When Casey realizes that he has the wrong uniform, it’s too late to do anything about it. It’s the morning of his first day at St. Stephen’s, a co-ed Catholic school in the new town he and his mother just moved to. She gets up very early in the morning to go in for her shift as a nurse, and so Casey is alone the morning of his first day, getting himself ready, when he opens the package containing his school uniform.
His mother had told him that he should probably open it sooner to check and make sure that all the new clothes were the right size, but he’d put it off and just hadn’t gotten around to it. Now, as he pulls out the skirt and high-socks from the brown wrapping paper, he wishes he’d listened. It’s not the first time people have mistaken him for female; his name is gender-neutral, and besides that it seems that puberty hasn’t hit him as hard as his peers. Where most other 16-year-olds have been beefing up, growing hair in all sorts of places, Casey’s face still clings to a soft, boyish roundness, the hair on his arms and legs still pale and fine. Although he wears his hair short, curling around his ears, he still finds himself addressed as “Miss” by strangers more often than not.
Casey is torn about what to do regarding the uniform. On the one hand, if he doesn’t get dressed soon, he’s going to be late for his bus. And if he misses the bus he misses his first day of school, since there’s no one to drive him. On the other hand, he’s not sure he has any appropriately formal clothes that he can pick out from the closet, especially since everyone is supposed to be wearing the school’s uniform.
He’s not sure what impulse makes him try on the skirt, just to see. He looks at himself in the mirror, watching the way it hangs mid-way down his calves in careful pleats, and makes the reckless decision to go with it. Heck, why not. They’re the ones who sent him the uniform. Why shouldn’t he wear it?
He grabs the lunch his mother set out for him and makes it to the bus stop without trouble. The bus driver looks bored, but smiles a tired smile at him anyway, jerking a head towards the seats in silent welcome. Casey moves to an unoccupied seat and smooths the skirt under himself before sitting down.
When he gets to the school he’s handed a folder of papers at the main office that include his schedule for the day and a map of the school building. It’s the middle of the year, so he’s the only new student in the school, and he feels awkward wandering his way through the halls, glancing back and forth between the map and the numbers on the door, amidst the flood of more confident, practiced students streaming towards known destinations. No one looks twice at his skirt. Casey feels breathlessly like he’s getting away with something, like he’s a spy in hostile territory.
When he finally finds the room for his first class of the day, the nun in charge looks at him, then frowns down at a paper on her desk. “Hm, you’re Casey?” she asks.
Casey nods. “Yes Sister.” He keeps his voice soft and demure. That too is an area in which puberty has not hit him particularly hard; his voice is still unusually high. Nevertheless, it wouldn’t do to push his luck.
“I thought-” the nun starts, but then shakes her head. “Must have been a mistake. Welcome, Casey. Have a seat in the back there, in that empty seat next to Marcus. He’s the one with the curly hair.”
Casey does as he’s told, slinging his backpack down by the foot of the new desk. As he does he sees Marcus smiling at him. The boy gives a little wave with just his fingertips. Casey waves hesitantly back.
When the nun starts class—Sister Gertrude, according to Casey’s schedule—she gestures back to Casey. “Everyone, this is Casey Green, she’s going to be joining our school as of today. I trust you’ll all make her feel welcome. If she needs any help keeping up with any of her subjects, I want you all to be true to your faith and be kind and helpful. Remember, you are representing this school and this community with how you behave. Got it?”
“Yes Sister,” chimes the class. The nun nods and has everyone open their textbooks, and class begins.
First period is math, far too early in the morning to think so hard, but Casey toughs it out. They’re actually a little behind where he was in his previous school, so he’s not that worried. He follows along well enough, and when the bell rings for the end of the period he’s cautiously optimistic about his chances here.
“Hey there,” comes a voice as he packs up his things to head to the next class. “Where are you headed next?”
Casey looks up to see Marcus, the boy who he’d been sitting next to, standing over him, slightly closer than is comfortable. With an awkward start, Casey abruptly remembers the skirt he’s wearing; he’d forgotten all about it over the course of the class.
“Umm,” says Casey, looking back down at his schedule. “English? Sister Margaret?”
Marcus beams at him. He’s cute, in a teenage sort of way; a certain cocky confidence practically oozes from his stance. “Hey, me too! Want me to show you the way?”
“Sure,” says Casey, glad to have a guide through the unfamiliar hallways. When he stands and pulls his backpack back up to a shoulder, Marcus reaches out a hand to shake. “I’m Marcus, by the way,” he says.
“So I heard,” says Casey, which makes him smile wider.
When they get out into the hallway, thronging with people, Marcus puts an audacious hand around Casey’s shoulders and pulls Casey in towards him. “Be careful,” he says. “A lot of people don’t watch where they’re going. Wouldn’t want anyone to bump into you.”
Casey’s eyebrows raise, but he doesn’t say anything. He lets Marcus keep him pulled in close as the other boy steers him through the halls. When they get to English, Marcus pauses behind him while Casey introduces himself to Sister Margaret, and then walks him back to once again sit beside him. He gives Casey’s shoulder a little squeeze before he takes his own seat.
English goes not quite as well as math, but still nothing Casey can’t handle. When Marcus asks to see his schedule again at the end of class, his mouth pouts in disappointment. “Bible study? I have science next. Ah well. I guess maybe I’ll see you later today? Look for me at lunch—you can sit with me!”
“Uh, sure,” says Casey, and watches as Marcus darts out of the room with an enthusiastic wave.
“Don’t,” says a voice beside him. Casey turns his head to see a young woman with long brown hair braided in two neat plaits.
“Huh?” asks Casey in confusion.
“Marcus,” the girl clarifies. “Don’t encourage him. I know he seems friendly, but he’s tried this with literally every girl in school. He’s a sex fiend. He’s gonna try his damndest to have sex with you, and once he gets what he wants, he’ll just drop you like a hot iron and spread rumors about you to boot. It wouldn’t be the first time. Just be careful around him.”
“Uh, thanks?” says Casey. He’d gathered that Marcus had been flirting with him, but the idea that he might want to have sex somehow hadn’t crossed his mind. He’s never had a boy look at him that way. It sends a powerful creep of heat through his body. At his previous school his soft, feminine looks had been an object of scorn, something that got him beaten up. He’s never been in the position of being an object of desire before. The power of it has an intoxicating thrill.
The girl nods at him and leaves, leaving Casey to find his own way to his next class. The day continues uneventfully. At lunch, Marcus waves him down as promised and Casey eats lunch with him and some of his buddies. Now that he’s had warning of it, Casey notices the way Marcus is constantly looking at him out of the corner of his eye. Some of his other friends are sizing Casey up as well, looking between Marcus and Casey as if mentally setting odds.
The last period of the day is study hall in the school’s auditorium, and once again Casey has it with Marcus. The other boy sits next to him and, as soon as class starts, leans over and whispers in his ear. “Hey, wanna see something cool?”
Casey raises an eyebrow curiously, and Marcus winks at him before getting up and going up to the woman at the front of the room -- not a nun, possibly one of the school’s secretaries or something, just there to keep an eye on the students. He speaks softly, so Casey can barely hear him, but Casey is close enough to the front of the room that he can just make out the words.
“Mrs. Enbach, the nuns asked that I show Casey around the school so she knows where to find her classes for the rest of the week. Would it be okay if we took the study period to do so?”
Mrs. Enbach barely looks up from some papers on her desk and waves a hand. “Mmhmm,” she says.
Marcus grins back and Casey and gives him a covert thumbs-up. He gestures for Casey to pick up his backpack and, surprised, Casey follows him out of the room.
“Isn’t that wild?” Marcus asks when they get into the hallway. “She basically lets me do whatever I want. I get to spend the last period of the day wandering around the school if I want to. Sometimes I even leave early! Come on.” Marcus leads the way confidently down the hall, and Casey feels compelled to follow along in his wake.
Eventually Marcus leads them into a classroom. When Casey enters behind him, he sees that it’s empty; clearly this room isn’t used for anything for the final period of the day. Casey gets a nervous, fluttery feeling in his chest as Marcus leads him to the center of the room.
They come to a stop, each leaning against a desk, facing each other. Marcus doesn’t say anything. Eventually, to break the silence, Casey says, “So, what did you want to show me?”
Marcus lurches forward and kisses him, hard and demanding. His hands go to Casey’s hips, grasping them with a firm insistence. Casey feels his legs shaking with a terrified sort of triumph.
When they break apart, Marcus is leaning hard enough against him that Casey can feel the firmness of Marcus’s erection rubbing against his leg. “You’re really pretty,” Marcus whispers, voice rough. “Do you realize how pretty you are?”
“Uh,” says Casey, unsure.
“A girl like you, who’s so pretty and so nice, I bet she’d love to make a boy feel good, huh?”
It’s such a ridiculous line that Casey almost laughs, but the sound doesn’t come out around the furious pounding of his heart. This is insane. This whole situation is insane. But if Casey doesn’t do something soon then Marcus is going to notice his erection through his skirt and then the ruse will be up.
Casey pulls back as much as he can with Marcus trapping him against his desk and clasps his hands demurely in front of his own crotch, trying to tuck himself back as subtly as possible. “Oh, I, uh... that’s really flattering, but...” his mind races for an excuse to get himself out of the situation. “I’m a virgin, and I’m saving myself for marriage, so...”
Marcus’s smile doesn’t fade. One of the hands on Casey’s hips drifts around behind him to the small of his back. Casey feels curious fingertips dip below the waistline of his skirt. “Oh, I understand,” says Marcus. “We don’t have to have sex. I wouldn’t dream of taking a girl’s virginity before marriage like that. But, you know, there are other places I could put it that would feel good. Places it wouldn’t count.”
‘It damn well still counts there!’ Casey thinks but doesn’t say as Marcus’s probing fingertips slip along the crack in Casey’s buttcheeks, leaving little ambiguity as to his meaning.
“I could just slip it right in,” Marcus continues. “You wouldn’t have to get naked or anything. I wouldn’t even have to see your precious treasure.”
A questing fingertip finds the tight ring of Casey’s anus and pushes firmly against it, sending little lightning shots of pleasure all through Casey’s body. Casey gasps. Marcus kisses him again and pushes his finger harder against Casey’s asshole, making him squirm.
When they break apart, Casey knows he needs to get out of this particular position; he’s getting really hard now, and Marcus is bound to notice. “Won’t- uh, won’t that hurt?” he asks, his voice going high and squeaky.
“Not at all,” says Marcus, and blessedly steps backwards. He goes to his backpack and leans down, fishing around in a back zippered pocket. When he comes back up he’s holding a small tube of lube. “I came prepared. I can make it totally not hurt at all.”
Casey thinks back to the girl who tried to warn him earlier in the day. She was completely right; clearly Marcus is well used to this particular plot. He tries one last-ditch excuse. “Um, but, don’t you need a condom?”
Marcus smiles. “No need for a condom if it’s not sex, right? Can’t get pregnant from this. Just turn around. I swear, I won’t even undress you. Okay?”
Casey swallows. His legs are still shaking, and now his hands too. He turns around and grips the edge of the desk. His skin feels hot, like it’s on fire. He says nothing.
He feels Marcus come up behind him, hears the snap of the cap on the lube bottle. Then the hand returns, snaking under the waistband of his skirt, beyond his underwear. And then there’s the fingertip again probing at his tight pucker, but this time it’s slick with lube. Casey gasps and then grits his teeth as the slimy digit worms inside him, wriggling as though trying to find purchase.
“There,” says Marcus. “Feels good, right?” Casey doesn’t respond.
Marcus wiggles the finger around for a while. Then he takes it out for a second. The lube bottle makes a little slurping sound. The hand returns, and this time two slicked fingers pry their way into Casey’s hole, pushing in and out in a little rhythm. Casey shifts slightly, reaching for a heat that he already feels pooling inside him. As he does so, Marcus’s fingers brush against something inside Casey that make him jolt and go rigid. He can’t quite suppress the little moan that wrings its way out of him.
“You like that, huh?” Marcus’s voice is amused, with a healthy dose of smugness. Casey doesn’t trust himself to speak. Marcus rams his fingers in again, hitting the spot once more and causing Casey’s body to spasm.
“Okay,” says Marcus, “here we go.” The fingers disappear and Casey hears the bottle of lube again. He also hears the sound of the zipper on Marcus’s pants. A shudder of nerves runs through him.
“Here, move like this,” says Marcus, and Casey feels Marcus’s hands once again on his hips, lifting him slightly and bending him over the desk. It puts Casey just high enough that his feet don’t quite touch the floor. Marcus’s hands move to the waistband of his skirt once more, and Casey feels him tugging at it, pulling it down along with Casey’s underwear to expose the small of his back and the top of his buttocks.
As promised, Marcus pulls the skirt down only just barely enough to expose Casey’s asshole to the open air. The bit of lube smeared around the outside of the hole feels cold in the sudden exposure, a light tuft of sensation that makes Casey’s asshole twinge. He hears Marcus chuckle.
“Looks like you’re ready for it, huh?” he boasts. “I could tell you’d be into this, as soon I saw you.” He pauses. One hand returns to Casey’s backside, this time directly on his buttocks, spreading him open. “Here we go,” Marcus says again, and Casey feels a large object positioned just outside his entrance.
As Marcus pushes into him, it feels like being peeled open. The boy’s cock parts him with demanding insistence, shoving its way into the passage inch by enormous inch. It feels unbelievably, impossibly large. It slides forward with an inevitability, gliding smoothly on the lube, spreading him open with unforgiving force.
By the time Marcus is fully seated inside of him, Casey feels like he’s choking on the boy’s cock in the back of his throat, it’s so deep. He groans and Marcus starts to thrust, quick and hard.
The boy has both hands on Casey’s hips again, holding him steady as he drives over and over into the boy’s ass. Casey chokes on the sounds he’s making, the feeling of fullness, wanting it to be over and not to be over as Marcus fucks into him hard, again and again and again.
Marcus says nothing, just making his own occasional grunt. The thrusts are uncomfortable for Casey, but he doesn’t say anything either. Everything in his mind is too focused on the cock inside him, the relentless pressure of it, the constant frantic pounding that stretches his rectum open. It’s so impossibly deep in him, filling him, stretching him so impossibly wide open, that he feels like he’s going to die. There’s no way he can survive this sensation, as Marcus continues to fuck him. He’s going to die impaled on this boy’s cock.
Marcus, luckily, is sixteen and therefore doesn’t take long. Less than five minutes after they started, Marcus drives deep into him and Casey feels the shuddering of Marcus’s balls against his ass as he comes, emptying himself inside Casey’s body. Afterward he slumps forward, pinning them both to the desk.
They breathe together in silence for a few moments until Marcus’s erection finally softens enough to pop out of Casey’s ass, leaving a trickle of wetness behind it. Casey feels Marcus pat his ass in a sort of “well done” gesture, and hears the boy’s zipper again as he puts himself away.
“Nice,” he hears Marcus say. Casey is still face down on the desk, unable to move. His own erection digs painfully into the side of wood. “I told you it would feel good.”
He hears Marcus pick up his backpack and, as Casey turns his head to look over his shoulder, sees the boy leave the classroom without even bothering to pull Casey’s skirt back up. Well, at least he’d closed the door behind him.
Shuddering, Casey gingerly lets himself down from the desk and limps to the teacher’s desk where there is a box of tissues perched on the edge. He grabs a few and reaches behind himself, soaking up Marcus’s cum as it starts to leak out of him. Then, leaning back against one of the desks in the front row, he pulls his skirt down far enough to free his own cock and pumps it, hard. It takes only a few desperate tugs for him to come hard, spilling into another tissue.
Casey takes the last few minutes of class to make himself presentable, straightening his skirt and making sure his hair doesn’t look too messy. When the bell rings he’s ready to make his way out to the buses with, he hopes, no visible evidence of how he spent the last class period.
When he gets home, Casey washes his uniform and tucks it away neatly in his closet before his mom even gets back from work.
The next day, Marcus doesn’t even talk to him. Casey is stunned by how accurate the girl’s warning from the day before was. It’s like the boy doesn’t even know he exists. Casey doesn’t know how to feel about that; he’s too embarrassed about what happened to try and talk to Marcus anyway. Maybe it’s best to just leave things be.
At lunch Marcus’s friends wave Casey over once again, but Marcus himself says nothing. The seat next to him isn’t open, and so Casey sits next to one of Marcus’s other friends and makes smalltalk.
Three days of this go by, and Casey is beginning to wonder if maybe the experience wasn’t as good for Marcus as Casey had thought. It would have to be though, right? How could it not have been?
And so he’s startled when, three days after Marcus fucked him, the boy leans close to his ear in last-period study hall and whispers, “Same classroom as last time.” He jerks his chin towards the teacher. “She’ll let you go if you ask.”
Heart pounding, Casey stands and walks to the front of the class. He smiles at the teacher. “One of the nuns asked if I would help her clean her classroom this period,” he lies. “Is it okay if I go?”
The teacher nods and waves a distracted hand, and Casey turns and grabs his bag. As he walks up the auditorium aisle, he sees Marcus give him a little thumbs-up.
Casey goes to the classroom and waits nervously, once again leaning against a desk in the center of the room. He’s not waiting long before the door opens cautiously, and curious head peeks into the room.
It’s not Marcus. With a start, Casey realizes that he hadn’t seen Marcus get up to follow him out of the study hall. This is one of Marcus’s friends; someone Casey has seen at lunch but never talked to directly. He’s a tall boy, a little on the pudgy side, with messy black hair and mean eyes. He slips into the room and closes the door behind him.
With unearned confidence he stalks up to Casey and comes to a stop right in front of him. “Marcus says you’re a slut,” he says abruptly. “Why don’t you turn around and let me fuck your ass?”
Casey nearly laughs. For what little can be said of Marcus, at least he was smoother than this. Casey doesn’t even know this boy’s name. Casey raises an eyebrow, but to his surprise the boy just unzips his pants and pulls out his erection, gesturing a little circle with his hand in a ‘turn-around’ motion.
Casey is so shocked he doesn’t even think about what he says next. “Where’s the lube?”
“Lube?” The boy frowns.
Casey rolls his eyes. “Yeah, lube. Marcus had lube. It won’t go in without it, dingus.”
The boy looks impatient. “Fuck, whatever. Of course he did. Fine, here.”
Casey has no time to react before the strange boy has grabbed his head and shoved him downward, onto his knees. The boy uses his grip on Casey’s hair to yank him forward, mashing Casey’s face into the boy’s exposed cock.
“What the fuck?” Casey manages.
“Suck it,” the boy orders. “That’s lube enough.” Without waiting for a response he shoves the head of his dick towards Casey’s lips. Casey is startled into opening his mouth, and the boy rams his way inside, causing Casey to choke.
The boy holds Casey’s head steady, and Casey has no choice but to start sucking. He laves at the boy’s member with his tongue; if it’s going to go up his ass, he’s going to at least be sure it’s good and wet. After a few moments the boy’s hand leaves the top of his hair and both hands come up to the side of Casey’s face, holding him steady while he fucks into Casey’s mouth a little.
It’s humiliating, being on his knees with this strange boy’s cock shoved down his throat, but something about it still sends tingles to Casey’s groin. He can feel himself growing hard again as the strange boy pulls Casey’s head onto and off of his cock. He tries hard to breath through his nose and concentrate on lubing the cock as much as he can with his tongue.
When the boy abruptly yanks Casey’s head off his dick a few minutes later, Casey has just enough time to choke out, “You have to promise you won’t pull my skirt down! I’m saving myself for marriage! Only enough to get it in behind, got it?”
The boy snorts and man-handles Casey onto his stomach on the desk, just like he was before. But he seems to follow instructions as he pulls down the waistline of Casey’s skirt and underwear just a little bit, just enough to expose his asshole.
There’s no foreplay this time. The boy shoves his cock right into Casey. No easy slide from the lube this time either; the spit-wet cock catches roughly as the boy drives hard into him, and the scrape of it is painful. But the boy persists, shoving himself deeper in short, harsh bursts that each bury an additional inch inside him. Casey gasps as the strange boy finishes seating himself fully inside Casey’s ass.
“See?” says the boy. “Goes in easy. Who needs lube?”
Casey groans as the boy begins to fuck him. His thrusts are harsh, savage, and Casey’s own erection digs painfully into the top of the desk as the boy plows him. The spit does just enough to make the movement possible, but not easy. Casey grits his teeth.
With one hand on Casey’s hip, the boy reaches up with his other hand and grabs Casey’s hair, yanking his head back as he swivels his cock in and out of Casey’s hole. “Good slut,” he growls. “You’re loving this, huh? You like taking a big fat cock up the ass like this, huh?”
‘Not exactly like this,’ Casey thinks, but doesn’t say anything. Like Marcus, the new boy doesn’t last very long. He pulls hard on Casey’s hair as he comes, filling Casey with jizz. He lets out a long, grunting sigh as he does so, like an animal.
As he pulls out of Casey’s ass, leaving him dripping on the desk, Casey hears the boy chuckle. “Just like Marcus said,” he says. “Hey, how about next time I come back with a friend, huh? Plow you from both ends? Plenty of holes on you we can use without worrying about your precious virginity.”
He hears the boy laugh and put himself away, hears his footsteps as he walks out of the classroom. When he’s sure the boy isn’t coming back, Casey wincingly works his way off the desk and back towards the tissue supply. His erection strains at his underwear, tenting the front of his skirt.
Next time, he will definitely be bringing his own lube.