. I could give you my room key." "Sierra! Stop!" Just then, Josh came over to get some punch, himself, rescuing me from further torment from Sierra, but leaving me with the same predicament. Josh talked me into going for a walk, and we easily slipped the hotel chaperones. "So," Josh said, with some hesitation, "Do you wanna come up to my room!" "And do what?", I asked, suspiciously. "You know! We could, like, make out again--and maybe you could..." I actually blushed, remembering what I had done. "Are you sure you don't want to do something else?" I asked, with a sinister grin. Josh's eyes widened. "Okay! I just thought you wouldn't want to--so quickly. You know?" His sudden enthusiasm made me laugh!" "Slow down, stud puppy!" My mom had started calling me that after she found out I was getting interested in girls. "I'm not gonna do that with you." "Oh." The dejection in his voice made me sorry I had said it, but there was no way that would end other than badly. Still, my devious smile returned, and I added, "Yet," which brought the smile back to Josh's face. So, over the next few days, I managed to make out with Josh--quite a lot--and give him a few more blow jobs--greedily swallowing each time--without letting him gain access to the parts between my legs that would ruin our little pre-teen affair. On one level, I felt kind of bad about what I was doing. Josh was quite the looker, and it was clear that he could have gotten a real girl--maybe even one that would let him do the thing that boys liked to do with girls--if he wasn't preoccupied with me, thinking I was that girl. On the other hand, Josh was my first love. I realized that very early on. I was actually in love with him--in that pre-teen, puppy-love kind of way. I began wishing I could tell him my secret--and that he'd still like me after finding out. "Dad?" I began, two nights before we were leaving, lying naked on my back on the bed in our hotel room with my penis sticking straight up toward the ceiling. "How can I make Josh like me." "I think he already likes you," my dad answered. "No, I mean as a boy. He likes me as a girl." "After the way you two have been carrying on, I don't think Josh would recover from finding out you're not a girl. It's best just to let him go home thinking he had a good time with a beautiful girl on vacation." "He wants to have sex with me." "A lot of people want to have sex with you." I sat up. "What do you mean by that?" "Nothing. You know what having sex with a boy means. I don't think that's what Josh is looking for." I crossed my legs and idly stroked my penis. My parents have no qualms about boys playing with themselves--and my mom has plenty of pictures of me doing it from infancy onwards to prove it. "Maybe he doesn't, but he'd like it anyway." "Jayden," my dad said, tenderly, putting an arm around me, "I'm pretty sure if you tell Josh the truth, he'll get mad and probably say a lot a mean things to you. I don't think you want to risk that, do you? It's better if you go home with good memories of Josh." I sighed and stopped stroking my penis, which was beginning to deflate. My dad, who's usually good at figuring things out, came up with a solution for me that brought a smile back to my face. The next day, Josh and I were sharing a lounge chair on the beach in the shade of an umbrella when I put my dad's plan into action. "Josh, have you ever fooled around with a boy?" Josh stiffened up and got all nervous. "What?" "My girl friends and I--back home--fool around, sometimes. You know, practice kissing--stuff like that. I was wondering if boys do the same thing. My friend Emma says she caught her younger brother fooling around with his best friend, but he denies it." "Um..." Josh's attitude made me suspect that the answer was yes, which was exactly what I was hoping for. "I...uh..." "It's okay if you do! I don't mind. I'm just curious." "Well, once--at a sleepover with my best--he and I sort of..." "Sort of what?" "Do we have to talk about this?" "No, but I'd like to talk about it. Did he suck you, like I do?" Josh's face turned bright red, so I knew that he had. "And did you suck him?" I wouldn't have thought it was possible, but Josh's face got even brighter. "You did, didn't you? That's okay. I think it's cool to think of two boys sucking each other." "You do?" Josh asked, a little relieved. "Sure? Don't you? Otherwise, you wouldn't have done it. Did you do it more than just that once?" Josh was squirming, again, so I knew he had. "How often?" Josh was getting more uncomfortable. "You do it all the time, don't you?" Josh looked like he was about to cry, so I leaned forward and kissed him on the lips. I pulled away to see that my kiss had cheered him, a little, so I leaned in and kissed him, again. "Have you done anything else with him?" "Like what?" "Like the thing that boys do to each other that's like sex?" "No," Josh answered, quietly, and with disappointment in his voice, "He didn't want to do that." "Did you want to do that?" "Kind of." "Kind of?" "Okay, I did want to, but there's nothing wrong with pre-pubescent boys doing that with each other. It's just experimenting." He stumbled over "pre-pubescent" and said the whole thing like he was repeating something an adult had told him. I kissed him on the lips, again, took his hand, and led him to my hotel room, which my parents had promised to stay away from for the afternoon. The door closed behind us. I stood in front of Josh and ceremoniously pulled on the ties holding my bikini bottom on. I let it fall to the ground. Josh's eyes widened, but he didn't run away screaming. I put a finger to my lips, then walked over to the nightstand and took out the jar my dad had left for me. I scooped out two fingers full of the cream, then pushed the fingers into my butt hole. I climbed onto the bed on all fours, looked over my shoulder at Josh, and wiggled my butt at him. Nothing happened for two full seconds, then Josh almost fell over tugging his swimsuit down. He pounced on the bed, wrapped one arm around my waist, and used his free hand to position the head of his stiff penis at my hole. It hurt when he pushed in. He didn't go slow or in any other why try to be gentle. He was so anxious to avail himself of this opportunity that he just rammed his penis into me and started thrusting like a rabbit. Even though it was painful, I liked having him inside me. I wanted to tell him to slow down, but he was lost in the excitement of the moment. Fortunately, he didn't last long. In less than a minute, he pushed hard into me and grunted. I felt his penis twitch several times, and I knew he was pumping his semen into my butt. Eventually, he collapsed on top of me, but I was able to support his weight. It wasn't long before his penis softened, and he slipped out of me, at which time he rolled onto his back and laughed out loud. I laid on my side next to him to avoid making a mess on the bed. I cuddled close to him and kissed him on the cheek. When Josh had recovered, we did it again. This time--at my insistence--he went more slowly and gently. It was wonderful feeling him inside me! This time, it didn't hurt so much, and I was able to enjoy his stiff rod pistonning in my bowels. I loved the feeling of them opening up to receive his penis then collapsing behind it as he withdrew. The next day, we put on the pretense of boyfriend/girlfriend for our friends--except that Josh was even more attentive to me than he had been all week. We were able to sneak away so he could fuck me twice more before I left with my parents the following day. Sitting in the airport wearing my sundress, I caught the eye of a cute boy with red hair. He, his younger sister, and his parents boarded the plane with my parents and me. He looked about twelve and his sister maybe ten years old. I smiled while imaging a way to be with both of them. ----- If you enjoyed this story (or any of my other stories), I would appreciate a quick comment. Thanks! https://secure.asstr.org/cgi-bin/ah_feedback.cgi?id=KYKADDHQSDHAFCAVRWRM