Prison Buddies

*note: I suggest reading chapter 1 first*

***

John's eyes slowly opened. He had been dreaming. Like every night for the past week, it was the same dream - the recollection of when Henry took his anal virginity. And just like every other night, he was sporting an erection so hard it was almost painful. And also just like every other night, the first thing he did was to make sure Henry was still asleep, then masturbate, thinking of his dream.

The first 2 mornings he had cried afterwards at the shame of what he was doing, and while there were no more tears, the shame was still there. He couldn't help it though. There was nothing that turned him on more than the memory of how good it felt to have another man's penis inside him. How amazing it felt to have his prostate stimulated. How intense it was to cum purely from being fucked in the arse. Recalling the memories made him cum with 30 seconds of starting to masturbate. He caught it in his hand and quietly got out of bed to throw it down the sink in the corner of the cell.

Sitting down on the toilet to recover, he put his head in his hands, disgusted with himself once again. It had been 5 days since, and Henry hadn't made the slightest recognition that it had even happened. He said that it would happen again, because he knew John liked it, but it hadn't. John didn't know how he felt about that. On one hand, he didn't want it to happen again as he wasn't gay, and being the bottom for another man was humiliating, but on the other hand, he was already starting to feel himself grow hard again at thinking about it. He certainly wasn't going to let Henry do it without a condom, as he had recommended. He shook the thought out of his head, and tried to keep it out. Henry was starting to wake up, which meant it would be time for whatever work they were assigned that day.

***

Staring at the ceiling, John waited until sleep came. Despite working hard all day, he wasn't very tired. A noise made him look up, and the source made him sit up in shock. It was Henry, completely naked.

"Come on, pants off. You know what time it is."

John sat in silence, his mouth moving but no words coming out. He had been completely by surprise, and didn't know how to react. His body apparently did, as within seconds he was completely hard. Hoping the thin blanket covered this, as he didn't want Henry to see his arousal, he stammered. "Uh, you...what? I don't-"

Henry held up a hand and John fell silent. "Stop talking, take your pants off, and turn around." There was no aggression, no violence or anger in his voice. It was completely calm. It wasn't so much a demand as it was an instruction on what to do next.

Still in shock, John slowly turned around into his knees and slid his pants down, exposing his naked bum, and dropped to his hands so he was on all fours. It only took a second before he felt a large glob of spit plop onto his ring, before being softly massaged in, and the pushed inside him with a finger. Tensing his body at the sudden intrusion, he took a deep breath. If someone asked him if he was glad this happening again, he wouldn't know the answer. After a while of silent fingering, the finger was removed, and John felt something larger and smoother take its place. His eyes went wide and he instinctively tried to pull away, but the hands on his hips kept him in place, and Henry's cock slowly pushed in, and crossed the barrier.

A short gasp from John was all the noise made as Henry slowly penetrated him, pushing deeper and deeper, until finally he bottomed out. He stayed there a moment, letting John's arse get used to the new tenant, before slowly beginning to pull out. The instant John felt the hard cock slide out, his eyes rolled, and he had to catch his breath in his throat to stop himself from letting out a moan. The fucking hadn't even started and it already felt amazing. He suddenly realised why: Henry wasn't wearing a condom. The skin on skin contact was absolute bliss, as was the warmth. But no, John didn't want this. He didn't want an STD. He looked over his shoulder at Henry.

"Are-are you not we-wearing a condom?" The words came stuttered due to his body twitching in pleasure.

Henry stopped his movements. "Nope. I told you it would be better. You can relax anyway, I'm clean. You're not gonna catch anything." He then looked John directly in the eyes and pushed back in. John's eyes rolled again, and he only just managed to catch himself from moaning, but the look on his face was unhideable. Henry knew how much he was enjoying this.

Turning his head away, he felt the pace slightly pick up. It only took a few seconds, but he let out a long and quiet sigh of bliss. He couldn't hold it in any longer. He began to care less about his shame being witnessed, and fell into the spell of sexual intoxication.

"How's that?" Henry asked.

"Good." John replied, not even hesitating or attempting to hide the truth.

"I actually meant does it hurt, but I guess you don't want me to stop?" He changed tempo mid question, so instead of a smooth in/out, he began to slowly pull out and quickly push in. The first time he went in, John gasped long and deep. He hadn't been fucked hard last time, so this was a new and *very* welcome feeling. "Huh, I guess that's a no then."

"Ohhhhhhhh, never." He only realised after replying what he had just said. His faced burned with embarrassment and shame, so much so that it took his mind off what was happening, and all he felt was humiliation at his admittance of how much he loved it. He heard Henry smirk, then felt him ram in even harder, washing away his momentary shame. "Oh my god, oh, oh fuck." He couldn't keep his words to himself anymore, the dicking was too good. His own dick was pointed straight at his face, having never lost the erection. A string of precum stretched all the way down to the bed, and seeing this pushed him over the edge.

The pleasure, coupled with know how his own body was aroused, ignited each other into an explosive orgasm even more intense than the first time. He felt Henry spank him as he was cumming, which somehow turned him on even more. The orgasm lasted for what felt like a century, and eventually Henry's thrusting changed as the pulsing sphincter around his cock had the same effect as last time, and he began to cum, shooting his load deep inside John, who was even more ashamed to find that he enjoyed it. The tiny flicks of pressure as the cum hit the inside of him felt incredible.

Henry eventually fell still, and remained where he was, catching his breath for a few moments. After a moment's rest, he pulled out. "I'd suggest going to sit on the toilet for a few minutes. You wanna get that all out before you do anything else."

John remained where he was a moment, the shame hitting him like a truck now that the arousal had worn off. He quickly hobbled over to the toilet and sat down. He did his best to hold back the tears of shame as he felt Henry's semen leaking out of him.

"That was a good fuck. I told you it'd be better without a condom. You were loving it from the very start", he finished with a cockiness in his voice.

John didn't answer. He was too embarrassed to speak. Everything Henry said was true, and it was making him feel more ashamed. Even more embarrassingly, it was beginning to turn him on again, Henry lording his victory over him like that.

Henry spoke again. "I didn't even have to make you a deal that time. I just told you to get your pants off and you did it, no questions asked."

John's eyes widened. He didn't even realise this until now. Last time, Henry had offered him his steak at dinner in exchange for John letting it happen. It was either that or get violently raped, so John agreed. But he had just accepted this time. His dick began to grow again once he realised this.

"You wanna know why?" Henry continued his taunting, walking over until he was standing right in front of John. "It's because you *wanted* it. You loved getting fucked by me, and you couldn't wait for it to happen again. Couldn't you? Go on, admit it."

John looked up at him, and attempted to deny it. It was a lie though. He had wanted it. But he couldn't admit it, so he dropped his gaze back to floor. The arousal had reached its limit, and he was completely hard again.

Henry smirked again. "I knew it. Look, you're already hard again. Your arse is mine now. I'm gonna fuck you again, don't you worry. But this time, it's not gonna happen until you ask me to."

John looked up at him in shock, but he had already turned away, getting into bed and rolling over without even giving John another look. He had to be crazy if he thought John was going to ask for it.