My story with Brian only started-up again in grade 12. While I came back to private school in grade 11, this time as a boarder, his and my worlds were quite different.
In fact, the only time I crossed paths with Brian in all of grade 11 was during a debating tournament that our school was hosting. Kids in my class were asked to be judges and Brian's mother, who was on the board of governors of the school, arranged to have us over for a light dinner at the end of the tournament. Only six of us who were all from the same class made it to Brian's for dinner, which was fun because it was like old times. Brian had definitely moved away from those of us who were in class towards his fellow sports jocks, most of him were in the general stream. But in the safety of his home he relaxed and we joked about nerdy things like we had since junior school.
At one point during desert, which was Jello, Brian even grabbed Wayne's (who was also a judge) crotch and Wayne jumped up and ran out of the room and Brian went running after him and everyone was running around and it was like being back in grade 8 or 9 again. Of course, having actually had sex with Brian, I wasn't running around. I stayed at the dinning room table and finished my Jello (crotch grabbing, while I lived for it in grade 8, was a poor substitute for having sex, and that wasn't going to happen that night with Brian, if ever again).
Other than that night, when Brian was once again the youngest kid in our class and a fellow brainiac, Brian pretty much ignored everyone in our class and outside of class he hung with the other jocks, especially the sports stars in the older grades.
To complicated matters, boarders and day-boys don't mix. And I was now a boarder.
Being a day-boy is about going to school like any other high school, albeit with a school uniform, a very structured curriculum and compulsory sports every day, but it still ran from 9am until you went home for dinner (which was a slight change from public school in that you didn't leave often until 6pm due to sports). Then you went home to your parents, and brothers and sisters if you had them, and even friends from your own neighbourhood, if you still had them from before you were sent to private school.
Being a boarder became your entire life and evening on the flats and in your rooms with your roommates and your three meals in the dinning room with the boys you shared a 9-person table with (eight plus a prefect at the head in the senior school to ensure discipline) became as much part of your life as any of your classes.
Younger grades did homework (or prep) in a classroom by year. But in grade 11 you did it in your room. Not surprising, being a boarder took a toll on my marks, which was why there were no boarders in the enriched program (aside from me who had gotten there when I still had parents who stood over me and forced me to do my homework). Boarding life was very social and other boarders, who lived and understood the unique way of life, because your main friends.
After all, were with them day and night seven days a week. So you went downtown with your friends and the weekend. On long weekends, when most boarders went home, those of us who didn't bonded even closer because we were the few left in an otherwise deserted school. My world had changed.
Brian and I had not really been in the same circles back in grade 10 when I was a day-boy, as his sports were football and hockey and mine were swimming and soccer. It seemed, based on all his talk in the locker-room that he had also, outside of school while I was away, taken up rock climbing that now was his passion.
We were both still in the enriched program together, but as high school went on, jocks like Brian migrated to their sports teams more than to their academic classmates (though less so than boys do in public school where you can actually choose between doing sports or academics and drop the other almost entirely - in private schools everyone had to do well in both).
Where things changed in Grade 12 is that some of our enriched class began to study for the International Baccalaureate program. As there were too few in our class to teach as a full class, the school teamed up with the all-girls school down the road and those of us in the IB program began to share classes for the subject on which we were going to write one of the international exams.
The irony of this was that the nerdy boys got to go to the girls school for classes and we had girls in our classes back at our school. Making us the envy of the less academic jocks as we were the ones with close female friends at the girls school which for most boys seemed just out of reach. Dances became a lot more fun for us as when the girls were brought over we were the ones who had female friends to dance and talk to while some of the cool jocks were left like wallflowers on the sidelines.
How this impacted on my life is once again I found myself sitting next to Brian in a classroom, whenever we went to the girls-school for IB English, the one IB exam Brian and I were taking together. And I began to write notes to in his notebook during class when the teacher wasn't looking, the way I had done back in grade 10 that led to that fateful night. Though this time they were not about sex (at least in the beginning).
I had thought about that night many times, and about having his big cock in my ass. I pictured him fucking me face down on the bed and I would go to sleep remembering him asleep on top of me, soft in my ass but still filling me like no other cock ever had. I never had I felt so complete. I wanted nothing more than to have him inside me again.
A first few notes I wrote in his notebook in class were me asking if I could come over and his wanting to know why. Two years is a long time and the last thing I was going to do was to mention that night, having no way of knowing how he would react. Certainly in the locker-room and around the school he was all about girls and even back when he fucked me I knew he would never countenance any suggestion that he was gay. So I made a pretext about being interested in learning how to rock climb.
After several weeks of pestering him about it in class, he eventually agreed I could come over. As a boarder I was not allowed off of school grounds, but I decided to risk it and skip sports and that would give me from 4:30 until dinner at 6. Brian lived about 5 minutes from the school and he, as a star athlete and a day-boy whose mother was on the board, could skip sports and no one would think twice. So we agreed I would come over right after school.
Arriving at his house, after ringing his doorbell, Brian took me up to the attic. His was a huge mansion and it seemed that the attic, which frankly was more of a complete floor in any house or apartment I had lived in, he had to himself. In the attic there were two bedrooms, a central living area and its own washroom with shower. He lived in the attic by himself. His older brother who had lived in the other room had gone off to college and his younger brother lived on the second floor where his now widowed mother had her master-bedroom. And I had seen the ground floor when I had come over with the other judges in our grade 11 debating tournament (which was huge with dining room, den, living room and a large room for entertaining and dancing).
In grade 12 I was 17, brown hair and about 5'9 ?" with a small patch of hair on my chest, a treasure trail down to my pubes and a 6" (when hard) cut cock and rather ample balls (my cock was average based on my classmates in the locker-room but thanks to my balls I always looked like I had something to brag about when I was wearing pants (my fellow boarders who had all seen me in the showers knew differently).
Brian was still the youngest in our class, but at 16years old this blond Adonis was at least 5'10 ?" or 11", smooth except for under his arms and his pubes where his sandy blond hair was noticeable and framed what looked like in the locker-room to be when soft 6", I could only guess how big it was now hard two years after he fucked me so mercilessly.
Brian got out his climbing gear and proceeded to show my how the harness worked. He proposed we go nearby to a small rock face for my first time, that was only 10 feet off th ground, but I had no interest in climbing. I kept asking about the harness, and when he put it on and I began reaching for it and commenting about how it must feel pulling up on his crotch when he climbed, he said "you didn't come here to learn how to climb, did you."
"No," I replied, because the thought of actually going climbing was unappealing to me, even if it was a means to an end, and at this stage we were in his room and no one was home.
"Why did you come here," he asked.
I looked at him incredulously, but he seemed to genuinely not know why I would have come.
"I thought we could so stuff like we used to," I said. And when he didn't respond I added "I thought we could have Jello."
Brian looked genuinely upset. I didn't know if he was disappointed because he really wanted to go rock-climbing or was no longer into what we had done. He just took off his climbing harness and disappeared downstairs without saying a word.
I stood there in the attic living-room for a long while, wondering if he was going to come back, when suddenly Brian came up the stairs wearing only a pair of low-rise brown briefs. The same briefs he used to wear when we were in grade 10 (though I had noted in the locker-room over the last year that Brian now wore all sorts of different colours and brands, in fact almost a different brand and colour every day).
Brian passed me without speaking and went into his bedroom and I followed like a puppy dog. He sat in a chair across from the bed and I sat down on the bed.
Brian stretched out his legs and began admire his body and how he looked in those briefs. To say he filled them out would be an understatement.
I was rock hard already in my pants, but Brian just reclined and rubbed his thighs and looked from his crotch to me and back again.
"Impressive isn't it," he said, looking at his cock which was only now starting to harden in his briefs. His waistband of his briefs had to be an inch or two out from his stomach as his cock, which was still pointing down in those briefs, was pushing the cotton away from his body as it strained to be free.
"These briefs can't hold it," he said, reaching into his underwear and adjusting his cock so it was free from the material. It had to be 7 or 8" above the waistband, which meant it was probably 9 or 10" in total. And it was thick. It had to be over an inch across.
"Is this what you came for," he said, knowing it was.
I nodded; a lump in my throat preventing me from speaking and why it was what I had come for, it was just so big that I didn't think I could take it. I took him when I was 15 years old, but he was only about 8" back then and not nearly as thick. He was a 14 year old boy with a huge cock for his age, but still a boy and now at 16 he was pretty much a man with a man-size - a very large man-sized - cock.
Brian got up and came over and sat next to me on the bed.
"You told people able the Jello," Brian said, with a touch of anger in his voice, once he was sitting next to me.
I turned bright red. It was true. After we had been at his place for the judges get-together I had mentioned it in school the next day, though Wayne and the other boys denied anything happened. I guess it was my way of deflecting my feelings towards him or maybe it was wanting to share, if they talked about what had happened the night before and weren't put off I could brag that a year and a half earlier he and eye had fooled around (I would never admit what specifically we had done).
I guess mainly it was my feeling dejected because why I liked seeing Brian running around and being a kid like we used to be, it wasn't with me and I wanted him so badly. The night he had brutally fucked my ass without any regard for my feelings and the pain made me want him. He stole part of me that day and, I knew, for the rest of my life I would want that cock inside me again.
"I am sorry," I said, with genuine sadness in my voice.
Had he come up the stairs in those same briefs and was now sitting next to me with his hard cock sticking out of those briefs just to remind me of that night and then to tell me it would never happen again because I had betrayed him?
Looking down at his hard cock sticking above his briefs Brian said, after a long while, in a very quiet voice, "you have to make the first move so if you tell anyone I will tell them you grabbed my cock and that you are the fag who came onto me."
I didn't have to be asked twice. I wanted that cock and my hand went out immediately and wrapped around that huge thick shaft.
"What do you want to do," he asked.
"How about 69," I asked.
"I can't 69 with you. You are too short," he said, and then added with almost a sneer, "and you're too fat, I could never reach your cock".
I was not fat, though admittedly I was not the toned athlete stud he was. And even though I was 17 and perhaps not all of my baby fat had disappeared as I had not had a growth spurt that other boys had by then, I was firm, just not skinny like him. I didn't understand why he was being so mean, except I did tell boys in our class he has grabbed Wayne's crotch. But no one believed me anyway.
Brian reached for one of the penthouse forums that were strewn around the floor, opened it to a story and handed it to me. I read the story, holding the book in one hand as my other stayed wrapped around his hard cock.
"I want to do that," he said.
It was a complicated story involving a threesome (two guys and a girl) and they took turns with each other, first each guy fucked the girl and then the guys took turns fucking each other while the girl watched and then each of the guys took a different hole on the girl and they all collapsed ontop of each other.
Confused, I asked how we could do that without a girl, and said "well not everything obviously." I got his point, as part of the story involved the guy fucking it was clear he was saying he wanted to do anal.
As the guys took turns doing each other I naively asked "do I do you first or you do me first?"
"I am not letting you fuck me," he said. "I rock climb and that would affect it, and it makes you walk funny and no one can know you and I ever - ever in the past and never again in the future if you open your big mouth again - have been together."
The walking funny was a strange argument to use for why couldn't fuck him given he was trying to convince me to let him fuck me with an enormous cock. While I didn't rock climb I didn't want to walk funny. But having been fucked before, including roughly by him, I knew you didn't end up walking funny so he clearly was just trying to push my buttons to see how much I would put up with.
The answer is a lot and I simply said "do you have any thing for lubricant?"
Leaving the bedroom Brian came back shortly with some lotion and I got undressed as he lay on his bed (a twin bed) and removed his briefs, I removed the last of my clothing and began to put lotion on my hole. He did the same to his hard cock.
Climbing up on the bed, I straddled him with my knees, facing him, and lowered my ass so it lined up with his cock which he was holding straight up.
I leaned back and his cock head connected with my hole. I used my weight to push down and slowly his cock began to enter my hole. Barely had the head gotten past my anus then his hands were on my hips and he was pushing me down.
Taking deep breaths I ignored the pain as that cock steadily entered me. It worked its way all the way into me as he pressed my hips down on him.
The pain was intense, but I didn't complain or cry out or hesitate. Soon I was sitting on his lap, his hard cock all the way inside me, my balls resting on his pubes.
"I didn't think you would be able to take it," he said, sounding almost impressed.
I didn't tell him it hurt like hell and that I had wanted to cry out all the while it was going into me. In fact, I didn't say anything, figuring my voice would crack and betray that I was in pain and not as comfortable with this as I was pretending. So I just sat on his lap, his cock all the way inside me, waiting for the pain to subside.
"After that first time," he continued without seeming to notice I was not responding, "I didn't think you would ever want to be fucked again."
So he knew he had basically raped me and that I was in pain that night as he pounded my ass lying face down on the bed. Did that turn him on? Did he regret it? Was he testing me now?
"I knew you wanted my cock all during grade 10" he continued. It was true I looked every time he flashed me his cock at my locker, and it was true when he stayed over I wanted to touch it, but I had never thought about him fucking me until he actually started to do that and at that point I wanted him to stop because it hurt so bad.
Not wanting to give him the satisfaction of knowing he hurt me that night or was hurting me now, I reached behind myself and began to play with his testicles, and felt where his shaft disappeared into my hole with one hand. The other went over his stomach and chest.
"So I did you a favour when I took your cherry," said Brian smugly. The reflecting he added, "if it was your cherry, you will have to tell me the truth sometime but not now, I need to get off and that is what your round ass is for and will be for the rest of our time in school together."
Brian closed his eyes and let himself enjoy my hands running over his body and playing with his balls, and he must have been enjoying my tight ass wrapped so snuggly around his cock. When he had said I was going to be doing this repeatedly until we graduated in grade 13, my cock had pulsed and I knew I wanted this. Any pain I was feeling began to melt away.
After a while Brian, without opening his eyes, said "are you just going to sit there or are you going to ride me".
Leaning forward I rested the palms of both hands on either side of his head and I began to lift my ass off of his cock and sit back down.
First I did this slowly, lifting off until only the head was inside and then using my weight to sit down hard.
But soon I was in a steady rhythm.
I was leaning forward now as I rode up and down, so he must have felt my breath on his face, but he made no move to kiss me or open his eyes so I just kept riding up and down, looking at his gorgeous face with his eyes closed, my breath getting faster and deeper with each time I lowered my ass onto his cock.
Before long I was panting and I knew I was about to cum. I couldn't stop myself and I rode him harder. I was moaning. My ass was slamming down on his cock and without wanting to I began to shoot all over his chest and stomach. I even hit him in the face.
I don't know if it was my soaking him with cum or my ass contracting on his cock but he grabbed my hips and pushed me down hard and held me there and I could feel his huge cock pulsing in my ass. He was unloading deep inside me.
I stayed like that, leaning over him with my ass pressed against his hips and his thick cock buried all the way in my ass until he let go of my hips.
I climbed off him and was going to go get a towel when I heard, "get back here and clean me off."
"I was going to get a towel," I said.
"You have a tongue," he snapped back.
I had never had a desire to taste my own cum, so had never tried it, but I loved other boy's cum. Further, his cock had been in my ass and I don't know if I wanted to taste that. But something in the way he had ordered me back and said to use my tongue that I felt compelled to begin to lick him clean.
First I licked off all my cum, from his face down his chest to his stomach, which was just soaked (I had cum a lot).
By then he was waving his soft but still huge cock around my face so I took that into my mouth and licked and sucked it clean.
When he decided he was clean enough, he pushed me off his cock and said "get your clothes and get out of my house."
I grabbed my clothes, putting them on as I ran through the attic living-room and down the stairs.
On the way back to school and all through dinner I thought I could feel his cum leaking out of my ass. His cock having been in there certainly was all I could think of during prep and into the night as I tried to fall asleep.
When I took my briefs off that night I could see a stain of his cum and even some blood on the back of my briefs. I decided that night I would have to go shopping for coloured underwear. As a boarder I did my own laundry and while my mom bought me white briefs claiming to use bleach I didn't use bleach and I never did laundry alone. A group of us boarders would make the trek down the hill to a laundrymat and the last thing I wanted was anyone to notice a stain like this, assuming Brian was serious about planning to fuck me again. I hoped he would, again and again.
The next day my ass was sore, and I was sure in the shower that morning the other boys could see how red and stretched it was, but no one said anything.
And as I walked between classes I wondered if I was walking funny. Maybe Brian was right. Or maybe he had just been fucking with me, well fucking with my brain in addition to my ass which he had done in the literal sense.
Brian made a point of sitting in between other people during IB English so I didn't get to exchange notes or talk to him for the next couple weeks. But during those weeks I jacked off every morning and every night trying to recall how it felt to have his big cock inside me - knowing I had to have it again.
If I thought I was his the first night he had forced himself on me, then now that I had given myself willingly to him there could be no doubt. From now on I would do whatever he told me to do.
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