Being in a private school meant you didn't go to school in your own area. So where the school was in a fancy area of Ottawa, my parents (being just teachers) lived in the south end. Not surprisingly, I became friends with the boys who lived nearest to me.
In grade 8 the four or five boys who lived in our area of town from the school all hung out at Simon's house on weekend, as he had the biggest house, his father being an orthopedic surgeon.
Simon and his younger brother Garth shared a room and off of their room there was a larger 'play' room where we could watch TV and hang out. There was also a basement in which there was a small room (basically a closet with a bench to sit on) with a door where Simon and Garth were permitted to keep their penthouses and playboy magazines (their mother would not allow them in the main house).
I never saw the rest of the house which was off limits to us boys.
We hung out there many weekends during the school year and during the summer we found ourselves at Simon's house at the beginning and end of every day. It was a convenient place to meet. It was near a beach, and being a fairly big place there was tons to do.
In addition to Simon, it would be at least his brother who was always there and one or two other of our schoolmates. We would play basketball or stick hockey or watch TV in the play room. But we would also invariably 'wrestle'.
The wrestling was not rough. We weren't out to hurt one another, though we would put enough effort into it so that the stronger would pin the less strong. But it was as much about physical contact (or I thought, which may explain why I lost every time),
For me it was about grabbing each other's cocks through our jeans which was part of the game.
Simon had just turned 15. He was black, tall and lanky, which made him look even older than he was. I was 14, having turned 14 shortly before school broke for the summer (in mid-May).
Simon had a younger brother Garth, who was a year behind me so he was probably my age of 14, though I never asked and I always thought of him as younger since I was in Simon's grade. Thought he was hot, just not as tall as Simon, so he had definitely come into his own and I admittedly did check him out whenever we were together.
Simon and Garth (and his parents) were the first black people I knew. As an example of my ignorance and isolation, one day we were in their bedroom and Garth took off his shirt and I saw his arms were darker than his upper body and I exclaimed "you can tan" and the two of them looked at me like I was an idiot. But at 14 years old, I didn't know any better.
Simon just exuded heterosexual sexuality and would frequently flirt with my mother, which even though he was only 15, made her uncomfortable. I would deflect by offering to swap my mother for his (his mother had been Miss Barbados so this would probably have been any straight boy's dream and while I recognized she was attractive it was nothing more than a clumsy attempt to make me seem as cool and as sexual as Simon).
At 14 with my hormones raging, on a few occasions when I was wrestling with Simon or his brother I would get a hard on. I was usually successful at hiding it but on one occasion Garth saw it and pointed it out to Simon. I was so embarrassed that I ran home.
Usually we were a group, but one day I found myself alone with Simon in the small room where they kept their penthouses and playboys and, as we were looking through the magazine, we were joking around about sex and who was the bigger ladies man (even though neither of us had had a girlfriend being in an all boy's school). As boys will do expressions like "blow me" get thrown out during the banter, but in the presence of Simon's overt sexuality, my response instinctively was to say "OK".
Simon laughed and shoved me as in 'you're not serious' but I guess my expression told a different expression and his face went quizzical. Reaching down he grabbed the front of my pants and sure enough he found a hard on. I was clearly serious.
"OK, you better not chicken out" Simon said, as he started to undo his pants.
I have seen Simon in his underwear (always white briefs) in the locker-room multiple times so I knew that he was well hung, but I had only seen it soft in his briefs and didn't know how big it actually was.
Shoving his pants and briefs around his ankles, Simon exposed his now hardening cock which had to be about five or six inches in its semi-hard state. My eyes went from his face to his cock and back again repeatedly before I dropped to my knees and took his cock in my hands and began to fondle it.
I could feel it fill with blood in my hand and before long it was fully rock hard at about seven or eight inches. Simon had to have the biggest cock of all the boys in our school. I had measure mine and it was a little over four (I was optimistic it would grow to maybe six or seven when I was 18 but here was a cock that soft was as big as mine would ever get and hard would put most adults to shame).
I tried to put as much of it into my mouth and throat and I gagged.
Simon pulled me off it and said softly "just start with the head".
I did as he suggested and I began to lick the head.
"That's right, now take your time", he said encouragingly.
I ran my tongue around the head and began to move my mouth further down the shaft.
Realizing I was about to try to take more than I could handle Simon said "that is far enough, just work the top part up and down".
I noticeably relaxed as I realized I could just work on the top two or three inches and not take this massive cock down my 14 year old boy throat.
Simon sat down on the bench bareassed, pants and underwear around his ankles. And I moved forward on my knees and began to work the top one-third of his cock.
Up and down went my head and my hand instinctively went to his balls and the shaft. My left hand stroke the shaft while the right played with his balls as my head bobbed up and down.
Simon began to moan gently so I figured I must be doing a good job. I responded by sucking harder (not on more of his cock, just more suction on the one third I was working like I had learned to do with Tony).
Simon's hands began to run through my hair and while he wasn't encouraging me to take more, it made me want to, and before long I had transitioned from sucking the top third to relaxing my throat muscles and taking it down into my throat. By focusing on relaxing I could get about two thirds of his cock going in and out of my throat in each plunge.
Simon was panting and moaning loudly now and his fingers in my hair and on the back of my head were becoming more forceful. This had the effect of making me take even more of his cock down my throat and to my surprise I was able to get his entire cock down my throat.
Who knew at 14 years old, having only sucked one cock in my life. i would on my first attempt on a big cock master deep throating. I was taking a seven or eight inch black cock down my throat. Now granted, Simon was only 15 so the cock was not as thick as an adult eight inch cock, but equally my mouth and throat was not as big as an adult cocksucker.
Deep throating Simon I would take the entire cock down my throat right so my nose would be in his pubes. The trick, I learned, in addition to relaxing, was to not take it all the way out on the upstroke. Leave it in my throat and just have it move in and out, driving my nose into his pubes and then sliding up and driving them back down.
I was entirely focussed on this exercises of moving this cock along the cavity of my throat that before long the only thing in my head with the thought of his cock. I had stopped playing with his balls or even noticing his moaning. The only thought in my head was the surface of this hard cock in my throat.
So I was startled out of my transfixation on that cock when on a down stroke with my nose in his pubes Simon took hold of my head in his two hands and held me firmly in place. I could feel his cock expand in my throat as it pumped his jizz deep into my throat and into my stomach.
He held me like that for what seemed to be an eternity and then let go of my head.
Pulling my head off his cock I looked up at Simon.
"That was awesome" Simon said. "How was it for you?"
"I liked it," I said, somewhat embarrassed (cause that meant I liked sucking cock), "but?" I trailed off even more embarrassed.
"But what," asked Simon.
While I knew what I was about to say made me even more of a cocksucker, I was kneeling infront of him and he still had his pants around his ankles and my hand on his cock (which was still hard) and balls so it wasn't like he was going to call me a fag and hit me or anything.
"I am kinda sad I didn't get to taste your cum," I said. "You came deep down my throat."
"Yea, that was awesome," Simon said, with a big grin on his face. And then when he realized I was serious he said "no problem".
Simon then wrapped his hand around his cock and began to jack off. Closing his eyes he stroked his cock hard and fast. He tenses every muscle in his body and stroked, willing himself to cum a second time and in what was a very short time he said "now, put your mouth on it" which I did and he unloaded voley after voley of sperm into my mouth.
For someone who had just cum he came a lot in my mouth. Even after I let his cock slip out of my mouth, I just held his cum in my mouth, running my tongue around it tasting it.
Simon stood up and pulled up his pants and underwear and then leaned down, squeezed my hard on through my pants like he had done when this all started, and whispered in my ear "I will leave you to finish up".
After the door closed I undid my pants and took my cock and stroked it, his load of cum still my mouth (and another likely much bigger one in my stomach). It only took three or four strokes and I came all over the floor, the biggest load I have ever shot. Only then did I swallow before putting my cock away, and then cleaning up the floor.
When I went upstairs Simon was watching TV with his brother, who looked up surprised when he saw me come out of the basement (guess he didn't know I was over). Garth looked down at my pants and laughed. I looked down and realized some of my own cum was on my pants.
"Jeeze Bruce," said Garth, "if you are going to jack off to our magazines use some tissues".
"I have to get home," I stammered, before ducking out of the house and heading home.
As soon as I got home I jacked off again thinking about what had occurred and wondering if we could do it again. We never did.
Simon never mentioned what had happened and shortly thereafter Simon informed all of our group of friends that his father had said we couldn't grab each other's cock when we wrestled because we could 'hurt ourselves so as to prevent us ever having kids'. I don't know if his father had said that. Didn't even know his parents knew we wrestled as we did it in the play room and they never came in, but his dad was a doctor so he might have if he knew. It's more likely Simon felt guilty about what we had done.
Like Anthony, Simon convinced his parents to take him out of private school and he too was gone.