Man to Man

Info Tristan LeMay
15 Sep. '16

   I’d been in prison for 132 days and counting. I had 68 days to go before I reached two thirds of my sentence, which in the provincial judicial system here, meant that I could get out automatically if I behaved myself. This was the longest time I’d gone without sex and I was becoming hornier and hornier every day. Sure, I tried to compensate with exercise and I was becoming more and more buff, but I still needed to get my rocks off once in a while.

   I’d happen to come across a book about this young dude that had gotten hooked on hooking, quite literally. He was in College and was having a hard time paying for tuition and, one night, coming home from a party, had gotten picked up while hitching and had made 40 bucks blowing the dude that had given him the ride. Just the author's description of the blow job had made me crazy with lust and I’d started jacking off in my bunk with my cell mate snoring right above me, oblivious to what I was doing, thank God!

   Yeah, ‘cause although there was probably plenty of sex going on in the wing of the prison, I never got any inkling that it was okay to jack off or anything ‘cause nobody ever talked about it. Except once in a while when some guy would start ranting ‘cause he’d used the shower and found the walls covered in jism and started screaming that the “fucking asshole that did that and didn’t clean up after himself was just a fucking asshole”. Yeah… vocabulary wasn’t a big thing in the wing.

   Anyway, reading that novel with the College dude discovering he liked making money sucking off rich old guys or getting fucked by powerful politicians that would give him plenty of cash to cover his tuition, I started jacking off again after 121 days of not even touching my dick except when I took a piss.

   After a few days of enjoying my nightly jack-off session to a new chapter in the book – for the life of me I can’t remember the title of it now –, I became more and more careless. Although I always made sure to jack off pretty much under the sheet until I was ready to cum (at which time I'd just pull it back so that I wouldn’t be stuck sleeping in my own spunk), I started not paying attention to the guards’ check rounds and had to act innocent a few times, slapping my hard dick against my belly and looking really concentrated on the page I was reading so that I wouldn’t get in trouble. I also started not caring whether or not Miguel was asleep or not. I’d just jack off and make sure I didn’t make too much noise because, some nights, he’d read a bit, too, so I couldn’t wait for him to be asleep.

   Then, around day 130, I came into the cell in the middle of the afternoon and found Miguel, my bodybuilding, dark-haired, Latino cellmate, taking a nap like he often did when he had gone to the prison gym in the morning. I made sure I didn’t make too much noise while I sat at the little table we shared and started writing a letter to my sister who’d sent me a note a few days earlier. As I was writing, I suddenly started hearing moaning and plastic crumpling. When I turned around, I saw Miguel lying on his stomach, humping his green, vinyl-covered mattress, his bubble-butt bobbing up and down in a regular motion. I smiled and tried not to laugh, but then, I found myself caught in the scene and couldn’t take my eyes off that ass. I started imagining Miguel fucking his Latina girlfriend – he’d told me her name was Vanessa – and started getting hard.

   – Oh fuck no! I said to myself. This isn’t the time OR the place, you idiot!

   So I pulled my eyes away and concentrated on my letter to my sister. That was a great way to calm my carnal instincts because I’m not into incest so my sister, well… she’s my sister. That’s it.

   After a while, Miguel stopped humping the mattress and I sort of wondered if he’d climaxed, but I certainly wasn’t going to ask him. He just kept on sleeping straight through till we were called to dinner.

   That night, as I was reading chapter 19 of my hot novel and getting another hard-on, I started hearing the sounds that had made me turn around in the middle of my letter-writing in the afternoon. Miguel was humping his mattress again. As I kept on reading, learning about Nicky’s – yeah, that was his name – evolving relationship with a city councilman that had become a regular client and who was slowly turning him into a soft BDSM addict, I was beating my meat, getting even more aroused by Miguel’s moans and pounding his cock into his vinyl mattress. My imagination was in overdrive: Nicky’s ass getting whipped by the councilman who was beating his own half-hard cock while his young hooker was rock-hard, and Miguel’s iron-hot Latino pole drilling into his Latina girlfriend’s brown, wet pussy.

   I pushed the sheet off myself just in time to avoid shooting strands of hot jism on it, biting down on my lip so as not to wake up my horny-as-hell cellmate. I barely had time to grab the roll of sandpaper-rough toilet paper I had stuck between the wall and my mattress that I spotted the guard’s flashlight coming closer. I cleaned myself off the best I could in five seconds, threw the spunk-filled tissue under the bed and turned on my side, covering myself with my sheet.

   The flashlight’s beam swept through our cell and the guard was gone again, until his next round in about four hours. I basked in the after-glow of my own self-inflicted orgasm and felt really good. As Miguel was still humping the mattress, I probably could have started playing with myself again because I was still hard, but I decided it was better to just try and get some sleep.

   The next night, around day 131, I was nonchalantly stroking my cock while reading the next chapter in Nicky’s adventures in male hooking when I heard Miguel’s humping of his mattress again. This time, I don’t know what got into me – maybe it was because the guard had just done his round and I knew he wouldn’t be back around for another four hours – , but I pulled off my shorts and stood up next to the bed, my shoulders at the same level as Miguel’s bunk. Although it was very dark, the moon and the floodlights from the yard did provide some light through our small slit of a window.

   I started jacking off, watching Miguel’s bubble butt bob up and down on his mattress. I couldn’t help but wonder how firm it was, knowing that my cellmate went to the gym to pump iron four times a week, did squats and all sorts of other exercises on a daily basis… to keep his body and his mind fit. I could feel my cock getting harder and harder as I stroked it, hearing my cellmate’s moans and groans and wondering why he wasn’t covered up by his white sheet. I moved my face closer to his butt to see what type of underwear he had on. They looked like body-hugging boxer shorts. Kind of like those tight legging-type pants cyclists wear, just shorter.

   In following Miguel’s rhythm in humping his mattress, I began fucking my right hand, making a tight fist that rubbed on my cock and pulled back my foreskin with each stroke. I knew if I dared touch Miguel’s ass or tried to grab his cock in an up stroke, he’d probably punch the living daylights out of me. As I was saying in the beginning, guy-on-guy sex was probably more popular than I knew in the wing, but nobody’d tried to have their way with me or made me any propositions which was really starting to get to me. Part of me kept thinking, “He’s been fucking his mattress for weeks, maybe he’d like something with a little more human flesh!” but the other part of me was saying, “He’s always talking about how hot his girlfriend is and how much he looks forward to seeing her again. You’re gonna get pummeled if you try anything!”

   But I couldn’t take it anymore. I was ready to get beaten to a pulp for even just a chance to feel my cellmate’s flesh, touch his hard cock, make him moan even more… I traded my right hand for my left hand on my pole and started jerking myself off with my weak hand. Slowly, I placed my hand, palm facing the ceiling, on Miguel’s mat and slowly slipped it under him in one of his up strokes. His massive cock, although wrapped in his skin-tight boxers, was very clearly fully erect, hard as an iron pipe. I wrapped my fingers around it as best I could, feeling the mix of Lycra and cotton of his briefs. He moaned a bit differently but didn’t wake up, so I squeezed his dick on every down stroke, acting as some sort of pocket pussy. It felt so nice to touch another person, to actually have physical contact with another human being after all this time.

   Although I felt a bit clumsy, I did manage to keep beating my own cock with my left hand. As a matter of fact, I felt so aroused by my boldness and Miguel’s building pleasure that I soon sensed my orgasm nearing. I let go of my cock which started bobbing around like a catapult snapping back, and put my left hand on Miguel’s right ass cheek, kneading it like a round ball of bread dough, pressing down in harmony with my squeezing of his bulging cock. He moaned even more. My heart was beating faster and faster, butterflies churning in my stomach as my cock bobbed up and down, swaying freely for the first time in months.

   As Miguel kept humping the mattress and my hand, I decided I wanted to take this a step further. I slipped my left hand inside his underwear, feeling his ass crack with my fingers, and slipped my right hand inside the front of his briefs, making contact with the flesh of his cock and feeling my fingers get tickled by his thick pubic hair. Very quickly, I decided to yank his boxers down to his knees because I wanted to get a glimpse of his ass and get a better feel of his cock and balls.

   This was not a good idea. He suddenly woke and turned around to see what was going on.

   – What the..,

Without thinking, I drew my right hand to his face and covered his mouth, bringing my own face close to his to whisper:

   – It’s just me, man. Relax. You were humping your mattress. Just lay there and let me make you feel good.

   His eyes were wide open, as large as saucers. After a few seconds, his tense body just went limp, like he was surrendering to my touch. I slowly took my hand off his mouth and swept down his muscular torso to his crotch. His cock was pointing to his face, rigid and unbending against his pubis and his belly. I was impressed with how long it was but especially by its girth. Man, it was almost like a soup can! I brought my face closer to it so I could get a closer look in the dim light. I stroked it with my right hand, assessing it in more detail, in awe of the huge, pulsing vein of its underside, and Miguel groaned:

   – Yeah, vato, stroke it, he whispered.

   I did, having trouble wrapping my fingers around it completely. I pulled away his foreskin and uncovered his dark, mushroom dick head, glistening with pre-cum. He started fucking upward into my hand, bouncing off the bunk.

   – Mmmm… that feels so fucking good, vato, he whispered again. Yeah!

I kept my hand in place, wrapped around his mammoth meat so he could fuck it. Then, I used his cock as a lever to pull myself up, planting my feet on the bottom bunk and grabbing his balls with my left hand. He winced.

   – Easy, vato… I haven’t fucked in months, you know…

I knew. Oh, yeah, I knew alright. I knew plenty.

   – Sorry, I whispered.

And as he was saying:

   – That’s alright.

   Without thinking but as to win his forgiveness, I opened my mouth and just swallowed his pole whole, taking as much of it as I could.

   – ¡Puta madre! he whispered but a little too loud.

I pulled my mouth off his meat just long enough to shush him.

   – Holy fuck, vato, you’re sucking my dick!

   He said it with clear amazement in his voice, like he couldn’t believe it. I knew how he felt because I couldn’t believe it myself. All I knew is it felt fucking great after having had no sex with ANYBODY in all these weeks of incarceration.

   I bobbed up and down on his humongous cock, sucking it into my throat without gagging – which really took me by surprise –, licking it, nibbling at its head, holding the base of it with the index and thumb of my right hand while my left hand pulled at his balls and squeezed them, probably hurting him a little, but in a good way. After a while, I let him fuck my face, opening my mouth wide over his pole and taking it deep in my throat. I didn’t even mind when he grabbed my hair with his right hand to fuck me even harder.

   – Oh vato, this feels so good. Yeah, take it. Take my big dick. Mmmmm… Chupa mi gorda verga, vato. Mmmm…

Then, I started feeling his cum rushing up his pole.

   – I’m coming, vato, I’m going to cum in your mouth.

   He tried to pull my head off him by my hair, but I grabbed his wrist and squeezed, forcing him to let go of me. And he exploded in my mouth with the force of a volcano. My throat swallowed strand after strand of thick spicy, Latino cum, and when he was done, I sucked at his pole, teasing his nerve endings and sending bolts of electricity through his whole body.

   – Holy fuck, vato, he whispered, his breathing heavy and shallow. That felt sooooo fucking good. I didn’t even know you were gay.

   – I’m not.

His head popped up.

   – What?

   – It’s true, man. I never touched another guy’s pecker before.

   He started laughing hysterically.

   – Ssssshhhh!

Again, I put my hand on his mouth.

   – Shut the fuck up. If you tell anybody about this…

   – Oh man, I’m so fucking grateful… you think I’m going to squeal?

   – Well… that was almost like a squeal when you came...

   He grabbed his cock with his right hand and slapped my face with it.

   – Ow!

   – Ssssshhh!

   He was still completely hard. I don’t know what came over me. I reached over to my snacks and toiletries shelf and grabbed one of the condoms the infirmary regularly distributed so we wouldn't spread or contract STDs. I went up the ladder to Miguel’s bunk.

   – What are you doing?

   – I don’t know. But I’ve been reading this book about this guy who takes it in the ass and comes without even touching himself so…

   There were those saucer-size dark brown eyes again. And for the first time, I noticed how long my cellmate’s eyelashes were. I sheathed his massive pole and thought I had to be crazy to let a guy with this kind of girth take my ass cherry.

   I spit on the condom four or five times to lubricate it, making him moan while I spread my saliva on his pole. And then, I spit on my fingers a few more times to try and lubricate my man hole before squatting over him and letting his monster cock poke my anal cavity.

   It hurt like bloody hell but, oddly enough, I was happy it did and my cock just perked up even more. I fucked myself with his huge dick, bouncing on it like I was on a trampoline while I jacked my own pole with complete abandon for the first time in months. At this point, I didn’t care if a guard passed by for a surprise inspection. I’d take any punishment that I deserved, but not before I shot a load of cum on my cellmate’s chest and he shot a load of spunk in that condom inside me.

   – Oh yeah, vato, ride my cock. Shit you're tighter than my girl, man. Yeah!

   I was certainly not surprised by that because nothing had ever been shoved up there before and Miguel had the biggest cock I'd ever seen before, not that I'd seen many in person – especially not hard – but only in porn. What did surprise me was when Miguel's hands grabbed my hips and started gliding up my sides, softly caressing me and making their way to my nipples, under my t-shirt. He cupped my pecs like they were tits and probably felt they were much firmer than his girl's but I didn't care that he needed to feel like a man with a woman. I started oscillating on his dick like a girl and moaning softly to get him even more in the mood. Then, he started pinching my nipples and, to my surprise, this sent a bolt of lightning straight to my hard cock and I came first, pushing my cock down so that he wouldn’t get splashed in the face. But as he started to explode in the condom, I raised my hose and my last jet of cum blasted out of my pole, landing on his chin, startling him.

   – Oh, vato, your ass is soooooo amazing. Yeah! Feel my cum inside you, man. Feel it. Mmmmm….

   We were spent. He was covered in cum. I probably would have licked it off him but felt that might be too gay… so I got down from his bunk and handed him a roll of that shitty toilet paper for him to clean up. He did.

   I slipped my underwear back on and slid back into my bunk, covering myself with that white sheet of mine. I could hear Miguel’s vinyl mattress as he lifted his ass off of it to slip his skin-tight boxer shorts back on. In my mind, I visualized that half-hard, gigantic sausage tightly-wrapped in his underwear, pointing toward his right hip and I felt my own cock twitch in my shorts.

   Maybe this had been our first time having man-to-man sex, but it certainly wouldn’t be our last.