Jaycee

by vickie tern

I made my first really intimate girlfriend just before my last year in High School, the summer I was nearly seventeen. Strictly speaking, his mother had already shaped him out, but I put on the finishing touches, so I guess you can say we both made him my girlfriend.
When I finished with him he loved what I'd done, and we've been good friends ever since, though since we went away to different colleges we've hardly seen each other, only when I'm home on vacation and he is too. He's still a girl and will be for life, but with a difference. But I'm getting ahead of myself.

When I began with him he thought he was a boy and wanted to live like one, and I could understand that. I'd wanted to be a boy too until I hit puberty and my body began to round out and smooth over, and my tits ripened, and I realized I had no choice. Then I discovered it's much better to be a girl. Marianne, the boy I'm talking about, he never had any choice either, not really, but he didn't know that till later.

I better explain all this. When I was little I hated wearing frilly dresses and ribbons whenever we went visiting, and sitting up straight with my Mary Janes dangling off the floor, and listening to the grownups talk, and always being neat and ladylike. My boy cousins could stretch out all over the floor and wear torn jeans and boy-size work boots, and pick their noses, and make disgusting noises all they wanted. Or they could go out and climb trees, or throw footballs, but I always had to be a lady, even when I was still a little girl. It wasn't fair, just because I happened to be born a girl. I really envied them. So whenever I could I wore jeans and boots and learned how to swallow air and belch the same as them. Anything they did, I decided I was going to do too, better! And I did, too!

My mom despaired, though she never gave up on me. She'd ask me over and over, "JayCee, why don't you play with dolls like all the other girls. There are such pretty dolls these days, and whole wardrobes for them, and even makeup."

I'd answer, "Because I'd rather play with boys, Mom." She never could figure out how to answer that, so mostly she'd leave me alone then until the next time.

In fact I was quicker than most boys, and smarter, and tougher, and more stubborn, and I never refused a dare dodging traffic or climbing trees. But when we crossed into our teens all the boys began to develop deep chests and shoulder muscles, and got so they could swing on branches like apes. Not me. With my thin arms I could only hang there and then let go. They got bulkier and stronger and I only got softer and rounder, a lot softer and rounder on my chest. So I had to quit trying to compete with them. I bought a bra and took up being a girl as a life sentence.

That pleased my folks, who'd never thought it would happen. Especially my mom was delighted when she found she had a daughter to shop for after all. Then once I got some girl clothes and started wearing them, and got a girl's hairdo, and started wearing a little makeup, wow, I found out that for my whole life I'd been absolutely wrong! Talk about dumb? What I found out was that no way did I ever have to prove I was as good as a boy. I found out that girls never have to prove anything. They're already better than boys in every way that matters. And I found that deep down, boys already know this. Girls don't ever have to do anything boys do because they can always get boys to do it for them. A girl can make a boy stumble all over his own feet and fall on his face if she feels like it, no problem. Girls can even hurt boys real bad, and if they do it just right the boys'll never complain -- in fact they'll say thank you. They can't help it. That's how they're made.

Even my boy cousins couldn't help themselves, I realized. One day when we were still thirteen or so two of them were showing off in trees in their back yard, and one of them paraded right off the end of a branch while looking over his shoulder to see if I was watching. He broke his collar bone when he hit the ground, but when his parents hustled him off to the hospital he was still looking back to see if I'd seen it happen! It's obvious. Boys want to please girls. They need to. The only choice they get, maybe, is which girl especially. They'll do anything we say, if we know how to say it just the right way. And that's how it is.
I guess I was still fourteen when I first found out how far I could push a boy, and how much fun it was. Our house has a swimming pool in the back yard. The previous owner used it just to look at, but our family uses it all the time, and so do a few of my friends from time to time, when I invite them over.

Well, one day when it was hot and my folks were out, two boys I knew from school came by, a year or two older than me. They hoped I'd ask them to hang around and use the pool, and I figured why not -- they were both cute. They weren't the smartest boys around, but still, good enough for me to practice being a girl on them. Ronnie, the tall one, he was into body building, and his shoulders and legs showed some promising bulges even then. Petey was short and thin and not too hard to fake out -- I once beat him at Indian wrestling because he went for a sucker shift-of-weight, and then he fell for the same move a second time too. It bothered him, my faking him out, because I was only a girl. He kept asking me how I did it, and did I knew any other tricks. I told him lots, but that only girls can get away with using them. That didn't stop him, so I told him a few. Maybe he's still trying them out.

Anyhow, they were sweaty, and it was hot, so I told them sure, we'd all use the pool. Then it turned out they already had their bathing suits and towels with them. That annoyed me, because it meant they were pretty sure I'd invite them to stay, and I don't like anybody to feel pretty sure of anything when they're around me. But I let them think they were right as we splashed each other, and laughed, and they tried to grope me, and I swam circles around them.

Then came time for them to change back into their clothes. We were all three sitting around a big poolside patio table, and I suggested we play a game. They glanced at each other. Petey wagged his head at Ronnie, and Ronnie nodded, and then they both grinned at me, and then there was a pause. They had a plan. I tried to keep a straight face.

Then Petey asked me if I'd like to play "Show and Tell" with them. The way we play is, each person gets to ask the others to show or tell about something personal or embarrassing, or to do something like that. All the players then have to do that same thing, even the person doing the asking. That's so no one will ask for anything too far off the wall.

Well, what they'd want me to do was obvious enough. I mean, did I have to put on a red riding hood and take a walk through the woods to figure that one out? But I got this idea I wanted to try, so I said "Sure."

They stole another quick look at each other, and Ronnie, he said, "You're sure, now," and I said sharply, "I just said so, didn't I?" I wanted to get on with it. Then a quick thought: "You guys too, no chickening out by anyone! And there's two of you, and you each get to ask one thing, but there's only one of me, so to even it out I get to ask two things of you guys, right? That's only fair." Then I added, "You first, I'll go last."

Well, they were so eager to play they didn't think through whether that was fair or not. I'd be getting two of whatever I asked for each time, one from each of them each time, four all in all. But they'd get only one thing from me apiece. So my taking two turns wasn't really fair. But they were thinking it was themselves versus me, two boys versus one girl, not each of us versus each other, so they couldn't add up two and two, so they just nodded without thinking. In a way they got what they deserved.

We sat around the big table and just looked at each other, until finally Ronnie lost it and started to leer, and he said right on schedule, "Me first. Ok. Stand up and show us your boobs, JayCee. Naked."

Well, I was wearing a two piece bikini, and I still didn't have much to show when I was fourteen. My nipples were large and pointy, but I was only beginning to swell out. Still, given what I had in mind for them, I had no problem exposing my tits. I sort of took center stage and started to untie my halter in back. Then just to make sure there'd be no misunderstandings, not now, not for the rest of the game, I paused still holding my string ties together and said, "You too, Ronnie. You too, Petey."

They looked at me as if I'd gone weird, because they were both already bare chested. But finally they both stood up, and waited, and then Ronnie thought to say, "Ok, that's how we are."

So I nodded and undid the rest of my bathing suit top, and then held it out to the side at arm's length, and stood there with my other hand on my hip. Their eyes followed the top as I held it out, then shifted back to my exposed nipples and the slightly round mounds behind them. They stared at me solemnly for a while, and made whatever they could of what they saw.

Then Pete said, "OK, now my turn. Show us your pussy, JayCee. Take off your bathing suit bottom." He paused, then added, "You promised, remember?"

Talk about unsure? He didn't think I'd do it, so he fired off his reserve argument right off. But he didn't need to worry. "No chickening out, that's what we said," I said. I untied the two side bows on my Bikini bottom. Then I paused and waited. "You too," I said.

Well, they'd been so eager to see what was between my legs they forgot they'd have to drop their pants too, but they hesitated only a moment. A little embarrassed but with his eyes on the prize, me, Ronnie pushed his bathing suit down to his knees, took a deep breath, and stood up. Then Pete. It was sort of funny. They both tried to stand up straight like me, shoulders back and chest out and all, but they hunched over anyhow, as if they could hide their private parts behind their bellies, and they finished in a kind of half-crouch. It was pathetic. I let go the strings on my bikini bottom and then pulled it off straight out from between my legs. Petey gasped! Then I held the bottom to one side too, with my other hand.

Now there I was, standing before them completely naked, arms out, shoulders back, head high, looking straight into their eyes. Not that I didn't want to check out the scene further down on them. But in due time. I knew that now, for what I meant to do, they had to know who was in charge. And it was odd. I didn't feel any way exposed or vulnerable or immodest, or even naked. In fact the reverse. It was as if I were fully dressed, only in my skin, like those nude women in those paintings over at the museum, those Greek goddesses. As if I were standing in front of a throne.

So I took over. "All the way off," I said. "Put your bathing suits on the table." And I put my bikini top and bottom down on the table to set them an example, and then I stepped back a few steps and put my both hands on my hips, legs a little apart, and I stared at them again, and my bare tits stared at them too. Still embarrassed, they stripped down the rest of the way, then picked up their bathing suits and put them on the table.

Ronnie tried again to pull his shoulders back and stand tall, like me, but when he straightened up his knees bent. Pete was having his own problems. He was trying to cover his whole body with just his hands. "I can't see you," I said to him. "Are you ashamed? Of what?" I leaned back and cocked one hip at them, my pelvis thrust forward, my hands still draped on my hips, and I looked at them sideways amused, like girls I've seen in the movies when they're playing seductive but hard-to-get. Then when I saw what I saw, I *was* amused.

There they were, both of them, naked penises at half-dangle, balls shriveled and trying to hide behind their penises. Pete's prick had a pointed foreskin, but even with the extra flap it hung only maybe half way down his balls. It looked maybe only an inch or so long, soft the way it was. But Ronnie's big purple cock head hung way down below his balls, maybe six inches down altogether, maybe more.

I'd already seen my cousins' equipment the previous Thanksgiving when we were all playing "Show and Tell" together out in back while the grownups watched football inside, so these were no big deal. Ronnie's and Petey's cocks looked just as silly, hanging there between their legs. I hadn't known that cocks could vary that much in size, so that was something, anyhow. And Ronnie's was the biggest I'd seen yet, so that was something else.

Meanwhile, they both stared fascinated at the vee of my crotch, which then was just barely covered with tan fuzz. There was nothing else for them to see, just my fuzzy mound, and maybe the beginning of my pussy, where the flat space disappears into the crease tucked between my legs. But they couldn't take their eyes off it. I suddenly realized that what they were staring at was for them the unthinkable. They saw nothing! Nothing at all. A smooth curved surface unlike anything they'd ever seen between anyone's legs. No cock sprouting out of it, and no balls. Nothing.

I suddenly realized that in some deep place way down inside them, they were awed and a little frightened. Here was the place they'd come from, the same as their mothers', and that was mysterious in itself. But worse! Here was what their own crotches would look like if everything hanging there was cut off, missing, gone. They had cocks and balls, but I had nothing. I had nothing to lose. They were exposed and at risk, and I wasn't. It was as if the worst thing they could imagine happening to them had already happened to me, in some primordial way, yet I wasn't the least bit bothered by it. In fact I was completely at ease, and that made me superior beyond their comprehension. Was that why they instinctively tried to hide themselves, and why I felt so powerful at that moment?

"Now my turn," I said. "I get two things to ask." I looked at their eyes. They were both still staring down at my mystery, silent, coping with their thoughts. "Now, my first show and tell is, show me how you guys masturbate."

They both stiffened, surprised, and raised their eyes up to look at me, and found I was already staring back at them steadily, not even blinking. I sensed in them a sudden tension I could use if I could tip them the right way, so I decided to go for the gold.

"How you masturbate each other, I mean," I said, as if I were completing my original sentence. Then I sat down at the table and waited, never taking my eyes off them, making myself into an audience of one waiting for them to begin their performance.

Well, as I'd expected, there were delaying tactics and denials, a stream of "You're kidding, right?" and flat out "We don't do each other," and "No way, Jose!" and so forth. I gave them a minute to vent and get used to the idea, even to think they'd persuaded me, and then I cut them both off with "No chickening out, remember?" Then I couldn't resist. "Even though those little pricks do look like chicken skin, the necks when the heads are chopped off!"

They flinched, but I kept looking at them steadily. They looked at me a moment longer, then averted their eyes and looked at each other. I had them! Gently, even seductively, I added, "Just reach over, you two, and pick up each other's cocks, and then show me how you do it. Pull very gently. Be nice to each other!"

Then they couldn't resist. It was as if I were doing it to them. They didn't dare look at each other or say anything, but they each edged closer, faces fixed in a sort of smiling grimace, and Ronnie's hand reached out for Petey's little thing. Ronnie groped too high, so Petey took Ronnie's hand, pulled it further down, lifted his cock, and placed it on Ronnie's palm. Then Petey looked at Ron's crotch, reached over, and tenderly cradled Ronnie's long dingus in his whole hand. Better than I'd hoped, I was thinking. They both stood still for a few seconds, each hand getting used to the heft of an unfamiliar penis, each one aware that the other had custody of his most prized possession. Then they each closed their hands on the other's cock and began to pull back and forth, gently. Soon the pricks swelled up to fit their open fists, and then they had no more problems holding and pulling or stroking them. They closed their eyes. Ronnie held the whole of Petey in his hand, now all of four inches, and squeezed it rhythmically, and Petey slid his palm up and down on Ronnie's long monster as it got longer, and they each pulled and stroked, over and over, and a slight smile came over each one's face.

"This doesn't count as my second show and tell," I said. "But wouldn't it be a little more friendly if you looked into each others' eyes?"

They opened their eyes and looked at me and then at each other, a little evasive at first. Then more directly at each others' faces, as each one tried to concentrate his mind on the pleasure the other was providing. In a few minutes they were each lost again in their own sensations, but now they were looking at each other unashamed, even a little fondly. It was so dear! Really, precious!

So I decided it was time for me to take care of my own slit, which by now had gotten pretty slick. There were two guys jerking each other off under orders, mine, looking like they were in love! That alone was enough to get me going! Also, I didn't want either one of them to realize fair is fair, so one of them could do me next, or I'd have to do both of them.

So I licked my middle finger and pushed it into me, and then when it was wet and slippery I diddled it back and forth across my clit, flipping that little button faster and faster. Real nice. I could feel myself mounting, oooh!, really reaching higher and higher, and in another minute Oh! Wow! I shuddered into a delicious orgasm, a tremendous squeezing and expanding of all of me all at once, a kind of explosive celebration of my pussy by my whole body! My first one always comes fairly quick, but this was my strongest ever, and it went on and on! When I opened my eyes I saw that Ronnie and Pete were still so absorbed with each other they'd never even noticed. They'd picked up the pace, and their breathing had gotten faster and deeper, and now their hands were flying across each other's crotches. Each one's face was twisted as if in pain, or in concentrated yearning.

"Stop!"

They froze, each one with his hand gripping the other's swollen dong, and looked at me dazed.

"Before you guys blow each other off, you should know what's my second Show and Tell. Now, my second one is, I want one of you to fuck the other in the ass."

They stared at me horrified. Pete swallowed, and swallowed again, but still couldn't say anything. His eyes avoided mine and stared into the middle distance. Ronnie swallowed too, then stared hard straight at me. I noticed neither of them let go the other's prick. I suppose they were afraid if they did their fun might be over, and by now they were both desperate to cum. That's why I thought I could get away with this.

"You're kidding!" Pete said finally. What he meant was, "You're serious!"

"That's not fair," Ronnie said. "If we did that what would you do?" He was talking at least, single syllables, and just barely thinking. Does a boy's brain close down when his cock rises? Anyhow, he was opening a negotiation! He was seriously considering my proposal!

I already had my answer. "Whoever gets fucked can fuck me," I said. "In the ass. That's fair."

I knew that was the clincher. Ronnie heard me loud and clear. I could tell by the way he was still staring into my face, his eyes lit by speculations I couldn't myself imagine! His cock lurched in Petey's hand. I bet both of these guys are virgins, I thought to myself. Well, my ass wasn't. The previous Thanksgiving I'd traded in its virginity to a cousin, for a baseball.

Well, it was a little more complicated, it happened this way. I'd gone off with that cousin, and had cheated on a game of forfeits, and had gotten him to kneel between my legs and slide his tongue in and out of my cunt while I was lounging back in a soft chair with my thighs resting on his shoulders, reading a book as if he didn't matter to me at all. He looked so sorrowful and so earnest, staring over my mound into my eyes while his mouth slurped and sucked on me, and I felt so good with him down there, that I let him know it when his tongue brought me off. That was a mistake, because then he felt good too, and wanted to fuck me. I told him no way with his prick, I was saving my pussy for my husband and the father of my children. He bought that argument, and asked instead for a blow job. Fair's fair, he pointed out, the way kids always do.

Well, just about then I'd been reading some stupid grownup woman's magazine that said that cocksucking was servile worship of the male phallus, and one of the ways men dominate women and keep them subservient, and stuff. I didn't know then that a phallus is really like the control stick in an airplane -- once you take hold of it you can fly a guy anywhere. One lick and he's yours, he'll do anything. But I didn't know that. I still didn't know it that day with Ronnie and Petey by the swimming pool, when I was getting them to play queer with each other.

Anyhow, I'd told my cousin I wouldn't blow him, no way, I was liberated and wouldn't demean myself. Then with a sudden inspiration I told him he could push into my asshole instead, if he'd throw in the baseball with Babe Ruth's signature his father kept in a little plastic shrine on the mantel. I'd always envied them that baseball, but mainly I was curious what it felt like to have a guy inside me moving in and out, what all the fuss was about. There was no way I'd let him into my cunt, because then he'd forever after lord it over me that he'd been Number One. Boys do that. My asshole he'd never boast about, because at that age most boys still think a back door is a shithole, and yukky. But he'd just been down there inspecting everything with his mouth and nose, and he knew that after my pussy my rosebud was the next best thing. So he agreed.

And he did it. We got him oiled up, and he got in after only a little bit of trouble, and he felt real good in there, but barely two swipes in and out and he came into me and then all over my ass. I was disappointed, but didn't let on. He told me later that his father really belted his ass over and over for supposedly playing with that baseball and then losing it, but that getting into me made it all worth while. I was his first. He was grateful, the way I like guys to be when they've done what I want them to do. The way I expected Ronnie and Petey to be when I was finished with them. I always give satisfaction.

Well, Ronnie just stood there staring at me, his dong still stiff in Petey's hand, its purple head poking out into the sunshine, and I could see that wheels were whirring in his brain. A chance to stick it to a girl at last! Or into Petey? But at what price?

Petey may not have registered any of it yet, that whoever gets fucked gets to fuck me. "You haven't whacked off yet, JayCee," he said, maybe stalling for time. "Or whatever it is girls do."

"Oh, yes I have," I said. "I came. You two lovers were too busy with each other to notice." I pushed two fingers into my quim, pulled them out gleaming wet, then stood up, walked over, and held them under Pete's nose. "What do you think this is? Or wouldn't you know?" I wiped my juice on his upper lip so the smell would last and maybe he'd get to like it, and then I gave Ronnie his chance, drenching my fingers a second time and then holding them up to his mouth. "Suck on this!" I commanded. He did, as if he were licking a candy cane. "You can do it, Ronnie," I told him in a low, sultry voice. "Be Pete's girl, for me."

I won that gamble too. I'd figured that Ronnie would calculate even in his coma that Pete's little cock shoved into him was a small price to pay to get his big one into me. I hoped so, but I didn't want him feeling too macho about it. Now whatever he did, he'd be following my orders. Better, in his own mind he'd be the girl who got laid, or he'd think I was thinking that. And once a girl in your own mind, I was thinking, always a girl. Once fucked, always fucked. I'll have to remember to call his cock a clit, I thought, and later I'll have to ask how his pussy felt with Pete's cum still leaking out of it. Because I had other uses for him now that I'd seen how obediently he'd licked pussy juice from my fingers. He'd be handy to have around when I felt like slinging my legs over someone's shoulders. More manageable than a cousin.

Ronnie finally decided. He pulled a few more times on Pete's pecker, then leaned in and muttered something to him, and then turned toward me. "He'll need lube of some kind, or he'll hurt me, JayCee" he said. His voice sounded very respectful. "How about we use some more of your juice?"

"I use my juice for me," I said with finality. "You've got a mouth, Ronnie. Take care of your own needs! Petey'll do the same for you afterward, blow job for blow job, won't you Petey?" I flashed him a smile to keep him encouraged, didn't even glance at Petey, then turned and sat down again to watch. Can you imagine? I was only fourteen then!

And sure enough, Ronnie looked at Petey, and Petey nodded, a little overwhelmed by all this wheeling and dealing. So Ronnie dropped to his knees in front of Petey and took Petey's little cock into his mouth. He gave it just a few licks all over to coat it with thick saliva, and only a few sucks and strokes up and down with his lips to spread the slick stuff around, but it was enough for Petey to forget himself, and stiffen up all the way, and then to start fucking his friend's face.

I was ecstatic! Here before my eyes was a boy I'd turned into a genuine cock sucker, home-made, my very first! I wished I had a camera. Petey's cock grew as swollen as it would ever get, sliding in the warm moisture of Ronnie's mouth, and his face again took on a glazed look. But Ronnie took no chances. He stopped suddenly, then got down on his hands and knees and lowered his head and chest onto a towel on the ground, with his butt way up in the air. Petey mounted him doggy style, spread his cheeks, felt for his asshole, and pushed at him a few times with that stubby cock.

At first all he did was shove Ron forward. But I could tell when he finally managed to get it into Ron, because on that stroke, the third or the fourth, instead of lurching forward when Petey's cock shoved on him Ron's body held steady. In fact Ronnie wriggled and snuggled back, and then Petey really began fucking him! Ronnie was now genuinely queer at both ends! I felt like a Maestro conducting an orchestra! A few more lunges, and then Petey was sprawled onto Ronnie, hugging him tight and squeezing his belly against his ass, and shouting "Hah! Hah! Hah!" Each shout another spurt of semen squirting into Ronnie's guts! Then Pete softened and flopped out of Ronnie's ass almost at once, leaving behind a trail of oozing cum.

Petey may have been small, but he had semen to spare. Ronnie's asshole was filled to the brim and running over. I bet he'll still be leaking tonight, I thought to myself idly. I'll try to remember to lend him a tampon before he goes home, or his folks'll ask about the stain on his bathing suit. I wondered if he'd want to fuck himself with the tampon while putting it in, now he'd had a taste of it, the way I sometimes do. He would if I told him to. Maybe he would for no reason at all.

I caught a glimpse of Petey's softened cock, and marveled that anything that small had even gotten past Ron's ass cheeks. But he'd done it! They both stood up. Pete's cum leaked down Ron's legs and glistened in his crack, and Pete looked like any boy who's just blown his wad, complacent and a little arrogant. Ron looked disturbed. I knew why, of course. He did feel more like a girl than he'd meant to feel, now he'd been irrevocably fucked by a stiff prick up the ass. But he wasn't a girl. Not with that cock, he wasn't. And he still hadn't managed to cum yet himself. It was time.

"Sit here under the umbrella, Little Peter," I said to him. "I'll give Ronnie back to you so you can be his girl next time, now that he's yours. Put your bathing suit back on now. If you can't find it I'll lend you some panties to wear home."


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sissychelle

This sissy is with You now for off and on 3-4 years and slowly but surely she gets Your program and discovers her true nature. In the beginning she was just a sissy on occasion and at “certain” times. But… Read more “sissychelle”

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