Military School by R.B.W.
Watch for the switch. It's a bit abrupt and probably too clever, but it's done...
I've calmed down quite a bit since high school. I used to do a lot of drinking with my friends, going to the kind of parties the cops would break up in an hour, after the neighbors had complained about the music. We had some good pranks going, too, like the time we let three science-laboratory rats into the girls' locker room. That one was a real riot. After being suspended for about the third time, my parents couldn't handle the pressure anymore, and despite my pleading, shipped me off to military school. The blond guy I shared a room with my junior year, a sophomore named Kurt, although a bit of a prick, was there for reasons that were never really clear to me. He was a real homo, never played any sports, and most of the little time I did spend in the room he used up involving me in annoying discussions about what color socks he was going to wear to liven up the navy blue uniform. I guess his parents thought, incorrectly, that military training would "straighten" him out. I couldn't stand him.
He got cocky on me, once he realized I was not having his shit, and he bitched about everything. So I really only slept in the room; the last thing I wanted to do was get undressed in front of this guy. I even talked to the resident officer, a friend of mine, about getting my room switched, but he said there was nothing he could do. Kurt and I actually went through a period of basically not saying a word except "hey" to one another. But after about three months of this avoiding-my-room business, I started to get frustrated and decided to just fuck it. I started hanging out there more, but kept to myself, and just concentrated on my homework. I even got used to my underwear, I mean, what was he going to do? I figured, "let him go ahead and look, I don't give a shit." And I guess he looked. I played some baseball, and soccer and football less, and I guess my body looked alright, not that I'd been comparing mine to anybody else's.
Around that time I discovered he had a habit of jerking off late at night after he thought I was asleep. Personally, I would always just go to the john to take care of it, but I guess he felt comfortable doing it with me on the bunk right above him. Curiously, it always seemed to happen when I would come back from the showers in just a towel, like on weekends when I had the time to chill out before getting dressed. I would be napping and all of a sudden I would wake up to the sounds of heavy breathing and the creaking of bedsprings. That would last a few minutes and then he would be stifling these grunts. There was this framed poster on the wall across the room from our beds, a promotional thing from the Yankees winning the World Series, and what I'm sure he didn't realize was that I could see him very clearly in the reflection of the glass, down at the dark bottom half of the poster. I would look over to see his naked body tense up, his crotch arch up in the air, and him cumming all over himself. Then I would see his hand reach over to grab some tissues off of the dresser, and he must have had powerful balls because more often than not, he would also have to wipe off the underside of my bunk.
One Saturday, I had been playing touch football with four or five other guys. It was a tough match. I'm about a hundred and fifty-five pounds, not as big as a couple of the guys on the other team, so I came back exhausted, soaked in sweat, and stained with dirt and grass all down my left side. There's no reason to play if you're not going to get all fucked up, though, that's the fun part. I almost threw my jock strap into the garbage, it was so sweaty and dirty, but I decided there was no point in being extreme about it. I just threw it in my dresser and forgot about it. It turned up missing the next time I looked for it, but there isn't much mystery to where it went.
After cleaning up, I came back to the room and wound up falling asleep in my boxers. When I woke up again and stretched, I heard him scrambling around below me. I dropped my head over the bunk to ask him what time it was. He was in this fetal position under the blanket that seemed like he was hiding a hard-on. I mean, I guess he could have just been relaxed like that, since he was "reading a book," but I wasn't convinced. Plus, he answered me with the reddest face, and couldn't make eye contact with me. I knew at that point that he was up to something, I just wasn't sure what it was. For some reason, don't ask me why, I just didn't care. I suppose I didn't think he could really do any harm. I could kick his sorry ass anyway. For a goof, I decided to play with him and freak him out, so before my own hard-on had subsided from my nap, I dropped down, sticking my hard dick where I knew his head was. I pretended I was fixing something on my bunk as I stood there, and of course I had to lean in and shove my dick right in the direction of his face. I got dressed and went out. When I said "see ya," he said, "later," with this dumbfounded look on his face. I bet he had some fun with that one. So did I. I smirked the whole way to the cafeteria.
Over the next couple weeks, I got a kick out of wearing only my boxers whenever I was in for the night. I loved watching Kurt squirm whenever I would ask to borrow a pencil or something (plus, he hated that) while I stood there and nonchalantly played with my balls. The best was when I would do some push-ups or sit-ups on the floor, and I would not be the only one in the room breaking out in a sweat. He would be "reading," but strangely, wouldn't turn a page for five minutes at a time (I guess he was a slow reader). One night I even jerked off for him on my bunk. It was really late but I put on a good show if I do say so myself, and I'm sure he heard me. I made sure there was no way he could not have. First, I stripped naked and dropped my boxers right next to him on the floor so he would know to envision my naked body. Then I started stroking my eight inches with more fervor than was necessary to get the job done, so that the bed would creak and actually bang up against the wall a few times. I tortured him like that with his own medicine for a while, but the weird thing was, the idea of the little faggot down there getting all hot over my hard cock was actually making me cum even faster. Jerking off in a communal bathroom teaches you to be quiet about it, but when I came this time, I panted and moaned, and to be honest, it was not all fake.
The only problem with my gags was being at this all-boys school out in the middle of nowhere, right at the height of horny pubescence. Sure, we had the dances with St. Mary's on the other side of town, but they were few and far between. And even then, there was no guarantee that you'd be able to sneak out of their gym with a girl and get a shoulderful of knee-socks. There were the times when I wasn't sure I could take it any more, and it didn't help that there was this mouth not three feet below me that was itching to take care of my dick, whenever it needed it. The jokes I was playing were getting steadily less funny...and then it happened. I was working out one night, I think it was like a Tuesday or something, and Kurt was reading, there on the bottom bunk. He was lying on his stomach with his feet at the pillow end, in just his pajama bottoms and no shirt. The pajamas were loose around the waist from wear-and-tear and they fell low enough that I could see the curve of his ass and just the top of his crack. Every once in a while he would readjust his position and stick his ass up in the air like he was offering it for service. He wasn't especially muscular, but he had this smooth little body and the nicest tight round ass.
He was sucking on a Blow-Pop with all kinds of tongue and was not trying real hard to hide the fact that he kept glancing over at my crotch thinking about giving my dick the same treatment. It's fine when it's just a joke, but my dick was getting harder by the minute, so I decided I was too uncomfortable to finish working out. I crawled protectively on hands and knees over to the dresser and grabbed my towel off the hook it had been hanging on, so that when I stood up I could use it to hide the growing hard-on that my boxers refused to. "Uh, I'm going to take a shower," I said to him more meekly than I would have liked. He pulled the Blow-Pop slowly out of his mouth and looked down my stomach to where I was awkwardly holding the towel before answering, "okay, I'll be here." Then he stuck his tongue out for the Blow-Pop and sucked it back into his mouth, still staring into my eyes. I was frozen there for a minute against my will before I was able to tear myself away and go to the showers.
Luckily, the showers were separate from each other and although you could see through the smoky glass doors, most of the other boys had washed up earlier and had not yet arrived to brush their teeth for bed. Soaping up my dick made it spring to life in my hands, and I was starting to get into the sensation when I heard the door open and close. Quickly, I let go of my dick and turned towards the wall. "Hey, uh, Matt?" it was Kurt. He was not very loud about it.
"Yeah. What's up?"
"You forgot your shampoo, do you want it?"
"Uhhh, yyyeah, alright. Hold on a sec." There was no chance of my dick letting me off the hook, so instead of opening it, I stuck my hand out over the door. Kurt gave me the shampoo and softly brushed my hand with his, a little more than was necessary. "Thanks," I said, "I'll be back in a minute."
"Kay." I went back to washing my aching balls and underneath them, but when I thought about it, I hadn't heard the door again, and I looked up to see the outline of Kurt, still standing there, watching me. I stopped washing, and he turned around and left. I thought about Kurt a while longer as I rinsed everything, realising that having him watch me was really turning me on, and that I was not going to be able to prevent the inevitable. I reached out the door and grabbed my towel, only half-heartedly drying myself with it, and positioned my throbbing dick at the best angle I could under the tightly wrapped towel. Then, with my hand gripping the folded towel at my pubic hair, pressing down on my dick to keep it from tenting out, I neglected to remember my shampoo again and cautiously crossed the bathroom to the door. I poked my head out, trying not to look suspicious, and was suddenly very grateful to have been assigned to a room not too far from the head. I trotted quickly to our room, under the guise of being cold.
Once inside, I locked the door and went stupidly to my dresser. I fumbled around with nothing in particular for a minute, but was unable to keep my mind on anything except letting Kurt suck me off. I let go of the towel. It stayed up, but my hard-on was now visible, and a towel normally won't stay wrapped around you for too long, anyway. Kurt had been snapping the gum from the Blow-Pop, but that flavor doesn't last long, either, so he took it out and stuck it onto the bed post. I walked over to the bunks, right in front of Kurt's face, and pretended to be getting something off my bed. I was so completely nervous I thought I would start giggling or something, but my dick knew where it needed to go and was not taking no for an answer. I closed my eyes; the towel was slipping. It unraveled all at once and fell onto the floor.
I knew he was going to let me suck it. We both knew he wanted it so bad ever since he got here. I let him stand there for a second. His dick was as perfect as the rest of him and I wanted to relish the moment watching it bounce around so eagerly for my mouth. I didn't touch him, I just licked the head of his cock, once, to tease him. Serves him right to wait. I certainly did. His leg was twitching like mad. Probably his first time with a guy. I flicked my tongue right under the head to get him ready, even though his cock was telling me he was already more than ready. I swirled my tongue around his head a couple times, and then teased the slit for a little while. He was starting to precum like crazy, and I wanted to taste him. A bead of sweat ran from his chest down his tight stomach, so I licked that up, and then grabbed his dick by the base and started milking him for his load.
I took his seven inches all the way, I had wanted it down my throat for so long that I was almost feverish. I easily fought back the gagging out of pure lust. I had played around with gradeschool friends before and a couple other boys on a vacation or two but this was the first time I had sucked off a real stud like Matt, although recently I had been thinking about it almost continuously. I let him know with my tonsils how grateful I was, and thanked him that way over and over again, getting steadily faster about it. I went down to his pubic hair and stayed there for a second, twisting my mouth around on his dick just enjoying my proximity to his hard abdomen. He smelled great, too, clean from his shower but with a faint musky smell from the new sweat that my sucking him was causing to run down his chest and stomach. He arched his back to feed me his dick deep. I pulled back out to the tip of his hard-on and let my eyes follow the treasure trail up to his fantastic pecs, covered with just the right amount of hair, and then to his face. He was staring down at me, too, but when our eyes met, something changed.
Suddenly he rasped out, "Don't fucking look at me, just suck it," and he grabbed me by the back of the head and shoved his dick all the way in. I gagged from not being prepared and started to choke. This really freaked me out a lot and I got a little scared. I thought about some of these stories I'd heard about guys getting the shit kicked out of them after the "straight" one came and couldn't deal with the fact that it was another guy that had finished them off. I knocked his arms away from my head and stopped. After catching my breath from coughing I said, "um, I don't think this is, uhh, sssuch a good idea," and I moved over a foot from where I'd been sitting on the bunk. This seemed to make him even angrier and he started harrassing me, "What?! What are you fucking talking about 'not a good idea'? I can't fucking believe this." His dick was still as hard as ever, and I think that was part of the problem. But I was getting really uncomfortable and sort of cowering further and further into the bunk. Matt was whispering carefully but his teeth were clenched up and he had this psychotic look on his face as he stared at me. I did my best to avoid his leer. "You're gonna stop? You fucking homo! You've been wanting it this whole time and now you're gonna leave me hanging? I don't fucking think so."
He grabbed my one ankle and pulled me roughly out to the edge of the bunk, then took hold of my arm and spun me around, forcing me face-down onto the bed, with my knees on the floor. Then he ripped my pajama bottoms down, tearing some of the already fragile elastic waistband in the process. I struggled but he had his forearm pressed against my back so it did little good except to make him angrier. I buried my face in the blanket and fought to not start crying like a big baby. I heard him hawk a big wad of spit and let it drop onto his dick. I knew what was going to happen next but my ass was clenched up so much from the fear that I grimaced prematurely. "You're gonna like this, aren't you, Kurt? Yeah, I bet you're gonna like my dick in your ass." He said my name with such disgust. I heard him spit onto his dick again and lube himself up with his hand, then he stuck a finger in his mouth to get it wet.
I felt his finger pressing against my asshole and I winced again. He shoved it up my ass. There was a temporary bit of pain and I couldn't help whimpering for that one moment. Then he started playing around with my ass in an almost sadistic way, with two, then three fingers, each of them too soon, twisting them around and thrusting them deep intome. Thankfully I was able to relax the muscles a little bit. I knew it was for my own good to do so. It was kind of him, I suppose, to loosen me up like that, but then again, I imagine he was more concerned with being able to get his dick in my ass at all than he was with my comfort. Once he could feel that my ass was more ready for him he pulled out, spit again, and pressed the head of his big cock against my hole. "Here we go," I thought to myself and closed my eyes tight. He leaned over and whispered in my ear, "you ready for my dick, faggot?" I didn't answer him. He slowly worked his dick into my ass.
I had never felt pain quite like that before and I started to almost yell. He stopped, but only to cover my mouth with his hand. Panting through my nose, I gradually got used to his size and he released his grip on my face as my ass released its grip on him. "Mmm, you are so tight, baby," he murmured mockingly into my ear. Then he leaned back, grabbed hold of my shoulders tightly with both hands, and started slowly thrusting. After the pain subsided, I was forced to concentrate on the sensation of having this jock's dick inside me and it occurred to me that my own dick was getting hard again. I hated the fact that I was enjoying it, but I couldn't help myself. He was increasing his speed steadily and as I got into his rhythm, I started thrusting my ass back onto him. He laughed a little bit and taunted me, "Yeah, you do like it, don't you?" I spread my knees open more and arched my back so he could fuck me deeper. With one hand he rubbed my chest and started pinching my left nipple, and with the other one he grabbed my shoulder from underneath. "You like my dick in your ass," he whispered in my ear nastily and I thought I would cum without even touching myself. "Mmm, mmm-hmm," I mumbled.
"Say it. Tell me how much you like this dick."
"I like it. I like your dick."
"Tell me how bad you want it."
"I want it so bad." Then all of a sudden, with just the tip of his cock still in my ass, he stopped fucking me. I tried to push back to get more of it, but he wouldn't let me, he would pull away, too. "You want me to fuck your ass?"
"Yeah"
"Say it."
"Fuck my ass."
"Come on, ya little slut. You can do better than that."
"Please, Matt, fuck me hard. I need it. Give me that big cock, please," flattery couldn't hurt and I risked looking over my shoulder at him to plead, "please?" I could feel his sweat dripping onto my back. "Please! Matt." I was whining now. He finally gave in and started again, fucking my ass really hard this time, slamming it all the way in. I arched my back even more for him. I loved the feeling of his balls slapping against mine as he fucked me. His ramming into me made my own dick slap me in the stomach. I was so surprised that, almost as a reward for giving him my virgin ass, he leaned onto me as he slowed down his thrusting and kissed the side of my neck. He started sucking on my neck right under my ear and I moaned. I wasn't scared of him after that. I almost wanted to piss him off a little more if this was going to be my "punishment," but I reconsidered. He reached up and took firm hold of my throat like he wanted to strangle me, and with his other hand reached down and took hold of my dick, which surprised me even more. "Your dick feels so hot, Matt, every inch of it," I told him and he kissed my neck again, this time nibbling on my ear for a second.
The feeling of this stud sliding in and out of me while stroking my dick, combined with his sweaty chest rubbing against my back, I think were what finally did me in. I dropped all my weight onto the bed and closed my eyes, "I'm going to cum," I said in between heavy breaths, "oh, God, I'm cumming." I was grunting loudly enough to maybe put us in danger of being heard but the jock was turning me on so bad I was acting like some kind of animal, grinding my butt up against him. I gripped the blanket with both hands and I came so hard, it seemed to last a full minute. When I came, my ass clenched up real tight around Matt's dick which sent him over the edge. I felt him start to shake and then his cock pulsing inside me. He let out this sort of quick groan and gasped everytime he shot another spurt into my ass. There was something so satisfying about feeling him cum inside me. Although I realize, now that I'm older, that that was incredibly stupid to be unprotected like that, I really liked it at the time.
We both dropped onto the floor next to each other to catch our breath. I couldn't help but giggle to myself, reveling in a post-orgasm high, until I looked over at Matt. He had his hands over his face and was obviously really bothered by the whole thing. I was like, "oh great, now he's going to completely freak out." I started to feel like a piece of garbage and was even considering getting dressed and leaving the room for an hour or two, and then suddenly he shook it off, grinned to himself, and reached over and put his arm around me. It was the most amazing moment. We laid like that for about ten minutes, enjoying the skin and kissing some, but then we realized the floor was extremely uncomfortable and went to our respective beds. A couple of weeks later we sort of fooled around a little bit but it wasn't as exciting as the first time had been, and then a month or so after that Matt's parents moved out of state, took Matt with them, and I never heard from him again. From time to time, I still put on his sweaty jock-strap, though, and jerk-off hard.
Please contact me with comments at spamkings@aol.com...put "Your Story" in the subject box or I'm likely to just delete your letter. If you liked this, then just you wait for the next story, probably titled "Robbery," or something similar, it's going to fuck you UP!