This story is fiction. It describes the relationships of some high school teens, including their sexual experiences. If this offends you, or if you are not at least 18 years of age, or if it is illegal where you reside to read such material, you must leave.
Copyright 2008 Charles Hughes, all rights reserved.
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MY HIGH SCHOOL BOYFRIENDS - Number 4 (t/t/M)
It turned out that Kenneth just talked to Jackie about it. Ray, Jackie's brother, wasn't gay; the two of them just got off together sometimes, Jackie said. But Jackie told Kenneth he was gay. And he wanted a boyfriend.
Kenneth had already left for college when I picked Jackie up one afternoon right before school started my senior year. Ray was off to college, too, but not the same one.
"Cool car!" Jackie said, as he climbed in.
"Let's just get some cokes and go somewhere and talk, okay?" I asked.
We drove around for a little bit. It was going to be great, having a car my senior year, thanks to Kenneth's folks. We talked about sports, the band, and school. Jackie was into art, and I told him I liked to draw. By the time I parked out by the lake, I think he was a little more relaxed. He'd been pretty nervous.
"Hey, I was nervous, too," I said.
"Huh?"
"With my first boyfriend.'
"Uh, yeah... I guess." He undid his seatbelt and turned to me. "So... why me?"
"Because you're cute," I answered. I grinned. "And sexy as hell. I will not ever forget that night in the hotel."
He giggled a little. "Shit, I could have killed Ray for saying that about my name!"
"I'm glad you didn't, Jackie. It was a good start to some great fun."
"Yeah," he grinned. "But he was only fooling around. Jackie is my real name; I mean, my name's John, so they call me Jackie. Ray and I..." He grinned. "Well, Ray just likes to tease me."
"Hey, how come he's cut but you're not?" I asked.
"See, we're really stepbrothers. My dad married his mom when I was four." He grinned again. He was so cute when he grinned! "So I came uncut. Ray explained the difference when I asked him once when I was a little older. I got hard when he told me, and so we played around. He showed me how to jack him off, and when I was old enough to cum, we did it together sometimes. Well," he laughed, "we did it a lot."
But then he got a more serious look on his face. "But I don't know much about being a... boyfriend."
"You want to be with somebody, right?" I asked. He nodded. "That's all you really need, just wanting to be with someone. Then it all comes naturally. You must be a pretty horny guy."
He grinned.
"What happens if I tell you I want to kiss you?" I asked.
"I get all boned up," he answered with hesitating.
"You ever kiss a guy?"
"Hell, no. I mean... Look, all I've ever done is jack off with my brother. Kenneth said... Well, he said you'd... ah... show me...stuff."
I moved over toward him. I reached over the console and put my arm around his shoulder, pulling him closer. I leaned my head toward his, and our lips met. He was warm and sweet. He was a virgin. I opened my mouth and moved my tongue into his. He was 14 and as eager as I'd been. We kissed slowly, our tongues twisting. I moved my hand to the back of his head and held him there as I fished deep in his mouth. We both had to gasp for breath when I pulled back.
"Holy shit." He whispered it slowly. And his eyes locked onto mine.
"Holy shit," he repeated. "This is going to be so good."
I grinned. "Sure is, Jackie. "I'll pick you up at 8:00 tonight. Wear those blue briefs, okay?
Well, that night I just drove out into the country, and we sat and talked for a while. We got out and took a piss. I watched the pee shoot out from that loose puckered skin, and when he was done I reached over and felt it. It was still wet, but I didn't care. The skin was so soft! I rubbed it between my fingers, and it felt warm. He started to get hard then, and we zipped up and got into the back seat.
I was probably grinning, because I was thinking of Kenneth and his cum spot on the floor back there.
We kissed, and he was so eager! I played my hand all around his crotch while we kissed, and then I unzipped his jeans. He helped me pull them off, and there were those blue briefs I remembered from the hotel. I pushed his legs apart and began to suck on him through the material like Kenneth used to do me.
"Awwww fuck Jimmy... yeaaaaa..." He was pushing his crotch at me. My lips found a wet spot, and I tasted his precum.
At the same time I'd been unfastening my own pants. He and I worked his briefs off while I pulled mine down. And that hard dick wasn't quite as long as I'd thought that night in the hotel. It wasn't more that four and a half inches. Wet. Slick cockhead. I stroked him lightly for a minute. Then I went down on him.
"OOOOOOOOOOO fucking yesssssssss!" He practically shouted.
I pulled away for a second. "First time you've been sucked?"
"Yeah... But don't stop for god's sake don't stop do more more..."
So I did. His pubic mound was really smooth, with just a few hairs. I licked that hot cock all around while he moaned as though I were torturing him on the rack. I gave little sucks to the underside of the head, and then I slid the whole damn thing into my mouth. That was all it took.
"Awwwwwwww gaaaaaad!"
He shoved his cock at me so hard I thought he'd bruised my lips! I sucked while he filled my mouth with the taste I knew I'd love from him. And I sucked until his moans softened to a whimper. I licked the last of his cream from his dick and let it fall from my mouth.
I sat up next to him, put my arm around him, pulling him close. I let him come down from his high as I stroked his hair. I kissed him softly on the cheek.
"I'm sorry... came too soon..." he said.
"You came just fine. Don't worry about it. There'll be lots of other times. I love you, Jackie," I said.
"Oh, Jimmy," he moaned into my chest. "I love you, Jimmy. I swear. I'm going to be a good boyfriend for you. I swear."
He was so eager to suck a cock for the first time I had to slow him down and tell him how to use his tongue and his lips. He listened to everything I said and tried his best. He'd get better. I pushed his face under my cock to get to my balls, and I really needed to slow him down, then. He would have eaten the damn things right off me! I got him calmed, and he licked me there and then moved back to my cock.
"Get ready to get fed, Jackie," I said quietly as he nursed on my cockhead. I showed him how to place his fingers on my tube, and then I lay back and enjoyed his first blow job. I had to remind him to slow down now and then, but I soon got to the point of no return. I shifted a little so I could shoot fully into his mouth.
"Here... it... cummmmmsss..." And my gut clenched as I shot my hot cream into him. He did great for his first time, didn't gag or cough. He swallowed and kept sucking. Finally I was finished. I had to pull his head off me, and he lay it on my belly, panting.
We finally took off our t-shirts, and I treated him to some real nipple play. He'd never known his nipples could feel so good.
"Mine are titties, Jackie," I said, "because they're bigger. Suck my titties, babe." And he nursed on them like he was a baby in need of milk.
We lay together naked in the back seat for a while, kissing and cuddling.
This was going to be good. Jackie had just turned 14, but he looked younger. He was so smooth all over. His chest wasn't really developed yet, still sort of flat with just a hint of his pecs. He had just a few dark brown hairs above his dick, not much there at all. But the hair was soft, and I liked stroking it with my fingers. He smiled at me now and then while we cuddled and felt each other all over, and those smiles usually led to more kissing.
His dick got soft after we just sat there holding each other for a while, and I reached down for it. There was just enough light that I could see the skin puckered up and hanging down from his cockhead. I rubbed my finger real lightly over the end of it, so soft. He moaned. I got it between my fingers and pulled it down a little; it could really stretch.
He started to get hard again, and I just held his dick in my hand. It looked so different than mine. As it got longer, the cockhead started to push through the foreskin, shoving it aside slowly. It made me think of an asshole being opened by a cock. That got me really hard! Pretty soon his cockhead was all the way out, and I leaned down and sucked him off again.
His cum was so sweet.
I usually drove over to his house to pick him up before school, and then I'd take him home, too. His folks were always gone until the evening, so we usually got naked and sexed it up. He was eager for his first fuck, he said, so I played with his hole. But I told him that would wait until we had lots of time.
His hole was really tight around my finger. I brought over some lube one day and used it. That day I played with his nut inside while I sucked him off, and he was so loud it was a good thing his folks weren't home! He shot hard.
Jackie had lots of pictures hanging on his wall, and I finally realized he'd drawn or painted most of them himself. He told me he liked art as well as music; he thought he was better at art. There was a little room next to his that he used when he was drawing or painting; he showed me how he'd set it up to use all the light from the big window.
One day I drew a little picture of him, just head and shoulders, and he said it was really good. I think he meant it. He said I should be taking art, but I told him since I was a senior it was really too late for me to start taking anything new. And that was when my boyfriend became my art teacher.
We used that little room together sometimes. We'd draw -- or he'd paint -- without talking at all, and then we'd look at each other's work. He was lots better than I would have been at painting, of course. And the smell of the paint made me horny. Sometimes we'd wind up sucking each other in there. He'd sit on a stool and I'd get between his legs and suck his nice little dick until he came for me.
Our first real night together was a couple of weeks after school started. His folks knew he was helping me learn drawing and I was helping him with some of his classes. I wasn't, but they didn't need to know that. We did a little drawing, and he drew a really dirty picture of me sucking his dick. I laughed and asked him if that was a picture or a wish. He unzipped his pants, so I got down and sucked him a few minutes.
We were both so horny by then, so we went into his bedroom. We stripped each other and got on the bed, kissing and caressing and moving our bodies all over each other.
"Did you bring your lube?" he asked.
"Sure did," I said.
He put his hands on my head and looked me in the eye. "Are you going to fuck me tonight?"
"Sure am," I grinned.
He dived down for my cock then, and I turned around so we could 69, with him kneeling over me. Since he was smaller than me, it wasn't much of a reach for me to move my face up to his balls. And then I started to lick into his crack. It was the first time I'd done that. It wasn't that I hadn't wanted to before. It was just that Jackie was a little shy about it all. He'd probably jacked off with his brother dozens of times, he'd told me, but having real sex with a guy was really different for him.
He groaned, though, when my tongue reached a little deeper. I'd fingered him enough that he knew where I was headed, and the thought of it being my tongue this time was getting both of us pretty hot. I rolled him over on his belly and pulled his hips up at little. He moved his knees to raise himself, and his virgin ass was mine to love.
I'd always loved it when Jason or Davie or Kenneth had eaten my ass. I remember being so surprised that it could feel so good. I wanted Jackie to know that surprise, that feeling. So I kept my tongue away from his hole for a little bit and just licked up and down his crack and around the inside of his cheeks. He was smooth as a baby back there. He was wiggling and moaning.
And he smelled so good!
The first time my tongue grazed his hole was an accident; it happened because he'd been wiggling so much, so eager for more.
"Uhhhhhh... gaaaaaaaaawwwd Jimmy..."
So I lapped at his warm, wet hole like a puppy at his water dish. I washed it all around and slapped my tongue at it; then I rubbed with with the rough side of my tongue very slowly.
"Ohhhhhh yesssss..." he cood.
I pointed my tongue and headed for the virgin hole. Nobody had ever been in there before. For fourteen years, that entrance had been waiting for me, and I wanted it. I pushed my tongue slowly, and Jackie moaned as the hot, tight hole resisted me. I kept pushing, alternating with some licking now and then, and when his hole relaxed just a bit I pushed his door open and was in!
Jackie's musk was already making me light-headed, and now the slick, smooth tissue of his hole was almost more than I could take. My virgin Jackie was giving all of himself to me; my virgin boyfriend was offering his entrance to what invaded him. And there was something even bigger waiting.
I tongue-fucked him for a while, pulling a pillow up under his hips so he wouldn't get tired in that position. He kept stretching his legs, as though he were asking me to simply crawl inside him, all of me.
When I pulled away I worked his hole with one finger, but since I'd done that before it took little effort to get a second finger in. I moved them around and around, and his noises made him sound like a little kid. He'd moan and then whine and then squeek and then breathe out a long, raspy sigh. He was so silky-smooth inside. I worked him a long, long time. He was so sexed-up!
The third finger made it very tight for him, but he took it. I had gotten the bottle of lube, and I dribbled a few drops on his hole, working it in.
"We're getting closer," I whispered, "closer, Jackie. Your hole is relaxing for me; my fingers feel all the heat inside you. I want my dick in there to soak up that heat; I want to slide all the way down into my boyfriend..."
I got him to roll over onto his back then; he pulled his legs up, and his wet asshole was pulsing at me. He was cute like that, his thin, smooth legs pulled up to his chest; his legs made a "v" pointing down to his asshole. I slipped my fingers in again and began to caress him inside. His eyes were locked on mine, but they were glazed over, like he was in some other world.
I kept whispering as I dribbled some lube on my hard cock. When I pulled my fingers out, my cockhead was right there. His ring had shut his hole firmly when my fingers left, but I pressed my cockhead against its slickness.
"Oh please Jimmy yes put it in yes fuck me..." His eyes were focused on me now, and then moved from my face to as much as he could see of the invader at his ass.
He was eager for his first fuck, but I knew he was also anxious, a little uncertain about just what was going to happen.
I wanted inside my virgin boyfriend so badly. But this was going to be good for him. I was going to make it good. I pressed a little harder, and I could feel that hot pucker relax just a little. My cockhead was a deep red; his little ass was so very white. I pressed again, then again. It was opening... I could feel it. Ring sliding up my cockhead, tightness relaxing just enough... sliding in slowly...
When his ring snapped around the crown of my cock, Jackie yelled. But he'd been expecting it, and his face was buried in a pillow. I stopped and rubbed him gently over his few pubic hairs. He let the pillow fall away and looked at me, his mouth open, breathing hard.
"You'll get used to it, Jackie. Just relax. It'll go away. It's okay, Jackie." I just whispered for a while to let him adjust.
"I'm going down, Jackie. Remember; push out like I told you."
I slowly pressed. And I could feel Jackie push out. My boyfriend wanted his virgin ass to be mine! His lips pursed in concentration as I pressed my cock inward; he responded by pushing out, accepting me. His slick tunnel was so tight; the heat almost made my cockhead burn. I slid slowly inward, hesitating now and then to let him catch a breath. My cock felt like it was a foot long.
Then my pubes were on his ass and pressing into his balls.
"Oh, Jackie; I'm in... all the way."
I looked down at him. He'd spread his legs, holding them behind his knees. There were tiny beads of sweat on his smooth chest, and his nipples were pointing upward. He was beautiful. He was giving me his cherry.
"God, I love you, Jackie."
This brought a smile to his face. "So... tight. God, yeah. Oh, but, Jimmy, I love it. So full! mmmmmmmm..."
Then I moved my hips side to side. My cockhead moved around deep inside him, as though it were tasting everything it could of him. And I pulled up slowly.
He groaned. So did I, as I felt that wet, warm tissue slide past my cockhead, my shaft, upward slowly slowly god yessss until only my cockhead was inside him.
I looked down. My shaft was glistening with the moisture, and the lips of his hole were a deep, deep red. His cock was lying on his balls, soft but pulsing, the wrinkled skin at the end leaking a drop of precum.
I fucked in slowly. I could see him relax a bit. I pulled out, and when I fucked in again he pushed back at me. It was amazing, watching my cock drill into his hole. I looked at his face again.
"It's... so... awesome... oooooooo... so good now..." His eyes were on my face, but he looked so dreamy.
We fucked slowly for a while, and now and then I'd reach down and pinch a nipple. He'd react with a lazy, dreamy smile or groan. And I reached for his cock as I fucked and watched the head of it appear slowly, pushing aside the soft foreskin and leaking its precum. I fucked slowly, in and out, as I stroked his hard dick, up and down...
We were both lost in that place where only boys can go, where moans are music and sex is the entire world.
The tension in my gut brought me back to myself. I would seed my Jackie, claim his ass as my own, shoot myself deeply into him...
"Gonna... cum... soon..."
"Oh yeaaa... yeaaaaa cum in meeee..."
I jerked his hot dick as I plunged into him over and over again. I was moving wildly with the need... ramming into his virgin pussy... filling his love tunnel over and over with my cock...
And I blasted my first shot with such force it almost stung the inside of my dickhead as it rushed through and forced my peelips open...
I came again and again, filling his ass with my cream...
Somehow I was aware of two voices in the distance somewhere, moaning their deep pleasure as their bodies gave everything to each other.
When I'd shot the last of it, my cock was surrounded by my cum inside him. And I had his cum on my hand; he'd cum while I was flying past his nut deep inside him.
I groaned as I pulled out of him. His arms and legs fell to the bed, and I collapsed next to him, one arm and one leg across the boy I'd just fucked. For long minutes, there was no sound at all except our ragged breathing.
"Ooooo Jimmy..."
Then, "Ooooo Jimmy... That was unbelievable..."
Later that night, he had to fuck me, of course. It seemed he was a little hesitant about licking my pussy, and I told him he didn't have to. But he said he wanted to, and very soon his warm tongue was tasting everything back there, his moans telling me he loved it. His fuck was just a little awkward, but for his first time he did really well.
We kissed and talked and played almost all night, and in the morning, before we went down for breakfast he kissed me and told me it was the most wonderful night of his life. I told him there would be lots more.
It was always fun, doing things with Jackie. Not just the sex, but lots of other things, too. I was still volunteering to help with the band, so I saw him lots of times at practice. We didn't have any classes together, since I was a senior. I went to all the football games, only I drove to the away games when the band played.
Jackie liked to reach over and play with my dick while I was driving. I never let him get me too hot while I was driving, though, because that would be dangerous. Sometimes I'd get him to drop his pants to the floor over there in the passenger seat. I liked to watch him play with his dick. And he'd open his shirt and play with his nipples for me, too. A few times on the way back from somewhere we'd pull off onto a country road and suck for a while.
Once I dared him to strip naked in the car when we were coming home from a game. We weren't on any interstates that night, just two-lane roads, so I finally convinced him to do it. Then I started talking about how sexy he looked until he was so horny he couldn't keep his hands off his dick. Then I dared him to jack off, and he was ready for it! His cum shot so hard some of it landed on the dashboard!
Having the car was cool, because we could go lots of places. And right after Christmas break we had a chance to make a real trip together. There was a new exhibit of impressionist paintings in an art museum in a city about three hours away from us. He really wanted to see it. He finally talked his parents into letting me take him. And since it was so far, we'd spend the night in a motel over there and come back the next day.
The exhibit was really great. It was a huge museum, and we wandered around for a long time. We were both pretty eager to get to the motel, of course, so we just ate at a fast food place. His dad had made reservations for us -- he said he had to do it because of our ages -- and we got there in the early evening.
Jackie threw his duffle bag on the bed as soon as we entered the room, and he turned to me, threw his arms around me, and kissed me.
"Damn, I've been waiting for this!" he said. "Sex in a motel -- how hot is that!"
"Hey, stud," I said with a grin. "Who said anything about sex? You're making an assumption."
"An assumption, huh?" He was throwing off his clothes as fast as he could. "Does this look like an assumption?" He was standing there naked, holding his hard cock out at me.
"Looks like a dick to me," I said. "What makes you think I'd be interested in a dick?"
"Well, that lump in your jeans might be a clue." He reached for my crotch, but I turned away, laughing.
"Come on, Jimmy; I've been horny all day."
"Is that why you were looking at my dick while I pissed in the restroom at the museum? I almost reported you to the guards," I laughed.
"Piss on this, Jimmy!" He stretched his dick out at me.
"Okay," I said, matter-of-factly. His face went blank, like he didn't know what to say next.
I stripped quickly, and we left our clothes lying all over the floor as I pulled him into the bathroom.
"You need a shower, Jackie," I said. I pulled him into the shower. I pointed my dick at his middle. "I hope the temperature isn't too hot."
His mouth dropped open when he realized what I was about to do. My stream started, and I had to get a little closer to hit the mark -- his pubes. He giggled and dodged away, but there wasn't anywhere to go. He turned around, and my piss hit his ass.
"No, you don't," I grinned. "You told me to piss on your dick," and I pulled him around to face me again.
"You're nasty!" he laughed.
I pulled one hand away, and he slid down to the floor of the shower. He was still laughing, but he spread his legs so I could keep the stream on him. I moved it up to hit one of his nipples a second, then I finished the last of the stream on his dick.
"Damn, that made me horny!" He grinned.
"No, it didn't," I smiled. "You were horny before you set foot in the room."
"You got that right," he said. "Now it's your turn."
He stood up and aimed his dick at me. I couldn't very well object, since I'd started it. His piss dribbled from the little pucker of his foreskin, and then the stream started spurting out of it. It was sexy, watching piss shoot out of his uncut cock. His piss was hot against my skin, and when it ran down to drip off my balls I started boning up. I just spread my legs and let him piss on my dick until he didn't have any left.
We weren't laughing anymore. We moved together and put our arms around each other. Our tongues were searching even before our lips met. The warmth of our piss was wet between us, and I could feel both of our cocks. I let my tongue rest while he searched inside my mouth and as far back as he could reach, and then my tongue met his for a slow, moist dance.
Neither one of us said a thing as I turned the water on. It was chilling at first, but it warmed up quickly. We just held each other, letting the water run down our bodies. He stepped back a bit. Our dicks had pretty much deflated under the sudden shock of cold water, and they were still soft.
He reached for his dick and got a finger inside his foreskin. He pulled and stretched it, using his other hand to hold it open.
"Put it in," he whispered under the sound of the water.
At first I didn't understand what he meant. Then I saw that his foreskin was making a little tube, a little tunnel... And he wanted my dick inside it.
I held my dick up and moved it to the open mouth of his foreskin. And I moved closer as he covered my cockhead with his skin. I had almost forgotten to breath. The sensation was unbelievable. The water from the shower was running down my back and a little over my chest. And my cockhead was completely surrounded by the heat and softness of his skin. Like a glove...
"Oooooooo... Jackie..."
With one hand he kept his dick in place, and with the other he held his foreskin around my cockhead. Then he began to slowly move that hand back and forth. I watched with my mouth open. He was jacking us off. He was moving his soft skin back and forth around his own cockhead at the same time he was moving all around mine, with my cockhead completely covered...
He stroked slowly, and our moans joined the hiss of the showerhead...
Time seemed to stop as he jacked us together. My legs weakened, and I put one hand on his shoulder and the other on his hip to steady both of us. He stroked the two cockheads trapped together inside his skin, each of them oozing precum now, wet, slick, hard...
I could hear a little whine, and I realized it was coming from me. I was going to cum. I felt completely relaxed inside, but I was frozen in place. I lay my head on his shoulder. His hand moved so slowly it was almost agonizing.
"Oh." It was just one tiny little sound from him, but it was the beginning of his orgasm.
And the sudden burst of his cum against my pisslips made me cum immediately. I couldn't move. I couldn't break that wonderful contact. But I came hard with little grunts. I could feel my cum collecting inside his foreskin... his cum collecting with mine... Oh, the relief the wondrous relief as my cum shot over and over...
We were leaning into each other when our orgasms stopped, and we breathed deeply. I watched him slide his foreskin back up my cockhead, keeping his fingers tightly around it. When he pulled away, my cockhead was wet with cum from both of us.
His fingers were pinching his skin and holding it closed. His cockhead was trapped in there... our cum...
"It's for you," Jackie whispered.
I knelt, not even feeling the hard floor of the shower under my knees. I placed my mouth around the tiny pinched lips at the end of his foreskin. He let go, and I felt and tasted the rush of cum into my mouth. I licked and swallowed. I swirled my tongue around his cockhead and up under his foreskin, down around it, inside it for more... more of our cum... tasting us... swallowing us...
He was whimpering when I came out of my stupor. His cock must have been very sensitive. I released it from my mouth and lay my forehead against his pubic bone. He slowly slid down, and we slid together against the wall of the shower. We just lay there.
We finally regained our senses. We stood carefully and, without speaking, soaped each other off. We stepped out of the shower. He dried me all over first, and then I dried him. We fell onto the bed without even pulling down the covers.
We fell asleep. Later, during the night, I woke to find him sucking on my dick. We moved into a 69 in such a way that our fingers could delve as deeply as possible into each other's hole. After we'd both cum, we fell asleep again.
I woke to find the sun coming in between the curtains. I felt him stirring beside me. Then he cuddled up next to me.
"I love you, Jimmy," he whispered.
It was the first words spoken since our fantastic experience in the shower the night before. It was nice. I knew he didn't mean the forever-and-ever kind of love, just the love-for-right-now kind, but it was still nice. I loved him, too.
It was still early, though. We cuddled for a while, and then we fucked each other. We just had time to take a quick shower before the checkout deadline.
One night we were at his house, and he said he wanted to draw me nude. I laughed and said he'd have to draw me hard. He was serious, though. I got naked, and he lay me down on the bed the way he wanted. I was kind of propped up on one elbow, and my dick -- hard at first, of course -- finally went down and lay on my thigh. He got one of his big sketch pads and sat across the room.
It took a while, because he was pretty particular. Then he showed it to me. I was impressed. It made me look sexy. But he was honest about my big titties and big ass. It was me, all right. But he made me look sexy as hell. I rewarded him with a nice long blow job.
I asked him what he was going to do with it. He said he'd keep it. He had someplace where he kept things hidden from people, and he said he'd keep it there. I was a little nervous about it, because I didn't want just anybody seeing me naked. But I trusted him.
I also trusted him when he talked me into entering the art contest the school was holding. I told him people would laugh at anything I did; I just wasn't that good. But he talked me into it.
The contest, I discovered later, was supposed to be just for art students. The art teacher had told him my drawing -- it was a pen-and-ink landscape -- wasn't eligible. He told the art teacher that it wasn't specified that you had to be in an art class to enter and convinced her to leave my drawing in. And I won second place! Jackie won first place, of course. And I was so proud of him!
We celebrated with an overnight at his house.
In the spring, Jackie started getting a little moody now and then. It took me a little bit to understand what was going on. I had decided to go to college, after all; for most of my high school years I'd thought I was too dumb. I started talking to my counselor and getting information about colleges. That's when it started.
"You have to leave," Jackie said. "I know that."
We were sitting on my bed looking over some college catalogues. I kept leafing through one of them. I wasn't sure what to say.
"But I don't want you to," Jackie finally finished. He turned over and buried his face in a pillow. I'd never seen him cry before.
I pulled him up and put my arms around him, and he cried quietly into my shoulder.
"I have to go, Jackie," I said, rubbing his back.
"But I love you," he cried.
Not until that moment had I realized what I had to do. It just hadn't dawned on me. Jackie would be all alone. And it was my job to get him a boyfriend for the next year. It was my responsibility. Davie had done it for me. And then Kenneth had done it for me. And now I had to do it for Jackie. I just couldn't leave him alone.
I didn't say anything about it then. I didn't know what to say. And I didn't know what to do. How could I go about finding a boyfriend for Jackie? How could I ask somebody? How could I know who to ask? I worried about that before I went to sleep that night. And for a long time afterward.
I'd never paid that much attention to most of the boys around school. Well, not that kind of attention. I mean, I knew who looked good and who didn't. But I didn't know who was gay. How could I know that? I'd never been with anybody except my own boyfriends. Well, not counting Mr. Harrison, but that was different.
Mr. Harrison. Mr. Harrison. I kept thinking about him. Was there another teacher... That was stupid. How would I know?
Mr. Harrison.
Somewhere I'd heard that Mr. Harrison had gotten a job teaching at a high school in a town about 40 miles from ours. Was he still there? Was it crazy to think... that maybe Jackie and Mr. Harrison...?
I found his address. One Saturday I drove there. I thought it would be simple. Just go see him. But, shit, I was scared to death! It was crazy! But I went anyway.
It was a town about the size of ours. I remembered seeing their team play us in basketball. I found his house. I knocked on the door, and he answered. I was so scared I about pissed in my pants.
"Yes...?
He hadn't changed at all. Still tall, built like an athlete... I suddenly realized he didn't have any idea who I was. I almost turned around and ran back to the car.
"Um... Mr. Harrison..."
"My God. It's you! What are you doing here?" He was staring at me.
"Uh... I just wanted to talk... Uh... could I come in, just for a little bit?"
Well, it was pretty awkward at first. He offered me a coke, and I took it. I realized he might think I was there to cause him trouble about what happened between him and me, and I assured him that wasn't it at all. It took me a while to stammer around to what I wanted. I finally got it out. I told him that I had a boyfriend, a really nice guy. I told him about Jackie -- without telling him his name. And that Jackie needed a boyfriend for the next year. Was Mr. Harrison interested?
He sat there, his eyes so big I thought they'd pop out of his head! I didn't know what else to say. If he didn't say anything, I'd just have to leave.
"You tell that Davie of yours I'm no patsy for some setup. Get the fuck out."
"Huh? No, no. This doesn't have anything to do with Davie. My boyfriend is only a freshman... Wait a minute. You think I'm trying to set you up or something." I could tell by the look on his face that's exactly what he was thinking.
"No, Mr. Harrison. Look, I'm really sorry about what happened with you and me. Well, and Davie. I didn't even know about it ahead of time. This is something different. I'm telling you the truth. My boyfriend needs somebody. I just can't leave..."
I could tell he still didn't believe me. Shit. How could I convince him?
I took my shirt off, then my t-shirt. He stared. Okay, I'd begun to develop a little, but my titties were still big titties.
"This is real, Mr. Harrison."
I pushed my shoes off as I undid my pants and slid them down. Was this crazy? But I had to convince him! I was left wearing my socks and my briefs. I was so scared I think my dick had crawled up inside my belly.
"My god." He just sat there.
"This is real, Mr. Harrison. I love Jackie" -- I could have bitten my tongue when I said his name, but it was too late -- "and I can't just leave him without anybody. I know it's another town. But you have a car. I mean... Ah, look. You still like boys, right?"
Mr. Harrison swallowed hard.
"I swear this isn't a trick." Did I have the guts? It was for Jackie.
I pulled my briefs off.
My dick had never been so small. Well, not since I was a little kid. I was shaking. Shit. Naked alone in front of a man... what was I doing here!?!
"You'd like... Jackie..." I said. Even my voice was shaking. "He needs somebody, Mr. Harrison." I swallowed. "I'll bring him over myself a few times before school is out in May..."
That's when I noticed his bulge. Well, if he was ever going to be interested in a boy, it would be when one was sitting naked right in front of him! He already knew the flavor of my dick... And that thought -- and the sight of his bulge -- woke my dick up.
"I'll be here with him a few times, Mr. Harrison," I said quietly. I stood and walked slowly to his chair, my thickening dick swaying in front of me. "He's cute, Mr, Harrison. He's not like me. He's a beautiful guy."
I stood right in front of him. I held my dick in my hand, stroked it once, and held it out to him. Without a word, he leaned into me and sucked my dick into his mouth. His moan vibrated into my balls.
"Awww yessssss Mr. Harrison..." I adjusted myself for him a bit and put my hands behind his head.
I could feel the precum oozing out for him. His tongue worked my cockhead around and around. He sucked me in and pulled away only to suck me deeper. I felt his hands on my ass, separating my cheeks. I fucked into his mouth just a little, meeting his sucks. His fingers found my pussyhole and stroked it.
"Yessss, Mr. Harrison... Make me cum for you... Oh yessss..."
One hand moved to my balls, quite a bit bigger than the last time he'd touched them. He sucked fast and hard, like he hadn't had a dick since... well, since me. I warned him. Just in case he didn't want me to cum in his mouth. But he wanted it. He sucked faster, and I felt that point, that point where it's too late to stop it. I moaned deep and pressed at him.
And then I shot. Over and over, I came into his mouth, feeling the suction as he swallowed my cream. I fucked his mouth and cum just shot out. I moaned. He squeezed my balls, and I shot more. When I was finished, I had to sit down on the floor.
It was silent for a moment. Then I heard him whisper, " Sweet... sweet boycream..." He was staring at me.
"Damn," I said, hardly recognizing my own voice. "Damn, you're one hell of a cocksucker."
He smiled. "You've got one hell of a cock, Jimmy. Tell me more about your boyfriend."
So that's how I set up our first meeting. It was lots harder convincing Jackie, but I told him about how nice a teacher Mr. Harrison had been, how everybody liked him. And I told him all about how he had gone down on me a couple of years ago, and how good he was. Jackie finally agreed that he'd go with me to see Mr. Harrison the next Saturday.
Jackie was nervous as hell when we got there -- well, so was I -- but Mr. Harrison was nice, and he let me take the lead. I started playing with my dick through my pants while we were talking, and pretty soon everybody was hard! Boy, was Jackie surprised when he found out that Mr. Harrison was uncut, just like he was. Jackie got to suck him before I did, but I didn't mind, because he was so excited about it.
We let Mr. Harrison play with us on his bed for a while, and it seemed he liked Jackie's nipples as much as he liked my titties. He sucked both of us, too, all over. It was hot, being in bed with him. He was really strong and well-built, and he liked to laugh and horse around like we did.
He was fingering my ass when he asked me if he could fuck me. "I've had so many great jack off sessions remembering Davie fuck you in front of me! I know it's big," he said, motioning at his cock, "but I'll be careful. I don't enjoy hurting anyone. I enjoy loving them."
And so, with Jackie lying there watching us, Mr. Harrison lubed up my pussy and fingered it for a while. Then he lubed his big cock. The foreskin had pulled all the way back, and it was such a deep red it was almost purple. He stroked my back and ass as I lay on my belly and assured me he'd be careful.
When that huge cockhead was inside my ring, I thought I'd split wide open! He pushed in slowly. Then I heard him take a deep breath. And he slid all the rest of the way in quickly. I sucked in my breath. It hurt!
"Fuck!" I yelled.
"Oh god, little Jimmy, you have such a great ass. I want your pussy, Jimmy, I want your ass, baby, I want your ass..."
He started to pump pretty fast, and I was being stretched too much.
"Fuck! Pull off me!"
He froze for a moment. Then he slowly pulled out, and that hurt as much as when he rammed in. When I rolled over, I saw there were tears in his eyes!
"Oh, shit, Jimmy, shit I'm so sorry I'm so sorry so sorry."
He turned his back to us. I could see he was crying quietly.
"You just don't know, you just don't know," he said. "It's been so long. I'm so sorry..."
Jackie had a shocked look on his face. This wasn't what he'd expected. Well, it wasn't what I'd expected, either! I moved over and lay my hand on Mr. Harrison's shoulder. He turned to look at me. I'd never seen an adult cry before.
"I... I can... control myself. Jimmy. I swear."
"I won't have you hurt Jackie, you hear me?" My voice was a little sharp. "I love him. And I want you to love him, too. If you can't do that..."
"Please, Jimmy... Please..."
"Fuck me, Mr. Harrison. And this time do it right. Or you can't have Jackie."
And he did. He slid in slowly, and it was a thrill to feel that big, thick, long cock sink into me. It hurt for a little bit, but pretty soon it felt better. And then it felt so good I could hardly remember that it hurt. He hummed a little as he began to stroke, and now and then he'd ask if I was okay. I assured him I was. He adjusted himself, and his cock began to stroke my prostate inside. I moaned with the pleasure he gave me. He became gentle, stroking my back and whispering in my ear how pretty I was.
I made sure Jackie understood that I was enjoying it, that Mr. Harrison knew how to use his cock without hurting. Jackie kept his eyes on Mr. Harrison cock as he pumped in and out of my ass. And he kept his hand on his own hard dick.
Then Mr. Harrison got closer to the time. Well, so did I. I thought maybe he was hesitant to pump very hard because of before, so I encouraged him.
"Fuck me now, Mr. Harrison. God, I'm so turned on by your cock! Fuck the shit out of me! Fuck me!"
And he did. He rammed his long cock into my pussy, and I just couldn't get enough of it. I shoved back on him, and when I felt him tense and begin to cum I rammed back just as hard as he rammed into me. He came with long, deep grunts. There was so much I could feel it oozing out of my pussy while he was still blasting it in.
When he was done, he rolled over me carefully so he wouldn't fall on me. His eyes were wet again, but he had such a sweet smile on his face.
"Jimmy, Jimmy," he whispered. "I haven't been this happy for years."
"We've got the rest of the afternoon, Mr. Harrison. You'll be happy when you fuck Jackie, too." I grinned.
"Oh god, Jimmy." Mr. Harrison looked over at Jackie, who was stroking his dick. "I don't know if I can recover enough for that."
"Sure you can," I said. "We'll see to it."
And we did. Wow, I loved watching that thick cock of his thrusting into my boyfriend. He was much more careful this time. I made sure of that. I hadn't intended to let him fuck Jackie yet, not while he was still my boyfriend. But I decided Jackie's first time with Mr. Harrison should be right then, right as I could watch and make sure everything was okay for him.
Mr. Harrison took a long time getting Jackie ready for the biggest cock that had fucked him so far. I honestly wondered if it would work. But when Mr. Harrison's big fat cock coaxed Jackie's little pucker to open, I knew it would be fine. I sat next to them and jacked on my dick as I watched that huge cock slide into Jackie's tunnel. Mr. Harrison went slow for him at first, but as Jackie got used to the fullness the fucking got a little faster. And Jackie groaned his pleasure as Mr. Harrison came in boypussy -- Jackie's second fuck that afternoon.
When it was over, the smile on Jackie's face told me that he was very happy himself. This would work out well for both of them.
Jackie and I went over to see Mr. Harrison three more times before school was over. It was great each time. Jackie and I had one last overnight together at his house right before graduation. After that, he would be Mr. Harrison's boyfriend, not mine. He cried. Well, actually, I did, a little, myself. It was a night of tears and sweet sex.
Well. Those are my boyfriends in high school. But there is one more. I'll have to wait and tell you about him the next time.