Prison Buddies

John stared down at his plate. The food wasn't great, but he was hungry after being worked hard all day, his first day in prison.

He'd arrived the day before, but that was mostly showing him his cell, explaining the rules, things like that. By the time everything was sorted it was lights out. He'd been woken this morning early, taken to breakfast, then shown where he'd be working in the laundry.

"Only 3 years of this" he thought. He'd gotten into a fight at the bar and badly injured the other guy. He hadn't started it, but he made sure he was going to finish it, and in doing so he went quite a bit beyond self defense and wound up here.

He looked up as someone sat across from him at the table. It was his cellmate. John guessed he was about ten years older than him. They hadn't spoken last night, and John had kept to himself all day, so he didn't even know the guy's name. "You're taking up me other bed, ain't ya?" the guy asked.

"Uh, yeah." Not wanting to make hostilities already, he added "but I didn't know which to take, so I just jumped in one. Sorry."

"It's all right, you picked the empty one. Henry's my name" and he held out his hand. John replied with his own name and shook it, and promptly had his hand crushed. The man had surprising grip strength.

Seeing him wince, Henry quickly relaxed his grip and looked apologetic. "Fuck, sorry about that, friend. You get used to squeezing hard in here, guess I forgot my own strength. Anyway, I'll be off, just wanted to meet ya. I'll see you later anyways when it's home time. We'll be getting to know each other pretty fucking well, so no point rushing it ay?" And he left.

'He seemed alright' John thought. He finished his dinner then went to his cell. He was tired and just wanted to relax a little.

By the time Henry came in, John was nearly asleep. Not wanting to lose the headway he had made towards passing out, he pretended to be already sleeping so Henry wouldn't talk. It worked, and soon John was out cold.

The next day after lunch, everyone was outside relaxing and doing whatever they were allowed to enjoy themselves. John was sitting down bored shitless when Henry came up to him. "Ay man, didn't get to talk last night cos you were already sleepin, didn't wanna wake ya."

"Oh, thanks for that. Yeah, I was really tired after yesterday. Haven't been worked like that for a long time"

"Yeah, it'll be shit the first few days of it, but you'll get used to it fast, everyone does."

They talked for a while, getting to know each other. Henry had been inside for 12 years, but John didn't want to ask what he'd done. Because Henry hadn't asked John, he didn't know if you asked people that question. They'd been talking for an hour or so, when a guard called a 5 minute warning.

Henry stood up to leave, then turned back and said "remember how I said we'll be getting to know each other better?

"Yeah?" John replied.

"Well, tonight will be it."

"Tonight will be what?" John asked, no idea what Henry meant. Was he gonna introduce him to a prison gang or something?

"Well tonight I'm gonna stick my cock up your arse." he said with a grin.

John froze. He opened his mouth to speak but no sound came out. How do you reply when someone tells you they're going to rape you in a few hours? "Haha, I can see you weren't expecting that. You seem like a decent enough fella, so I'll make you a deal. You got 4 choices here. Choice number 1: you tell the guards. Not really much they can do apart from put you in solitary for protection, but they probably won't cos it's a hassle and they got no proof. You do that, I'll beat the shit out of you then rape you. Option 2: you tell me to get fucked. Do that and I'll rape you. Option 3: I give you my steak from tonight's dinner, and you let me do it. I'll try not to hurt you, and I'll wear a condom as well. Final option, you take my steak and then change your mind about letting me. That'll get you bashed and raped. My advice? Take option 3. You won't get bashed, it won't hurt as much, and I'll wear a rubber so you won't get me cumming in your arse. Best decide by dinner." He gave John a nod and left.

John sat in stunned silence. He didn't know how to process this information. He didn't want to move because it would mean he would have to face what was coming, but the guards called everyone in, so he was forced to stand and walk inside. He tried to think about what to do. Telling the guards would keep him safe for a while he though, but when they sent him back to the main prison population he'd be paying for it. He could try to fight Henry off, but he was far stronger than John, and guessing by the fact that he'd been here for over a decade, he likely knew how to fight. John knew how to fight too, but prison rules was a different sport entirely. Then he remembered option 3: let Henry do it, and get an extra steak at dinner. He even said he wouldn't be as aggressive and he'd wear a condom. That was his best option, he realised sadly. He was going to get raped either way, he may as well take the 'best' option. But the idea of willingly letting a man fuck him made him want to vomit. He didn't know what to do.

Before he realised it, he was in line for dinner. He'd been thinking the entire time and hadn't even noticed he was walking here. He took his food and walked to the far back of the room and sat down. He wasn't even sure if he'd be able to eat, but if he didn't eat now he wouldn't be eating until breakfast, so he went to take a bite when Henry sat opposite him.

John looked at him with fear and revulsion. Henry said nothing, but stabbed his steak with his fork and held it out to John.

John knew this was the moment of truth, but he didn't want to take it, because that would mean he was accepting his fate.

"Offer's only gonna be in the air for so long John" said Henry.

John's muscles wouldn't let him move his arm, but he gave a small quick nod. Henry saw it and dropped the steak on John's plate. "Good lad. I'll see you tonight".

Tears wet John's eyes as he felt the shame of his decision reach him. Henry had turned to leave, but quickly sat back down. Leaning in, he said quietly. "Cut that the fuck out, right now. If people see you crying in here they will make you regret it."

John couldn't understand why Henry would give him helpful advice, and apparently the confusion showed on his face, because Henry said "I should have told you. You take this option, you're under my protection. Nobody will touch you if I say. But I can't stop them from making your life hell for the rest of your time here." Then he left.

'Make my life hell?' John thought incredulously. 'Aren't you doing that right now?' He shook it off and tried to put it out of his mind.

After finishing his dinner plus extra steak, he slowly trudged back to his cell, trying to take as long as possible. When he arrived, he saw Henry sitting on his bed reading. John nervously sat down on his own bed, and looked across at Henry. He summed up the courage to speak and blurted out "why are you doing this?"

"Feel like getting off and it's better than a wank. You might like it yourself."

"If you think I'm going to enjoy it you're very fucking mistaken."

Henry shrugged and kept reading. John kept staring at him, and he eventually looked over. "Not until lights out, so you may as well find something to keep yourself busy."

John was angry at his nonchalance, but didn't want to anger Henry in case he reneged on his deal to go easy. He lay down and stared at the ceiling, wishing he was anywhere but here.

When the call came for lights out and the cells went dark, John started to panic. The time was now and he couldn't avoid it. He waited, but Henry did nothing but remain on his own bed. 'Maybe he fell asleep?' John thought hopefully. But after a minute or so Henry stood up and simply said "clothes off" and started removing his own.

Standing nervously, John began to feebly remove his clothes. He couldn't help but look, and saw in the dim light that Henry had a normal sized cock dangling softly between his legs. Breathing a sigh of relief that it wasn't enormous, he sat down on the bed naked. "On the bed, hands and knees" barked Henry. John complied, his own cock and balls dangling as he stuck his arse out. Henry sat behind him and started rubbing his hole with his thumb. It was so sudden that John jumped away in shock. Henry said nothing, but pulled him back and resumed the rubbing. "Just doing this to get you ready otherwise it'll hurt more. Trust me, this is for you. I don't particularly enjoy playing with your arse, but I made a deal to make it easier for ya. And take my advice, if you clench it will hurt. A lot. So relax."

John felt sudden wetness and realised that Henry had spat on him. He felt Henry rubbing it in, then felt pressure as he slid the tip of his middle finger into his arse. John's mind froze. He'd never had anything go in there before in his life, and now another man was fingering him in preparation for anal sex. He stared at his pillow, trying to will his mind to a different location. It worked, but only partially. He couldn't completely block out the feeling of Henry's entire finger sliding in and out of his arse at a steady pace, but it helped.

Feeling Henry withdraw his finger and shift around on the bed, he turned to look and saw that Henry was on his knees behind him. He spat in his hand and rubbed it all over his now fully erect, condom-wrapped dick, which, while bigger than it was before, still wasn't much bigger than average. John started breathing faster, panicking again. Henry moved forward into position, and John quickly turned his head away. He couldn't watch this. But he could certainly feel it.

The head of Henry's cock nestled in between his spread cheeks, he felt it push inside slowly, then retract without going past the barrier. Henry repeated the process, constantly pushing and pulling back, never going in. John assumed he was trying to loosen the hole, and judging by the fact that each time Henry would push just that little bit further and pull away a little bit less, he was right. After a few moments of this, he felt Henry break through his tight sphincter and stop. It hurt, but only enough to cause wincing. Henry slowly started rocking his hips slightly, giving himself about an inch of movement each way. With every few pushes he'd move a tiny little bit deeper, and John would quickly get used to it. Within a few minutes, John felt Henry's stomach against his arse cheeks.

John's head swam with the realisation that another man was now balls deep inside his arse, but he didn't get to dwell on this knowledge before Henry slowly started pulling out. Just before he popped out, he started pushing back in again. Once he realised John wasn't in pain anymore, the thrusting picked up a little bit, until it was a steady pace. In, out, in, out. John tried to will his mind away again, but unlike the finger, he had no chance this time. Henry's rigid cock invaded his every thought, so that all he could think about was the friction of it sliding against the rim of his hole, and the head pushing against the walls of his colon. He breathing slowly became heavier, and the whole time the pace never changed. In, out, in, out.

"How much longer are you going to be?" he asked without even really meaning to.

He heard Henry snort. "Didn't I tell you?" He spoke without stopping. "I don't cum until I want to. And I don't want to cum until you do."

John's eyes went wide with shock. Henry had to be completely stupid if he thought John would cum. But he didn't know how to respond, and before he could think of one, Henry's cock brought him back to being under the spell it seemed to put on him.

He suddenly became aware of everything about his own body. His hands supporting his own weight, his neck keeping his head up, his balls swinging underneath him and his plump cock with it. Wait, his plump cock? Looking down, John saw that he had become partially swollen. 'What the hell? Why am I getting hard, I'm not enjoying this' he silently demanded of himself. But he wasn't so sure of that anymore. There was no pain, nothing but smooth gliding in and out.

He felt Henry stop and put his legs together, raising him up to come in from a higher angle. When he resumed the fucking, John knew that would now be telling a flat out lie if he said he wasn't enjoying this. Due to the position change, Henry was now hitting his prostate with every thrust, and it was making his dick grow steadily harder, until he was sporting a full erection, wobbling around as Henry fucked his arse. The longer it went on, the better it felt. He was beginning to feel it in the base of his cock, a feeling he couldn't describe, but one he very much enjoyed. But at the same time, he was determined not to show it, except he couldn't help it. His ragged breaths had picked up, and had now turned to sighs that matched Henry's thrusts. Looking at his watch, he saw that he'd had a dick inside him for a little over 20 minutes, and Henry was showing no signs of slowing down; he kept up the relentless thrusting. In, out, in, out.

John's sighs were becoming more audible now, and he knew there was no way Henry wouldn't hear him.

He felt Henry's hands grab him under the arms all of a sudden and lift him so he was kneeling straight up. He felt the difference instantly. Whereas before, Henry's cock would hit his prostate with every thrust in, he was now angled so that it was rubbing it with the entire length, on the way in and out. There was never not pressure on it, and it felt unbelievable. John let out a small moan without meaning to, and he felt shame and horror at himself, but also indescribable pleasure as Henry started going faster. John's cock was bobbing up and down, and it was leaking precum all over his bed. He didn't care. All he cared about was the pleasure he was feeling. The tingling friction of his sphincter, the incessant rubbing of his prostate, the pulsing in his cock, which had now grown from the base to the entire length. It felt like someone was lightly tickling his cock with a thousand feathers, and he didn't even try to hold backs his moans.

He suddenly felt his arse start pulsating, tightening and loosening all of its own accord, and he knew his orgasm was coming. He didn't even feel ashamed anymore, just ridiculously turned on at how good it felt.

His toes started tingling before going numb, his moans become short grunts, and his entire upper body started flopping, and his orgasm tore his world apart. It started in his arse, and he could feel himself orgasming for several seconds before it moved from his arse to his cock, and he exploded cum all over his bed. He thought he would be done about now, but it kept going and going, coursing through his body in waves, all emanating out from his arsehole. After what felt like several minutes, he could feel his orgasm residing, and Henry's thrusts turned from steady to jerky, and he quickly and violently came inside John, the condom saving him from having his arse full of another man's seed.

With Henry's cock softening inside him, John pulled away, and felt it pop as it fell out. They both stayed in the same position, catching their breath for a few minutes, then Henry got up and moved over to his own bed and sat down. "Told you I'd make you cum. And if you thought that was good, then I'd advise you to go without the condom next time. It's much better" and he lay down, still breathing heavily.

John looked over at him. "Next time?"

"Don't give me that, you loved it. Most people take over an hour to cum. You did it in about half that. You want my cock again, and you're gonna get it. Now go to sleep, you need your rest. Until next time."