Jailbird Fling Pt. 01

1: Light Reading with Jack

Life in a minimum-security prison camp isn't terrible. We can roam freely, for the most part, have plenty of options for recreation, get three decent meals a day, and have access to phones and TV. Sure, I have to live with five other guys in a dormitory smaller than the living room in my old apartment, but it's not so bad when two of those guys suddenly decide they want to spitroast me one quiet Saturday afternoon.

Eddie and Ralph are both art thieves and consider themselves rivals. They're always talking about their alleged successes and hypothetical plans for when they get out. Eddie looks like he'd more fit in at a construction site than an art museum, all bulk and hair. Ralph more fits the part, thin and lanky, though he looks like he's never seen the sun.

Neither of them are gay or bi, so they say, but here we are. They said they were bored and horny, so Eddie took my front hole and Ralph took the back.

I slurp and suck on Eddie's modest cock, able to comfortably fit his entire length in my mouth without straining my throat too much. He has his hands in my hair and his head drops back as he groans in pleasure. I pop his cock out of my mouth to press my tongue to the underside of the shaft, massaging his frenulum with long, slow licks. Precum starts to bead on the tip so I flick my tongue over his slit before taking him back into my mouth.

Behind me, Ralph pushes his cock deep into my ass. He was only slightly bigger than Eddie, so even with just his rough, sloppy fingering to prep me, my hole accommodated him mostly painlessly. I squeeze around him as he pulls out and throw my hips back into him as he thrusts forward. His fingers dig into my hips as he speeds up, a throaty growl letting me know he's enjoying himself.

"Fuck.... Nick's pussy is tight," Ralph groaned.

"He knows how to use his mouth, too," Eddie moaned.

I'm right here... I grumble to myself. All I can do aloud is hum around Eddie's cock as he starts to rock his hips into me.

The burly man holds my head still as he fucks my mouth. I relax my jaw, tongue out, and let him do all the work. Drool mixed with precum drips down my chin as his balls slap into it. His tip pounds against the soft palate at the back of my mouth, making my cock twitch.

Ralph picks up his pace as well, slamming into me in short, hard thrusts. A couple times he hits my prostate and I clench around him. He doesn't pick up on the hints and I can't arch my back enough to get him to hit that spot more often.

I can't hold back my moans any more. Stimulation from the front and back drives me crazy. Eddie and Ralph are close, their cocks pulsing inside me. Bracing myself against Eddie's thigh with one hand, I stroke my aching erection with the other. Our dorm is filled with the sounds of pounding flesh and loud moans. Anyone outside could hear us. I hope someone with a long, thick cock would want to fuck me next.

Ralph is the first to pull out. "Shit, I'm cumming!" He shoots his hot load onto my back, then rubs his cock between my cheeks to squeeze out the last few drops.

Eddie follows close behind, pulling his cock out of my mouth just in time to cover my face in his cum. He lets out a low, almost bestial, growl as three thick streams hit my hair, my cheek, and my still open mouth.

Used and covered in semen, I sink to my knees, legs trembling as I cum into my hand. I lick my lips and smile up at the two men tucking their now limp cocks away. "If you're ever bored again...."

"If I can't sneak out to see my girl soon, I might have to take you up on that," Eddie complains.

Ralph is kind enough to toss me a towel as he returns to his bunk. "My wife's in New York, helping me scout out some potential business."

Eddie's eyebrow shoots up and I know they're going to sit and talk about heists for the next few hours. I wipe my face and wrap the towel around my waist to head to the showers.

***

After a shower and dinner, I head to the library. It's a cramped room, like most others in the prison, with a dozen or so bookshelves filling the center of the room and a line of desks along one wall. At the entrance sits the librarian's counter and the ancient card catalogue the prison still uses. The librarian, Dorothy, has been the librarian since the camp was built fifty years ago. When she's in a good mood, she can answer any question you may have about the prison, the town, or just about anything. Unfortunately, she is rarely in a good mood.

"Evening, Miss Dorothy." I greet her with a smile as always.

"Get your books and get out. I'm locking the doors in fifteen minutes whether you're still in here or not." She didn't even look up from her crossword puzzle as she snapped at me.

"Yes, ma'am...." Not in a good mood tonight.

I had hoped to ask her about the new guard rotation. I saw a couple new faces and hadn't heard about anyone quitting. A couple fights broke out last week, one over a game of cards and the other in the middle of a pottery class. Neither were that serious, yet the entire camp was locked down for a few days. We'd been spoiled having only five guards for the entire prison. It's going to be harder for me to get dicked down if guards are crawling around everywhere.

I poke around the stacks for a while until I hear the jingle of keys. It had been five minutes at most. Expecting to see Dorothy glaring at me over her trifocals, I was surprised to see a guard chatting with her instead.

A new guard at that.

He is young, only a few years older than me at most, and fills out his uniform perfectly. His thick biceps are folded across a broad chest, his pecs straining the buttons on his shirt. The basic beige pants hugged his muscular legs and stretch to their limit to cover the bakery he carries behind him. When he leans down, one hand pressed to the counter, the muscles in his forearm, exposed by his rolled-up sleeves, flex, and the curve of his back flows flawlessly into the curve of his ass.

Captivated by that ass, I don't even notice when he turns his head to face me.

"Mr. Silvers?" Dorothy now glared at me over her trifocals.

I jump and snap my eyes up to the guard's face and, God, if it isn't as perfect as the rest of his body. The slightest shadow of stubble covers his sharp jaw and his smile ends in a pair of dimples. His forest green eyes light up with that same smile. Even his basic guard haircut, high taper fade and fluffy brown waves held immaculate by some light mousse, have me swooning.

"Silvers? You're in one of the dorms I'm in charge of." The hottest cop I'd ever met turns fully to face me, leaning his hip against the counter. "Jack O'Conell. Let's get along, yeah?"

"Yeah, let's...." My eyes drift down again when he looks over at Dorothy. I swear I can see the imprint of his cock in his pants.

I don't know what he said to Dorothy, but the old woman gets up and shuffles out the door, Jack holding it open for her. I go to follow, excited to squeeze past that perfect body, but Jack puts his hand out to stop me.

"You don't need to leave. I'll lock up for Dorothy, don't worry. You were still browsing, right?"

Fuck, and he's nice, too? "No, I'm good. I can come back tomorrow." I need to get to my bunk and rub one off.

"Library's closed tomorrow. It's Sunday." Jack lets the door close and leans against the counter again. "Go on. I don't mind waiting a few minutes."

I just nod and retreat to the furthest bookshelves. The space between the last two shelves is the narrowest and blocked from the cameras. As soon as I'm out of sight, I shove my hand into my pants to attend to my growing erection. After a few strokes, I'm completely hard. If I close my eyes, I can imagine that imprint out and free, a massive cock perfect for rearranging my insides. Biting the hem my shirt to muffle my moans, I pump my hand, milking drop after drop of precum.

My eyes flutter open and I still see Jack, sexy and flawless, in front of me.

... I see him in front of me?

My hand freezes and my shirt drops from my mouth. "This isn't...." I didn't know how to continue. It was exactly what it looks like.

"You this into world history?" Jack asks, coming towards me.

I glance at the shelf next to me. Sure enough, it's a book on the World Wars. "It's important to understand the past, right...?" I pull my hand from my pants, still sticky with precum. Jack's eyes burn into me and I feel my cheeks burn in turn.

"... Don't stop." His voice is quiet. I'm not sure I heard him correctly.

I just look up at him--up because, now that he is right in front of me, I can see he has at least three or four inches on me, well over six foot. Not a single word travels through my brain or out of my mouth as I stand dead still with my jaw dropped like an idiot.

"Don't stop," he repeats. His finger hooks onto the waistband of my pants and tugs them down until my hard cock pops out.

It's hard to breathe as I watch his finger linger under my erection. As he pulls his hand away, his finger grazes my balls, definitely not by accident. A tantalizing smirk spreads over his lips at the soft gasp that escapes my mouth.

Without taking my eyes off him, I brush my fingers over the tip of my cock, gathering the puddle of precum that has accumulated since I gained an audience.

"You're not going to offer to help?" I lick my lips and start long, slow strokes.

"I think I've helped quite a bit already," he says, his voice low and directly fueling the throbbing in my cock. "Am I wrong?"

"Not at all...." I slip my hand under my shirt to play with my nipples, moaning softly as I pick up my pace. "I got this hard just looking at you."

"You always this easy to please or are you just horny?"

"You're just fucking hot."

Jack's eyes are locked onto my cock. Having his undivided attention, watching the rise and fall of his chest quicken as he's aroused, it's damn near euphoric. His desire is palpable, a force in the air between us that sends shivers through my whole body. The imprint in his pants is even thicker than it was before. I drop back against the bookshelf, my knees weak from the thought of that cock inside me.

I pinch my nipple under my shirt and pump my cock faster. My breaths are coming out in slutty moans. My eyelids droop as I watch Jack biting his lip and rubbing his cock through his pants. The officer lifts my shirt up, each of his five fingers brushing my other nipple, and pushes the fabric into my mouth, stifling my moans. I nearly bust from just that touch.

Jack moves his hand to his zipper. It feels like he's moving in slow motion. He unbuttons and unzips his pants with one hand and grabs my wrist with his other, keeping me from stroking myself. His cock slowly emerges from his pants and is as incredible as I imagined. At least eight inches, thick and veiny, with a smooth pink head. A beautiful monster. My mouth starts watering and my asshole puckers, both wanting--needing a taste. Jack places my hand around his cock.

"Which hole do you want, baby?" I can't take my eyes off that cock, so my question is directed to him. It throbs in my hand, which I translate as, I don't care. I'm just going to destroy you. That's what I want it to say, at least.

"Neither. For tonight." Jack, still holding my wrist, moves my hand over his cock.

"Such a tease...." I start pumping him on my own, squeezing the base and twisting my hand up to the tip. Ignoring my nipples for now, I move my other hand to stroke myself.

"Not yet." Jack grabs my wrist again before I can touch my aching cock.

"Afraid I'll stop once I cum? Don't worry, I'll take all night to get to know this monster if you let me." I wiggle my restrained wrist, half-heartedly trying to break free, while not breaking the rhythm of my strokes around his erection.

"No, I just want to watch your cock leak and twitch without you able to do a thing about it for a little while."

A wicked smile spread across that pretty face. I struggle against his hand a little more, only to get it pinned to the shelf above my head. This makes my cock leak and twitch more.

He's barely a foot away from me. His quickening breaths caress my face. I match the tempo of my strokes with his breathing, faster and faster, his quiet panting soon turning to deep moans. I let out a whimper, his voice driving me crazy. My cock aches for release, so sensitive that the precum dripping from my tip sends jolts through my stomach.

Jack clearly enjoys my suffering. His cock pulses and twitches in my hand as he watches my hips squirm. If I try to free my hand, he presses it harder against the shelf. At this point, even the pain of the metal shelf digging into my wrist bone makes my mind swirl.

When he's close to cumming he takes another step, closing the gap between us. The tip of his cock touches mine, our beads of precum fusing together. It's agonizing. He's so close, teasing me, torturing me.

"Fuck, Jack.... Touch me, please. I'm going to lose my mind." I'm usually not one to beg, but the low groans that rumble from his throat and the hunger in his eyes make me weak. It doesn't help that his lustful gaze only gets stronger as I beg.

"Since you asked so nicely, I'll help you after all, Silvers." He wraps his free hand around both our cocks, and I do the same. His grip pinning my hand above my head tightens as he rocks his hips to rub his erection against mine.

"Mn, you got this hard just looking at me, so I think we're even," I sigh, rolling my hips against him.

My breaths are short and quick already, almost every exhale a moan. Jack presses his lips to mine to drink in those moans and all I can breathe in is him. His tongue greedily explores my mouth until I push my tongue through into his. Even when our lips part, our tongues still cling to each other. I suck him back into my mouth, but he escapes, biting my bottom lip.

"Fuck, Silvers, I'm cumming!" He takes half a step back, angling his cock towards me to avoid dirtying his uniform.

The rough strokes he does to finish himself off press my whole body against the bookshelf behind me. All we're doing is frotting. He isn't even fucking me and he's pinning me to bookshelves. The mere flash of a thought about what he could do to me with that cock is enough to send me over the edge.

"Me, too! Ahh, Jack!"

We burst at the same time, shooting both thick streams of cum onto my stomach.

Jack releases my hand and lets me slide to the floor. He squeezes a few more drops of semen onto me and tucks his cock away.

"Clean yourself up. It's time to close the library."