Caught

Story Info
A trans thief is fucked between two big cis guardsmen.
3.2k words
4.65
10.6k
24
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was just meant to be a basic scout, a recon of the place before they actually robbed it, and Casey still didn't know how the fuck the alarm had gotten triggered, how it had sent the whole place blaring so loud he couldn't think, so many ringing bells. Trev and Mattel must have gotten out, because when he grabbed for the rope he'd dropped in on through the skylight he couldn't see anyone through the glass, and the guards came at him from both ends of the corridor at once.

"No, no, wait, wait — "

"What have we got here?" asked one of the guards, and Casey tried to scramble loose, but he was already hauling Casey by the scruff of his hoodie down the corridor.

"Street rat, looks like."

"What was this, pretty boy, first heist to whet your whistle, see if you could handle it?"

"No," lied Casey. "No, no, I swear — "

It was impossible for him to get free as he was pulled into a room with two benches and a table in it, and thrown to sit on one of the former. He tried immediately to get up and got a sharp slap across the face for his trouble, making him yelp and drop back down.

The two guards were big fuckers, both of them over six feet and both of them strong, fat blokes, the leathers they wore making them look even bigger than they were. One of them had a beard, and the other one just had a moustache, but they had the same kind of haircut, similar dark hair.

"What do you say we do with him, Ludo?" asked the one with the moustache, arching his eyebrows. "Pass him to the city guard?"

"Now?" Ludo whistled under his breath, putting his hands on his hips. "Night shift on a Tuesday, I don't know if they'd even process his arrest. They'd have him stripped down before the doors had even closed on the wagon, and by the time the dawn comes, every fella on nights will have fucked him twice. Do you really want to subject the lad to that, Kell?"

"It'd be dripping out of every hole," mused Kell, stroking his beard. "He'd probably be fat with it — that, or half-turned inside out."

"Please — "

"Shut up, lad, we're not talking to you," Kell snapped at him, and Casey closed his mouth. "'Course, if we pass him over to the day shift, that means we gotta hold onto him 'til dawn. Make sure he doesn't make any trouble for us, keep him quiet."

"Keep him occupied."

"And with all that work we've got left to do."

"Shame there's no way we can just let him go," mused Ludo. "After all, he's a would-be thief. He has to be punished, doesn't he?"

"Oh, he's got to be punished," agreed Kell. "How else does a lad learn?"

There was a roiling fear tossing over and over in Casey's belly, his stomach churning with it, and he felt dizzy and nervous, couldn't breathe, couldn't stop trembling in his place. His lips were quivering, he knew.

"You could punish me," he blurts out, leaning forward, his hands gripping at the front of his trousers. "You could just — You could... do it. And let me go. And I wouldn't come back."

"Huh," said Kell, tilting his head to the side, glancing sidelong at the other guard. "You think we could take a stab at it, Lu?"

"Mm, but I don't know," replied Ludo, looking Casey up and down. "Is he gonna submit to our authority, what with us not being members of the city guard? Will he take what we have to teach him to heart?"

"I will," promised Casey breathlessly. "I will, I will, I swear, I promise."

"You believe him, Kell?"

"I don't know, Ludo. Do you?"

"I say we give him a chance."

"Please, please just — "

"Yeah, yeah, street rat, we hear you," said Kell. "Strip those clothes off."

He knew how this went. He wasn't stupid, he knew that it was this or the night watch, and he'd heard enough to know that they weren't just kidding about getting passed around — anyone young, halfway pretty, and vaguely clean, got passed around like a toy.

He started to strip.

He bent over to shove down his trousers, faced the other way so he didn't have to look at their faces, but both of them let out low noises of admiration as the curve of his ass and the lips of his cunt, and as soon as he was out of his pants, one of them had him by the hair and kept him bent over, not letting him stand up straight.

"Oh, look at that, Ludo!"

"We made the right call with this one, Kell. Passing a bonafide cuntboy off to the night guard is like tossing a prime steak to the fucking dogs."

"Ah, ah," moaned Casey as Kell nudged his legs apart with one of his knees, putting two fingers either side of his pussy and spreading it wider, baring him to the air and making him squirm. The touch was blunt but not rough or hard, and when he pressed down and squeezed either side of him, it sent a throbbing heat up his spine. It was the knowledge he was about to get fucked, wasn't the same as arousal, wasn't because he actually wanted this, but Ludo was laughing.

"You see that little fucking dick jump? Something tells me you'd be better off in a whorehouse than robbing treasuries, street rat."

"I don't know, Ludo, he's a pretty responsive little dick, but little is the word. You sure he's gonna be able to take us?" Kell squeezed him again, fingers massaging into the fatty flesh in between his thighs and the swell of his cunt, and it was sending blood rushing downward. "You a virgin, street rat?"

"No," whined Casey, and he didn't mean to, did not fucking mean to, but his thighs spread a little further apart, and that made Kell laugh from his fucking belly.

"Oh, no, he is not," agreed Ludo, and now his hand was on Casey too, coming up from underneath with two fingers nudging and pulling at his dick, and Casey's legs went weak for a second. "Look at him, all wet and glistening. How's his asshole look?"

"Seems a lot like his cunt, like the eye of a needle. He wet?"

"Beginning to be, but I don't know..."

Casey stared between his own legs as Ludo came into view, dropping to his knees. He felt a little dizzy, made to bend over like this with nothing underneath him and his head tipped forward, and he didn't register exactly what was happening until Ludo's tongue swept over him and he cried out.

"Mmm, street rat he may be, but he tastes good," Ludo said, and Casey tried to move up and out of the way, but Ludo was shoving his thighs further apart so that he could mouth and suckle at his cock and his lips, and Kell was standing in front of him so Casey grabbed at his thighs to keep from tipping forward. His face was pressed into the leather-clad swell of Kell's gut, and Kell laughed at him, reaching underneath him and pinching one of his nipples between his thumb and forefinger, tugging on it. He jumped, whining, but he couldn't get away from the wet heat of Ludo's face buried in his cunt, lapping at him so sloppy and so messy it was making his entire body throb, his cock jumping and his cunt clenching as his big fucking nose nudged at the opening of his cunt, his lips closed around his cock and sucking on it so hard that Casey couldn't function with it.

"Can't, can't, please," whined Casey, and Kell laughed, leaned over him as he was to pull and squeeze at his nipples like he was trying to fucking milk him, and then he let them go.

"Hey, excuse me," Kell told Ludo. "Coming through."

"Huh...? Aaah," Casey moaned as Kell leaned over his back and sank two fat, thick fingers into his cunt, moving so slowly that it was driving him crazy, his knuckles dragging and pulling at the muscle of his entrance, at the inner part of his walls. "Aah, ah, please — "

"Please, please, he says, he never even wanted to fucking steal anything, I bet," said Ludo, blowing hot air over Casey's cunt with his mouth open and making him squirm. "Just wanted to get fucked, huh? I bet he wanted to get passed to night watch all along — maybe we should hand him over once we've tried him out."

"No, no, you said — you said — "

"We said we'd punish you, street rat," said Ludo, taking his dick between two of his fingers and squeezing it between them, making Casey cry out and try to lurch in his place, but all that happened was his back hit Kell's chest. "It's not a punishment if you like it."

"I don't," moaned Casey, and then moaned louder as Kell pulled his fingers, now wet, out of his cunt and forced them into his ass instead, making him choke and shudder in his place. His cheeks were burning hot, and there was sweat on his skin, way more than there'd been just from lowering into the building. "I don't like it, I swear, I promise — Ah ah ah — "

"I don't like it, I promise," imitated Kell, scissoring the fingers in Casey's ass and forcing the muscle to stretch with a slight burn as Ludo shoved his tongue back in his cunt, swiping around the inside of his walls. "Sounds like you like it to me."

He couldn't argue, couldn't make his mouth put words together, could only focus on grabbing at Kell's thighs to keep standing as Kell spat on his hole and rubbed the spit around the ring of his ass with his already wet fingers; Ludo's tongue was buried in him and he was still squeezing and tugging on Casey's dick, making him fucking throb with it even though the squeezing was a little too hard and the pleasure from it edged on painful, electric and overwhelming.

"I'll need my dick wet to get in here," mused Kell, and he leaned back, unbuckling his belt.

"Wait, wait, I can't — aah, I can't, stay upri — Mmhf — " Kell's cock was big in his mouth, forcing past his lips, already hard and thick, and he moaned around it, which just made Kell laugh and moan himself.

He let Casey go easy for a second, let him just try to wet the cock in his mouth and accustom to it, but then he said, "Enough training, street rat, time to embrace the job," and sank his cock all the way into Casey's mouth. Casey tried to scream around him but the sound couldn't go anywhere when it was muffled by his dick, and he gagged, but Kell didn't let up, keeping him shoved down to the root with the tight grip he had on Casey's hair. His face was mashed up under Kell's belly and his nose was full of the smell of him, the smell of sweat and cock and leather, and when he whined again because Ludo was spitting on Kell's fingers for him and lubricating the way for Kell to better hook his fingers in his asshole, Kell moaned again.

"God, his throat's like a fucking pussy," he groaned, rolling his hips into Casey's face and making him choke again even as he was trying to relax his gag reflex and breathe through his nose. "Street rat's a cuntboy from both fucking ends."

"He's juicy as anything too, dripping like a fucking sluice," said Ludo, and mouthed at his open hole, sucking at an edge of one of his lips and making him scream at the sudden overwhelming sensation, and then he was coming and both of them were laughing, the cock throbbing in his throat and Ludo's tongue vibrating against his cock, teeth grazing him in a way that was sending Casey fucking crazy.

He was clenching on air, his dick throbbing and jerking under Ludo's mouth, and he'd squirted a little, could feel the wetness soaking down his thighs, dripping out of him.

"Mm, I don't know, maybe I've made him too loose," said Ludo, and shoved three fingers into his cunt at once, making Casey howl through the gag buried in him, and Kell groaned. "Yeah, this cunt is just too sloppy now, Kell, it wouldn't be fair for you to get him from that end and me to get this one."

"You know what to do, bro," said Kell, strain in his voice, his body quaking a little. "Tighten him up again, just keep him making those noises."

Ludo's fingers slipped out of him, and then his palm came down with a sudden wet crack, and the hot burn of pain throbbing through his pussy had Casey sobbing, his eyes going from watering slightly at trying not to gag to full on tearing up. He was moaning, sobbing, couldn't stop himself as Ludo spanked his pussy twice more, making him feel so swollen and sensitive he thought it'd fucking kill him, and then Ludo shoved the whole of his cock into him in one go, and Casey lost the ability to think.

He couldn't breathe, couldn't string two thoughts together as he was held upright by the tight grip of Ludo's strong fingers around his waist and Ludo's cock buried in his cunt, still hot and tingling from the slaps, and Kell's cock filling his throat up. He was scrabbling at Kell's thighs to keep himself up, whimpering and letting out filthy wet noises as Ludo slammed his hips into him and Kell rocked in his place — he was covered in spit, his chin a mess of saliva and fucking precome, and his cock was throbbing, cunt clenching.

He was on a cloud, somewhere high in the sky between the lack of oxygen and the pummelling to his cunt, and when Kell suddenly pulled free and left his mouth empty he coughed in surprise, feeling filthy and suddenly open.

"Wait, wait," he whined when Ludo pulled out too, leaving his pussy suddenly so empty it almost felt sore, made him feel incomplete, unfinished, and Ludo laughed at him he pulled him up by the shoulders, turning him around.

"Wait for what, street rat? A second ago you didn't want us to start, now you don't want us to stop?"

He didn't get to reply — Ludo was lifting under his thighs as he fell back against one of the cushioned benches, and he slid his cock back into Casey's cunt, bringing Casey to drop down on top of him so that it was suddenly buried in him to the hilt, his own cock rubbing over the hairy underside of Ludo's belly.

Kell was already behind him, and Casey braced himself on Ludo as best he could as Kell shoved his spit-slick cock into Casey's ass, shoving him open. He was breathing heavily, his head rushing with all the sudden air he could get, and feeling Kell and Ludo's cocks rub together with just a thin fucking wall keeping them apart was going to drive him crazy, was going to split his head open.

"You like it up the ass, street rat?" growled Kell in his ear, then grazed his teeth over the back of Casey's neck and made him gasp sharply, arching his back — Kell shoved him forward, making him fall against Ludo's belly as he slammed his hips hard into him, and Ludo laughed, sliding his hands through Casey's hair and pulling his face against his chest — his jerkin was open and the cloth of his shirt was surprisingly soft.

"Move him a little," said Ludo. "Up an inch or two."

"Huh?" asked Casey, trying to look behind him to see what Kell was doing, but Kell moved too quickly for him — he shoved him forward by his hips and lifted him slightly up, and suddenly with every fuck-forward of Kell's hips Casey's cock was dragging against Ludo's belly, and he started whining without being able to stop.

"Yeah, that's it," said Ludo, and when he laughed the jump and movement of his belly was incredible, but nothing compared to the way his cock shifted and jerked inside him, a completely different movement to the pull-back and sudden sheath of Kell's as he thrust into him. "That's it, that's a lad. Gonna come again, huh? This what gets you off, this what you like?"

"Fuck, fuck," Casey whimpered, trying to think of anything but the way that tension was gathering in him again, the way that his cock was fucking throbbing with the tightness, each rub of Ludo's hairy belly dragging over the sensitive skin in just the right fucking way, perfect and painful all at once.

Kell smacked the side of his ass, and it was a fucking crescendo: this time as he came it wrenched through him so hard that he felt like he was going to split in two, his head spinning, his vision going almost dark at the edges, and he was sobbing raggedly without being able to stop —

Kell just kept going.

They both did.

* * *

The world was a haze, and Casey was only vaguely aware of the fact that the sun was dawning outside because the light of it was shining on his face through the window, and it felt warm, felt nice, in contrast to the painful emptiness as Ludo pulled out of his cunt again.

"No," Casey moaned, and Ludo laughed at him, sliding a thick plug into his cunt the same as the one Kell had already put into his ass when he went to do a round. He'd lost track of how many times he'd come tonight, and he didn't want it to stop, didn't think he could stand for it to stop. Ludo was dressing him, his trousers, his hoodie, his shoes, and then Ludo's hand was loosely cupping his cunt through the fabric, rubbing at him.

It hurt, fucking ached, but Casey just leaned into it, shuddering out a breath, and Ludo laughed at him.

"Ready to go?"

"More," said Casey, putting his hands on Ludo's chest.

"Let's go," said Kell, and Casey looked blearily past him to the other guy in the doorway, some little prick in robes.

"Who's this?" he asked, his gaze falling on Casey. "You had a break-in last night?"

"Nah, boss," said Ludo, and Casey whined as he was hauled up onto Ludo's shoulders, the plugs shifting in him even before Ludo smacked him on the ass and nudged them further into him. He spread his legs slightly, trying to stick his ass out more. "You guys play checkers on your breaks, we play with something like this."

"How revolting," said the boss impassively, and then Ludo was moving with him over his shoulder, his body throbbing with the movements, the plugs shifting in him.

"So, street rat, we dropping you off somewhere, or shall we take you home and go another round?" asked Kell.

Casey opened his mouth, feeling his sore jaw, couldn't make it go.

"Another round it is," said Ludo, squeezing his ass, and Casey shuddered and blearily nodded his head.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymous11 months ago

Great story!

AnonymousAnonymousabout 1 year ago

I keep imagining what would happen if they had given him to the nightwatch after.

Share this Story

Similar Stories

Stuck A trans man is gangbanged by his college bros.in Transgender & Crossdressers
Bred in the Dark Ftm college freshman gets bred on a late night train.in Transgender & Crossdressers
The Concert She's violated at an outdoor concert.in NonConsent/Reluctance
Forced onto a Stranger's Lap A dark subway provides opportunity to take advantage.in NonConsent/Reluctance
The Fitting Room Trans man gets fucked by his tailor.in Transgender & Crossdressers
More Stories