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She's blackmailed after being caught on web cam.

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

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