Another year, another birthday. Tommy turns seventeen the day his father shows up unexpectedly early in the morning. The man looks unusually well put together in a nice suit and gel-slicked hair. Tommy is immediately on edge, uncertain what’s about to happen.
His father eyes him critically up and down. “You prepped yet?” he asks gruffly.
Tommy swallows. He shakes his head. He wasn’t expecting anyone this soon.
His father scowls. “Well, hurry up and do it then. We’re on a timetable.”
Tommy knows better than to ask for more details at this point. He hurries to the bed and shucks off his pants, grabbing up his lotion from the nightstand. A few pumps of the handle and his palm is full of white cream. He hurriedly spreads it onto his fingers and reaches around behind himself.
He’s no longer embarrassed by now; his shame is a mere dull ember under his heart as his father looks on while he lifts one knee onto the bed and reaches behind himself to penetrate his hole with slick digits. His father crosses his arms with impatience as Tommy spears himself with two fingers and begins to work them in and out with a steady rhythm.
He tries to be quick about it, sticking his fingers in deep and stretching them apart as he works himself open, but even so he feels like he’s barely started before his father snaps at him. “That’s plenty. Come on, we have to get going.”
“Going?” Tommy asks, astonished, as he pulls up his pants. Where would they go? Tommy almost never gets to leave the rectory. The only exception is his three-times-a-year physical with the doctor that his father has found to check him over for STDs and then fuck him afterwards as payment, and he’s not due for another checkup for at least a month.
His father doesn’t respond, instead handing Tommy a pair of shoes to put on. This too, is new; there’s usually no footwear for him in the apartment, possibly as a measure to discourage him from escape attempts. Not that Tommy has tried; his first disastrous attempt to run away got him into this whole mess to begin with. He’s not eager to go through something like that again.
He puts on the shoes—they’re slightly too small for him, he’s definitely grown since his shoe size was last measured—and follows his father to the door.
Once outside, his father grabs him by the wrist and leads him to the car. Tommy follows obediently, strapping himself into the passenger seat. He’s on high alert; at this point he’s learned not to expect anything good from sudden changes. Even the most cautious optimism is seldom rewarded.
They drive for over half an hour, to a part of town that Tommy’s never seen before. The area is full of neon lights but it looks surprisingly high-class, with tree-lined streets and a variety of fancy hotels. This impression is confirmed when Tommy’s father stops the car in front of a building and is greeted by a parking valet who nods and holds a hand out for his keys. Tommy hurries to unbuckle his seatbelt and scramble out of the car.
The building is apparently some kind of high-end casino. A gilded sign declaring it the “Rosewater Paradise” sits above elaborate glass doors with gold fittings. They don’t go into these doors, however. Instead, as the valet takes their car towards a parking garage, Tommy’s father leads him around the side of the building to a service entrance. He knocks with confident raps and then waits.
An enormous brick wall of a man answers the door after a few seconds, dressed in a dark suit and a darker scowl. He looks at Tommy and his dad, unimpressed. “You on the list?” he growls.
“Bringing the entertainment,” says Tommy’s father. “Should be there under ‘Prodigal Son.’”
The large man consults a clipboard, then stands aside from the door and gestures inside with a jerk of his head. “Straight ahead through the kitchen.”
Tommy’s father leads him through a small entryway and an industrial kitchen into a plush meeting room of some kind. A green carpet matches the felt surfaces of the various gaming tables around the room, and the rest of the place is all cherry wood and leather lounging couches. Apparently some kind of private gambling den?
In the center of the room is a large roulette table, nearly half as wide as Tommy is tall. It also appears to be missing something; where the pillar in the center would usually be to spin the table, there is a small empty ring and some open screw holes, as though the handle had been removed at some point.
“Strip,” his father orders.
Tommy looks over at him, startled. He’d almost forgotten himself for a moment in his awe of the place. When he continues to hesitate, his father smacks his ass. “Now.”
Tommy hurries to do as he’s told, shucking off his shirt, pants, underwear, and the uncomfortable new shoes until he’s entirely nude, shivering in the open air. His father confiscates the discarded clothing, setting it aside on a chair.
“Now, let’s get you in position,” the man says. He throws a gesture over Tommy’s shoulder. Tommy turns to look behind him to see the huge bouncer coming back towards them. He seems to know what Tommy’s father intends, because he doesn’t hesitate when he reaches the boy’s side. Together, the man and Tommy’s father lift him unceremoniously into the air and dump him face-down onto the roulette table.
Tommy blinks at the unexpected maneuver, squirming uncomfortably. Before he can change his position at all, however, his father has grabbed his wrists while the bouncer grabs his ankles. They slide him into position with his chest over the center of the roulette wheel, his arms and legs hanging off the sides. His arms they pull taught to either side of him, fastened to the table by golden cuffs embedded into the wood that Tommy had assumed were just there for decoration. His legs are spread open to either side and fastened to some kind of railing that circles the roulette table beneath it, halfway down to the floor; Tommy can just barely feel it supporting the bottom of his feet.
When he is firmly locked into place, his father grabs him by the shoulder and gives him a heave. Tommy’s eyes widen as he begins to spin freely, the table and the circular railing turning in tandem to whirl him around. The roulette wheel clicks its rotations with soft but deep thunks. His father smiles.
“Perfect,” he says, sounding pleased. “Although, hang on—”
He disappears back the way they came, into the kitchen, and then returns moments later with a bright red apple. Pinching Tommy’s cheeks on either side to force his jaw open, he shoves the apple as deep into the boy’s mouth as he can get it until Tommy’s teeth sink into it, holding it in place.
“There we go!” his father crows. “Now it’s perfect.” He walks over to the chair where he’d left Tommy’s clothes and picks them up, holding the bundle in his arms.
“Don’t you take that out until someone tells you to,” he instructs his son. “I’ll be back later tonight to pick you up.”
And with no further information, he departs. The bouncer follows after him. Tommy is left naked and alone on the roulette table with an apple stuffed in his mouth, wondering what the hell is about to happen to him.
He doesn’t have to wait long to find out. Soon enough a door on the opposite wall bangs open and a boisterous gaggle of men in suits stumble their way into the room. Many of them look surprised to find Tommy there, and a few of them laugh at the sight of him.
“Well now,” says one of them. He gestures to the apple in Tommy’s mouth. “Isn’t that just the perfect picture of sin?”
Finally, one man in a particularly expensive-looking pinstripe suit follows the group in from back and shuts the door behind them. He has short-cropped hair and a handsome face, tidy and confident, like he just stepped off the cover of a finance magazine. He works his way to the front of the crowd and gestures affably to Tommy.
“Gentlemen!” he addresses the crowd. “Welcome to today’s game. Feel free to wander around and play some blackjack or get drinks if you wish, but if you’re looking to score points tonight, this is how it’s going to work.”
He gives Tommy’s table a demonstrative spin, sending his vision whirling around the room. “Tonight we are playing Roulette Race! To participate, simply stand in an evenly-spaced circle around the table. A spin will determine whose turn it is. When our delightful entertainment here comes to a stop, the man that he is facing and the man directly behind him are chosen. When the dealer says go, you will each begin fucking the orifice closest to you. Whoever comes inside him first gets a point! You may stand in the circle as seldom or as often as you wish, but whoever has the most points by nightfall wins tonight’s pot!” He grins and holds his arms wide. “Any questions?”
The men around the room grin and shake their heads. The man in the pinstripe suit steps back and gestures at another man wearing the casino’s uniform who steps up to Tommy’s side in his place. Presumably the “dealer.”
The man takes hold of the apple in Tommy’s mouth in one hand. “Bite down,” he instructs quietly. Tommy does as he’s told, biting through the apple and freeing it from his mouth to drop into the dealer’s hand. “Now swallow.”
As Tommy chews and swallows the bite of apple, the dealer gestures for the men to take their places. “Step right up, Gentlemen.”
More than half of the men in the group gather in the circle, while others wander off to the bar or one of the other gaming tables. Staff have appeared around the room as though by magic, manning the various stations, but Tommy doesn’t get much of a chance to look at them because a moment later the dealer is saying, “First spin, here we go.” And then Tommy’s world is a swiftly tilting blur.
The wheel stops with him facing a white man in a blue suit. He looks up into a cruel, eager expression that has become very familiar to him over the past few years. The man steps forward, unzipping his fly and pulling out an already-stiff cock. Behind him, Tommy feels one hand come to rest on his hip and another on the opposite buttock.
“On your mark,” comes the dealer’s voice. “Get set... go!”
Tommy is filled immediately painfully deep with the men’s cocks. They’re in a hurry, and they plunge in and out of him like madmen, fucking him hard and fast. Despite his long practice with deep-throating, Tommy gags repeatedly as his mouth is ravaged by a dick plunging in and out at top speed. Behind him, his under-prepared rectum clenches painfully around a similarly rough invader.
Five minutes later the man in his mouth comes down Tommy’s throat. The dealer holds up a hand.
“First point to this gentleman!” he calls. Turning to look at the man behind Tommy, he offers, “You may choose to finish now if you wish, or you may interrupt and stay in the circle in order to have a better chance at coming sooner next time you’re selected.”
The man chooses to interrupt. The cock is yanked harshly out of Tommy’s ass as the man withdraws. The dealer once again takes hold of Tommy’s shoulder. “Next spin!” he announces.
And so the game continues. The spins are almost worse than the fucking, leaving Tommy dizzy and disoriented every time he stops. But the fucking is pretty bad too. Because they’re racing, the men are all incredibly harsh. Most thrust in wild, barely coordinated slaps of their hips, scraping roughly against his insides. One nearly takes his eye out when he accidentally slips out of Tommy’s mouth and jams his cock against the boy’s face.
Others use a different tactic, forcing themselves as deep as possible into Tommy and then thrusting in small, quick spasms. These hurt less, but leave Tommy feeling stuffed to the gills, especially when he gets two men who use this strategy at the same time. They spear him so collectively deep that he feels as though their cocks might touch each other somewhere inside him.
The worst comes about an hour or so in, when he starts to have repeats. Men who have previously fucked his ass plunge their dirty cocks into his mouth, forcing him to taste his own rectum. It’s not as bad as it could be; his father had left him an enema to take last night, so he’s pretty clean all things considered. But the musky bitterness still makes him gag and recoil, causing the man in front of him to grab him by the hair and hold his face still as he forces his cock down Tommy’s throat.
By three hours in, Tommy is sore and exhausted, his stomach reeling from the amount of cum he’s swallowed. By five hours he’s not sure how he hasn’t passed out yet. And the game is still not over. Tommy is filthy, dripping with lube and cum and his own sweat. Everything smells like alcohol and semen. He’s long since lost count of how many cocks have been inside him; he blew well past his old daily record in the first hour. Time blurs together in an endless parade of dicks spreading him open, filling him up, and spilling inside him.
Tommy flashes back to his training, something he hasn’t thought about in a long time. The last time he was fucked this long was the machine that Cecil had strapped him into as punishment. That had been the most horrific nightmare of his life, but this is swift approaching an equal status. At least the machine had been consistent—relentless, but predictable. With these men the approach changes every few minutes; cocks of different sizes and levels of firmness and fucking style switch between each other constantly, so he never knows what to expect. One moment he’ll be choking on the fattest cock he’s ever had in his mouth, and the next a long thin one will be pushing down his throat and pulling out again so fast it takes his breath away.
Occasionally he’ll get stopped in a position where he has a brief glimpse of the leaderboard before another cock eclipses his view—it’s an enormous chalkboard on one wall of the room with last names written on it and a series of tally marks. The tallies are his only measure of time. How many are there now? Fifty? Seventy? As the afternoon draws on he’s sure there must be close to a hundred.
Despite the infinite horror that stretches out the time around him like a colorful blur, Tommy’s torture does eventually come to an end. A man is named a winner. The crowd cheers. Tommy barely hears it behind a white noise hum in his ears, lying dazed and sore and exhausted on the roulette table.
One message does penetrate the fog, however, as the man in the pinstripe suit pipes up. “Oh, before you leave! I have been instructed to inform you that our entertainment here tonight is available to rent for private sessions, for those who are interested. Please see myself or the dealer for contact information.”
Tommy whimpers, his throat gravelly and sore from the day’s activities.
The men leave, all except the man in the pinstripe suit. He shakes the dealer’s hand and smiles. “Excellent work today, Carl, as usual,” he says pleasantly. “I know it was a long shift. If you and your staff want to have a little sample of the goods on the house as an extra thank you, you’re welcome to him.”
“Thank you sir,” says the dealer with a polite nod.
The next hour is every single staff member in the room taking turns fucking Tommy’s ass. At least some of them are halfway gentle. They slide in and out of his hole with slow, deliberate strokes, hitting him deep and scraping like fire against his sore and abused passage. Eventually he whimpers so much in pain that they shove another apple in his mouth to shut him up, leaving him looking and feeling like a stuck pig.
Finally, when even the staff are satisfied, Tommy’s father returns. Tommy is too weak to even dress himself, let alone stand on his own, so his father and the bouncer do it for him. The bouncer had come in his ass twice, Tommy recalls. His cock was particularly girthy, if he’s remembering correctly.
In the end the bouncer has to carry him out to the car, bridal style. Tommy’s father makes a show of berating him in front of the random passers-by on the sidewalk as they walk out to the car. “Just because you’re twenty one now, doesn’t mean you have to drink an entire distillery!” he bluffs. “Honestly, next time you drink too much to walk, I’m not coming to get you! Call a cab or something!” The cover story ludicrously reminds Tommy that today was his birthday. He’s seventeen now.
The bouncer slides Tommy into his seat and buckles him in. Tommy’s sore ass screams in pain from sitting down, but at this point it’s only one signal among many from his body’s frayed nerves. The door slams behind him and his father slips into the driver’s seat.
Tommy is unconscious before they reach home.