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Now that the possibility of fucking Steven on his own without the boys finding out was off the table, Brian decided to tell Abbey and the others that his mother and brother were leaving on Friday so 'sex club' could start Friday night. As it was a long weekend, to Brian that meant three days and nights they could have non-stop sex and the more sex they had the greater chance of his getting to fuck someone or, at least, get his cock in the new boy's ass if Randy's plan worked out.
After practice on Thursday, Jessy, Clifford, Brian and Abbey hung back on the field, still in their football gear, and they motioned for Steven to do likewise. Then they walked to the far side of the field away from the school and sat in a circle. They might raise suspicion about what they were up to, but at least they would see any teacher or student coming and not be overheard.
Steven wasn't yet a member of the club and while the two prefects had intimated to him what they got up to at 'sex club', he was not yet a confidant. Nevertheless, he had to be part of the planning, as he was a boarder and the planning could prove complicated as it was a long weekend and they had two important games. Steven had earned some trust by having shared a mutual blow job (and ass fingering) with Jessy, though that didn't guarantee he would follow through, so they were taking a risk. The two prefects had discussed it and they felt the need to involve him from the start outweighed the risk.
One of the things that made this weekend complicated was that three of them, including the new boy Steven, were boarders and the other two day boys.
Boarders always try to sign out on long weekends. Day boys are free of school rules but have parents who are very involved in their lived.
Most boarders wanted to sign out at weekends, especially in the higher grades, as the school is largely shut down on the weekends and yet there is still a curfew so you are stuck on the flats with little to do but watch television and talk to the other 'inmates'.
While most boarders would prefer to sign out, the challenge is usually boarders and day students don't socialize. Each group keeps to itself. So most boarders don't have lots of friends who are day students; and those that have one or two, their parents don't want to take responsibility for a boarder and no one wants to have a house guest every weekend. This changes on long weekends; almost everyone finds someone's house to sign out to and the parents of day students are more willing to take in a boarder on long weekends because they know the school is largely shut down and the kids will be lonely during the break.
After explaining to Steven that they were making plans for the weekend for 'sex club', the new boy threw the first wrench into their plans. Abbey and Clifford had assumed he would be staying at the school as he didn't have a lot of friends. Turns out his parents were coming in from out of town to watch the semi-final game (something both Clifford and Abbey saw as pointless as he was on the second sting and wouldn't likely be playing. Hell, they were the stars of the team and neither of their parents was going to be there).
So Steven had signed out and would be staying with his parents at their hotel, though he thought he could get away during the day and maybe part of the evening, on at least one of the days, depending on how the game went and what his parent's plans were.
Jessy pointed out that there was no way his parents would let him go out the night before a game (something the other boys all found silly as he was just the towel boy). So his participation would also be limited, especially if the team won on Saturday and had to play in the finals on Monday.
Once Jessy raised the issue of not going out the night before the game, Abbey then began suggesting that perhaps none of them should get together on Friday night because of the semi-finals game the next day.
Both the semi-finals and finals were scheduled for that weekend. As most of the teams come from public high schools the idea of scheduling the finals on a long weekend was designed for parents to come to all three games (the two semi-finals on Saturday, the city-east semi-finals in the morning and city-west in the afternoon, and the finals on Monday between the two winning trams). Parents, players and students across the city could make a weekend of it and see all three games which were played in the same stadium.
While long weekends are difficult for boarders, theirs was the only private school in the city so its voice would never triumph over the public schools. Plus, the current headmaster rationalized not trying change the other principals minds, on the basis that even for boarders it might be helpful in case their parents wanted to come in from out of town (something Abbey's and Clifford's hadn't thought was worthwhile and yet Steven's had - even Brian's mother and brother hadn't though it fit to stick around, though they all knew they were coping with grief at Brian's father's passing).
Jessy pointed out the obvious, that without him there for at least one evening, others would have to bottom. Plus, even if he was there for most of the weekend, he didn't want to be the only one bottoming (something he had pointed out before). This turn in the conversation was troubling to Steven. While he had read the rules and had understood all of the boys had been fucked, and he would be expected to do likewise if he stayed in the club, it seemed like Jessy, who was his age, was the one being fucked by the others. Had he been recruited to be used by the older boys like his classmate? He wasn't sure how he felt about that, or if he even wanted to be fucked (though he had liked Jessy's finger in his ass).
Clifford had been watching the boy, aware that all this was new to him and that he had not yet tried being fucked. Sensing the boy pulling away, Clifford piped up and said "I don't mind being fucked as often as Jessy, but I don't want to be fucked the night before the game, as I don't want to be sore."
This gave Steven, who was doubting whether to drop out of this group, a number of mixed emotions. Clifford didn't seem to mind getting fucked, though his mention of being sore the next day was scary. Was it only because he was the star receiver, so his speed running was a consideration and he wanted to minimize risk, or did you get sore everytime? It looked painful in pornos though the actors all seemed to be enjoying it and he had enjoyed Jessy's finger in his ass..
Whatever the mechanics, how frankly his teammates were talking about having sex excited Steven. He had been told what went on at 'sex club' but their talking about it so matter-of-factly made it suddenly real. He looked at each of his teammates, sitting in their circle wearing their football gear all sweaty from practice and suddenly he wanted to see them all naked and fucking and sucking. If his cock hadn't been restrained by a jock and his football pants he would had a noticeably boner.
Steven was excited about having sex with these boys, as he admired them on so many levels not the least of which was they were all physically hot being star athletes. Though he still wasn't sure about this idea of being fucked, Steven decided he could make his mind up at the last minute as to whether to go and if he decided not to he could make the excuse he couldn't get away from his parents.
As he was thinking about chickening out, Brian piped up and said he had been fucked the night before and even the day of a game. This took all of them except for Abbey by surprise. Abbey had figured out just how intimate Brian and Randy were. In fact, he had wondered whether or not, when Brian was bent over in front him as the centre, hiking him the ball, he might have had cum in his ass (a bizarre fantasy thought that had occurred to him when he discovered Randy and Brian had been fuck buddies well before 'sex club' and had begun thinking about what it would be like to fuck his former friend).
In spite of Brian's assurances that taking it up the ass before a game wouldn't be a problem, no one wanted to chance it and they were back to discussing whether or not they should even get together the night before a game.
Brian didn't like the idea that they wouldn't get together on possibly two of the three nights. The long weekend, with his mother and brother away, was a great opportunity for some serious sex and he desperately wanted to try to advance Randy's plan. He looked at Steven sitting on the grass next to him in his football uniform looking all wide eyed innocent and little bit scared and Brian knew he wanted to be inside the younger boy even if it was only with the new kid sitting on his big cock as Randy had planned.
Brian suggested a compromise. On Friday night they would get together (whoever could) at his house. They would just hang out, naked or in jockstraps of course, playing pool and video games and anyone staying at his place could go to sleep at a reasonable hour in one of the beds upstairs so they got a good night rest. Their game wasn't until the afternoon. Those not staying over could leave whenever they had to. No one on the team would get fucked except for him, and he told them that he was willing to let anyone fuck him because he knew it wasn't a problem before a game (he even claimed he ran faster after being fucked, but this was a dig at Clifford, who was a faster runner than Brian on any day but was chicken to be fucked before the game). Brian also said he was sure Randy would be willing to get fucked.
Steven didn't know who this Randy person was, but the idea of seeing Brian, the team centre, getting fucked was appealing. Clifford had said he would get fucked on non-game nights too. And Jessy had made he clear he got fucked the most. Would Abbey get fucked at some point on the weekend too?
This turn in the conversation with his teammates expressing a willingness to get fucked was reassuring to Steven. He couldn't wait to see it happen and could feel his cock uncomfortably straining under his gear.
The thought of seeing his teammates fucking and getting fucked made Steven completely forget the idea of trying to get out of 'sex club'. Instead Steven was thinking about how he would get away from his parents. Steven asked for Brian's phone number and address and told the other boys he would find a way to make it for at least part of the weekend. This seemed to tip the conversation over the edge and everyone agreed to Brian's plan and making this a weekend long event which made a happy conclusion to their meeting (even if Jessy, as club secretary, felt it necessary to point out Steven wasn't yet a full member and his vote didn't count).
After they changed from practice Brian phoned Randy to fill him in on the discussion and the weekend challenges and final plans. For Randy, this news mean it would require some new strategizing. He had planned to suggest Abbey take Brian's cock by sitting on it, as soon as 'sex club' met, and to say it in front of Abbey's teammates so he couldn't chicken out. Then, when Abbey had taken Brian's cock, as he was confident he would due to peer pressure, it would set the tone for the rest of the weekend and by the end he at least imagined they would agree to add the rule that everyone had to take Brian's cock and open the door to his end game and that was everyone got to fuck everyone else at least one so he could fuck each of these high school boys. That couldn't happen now.
Randy reconsidered his plan. Brian being fucked might work to his advantage, especially Brian's offer to be the designated bottom on Friday (something that surprised him as it seemed like a very generous offer given how much resistance he had put up to not fucking the others). Brian taking it up the ass repeatedly might undo some of the damage Brian had done with his teammates.
As Steven had returned from the field with a hard-on struggling to get free from his jock and football pants, the boy took his time removing his gear, willing it to go down. No boy wants to have a boner in front of his teammates or schoolmates in the high school locker room.
All the talk of sex on the field, followed by seeing the boys he was going to have sex with that weekend in the locker room and showers, meant his hard-on did not go down. Before long he found himself with no shirts or socks but still in his football pants from which he had removed the pads trying to look busy while he waited for people to get dressed and leave.
Struggling against his horniness Steven could help but think of the fact he was not going to be able to go on Friday night, and might only be able to get to go to Brian's once or twice for short periods, depending on his parents. He would have blue balls (while he wasn't exactly sure what blue balls were, he thought he was experiencing them already given how hard his cock was fighting against his wish that it would get soft).
In spite of the risk of having sex at the school, Steven decided he would try to convince Jessy to give him another blow job.
With most of the boys having left the locker room, Jessy was watching Steven who was only wearing his football pants and having the same idea. He too wouldn't be there on Friday, and the rest was also iffy as it was a long weekend and his parents would undoubtedly want to do something. He was equally keen on taking the risk once again with his classmate, though he knew he was pressing his luck.
Jessy had already showered and dressed, as he had wanted to head home as soon as the towels were in the washing machine. Now that he was considering going into the towel room with Steven if he was willing, he couldn't exactly strip back out of his school uniform. But as he considered this as an option he realized he was content to just blow Steven without any reciprocity. Steven hadn't even considered returning the favour. As soon as the last of their teammates left, Steven pushed down his football pants and jock freeing his cock which was so happy to be allowed to string to full mast.
Jessy started at the boy's boner. Any doubt he might be interested in sex with now put to rest. Steven wrapped a towel around his waist and went in the direction of Jessy who was now heading to the towel room with pushing the basket of towels he had picked up while waiting for everyone to leave.
He didn't need to say anything as both boys were on the same page. After closing and locking the door, Jessy dropped to his knees on the towel room floor. Steven dropped his towel and before it hit the floor his hard cock was engulfed by the towel boy's mouth.
Right from the start Jessy's finger (which he had wet before he put his mouth around Steven's cock) slid into his ass. This time he wasn't taken by surprise. He knew what to expect, and he wanted it.
Jessy proceeded to use his finger to fuck the boy's ass, while alternating between deep-throating his teammate and working the head with his mouth.
At 'sex club' Jessy had discovered he loved being fucked. It was hands down his favourite thing to do. But here he was on his knees in front of his classmate and he was loving that too, not just because he was servicing one of his teammates but because he was servicing Steven in particular.
This boy standing above him he had gone through school with and had checked out frequently when they changed for gym class (when the entire school changed for sports after school he found himself drawn to other boys, like Abbey, boys who were stars, but in his own gym class this was the boy he had long had a crush on). He loved looking up at him, standing there naked towering above him, and he loved having his hard cock in his mouth.
Steven was already 'horny as fuck' from the conversation on the field and possibilities of this weekend. The combination of Jessy's cocksucking skills, and being finger fucked, had him unloading into the boy's mouth in record time (which was just as well as having sex in the school was a very dangerous gamble).
As Steven began to cum, Jessy alternated between trying to keep the boy's cum in his mouth (to savour the favour) and swallowing it down (to make room for more and so none spilled out of his mouth). Steven tasted delicious and boy did this boy cum buckets. He seemed to keep shooting more and more cum every time Jessy swallowed..
When the last of Steven's cum had been swallowed by Jessy, the towel boy got up off the floor. He had a hard-on that was quite noticeable in his grey flannel trousers. He didn't have time to do anything about it. He had already stayed late.
And it wasn't as if Steven was offering to help him with it. Steven himself had stayed late first because he was worried about having a hard-on in front of his teammates and then to get blown by Jessy. He hadn't had a shower and it was getting close to dinner (arriving late to dinner is a big thing that would result in some form of punishment).
As Jessy was dressed, even though he was sporting a visible erection in his slacks, he begrudgingly swallowed the last of his friend's cum and then said "let me go first."
Checking to see that the locker room was still empty, he returned and said "clear, go quick" before anyone, especially a teacher, came in, was the unspoken message.
Steven ran naked from the towel room to the shower, grabbed a fresh towel from the pile Jessy had put out on a bench near the shower, earlier, on the way.
Jessy watched him run and couldn't help but check out his ass. His classmate had an amazing bubble but and he had just had his finger up it. While he considered himself a bottom, Jessy decided he wanted at some point to see what it would be like to fuck his classmate. His hard-on in his flannels twitched at the thought.
Realizing if he kept thinking like this he risked cumming in his pants (or at least generating so much pre-cum it would soak through) and that he couldn't leave until his erection went done as someone might see him in the school or on the walk home he quickly closed the towel room door and began tidying up.
Jessy finished by loading the towels into the washing machine, locked up the towel room (a room he had originally hated when he had been made towel boy and now loved) and headed home.
As soon as he got home, Jessy ran up the stairs, his erection having not entirely gone down, stripped off his school uniform and jacked off on his bed, imagining what it would be like to put his cock into that bubble butt. He even sniffed his finger as he wanked, something that surprisingly he found erotic because of his classmate's smell. He had never given it much thought, though he had seen it in pornos, but now he found himself imagining burying his face in between the two firm round globes of his classmate's ass, and maybe even rimming his hole.
And then there was the cock that had just been in his mouth, the massive load from which was fresh on his tongue and warming his belly. Jessy knew he wanted Steven to fuck him with that cock. If he liked sucking on it he would definitely like it up his ass. He might even get Steven to blow him again (while he lacked skills he looked so cute with his lips wrapped around Jessy's cock).
All these thoughts about different sex acts he would like to do, not with anyone else at 'sex club', but with Steven, had Jessy turned on and at the brink of a massive orgasm.
As Jessy found himself starting to cum, of all the things he had pictured doing with Steven while he stroked his own cock he suddenly imagined kissing his classmate. From gentle affectionate kisses, as they held each other to tongue wrestling as they fucked (he didn't care who was fucking whom just so long as they were kissing) his mind honed in on kissing his classmate's sensuous lips. These new thoughts of kissing added to the massive load of cum he was shooting all over his own chest and stomach at the thought of things he would like to do with the other boy.
Jessy came so much he considered taking another shower, but there wasn't time as he had stayed so late at school. Dinner was probably ready.
Using a t-shirt he had under his bed for this purpose he cleaned up his cum and went downstairs. There was so much of it his t-shirt was soaked (and he could feel he hadn't gotten it all off his skin).
Over dinner, as his parents asked him about practice and how he thought they would do in the game, his mind kept straying to 'sex club' (didn't help he reeked of his own cum so was overly prone to thoughts of sex). From the beginning Jessy couldn't imagine how lucky he was to be part of this group. But much as he looked forward to joining in 'sex club' this weekend, he found himself mostly thinking of Steven, and the fact he would be there.
Jessy knew he couldn't kiss him in front of the others (and he had no idea if Steven would be even willing to kiss him). He wasn't even sure he would get the opportunity to do anything with Steven or if his classmate wanted to do anything with him. Just as he had been so excited to have sex with the quarterback, Steven probably was looking forward to have sex with stars of the team and the school.
Jessy still held out hope that at some point during the weekend the two of them would get the opportunity to have sex one-on-one. In his wildest fantasies he wished they would fuck. He was undeniably developing feelings for his classmate.
Was it OK to be having feelings? He had accepted he was gay and he thought Steven was coming to terms with his own sexuality. But being gay in a boarding school would be the kiss of death and would ruin him and undoubtedly Steven knew it would ruin him as well. Would these feelings get him banned from 'sex club' if the other boys knew? Would it turn Steven off?
How, even if Steven had any feelings for him, could they develop a relationship in an all boys boarding school, him a day boy and the other a boarder? Boarders had no freedom and no privacy. That is why he had been forced to take the chance of doing something in the towel room, even though all the teachers had master keys, and the teachers who coached regularly dropped in to drop off or get a towel or to see what state the room was in, which was a foolish risk given the consequences of getting caught (ostracization, suspension or even expulsion).
So that only left 'sex club'. Jessy wasn't even sure he would get to fool around with Steven in that setting. The other boys saw Jessy as the bottom. He had seen the way Brian had looked at Steven, like fresh meet and while Clifford seemed pretty protective of him, he knew that these older boys had recruited him for themselves (a thought that gave him a pang of jealousy).
Perhaps, Jessy thought to himself, 'I will have to settle for the fact I have sucked his cock a couple times and he has sucked mine, and resign myself that this is really the star player's sex club, and take solace in the fact I am included and get to watched and get fucked occasionally by my teammates, just probably not Steven.' Again he felt pangs of jealousy now coupled with resentment at the older boys.
Unbeknownst to Jessy, Steven had decided he was going to choose Jessy for the boy who would fuck him. Jessy had the smallest cock of his teammates. Plus he had given him his first blow job and Jessy's had been the first cock he had sucked. They were both the same age, sort of friends (definitely classmates) and were both outsiders as neither was on the first string with the older boys. Plus he knew Jessy would be gentle. He had liked it when Jessy put his finger in his ass the first time and he had liked it this time when he used his finger to fuck him. While he had fucked him with it, he hadn't been rough, so he was confident Jessy would go slow when he used his cock.
So Steven decided he would, this weekend, find a way to make it to Brian's house, no matter what his parents said, and let his classmate and teammate Jessy take his virginity.
As it was a Thursday evening, the boys had to let the flat master know their plans for weekend. Steven's parents had already called the flat master and said they were coming to town and Steven would be staying at their hotel. Abbey decided he didn't want to be rushed to make curfew, or stuck in the school while others were having fun either, so he filled out a sign-out form to Brian's house and signed Brian's mother's name. Clifford didn't consider signing out, as the idea of forging the form just wouldn't occur to him and nobody had arranged for their parents to sign him out.
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