How I Found Love in Prison

Here I was, prison. It'll be a long 6 months I thought, but it'll be worth it. They'll never find the money I embezzled and hid. I'll be rich when I'm out. I'm a young lawyer, slim but not muscular, well groomed, clean shaven with very little body hair, and a head of thick black hair, delicate soft skin. My only hurdle now is surviving prison for 6 months.

I'm not naïve. I know what happens to soft pretty guys like me in prison. I really don't want to get raped, but I know I'll be getting lots of advances from all the big men in there. And so I strategized. I knew I'd eventually get caught and go to prison, so I prepared in advance for my stay to be as pleasant as possible. I didn't want to get raped. So I prepared myself to be able to enjoy it. It's not rape if one enjoys it, I figured.

I've been with a few women, but never with a man. Been straight so far. I previously hadn't even thought about it before, but the money that awaits me when I'm out has all caused me to think differently. It's amazing how money can make a person think.

The main concern, is that I didn't want to get raped. If I am to be with a man, I must enjoy it. So to prepare myself for prison, I decided to prepare my bum. I would lay in bed, naked, touching my soft body and would finger myself in my bum every night. I began with one finger, and once I got used to it, would try two and three, while touching and caressing myself. Eventually I began to enjoy it, and would think of a man inside me. I bought a good sized dildo and would vibrate myself each night. A beautiful feeling!

But no, I cannot think too deeply of such sinful thoughts. So I would stop.

The day eventually came when I was arrested and now here I am, my first day in prison. It's my first afternoon in the facility, surrounded by men. Gosh they looked like such dirty gangsters, much worse than in the movies.

As the guards escorted me through the prison to my cell, at random the prisoners barked at me "He's coming back tonight! He's gonna fuck you good!"

It got me a bit worried. The man whom I was to share a cell with, was apparently a convicted hijacker, rapist, and in for multiple counts of assault. He was a feared leader in the prison, with all waiting his return from solitary confinement.

Night arrived. The guards showed me my cell where I sat and waited anxiously in my pale blue pants and vest, hoping to get a good sleep. And then he arrived, under guard escort.

"Welcome back Jake. Behave this time", the guards said. "This is your new cellmate, Daniel".

"I take top bunk", he said rather dismissively. The guards left and it got dark. I sat on my bed and tried to read a book when Jake brutishly got in my face, standing between my legs while he set up his bed above me. As he dusted his sheets and pillows, face out of view, his crotch bulged out at me from under his old jeans. It looked sexy, but I worried what if it's too big for me. As he dusted his bed, he began to speak. "I'm sure you've heard a lot about me".

I replied, "not a lot".

"It's not all true", he said.

I wondered what he meant but was afraid to ask. Jake unzipped his pants in front of me and went to pee in our common toilet. His dick was out of view but it cast a big shadow on the wall as he stood and pee'd.

"We'll get to know each other very well." His voice was gruff and manly. He was large and broad, with big hard muscles, thick beastly arms. I could see his well-defined abs beneath his tight vest. His chest was hairy, going down to his waist. His armpits were also hairy, and he was wet with sweat, giving off a manly brutish stench like a construction worker after a hard days work. I didn't know what to feel. The look of him turned me on, but he was so dirty and smelly. Being with girls before, I was used to their sweet scent, their rosy perfume. But now I'm overwhelmed by Jakes manly stench. I began to breathe it in as much as I could to get used to it. I took deep breaths.

The fact that he was so feared in prison also made me very worried. What if he whacks me? What if he's rough with me and destroys me? Perhaps this won't be as easy or as enjoyable as I thought, I worried. I panicked and began to whimper, and Jake heard me. He zipped his pants, and without washing his hands got down to look at me, but before he could say anything, I let my words out "Please be a gentleman".

Jake looked at me confusingly with that remark and then smirked dismissively and climbed into his bed and relaxed. With that I felt some relief, thinking that maybe he won't approach me tonight, or maybe he'll heed my request. Nonetheless, I lubed myself generously just in case. After laying awake for some time, I eventually dozed off on my right shoulder facing the side bars as the cell darkened.

I don't know what time it was, but it was in the dark of night when I heard the mattress above me creak, and the sound of a heavy thud on the floor next to me. I was facing the other way and turned to look for what was happening, but I was turned back forcefully. Jake got into my bed, taking up most of the space, trapping me in. Gosh he was so strong! His arms were thick and hard as they wrapped around me. He had big hands.

"I can see you haven't done this before. Don't worry, I'll be gentle" he assured me. His voice was surprisingly soft at night, and actually felt very sincere.

"I just need to keep up appearances here. I have a reputation to protect. But, I won't hurt you. If you can't take it I'll pull out but please keep up the act. They're watching us." Jake continued.

I then figured it out. Jake had built a reputation of a feared and merciless gangster, a ruthless villain in prison that all were scared off. But underneath, he was gentle. He was kind.

He made me feel at ease, like I could trust him. His voice was gruff and manly.

"Ready?" he asked silently.

"Yes", I affirmed.

And with that, like an animal he ripped my vest and my pants. I wore no underwear. This is it, the first time I was exposed to a man! He wrapped his arms around and began spooning me. I could feel his beard stubble, his chest hair, and his oily sweaty torso against my back. He wrapped his right hand around from under me and grabbed my left nipple. And with his left hand he grabbed my dick. Gosh my dick was so tiny in his large rough hands.

In no time, I felt it against me. His pants were off and his dick was rubbing at my bum. It was hot and hard, but wet and slippery. Thankfully he lubed. He wasn't lying. He was being a gentleman. He felt my bum and was surprised to find that I was lubed as well.

"Hmm, you're lubed?" he asked.

"I was kind of expecting this in prison", I told him silently.

Jake then smirked. "Don't worry, I told you I'll be gentle"

Despite that however, it hurt like hell as he began digging into my soft clean bum. This is it, I thought, I'm finally going to feel the meat of a man inside me. I've been preparing for this for a long time, and secretly been craving it. I hoped it would be as enjoyable as when I practised.

I don't know if he was ever allowed to shave or even bath during solitary confinement, but I don't think so. He was so bushy down there and his bush brushed all over my bum as he tried to get in. A bit frustrated by my delicate and small bum, he held me firmer, and stroked my dick to distract me from the pain, until he finally pressed in.

This was it, he entered me. The lips of my bum were breached! He let out a loud moan as his long dick pushed into me. I was no longer a virgin in my bum! At first I whimpered and tried to make it as less painful as possible, but it pained a lot.

"Trust me. Relaxed your body and you'll be fine", Jake assured me.

I complied, and true enough, it began to feel better as my body relaxed. Realising that I was enjoying it, he began to thrust rough and hard, moaning and grunting like a beast, taking short breaks to make sure he lasted longer.

This big hairy man sweated profusely on me. His oily dirty body rubbed against my back as he ravaged me. He bathed me in his sweat, until I began to smell like him. After that I began to enjoy his smell. I enjoyed it all! In the heat of the moment, at the heightened excitement of his thrusts, I felt like losing my identity, like I was becoming no more than an extension of his beastly body. His gruff beard rubbed my shoulder as he kissed my neck and under my jaw, a pleasure I was grateful for. He tried stroking my dick but I was so focused on enjoying him in me that I didn't get hard. There'll only be one hard man in this bed tonight.

His thrusts then got firmer and he roared louder. He ravaged me hard and fast until he let out a great roar that must've echoed throughout the prison, blocking out my moans. With that I felt my bum filling up with his load. My eyes rolled back in a drunken state as his juices filled me. This is it I thought. It's over, I've been loved by a man. I've been breached. This was my first time with a man. He took my bum's virginity. After he exploded in me, he rested for about a minute, kissing my neck. I wish he'd stay longer but he then got out and went up to his bed above to sleep.

I laid in pain thereafter. None of my dildos were as big as his dick, yet none felt as good as his dick either. When morning came, I awoke to the sight of this beast grooming himself. I lifted my sheets. They had blood spots on them, like that of a bride on her first night, virginity broken.