The Jailbird's Flight

By Heitor Oliveira

Published on May 9, 2024

Gay

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Duncan gave a discreet, taunting middle finger to his asshole of a cellmate as soon as the burly policeman let him out and locked the door behind him again. What he really wanted was to tell him to fuck off but it really wasn't worth it when he was so close to get out of jail. Whistling his merry song, Duncan was guided outside and could finally feel the sun shining on his face without the worry of some thug messing with him, he had enough of that already. When they got to the entrance, Duncan was unsurprised to discover his dad was not there to fetch him, but that did earn him a pity stare from the officer. He didn't like it, but it was hidden behind the man's shades so it was easier to handle.

"I can drive you to your place, kid," he offered, a big hand squeezing his shoulder in an attempt to comfort. Duncan shrugged and acquiesced with a nod. It was not like he had money for a cab anyway.

"Thanks, officer." Duncan let a mischievous smile creep up his pierced lips to defuse any emotion of the moment. He didn't want any of that. The bulge the uniform pants could barely hide, though? That's something he's actually interested in.

That officer was one of the few guys in the precinct that was yet to lay their hands on Duncan during the four years he was there. He must have been aware of his fame, as news of his willingness to suck dick and take up the ass flew around fast like the building sheltered just gossiping old ladies, but he never made a move on him and Duncan was as impressed as he was disappointed. That was one of the hotter guys there. It wasn't like there was a ring on his finger from what he could tell, so he could just assume the guy was straight as a rod. However, as that was probably the last time he would see him, it wouldn't hurt to be a little bolder. A rejection was probably the worst it could happen.

Riding shotgun in a patrol car was a new experience for Duncan. For all his years as a jailbird hailing from his early adolescence, never before he had such tranquil travel. As they drove to the address of his old apartment, Duncan sneaked his hand to the officer's thigh, caressing slowly in a practised gesture. The movement got him an arched brow and a tired sigh, but no denial. Good enough. Duncan unfastened his seatbelt and lowered himself towards the officer's crotch as soon as they stopped at a red traffic light.

"Don't go too hard, punk," the officer grumbled as his zipper was pulled down and his dick was fished out of his underwear. Although it was only semi-erect, it was already quite heavy on Duncan's hands. "Don't wanna get us killed here."

"I trust in your driving skills, mister officer," cooed Duncan in a fake high pitched voice. He even batted his pretty blue eyes innocently for emphasis, but it should look quite ridiculous as he held the black dick near his head. It was bigger than his whole face. He snorted as he imagined how the view was for his partner and gobbled down the treat in front of him.

That was the biggest cock Duncan had in a while, and he had a lot of cock in the precinct. As experienced as Duncan was, he couldn't take it all in one go, a hefty part of it having to be held in his hands for a slow wank. Slobbering all over it, Duncan took his time savouring the big piece of meat in his mouth, tongue swirling around it like it was a lollipop. One so wide it made his jaw ache, but delicious and rush inducing all the same. He gagged a bit when he tried to get some more into his mouth, soldiering through the burn at the back of his throat. That was when he felt one the officer's big, calloused hands caressing his messy, crunchy-from-too-much-dying hair absentmindedly. The motion was oddly comforting, and Duncan found himself surprised to not be completely against it. He looked up, trying to see if he could get a better feel of the situation through the other man's expressions, but he could only see him looking to the road ahead like nothing important was happening, only one hand on the steering wheel.

As he took more of it, Duncan moved his hands to fondle with the officer's balls. That earned him a tug in his hair to pull him even further down the cock, which made him moan on it, his vocal chords serving as a makeshift vibrator. Duncan realised the car had long come to a stop, but he was far from done. The slightly harsher treatment sent a bolt of pleasure straight to his own cock, now straining in his pants. He adjusted himself in the passenger seat, in a fashion he could grind against it in search for his own relief. He worked his way on the shaft inside his mouth, his eyes inadvertently rolling back as he felt the veins pulsing on his pierced tongue. Duncan could feel the man was about to come as he heard the stream of Patois roughly mumbled and his hair was pulled harder. Duncan grabbed the muscled thighs still covered as sperm surged into his mouth. The man must have been quite frustrated, if the sheer amount going down Duncan's throat was any sign. The former inmate dutifully swallowed it all and lapped his tongue around the glans to clean it from any traces of cum. Duncan humped the seat under him a little more and it wasn't long until his orgasm arrived, making him jizz his own pants.

"They weren't wrong about you," the officer said, as Duncan collected himself and noticed they were parked in front of his apartment. "You're good at sucking dick."

Duncan actually cackled at that, his lips curling in mirth at his actual fame in the precinct. "Your fat bulge didn't lie either, man. Thanks for the ride."

He was about to open the door and leave when a strong hand kept him in place. The officer still wore his shades, but Duncan noticed from the way his brows furrowed he was about to talk seriously. The man produced a business card out of somewhere he couldn't see and carefully placed it in Duncan's hands. It depicted what appeared to be a guy with nerdy brown hair and a gap toothed smile. Those were his only discernible features, though, as a painfully familiar big black cock was covering his eyes and nose. Beside the guy, the name "That's Gonna Leave a Gap!" was written in bold lettering and a crude picture of a gaping asshole was added to make sure any semblance of subtlety was disregarded. Unless you counted the very small contact number on the corner Duncan almost missed.

"Is that you?" Duncan pointed at the penis used to obscure the model's face. He eyed the flaccid form of it still hanging from the open pants and cocked an eyebrow. His only answer was a mischievous smile. "It is a pornstar level cock. Might as well use it as such."

"I wasn't intending to, but Chris insisted," the officer relented, a somewhat fond sigh escaping his lips. "He's the director there and a friend of mine. I can refer you to him if you'd like. He's always looking for new talents."

Duncan thought long and hard about it and came to the realisation that maybe he would need some help getting back on his feet. He might as well take it. Not many people would give an opportunity to an ex-convict in the first place. With a crooked smile, Duncan said yes. He liked being fucked, doing so in front of a camera wouldn't be that hard, right?

Right?

He discovered the following week it was nowhere as easy as seeing the finished product made it look like. He had a meeting with Chris a few days before and the guy was the most insufferable man he had met in his life. Fucker came from money, though, and could offer a high enough sum to make Duncan tolerate his spoiled, annoying ass. So there he was, sitting on a comfy couch in the fancy house Chris used for shooting. There were camera guys ready on the sides, but the one camera Duncan kept his eyes locked on was the one held by Chris. His face should show his actual displeasure of having to deal with the man, but Duncan guessed it fit with his whole punk aesthetic. The makeup artist even gave him a flashier black eyeliner than the one he came with, so they apparently were leaning on that.

"Hey guys! We're back with another episode of your favourite show: That's Gonna Leave a Gap!" Chris announced, his voice already grating on Duncan's ears, but the man didn't seem to be bothered in the slightest by his bitch face. "Today's star is this beautiful jailbird, Duncan! Wanna say something to the fans, man?"

"Yo." Duncan kept it curt, since Chris did mention he could be a little bitch in the interview because of his looks and style could make up for it, but he was mostly doing so to end that part as soon as possible.

"Isn't he a sweetheart?" Chris snickered, as Duncan relaxed on the sofa, manspreading casually as the other kept on babbling. The punk kept on answering the questions absentmindedly, wondering when he would get his promised gap. "I heard it's hard to get a job after leaving jail. Is it just for the money you're doing this?"

"It's for the money," Duncan answers bluntly. "But I also like taking cock so it's not all bad."

Duncan gave the camera his bad boy smile and Chris laughed. "Yeah, I think we talked enough. I hope you like big vergas latinas. Bring los chicos!"

The Spanish accent was atrocious, but Duncan was curious to see what he was working with. He tried to not break character and not look too excited when two tall beautiful men walked into his direction, wearing only somewhat loose sweatpants. They looked like Greek sculptures with how chiselled their faces and muscles were, but knowing the name of the website he was filming for and judging by the tent in their trousers, they did differ in at least one department. Both guys had a good tan to their skin and the same striking green eyes, but while one of them had his dark hair at shoulder length, the other kept it a bit shorter and slicked back.

"How do you like them, Duncan?" Chris giggled as he saw the punk's awestruck gaze towards the two hunks before him. "This one is Alejandro and this one is his brother, José!" Chris pointed to the long haired one and then to the other one. "You may call them los hermanos gran verga!"

Duncan could see both brothers also cringe at the awful Spanish, but decided to focus on how beautiful their bodies looked up close instead. He let one of his hands feel up the abs of Alejandro, the one closer to him, impressed at the definition, before doing the same to José. His slightly chipped black nails scratched their stomachs in envy, as he never had the commitment to keep going to the gym.

"They're hot," Duncan replied, nonchalantly, getting down the sofa to assume his position on his knees. "When do I get to blow them?"

The two brothers couldn't contain the snicker, but Chris let out a full blown cackle. "Anytime, man. Go wild."

Having the director's allowance, Duncan didn't wait a single minute to pull down the two pants just enough to have their cocks bounce off, already as big as Duncan's face and not even fully hard. The punk was actually dumbstruck as he tried to wrap his hands around them and failed. His face must have looked quite funny because Chris was still cackling behind his handheld camera and both Alejandro and José had mirthful smiles.

"Still think you can handle them?" Chris snickered as he zoomed into Duncan's shocked eyes. "Try to hold them next to your face. Slap them on it."

Duncan did as told, confirming that both of them were bigger. Granted, his face was somewhat small, but it was still impressive. It also made him all the more aroused, wondering how it would be to have those monsters ravaging his mouth and ass. As he slapped his own face with the two big dicks, Duncan felt his own cock harden inside his shorts. It didn't take long before he took one of the hardening dicks inside his mouth without even being prompted, wanking the other one to the best of his ability. He gagged on it immediately, but that didn't keep him from sucking it.

"He told me earlier he honed his skills in the precinct," Chris confided from the information he got in his little interview before. "Were the guys there good teachers?"

"He's very well trained." Duncan looked up to see that the smooth, cool voice was Alejandro's. Also to make sure that was the cock he was sucking, as he was so horny he didn't bother to check before. "You could see it from how fast he dropped to his knees like a good boy."

"But don't hog him all for you, bro." The rougher, confident voice was accompanied with a pull in his hair, taking him out of Alejandro's cock and into José's, making it very clear who it was. Duncan didn't bother with the change and just adjusted himself to José's face fucking, opening his mouth to the fullest as the dick went in and out of his throat. "He does have a great mouth."

Duncan went to masturbate Alejandro's dick while his mouth was fucked, his hand flowing easily as it was already slicked with saliva. He felt two hands holding up his face and, looking up, he could see José's confident face as he bucked his hips forward, hitting the back of his throat every time. Duncan felt his face flush as his throat was fucked, but his cock twitched in his pants at every thrust. When José let him go, Duncan was all dizzy, only waking up when Alejandro's dick was slapped on his face, demanding attention. Before he took his dick in his mouth again, however, Duncan slipped his shirt off due to the heat, earning a whistle from José.

"Nice piercings," he noticed, kneeling beside the punk to mess with his exposed nipple piercings. Duncan moaned with the caress, which made José continue to tease him further. "They look pretty on you. Do you have any more?"

Since Alejandro pushed his face all the way down his dick like his head was a fuck toy, Duncan had to use his own hands to pull down his shorts and underwear, exposing his pierced cock and frenulum. José let out an amused laugh when he saw Duncan was already erect.

"Do you like sucking big dicks that much?" José pinched Duncan's nipple again, eliciting a moan out of the punk, who nodded immediately as his pierced tongue worked Alejandro's shaft.

"He clearly does!" Chris intervened, palming his own hard-on in his khakis. "But! That's as good a time as any to leave a gap in our pretty boy's hole!"

As he was forcibly pulled out of Alejandro's dick, Duncan took a few seconds to adjust himself and when he noticed, the two brothers were naked and ready, the enormous dicks they were blessed with being as intimidating as it was arousing. He noticed someone from production gave Alejandro a bottle of lube and that José sat on the floor before him, signalling for Duncan to come closer. The punk went on all fours towards the other man and kissed the tip of his erect dick before gobbling it down again while Alejandro lubed his own dick behind him. It didn't take long for the other brother to arrive, pushing lube into him and stretching him with his fingers. Duncan moaned into José's cock as his prostate was stimulated.

"Slap his ass!" Duncan heard Chris' annoying voice suggest and soon enough a firm hit was brought upon his asscheeks. The punk couldn't suppress the needy whine that escaped his lips. As much as he disliked the backseat driving, at least the suggestions were good.

"I should have expected you to have a tramp stamp," mused Alejandro, tracing the swirly tattoo on his lower back with his thumb. His dick was rubbing slightly against Duncan's asshole and he could get in at any given moment. His smooth voice had a provoking tone to it, but Duncan couldn't care less. The punk shaked his butt, trying to get more contact with the man's dick and Alejandro snickered. "It suits you."

Alejandro pushed slowly into Duncan and he felt like his ass was getting torn apart. While he did take some big dicks before, none of them were like the two actors before him that had both the length and the girth. His breath went shallow as each inch got its way inside his hole, and it didn't help that José was still fucking his mouth lazily. Duncan relaxed his muscles the best he could and used José's thighs to support his own weight. Before he knew it, Duncan took Alejandro up to the balls and the man was slowly pounding his ass, making the punk gasp and moan with each thrust. As the two brothers spitroasted him, Duncan felt pleasure like never before. At some point, Alejandro hoisted one of his legs up and turned him on his back, fucking him harder and hitting his prostate like a madman, while José managed to fuck him even deeper into his throat, to the point he could press the bulge of his own dick through Duncan's neck. It was sudden when the punk felt his body convulse and spurt cum all over his chest, as his prostate was abused at one side and he was choked at the other. He felt bad as he knew he should have warned the cameramen about it, but it was not like his mouth was available at the moment either.

"Damn, look at him. Came untouched all over himself," narrated Chris, getting closer to film the sperm on his chest. "I wonder how his ass is looking up now. Mind to show us, Al?"

Alejandro didn't seem too pleased, but acquiesced all the same, taking Duncan on his arms as if he were a ragdoll, adjusting him so Chris could film Duncan's gaping hole as he took his dick out. The punk felt it empty without the man's dick in it, but tried to wiggle his ass for the camera all the same.

"Bring him here, bro," José called and Duncan could see he was already sitting on the sofa, legs spread just enough to bring attention to the appendage standing tall between them.

"Put his back to the camera," instructed Chris, excited. Alejandro carefully put Duncan in the desired position, the punk's ass hovering over José's dick. "Yeah, show his tramp stamp. Just keep looking at us, Duncan."

Duncan was getting lost in José's green eyes before the man slapped his ass to make him look back at the camera as instructed. The big hands in his waist lowered him slowly on the shaft and, without any dick in his mouth to conceal his moans, the punk had to let them roam loud through the room. He didn't even need any encouragement to bounce on José's dick, whining and sighing every time it brushed on his prostate. Seeing that Duncan was keen to do it all by himself, José just gave him one more slap on his ass before putting his hands behind his neck, enjoying the sight of the punk fucking himself on his dick.

"He takes it like a champ! Look at him bouncing," Chris narrated, and Duncan couldn't help but glower at him, cheeks flushed but still riding José. His patience with the man was thinning but it really shouldn't as he was the one who would pay him later. Lucky for him, Alejandro intervened, positioning himself behind the punk, lubing his dick as he caressed his shoulder. Chris eagerly took the bait. "Oh, two big latino cocks at the same time? Savage!"

Duncan slowed down on José's dick to let Alejandro slowly, but surely penetrate him alongside his brother. The punk's mind was blown and he could barely register the two cocks inside him, his prostate being punctured with each blow, his hole getting stretched to lengths Duncan didn't know were possible. His body fell limply on José's chest, his brain being only able to send messages for his vocal chords to moan in pleasure. He also felt Alejandro's body close to his back and his hand pulling his hair and whispering dirty things in Spanish to his ear, but the mind numbing pleasure reached its peak when he felt both brothers' cum filling his hole.

They held him in that comfortable hug position for some time, which Duncan was actually somewhat grateful for, as it gave him time to recompose. So, when Alejandro eventually took him into his arms and held him with his spread legs to face the camera, Duncan was somewhat presentable. Or as presentable as one could be with smudged eyeliner and a debauched from being thoroughly fucked look in his face. He gave the camera his most confident smile as cum oozed from his abused hole. He tried to pucker it and failed, the motion only making more sperm flow.

"Well, that's a gap!" Chris whistled as his bred ass leaked, because of course he would. Duncan let his head drop back and rest against Alejandro's shoulder. He had no more patience for that shit. "Anything you want to say to the fans, Duncan?"

Duncan simply chuckled, raised his head and gave Chris the middle finger.

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