In the middle of grade 10 my parents divorced and I moved with my mother to a small town in Nova Scotia [Canada].
Small towns are tough, because everyone knows everyone and I was an outsider. I was entering school midyear so even if it wasn't a small town it would have been hard to form connections. And worse, I was from the most populous province of Canada [Ontario] so for most I was the enemy.
I didn't really make any friends. But, I still found images to jack off over because we had gym, though sadly only 3 times a week.
In the locker-room the boys would all talk about their conquests with girls. They were all 16, so maybe some of the stories were true and they had girlfriends. But it was a small town and I rarely saw anyone in my class with a girl. Then again, I never socialized with anyone outside of school.
I got up in the morning and went to school. Went home at lunch and came home after school. I had no social live. My mother worked so I was home a lot of the time on my own. So between TV and jacking off I pretty much filled my days when I wasn't doing homework or in school.
The coolest boy in my grade was Murray. He never told stories in the locker-room but he was one of the few boys in my class I always saw with girls. I assumed one of them had to be his girlfriend and I knew if anyone was having sex it was him.
The biggest story teller was Larry, a talk bean stalk kid who would brag about his supposed conquest from that weekend in the locker-room every Monday. I remember one day when we were changing he regaled everyone about his weekend experience where some girl had been so eager for sex she undid his jeans with her teeth. While that was something I would undoubtedly do, I doubted it happened to Larry. And when I looked over at Murray he was listening but had a smile on his face that said "you're full of shit".
I was 15 years old in grade 10, having skipped a year. I was about 5'7" and had brown hair, and some of that hair was becoming visible on my chest (only a little patch of a few hairs) and a little more under my arms. I had a more noticeable treasure trail that ran from my bellybutton down to my pubes which had begun to fill in nicely. Under those pubes I had what was a 5" or 5 ?" cut cock. I had good size balls, so I filled in a pair of jeans nicely, but my cock was pretty average for my age.
Of course everyone else in my class was 16, so they probably had slightly bigger cocks. Though when soft, looking at the other boys in their briefs (everyone seemed to wear briefs in this era and age group), we all seemed to be about the same size. Probably about 2" soft. How big they got when hard I figured I would never know. I barely talked to anyone, so the chances of fooling around with someone was nil.
Murray was slightly taller than me, also with brown hear like mine, but his build was more muscular. He was 16 so he wasn't 'built' but he had the body of a natural athlete, which from what I heard he was. I didn't hang around the school and sports weren't compulsory, but I knew he was quarterback of the junior football team. And damn did he fill out the letterman's jack well.
He was confident, not arrogant. He was built but not stocky or overly muscular. He was naturally fit and with sports his body was getting defined (certainly as defined as a 16 year old can be).
I was used to joining extracurricular activities from my time at private school so, being very lonely and at my mother's suggestion, I signed up for curling during the winter. It was every Saturday afternoon. Imagine my surprise when I showed up and who should also be there for curling, Murray.
We didn't talk much, even as co-members of a four person curling team. In school he was part of the school's elite, surrounded by other sports stars and cheerleaders, whereas I was an outsider who didn't fit into any clique (even a clique like nerds that the jocks would look down on).
In curling we didn't talk much not because of school barriers but because he was not a talkative guy. He just became our skipper without anyone discussing it because no one questioned that it should be any other way. He exuded athleticism. And it turns out he was good at curling and, as we learned the game, we became good as a team during the winter months.
Between gym at school and curling, I got to see Murray in his underwear 8 times a week. He wore burgundy regular rise briefs. The same colour was in the flowers on my mother's couch in our apartment and I would go home at lunch or after school (whenever I recently had seem him change) and lie on the couch and stroke one off staring at the deep red colour and picturing him in his briefs.
After one curling session towards the end of the season, we had just won a game against another school and the arena was emptying out. Murray had, right after the match, gone to do something so I had deliberately delayed changing so I could be in the locker-room when he changed. By the time he got back we were the only two.
I had already dragged out my changing so I was in briefs when Murray came in. Murray stripped down to his burgundy briefs and then, I guess noticing that I was still there even though the match ended half and hour ago (and was in briefs making not real attempt to put on my street clothes) he looked over at me with a quizzical face and said "what's up."
I didn't know what to say so I just looked down embarrassed.
Murray looked at me for a few minutes and then said "you didn't wait for me did you?"
I turned bright red, probably as dark as the burgundy of his briefs, and again didn't say anything.
"Did you want to talk to me about something", he asked and, when I didn't answer he added, "or were you just wanting to watch me change, because that's cool."
I was shocked.
I knew he was cool but who says that?
I looked over at him, sitting on the bench in his burgundy briefs looking all buff, smooth hard chest glistening from our work out on the ice. He was a star athlete if I ever saw one.
"Have you done anything with guys," he asked, even though I had yet to say a word and spent most of my time standing there in my briefs looking at my feet. "I never have. I would be curious to try."
I looked up at him nervously.
"What have you done," he asked. [For details of my previous experiences read "Roxbury College" in this high school section.]
I was too nervous to answer so he continued the conversation on his own.
"Sucked," he asked. I nodded.
"Been fucked," he asked. I nodded.
"I'd be curious to see what it's like to fuck a guy," he said as though we were just talking about the weather.
"Would you let me," he asked.
Let you?!!! I would pay you! I screamed in my mind. In the moment I simply nodded.
"Wicked," he said.
"Wait right here," he said and then, only wearing his briefs, he left the locker-room. In a minute he was back with a jar of petroleum jelly that he must have gotten from the equipment room down the hall (and the fact that he had so nonchalantly strolled out of the locker-room and down the hall to the equipment room in his briefs to get petroleum just added to how impressed I was with this boy's confidence).
"No one is around," he said, "but let's go into the showers on the off-chance someone is still here," and he took me by my hand and led me into the shower area which, while open into the locker-room, was off to the side so couldn't be seen from the door if someone just popped their head in to see if anyone was around.
Murray shucked off his briefs and gave his cock a few strokes until it was fully hard. It had to be 6 ?" cut and a nice heft - like everything about him it was proportionate. As he was pretty muscular, the thicker cock mirrored that powerful body.The head was slightly bigger than the shaft but the shaft was a good size and it looked on him about the same as mine did on me (just I was slightly shorter and smaller than him, being a year younger, and I had a slightly smaller cock).
As he began to put jelly on his cock I took off my briefs. He then came over to me and applied jelly to my ass, working some into my hole. He may have never done this before but he clearly was experienced and/or a natural.
"Why don't you hold onto the shower stand" he said, nodding to the round central metal tower which had the shower heads all around it (I don't know who designs locker-rooms but they seem intentionally designed so people can check each other out as they shower).
I walked over to it and raised my hands up and took hold while positioning my legs apart. I could feel Murray position himself behind me and soon his cock was searching out my hole. I braced myself for his entry.
Murray slid the head inside and then stopped.
"Does that hurt," he asked. It did but I shook my head no.
No one had ever asked before, and some boys may actually enjoy inflicting pain. [See the one rough experience I had had prior to this point which is the first story in "Becoming Brian's Bitch".]
I don't know if he knew I was lying but he just stayed like that for a while before slowly pushing his cock in inch by inch. As I said, his cock was about 6 ?" inches and thicker than mine, plus it was proportional so the head was even thicker. I guess that is why he was concerned he was hurting me (he probably had girls complain as soon as his big mushroom head entered their virgin vaginas). He clearly was sensitive to me.
Inch by inch he pushed his cock into me. I wanted to tell him he could shove hard, I am not a virgin, but I also loved that he was being so caring.
Before long he was all the way inside me. I could feel his pubes against my ass.
He then surprised me by wrapping one arm around my chest and holding me tight to him. He was slightly taller than me and, holding me close like that, he began to move his hips and thrust up into me.
My ass felt so full with this thick cock and its even bigger head. I couldn't help myself, I began moaning almost instantly.
He kept thrusting up. That mushroom head moving up and down inside the walls of my anal cavity, I could feel it in a way that I had never been able to feel detail before. Yes, when a cock is inside me I feel it, but here I could actually feel the head moving inside me and could feel the shape of that head in my ass.
He kept thrusting up in me and I kept moaning. He kept the same pace. There was no desperate urgency for him to get off and satisfy himself. He was simply enjoying the feel of my tight ass around his hard cock, just as I was enjoying the feel of that big cockhead moving rhythmically up and down inside my ass.
He then surprised me by taking his other hand and reaching around and stroking my cock. No one had ever done that before. In fact, no one had touched it, let alone offered to stroke it as he was now doing. With every upwards thrust his hand stroked my cock upwards and in unison he stroked me down as he rocked back, all the while holding me close to him with an arm around my chest as I held onto the metal shower stand.
I could feel myself getting close and I didn't want to cum before him so I let go with one hand from the shower stand and reached down to stop him stroking me.
"Its ok," he said in my ear, his hot breath against my neck. "I am about to cum too".
I didn't realize he was close because usually boys get more aggressive and he was still doing the steady, almost gentle, upward thrusting of his thick cock into my ass.
I nodded and put my arm back up on the shower stand.
"Can I cum in you," he asked. No one had ever asked that of me before either.
"Yes," I said way too loud, the word ricocheting around the tiles shower room.
I guess my loudness demanded a similar response and his "yes" was equally too loud for the room as he thrust up into me and began to unload his cum as I did the same over his fingers and into the shower stand and floor.
I don't know if his cumming in my ass, that big cock expanding with every pulses, the head spitting its stream of cum deep inside me triggered my orgasm or my cumming which caused my ass to contract on his cum every time I shot cum out in front of us caused his, but it was clearly intense for both of us.
I wanted to collapse but as he was still holding me and I was still leaning against the shower stand I couldn't move. As my cock softened he let go of it and reached forward and turned on the shower, drenching us in water and washing away the sweat from curling and the sex.
He still had his cock in my ass, which even as it was softening felt so thick. I guess he didn't want to pull out because he said "if you can reach the shampoo and soap I can clean you."
How did every girl this boy slept with not want to marry him? He was the most masculine boy at school and in sports and in the bedroom he was a caring lover (well, shower room at the curling arena anyway, it's not like he took me to bed, so I guess I might be being overly sentimental).
I got him the shampoo and soap and he washed my hair and body with especially attention to my cock and balls, all the while his cock was inside my ass and one arm around my chest.
"I have to wash your ass now," he said almost apologetically, which meant that he would have to take his cock out of my ass. Slowly he pulled it out while his washing hand began to soap my ass cheeks and then, as I felt his cock head slide from my hole, I felt his fingers replace it as he washed my crack, all while still holding me around the chest with his other arm.
Letting go of me, he said "rinse". I turned around under the showerhead and washed all the soap out of my hair and off my body including out of my ass crack.
"Let me do you," I said, reaching for the shampoo.
"Nah, I am good," he said, turning off the water. Then, as if he sensed I might take that the wrong way, he added "I got pretty clean by washing you, besides, I will shower before bed tonight."
He then took my by the hand and led me out of the shower room, pausing at the entrance so we could each retrieve our briefs.
Letting go of my hand at the lockers he looked me in the eye and said "thanks, I was curious to try that."
"That was amazing," I exclaimed. He smiled.
"How are you finding the school and town," he asked, making conversation as we died off and dressed. None of the awkward post-sex silence with this boy, he was so comfortable and self confident.
"Lonely," I replied in a surprising fit of honesty.
"I get that," he said. "My parents were in the military when I was younger and we moved around a lot."
"You're becoming a good curler," he added. I beamed.
By then we were dressed and we left the arena together with him saying "see you at school" as we set off in different directions for home.
I thought, yea, we will but you will never speak to me because you are the god of the school, star athlete that everyone looks up to and I am the outsider dropped in mid-year from Ontario.
To my amazement Murray said hi to me every day from then on until the end of the year and would make a point of coming over at lunch to ask how my day was going. We weren't exactly friends, but everyone needs some human interaction and it, plus seeing him in those burgundy briefs changing for gym and imagining his thick cock in my ass, the head moving up and down the interior lining, got me through the year.
Every lunch and after school I would still go home and lie on the couch and jack off staring at the burgundy colour of the flower on mom's couch and thinking of Murray in his briefs. The only difference was now my ass would contract as I remembered his cock inside me and how full he made me feel, as I shot a load on to my stomach.
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