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.
