This is a back-story [you don't have to read the other story to understand this one which you know by now if you have gotten to chapter 5]. The other story can be found at http://www.nifty.org/nifty/gay/athletics/first-rule-of-sex-club/
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The very next day Brian called Randy. In his excitement at having sucked the older boy, Brian had not even thought about buying pot from him. Plus he couldn't stop thinking about this tall skinny boy with dark hair and piercing blue eyes.
There was something worldly about him and as Brian was interested in exploring more, he thought this boy might someone who could teach him. He lived not that far from him, even though they were worlds apart.
Brian was rich and lived at the top of the hill and went to a private all boys school. This boy was a drop out and a drug dealer and lived in an apartment under the hill that was so small it could fit in Brian's kitchen.
But to Brian, Randy was amazingly hot and his being a boy from the other side of the tracks (well down the hill anyway) made him even sexier. Randy was slightly older and clearly was experienced. Then there was that cut cock with a mushroom head. It was so amazing to suck (way better than all of the men he had sucked off in the back of the sex shop, though it probably helped that Randy was close to his age and the cocks shoved through the holes in the booths were probably not).
The fact that Randy shaved all of his body hair off, including all the pubes, fascinated Brian. And it also made Randy's cock look to Brian almost as long as his own.
Brian had measured his own cock repeatedly since he had been 13 and now at 17 in his final year of high school, grade 12, it was already 8.19 inches and he knew from the locker-room, which probably made him the largest in the school.
Brian was fascinated by this boy's cock and he wanted more. For him the drugs were just going to be icing on the cake. He could get (and had been getting) them from a boy in his school. Maybe he could get them cheaper but money meant nothing to Brian. This was about experimenting with sex with a boy and his mind was swimming with ideas of things he had read in penthouse forum he wanted to try.
Brian had a girlfriend and for about a month he had been fucking his girlfriend, albeit not as often as he would like. He had known her all his life as she lived in the same community and their parents were friends. She went to the private girls' school as most of the girls in their neighbourhood did.
He had changed their relationship from that of family friend to dating largely because the high school quarterback was dating her best friend. He played centre and felt a little competitive with the QB (he probably felt attracted to him too, but Brian was not far enough into his sexual exploration to consider that possibility). He and the QB had been friends, they had even gone with some chicks together to be blown the previous year, but they had drifted apart. He had thought dating the QB's girlfriend's best friend would mend fences but it hadn't.
He still liked the girl he was dating. They had given each other their virginity. And she not only let him fuck her ever since she totally loved it. His big cock seemed to drive her wild and she most recently had begun to dig her nails into his back which while he took as a compliment it was a bit painful. He had thought about asking her to stop but they didn't have sex that often. Both lived at home and while his mother and younger brother pretty much left him alone (both were dealing badly with the death of his father), her parents were strict.
They basically only hooked up when there was an event between the two schools (they would sneak off and find some place to fuck quickly) or when her parents were out (and he would come over and they could actually get naked and fuck in her room, which was where the digging her nails into his back had started).
The things he had read about in penthouse forum that were somewhat kinky he couldn't imagine trying with her (and some required a cock to try so that ruled her out).
Brian liked fucking her, but he found himself intrigued by cock and now by Randy's cock in particular and about the possibilities.
Down the hill, Randy was surprised when he answered his cel, expecting one of his customers and not imagining the high school boy from the day before would be on the line. In fact, he had guessed when he game him his number he would never call (most guys take a number and promise to call out of politeness never intending to, or they intend to and then chicken out, especially if they were young, and this boy couldn't be older than 17).
When Brian proposed buying weed and asked about prices, it made sense to Randy. They had smoked up together and Brian clearly did like getting high and had some experience with weed. Randy was fine with just dealing the boy drugs.
Randy had enjoyed the boy's exploring his body, giving him a tongue bathing and sucking his cock (and he TOTALLY enjoyed knowing he was having sex with a high school student). But Randy he was more into money (he needed money, he was no mean flush) and selling this boy drugs could make him and maybe lead to lots of money if he got introduced to Brian's friends and got more customers.
After they negotiated a price, which Randy cut him some slack on since this was an investment in the hopes that this might lead to some rich classmates. He agreed Brian could come over on Friday evening, though early, since he had to be at the club to deal by nine or 10 pm latest.
When Friday came, Brian changed after football practice and headed down the hill. He didn't bother to go home first, and change out of his school uniform.
While Randy was surprised when he opened the door to find Brian standing there in a school uniform, he also found it increadibly hot. He had surmised this boy was in high school and that he was rich, but here he was in his grey flannel pants, green blazer, school tie and white shirt from the boys' school up the hill.
In spite of himself he found himself getting hot and bothered. He knew this was about selling the boy drugs and there was no possibility of sex, he found his cock hardening.
As soon as Brian entered the apartment Randy closed the door, went over to the table and picked up a joint and lit it. He never smoked while selling drugs (you run the risk of screwing up transactions or being taken and not only was he about to sell this boy drugs he had to be at the club later). But he instantly decided he wanted to have sex with this private school boy. Little did he know Brian had the same goal, to have sex with him.
There wasn't much furniture, just a bed and a table and two chairs. Brian went and sat on the bed. Randy didn't see this as evidence the boy was there for sex. The kitchen chairs were hardly comfortable. Randy went and sat next to him.
The two boys passed the joint around. Randy, still thinking Brian was there solely for drugs (even if he thought he could talk him into having sex) focused the conversation on business while they smoked. 'What did Brian usually pay', 'did he know he got a special price', 'did he have possible customers who he could introduce him', 'would he promise not to tell anyone the price he got', and so on.
With every answer Randy got more excited about the possibilities to make money. At the same time, the more he smoked the more excited he got about this boy sitting next to him.
Even in a blazer and loose grey flannels Randy could tell Brian was athletic. Under his grey flannel you could see strong thighs and his shoulders, wider than Randy's, suggested a nice chest and back spreading those nice wide shoulders.
While Randy still hoped to seduce the blond fit prep school boy sitting on his bed in his school uniform, he needed to get the business out of the way. Randy put the joint out, got up and went to the table to get the bag he had measured out before Brian arrived.
Brian watched him moving around the apartment. He was quiet as he watched, and as the drugs infiltrated some of his senses and as his horniness began to build. This boy was so skinny and tall. he wanted the 7" cock in his mouth again. He wanted to get his lips around that big mushroom head. He wanted another load of cum shot into his mouth.
As Brian studied the boy, his cock began to harden. He had worn brown low rise briefs to school. He thought he looked sexy in them. He wore lots of different style briefs because he liked being in them and, he hoped, being seen in them in the locker-room. In fact he spent a lot of time in his briefs when changing before and after sports. He had chosen to wear these as they were his smallest and sexiest. But being small they were confining his cock.
Brian was trying to figure out how to solve the problem. His cock had started pointing down in the pouch. That is what he liked about these briefs. They made his cock lift and with his balls pushed them up and out. But now it was struggling against the pouch, pushing it out as pointing down it tried to expanded to full size. If he reached into his pants and underwear he could maybe make it point up instead of down but they weren't that big so his cock would be above the waistband and there was no way to do that subtly. He really needed to get his pants and underwear off.
Randy came back, handed him the bag of weed, and then sat next to him on the bed again. Brian fished out all the cash in his pocket and handed it to the boy. Randy counted it and found Brian had given him too much. He counted it again and confirmed the amount was too much. He gave Brian the extra money back to Brian.
Brian didn't care. He shoved the money in his pocket where he had pulled it out from without counting.
Business out of the way Randy turned to look at this attractive blond boy. Looking into his eyes Randy couldn't help himself. He had planned to seduce the boy but the proximity was too much and he leaned into him and kissed him.
Brian hadn't expected that. He had never kissed a guy. The idea of kissing a boy had never entered into his growing list of things he hoped Randy might do with him. But as their lips met Brian surrendered into the idea and soon he was opening his mouth in response to Randy nibbling on his lips and his tongue trying to enter his mouth. Soon they were French kissing.
Brian didn't really get into kissing. Most of his high school classmates got into making out. He had always wanted to skip that and have sex, though he didn't mind kissing during sex. This was the latter and it was getting him hotter.
This was not like kissing his girlfriend. Randy was the one who was dominating the kissing and he found himself giving into this boy's oral onslaught. The more he kissed him and the more aggressive he got and more his tongue probed Brian's mouth the more Brian found himself turned on.
He had been uncomfortable before and now he was in pain. His cock needed out of his pants.
Brian broke off his kissing.
Randy was confused and disappointed. Had he moved too fast? He knew straight boys and men and even gay men in relationships often will have sex with not kiss, it was just Brian looked so cute on his bed in his school uniform.
Brian undid his belt, undid his zipper on his grey flannels and pushed his pants down to his ankles and reached into his packed and stretched lowrise briefs and maneuvered his cock so it was not fighting against the pouch (no easy feat since he was so hard) and pointed it upwards and then let go of his briefs. His hard cock was half above the waistband.
Randy's mouth was ajar.
This boy was younger, looked even younger than the Sunday before in his school uniform, and here was this huge cock. It had to be over 8" and it was thick. This boy had a bigger cock than him. He also had on sexy small tight fitting briefs that couldn't confine him.
And his thighs were so firm. His cock was not only longer, it and his thighs were probably twice as thick as Randy's.
Randy's staring at the boy's cock, briefs and legs was interrupted by Brian leaning back in and meeting his lips and soon they were back kissing.
Randy couldn't stop thinking of Brian's cock sticking above his briefs and as he did he went from the aggressor in kissing to being the passive one and soon Brian was the one kissing him and biting his lips and shoving his tongue into the older boy's mouth.
Brian, now that sex was under way, wanted to do what he had done the week before and suck off Randy. His hands went to Randy's pants and started to undo them.
Randy though, having just seen Brian's big cock (Brian hadn't undressed last Sunday so he had no idea what a treasure was in the boy's pants or he wouldn't have settled with just lying there and letting the high school student have fun), had different plans.
Randy's hand went to Brian's cock as they kissed and he felt the warm smooth skin of the half above and the cotton covered cloth of the half still in his briefs as well as his underwear covered boys. Randy had an underwear fetish, and a bit of a thing for school uniforms it turns out, and he liked big cocks and he had considered himself lucky the week before just knowing this boy was young. He was so turned on by this boy there was only one thing he wanted to do. He wasn't to strip this boy and get fucked.
Randy was versatile. He could do either. But with this boy he only wanted to do one thing.
Brian had Randy's pants undone and was reaching into his white briefs, taking hold of that cock he had been thinking about each week.
Randy pushed Brian's blazer off his shoulders and started undoing his shirt. Brian let go of Randy's cock and pulled his hand out of his pants to undo his own tie so Randy could get his shirt off.
Brian used his feet to push his grey flannel off his ankles and feet, not caring that his nicely pressed school uniform was now in piles on the floor and on the bed.
Randy pushed Briand back on the bed and took hold of Brian's sexy briefs. Under other circumstances he might have sniffed and licked the boy with his briefs on but he wanted to see that cock and get this boy naked (regretting he hadn't done that a week before, what if this boy had never come back).
Randy paused to look down at this naked boy. He was so hot. Nice broad shoulders (broad for his age, he was by no means some muscle freak, more like a swimmer's boy Randy thought, not knowing he was a high school football centre, who have similar builds).
Brian's cock was even more gorgeous than him and he was so hot Randy knew his precum was soaking his briefs. It was definitely more than 8" and about 1.5" across. The head was the same size as the shaft, except for the bottom of the head when flared out.
Randy was now so horny he jumped off the bed and ripped off his own clothes, all the while looking this hot boy on his bed up and down. He grabbed some lube from the drawer in his nightstand and squeezed some on Brian's cock. He rubbed it all over the cock and squeezed some on his hand and slapped it between his cheeks into his hole.
Randy got back on the bed and knelt straddling Brian and aiming this big cock at his hole he leaned back down.
Brian had wanted to suck Randy again but this turn of events was not unappealing. He had been turned on reading about fucking an ass even though the stories in his penthouse forums had been about fucking girls in the ass (something he would never suggest doing with his girlfriend). Here it was about to happen.
Randy felt his ass stretch as the boy's big cock began to enter his ass.
Damn this boy was impressive. He was as big as any of the well hung men who had fucked him and looking down at him he was anything but a man. He had the look of anticipation, of eagerness, or surprise, and of innocence tempered by horniness and a touch of a smirk because he was knowing he was doing something straight men didn't do.
Once Randy had Brian fully inside him he leaned forward and resumed kissing this 17yo boy in his bed. As they kissed, now as equals, taking turns leading and following with their tongues and their lips and their teeth on the other boys' mouth.
Randy began to twerk, moving his hips up and down and around as they kissed. This had the desired effect and Brian was soon moaning and panting as his cock was worked by the older boy.
Brian reached with his right hand for Brian's cock, wanting to grab hold of this mushroomed headed cock he had been thinking of all week that was rubbing against his stomach as he lay on top of him. But Randy pushed his hand away. Randy had good staying power but he was so turned on by this boy who he had stripped out of his school uniform and was now riding his cock. He didn't want to cum before him (with Brian's big cock he might need to stop once he came).
Brian didn't know why the boy didn't want him to pleasure his cock but accepted that and moved his hands to the older boy's ass. He ran his hands over them, squeezed them.
As Randy continued to kiss and twerk Brian began to move his hips. Randy had most of the teen football player's big cock in his ass, but there was enough room between him with the older boy leaning forward and kissing him than Brian could move his cock up and down by flexing his hips and pressing up with his legs which he bent slightly to get some leverage.
Fucking upwards and feeling the skinny boy's ass Brian instinctively began to periodically slap the boy's ass with one hand and then the other a short while later. This encouraged the boy to move his hips more which combined with Brian's upwards thrusts we bringing the boy to orgasm.
Before Brian came Randy began to shoot cum all over Brian. The first shot hit Brian and Randy in the chin as they kissed. The next three ropes covered Brian's chest and stomach. As Randy was shooting the last ropes of cum, onto Brian's belly button, treasure trail and pubes, getting them both wet in the process as this shots of cum arched up between them and their two bodies moved against each other, Brian began to cum.
Randy could feel Brian's big cock pulse in his ass. As it expanded he knew that the boy was pumping cum into him.
With strangers he always used condoms but with this inexperienced high school boy who he assumed from his behaviour he was his first he was getting his cum in his ass. He hadn't been cum in for years and now he was getting cum pumped into his ass. He could feel every time the boy's big cock expanded to spew forth what he knew had to be huge shots of cum inside him.
Where he had shot nine times onto the boy beneath him, this younger boy shot 12 into his ass.
Randy collapsed on top of him, pressing his cum between their two bodies. While his legs were cramped, he lay there on top of the boy spent, but also not wanting it to end.
Brian softened in his ass, but was so big that he didn't slip out. It was only when Brian moved and began to push on his hips to urge him to get off of him he reluctantly got off the boy and let his big cock, now soft but still impressive, slip from his ass.
Randy proposed that they shower together and Brian said no. But asked to use the shower. Brian had just cum with a guy fucking and he wanted out of there as quickly as possible. He didn't regret what had happened. But he wanted back to his own world and have some times to process what had happened (kissing, fucking???).
Unfortunately Brian was covered in the boy's cum and he had only his dress uniform and he couldn't put his clothes on without being clean. Randy suspected what was going on so he handed Brian a fresh towel and as the boy went into the bathroom, closed the door and ran the shower and began to clean himself.
Randy didn't put on clothes. First he too was covered in cum. Second, he wanted Brian to see him naked again before he left hoping that whatever guilt of confusion he was feeling would, as he reflected on what they had done and pictured him naked, would be replaced by lust.
Brian came out of the bathroom having showered and dried himself. He didn't say anything, he just got dressed. But as he put on his clothes he couldn't help but look over occasionally at the naked boy he had just fucked.
Randy, naked, walked him to the door, and as Brian turned to make some halfhearted excuse for his mood or why he wasn't speaking and leaving right after sex, Randy grabbed the lapels of Brian's blazer and pulled him towards him. There in the open doorway, completely naked, Randy kissed him. Brian in his school uniform (except for his tie which made no sense to put on, he had just shoved it into his jacket pocket) responded and found, in spite of himself, kissing back and soon they were making out.
When they stopped Brian said apologetically "I have to go."
"I do too," said Randy. "Next weekend?"
Brian nodded and said in raspy breath "yes."
Randy closed the door behind him and got in the shower. He had no idea if it would happen again but the way his ass felt having had that big cock inside him and the big load of cum he could feel in there (some of which he had to keep washing away as it leaked out) he was happy.
Maybe he had complicated things and he wouldn't see the boy again, wouldn't sell him drugs and wouldn't sell to his friends. But he had just had sex with one of the hottest boys he had ever met with an amazing big thick cock.
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