"Who the hell is she?" bristles the coach, gesturing angrily to the young girl sitting on the bleachers by the football field. "Is this some kind of joke?"
"Sorry coach," says one of the football players, smiling sheepishly. "That's just Tom's little sister Jenny. She just got into the cheerleaders in her school, and you know, she was so excited to wear her uniform and cheer for a real football team, we thought we'd humor her a little."
The coach rolls his eyes, clearly unamused, but he's not the type to needlessly squash the enthusiasm of a young girl, and says only, "Fine. Just make sure she stays out of the way and doesn't cause a distraction."
The football player grins over at the young girl in her black, white, and orange cheerleading skirt. She smiles back diffidently. The boys line up on the field and begin their practice.
On the bleachers, Jenny, who is not in fact a girl at all but Tom's younger brother Jeremy in a long-haired wig, fidgets uncomfortably. He's not particularly enthusiastic about being dressed as a girl, but one of the football players, Arthur "Toombs" McDevon, had told him that it was his responsibility as a chick to come cheer on his brother and the team, and that since most chicks were girls, it would only be appropriate that he dressed like one.
'Chick,' Jeremy has come to understand, means 'someone who is popular because they make boys feel good.' His brother's friends have been teaching him a lot of stuff about being a chick lately, and each new lesson seems to leave him more popular than the last. He's particularly excited today to be allowed out on the field to watch the older boys play football, something he himself is very much looking forward to being old enough to do. Having to dress like a girl seems a small price to pay to do so.
As one of the boys walks by the sidelines, he throws Jeremy a wink. Jeremy smiles back at him. "Come on," says the boy. "You're our cheerleader. You should cheer."
Jeremy smiles, but feels less confident than he wants to appear. He stands and feels a sharp twinge in his anus from the motion. The vibrator buzzing away inside of him does not take kindly to shifts in his weight, and standing up makes his insides tighten around the cock-shaped toy in a way that makes his knees shake.
Still, he does his best. He grabs up the pom-pons given to him by Toombs (apparently belonging to his sister, who is also the original owner of the uniform Jeremy is now wearing) and gives them a half-hearted shake. "Woo!" he shouts. "Go Tigers!"
He can see that the football players seem amused by this, and that makes him feel good. He likes being popular with Tom's friends—the attention makes him feel great, and he doesn't feel like such a loser for having no friends his own age. And as long as he keeps taking care of their cocks, they seem happy to spend time with him.
Jeremy stands on the sidelines and shakes his pom-pons as best he can while distracted by the vibrating pulses from his ass. At one point Toombs passes him and gives him a sharp, friendly smack on the butt. Once Jeremy had been annoyed by this kind of thing, thinking the boys were angry at him when they did so, but Toombs had explained that was one of the ways that boys showed they really liked a chick. So Jeremy had learned to be okay with it.
Practice lasts a long time, and Jeremy's not sure how much longer he can stand having the vibrator up his ass. It was a gift from the football boys, and Jeremy likes to use it when he can to show the boys how much he appreciates it. But it's been in him now ever since Tom slid it carefully up his ass before they came down here for the Saturday practice, and that was a few hours ago. The vibration is making all his muscles shaky, and at this point he's had to sit down to keep from collapsing.
Luckily, the boys seem to be finishing up. They huddle around together for some final words from the coach—which Jeremy can't hear—and then the coach announces loudly, "Alright. Hit the showers. I'll see you all after school on Monday."
The boys nod and call their assent, starting to drift down towards the school gym and the locker rooms. Tom, along with Toombs and two other boys, come towards Jeremy, smiling.
"Hey Squirt," says Tom. "How're you doing?"
"I feel weird," Jeremy admits. "Can I take out the, uh, the dildo now? Um, just so you can put your cocks in instead," he adds quickly, not wanting to disappoint. "I miss having all your cocks in me."
The boys grin. "Sure," says Toombs. "Let's just get you down to the lockers, and then we'll fuck you all you want." He puts a friendly hand on Jeremy's shoulder and leads him across the football field to the gym's side entrance.
When they reach the locker room, half the boys are already naked and in the shower, laughing and horsing around. They smile when they see Jeremy led in, and Jeremy can see that some of them are already hard.
Toombs leads him over to a bench between two rows of lockers and pushes him face down against the wood, lifting up his cheerleading skirt to reveal the tight white panties underneath. Instead of pulling them down, he just grabs the fabric covering up Jeremy's asshole and pulls it to the side, revealing the base of the vibrator as it squirms around inside Jeremy.
"Okay," says Toombs. "Our little chick wants to get fucked. Who wants to start?"
"I'm all soaped up," says one of the guys in the shower. "I bet I'd slide right in, with his ass all stretched out like that."
"Do it," Toombs invites. He reaches in with a thumb and forefinger and slowly slides the vibrator out of Jeremy's ass. After so long having it inside him, Jeremy gasps at the sensation of removal, his ass numb and tingling in the toy's absence.
Moments later, Jeremy feels the familiar slide of someone slipping his cock into Jeremy's asshole. His hole is indeed fairly well-stretched from the liberal massage of the sex toy, and parts easily for the boy as he pushes all the way home and begins to fuck Jeremy.
"Mm," says Jeremy, "that feels good." The boys have taught him that it's best to say nice things when he's being fucked—it makes them feel even better. "Can I have another one? I want two boys to fuck my ass."
"Sounds good." Jeremy's not sure which boy says it, but there are a number of them around him now, and the boy fucking him withdraws long enough for a different boy to lie down on his back on the bench. A number of hands lift Jeremy up and pull his panties to the side, like Toombs had earlier, then lower him down onto the spear of the boy's cock. Jeremy sighs as he feels the dick slide up into him, before the hands press him forward, pushing him chest-to-chest with the boy.
There's a prying intrusion as fingers wriggle into his ass and ply it open, stretching him out and preparing him for the larger entrance to come. It's there seconds later, pushing into him, widening him until he feels the familiar ache of double-penetration, the two boys thrusting up into him in short, controlled bursts. Jeremy moans.
"Fuck me hard!" he manages to choke out; even after all this time, it's still a little difficult for him to manage two cocks in him at once like this. "Um, let me- let me suck you off!"
The boys oblige him shortly, and another boy comes to stand next to him, lifting Jeremy's torso up and tilting the boy's head to the side, thrusting his stiff member past the boy's lips, practically choking him with the suddenness of it.
Jeremy stays fairly still as the three boys fuck him. It's tough, and somewhat uncomfortable, but he feels proud knowing that he can do this for them, that he can handle as many cocks as any other chick, and makes the boys feel good.
"Heh. Want to see how much he can fit?" Jeremy recognizes the voice as Toombs's, but he's not quite sure what the boy means. "Oh yeah," he hears one of the other boys say. "Let's see how far his slutty little ass can go."
Jeremy's not sure what they're doing—he can't see anything past the belly of the boy fucking his mouth, but he feels the boys in his ass stop thrusting, although they don't pull out.
Suddenly, something more is pushing at his anus. He tries to shout in protest, but it is muffled by the penis stuffing his throat. He's not sure what's going into him, but it's stretching him wider than his body should go, and it hurts. The boys inside him groan at the extra tightness and pressure, and then suddenly the vibration starts up again, and Jeremy realizes what they stuck inside him.
The toy vibrates away next to the other two cocks as the boys go back to thrusting, driving home each time and scraping painfully over his insides. Jeremy wants to protest, but the boy in his mouth shows no signs of slowing, and continues to fuck his face with abandon.
"God, your lips look so hot stretched around my cock," the boy mutters, and like that, Jeremy feels one of the boys in his ass start to come. The orgasm comes in sharp, painful jerks, and leaves Jeremy's insides feeling hot and stained. Jeremy sighs in relief when the boy pulls out, but his respite is short-lived as another boy immediately takes his place.
By the time the third boy shoots a load of cum into Jeremy's ass, Jeremy feels like he's finally starting to get used to the stretch of two cocks and the vibrator. It still hurts, but the vibrator is starting reduce his muscles to the same jellied numbness as before, and he no longer feels it as sharply.
As the boy in his mouth pulls out to come all over Jeremy's face, Jeremy hears one of the boys say, "Oh man, dudes, this. Come on, right?"
A lot of the other boys start to chuckle, but Jeremy can't open his eyes to see what they're talking about—his lids remain firmly closed as hot cum splatters across them and across the bridge of his nose.
"Fuck. Let us finish first," says one of the boys inside him, and Jeremy opens his mouth to ask what they mean. But he never gets the chance as another boy uses his open mouth as an excuse to slide inside, parting his lips and grabbing onto his hair for leverage as he replaces the previous boy, thrusting down Jeremy's throat.
Finally, the two boys inside his ass press their cocks deep, deep inside his anus and flood him with seed. "Fuck, that tight little ass!" one boy moans, and a few others chuckle.
"Alright," says someone. "Put him on his back."
The boy in Jeremy's mouth withdraws, and Jeremy is unceremoniously hoisted up from the bench, cum dripping from his anus as the boys' cocks slip out of him. The vibrator still buzzes away inside him, but it seems tiny now compared to the previous stretch.
Not for long, though—Jeremy's eyes widen as he sees what they have in store for him. One of the boys has apparently retrieved a wooden baseball bat from the equipment closet. He grips the handle tightly and grins.
Half a dozen boys gather around Jeremy. Some grip his legs, spreading them open. Others go directly for his anus, shoving their fingertips inside and stretching him as wide open as he can, shifting the dildo upward to make room. Jeremy is still wearing the panties, and someone else's hand is holding the now cum-soaked fabric to the side as the boy holding the bat lines it up with his ass.
Jeremy gasps as they start to push the baseball bat into him, then loses sight of what they're doing as the boy who had been fucking his face returns to the task. Any other sounds Jeremy would make are lodged in his throat under the pressure of the returning cock, and he can do nothing but feel the stretch as the bat is forced slowly further and further inside him, prying him open and grinding against the vibrator still lodged there, whirring away.
Jeremy's not sure how much of the baseball bat they actually manage to get inside him, but it sure feels like a lot. He lies there under the thick feeling of penetration and fellates the boy in his mouth the best he can, under the circumstances.
The boys are not content to merely let him be, however. He feels their fingers running experimentally around the edge of his chock-full anus, teasing the tight ring of flesh, seeking for and occasionally finding ways to slip a fingertip up inside. Meanwhile, several others gather around his face, using their hands and Jeremy's own to jerk themselves off, coming in spurts across his face.
The bat stays buried in his ass while Jeremy services the rest of the team with his mouth. Some come back for seconds, and Jeremy's stomach starts to roil from the amount of cum he's ingested.
Some other boys grab up the fabric of his skirt and use the material to rub themselves off. "You look so hot as a cheerleader," one of the boys says. "Such a cute little fuck-slut, cheering us on like that."
"Fuck, Toombs, can he keep this?" Tom asks. Tom is currently one of the boys using the skirt to jerk off.
"My sister's gonna want it back," Toombs says, sounding disappointed.
"Not covered in jizz, she's not," laughs one of the boys, and another one says, "Fuck that. Tell her you destroyed it in the laundry or something and buy her a new one. We gotta fuck him in this more often."
"Hah. Maybe," says Toombs.
"Fuck. FUCK." Says another one of the boys, standing on the sidelines. "I can't take it anymore. Take the bat out. I gotta fuck his ass. I have to, at least once while we're here."
The boy in Jeremy's mouth starts to come, not pulling out but instead just coming and coming and coming down Jeremy's throat, pouring the semen into him. There's a harsh, heavy slide as the baseball bat is drawn out of him, leaving his anus sore and throbbing, still dripping cum from earlier around the buzzing base of the vibe.
"We do have to get home in time for dinner, guys," says Tom as Jeremy feels another boy slide into his stretched-open ass and start to thrust.
"We've got at least another hour or two," says Toombs. "Come on, don't be a spoilsport! We should see what else we can find in the equipment closet."
"I guess," says Tom. "You still okay, Jeremy?"
Jeremy starts to answer, but is cut off by another cock slipping past his lips.