A month into his tenure at St. Stephen’s Catholic school, Casey is beginning to despair at the school’s lack of ability to teach very basic human anatomy.
It’s not the fact that Casey’s classmates don’t recognize him as a boy when they fuck him in the empty classroom at the end of the school day. After all, at this point he’s gone to great lengths to keep his cock from being discovered. At first, he tried to keep it taped down to avoid erections, finding videos online of drag queens explaining how to do so. But this process had been painful, and not as discreet as Casey had hoped. So instead he had stolen his mother’s credit card and made a furtive purchase online.
The afternoon of waiting by the front door for the mailman had been nerve-wracking, trying to intercept the package before his mother got home. But now he doesn’t worry about getting erections while he’s fucked, as his penis stays politely nestled in its discreet, stainless steel cage. The success of this purchase has also led him to purchase a padded bra with small silicone inserts, to better give the impression of newly-burgeoning breasts.
So it is not the boys’ lack of ability to discern his gender that worries Casey. It’s their complete lack of understanding of how lubrication works.
After his second encounter in the empty classroom, rough and unexpected, with only spit for lubrication, Casey had purchased his own lube and started bringing it to school with him. But after two more sessions with new boys coming in—their inability to judge the amount of lube and their impatience with stretching him causing Casey a great deal of discomfort—Casey decided the only way for this to be feasible was for him to apply the lube himself.
So each afternoon, after making an excuse to leave the study hall where he’s supposed to be spending the last period of the day, Casey makes his way to the girl’s bathroom and closes himself into a stall to lube up.
He’s gotten it down to a fairly quick process, lubing his fingers and stretching himself open, making sure he’s clean and relaxed enough for a thorough fucking. The thought of what is about to happen to him turns him on like crazy, but his little cage keeps him from getting hard and ruining his disguise.
Despite Casey’s now-practiced speed with this process, the other boys are usually already there in the classroom when he arrives. It’s not the same boys every time; some boys don’t have classes they can get out of every day, some aren’t interested as often, and in general most have to take turns anyway; there are only so many people Casey has time to service in a single school period. But he seems to be steadily working his way through the male population of St. Stephen’s, nevertheless.
What’s ridiculous about the lubrication is that, now that they don’t have to apply it themselves, the boys seems to think it’s natural. Now, nearly every day when the first boy slides his dick into Casey’s well-prepared asshole, he’ll make some comment like, “Wow, you’re so wet, you’re clearly dying for it” or “You really want my cock so bad, huh? Look how honest your little hole is, it’s already leaking.”
Do they not understand that the anus doesn’t self-lubricate, even on women? Or do some of them not even realize that they’re using his anus, and not a vagina? He supposes he should be grateful that they even seem to have a concept that lubrication is somehow associated with a woman being turned on. How is it possible that they haven’t at least seen enough porn to know how an asshole works? Some of them even talk about his G-spot, and his clit, as though they have any idea what those things even are. Ah well. Their ignorance probably works in Casey’s favor anyway.
Casey leans over a desk in the empty classroom, surrounded by four horny teen boys, and pulls his skirt down the necessary few inches, wincing only slightly when one boy unceremoniously shoves a pair of fingers into his hole as soon as it is exposed.
He can’t help but smirk when the boy says, “Hah, look how wet she is! Her fuckhole is practically begging for it!” But his smirk fades quickly as he is forced to open his mouth for another boy stepping in front of him, presenting his penis at Casey’s lips. His slips his mouth onto the head of the young member as he feels the other boy behind him take out his fingers and replace them with an eager cock, sliding it into his anus. The lube and stretching preparation does its job, and the penis glides right into Casey with little resistance.
It’s become practically routine, at this point: the two boys fuck him hard from both ends, coming quickly after only a few minutes of stimulation. When they pull out, leaving Casey dripping with their cum, they are replaced by the other two so the initial boys have a moment to recover and clean themselves up slightly. Then, once the second pair have finished spraying jizz into him, the first pair are back and ready to swap holes; the boy Casey blew lines up his cock to shove into Casey’s ass, while the one who was in his ass before gets a blowjob.
The school periods at St. Stephen’s are 50 minutes long, and in general after the time spent preparing himself at the beginning of the period, there’s just enough time for four boys to each fuck Casey twice—once in each hole—before the period ends. Casey usually has just enough time to catch his breath, shove some tissues under his asshole to catch the cum as it drips out, and pull up his skirt before he has to race to catch the bus home.
As the last pair of boys for the afternoon plunge into his various orifices, Casey thinks somewhat wistfully about the late afternoon, when he’ll finally have a chance to take off the little cage and get himself off. He’s usually instantly rock-hard after un-restraining himself at home; the hour-and-a-half-long bus ride home after being heartily plowed is torture, and he can’t wait to give in after being turned on so bad for so long.
Luckily, the day is almost at an end. The last pair are fucking Casey in their second configuration, and the first pair has already left to get back to class. The boy in Casey’s mouth—Lucas, maybe, he thinks?—finally starts coming, pulling out as he does so to splatter Casey’s face with cum and chuckling over it. “You look real pretty like that,” he says mockingly. “Sorry you don’t get to swallow it though. I know how much you love that.”
He pulls his pants up and saunters over towards the door, leaving Casey’s line of sight. As the second boy rams Casey’s ass harder, pulling Casey’s hips back for leverage and pumping the contents of his balls up Casey’s backside, Casey hears probably-Lucas turn the door handle, and then a hissed whisper of, “Oh shit, scatter!”
The cock is yanked out of Casey’s ass abruptly, before the boy is even done coming. Casey, dazed by the sudden withdrawal, feels a last splatter of it hit his butt cheek.
He doesn’t quite understand what’s happening until he hears one of the boys say breathlessly, “Oh hey Mr. Ramiel, I was just leaving,” followed by hasty footsteps pounding down the hallway.
Casey looks over his shoulder with dread to find a young teacher, Mr. Ramiel, standing in the doorway and staring at him. Mr. Ramiel is a good teacher, a priest-in-training not yet ordained who teaches one of the history classes. He’s generally good-natured, but Casey doubts that good nature extends to watching one of his students get plowed in the ass.
Casey hastily straightens up, his hips twinging slightly in protest, and pulls up his skirt. “Oh, uh, Mr. Ramiel,” he says, putting on a face of false cheer. “W-what are you doing here?”
Mr. Ramiel’s face is difficult to read; he’s one of those teachers who uses dark humor in the classroom, and Casey can never quite tell if he’s joking. The man takes a few steps forward, closing the door behind him. He crosses his arms over his chest.
“I have to say, Casey,” he says, “I’m very disappointed.”
Casey grits his teeth and looks down at the ground. His face is still covered in cum. He starts to lean back against the desk behind him, but the pressure it puts on his sore rear end is slightly painful, so he straightens back up.
“As a faithful young woman,” the teacher continues, “you must know that your precious flower is the most valuable thing you have. Think how your future husband will feel, knowing that you let a boy take your virginity like that?”
Casey almost laughs, but keeps a straight face. Maybe it’s nerves, or the lack of blood going to his brain at the moment, but he hears himself say, “My ‘precious flower’ is fine. I only let boys do me up the ass.” He feels his face heating like crazy with embarrassment. “So, you know, I’m still a virgin. It’s fine.”
He risks a glance up to see Mr. Ramiel scowling. Maybe not the right answer.
“You make it sound like you’ve done this before,” says the teacher.
Casey mentally weighs his options. He doesn’t want to stop. He loves being fucked at the end of every school day. Despite the degrading way they talk to him, the attention he gets from the boys who come to plow him every day is intoxicating to Casey. It makes him feel wanted, powerful. And it turns him on like nothing else. And besides that, if Mr. Ramiel tells Casey’s mom what’s going on, then the ruse will be up. Casey has been able to keep this from her so far by virtue of the fact that her crazy hours as a nurse mean she’s not home when Casey leaves in the morning in his skirt, nor when he returns home in the afternoon. If they call her in to let her know that her ‘daughter’ was having sex on school grounds, then there are going to be a lot of awkward questions.
Casey bites his lip. He can think of one thing that might work. He’ll miss his bus, but to keep up this act, it’s worth it. He’ll figure out how to get home some other way. Maybe he can hitchhike; he’s heard that most drivers will accept blowjobs as payment.
Slowly, Casey turns back around so he’s no longer facing Mr. Ramiel, and leans back over the desk. “I promise, I don’t even let them look at my... treasure,” he says. He lowers his skirt again, as it was before. “All of their cum has gone down my throat or right up my asshole, I promise. You can... inspect it, if you want to.”
He hears a soft gasp from Mr. Ramiel, but doesn’t dare turn around. “This is... highly inappropriate,” the teacher says. His voice sounds strangled. Casey doesn’t reply, just wiggles his hips slightly in offering.
There is a painfully long silence. Footsteps approach Casey. He wonders if he’s about to feel hands pulling his skirt back up, and a no-nonsense voice telling him that Mr. Ramiel will be reporting this to the headmaster.
Instead, blissfully, Casey feels long fingers push into his anus. He groans in appreciation and relief. The fingers make a wet squelching noise as they slip up into his well-used hole. Casey feels himself being stretched open, feels the cum dribbling out of him around Mr. Ramiel’s exploratory digits.
“Oh,” says the teacher. His voice still sounds a little strained. “So I... uh... so I see... How many boys have...”
Casey smiles, feeling more confident now. “Oh, usually I get four boys a day in my mouth, and four in my ass. Not all at once, obviously. It's four boys who swap positions halfway through. We only have so much time in the period. They really seem to like it a lot, and, you know, as a good Catholic girl I just want to help the men in my life live their best, fullest lives. It’s my duty, after all, as a young woman. You can...” he licks his lips. “You can try it out for yourself, if you want. I just want to be a dutiful follower of the Lord.”
Maybe that’s laying it on a bit thick. But regardless, it seems to work; Mr. Ramiel inserts a third finger into Casey’s ass and starts ramming them in and out, finger-fucking the squelching, messy hole. “Obedience is a virtue,” he says after a moment.
“Absolutely,” says Casey. “That’s the only reason I do it. I’m not some harlot who gets pleasure from being... umm, from sex. I just want to help my classmates get out their... urges, so they’re not tempted to sin with other girls and get them pregnant.”
“What a good girl,” the young man murmurs, and then Casey feels the teacher’s penis slide into his ass. It’s bigger than he’s used to; noticeably bigger than the boys’. He chokes slightly as it pushes its way relentlessly deeper, deeper and deeper until Casey’s sure that there can’t be any more, it must be all the way in, but still it continues.
When he finally comes to rest, Casey has the feeling of being filled all the way through his body. Like if Mr. Ramiel were to come, it would come out of Casey’s mouth. He groans in pleasure, and twitches his hips backwards to encourage Mr. Ramiel to move.
The man takes the hint quickly. He sets a brisk pace, ramming forward with no mercy, plugging Casey again and again, filling him insanely deep. Casey can’t help but cry out as the larger, mature phallus of the teacher takes him over and over. He wishes desperately that he could get hard; it feels so good. He’s going to have to wank off the entire afternoon when he gets home.
Whenever that might be; Mr. Ramiel has already taken far longer than the average high school boy, and shows no signs of slowing down or stopping. Casey desperately swallows against the lump in his throat as he tries to keep track of the seconds ticking by based on the speed of Mr. Ramiel’s thrusts.
It feels like ages that he lies there on his stomach being fucked by the teacher. Mr. Ramiel says nothing, although eventually he does grab Casey’s hips to get better leverage. Casey wonders how long the man could possibly keep going as the pounding of his ass goes on and on and on.
Eventually, finally, Casey feels the familiar sensation of balls twitching against his ass, emptying their seed inside of him in powerful bursts. He smiles to himself. In the bag; now he has nothing to worry about. He squeezes his anal muscles as tight as he can to wring the last remaining drops of jizz from Mr. Ramiel’s penis.
Finally the man pulls out. Casey gives him a moment to get himself situated before turning around and pulling up his skirt, moving towards the desk for tissues.
“I... can see why those boys find this satisfying,” says Mr. Ramiel breathlessly. “It’s very kind of you to provide such a... service for them at your own expense like that.”
‘You should see my blowjobs,’ Casey thinks, but doesn’t say it. Instead he just grabs a few tissues and shoves them down the back of his panties as Mr. Ramiel’s cum starts to dribble out of Casey’s fucked-open ass and into his underwear. Now, on to logistical concerns... a thought suddenly occurs to Casey.
“Mr. Ramiel, you drive a motorcycle, right?” It’s a big topic of gossip at the school, as many girls find this to be an unbearably cool thing about the man.
“Yes, why?” asks the teacher suspiciously.
“Would you mind giving me a ride home?” Casey asks. “I’ll have missed my bus by now.”
He sees the teacher’s shoulders visibly relaxing. He wonders what the man had been thinking. “Oh, certainly. I suppose it’s only fair, since I’ve... inconvenienced you.”
“Thanks.” Casey grins and starts follows the teacher out the door with only a slight limp.
“Oh but,” Mr. Ramiel half turns around as they get to the door. “First you should probably wash the cum off your face.”
Riding Mr. Ramiel’s motorcycle is a kind of exquisite torture. The vibrations of the engine massage his sore, over-stimulated asshole with little lightning bolts of pleasure, while the firm body of the man in front of him reminds Casey of the way that body had felt ramming itself up inside him. By the time they get to Casey’s home, he’s more turned on than he’s ever been after a bus-ride.
When they pull up in Casey’s driveway (his mother’s car still not here yet, thank goodness), Casey dismounts from the vehicle with a distinct lack of grace and holds out Mr. Ramiel’s extra helmet for him to take back. “Thank you,” he says demurely.
“So, uh...” Mr. Ramiel’s voice is a little hoarse, and he clears his throat. “I was thinking about it, and living this far outside of town, you must have a very long bus ride to get to school.”
“Sure,” says Casey, not sure where he’s going with this. “An hour and a half, usually. Sometimes longer if traffic’s bad. Why?”
“Well...” Mr. Ramiel hesitates a moment, then speaks quickly. “I don’t live too far away from here, and I usually head in to school pretty early. If you’d like, I can pick you up on my way in. From now on, I mean. It would be much faster than the bus, and you’d get to school much earlier. That way you’d have plenty of extra time in the mornings when you got to school, which you could use to... um... study. If you wanted to.”
Casey’s heart pounds in his chest. “Oh, uh... sure. Yeah. That sounds really nice, actually. I always feel like I’m in a rush to get in before the bell in the morning. That would be... a relief.” He pauses, feeling more is expected of him. “...Thank you.”
“No problem,” says Mr. Ramiel with a relieved smile. “See you tomorrow then?”
“Sure,” says Casey. He swallows. “See you tomorrow.”
Mr. Ramiel’s office is very small, little more than a closet adjacent to his classroom. It’s also mostly filled with old textbooks and other junk. But there is a small desk and chair, and even an extra chair that Casey sits in when they arrive at the room the following morning.
Mr. Ramiel sits in his desk chair and stares at Casey awkwardly for a moment. They have over an hour before school starts. After a short silence, the man flushes and turns away to start typing on his computer.
Casey is surprised, but as Mr. Ramiel continues typing, Casey realizes that the man doesn’t know how to ask for what he wants. He’s literally giving Casey the opportunity to study, as promised. Hilarious. Or maybe he’s just giving Casey a moment to relax? Casey smiles.
He puts his bag down on the floor of the office and roots around in it. This is going to be tough to manage without being able to take his skirt down, but Casey is young and flexible. Besides, it can’t be that much worse than trying to do it while sitting on a toilet in a cramped school bathroom.
Casey’s hand finally closes around the tube of lube that he brings with him, and he draws it out. He generously lubes one hand and then closes the bottle with a snap, dropping it nonchalantly onto his bag. He notices that Mr. Ramiel has stopped typing, watching Casey out of the corner of his eye.
Casey turns around so he can kneel with one knee on the chair and reaches behind himself. With a practiced hand he reaches into his panties and deftly seeks out his own asshole, slipping a couple fingers inside himself. He works them in and out, taking his time since he has it. It’s a bit of a tough angle for him, so he can’t get as deep as he wants, but he’s still able to wiggle them around enough to get his muscles used to the feeling of penetration. With a happy sigh he adds the other two fingers, plunging his hand in and out and fucking himself with steadily-increasing abandon.
Mr. Ramiel has now given up the pretense of typing and has turned in his chair, staring at Casey. He licks his lips. “So, you do this... every day?”
“It’s important to be prepared,” Casey says with a smile. “You can take a look, if you want.”
Almost before Casey’s finished speaking, Mr. Ramiel reaches over and tugs down Casey’s skirt, watching with rapt attention as most of Casey’s hand disappears up inside his own ass. He’s practically drooling.
“I can’t quite get it as deep as I want though,” Casey admits, pointedly.
“Oh, well, maybe I can help you out then,” Mr. Ramiel says quickly.
Casey beams at him. “Would you?” He takes his hand out of his ass and gestures down at the lube.
Casey looks over his shoulder long enough to watch Mr. Ramiel lube up his hand, then turns around again to face the back of the chair.
“All four?” Mr. Ramiel asks, sounding uncertain.
“Yup,” says Casey. “Just like I was doing.”
Mr. Ramiel’s hand is bigger than Casey’s, but not by so much that it makes the stretch painful. The main advantage he has is leverage, and he’s quickly able to get his fingers all the way into Casey, up to the last knuckle. Casey groans at the full feeling. Mr. Ramiel wiggles his fingers inside Casey’s rectum.
“Yeah, now thrust,” says Casey, his voice strangled. “Like you’re fucking me. Get me good and loose.” He wonders if Mr. Ramiel will say something about his crude language, but the man just does as he’s told and begins to fuck Casey with his hand.
This time, Casey is in a position where he can see the clock on the wall, so he can watch the time pass as Mr. Ramiel dutifully rams his fingers up Casey’s ass over and over. It’s intense, but not the feeling of depth he’d gotten from yesterday. Still, he’s not complaining. Gradually, his ass relaxes into the feeling, welcoming the teacher’s fingers into him like they belong there.
After nearly ten minutes of this, Mr. Ramiels says, “You seem pretty relaxed now. I bet I could fit my whole hand.”
Casey gasps at the boldness of it. This is starting to get even beyond his fantasies. He bites his lip, but before he can decide whether he wants it or not, Mr. Ramiel is already pulling his hand out a few inches and then sliding it back in with his thumb accompanying.
The pressure is intense, but Mr. Ramiel is slow and relentless. Casey whimpers as the intense feeling of pushing against his hole increases, increases until he doesn’t think he can bear it anymore, and then suddenly there’s a slip, a slide, a jolt forward and Mr. Ramiel’s hand pops fully into Casey’s ass.
The teacher seems as surprised as Casey, and is unable to stop himself before he’s shoved a couple more inches up inside the boy. Then he stills, just letting his hand rest inside Casey’s passage. Casey whimpers, feeling stretched to the point of insanity. He can feel his own rectum spasm around the intruder, clutching it tight.
He hears Mr. Ramiel chuckle, and it doesn’t sound nearly as shy as before. The man starts to move, never drawing his hand all the way out, but thrusting with it in short bursts before periodically writhing it around inside him.
Casey can’t help crying out, especially as the knuckle of the man’s thumb brushes his prostate. He squeals at the sudden jolt of pleasure and rocks his hips, trying to get more.
Mr. Ramiel obliges him, fist-fucking him over and over, getting settled into a rhythm until his hand brushes Casey’s prostate every time. Casey is desperate, moaning and writhing on the man’s hand, completely losing himself in the sensation. He can feel pressure building inside him, the pleasure filling him like a vessel, and he wants to come so, so badly.
And then he does. Despite the cage, Casey feels his balls spasm and fluid spurt out of his restrained cock, staining his panties. It’s a relief, but not the full relief he wants, and Casey cries out in a mix of ecstasy and frustration.
“Shhhh,” Mr. Ramiel pets his hair. “Not too loud. There are other people in the building already...” He begins to pull his hand back, and Casey lets out an involuntary groan as the widest part pops back out through his ring of muscle before the blissful fullness disappears altogether.
“I dare say you’re pretty well prepared to ease a man’s suffering now,” says Mr. Ramiel. “Shall we check to make sure?”
Casey has barely time to draw in breath to ask Mr. Ramiel what he means before the man’s penis is sliding into him. It’s not the insane size of the teacher’s fist, but the man certainly knows how to use it. He sets a bruising rhythm, fucking Casey hard and deep. Casey gasps and tries as best he can to thrust his own hips back to meet the welcome intruder.
Mr. Ramiel pauses for just a moment to move Casey, taking him off the chair and leaning him up against the teacher’s desk before plowing into him once more with renewed vigor. Casey glances at the wall clock and sees that they now have only around half an hour before he has to get to class. He closes his eyes and focuses on ramming, brutal thrusts of the teacher’s cock going into him. It’s going to be tough for the boys in the afternoon to compete with this.
Once again, time seems to stretch on and on, even as Mr. Ramiel’s cock stretches Casey’s hole. Casey loses track of time in the slick pounding, feeling only the delightful ramming home of every delicious thrust. He opens his eyes again as Mr. Ramiel finally comes, squirting him full of jizz, and looks at the clock. Took only 25 minutes, this time.
Mr. Ramiel leans on Casey’s back for a few moments, breathing heavy and pinning him. Casey feels the man’s cock soften and pop out of him, the flow of cum immediately dribbling down Casey’s crack under the edge of his skirt and onto the back of his still-covered and very blue balls.
Finally the teacher straightens up, and even helpfully pulls Casey’s skirt back up. He gives Casey’s butt a proprietary pat. “Thank you so much, Casey, for your help. Maybe next time we’ll try that mouth of yours that you mentioned?”
Casey smiles, a little shakily. He leans on the desk, not sure he can stand on his own. “Sure. I’d be happy to.”
“Go get yourself cleaned up,” says Mr. Ramiel. “School starts soon.” Casey makes his slow, limping way to the girls’ bathroom.
When he gets there, he curses the fact that he doesn’t have enough time to uncage himself and get off before the first bell of the day. He’s so turned on he’s sore with it, aching. He wipes the inside of his thighs down with toilet paper and wipes his panties as free of jizz as he can before shoving some tissues against his ass to absorb the rest of the mess. He’ll have to find some time during the day to sneak back in here and get off.
After all, if he’s going to be getting fucked by his teacher every morning and his classmates every afternoon, he’s going to have to get used to having a very full school day.