tagTranssexuals & CrossdressersAn Uncommon Summer Romance

An Uncommon Summer Romance


It was my second-to-last week of summer vacation. I was lying on my back, legs wrapped around my hot new girlfriend’s slim hips. She was thrusting frantically in and out of me, her nipples thick pencil erasers grazing erotically against my chest. My breath was coming in spasms. My own cock was fairly dripping with pre-cum and saliva. Our tongues twisted together in a slippery, passionate embrace, slithering in and out in time with her frenzied thrusts. Her well-lubricated cock was thick and slightly longer than mine. I could wrap my fingers around it, but just barely. I was in heaven. I was so close. And then she…but wait: “My girlfriend’s thick, well-lubricated cock?” Yes, you read that correctly. The details actually have the makings of a rather interesting story. A romance, believe it or not. It all started with my bicycle.

I like to ride my bike, especially during the warm summer months. There is a paved multi-use trail near where I live that meanders through the woods. Not too many people know about the trail but those that do come there regularly. There are bikers, joggers, and the occasional little old lady walking her toy poodle all happily enjoying nature. I had been riding this trail pretty much every day on those afternoons when the weather was nice.

One gorgeous early summer day at the end of my ride I spied a jogger coming towards me. She was quite pretty. I remember her medium length blond hair was tied back in a pony tail. Loose stands of hair framed her delicate face which seemed to almost glow in the soft sunlight. She was wearing a pair of short blue cutoffs that nicely showed off her trim legs. She had a thin white halter top sort of like a bandana tied behind her neck. She had distinctly lovely breasts.

I rode past her slowly and turned around to look over my shoulder. Her bare back was V-shaped like a swimmer’s, and tanned. Her ass under those brief cutoffs was phenomenal. Tight and high. Defined. I rode on and managed to close my hanging jaw before someone noticed.

In the coming weeks we passed each other frequently. We started smiling at each other in recognition. She seemed to get prettier every time I saw her. Once she waved at me and I remember feeling so good: brilliant, really. I waved back. It seemed inevitable that one day we would meet.

It was exactly one week later that I was finishing my ride and noticed her sitting on one of the benches that bordered the trail. It was quite warm out and she was wearing a short, scoop-necked dress of some flowery print material. On her feet were a pair of leather sandals. I coasted up and leaned my bike against a tree.

“Hi. Mind if I sit down?” “Please,” she said and gestured to the spot next to her. “My name is Cheryl. You know, I’ve been kind of looking forward to seeing you ride by. You have an air about you, kind of intense but friendly. A couple of years ago I realized that I possessed what you might call a “friend sense.” I can almost always tell if I will like someone or not, just by looking at them. You seem to be a person I might like to get to know. What’s your name?”

“Mark,” I answered. “Are you serious? A friend sense? I’ve never heard of anything like that before.” “Well, it seems to work for me,” she said. “Are you from around here?” I asked. “No,” she answered. “I moved here from Washington a couple of months ago. I spent two years there studying at the University, but for various reasons decided to leave. I’m transferring into the University here in the fall.” Interesting, I thought to myself. That would make her a junior. I had been going to the same University for the last two years. I would be a junior too.

“What are you studying?” I asked. “Engineering,” she said. “I’m one of those math/science geeks.” I smiled. I flashed onto a website I had seen recently, something about Geeks Are Sexy featuring a picture of a pretty girl in heels sitting at a laptop. I am a math/science geek myself. I began to look closer at Cheryl. She returned my gaze.

“What?” I asked. “I don’t know,” she answered. “It’s just that…I have this feeling about you. I almost feel that I know you somehow, that I can trust you.” My mind was boggling. This beautiful girl that I had just met was telling me she knew me, trusted me. I didn’t know quite what to say. And I was late for a lesson: I tutored math during the summer. So I said the first thing that crossed my mind: “Look, Cheryl, I’d like to get to know you too but the sad fact is I have to be at my job in about ten minutes. Maybe I can call you?” She looked a little flustered but she said yes. We exchanged phone numbers.

For the rest of that summer we ran into each other on the bike path almost daily. We shared a couple of really nice picnics on the beach and a fairly romantic dinner one bright moonlit night that ended at the doorway of her apartment with a chaste kiss. We talked a lot, both in person and on the phone. We seemed to have a lot in common. It was those phone conversations that really got to me, though. She had this soft, slightly husky voice that made me feel as if she were running her tongue around and into my ear. She gave very good phone. I was wondering what else she gave good. I hoped soon to find out.

One late afternoon a couple of weeks before school was to start we were sitting on our bench, talking and holding hands, when she gently reached across the space separating us and stroked the side of my face. She pulled me towards her and closed her eyes. She gently kissed me on the lips. Her lips felt like silk over bare skin: cool, soft, erotic. She opened her mouth slightly and I felt her tongue flick lightly over my own. I kissed her back. I began to explore her mouth, gently biting and then kissing her luscious lips. We must have kissed for a good five minutes. My heart was pounding and what I felt was pure, unadulterated joy. She pulled back slightly. And looked at me with a degree of seriousness I hadn’t seen in her before.

“You know, I find I am really beginning to like you Mark, so I am going to come clean with you.” She turned to face me on the bench. There was a soft breeze blowing and her hair was moving gently with it. Her skin was bright and clear. She looked like an angel. “Do you remember me telling you when we first met that I thought you were a person I could trust?” “Of course,” I said. “Well, now I’m going to tell you something. And you may not be ready for it,” she said. “It has to do with why I left my university in Washington.”

“You don’t have to tell me anything you don’t want to,” I said, wondering what was coming.

“Well, I do want to. And at this point I think I need to. I left because I couldn’t stand it there anymore. Everyone seemed to be turning against me. I couldn’t be with my friends; I mean, I thought they were my friends, but it turned out not. They behaved cruelly to me. You see,” and here she hesitated, her bright green eyes focused on mine. “I’m not exactly the person you think I am.” Now I was curious and a bit apprehensive. “Who are you then?”

“My name is not really Cheryl. I mean, it is now but it didn’t used to be. Three years ago, before I started college, I began a series of procedures. Hormonal and surgical procedures.” My ears pricked up. I wondered where this was heading.

“My high school friends called me Scott.”

“Scott,” I repeated dumbly.

“Yeah. Scott,” she said. “You see, I didn’t used to look like this. I had a muscular chest. I was a pretty good swimmer. Then I began the treatments. Mark, this is what you have to understand: for as long as I can remember, since I was five or so, I wanted to be a girl. I must have been born that way. When I reached puberty I looked at boys the way other boys looked at girls. But I wasn’t gay. I knew what I wanted: to change my sex. I saw some specialists and I went through counseling. I was recommended a series of treatments; I am still going through with them.”

“My body started changing. I began developing breasts. I liked it! But my friends and family couldn’t handle it. They began to look at me differently. I think they liked me for who they wanted me to be not for who I actually was, who I was becoming. There was no emotional support whatsoever. I couldn’t take it anymore. So I left. Here, I am a new person in a new school. I can be Cheryl and nobody will ever know differently. Except, now, for you.”

“So you’re a…a guy?” I asked.

“No. I mean, yes. No! I’m definitely a girl. Though there is one part of the treatment I am really reluctant to undertake,” she said. “I want to keep my penis. I know this is kind of unusual but it is a part of my body that I’ve always felt comfortable with.”

Now it was my turn to look serious. Here was this girl and I couldn’t at this point not think of her as a girl after the wonderful summer we had spent together, who obviously liked me. A lot. Liked me enough to trust me with something truly intimate and potentially very damaging should I react badly. What a revelation, though! Did this change anything? I looked at her closely. Still the same Cheryl. Pretty. Beautiful, even. Her nipples were just visible through her thin white T-shirt. She looked vulnerable. But not scared. Just waiting for my reaction.

I thought about it. I considered myself a fairly open minded sort of guy. I had just kissed her! And it had felt great. Not just the erotic softness of her lips on mine, but inside me, like a bright light shining. I really liked her too. I had to admit it. Of course I had thought about having sex with her; I mean, who wouldn’t have? She was very sexy. What would it be like though, having sex with a…guy? Could I do that? A hard cock instead of a tight pussy? There had been times in the past when I had fantasized about that sort of thing but nothing ever came of it. I knew I wasn’t gay. But Cheryl was a girl. And it occurred to me that I just might be falling in love. Was her revelation enough to change how I felt about her?

I thought some more. I needed to make a decision. She was waiting. I took a deep breath.

“Cheryl.” She sat up, straightened her shoulders and looked at me. “I really like you too. When we kissed just now—that was phenomenal. I felt it in my bones.” I took another deep breath. “Nothing has changed. You are Cheryl, not Scott. I find you so incredibly beautiful and I really enjoy spending time with you. As far as I’m concerned you’re a girl. You were right to tell me when you did. And I think I understand.”

“And it doesn’t bother you that I have a, you know, a penis?” she asked. “No,” I said. “It’s OK. Really. Besides, who knows? It just may add a bit of spice…” Cheryl looked at me, her eyes widening. She moved closer and took my hands. She placed one of them against her breast and the other on her cheek. She pulled me towards her. And then kissed me again. Her tongue darted in and out of my mouth and I gently caressed her nipple through the sheer material. She gasped. Then I noticed: she had a raging hard on. Cheryl looked down. She smiled.

It was at that point that things began to get hot. We walked over to her apartment which, fortunately, was only a few blocks away. We went inside. She offered me something to drink. “I’m a bit nervous,” she said. “I imagine you might be somewhat nervous yourself!” She made a couple of stiff vodka tonics and we drank them while we kissed and slowly undressed each other. Our inhibitions began to melt away.

She pulled her T-shirt over her head and tossed it over a chair. She wasn’t wearing a bra and her breasts stood out proudly from her chest, her large areolas a deep chocolaty brown. Her nipples were hard and supple, pointing slightly up. I took off my shirt. We kissed some more, our tongues swirling around in each other’s mouths, and I gently twirled her stiff nipples between my thumb and fingers. She moved her hands from behind my head which she had been holding as we kissed, and down to my chest. She brushed her fingertips across my nipples, which are quite sensitive. I loved to have a warm, wet tongue flick my nipples. It sends lightening waves of pleasure down my spine.

Looking into my eyes, but without saying a word, she took my hand and led me upstairs to her bedroom and a large king sized bed. Covering it was a pale green sheet. There were two bright yellow pillows propped against the wooden headboard. We sat down. A large, open window looked out onto the garden. Dappled sunlight filtered into the room and onto the bed. We lay down on our sides facing each other, kissing. We still had our shorts on. We continued exploring each other’s mouths but I was dying to caress her breasts and suck on her nipples.

I lifted myself up and turned around onto my other side, still facing her, but with my feet now pointing toward the head of the bed. I scooted down until I could reach her breasts with my lips. Of course, now my own little buds were lined up with Cheryl’s mouth as well! We used our tongues and our fingers to flick and stimulate each other’s nipples. I knew by her reaction that the electric feelings coursing through her body were identical to those flowing through mine.

Her wonderful tongue still flicking my nipples I felt her hand beginning to rub against my stomach, circling, caressing, moving lower. Soon I felt her fingernails slowly scratching up and down my engorged shaft through my shorts. I couldn’t stand it any more. I reached down and slipped them off. I was completely naked now. I returned to sucking and licking Cheryl’s nipples and Cheryl, with nothing to hinder her any more, wrapped her hand around me and began slowly to stroke. I spread my legs to give her access to my balls which she soon took advantage of, caressing and gently scratching them while I moaned softly.

She moved further down the bed. My face was now a scant two inches from the thin material of her shorts. I could detect a distinct bulge there. She took me into her mouth. Oh my god! Nothing had ever felt so good. She ran her fingernails lightly across my balls with one hand and slowly licked my cock head, moving her tongue around and around. She flicked her tongue behind the rim, that almost painfully sensitive ridge at the back of a guy’s cock, knowing exactly the sensations I would feel there. She alternated her hand between scratching my balls and stroking my shaft, bringing me almost to orgasm but then pulling back, seeming to just know when to ease off.

My inhibitions had by now completely vanished. I slipped my fingers through the waistband of Cheryl’s shorts and slipped them off. And there, staring me in the face was the biggest cock I had ever seen. Of course, I had never actually seen a real cock up close before other than my own, but it seemed huge. Maybe seven inches long and well over one and a half inches thick, it was leaking pre-cum. There were small veins running the length of it. The head was slightly purple and a bit thicker than the shaft. I now understood completely why she had wanted to keep this treasure! Her balls were tight inside her sack. She had a neatly trimmed thatch of soft blond pubic hair. My lust was pounding in my head.

I touched my tongue to her. I tasted her pre-cum. It was slightly salty and a bit sweet. I stuck out my tongue some more and licked the silky underside of her cock. Cheryl moaned. I imagined what it would be like putting whole thing in my mouth…I licked slowly down her shaft all the way to her balls. I took one into my mouth and caressed it with my tongue. Then I switched to the other. Cheryl was doing much the same thing to me. It felt too good to be true. I licked my way back up her hard shaft until I got to the head. I opened my mouth and slowly sucked it in.

It was so smooth. I worked my lips up over her head lubricating it with my saliva until the whole thing was in my mouth. I began to move lower, slowly, and then back up until just the tip rested against my tongue. I did it again, going farther down this time and then back up. Maybe I actually could fit the whole thing in…I tried again, moving down even farther. Her cock was getting slippery. I held her balls in one hand while I moved up and down on her shaft. After a while I felt the first wisps of her soft blond pubes against my face. I had done it!

Cheryl, meanwhile, had my own dick deep in her mouth. We sucked each other’s slippery cocks our heads moving like slow pistons up and down, in and out. I closed my eyes to better appreciate everything I was feeling and experiencing. She even smelled good: fresh, like late afternoon sun on warm grass.

After a while Cheryl moved her head back. I slipped out of her mouth with a soft plop. “I want to try something,” she whispered. She pulled me over and on top of her in a kind of reverse sixty-nine position. My legs straddled her head, my balls hovering just under her nose. Her hard dick jutted at an angle over her flat stomach. I brought myself up onto my elbows and gently eased her cock back into my mouth. Cheryl started licking my balls. I could feel them tightening but as my cock was now pretty much out of reach of her mouth I knew I wouldn’t be coming just yet. I was getting close, though.

Cheryl continued licking and sucking on my balls. She moved herself lower, her tongue now slithering over my perineum. No one had ever done that to me before and it felt kind of naughty, but really good. She ran her nails over the backs of my thighs and up and over my buttocks, massaging them. I began to get goose bumps! Then she tightly twined her fingers over my lower back, pulling me down firmly against her.

Suddenly, without warning I felt an intense, shattering sensation arising from Cheryl’s skittering tongue work. My whole body was electrified. I tried to lift my hips, to pull away it was so intense, but I couldn’t. Cheryl was holding me too tightly. She had deftly thrust her slippery, rolled up tongue deep into my ass! The feeling was indescribable: the softness, the wetness, the invasion of that so intimate part of me. She pulled out and impaled me again. I shuddered with the intensity and the ecstasy and still I couldn’t pull away. There were nerve endings down there that I hadn’t even known existed. Again and again she thrust her tongue inside of me: slowly, deeply, and with enough force to make me moan with desire.

It wasn’t too long, sitting on her slippery tongue, before I became somewhat used to the feeling. Cheryl unlaced her fingers and returned to scraping her nails over the backs of my thighs. Her dick had popped out of my mouth when her tongue had taken me by surprise and I returned to moving my lips up and down her shaft. Soon she began to buck her hips, meeting me halfway.

At that point Cheryl’s tongue pulled away from my asshole. I felt deprived. She moved down the bed a little farther, kissing and nibbling the insides of my thighs as she went. She slid out from under me. I was still on my elbows and knees facing away from her. “Mark,” she panted from behind me. “God, I’m so horny! I have to tell you: I’ve had this, well, sort of fantasy for the last couple of years. And seeing you like this is making me want to live it. You look so incredibly sexy in this position, with your ass up in the air.” I was panting too. “Tell me what you want,” I said, having a pretty good idea what she was about to suggest. (As I mentioned earlier I had sometimes fantasized about being with another guy, but I had never done anything about it. The idea turned me on in an intellectual kind of way but I was thinking that now might be my chance to actually go through with it. With a girl, yet!)

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