I was 16 in grade 11, and I found myself back in private school, this time as a boarder.
I didn't want to become a boarder. But my mother couldn't find work in Ottawa and the only solution was to put me in residence. I was terrified; not knowing what life would be like.
The first night, after having been shown around by one of the teachers and having settled into my new room, I headed off to the washroom. There, to my surprise, was one of my classmates, Abby, taking a shower, naked.
We were all supposed to take showers after sports and gym, but nobody did; at least none of the day boys did. Boarders on the other hand seemed to shower together regularly and think nothing of it.
On the lower flat, which includes all boys from grade 9 through 11, there were two showers. One was a large communal shower that had a dozen shower heads around the outside of the relatively large tiled room. This was mostly used by the younger boys as it was on the new half of the floor which is where their bedrooms were. In the older half, where us grade 11s were housed, there was a bathroom that had three shower heads side-by-side and, across from that, two toilet stalls, one urinal and a sink. At the opposite end of the door to the hall that ran through the flat, which was never closed, was the radiator, like the one that we had in each of our rooms for heat throughout the older part of the school. There were no curtains or dividers separating the showers from each other or the showers from the rest of the small bathroom.
So as I headed into one of the toilet stalls, Abby, standing there naked under one of the showerheads joked that I was about to experience the nightmare of boarding life for the first-time, using a toilet with no privacy. He wasn't wrong. Once he pointed out I had no privacy I couldn't go. But I also couldn't go because I had just seen Abby naked.
Abby was a little older than me, but by this grade age had become unimportant and he was probably only older than me by a matter of months. Where I stood now about 5' 8 ?", still with brown hair but with a growing patch of hair on my chest and under my arms and my pubes had fully filled out; Abby was blond and an inch or two taller than me, with what most people call a swimmers build (wider shoulders and slim hips) but, as he was the quarterback of the junior team, I always thought of it as a quarterback's build (long legs and firm ass due to his running, long arms and strong shoulders for throwing, but lean for speed and not bulky for blocking).
As for our genitals, my big balls meant I filled out my briefs nicely, which were still classic white as up until this point in my life my mother still bought my clothes, though my cock was pretty average at less than 6". Looking at Abby in the shower for the first time, his cock seemed to hang down longer than mine soft, but not by much, settled nicely into what was a proportional sack for his cock. I figured we were similar in size when hard, but there was no way to know. Being blond, Abby had hair under his arms and a full set of pubes, but nothing on his firm slim upper body.
While I didn't feel comfortable yet as a boarder, on this my first night I had seen one of the hottest boys in school naked, something I jacked off to that night careful not to shake the bunk bed and thus wake my new roommate (who turned out to also be tall and slim, with curly blond hair, someone who I had never met before becoming a boarder because he pretty much stuck to himself). I was definitely going to like being a boarder.
I didn't make friends with any of the boarders in my grade having only become a boarder mid-year. Boarders and dayboys don't mix and I was in the enriched class and there were no boarders in that class (probably cause to really excel in academics you need your parents standing over you forcing you to do your homework and boarders are left on their own to do 'prep' - and the busy life of living on a dorm with other boys means school work suffered even when the rules said no talking during prep).
Not having boarder briefs in my own grade, I ended up becoming friends with other boarders who were in younger grades, most of whom I became friends with because of where I ended up sitting at breakfast, lunch and dinner.
Since there were no seats in the senior school available for lunch when I became a boarder, I ended up sitting with grade 8s in the junior school at lunch. At dinner I sat with grade 9s, and my best friend became my lunch seatmate, Stephane. Stef was skinny, and French (so didn't have many friends of his own) and, being in grade 9, was probably 14. We just migrated to one another. OK, to be honest, I probably migrated to him cause he was hot, with dirty blond hair and blue eyes and an incredibly mince physique. Opposites attract and I had always been attracted to skinny blond boys.
As the year went on and we became friends we spent lots of time talking. One of the things we talked about was what experiences we had in life. I had never been drunk. Stef had, thanks to his older brothers living in a rural town in northern Quebec. For his part, he had never had tried sex with a boy, something I admitted I had done, though was (thankfully) never asked by him to elaborate. We made a pact that we would introduce each other to what we had tried.
I ended up, being a good student (and the only boarder from our enriched class, though admittedly my grades began to drop once I became a boarder) being called on to do stuff around school that involved responsibility. For example, I was asked to be an altar boy in the chapel and soon became head altar boy.
I was also a student librarian. As a librarian, I would unlock the library at the bigging of prep, sit at the desk and sign books out when students needed them, make sure that the boys who came to the library had a permission slip and then lock the library up after the time set aside for homework was done for all the grades.
Well into the year Stef scored us, from one of the older students, a bottle of rum. Ironically, given where I had lost my virginity, Stef was into photography so we ended up drinking it in the photography lab, and I ended up spending the night puking my guts out in a toilet in the locker-room. It was a Friday and, fortunately for us, only a prefect was on duty, not a teacher (prefects were grade 13 boys who the school trusted and had been placed in authority, and they wore red jackets to denote their rank). Stef was able to convince this prefect to turn a blind eye and, after babysitting me in the locker-room and me getting the liquor out of my system, few were the wiser (I say few because there are no secrets in a boarding school for long). I have never been able to drink rum since.
Him having fulfilled his promise to me, I knew I should return the favour, but he never mentioned it and it was not like it was something I was going to propose given his clearly strict Catholic background (in one of our talks he told me he didn't ever jack off because he had been taught that it was a sin).
But on one school night weeks later, I was on library duty. I had forged a permission slip for Stef so he could join me during prep (as he was only in grade 9 he was supposed to do his homework in a classroom with all the other grade 9s and 10s supervised by one of the teachers who lived on the school grounds).
After prep was done I instructed all the students to leave the library, which they did with some coaxing. And then I locked the door. Stef had scored a mickey of scotch from his contact in one of the higher grades and he and I set about drinking it. It didn't take much, us being neophytes, and we were tipsy.
Being drunk, I ended up on the couch stretched out and Stef ended up on the same couch. He stretched out at his end and his leg came to rest draped over my body, with his foot down around my crotch. Instinct took over and my hand reached up to above my head where his crotch was, and I placed it on the fly of his grey flannel trousers. As my hand touched his hardening cock through the soft material, his foot moved up and down against my now hard cock in my own grey flannel trousers.
Encouraged by his response, I undid his belt and his pants and then pulled down the front of his dark brown briefs. Still using my hands above my head, I took out his hard cock and began to stroke it, all the while his foot rubbed against my hard cock.
I slid onto the floor and brought myself so I was kneeling next to the couch. I was stroking his hard cock and looking at it as he lay there with his eyes clothes, stretched out lankily on the coach.
I started to think about pulling his pants down so I could get to his balls but then he began to cum. It sort of oozed out like lava down the side of a mountain.
Quickly I put my mouth on the lead of his cock and caught most of it in my mouth. When he stopped cumming, he gently lifted my head off his cock, did up his pants and said he had to go, leaving me there on my knees next to the couch when he exited the library.
I undid my pants and stroked one off while the experience was still fresh in my mind. I did up my pants with my load filling my briefs, but with nothing to clean myself up with I had no choice. I only hoped my roommate didn't notice when I undressed for bed.
The next day it all seemed like a dream so part of me doubted it had happened. What is more, I couldn't find him anywhere. It was several days before I found him and it became clear he was upset. I got him to go into the photography lab to discuss it where we would have privacy and he explained he thought what we had done was wrong and he blamed me for having taken advantage of him. The fact that we had talked about it in advance and that his foot had encouraged me paled in light of the fact I had put his cock in my mouth.
Maybe if I had just let him cum on his stomach he would have forgiven me or I could have explained away what had happened. But I had taking his cockhead into my mouth and I had swallowed his cum. So there was no way he was going to forgive me or believe it was 'just the alcohol'. Then again, I got to taste his cum which is something no other boy on the planet will ever get to do. So, while it broke my heart I had lost my best friend, I tried to convince myself it was a fair trade.
Our friendship was over but this would lead to a new chapter with my roommate. It seemed that he had been curious when I shoed everyone out of the library (including him) and yet Stephane stay. And he has seen the cum in my pubes when I had undressed that night for bed, or at least seen something glistening in the dim light of our room that he had become curious. So when he had seen us go off all serious to talk, he had followed and listened outside of the photography lab.
I wasn't particularly close to my roommate, Ian. He was introverted and I was extroverted (which is why the headmaster had put us together, thinking I would be a good influence on him). But he had blond curly hair and was skinny so while we barely spoke I did watch him undress each night and dress each morning.
He was tall, probably 5'10" already, even though he was only 16, had a smooth chest and was lanky. He was not into sports, kept to himself and, as I discovered shortly after we began rooming together, had an uncut cock (which was rare in this era in Canada).
Our room was in the old section with the other grade 11s, but we were down a hall and pretty much isolated. So that night after I had lost my friend Stephane, when we got in bed (I slept on the top bunk him on the bottom), knowing we would not be overheard, Ian said bluntly "so you like sucking cock".
"I don't know what you are talking about," I said defensively.
"I heard you and that grade 9 kid talking in the photography lab and I know what happened in the library."
I was floored. I didn't know what to say, though I did know I didn't want word of this getting out. As I have mentioned, being classified as gay is the worst thing that can happen in a boarding school. And knowing how upset Stephane was about what had happened, if word go out I knew he would cast me under the bus or worse, make it his mission to make everyone hate me and believe I had molested him.
"What do you want," I asked quietly.
I could almost hear him smile in the dark. "Nothing much," he said, "figured you would rather suck me than me than us pretending the other was asleep when we jack off."
"OK," I said.
I don't know what I was feeling. Maybe I felt resigned because I had no choice. But I also had checked him out changing and I did think he was hot k. And it was not like I didn't like sucking cock, especially an uncut one.
"Every night," I asked.
Ian laughed and said "jeeze, you are a horn dog. Nah, I know you jack off every night but I only do it once or twice a week."
I guess my thinking I was not shaking the bed had been delusional.
"So I guess you will let me know," I said.
"Well you can start now," he replied matter-of-factly.
I climbed out of my bunk, naked (which is how I had been sleeping since I was 13 and I had not seen it necessary to change my habits when I went into residence, even though there is no privacy). In contrast, Ian wore pyjamas, which he always put on over his white y-front briefs, so pulling back his sheets and blankets I pulled down his pj bottoms and his briefs, exposing his hard cock.
Normally I would have spent time licking and sniffing him through his briefs, but this was a job he was making me do, and I wanted it over and done with. Having said that, my hard cock which was visible to Ian in our room which was dimly lit from the school lights outside, told a different story.
I went to work on his foreskin, nibbling and licking it. [Ok, it was a job that I was going to enjoy doing.]
His cock was long and thin, and it reminded me of Clifford's. It had to be about 7" long and the foreskin also stayed over the head.
I couldn't help myself and worked for a while on the foreskin, running my tongue under it and over it, enjoying the feel of this loose skin in my mouth.
Once I grew bored with nibbling on his foreskin I quickly used my skills and took his cock all the way down my throat. He clearly had never experienced anything like it because he was moaning in seconds and shooting his load deep into my throat shortly thereafter.
Once he had stopped cumming, I grabbed my briefs from the day and climbed back onto the top bunk and, now not caring about shaking the bed, jacked off onto my briefs moaning loudly while he lay beneath me. I assumed he had pulled up his pjs and briefs and was under the covers when I came on my briefs.
I actually felt much better. I may have lost Stephane was a friend but I had just bonded with my roommate in a way I had never expected and had an uncut cock that, based on that night's first experience, would deliver a big load in the privacy of our room.
Over the course of the rest of the school year, which was only three months as my escapade with Stephane had happened well into the year (my only having become a boarder mid-year), I sucked off Ian twice a week, always on a night of his choosing.
We never really spoke about it, and outside of our room we actually began to spend time together and it turned out he was a really nice guy. In our room, on the nights he wanted to be sucked off, instead putting on his pjs over his briefs, he would take off his briefs and climb into bed naked.
He didn't have to ask, it was obvious what he wanted, and I would end up kneeling next to his bed sucking his uncut cock. It never took him that long to cum once I started deep throating him, though the length of time I spent on foreplay (i.e. nibbling on his foreskin) would vary based on how horny I was.
After a couple weeks he suggested when I went to get back up into my bunk that I finish myself off down there, so I jacked off onto my briefs kneeling next to his bunk while he watched (and while I watched his softening uncut cock, which he left exposed with the blankets back).
To my surprise, one night as I was sucking him I felt his hand wrap around my hard cock, and he stroked me off while I sucked him. From then on, this he did every time I sucked him, until the end of the school year. At prize day we parted company and he never returned to the school.
I am sure when the headmaster thought I would make Ian more open to making friends that he never imagined that Ian and I would end up fooling around. Then again, an uncut cock does look like the head of a turtle so I was just doing literally what he had suggested to my mom, that I get Ian to "come out of his shell".
For his part, Ian helped me get over Stephane. And, where I had not enjoyed rooming with him until that point - rooming with what I thought was an introverted moody boy - I came to love him in my own way, enjoying his company during the day when we would see each other in the common room between classes, and I definitely loved his cock in my mouth and his hand on my cock at night.
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