In my early twenties, I made some poor choices and ended up in jail facing up to ten years in prison. Now just to clarify, I lived in a small Midwestern town, so it’s not like I was headed off to pelican bay or Chino, but prison is prison. As a youth, I had been a bit of a malcontent and spent time in mental institutions but nothing like adult prison.
Growing up, I found myself confused about my sexuality. This was in part because my dad ridiculed me and made nasty comments about me being gay. The other part was because of my dad’s comments, I began to insert things – my fingers, beer bottles, etc., into my ass while I masturbated. Of course it hurt at first but it also felt good. Unfortunately due to my father’s negative opinion of gay men there was also shame and confusion. I wondered if I liked fucking my ass was I gay?
Fast forward ten years and several treatment centers later, I was at peace with my sexuality. I considered myself to be a bisexual male with leanings towards women. So at the time of my incarceration, I was married. We didn’t have the best relationship before I ended up in jail and it went down hill once I was arrested. At my sentencing hearing my wife told me to expect divorce papers.
The ward I was on was long and narrow. On one side, bunk beds hung from the walls of two man bays divided in half by a bathroom area. The other side consisted of five round tables with four seats each. A camera pointed down the hall.
I knew most of the guys in the ward from before I posted bail. There was one new guy. He stood about 5’ 7” and weight about one eighty. He had a broad chest with large pectoral muscles and nearly six pack abs. His upper arms were at least one quarter bigger than mine. His skin was very dark and he had almond colored eyes.
Now most of that didn’t matter to me except to elicit envy, however his eyes were beautiful. He went by Nashville. He was transferred to our Ward from downstate for a hearing. We ended up as partners in spades that first night. We ended the night undefeated.
Three nights later, we we’re both up late. He was stressing about his hearing but hiding it better than I was hiding my stress of going to prison. I was 6’2” tall, a hundred and seventy pounds of somewhat lean muscle, and long wavy reddish brown hair.
“I know some people downstate. I can send a kite with you to give to them and you’ll be taken care of,” Nashville said to me after a while.
“Not to be a dick,” I said, “But what do I have to do for this kite?”
“I’m gonna need you to get me off,” he said, “Twice.”
“Excuse me?” I replied.
“What I really want is to fuck that ass of yours,” he clarified, “But I’ll accept a good blow job.”
“You know I’m not gay right?”
“It’s not about that,” he said, “I’m not gay either. But I have been locked up for seven years with five more to go. Masturbation gets old.”
“You’ll have to let me think about this,” I said after a long pause. The problem was mostly a question of trust. How did I know that he would follow through with his promise. And that the note would even matter. In the end, my curiosity won out over my concerns.
“Ok, here’s the deal,” I said, “If we do this, than I’m in control. I do it my way, got it?” I said to him, “And I’m going to get off too.”
“Of course, I wouldn’t have it any other way,” he said with a wicked grin.
There was an unoccupied bay just past the shower area. We agreed to move our stuff to that bay. He called the bottom bunk which was fine with me. Since everyone else was asleep, moving a vinyl mat and a plastic tote silently was difficult, but we managed. The bay was fairly dark, but we could still see well enough. I put my mat on the top bunk and my box of stuff under the table, leaving my hair conditioner out on the table.
Nashville laid on his bunk on his side. He was shirtless, wearing nothing but boxers. I pulled off my shirt which was like a scrubs shirt but heavier and less comfortable. I left my pants on, and laid down next to him. He started rubbing on my chest and licking my nipple. The sensation sent a shock of pleasure through my body. I was quacking from the adrenaline of doing this for the first time. He continued to lick my nipple as his hand drifted into my pants. He grabbed my cock gently and began to stroke it.
“Mmmmmm,” the sound escaped my lips. I pulled his dick out from between the flaps of his boxers. He wasn’t fully hard, though his cock was long already.
I slid off the bed, grabbing the conditioner bottle on my way to the floor. He scooched over to the edge of the bunk and turned on his side. I squeezed the open conditioner until a generous amount escaped from the top. With my left hand, I scooped up the glob of white cream on to my first three fingers. I took a hold of his cock with my right hand and as I licked around the head, I rubbed the conditioner on to my asshole.
My fingers slid in to my rectum easily. I carefully enveloped the head of his cock with my lips and sucked on it like I was giving it a hickey. I slowly moved my mouth down on his dick until I felt like I would chock. I moved my mouth up and down while continuing to suck in. His dick got stiffer but not much bigger.
He started pulling on my shoulder and said, “Lemme git in that ass.”
I stopped sucking his dick and pulled my fingers out of my ass. Still holding his cock in my one hand, I took off my pants. He started to move like he was going to get up, but I clenched my hand, stopping him. Naked with my dick hard as ever, I grabbed the bottle of conditioner and towel and climbed back on his bunk. I straddled his legs and released his dick to remove his boxers shorts. I laid out the towel on his rock hard abs. I poured a generous amount of conditioner into my left hand and stroked it on to his cock. I rubbed the rest of it on to and in my ass.
The upper bunk was a little lower than I would have liked, but I was able to stay mostly upright. Nashville’s dick was bigger than mine though not bigger than the dong I used at home. I lifted myself up which meant bending my back forward slightly, and positioned myself above his cock.
Up to this point, I assumed that Nashville only wanted to fuck me because I had long hair and in certain positions he could imagine that I was a woman. My arousal came not from Nashville himself, but rather from the situation. I grabbed his cock with my left hand, intending to guide it into my anus. Because of my forward lean, I started to lose my balance, but Nashville caught me. I looked at him and he was looking back at me.
With him steadying me, I maneuvered his dick to my man pussy. I rubbed the head of his cock around a few times, coating it in the remaining conditioner, before inserting it. Once I felt the tip enter my rectum, I slowly lowered myself until I hit the wall. I found that when inserting large objects into my ass, there is a point where they become painful and it becomes difficult to push past. I also discovered that if I wait a moment and relax, the muscles in my rectum shift from push to pull. I waited for this to occurred with Nashville.
We only had to wait a couple of seconds before my ass shifted gears. As soon as I felt the wall give, I quickly lowered myself all the way down his dick. The sensation of him inside me was completely different from anything I experienced prior. The presence of his warm hard cock sent waves of pleasure through me. I started to ride him up and down, slowly at first but gradually increasing.
As my speed increased, Nashville shifted his legs for leverage. He thrusted his hips in time with my descent increasing the euphoria. He suddenly grabbed my cock with his right had, jerking me off at the same time. I felt myself getting ready to cum and I felt him swell as well.
“Fuck yeah, make me cum all up in yet ass,” he growled softly.
“I’m gonna cum all over you,” I replied.
I couldn’t hold it any longer. My first burst shot out on a hard down thrust. His started a moment later. He slammed his cock with each shot. I could feel his cum filling my asshole while mine shot out past the towel onto his chest.
“Ggrrruph,” we moaned in unison.
It didn’t take long for us both to be spent. He wiped the last glob of my cum from the tip of my dick and licked it off. I leaned forward as his cock softened in my ass and lick my cum from his chest. With it still on my tongue, he pulled my mouth to his and kissed me deeply. While we kissed, I lifted my hips causing his dick to be expelled from my ass. I used the towel to clean up my ass and his dick.
“That was incredible,” he said finally.
“Ain’t that the truth,” I agreed.