As the week went on I found myself looking forward to every moment Robert would be alone with me, in his room or in some corner of the school. They weren't frequent, but being able to hold his cock and have his little hand on my cock, at least once a day, was exhilarating.
I still, also, found myself jacking off each night in my jock thinking of Brian's big cock plowing my ass.
I didn't think twice anymore about how I smelled like cum all the time. No one commented on it. In class or in the dining room I could occasionally smell my own cum in my jock and the only effect it had on me was to make me think of Brian's cock in my ass and I would start to get a hard-on. Gone was any sense of embarrassment or fear what others might say. Since the jock was tight, the hard-on would never show in my loose grey flannel trousers so I wasn't even embarrassed about being hard in class.
I found myself not obsessing any more that no one saw the jock. Yes, I had started the practice of wearing the jock under a pair of briefs so I could change in the locker-room with the rest of the school. This had the added benefit of I could go back to jacking off when I woke up in the morning as well. While the jock would still be wet with my fresh cum when I put it on after the shower, the briefs ensured the wetness didn't seep through onto my trousers.
I still went upstairs to shower after sports so the school didn't see me in the small jock, but I didn't race to get in bed while my roommate was out of the room or wait until he left in the morning before getting dressed after my shower. If he thought it was weird I was wearing a jock, and one that was too small, or if he noticed it had cum stains on it, or if he thought it was weird I put a jock on under a pair of briefs, he didn't say anything but he was 100% straight and very narcissistic so I doubted he noticed anything I did. He only ever talked to me about what shoes he should wear with what outfit (he had lots of pairs of shoes). He was also not my type, so perhaps that is why I didn't care what he thought.
As for Robert, he was pretty adept at sliding his little hand down the front of my pants and getting it in under my briefs and jock to take hold of my cock. I am sure he would have preferred my wearing looser clothes; he accepted I had rules and while he didn't understand why I put up with them he never raised any complaint. That was until midweek
Midway through the week, Robert took me aside, not to grope, but to talk. It seemed Brian had told him he wasn't welcome at his place this coming Saturday or any Saturday thereafter.
The next day Brian was in English class and had intentionally sat between people so I couldn't pass notes with him. I waited until after class and, not caring who saw or what they thought, I asked Brian to hang behind so I could talk to him.
When our classmates were out of earshot Brian began with "how dare you".
Before he could continue I said, my emotions having gotten hold of me, "what do you mean Robert can't come over."
"Your little thing bores me," Brian responded. "Get one of Robert's classmates to come over who is new and you can fool around with him, but as for you and Robert: been there and done that."
"And what about Robert," I asked.
"I don't care if you guys make out and fool around, but respect my rule 'your ass is mine'," he said, then added, "but you can't touch him at all until you bring someone new over."
At that point Brain walked off and I just stood there trying to get a grasp of the situation.
I needed Brian to fuck me and I needed him to do that each week. I also wanted to keep having fun with Robert. But, even though I was friends with all of Robert's classmates, more so the boarders, how would I get someone to have sex with me in front of Brian by the weekend.
All of my sexual experiences were due to circumstance, including Robert and Brian. It was an all-boys school and you couldn't just hit on a boy, especially a boy in a younger grade.
So for the next day and a half I dealt with my two problems. First, I stopped Robert from touching my cock when we were alone, which I did simply by explaining what had happened (combined with a massive amount of self-restraint which he didn't make easy as he continued to hang out in his briefs basically from prep until bedtime when I was in his room). Second, I started watching everyone in his class like a hawk and flirting with those boys I was closest friends with. Perhaps a friend would do me a favour even if he wasn't totally into it.
I had a big pit in my stomach everyday as I knew the chances of finding someone to have sex with me in Robert's grade was a longshot. Doing it in front of Brian was going to be a nearly impossible sale.
It was Robert who came up with a solution. When we were alone one evening in his room, him in his baby blue briefs, he said "didn't you used to be friends with Chris?" It took me a second to realize which Chris he was talking about.
Chris had been my next door neighbour as a kid when my parents lived in the south end of Ottawa. It was more Chris's mother was friends with my mother.
"I used to be," I said. "I haven't spoken to him in years."
"Well he said something weird in the locker-room the other day," said Robert. "He said why wouldn't anyone want to be bi, you get to have sex twice as much."
"Was he being serious," I asked.
"I don't know," said Robert. "He says weird things all the time and it's not like I am friends with him."
I had lost touch with Chris, but back in the day (before we had reached puberty) I had played strip poker with him and we had fooled around together a couple times (as we couldn't cum it involved basically exploring each other's cock and balls).
Chris was a dayboy (lived at home with his parents) so I had to sneak off school grounds on Friday night and show up at his house. Fortunately his parents had long since moved out of our south end neighbourhood and their new, much more expensive, home was walking distance from the school (well, a long walk anyway). When I showed up at his door his mom seemed happy to see me and quickly invited me in.
I spent the evening socializing and catching up with his parents, while Chris looked very bored. Eventually they excused themselves and retreated upstairs, leaving Chris and I alone.
"What do you want," asked Chris, who I hadn't talked to since we were neighbours years ago and never even acknowledged at school even though I hung around with so many of his classmates.
"Remember what we used to do," I started.
"We were kids," he snapped back, though he intentionally kept his voice low so it wouldn't get heard by his parents upstairs. "And you were older than me so you should have known better."
Well at least he knew what I was referring to. I had thought just raising the topic would be the first challenge as other boys I fooled around with when I was young denied it had ever happened later on (then again, I had never tried raising it seriously in an effort to start something new before).
Figuring I had nothing to lose and knowing he didn't want his parents to overhear, I moved over to him on the couch in his living room and began grabbing his crotch. He fought me, pushing my hand away and soon was struggling hard to get me away from him. Knowing it was too late to stop I keep fighting him and before long I had his pants open and his cock was hardening in my hand. Once he was hard, he stopped fighting.
"OK," he said, "I give, but we can't do anything here, my parents are upstairs."
"Tomorrow at 2pm at Brian's place," I said, and I went to the table to get a pen and paper and write down the address as Chris did up his pants.
Chris let me out the back glass sliding door and didn't seem too happy about the idea or about what had just happened. I only hoped he would show-up.
The next day I used the enema as expected and made my way to Brian's place. When 2pm rolled around there was no sign of Chris. I sat on the doorstep and waited. It was 20 minutes after the hour before Chris came around the corner. Chris, with his straight dirty blond hair, was wearing a t-shirt and blue jeans and, while when he and I had fooled around as kids he hadn't been the trimmest figure, he was clearly working on building his body. For a 14 year old he was developing a nice broad chest and firm waist.
I felt so relieved. I wasn't sure if Brian would be thrilled I delivered a 14 year old boy to him or pissed that he had been kept waiting.
When Chris reached the door he simply nodded, and I let us into the house and went up the stairs with Chris in tow.
Brian was sitting on the couch, in a pair of sweats and no shirt.
Chris turned to me and said "you didn't say there would be someone else involved."
"He just wants to watch," I responded.
"Wrong," said Brian. Turning to Chris he said, "I own your friend Bruce and if you are going to fool around with him I will be involved."
I probably turned multiple shades of red. While I hadn't been in touch with Chris for years, I knew his family and they knew my parents. Having someone tell a family friend they own you is hardly something you can prepare yourself for - besides, what exactly did Brian have in mind and how would Chris, who I hadn't fooled around with for years, respond.
Chris settled things quickly by saying "I don't know what you guys have in mind, but I am only willing to do oral, giving and receiving."
Chris had definitely grown up - and when I looked at Brian he seemed satisfied with that offer. After all, Robert hadn't let him touch his body and now he was going to be able to touch and even suck a 14 year old grade 9er.
We all began to strip our clothes and while soon I was down to a cum soaked jock, Chris made no signs of caring. In fact, it wasn't long before he and Brian were on the floor and 69ing while I sat on the couch in my jock and watched.
I don't know if Chris had been with a guy since he and I had fooled around as kids, but he seemed more than able and willing to take Brian's cock into his mouth. Brian for his part, while he had never done anything to get me off, seemed just as willing to suck Chris's cock and seemed rather good at it.
A couple of times Brian tried to finger Chris's ass, but got his hand slapped away when he did.
I watched the two of them go at it and found nothing sexual in it. Brian had used me to deliver a boy who he was into rather than me. While Chris was way hotter now than when we had fooled around as kids, I found myself resenting the attention he was getting from Brian. Under other circumstances I might have appreciated his firm body and hard cock. In these circumstances I just found him revolting.
I sat there and watched them until Chris came in Brian's mouth. At which point he announced he was "outta here."
While Brian tried to protest about not having cum, Chris was dressed and down the stairs before it could have any affect.
Brian came over to the couch, his big cock still rock hard, and sat next to me and pulled me over his lap. He then proceeded to spank me hard, all the while reprimanding me for being a half-hour late and for delivering a boy who didn't get him off. While his slaps on my ass stung, and made it seem he meant every word, his hard cock pressing into my stomach told me he had enjoyed fooling around with Chris.
After my ass was very red and very sore, he pushed me off him and dragged me to the arm of the couch and bent me over it. It seemed this was to be my new position for fucking.
Spit on my ass, spit on his cock, cockhead against hole and then it began like last time with Brian fucking my ass as hard and as fast as he could, trying to finish what he had begun with the grade 9 boy I had just delivered to him.
As Chris has done some of the work, and I suspect he was thinking about Chris as he fucked my ass, it wasn't long before he was thrusting more than ramming as his cock began to unload in my ass. Knowing he was cumming inside me was what I needed and my own cock unloaded in unison with Brian's.
With no one to watch, Brian didn't pull out, but kept fucking me until every drop of seed had been deposited in my ass. He even collapsed on my back, I guess having exerted himself or perhaps having been truly satisfied, having both sucked a young boy and having just fucked my ass hard and cum.
Once he pulled out and began to put on his clothes, I quickly pulled on the rest of my clothes and high tailed it back to school.
Waiting for me in front of the school was Robert.
He didn't ask what had happened or who I had found for Brian, though I suspect he guessed it was Chris, he simply asked "is our ban lifted?" I nodded yes and we both smiled.
I followed him into the school and he led me to the chapel, where no one would be on a Saturday, and as soon as we were inside he pushed his hand into my pants. Feeling my wet cum in my jock, he took his fingers out and licked them and then did it again a few times.
Watching him eat my fresh cum I couldn't stop myself, and I quickly pushed Robert down in a pew and had his pants undone. There in the back of the chapel I put his cock in my mouth and I proceeded to blow him. This was probably against Brian's rules. But he had said he didn't care what I did with Robert as long as he didn't fuck my ass.
The school chapel wasn't the most appropriate place to have sex in (if there was a god he was watching and if there was a responsible teacher or prefect who did proper rounds we would probably get caught) but I couldn't stop myself. I was sucking Robert like it was the more important thing in the world.
Like the last time, when he got close to cumming he took hold of my head and I let him take over. Moving his hips be fucked my face until he came in my mouth.
I don't know if for him it was the risk we were taking, the build up from waiting and wondering what I was doing or just having tasted my cum, but when Robert came it was the biggest load I had ever swallowed. And I don't know if for me it was having just been passed over by Brian, having just been spanked and fucked or it was having Robert eagerly waiting for me and wanting me, but I came in my pants just sucking him.
I did know that I would not stop things with Robert, whatever happened with Brian. On the other hand, I still knew deep inside me that I could not part with Brian's cock. Robert and I had to be a secret because if I was given an ultimatum I had no idea which I would choose.
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