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Jailbird Fling Pt. 02

Part 2- Hard at Work

It's been nearly a week since Jack O'Conell teased me with his massive cock only for us to jerk each other off in the library.

And he hasn't mentioned it since.

As a matter of fact, when he formally introduced himself to everyone the next day, he acted as if he didn't know me.

That monster he keeps hidden in his pants has kept me up at night, yearning for it, wanting just a little taste of it. I feel like nothing else will satisfy me.

So desperate and so horny, I jumped on any opportunity. Dave, from the dorm next door, called me over, already rock hard and raring to go, pinned me against the wall--right onto the tits of some porn star poster--and shoved his little dick into me. It isn't even long enough to reach my prostate. Now, he's just poorly pounding my ass.

Fuck, Jack's dick could send my prostate on a tour of my insides.

"You look like just like a bitch from behind," Dave grunts, interrupting my daydreams.

I know he doesn't want a response. He made it clear he only wanted a hole to fuck. If I make a sound, he puts his hand over my mouth, if I push back into him to try and get something out of this, he presses me harder against Miss Porn Star's tits.

Sure, it's a bit demeaning being used like a sex toy, but sometimes I just really need some dick. Sometimes it's worth it.Jailbird Fling Pt. 02 фото

Just not this time.

Now I'm stuck waiting for him to finish.

Luckily, the ordeal is done in less than ten minutes. Dave digs his fingers into my hips as he cums into his condom. Once he releases me, he snaps, "You better not've cum on my poster!"

"Oh, don't worry. I didn't." I don't think even an ounce of blood rushed down to my cock.

He scoffs at me and I take that as my cue to leave.

On my way to the gym to sweat my frustrations away, I spot Jack. He is doing nothing but walking down the hall towards me and my cock twitches in my pants. As we get close enough, I put on my best smile and give him a wave.

"Where are you headed?" he asks. It's a question required for his job, but I swear I heard a little flirty lilt to the question.

"To the gym. I could probably use a spotter," I wink as I do my best to keep my eyes up.

Jack raises an eyebrow. Not in a "come hither" way, but more of a "what the fuck are you talking about" way. All hope of continuing where we left off, dashed in a single moment.

"I'm sure there's someone that can help you there." With that, he continued on his way.

I got a hell of a workout in trying to burn off the disappointment of a shitty day.

***

Jack's businesslike unfamiliarity continued through the rest of the week. Aside from a nod here and a "hello" there, he pays no attention to me outside his job. He's the same with everyone. No one can get a read on him.

It was the beginning of the month, which always meant a rush in the commissary since spending limits get reset. My job is dealing with commissary inventory, and it's absolutely terrible for the first week of every month.

There are two other guys that work the stockroom with me, but they refuse to do the "bitch work" in the office and only gather items for prisoner orders or stock shelves. As a result, for nearly half the day most weekdays, I'm stuck in a cramped, dusty office that was somehow twenty degrees colder than the rest of the prison. I input all the items we're low on and submit requests for new inventory into an outdated program on a computer nearly as old as the prison.

Our only supervision is Theo, a clerk employed by the prison, and he doesn't care if we're crushed to death beneath a shelf as long as someone gets the orders he needs on time. On the bright side, when I'm in that office, I'm left alone. Theo only checks on me when his superiors are walking the halls.

But, worst of all, none of them have any interest in fucking me.

Unsurprisingly, the influx of orders means we run out of popular items. I'm stuck in the ice cold, cramped, lonely office for the entire day, fighting the ancient computer to get as many resupply requests in as possible. By quitting time, my hands are cramped and my head throbs behind my eyes. I'm not finished, but I don't care. I trudge past Theo as I check out.

"Are all the requests in?" he asks just before I could leave. The other two guys are nowhere to be seen.

"No, I'll get the rest tomorrow."

"There only a couple dozen items to order! How did you not get them all done? What were you doing in there?"

"It takes nearly thirty minutes to place one order and the program doesn't allow for different items in one order." I keep my tone polite, regardless of how badly I want to snap at him.

"You're going to finish those and these new ones tomorrow, Silvers."

I don't respond. I'm in the last eight months of my three-year sentence. Stupid arguments will only extend my stay. Theo is petty enough to write me up for "talking back." Chanting this over and over to myself gets me through Theo's pointless rant about my lack of work ethic.

Jack passes by me as I drag myself back to my bunk. I don't have the energy to play flirt when it's not going to get me anywhere, so I just keep walking, sparing only a polite nod. His footsteps stop after I pass him, but he doesn't say anything. If my head wasn't pounding, maybe I'd have the capacity to be delusional enough to think he cares.

***

By lunch the next day, I start to think I don't mind if I get a few more months added to my sentence. For the first time since I started this job, Theo checked on my progress hourly, expecting me to meet impossible quotas. Just before he was due to come for another pointless audit, I hear him talking with someone.

"You'd be doing me a huge favor. I'm sick of him." He's right outside the door to the office, so the "him" can only refer to me. "Just make sure he's not slacking."

"Great. Now I have a babysitter," I mumble under my breath. The mouse creaks in my hand as I try to use it as a stress ball. Footsteps enter the office and I don't bother to fix my pissed face before turning.

It's Jack.

Jack, with the imprint of his massive cock right in my face, is my babysitter.

"... Officer, I don't really need supervision," I complain, gauging his reaction.

With his flawless smile, he closes the door behind him. The door is never closed.

"You didn't seem to mind my supervision last time." His voice was low, not quite a whisper, but nowhere near loud enough to travel through the heavy door.

"We both had better things to look at last time." I lick my lips, starving for a taste of that cock.

"If you get these orders done early, you might get something nice to look at again."

Harsh reality shattered my fantasy. "I already tried to explain to Theo that I can't go any faster. It takes this computer twenty minutes just to load a page."

"Are you good with computers?"

"If you're just here to call me incompetent, too.... A nice cock can only get you so far."

Jack leaned down over my shoulder, placing his hand over mine on the mouse. "That isn't what I meant. Just don't want to suggest things you've already tried."

While he clicked away at the computer's settings, his other hand explored my chest and abdomen, his fingers brushing against my hard nipples every chance they got.

"I haven't tried anything. Before getting stuck in here, I did just about everything on my phone. Hardly ever used a computer."

It's hard to keep my voice steady when all I want is for his hands to explore the rest of my body too.

"There, it should run better now." With his hand now free from controlling the mouse, he runs his fingers up my arm. "Try submitting an order."

The clicks needed to complete an order request is muscle memory at this point. It turns out I can even do it with a guy tracing my neck, my jaw, and my lips with his extremely distracting fingers. I open my mouth without his needing to ask. His fingers press against my tongue and inside my cheeks as I eagerly suck on them, my dick perking up at the thought of having his cock in my mouth next.

The computer is moving a bit faster. Everything went though in half the time and I was able to focus only on the fingers reaching for the back of my throat.

"You still have more items to request, don't you? Get to work, Silvers." As Jack spoke, he started pumping his fingers in and out of my mouth, my tongue barely able to keep up with them.

I shift uncomfortably in the hard seat as my cock strains against my pants. Jack slips his other hand under my shirt, pinching and tugging on my nipples if I slow down, which only makes me move slower. I moan around his fingers and squirm in my seat. While I wait for this second order to finish processing, I rub myself through my pants.

"Stand up, Silvers."

Jack doesn't take his fingers out of my mouth as I stand. He kicks my chair aside and moves his other hand from my nipples to my back, pushing me to lean on the desk. That hand traces my spine down to my ass and roughly slaps and squeezes one cheek.

I spread my legs and coat his fingers in as much saliva as I can manage. I'm rock hard as I anticipate Jack filling my ass with his fat monster.

"Get through those orders before the end of your shift and I might have a treat for you." He yanks my pants down and the freezing office air nearly shocks the horniness out of me.

As soon as he pulls his fingers from my mouth, I moan, "God, fuck me, Jack."

His fingers, slick with spit, circle my hole, teasing me. "Time's ticking."

I don't think I've ever typed so quickly in my life. Once I complete the product information page, he slips a finger in. He curls and twists his finger for each field I fill in. When I hit that final submit button, his finger curls right into my prostate.

He doesn't need to prompt me any further. I move right into the next order as he slips another finger into my ass. He scissors and spreads my hole open while I finish another order. Another order, another finger. His hand pumps those fingers deep as I bite my lip to keep myself quiet. I would probably kill anyone who interrupted us right now.

By the time I'm on the next order, he is fully finger fucking me. I need to lean heavily on my elbows to stay standing--and to have leverage to roll my hips back into his fingers. It takes me a while to get through the first page where I need to type everything in. Usually, I hate the two dozen dropdown menus I need to scroll through after, but that was before I learned how hard it is to type with someone fingering my ass.

Jack pulls his fingers out while the order processes. I glance over my shoulder, hoping to see his cock again. Instead, I see him rubbing his hand over the baton on his hip.

"After all that stretching, I was hoping for your cock."

"You haven't earned your treat yet. This will have to tide you over."

He pulls the baton from its holster and rubs the lubed-up handle along my crack. It's skinny, barely the size of two fingers. I can't help but feel a bit disappointed.

With an overdramatic pout, I turn back to the computer and get back to work. As punishment, he slaps my ass, hard, leaving an angry red mark. I let out a surprised cry and quickly slap my hand over my mouth, whipping my head back to the door.

"Aren't you worried about someone coming in?" I whisper. Prisoners can fuck as many other prisoners as they want, but it is definitely illegal for guards to be fucking prisoners.

Jack only locks the door in response.

Just like with his fingers, each step of the process earns me more of the baton handle. When it's pushed all the way in, I can feel the ridges and bumps on the grip. It doesn't come close to filling me, but it's better than Dave's prick or nothing at all.

Jack pumps the handle slowly, only occasionally grinding against my prostate, until I complete a couple more orders. Then he gets quicker with each step I complete, thrusting hard and deep by the time I finish the next order.

I'm down to the last few orders. Jack is working that baton like a piston, hitting my prostate with more and more thrusts the more steps I complete. My legs are shaking by the last order and my cock is dripping precum. I was wrong about the baton--no I underestimated Jack. He had that thing angled perfectly. More than once, I had to stop and bury my face in the crook of my elbow to muffle my moans. The red "submit" button was nothing but a blur for that last order. I missed it about ten times before I finally clicked the right spot.

"Mnn, done, ah, Jack, fuck, God, fuck me, please," I beg, fully slumped over the desk as the baton gets me so close to cumming, but can't finish the job. "I need your cock, please."

"Not today, Silvers." Jack reaches around and starts pumping my cock at the same time. "Not in your ass at least."

I rock my hips between the baton and Jack's hand, the double stimulation enough to send me over the edge. "Ah, fuck, Jack, s-so stingy--ah! Shit, I'm, ha, I'm cumming!" Clamping my hand over my mouth to muffle my loud moans, my cock releases its pressure, shooting a thick stream of cum onto the floor under the desk.

Jack pulls the baton from my ass and I sink to my knees. I peek at the time on the computer once my senses return to me to see I still have an hour left of my shift. Still a bit dazed, I try to get to my feet. Jack puts a hand on my shoulder and shoves me back to my knees.

"It's time for your treat, Silvers."

Suddenly, I'm looking into the eye of that beautiful monster. Jack slaps his cock against my cheek as I smirk up at him, licking my lips.

"I'm glad I ate a light lunch. Left plenty of room for a huge treat like this."

I press my lips to the side of his shaft and lick each side, base to tip, before focusing on the swollen pink head. Jack has his hand in my hair as I flick and swirl my tongue around the tip of his cock. I take just the tip into my mouth, pumping the base and sucking out the drops of precum, before popping it out of my mouth to drag my tongue up and down his frenulum.

"Fuck, Silvers... you're good."

Jack's moans and the sweet, salty musk of his cock on my tongue are making my cock twitch back to life. I stroke the shaft as I suck his balls into my mouth. Jack tugs my hair to position my mouth back at the tip of his cock.

"What? You don't like the full treatment?" I tease, fondling his sack with my hand.

"I want to see those pretty lips on my cock."

I oblige without hesitation. First, I bob my head around the tip, savoring the taste on my tongue. Then, in one slow dip, I take every inch of this monster. I feel each and every vein throbbing along the shaft and shiver as his tip slides past my soft palate. With my nose nestled in his pubes, I pause to swallow a couple times around him. The groans and fingers running through my hair encourage me to do a couple more long, slow strokes like that--pulling my head back to the tip, then fully deepthroating him to the base.

I change pace to quick, short bobs while pumping the base to give my throat a break. Jack has other plans. Hands tight in my hair, he pushes my head deeper and deeper with each pass until he's deep in my throat again.

With a tug on my hair, he pulls my head back. A thick web of saliva mixed with precum connects my mouth to him and drips down my chin.

"Open your mouth. I'm going to fuck your face."

My mouth is open and waiting before he even finishes his sentence. He holds my head steady with the hand tangled in my hair and starts to slowly thrust into my mouth. Once he's sure his cock is lined up, he pushes deeper and moves faster. In no time, he's pounding his dick into my mouth. I can't help but gag and choke as that monster destroys my throat.

Jack groans above me, his grip on my hair tightening. I start stroking myself, my cock hard and oozing again. As his rhythm breaks, I take charge again, swallowing his cock and pulling my head back slow with my lips locked around his shaft. I bob and twist my head, pumping the base in time with my strokes to my own cock.

"Fuck, Silvers, I'm gonna cum," Jack moans, pulsing in my mouth and aching for release. "Drink it all down."

He doesn't need to tell me twice. I don't plan on letting this delicious cock out of my mouth any time soon. I deepthroat him one last time and, as I pull my head back, he fires streams of thick, bitter cum down my throat. Though I try to swallow it all, a few drops escape and drip down my chin.

I pump my cock with short quick strokes as I suck every last drop from Jack's balls. Even as he goes soft in my mouth, I don't stop until I cum into my hand. Then, I let Jack slip from my mouth, coating my chin in even more cum and saliva.

Breathless and grinning up at Jack, I say, "Is there any chance I can get a regular reservation at this restaurant?"

The guard leans down and wipes his finger over my bottom lip and chin. "I'll consider it." My heart skips a beat when he flashes me another flawless smile.

After he leaves, I check the clock. It's time to go.

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