Roxbury College

By Bruce Demosthenes

Published on Jan 11, 2014

Gay

We had compulsory sports every day in private school. But we had choices each season (except for spring where the entire senior school had to run since the fields were too wet for outside sports and the inside facilities were not large enough for the whole school). In the winter I chose swimming. We were bussed to a pool and we basically got to play around in the pool for an hour.

Unlike being at the school, there were no assigned lockers so I got to change near whomever I wanted to. In grade 9 and 14 years old it was 15 year old Clifford who I was lusting after. He was a brunette, so he was different than my usual fixation on blonds, but he was so tall and lanky I couldn't keep my eyes off him. He wore tight multi coloured square leg swim trunks that were like boxerbriefs. Given his height these were perfect on him as they accentuated how tall and slim he was.

Since his swimsuit was so snug, I couldn't make out the details of his cock, or at least I thought that was the problem. I checked him out every chance I could in the pool and would watch him at the lockers every day to try to get a glimpse of his cock but he changed into and out of his swim trunks with his back to me and so quick that no one could see him. He also took a locker at the back of the row near the wall so when he turned away from us he could not be seen.

As he wore black boxerbriefs I also couldn't make out much detail of his cock when his pants were off before he switched them out for swim trunks. Again, I thought the problem was the boxerbriefs.

Finally one day there were no lockers near the wall and he had to take a locker in the middle of the row and I chose one near him. Clifford stripped off his pants and I did too. Then he quickly pulled down his boxerbriefs and I saw his cock!

I had never seen an uncut cock before, but his cock soft at what had to be 3 or 4 inches looked awesome. Maybe it was the foreskin that made it seem big but from that moment on I knew I had to have that cock in my mouth. So turned on was I that I ran to a bathroom stall wearing just my white briefs, went inside and jacked off, running the risk someone would hear what I was doing. But I knew if I didn't I would pop a boner in my swim trunks during swimming.

Most boys in my school were cut so I guess he was shy changing because his cock was different. And I guess I thought I couldn't make out the details of his cock in his swimsuit or boxerbriefs because I was looking for the outline of the cock head and the foreskin completely covered it so in just looked round and with his swimsuit and boxerbriefs being so snug it pressed it almost flat.

To test out my theory, once I changed into my swimtrunks (I wore white speedos) I headed to the pool to check him out. Sure enough, now that I knew what his cock looked like I could see its shape in the swimtrunks. It looked like a 4-5" sausage, though the multicoloured pattern and tight fit had been what had confused me.

Looking up from his crotch I made eye contact with him. He had caught me checking him out. I quickly looked away but I knew I was too late. He knew I had been eyeing his crotch.

After swimming when we went to change, this time Clifford didn't do the rapid switch out of swimtrunks for boxerbriefs. He took his time and took off his swim trunks and, standing there naked, with his uncut cock hanging down between his legs, he folded his swimtrunks and put them in his bag. Then he looked over at me. Of course I couldn't help myself and I was staring at his cock. He had been testing me and I had failed, he had confirmed that I had been checking him out. I tried to look away but I couldn't.

Unlike his usual practice he didn't reach for his boxerbriefs. Instead he reached for his shirt and put it on and did up the buttons. Then he put on his socks, sitting on the bench bareassed, his cock hanging down over the edge of the bench, one sock at a time. With each piece of clothing he would look over at me to see if I was still looking at his cock and sure enough I was, though I made the pretext of dressing myself and of pretending not to be watching. But I couldn't help but look and every time I did he turned and looked and caught me.

Then he stood up and put his boxerbriefs on, and I felt so sad seeing his cock disappear but then he put his hand in his boxerbriefs and positioned his cock. This boy was so sexy.

On went his grey flannels and blazer and not putting on his tie he gathered his bag and went out to the bus.

Nervously, not knowing if he was going to accuse me of being a fag or even beat me up, I finished dressing and headed out to the bus. I walked by Clifford, who was sitting with some of his friends up front, and chose a seat by myself in the very back After the bus had started its trek back to the school, Clifford got up and came to the back of the bus and sat beside me.

Not looking at me but looking straight forward at the rest of the bus he quietly asked "did you like what you saw."

"Yes," I said quietly in response.

"I have keys to the photography lab", he said.

Butterflies were flying around in my stomach. He was proposing a place we could meet. That cock I had just seen for the first time, my first uncut cock ever, was going to be mine, but?.

"My parents pick me up at 6 and we only get back to the school at that time," I said sadly.

"There is no swimming this Friday," he said. True enough, this was a long weekend and so there were no sports after school.

"OK," I said.

"4:30," he said (the time classes ended).

"OK."

Clifford got up and went back to his friends, and I sat there for the rest of the bus ride with a hard-on in my grey flannels. In fact, I had to hide it with my bag and jack off at the school in a bathroom stall for it to go down for my drive home with my parents.

Friday was three days away and I found myself jacking off again and again thinking of his uncut cock. I shot a load when I woke up in the morning onto the briefs I had jacked off into the night before, both times reliving pictures of him changing at the swimming pool. Then, at school, when I would pass him in the hall (we were in the same grade but I was in the enriched class and he was in general so we didn't have classes together thank god) I would find myself starting to get a hard-on so I would have to race to a bathroom stall to jack off at the next break (recess, lunch, free period and before and after swimming).

For his part Clifford was not helping my dilemma. He was now changing for and after swimming in the same methodical (not his usually hurried) way. First off were his pants and underwear and then would come his blazer, tie, shirt and each sock before he pulled on his swim trunks, letting me watch his uncut cock flop around for a good 5 to 10 minutes and then seeing him completely naked this tall beanstock with an equally long trunk. After he put on his swimtrunks and he went to the pool, I went to a bathroom stall to jack off.

Of course I couldn't stare non-stop as there were other boys in the change room. God forbid if anyone saw me checking out his cock. But most boys are shy when changing so I was able to get many looks as Clifford changed.

After swimming was the same. He would take off his trunks and fold them, standing there fully naked as he did. Then he would put on each sock, with his uncut cock laying on the bench or over the edge of the bench between his legs as he did. Then he would stand and put on his shirt, his uncut cock swaying between his legs, the foreskin covering all but the smallest part of the head where his pee slit was. Then, sadly for me, he would put on his boxerbriefs, at which point I would go to a bathroom stall and jack off while the image was fresh in my mind, not caring that jacking off in a bathroom stall off the locker-room I was likely to be caught.

Finally Friday came and I went to the photography lab in the basement of the school. I had never been in it before, as it was not an extracurricular activity I had signed up for (I was in the debate club and was a server in chapel as my two non-sports sign-ups). I knocked.

Clifford opened the door. The room was what you would expect for a darkroom; just a small room with no windows, a shelf with chemicals and a table with pans and some machine that I guessed was to turn negatives into prints.

Clifford closed the door and switched the light from a normal light to a red one, making the room quite dark. I guessed the red light must be so you can see when making prints without damaging them but I didn't ask.

Clifford lay down on the floor and began to undo his pants. Maybe it was because he is taller than me he didn't just have me kneel or maybe he jacks off lying down but I followed his lead and lay down on the floor beside him, just further down so his hips were aligned with my head.

Clifford pushed his pants and his boxerbriefs down to his knees and, without having to be asked, my hand wrapped around his cock. He was still soft and his cock was pointing down between his legs which was the sort of coolness I would expect from him (I had had a boner from the second he opened the door).

I fingered his uncut cock as it thickened in my hand. It got harder and harder in my hand, which I kept wrapped around it, until it was fully erect. It had to be seven inches and, like Clifford, it was slim. Amazingly the foreskin continued to cover most of the head.

I closed my mouth around the head, and gently ran my tongue over and under the foreskin. It was like nothing I had ever pictured (or done) and my approach to his cock was different than to a cut cock, I focused on the foreskin not the head and nibbled and licked.

After while he put his hand on the back of my head and pushed down. I guess that while I was enjoying playing with his foreskin (and he must have been too because he let me do that for probably half an hour), it was not what he needed to get off. So I assumed my usual approach to sucking cock and took his entire 7" into my throat and then backed off so only the head was in my mouth and then back down.

He reached down to the base of his shaft and pulled the skin down so the head was fully exposed and I began my rhythmical deep throating - up and down with my head - on his penis.

His hand (the one not holding the skin down) was still on the back of my head, though it had just been encouraging me not pressing down. That began to change and his hand put a little pressure on my head, not forcing my head down but rather stopping it from moving up as he began to lift his hips off the floor and fuck my face.

I kept my head in the position his hand had suggested and left my throat open as he began to ram upwards into it again and again. Faster and faster his hips would move as he got close to shooting his load into my mouth and throat.

Suddenly he tensed and I could feel his cock spasm as shot after shot of hot jizz hit the back of my throat and, as his hips settled back to the floor, my mouth. His cum was so tasty. It was sweet in both the romantic sense and the sugary flavour. He must eat a lot of candy.

He lifted his hand from the back of my head and I lifted off his cock, giving it some more licks as I cleaned the shaft and head and under the foreskin.

I looked up at him, his cock in my hand, and smiled.

"This is a onetime thing," he said.

My face must have looked crestfallen.

"Hey man, I broke up with my girlfriend two weeks ago," he said (figures he would have a girlfriend as dreamy, good-looking and cool as he was). "I just really needed to cum. Blue balls you know. And hey, you were clearly interested."

Maybe it was because he had just fucked my face so the idea of fucking was in my head, but if this was going to be the only time and his cock, which I had been fingering since he came in my mouth and was still rock hard, I figured in for a dollar in for a dime.

"Can you fuck me in thr ass," I asked.

I really wanted to see what it was like to be fucked and his cock being long and thin seemed like the perfect one to take my cherry.

"That's gross," he said as he scrunched up his face.

"You can do it from behind, you can even think of you ex-girlfriend if you want," I said.

He thought about it for what seemed like the longest time, while I kept stroking his hard cock in encouragement, before saying "OK, what are we going to use for lube".

"We can use spit if you go slowly," I said. I had put my finger in my ass once or twice when jacking off and it had gone in with only my licking it.

"OK," he responded and he immediately spit in his hand and began to rub that over the head of his cock, the shaft of which was still partly wet from his fucking my mouth.

I got up from the floor and took off my pants and underwear and socks and shoes. I too spit on my hand and rubbed it into my hole as I got down on all fours.

Clifford took his pants and underwear, which had been around his knees, and socks and shows off too and got on his knees and moved in behind me.

His cock connected with my hole and he began to push. But push as hard as he could it wouldn't slide into my virgin hole.

"I have an idea," I said.

I reached behind me and took his cock in my hand and pulled the foreskin up over the head, then pushed my hips back and with my fingers I pushed his foreskin just inside the rim of my hole. "Now try".

He pushed and the foreskin acted like a funnel and his cock sliding along its own foreskin breached my hole and his cock went all the way in until his pubes were against my ass crack.

Now on all fours, my navy blazer and tie and shirt still on but naked from the waist down, with Clifford behind me also wearing the upper half of his school uniform, I settled in to be fucked.

Clifford took hold of my hips and began to fuck me, moving his cock out to just the tip and in until his hips hit my ass, again and again. The sound of our flesh making contact when he rammed into me was so loud in that tiny dark room I thought the whole school could hear.

I guess because he had already cum once or maybe it was because he wasn't into guys but he fucked me for what must have been an hour before he came. I didn't care. His long thin uncut cock hit all the right places. In fact, having been so boned while sucking him, I shot a load on the darkroom floor shortly after he got his cock going rhythmically in and out of my ass. And I stayed hard and came a second time in like the middle of the hour before he began to really began to fuck me hard.

Clifford's hands on my hips squeezed harder as his pace increased. I braced myself as he seriously began to plow my ass, ramming me again and again, his hips loudly slapping my ass cheeks as his balls hit the back of mine and his cock hit deep inside my ass (if I knew anything about biology at this age I would have realized his long thin cock was connecting with my prostate which is why I came as soon as he started fucking me, stayed hard and came a second time mid-session and was now about to cum again).

I could feel Clifford tense like he had when he came in my mouth, just as he gave one hard thrust and buried his cock all the way into my ass. That made me cum a third time onto the dark room floor just as his cock was unloading deep inside my ass.

We stayed like that for a few minutes, me on all fours, his cock all the way inside me and his hand holding my hips firmly close to him so our bodies were pressing against each other at my ass. In fact, we stayed like that so long I could feel his cock softening in my ass. It still felt amazing and it surprisingly made me continue to be hard, even though I had shot three loads. Finally he pulled out.

We both got up and began to reach for our clothes. Both of our cocks were soft now and my cut cock looked so puny compared to his uncut cock which literally swayed between his legs as he put on his socks. Sadly it disappeared into his boxerbriefs and then grey trousers.

We passed each other in the hallway and nodded 'hello' and, for the next few weeks until the fields were hard enough for summer sports, we continued to change next to each other at swimming. Clifford was nice enough to take extra-long time changing without pants and underwear so I could look at his uncut cock.

I guess he had always been in hurry to change because being uncut and different from the rest of us he felt self-conscious. I like to think that once he discovered me worshiping his cock it made him more confident. But really I didn't give it much thought. I was too busy watching his uncut cock sway around and then running to a bathroom stall to jack off so I could finish changing and not miss the bus.

We only spoke once before the end of the year. I was in the common room waiting until it was time to be picked up by my parents and Clifford came in. As there was no one else around he came over and sat down next to me.

"You know the assistant headmaster made me clean the darkroom from top to bottom," he said conspiratorially after moving his chair very close to me. "The ass head said the janitorial staff complained that a large amount of chemicals had been spilt on the floor."

Grinning, I said "you should take that as a compliment."

He grinned back.

"We could make another mess any time you want," I said.

"Nah, I got back with my girlfriend shortly after we? you know? so I'm good," he said before playfully hitting me on the back and saying "you take care" and walking away.

He really was incredibly cool.

That night I jacked off, not thinking about seeing him in the lockeroom, or sucking him or him fucking me, I came thinking about him patting me on the back, grinning with me over our secret and saying "take care".

At the end of grade 8 Clifford convinced his parents to take him out of private school He had a girlfriend and it made sense he would want to go to school with her. I was just sorry that I couldn't watch him change.

For my part, I had no desire to leave private school. The showers and bathrooms open into locker-room, changing with other boys 16 times a week, no distraction of girls. That would all change with my parent's divorce.

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Next: Chapter 4


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