Tommy celebrates his 16th birthday at the rectory—although “celebrates” is probably not the word to use. It’s been long enough at this point that he has no illusion that he might receive any kind of gift or acknowledgement, or even a reprieve from his usual duties. It’s more that there is a calendar on the wall, and Tommy has gotten in the habit of carefully and deliberately marking off the days as they pass, to avoid losing all sense of time altogether. His victories these days are small, and knowing the current date is one of them.
So he notices when spring rolls around once again—May—and puts a tiny little star in the corner of one of the boxes on his calendar. He’s been here just under eight months now. He’s turning sixteen. Technically, he thinks, he’s no longer sexually underage in this state, at least legally. He wonders if that makes a difference for anyone. Were some of his regulars only here because of the thrill of doing something illegal? Or are there new people who will come now specifically because they can justify it to themselves? It probably won’t matter to his experience either way.
His birthday falls on a Wednesday. Wednesdays are a little hit-or-miss. His regulars tend to always come on the same day of the week, based on their schedules, and it’s usually a weekend day—every third Friday of the month, or first Saturday, or last Sunday. Regulars who come every week for any length of time are rare, with Father Lawrence being the notable exception. Tommy wonders how much his father charges for his services. Probably anyone who actually has the kind of money to spend fucking someone every week goes to Jack’s. It seems like a way classier establishment.
Weekdays, Wednesdays in particular, have been known to go by sometimes with no one bothering him at all. It’s hard to know ahead of time. When he first started in the rectory, there were even weeks at a time where no one outside of Father Lawrence visited him. By now, however, his father has gotten the word out enough that those days are long gone. Now he’s lucky if two days in a row happen to line up where he’s not servicing someone or other. He has some vague hope that maybe he’ll be lucky and one of those days will line up with today.
But luck, as always, is not his strong suit. Shortly after lunchtime he hears the jangle of a key turning in the lock of the rectory’s front door. He hurries to the bed and lies down in a provocative position, ready and waiting.
When the door opens Tommy is surprised to find he recognizes the man who enters—but not from his father’s clientele. Men, in fact; after the first man comes into the room, a second one slips in behind him.
He knows them. Their faces are indelibly branded into his psyche: the men who spent eighteen hundred dollars to “deflower” him. Jasper is the tall white one with the frosted tips and... what was the other man’s name? Something with an M.
“Well well well, there he is indeed,” says Jasper fondly. “It’s nice to see you again little Pet. You’re a tough boy to track down, did you know that?”
The other man, the one with the darker skin and the goatee, smiles like a shark. They’re both wearing expensive clothing, although it’s not the fancy suits they had on the last time Tommy had encountered them. “Suppose we should have known that we don’t get the privilege of your real name,” says the dark-skinned man. “The man here calls you Tommy.” His British accent is high-class, like a bond villain, just like in Tommy’s haunted memories. “Do you remember us?” He gestures between them. “Jasper and Malik.”
Malik. That was right. Tommy nods demurely. “You were my first,” he murmurs. He decides to go with shy. They were looking for inexperience last time; they probably want something similar now.
Jasper claps his hands fondly. “You do remember. How sweet! I must admit, little Pet, after our last encounter we just couldn’t get you out of our heads. We had half a mind to come back and buy you for ourselves, but by the time we decided to do so it seems someone else had already snapped you up! Not that I blame him. We’re lucky to have been able to find you again, and that your new owner is willing to share.”
As they’ve been talking, the two men have walked towards the bed, and now they sit down on either side of Tommy. He’s not as nervous about it now as he was when he first serviced them. It’s not unheard of for his father to rent him out to two or even three men at a time. The touch that assaults him now—one set of hands on the back of his neck while another feels up the front of his torso under his shirt—is uncomfortably familiar by this point.
It’s Jasper behind him, running hands down his neck and shoulders and then leaning in to press a light kiss to the joint between. Meanwhile Malik leans in and presses his face to Tommy’s abs, licking a stripe up from his navel towards his pecs, lifting his shirt as he goes. His facial hair tickles Tommy’s skin lightly.
“How long has it been since we last got to enjoy you, hmm?” Jasper murmurs against his jawline, just under his ear. “Too long, certainly. We’ll have to do this more regularly.” He reaches down, sliding his hands under the waistband of Tommy’s pants to cup one of his buttocks in each palm and gently squeeze. “Did you miss us?”
“Of course,” Tommy lies. He presses himself back wantonly against Jasper. “You were my first, and you filled me up so good. I dream about your cocks all the time.”
“Well well, isn’t that cute,” Malik says. He pulls off Tommy’s shirt and encourages him up onto his knees so that Jasper can begin to pull down his pants.
As his rear end is exposed, he hears a soft sound of surprise from Jasper. A hand skates along the soft skin of his ass and comes to rest on the flared end of the dildo embedded inside him.
It’s become a habit of Tommy’s to wear the thing on days when he’s not sure whether he’ll have clients. It’s fairly modest in size, but it’s the easiest way to make sure his ass stays wet and relaxed for any sudden encounters; after one too many harsh entrances by men who don’t care to wait while he lubes himself up, he decided it was the lesser of two evils. Occasionally a customer will be a little disappointed by the way it breaks the illusion of his untouched innocence, but most of the men are charmed or amused to find it there.
Jasper seems to fall into the latter camp. He grabs the base and starts to rhythmically pulse it forward, waking up the muscles and nerves of Tommy’s rectum that had become dulled to the sensation. “What have we here?” he murmurs. “Looks like you have been lonely after all. Well, we’re happy to remedy that.”
He pulls Tommy into his lap, allowing Malik to finish sliding off the boy’s pants, underwear, and socks. He allows Tommy’s ass to slightly hang off the side of his thighs in order to give himself the space to grab the base of the dildo and slowly, slooooowly drag it out of him.
Tommy moans and wriggles in his lap, biting his lip. He can feel that Jasper is already hard under him. Maybe he’ll get lucky and they’ll be quick?
When the dildo is about halfway out of his ass, Malik puts a hand on Jasper’s wrist to halt him. “Just a moment now,” he says. He takes hold of Tommy and rolls him over, off of Jasper, until he’s on his knees and elbows on the bed, ass in the air with the dildo planted halfway into his hole like a flag of conquest.
“I want to see just how much you missed us,” Malik instructs. “Show us how you play with yourself when there’s no one here. How do you get yourself ready for your customers?”
Tommy knows what the man’s asking, and dutifully reaches behind himself to put a hand on the base of the toy, while the other reaches between his legs to grab his soft cock and wake it up. By now he’s become fairly skilled at getting hard on cue; it doesn’t take long.
“Ohh,” he moans performatively. “I can’t help myself. I do it just like this, imagining your cocks.” He thrusts the dildo in and out of himself. He could use more lube, but the thing still slides back and forth with relative ease. “Mmm. I think about you fucking me, the way you were both so big when you were inside me. How you took turns with my mouth and ass. You showed me how good it felt to have something inside me like this, and I just couldn’t go back after that. I’m not satisfied now without something filling me up, keeping my insides nice and warm.”
The two men disrobe casually as they watch him fuck himself with the dildo, taking their time and folding up their clothes neatly and casually. When they come back to the bed they don’t touch him at first, just continue to enjoy the show as he debases himself for their entertainment.
Finally, when he’s started to get hard enough that he’s wondering if they’ll wait for him to come before they touch him again, he feels Malik’s hand on his wrists, stilling the motion of the dildo and his wanking at the same time.
At Malik’s gesture, Jasper lies down comfortably on the bed, head on the pillows. Malik slides Tommy’s body down until his head is over Jasper’s crotch and then pushes him downward, his meaning clear. Tommy obediently opens his mouth and lowers it onto the man’s erect phallus, welcoming it into the wet cavern. He alternates between tonguing the head and sucking on it, only occasionally pressing himself forward far enough to envelop the shaft, swallowing it down once before backing off again to resume his attentions to the head.
Malik’s hands on Tommy’s wrists pull them up behind him, twisting his arms behind his back and keeping them pinned there. With his other hand he picks up where Tommy left off, fucking his ass with the dildo.
“What a good boy,” he praises. “A pleasure to see how you’ve blossomed in our absence. A proper little courtesan now, aren’t you?”
Tommy can’t respond verbally with his lips wrapped around Jasper’s cock, so instead he gives a hum of agreement, wiggling his ass teasingly at Malik.
He hears the sound of a pump bottle; Malik must have taken the lotion from the bedside table. There’s no mistaking the slick sounds of a phallus being lubed up in preparation.
Suddenly, without warning, the dildo is yanked roughly out of his asshole, discarded to one side. Tommy cries out in surprise, expecting to feel Malik’s own cock replacing it a moment later.
Instead, Malik pulls Tommy backwards, off of Jasper’s cock entirely, and manhandles him into position straddling Jasper’s hips. He takes the lead, positioning him, spreading Tommy’s cheeks open with lubed fingers, and guiding him up over the waiting spear of Jasper’s wet, erect member.
Then Malik pushes him down. Tommy groans theatrically as Jasper’s cock begins to penetrate him, sliding up inside him with little resistance. “Oh yes,” he moans. “Yes please, just like that. I’ve missed having your cocks inside me so bad.”
“Well then,” Malik murmurs. Tommy can hear the grin in his voice. “You will love what we have in store for you.”
So saying he pushes Tommy forward, forcefully arching his back and bending him into place, and then maneuvers into position behind him, also straddling Jasper’s legs.
Tommy feels the slick head of Malik’s cock demanding entrance to his backside, butting up against the already-impaled ring of muscle. He forces himself to breathe deep, to relax, as the second dick forces its way inside him, stretching him further, wider, opening him up.
When he’s fully seated inside, Malik pulls Tommy backwards until his back is flush with Malik’s torso. His voice is hot and wet against Tommy’s ear. “Is this how you remember it?” He thrusts his hips. “Is this what you were looking for?”
“Oh god,” Tommy whimpers, swallowing. “Yes, yes! Just how I wanted it! I missed this so much!”
It is not, thankfully, just like he remembers it. When they first did this, Tommy was inexperienced. It hurt badly; he remembers it hurting. He remembers feeling split in half, feeling ruined and fucked-open afterwards. But he’s had time to adjust now. Time to learn. Sure, the men who visit him in pairs or more don’t always stick two cocks in him at once, but enough of his visitors want to fuck him alongside his training dildo that the feeling of double penetration is no stranger to him anymore. It’s not exactly pleasant, but it does hammer home for him just how much experience he’s gained since he was first forced to prostitute himself.
It’s not the only thing being hammered home. Now that they’re fully seated, Malik begins to thrust inside him, pulling him down repeatedly onto the twin phalluses spearing him. Tommy rides out the sensation, letting them do as they wish, and settles in to endure the fucking.
It takes a while. He’d forgotten how much stamina these two have. They fuck him together for ages. Tommy’s view is mostly of Jasper’s face—a lazy pleased smile that twitches as his lover’s cock scrapes up against his own over and over inside Tommy’s ass. His hands flit between holding onto Tommy’s hips as they move up and down, clutching at the bedsheet on either side of him, and reaching up to occasionally play with the boy’s nipples. He seems content to let Malik set the pace, lying back and enjoying the experience.
When they finally come inside him, balls twitching against his ass, Tommy is hideously relieved. He hasn’t looked at the clock, but it feels like they must have been going an hour. He’s winded and sweating, his hole distended and starting to get a little sore. He gulps in air as they slip out of him and allow him to fall to one side on the bed.
But of course, that isn’t the end of it.
Tommy’s eyes go wide as Malik hands him the previously discarded dildo.
“We’ll need some time to get ourselves worked up again,” the man instructs. “Why not give us a show? Let’s see you work yourself with this until you come. No touching yourself.”
“No touching your cock,” Jasper amends. “Do please touch yourself elsewhere for us. I want to watch you pinch those cute little nipples of yours.”
Tommy’s hopes mentally fall. Of course. He’d forgotten how they’d proceeded last time. They’d made him do something like this back then too, hadn’t they?
Resigned, he reaches for the lube and refreshes the coating on his sex toy. Then he lies back on the bed, points his asshole towards the two men, and gets to work.
The toy slides into him easily once it’s slicked up; his hole is loose and tired from the previous fucking and accepts it without protest. Holding it by the base, he proceeds to rock it in and out of himself in shallow thrusts, just how he likes it, driving the head of the dildo into his prostate. Waves of tired pleasure shoot through his hips, low but intense like bass music vibrating his body. With his other hand he reaches up to his chest and dutifully begins to pinch his own nipples, trying to make it look like he’s squeezing them harder than he actually is.
This, too, is something that he’s had some practice with by now. Many of the men who visit him want to at least pretend at some kind of mutual pleasure, so he’s become well acquainted with his own prostate. He’s hard again quickly, his cock a curved bow against his stomach as the pleasure works through him.
“Oh yeah,” he says for the men’s benefit. “Oh, right there, yeah. It feels so good! It feels so good to have something in my ass! Work me! Work my hole!”
He feels the men’s eyes on him as he pleasures himself; something else he’s gotten used to. No other gaze will ever feel as shameful as his father’s, and that has become a regular fixture at these debasements. Tommy ignores them with ease and focuses on getting himself off.
It doesn’t take him long. Certainly not as long as it took for the men to fuck him. Before he knows it he’s coming, splattering himself with hot jizz, clamping his fingers down on one of his nipples as his orgasm rocks through him and his passage clenches tight on the dildo. When he comes down from the high, he finds he’s breathing hard once again. He feels his rectum give a few last lingering spasms around the toy still nestled inside him.
“Adorable!” Jasper says with a small clap. “You are just as cute as I remember. Cuter, if anything. Alright Pet, time for round two.”
They switch sides. This time Malik is in front of him, sitting up. Jasper pulls Tommy up from where he’s still collapsed like jelly on the bedspread and pushes him into Malik’s arms, straddling the man’s lap. As he’s pushed chest-to-chest with Malik, Tommy struggles weakly. “Wait a second,” he protests. “I need to—” he starts to reach behind himself, towards the dildo still fully embedded in his ass.
But Jasper grabs his wrist and directs his arms around Malik’s neck. “Oh, no need for that,” he says cheerfully. “Surely an experienced little hole like yours can handle a little more.” So saying, he maneuvers Tommy’s body into position and begins to coax the head of Malik’s cock through the tight ring of muscle, working it up into him alongside the toy.
“Th-three?” Tommy stutters, guessing what they’re planning.
Malik smirks. “Don’t tell me you’ve never had three cocks in you at once?” he teases. “Do we have the pleasure of taking another of your virginities?”
“How lovely,” Jasper coos. Now that Malik’s cock is halfway in, he presses himself against Tommy’s back and begins to force his own dick into the over-stuffed orifice. Tommy whimpers. It’s not the first time, but it’s also not something he’s done often enough that it isn’t still a little bit painful. His muscles burn as the third phallus spreads his full ass even wider, obscenely open.
The only other time he’s taken a penetration this big was with one of his father’s friends. The man had brought an actual suitcase full of sex toys, and had delighted in stuffing as many as he possibly could inside Tommy at once. He’d managed to fit four smaller toys into him at the same time at one point, the same kind of stretch Tommy feels now. In the end, the man had taken all the toys out and finished off by penetrating him with both his fist and penis at the same time, crowing about how he’d, “always wanted to try jacking himself off inside a boy’s ass.”
That was one of the sessions where Tommy’s father had been watching.
The men surround Tommy like a sandwich, sweaty skin pressed against him in front and behind. Their cocks move in him in unison beside the toy, sliding in and out as they fuck him slow and deep. Tommy moans, trying to ignore the twinges of pain from his abused hole.
“So good,” he grits out through his teeth. “I’ve never been this full before. It’s amazing. I’ve never felt like this. I didn’t know anything could fill me up this much.”
Malik growls against his neck and gives a particularly harsh thrust. Jasper chuckles. “So glad we can be of service,” he whispers into Tommy’s ear.
Their hips rock up into him over and over, a methodical pounding fullness. Malik reaches around behind Tommy’s head and grabs him by the hair, yanking his head to one side so he can lean in beside it and kiss Jasper over Tommy’s shoulder. They proceed to make out, sloppy and wet and hungry, as their lower halves continue the relentless fucking.
Tommy hopes his father hasn’t scheduled anyone else today. For one thing, these two are going at it way longer than people usually do when fucking him. The minutes drag on and on, probably approaching another hour. For another thing, Tommy’s not sure his hole will be able to handle anything else after this. Anyone who comes in for these men’s sloppy seconds could probably just shove their whole arm up his ass and he wouldn’t even notice with how fucked-open he feels.
They pound him and pound him and pound him some more. Malik pulls his hair. Jasper reaches around to pinch his nipples, wrenching and squeezing them until he squeals and tightens around their cocks, making them laugh. It just keeps going, on and on.
Malik eventually comes first. Tommy feels the twitch of his cock and then his hips still and stutter as he unloads the contents of his balls into Tommy’s ass. Tommy could nearly cry with relief.
Once Malik catches his breath, when his cock has gone soft enough to slip out, Jasper takes over. He grabs Tommy as Malik slides out from beneath him and forces the boy down onto the bed, upper torso pressed against the sheets while his hips remain hoisted into the air. He proceeds to slam into Tommy’s hole at a desperate clip, completely different than the slow, methodical fucking they’d given him together, jack-hammering away like a crazed animal. He comes as well a few minutes later; Tommy feels the man push on the base of the dildo at the same time, forcing it as deep into him as it can get as he comes next to it.
Finally, Jasper pulls out as well, leaving just the toy behind. If he weren’t lying on his stomach, Tommy wonders if the thing would just slip right out of him; he feels so loose and numb—he couldn’t clench his muscles if he tried.
“Ahh,” Jasper says in satisfaction. “That’s the stuff. I knew it would be worth seeking you out again.”
Malik smiles and pets his lover’s hair, smoothing the strands back into place. “So you did,” he croons. “A true genius, let it never be denied. And now that we know his whereabouts, we can come and do this more often.”
“Mmm,” Jasper hums happily. They dress themselves without much care for Tommy’s exhausted, discarded form on the bed, and show themselves out. He hears the click of the key in the lock sealing him back inside after they depart.
Tommy is left in an exhausted puddle on the bed, mind swimming in a fucked-over daze. It’s his birthday, he remembers hazily. He wonders how many more such anniversaries lie in store for him.