Date: Wed, 20 May 2015 12:34:21 +0000 From: Bruce Demosthenes Subject: Can i fuck you? 14 Give money to Nifty! **** I had five loads of cum in my belly. Even when I had sucked guys off occasionally in public restrooms I had at most sucked two guys off in a day. And those were consenting adults. I had sucked off three underage boys who, while pretty much in charge, they were only 13 and 14 and not nearly old enough to consent. The more I alternated between guilt, regret, longing, lust and denial the more confused I became. So I went to my room and turned on the TV to take my mind off of everything. It was only midnight when I remembered I was supposed to check to see Clifford was in his room. I contemplated not bothering. He hadn't been on the flat at the required time the night before but he also felt he didn't have to and letting him fuck me had hardly been a way to reinforce my authority. My ass was still sore from the 'dressing down' I had given him, thinking of it made me laugh, I had intended to dress him down and I ended up undressed, him on top of my back and his long uncut cock buried in my ass. I decided to check on him anyway. If he was there maybe it might lead to sex. While I had lots of it already that day, I had yet to cum and I really liked cumming last night by his cock hitting my prostate. When I got to his room the light was on. I opened the door and Clifford was lying on the bed in the black boxerbriefs he likes to wear. They really do accentuate his long lean form, though the dark material makes it harder to make out the details of his cock, which may be why I never realized he was uncut and quite large. Clifford glanced at his clock and then said "I don't see why I have to be back by 11pm if you aren't going to come around until midnight." "It's not for me, it is the rule," I said, almost apologetically. "Well I left the 'club' early because of it," he said, putting the word 'club' in air quotes. I had no idea what that meant but I decided not to ask. I already had too many secrets and I didn't want to be in a position where I was supposed to report a boy for doing something they weren't allowed to and then couldn't because what I had done with them was much worse. Clifford got up and walked over to his closet, reached into the dirty clothes and pulled out his jockstrap. He tossed it to me and said "put this on". "Pardon," I said, shocked by his brazenness and not entirely sure what was about to happen. "Last night you got my sheets wet. Not only did I have to sleep in your mess but we don't get new sheets until Wednesday so I have three nights of crusty sheets thanks to you." "Sorry," I said meekly. I began shucking my clothes and once naked I put on his jock. The leg straps and waist band were a little tight, but the pouch, even though I was hard in it, had plenty of room. I also found it an incredible turn on. My cock was where his big uncut cock had been. When he had tossed it to me I had been tempted to sniff it and now I regretted not doing that. Just knowing my cock was where his ball sweat, piss stains and maybe even some cum was just added to what had started as a humiliating exercise (I was wearing his dirty jock because I could stop myself from cumming while he fucked me, something he clearly planned to do again). Clifford pointed to the bed. I didn't need to be told twice. I lay face down on it like I had the night before. And Clifford again reached into the nightstand and pulled out some lube and squeezed it into the crack of my ass. It hadn't struck me the night before but that seemed like a waste of lube, just squeezing it out onto my ass. I hadn't had much experience and my teacher for anal was initially a 14 year old kid who was as inexperienced as I was. I had also had sex with Abbey but I assumed he was a novice to anal given interest in girls. But both of them just applied some, albeit baby oil, to their hand and then rubbed it into my hole and on their cocks. Maybe the extra lube made it easier for his uncut cock to enter foreskin still around the head, which is how I felt it had the night before. Maybe he liked it sloppy so he could slip and slide around. Or maybe he didn't mind fucking my hole but didn't want to touch it (in which case he could have handed it to me to apply to myself). I didn't have much time to think about it as Clifford had mounted the bed, pushed my legs apart and was lowering himself onto my back, his big cock sliding into my very slippery hole. Once the full 7" had been plunged into me I let out a very loud moan. Once again it had connected with my prostate. There was something about lying on this student's bed, barely big enough for one 17 year old boy so too small for me an adult with his virile body above me, almost the full weight on top of me. Clifford began the long slow strokes that I remembered so vividly from the night before. He was a methodical lover and his cock going in and out of my ass was like an oil well steadily pumping the ground trying to bring up the crude. While it was mostly hypnotic, it was also incredibly erotic. I had five loads of cum in my stomach having sucked three boys cocks without any release for myself and this boy was hitting my prostate on every down stroke. I couldn't help myself and before long I was cumming into the pouch of this boy's jockstrap. I tried not to let out a sound. I don't know if he knew I had cum or if he cared. Clifford just kept fucking my ass with long strokes like a piston in an engine. He never picked up the pace, he just kept the same rhythm but something in me knew he was getting close. Maybe it was his muscles tensing or his breathing. I just knew. When on a down stroke he just stayed inside me I could feel his cock pulsing in my ass. I knew he was depositing his load deep in my ass. Something about that was so exciting and I realized I was once again hard in his jock. I was so turned on by feeling this boy cum in my ass. When he pulled out I got off the bed. Clifford noticed my hard-on and asked "I thought I felt you cum." So much for trying to be quiet. I guess he felt my ass squeezing his cock as I came. "I did," I admitted and then added embarrassedly "I found your cumming inside me so hot it got me horny again." "Hmmm," Clifford said. "Maybe we should invite you to the club." This time he didn't use air quotes but I could picture them. He wasn't talking about a night club or a bar. There was definitely something else going on. Did I want to know what it was? I pealed off his jock which was soaked with my cum and threw it in his dirty clothes pile. Then I put on my clothes. Clifford pulled on his boxerbriefs and when he went to the bed he looked at it frowned. "That didn't entirely work," I walked over and saw a wet spot. I had cum so much it had leaked through the rubber material of the jock. "Sorry," I ventured. "We will have to come up with a better solution if you are going to do this again," Clifford said. As I walked down the stairs back to my room I had two thoughts running through my head. First what was the 'club'? And second 'if you are going to do this again', who said I wanted to and he fucked me, it wasn't me using him. Though maybe it was. I was the teacher and he had made me cum both nights. Maybe he didn't even want to have sex with me, though the load of cum in my ass that was leaking out into the back of my underwear suggested otherwise. 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