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Jessy loved the fact he had cum inside his hero's ass. He had been inside the quarterback and captain of the team, a school prefect. He had realized in the last week that he only wanted cock, in his mouth and in his ass. But while he had no interest in fucking or being sucked, this had been different. He worshiped Abbey and he had not only been inside him he had gotten to kiss the boy and he loved that.
But the whole thing had only taken a few minutes and he had barely moved. He had cum as much from the romance and hero worship and the events of the evening. He was still horny. And he also knew he was running out of time. He had to get home soon, unlike the other senior boys, two of whom were boarders he assumed had signed out and didn't need to be back. He had to be home (and he was kinda fucked up on drugs) by his curfew.
He pulled his cock from Abbey's ass and, before he lost nerve, he committed to trying what he had been thinking about when the opportunity to take Abbey's cherry had been proposed.
Brian was sitting on a chair, Jessy having taken the cushions from the couch, his huge cock hard, having just watched Jessy take Abbey's, who he had feelings of envy and maybe a little crush on, cherry.
Jessy moved over to Brian and taking another bottle of lube from the coffee table he put some on Brian's big cock (which was still partly lubed before when he date raped Clifford). Brian cock began twitching at the smaller hands that were touching his cock as the lube was applied and at the knowledge at what was about to happen.
He found himself looking not just at this young boy's naked body but at his perky round ass and anticipating what it would be like to be inside this kid. While Abbey had taken his cherry already, Abbey wasn't that big (next to Jessy he was the smallest in the room) so Brian knew he would be tight on his cock.
Jessy rose up on his toes and, facing Brian, he moved forward straddling the boy. Brian took hold of his cock and held it still as Jessy lowered his ass onto the huge cock. Brian, for whom coke was now still overwhelming him, got impatient.
If Jessy knew Brian had done coke he might have thought twice about trying to take Brian's big cock. Seeing Brian sitting there with a hard-on he had concluded sitting on him would be the best position because he could see if he could even take this cock and, if he could, control the speed. But he lost control to Brian even before he had taken one-third of the older boys' big cock in his ass.
Brian put his hands on Jessy's hips and pushed down and, at the same time, lifted his hips up off the chair, forcing his cock into the boy's ass before the boy was ready.
Jessy gasped in pain but he had awakened in Brian a need to fuck and the football centre soon had rammed his entire cock up into the boy as he pushed the boy down. The shock was breath taking. It took Jessy a few minutes to give in to what was happening. First he had to figure out what was happening. Second he had to come to terms with the fact that while the intrusion of an enormous cock was unexpected and not something he had experienced before he didn't hate it. And third he had to find a way to hold on for the ride.
Brian was forcing the water boy's hips down and bucking up and Jessy was trying to steady himself holding onto the back of the chair and to Brian who would not stop moving. It was like riding a mechanical bull in terms of bucking with the added complication of a huge intrusion inside his ass that was stretching him so wide.
The cock inside him steadied him in a way, even while he was being thrown around. It was enormous so it was battering his ass even if it wasn't moving in and out much, he was more being thrown around with it inside him. Most significantly it was rubbing non-stop against his prostate which was driving him wild.
Jessy had just cum inside Abbey but his own cock was so hard as this boy bucking up inside him was making him want to cum so badly not from his cock but from the inside out.
He knew he loved cock. But Jessy's love of cock was an extension of his love of boys. He worshiped these boys on the football team. He especially loved looking at Abbey who he looked up to and might even genuinely be in love with. When Abbey let him suck his cock in the locker-room he was blown away. He wanted to service the quarterback to show how much he loved him. He had that very day let Abbey take is virginity. But all of that was about bringing pleasure to Abbey. This was different.
Jessy, as he held on and tried to ride the fucking out, was totally enjoying what this cock was doing inside him. He had been hesitant to sit on it as it was so big and now it was driving him wild. Yes part of him wanted to please Brian - he desperately wanted to give the older boy pleasure and when Brian came inside him he would know the boy enjoyed his ass - but this big cock was touching places he didn't know existed and he was enjoying it himself.
Jessy wrapped his arms around the blond boy's neck and hugged him tight, in part to steady himself and in part out of affection because he loved what this was doing to him. He didn't want to kiss this boy, the way he had Abbey, but he did want to hug him and as he hugged him his cock rubbed against Brain's abs and he began to cum.
Jessy gasped at the rough ride he was getting sitting on this boy who wouldn't stop thrusting up and moving around on the chair, his big cock moving relentless inside of him and at his own orgasm which had been triggered from the inside by the mammoth cock rubbing his prostate taking him by surprise.
Brian didn't stop when Jessy came. In his coke driven lust he just was thinking about one thing and that was making himself cum. While he had been turned on by thinking about fucking the water boy, this far into fucking him he had no regard for his welfare, he just needed to cum.
Brain continued to used his legs muscles to push his hips up and around and move his cock around and in and out of the boy hanging around his neck just above his lap.
Jessy just held on. Having cum, the onslaught of the older boy's big cock on his ass was painful, but Jessy wanted to please him and made no move to stop or slow what was happening.
Having wrapped his arms around Brian's neck and hugged him he was no longer being thrown around like he was riding a bull, he was perfectly still. This allowed Brian to move in and out of his ass easier.
It took another five minutes of fucking the towel boy clinging to his neck before Brian began to cum. And what made him cum was not just the workout his cock had inside this younger boy's ass, it was also the sight in front of him of Clifford beginning to sink his cock into Abbey's ass.
Staring at Abbey and wishing he was the one entering the quarterback as Clifford was doing right now and like this boy he was fucking had done before, he began to cum inside Jessy.
As Jessy felt the big cock expand and contract in his ass, felt the pulsing along the underside, as Brian shot a load deep inside him he gave out a sigh of satisfaction. The ride had been worth it, he had pleasured the football team's star centre. The load of his cum inside him was proof.
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