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Following the game, Randy slowly went with the crowd as it made its way from the football field, hanging back as much as he could without drawing attention or looking any more like he didn't belong, to an open grass area enclosed on three sides by the school buildings. He guessed this was the so called back quad, even though it wasn't quite behind the school, more on the side, and there seemed to be more than four around the school as different wings had been added on over time.
Randy waited near the outer corner of the buildings that surrounded the quad. It occurred to him that maybe quad referred to its shape and not the number of them around the school. He was beginning to regret had had dropped out of school as he was feeling dumb just being in this place, not to mention very poor.
Even though Abbey had told him everyone was welcome he didn't belong here. His clothes and his mannerism cried out that he wasn't a rich kid and probably that he was gay (though he had tried to dress conservatively). He just did his best not to be noticed.
Eventually members of the football team began to join the others. He noticed Brian, who headed directly for the woman and younger boy he had spoken to right after the game, thus confirming in Randy's mind that they were his mother and brother, and that his having sex with Brian today had never been an option.
He saw Jessy and Clifford but they didn't either notice him or think they should acknowledge him. It was just as well. He wanted as little attention as possible.
When Abbey emerged he didn't come directly over, he worked the crowd. He spent the longest time with a very attractive girl and her parents. The father seemed to be beaming, like a father might be of a son who had just achieved a major accomplishment. As Abbey was a boarder it probably wasn't his own father, though he might have come to town to visit the game and the girl was blond and pretty enough to be Abbey's sister.
The other option was that it might be his girlfriend and this was her father, which made him wonder why, if she was his attractive girlfriend, he had agreed to go down the hill with him. Maybe his girlfriend didn't put out, Randy thought. But if she didn't, it was clear from the body language of some of the girls he talked to as he mingled that Abbey could find a girlfriend who probably would put out. He was great looking and clearly popular. There were even some girls he noticed were from down the hill, and not rich families, and he could probably use them for sex as they were clearly football groupies.
He had no doubt, in spite of what had transpired the weekend before and what they were about to do, that Abbey was basically straight. And not a Kinsey scale straight minus one or two. This was a straight boy who was experimenting with his friends in high school. Undoubtedly, when they graduated, these experiments would never be never thought of or mentioned again as these boys got married and had kids and went on with their lives.
He wasn't so sure about Jessy, as the boy seemed too submissive and too into cock to go back. Though in this rarefied atmosphere of private school he suspected the boy would have enormous pressure to marry and have kids and live a straight life. Randy just hoped things wouldn't end badly for him or any of the other boys these football players recruited into their little club.
Eventually Abbey made his way to Randy and asked "did you get something to eat."
"I am fine," said the boy. "I noticed you didn't eat."
"I never can eat after a game, I am always too charged," said the quarterback. "We can go but I just have to talk to the coach first."
Randy followed Abbey, lagging a short distance behind though Abbey didn't seem self-conscious to be seen with him, in spite of his earlier attitude when he came over after the game and didn't seem pleased that he was at the school. Guess being big man on campus he didn't care who he was seen with, he had probably just been displeased earlier because he might have assumed Randy was there to sell drugs and, when he learned Brian had invited him, he relaxed.
Abbey went towards the coach and two people he was talking to, which he guessed were probably teachers. In spite of Abbey seemingly being fine about being seen with him, Randy turned and walked a little further away, when Abbey started talking to the coach, as the quarterback wouldn't be able to explain who Randy was and how they knew each other.
Normally after a game, when all the plays were fresh in Abbey's head, he and the coach would sit down at some point and do a post-mortem, noting what worked well, what needed improvement and what should maybe be dropped from the playbook. They hadn't scheduled to meet but being a boarder Abbey was usually around for when coach wanted to meet and the coach lived in one of the houses on the school grounds.
Knowing he was going off school grounds, Abbey thought it was to ask the coach if it would be OK if they met the next day as there was a 'party' he had been invited to. The coach had no problem but the duty master reminded Abbey he had to be back on school grounds by 11 pm.
Randy recognized the third person who didn't say anything to Abbey and was now glancing over at him as Abbey moved towards the boy, from the sex shop. He had been in the day before looking at lube, though he hadn't bought any.
Abbey said, with what sounded like anger in his voice, "I am good to go, but the dick of a duty master told me I have to be back by 11 pm."
Since Randy had assumed Abbey was coming back to his place just to fuck him and leave, he was taken aback. Was the boy suggesting they spend the entire afternoon and evening and maybe night together?
"I have to work tonight," Randy said apologetically.
"Sure whatever," Abbey said dismissively. "That guy really pisses me off. Of course I know what time I have to be back. I am a prefect; I am the one who makes sure boys obey the rules."
Realizing he had just been rude, Abbey said "sorry, so you have to work this evening," feigning interest "at the sex shop?"
"No, my other job," said Randy.
"Oh," said Abbey, realizing he was talking about selling drugs. The irony that he had just gotten pissed off at the duty master for talking to him about rules and here he was going off with a drug dealer to have sex struck him and he couldn't help but smile.
"Who was the other person who didn't say anything to you," Randy asked, pointing to the relatively young man he had seen in the sex shop, standing with the coach and the person he now knew to be the duty master, whatever that was.
"That is the lower flat master," said Abbey.
"Lower flat," asked Randy.
Pointing to the top floor of the middle building in the back of the quad, which was about two floors lower than the peaked front roof of the school Abbey explained that this was the lower flat. Grades 9 and 10 lived there. This teacher lived at one end and was in charge of the boys and Abbey's room was at the other. He also explained what a prefect does, such as checking the boys are on the flat by 9pm and in bed by 10pm, at least for the lower flat boys in his charge. While Abbey had to do that on weeknight, other prefects would take on that duty on a rotating basis on three out of four weekends. Same was true for the flat master, which is why this other teacher was on duty (thus explaining what a 'duty master' was).
Randy wondered if this flat master was having sex with boys. He had heard that went on in boarding schools. But there could have been any number of reasons why the teacher might be buying lube, including for sex with a girlfriend who is not someone who gets very wet. Just the thought of sex with a girl made Randy cringe.
As they made their way down the hill, Randy asked Abbey more about the school and then moved on to increasingly personal questions. He learned of Abbey's and Brian's sexcapades the year before with girls from down the hill. Abbey wouldn't have been so forthcoming except talking about sex with girls made what they were about to do seem less gay, as the boy next to him was, while not effeminate, obviously gay. For Randy it explained how easily this straight quarterback fell into Brian's trap and willingly let 'sex club' go to the next level. It didn't explain why the two boys had a falling out, but that was none of Randy's business so he didn't pry.
Turned out that the pretty girl had been Abbey's girlfriend and that she didn't put out. Her father was the chairman of the board of Abbey's school. Both factors explained why he was so proud of Abbey.
When they got to Randy's apartment Abbey softened his views of what the boy did for a living. It was clean and the building was not in disrepair but the boy had to be living hand to mouth in what were pretty lower income buildings. He probably had to selling drugs to make ends meet, given he had dropped out of high school.
As soon as they entered Randy began to strip. Abbey didn't need any encouragement; he was amped up from the game and turned on in anticipation, and their talk of the girls the year before he and Brian had gone off with and of his girlfriend as they walked down the hill had added to his desire to get his cock in the boy's ass. His clothes hit the floor as quickly as the older boy. Both were naked and rock hard in under a minute.
Before Abbey could give any thought to what position he wanted to fuck Randy in, the other boy made it clear what he wanted, something that if Abbey knew him better was unusual for Randy as he normally followed the other person's lead. But having watched Brian bent over in front of Abbey all game, he wanted to be fucked in that position by this high school quarterback.
When he proposed the idea, it was an incredible turn on for Abbey. While he was focussed on nothing but the game, the previous weekend he had thought about Brian being bent over all season in front of him with maybe even Randy's cum in his ass.
Randy fetched the lube and slicked Abbey's cock and his own ass and bent over. He leaned forward far enough so his finger tips were touching the floor. He was not one to role play, but if he had owned a football he would have gotten it so as to fully recreate the centre's hike position.
Abbey got in behind him and took hold of his hips. He got his cock to connect with the older boy's asshole and pushed it in.
Abbey was charged with adrenaline from his football win; and right from the outset he began to fuck Randy hard and fast.
Randy was experienced and was used to bottoming but it still was painful as the quarterback rammed his cock into his offered ass. The older boy had misjudged the merits of this position. He had been fucked bent over before, but bent this far over and being rammed so hard he was barely holding himself up on his fingertips. His hands and his ass were in excruciating pain. But he had no intention of Abbey to stop. He knew eventually he would start to enjoy being fucked even in this awkward position, he just had to bear through the pain.
Because of the immediate pounding of his ass and the strain on his outstretched fingers it took longer than usual for Randy to catch up with the person topping him and fully enjoy the roughness of the way this boy was using his ass.
Eventually he was in synch with the high school student and he was no longer bracing against the onslaught but enjoying the pounding and even pushing back against Abbey's thrust to ensure that every inch of this 6.5" cock got buried inside his ass. This had the benefit of talking the strain off his fingers.
With the quarterback hyper charged, it wasn't long after Randy began to thoroughly enjoy being fucked by the quarterback bent over like a football centre that Abbey began to cry out like he was calling a play "twenty-nine, forty-five, thirteen, hike" as he thrust balls deep into the boy in front of him and began busting his nut. Randy could tell the load was big, as he could feel the quarterback's cock pulsing in his ass, shoot his teen age cum deep into his ass. Knowing he was getting cum inside him was to exciting, as he had missed that in an era of condoms.
It took a while for Abbey to stop cumming and he even thust a three times after he was done to make sure every drop of his cum was pumped out of his cock and into this older boy. Then he let go of his hips and pulled his cock out of this tight hole he has so thoroughly enjoyed, almost as much as winning the game that morning.
Able to stand up, Randy was relieved to be out of that position. His fingers hurt, his ass was sore and he had developed a cramp in his legs. But Randy was unsatisfied and wished it had lasted longer. It hadn't been a quick fuck, Abbey had fucked him for more than five minutes, which was impressive given how charged the quarterback clearly had been. It just had been painful for most of it and just when it was getting good for Randy it was over.
Sure he loved the fact that he had been fucked and that there was actual cum in his ass. But if the quarterback had fucked him in a less painful position, Randy might have been able to cum just from the excitement of being fucked by this gorgeous football player who he had seen in his football uniform playing the sport a short while before.
It was his own fault. He had been so turned on by watching the game he had proposed a position that common sense and experience should have told him would be awkward for the bottom. It was just disappointing, as he looked at this gorgeous teenage boy naked in his apartment. He would love to have more sex with him. But Randy had been with enough guys to know that after a guy cums they often bolt, and those are gay guys. This was a straight high school student.
What should have been the most exciting sexual encounters turned out to be one of the worst sexual experience of his life. Well, at least he had this boy's cum in his ass and he could jack off over that fact and the brief moments at the end when it had actually started to feel good, and the sight of him naked and suited up playing football, as soon as he left.
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