My First Year in Prison

Tyler is happily engaged when his life takes a turn. After a couple bad decisions, he ends up in California State's Prison. Surrounded by bad boys, hot guards, and a lot of testosterones, is Tyler going to manage to keep himself out of troubles? (Erotic Drama - sequel to My First Year in College).

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My First Year in Prison

Chapter 15: Early release

"How does it work, if I want to see him?"

"What do you mean?"

"You know, generally, Falcon just comes get us whenever the warden has decided that he wants to, hum... see, one of us. But what if I wanted to, like, request a meeting or something?"

Ralph smiled, finally understanding where I was painfully getting at. We were alone in our cell; he was lifting a prison-made weight with several bottles of water scotched to his forearms.

I was still not accustomed to his huge body when it was fully flexed during exercise, his veins seemed about to burst, his biceps could have exploded, his sweat was heavily dripping on his (well filled) white boxer briefs. He stopped lifting for a few seconds and asked me to unwrap the weights. Of course, I was happy to help!

"I see. You want to be fully prepared for your hearing, eh?" He winked at me. "Sure, Deen can help you with the early release... well, if you get him some release!"

He was very proud of his pun. I was less enthusiastic.

Ralph was only saying the truth though. I wanted to convince the warden to draft me the perfect recommendation letter so I could obtain a reduction of my sentence. Hearing my pathetic plan said out loud made me cringe.

"I mean... That's why you were... accepting to see him. Right?"

"Right. And I'll be out of here earlier than you at this point. You have to know how to make him happy."

"So, what should I do?"

"Sexually, you mean?" He asked as I was removing the last bit of tape from his arm. "I thought gay sex was more your department than mine."

"No, I think I can handle this part on my own." I replied; our exchange was playful. "How can I make sure to see him before my hearing? It's in two days."

"Just go to Falcon so he can forward the message to Deen. He's not stupid, he's probably expecting you already."

"That's what I thought..."

I was about to go back to my bed when Ralph held my arm.

"Wait, Ty. I was wondering, do you enjoy going there?"

"I don't follow."

"In the warden's office, servicing him. Do you enjoy it?"

I was taken aback. I had never really asked myself this question.

"Why are you asking me that? Why do you care?"

"Just curious, that's all. If getting out of here earlier meant that I should have sex with a super-hot woman, I'd certainly be happier to comply with the orders! Since Deen is not an ugly lad, I thought, maybe, it was actually enjoyable for you."

"It did not seem that difficult for you either." I snapped back, remembering how well Ralph was taking the warden's cock far up his ass.

For some reason, I was upset. Ralph just shrugged his shoulders, unbothered.

"I'm very professional whenever I'm working on a job. That's what I've always told my girls. Act as if getting fucked by this old perv is the best thing that ever happened to you and maybe you'll end up believing it."

"Will you go back to it, when you'll be out of here, taking care of these girls?"

What a strange way to ask him if he intended to remain a pimp.

"Not sure... Maybe I'll do something different. Maybe I'll propose my own services, this will be far easier to manage."

"You... You would have sex with... I mean, you think women would pay to...?"

He chuckled.

"No need to beat around the bush, Ty. Obviously, I'm talking about men. I guess there are some old folks who'd be willing to spend good money to have me."

"No doubt!" I exclaimed, maybe a bit too excited. I was way more into the conversation suddenly.

He just smiled.

"I'll see. Before getting here, I never thought of men as potential whores you know. It's an adjustment. But you have not answered my question. Do you like it? Going to the warden?"

I rolled my eyes.

"I don't know how to answer this. I guess it's not that bad."

"I thought so. I mean, good for you man, you're getting some good fun and you can probably get out of here faster at the same time."

"Yeah..." I sat on my bed, thinking. "He's really an asshole, isn't he?"

"Who? Deen?"

"Yeah. Using his power and authority like that."

"He is. But don't waste your time and energy trying to fight the good fight my friend, just use the system at your advantage, and get away from his hell. As soon as possible"

He patted my shoulders.

Xander and Fernando came in at that moment and we changed the subject to the approaching wedding. Xander was one of the rare inmates who had barely any issue with the other convicts so his wedding with Mindy was a cause to celebration for pretty much everyone. For the occasion, the prison would exceptionally order some cakes from a local bakery. A good way to let everyone breathe and connect a little, despite the ongoing tensions.

I went to see Falcon later on that day and he was very happy that I had come to him, too content that I was the one in demand.

"Everyone has his own drug, I presume." He commented, and grabbing his bulge, he added: "Must be hard not getting any when you're stuck in here."

If only he knew that I was getting more than my fair share!

After our first encounter with Will and for the past week, I was regularly seeing him. In total, we had sex three more times, each time it was in the toilet stall near the gym's space. Very romantic, I know. As I had seen so many other inmates doing it before us, we locked ourselves in a small stall at the centre and he fucked my ass. Good. The position was not the most comfortable but we managed.

To be honest, it had become the highlights of my days.

I was not developing feelings for Will, I did not think so anyway, but having this forbidden pleasure, it had become something to look forward to. It was a nice distraction from my break up or the depressing life in prison.

Will had woken up something in me that I could no longer put down.

It was like a game, finding the perfect time to isolate ourselves, giving each other signs that we were ready, doing more and more daring things every time. Except this was not a game and the stakes were very real. As we were now virtually belonging to two different gangs, nobody could know about us. We were basically recreating a very fucked up, and I must admit somewhat pathetic, version of Romeo and Juliet.

Daddy Ray was not a fan of Will because he was too close to Romano and his crew. One afternoon as we were doing the laundry, he warned me:

"We need to be careful of them. I saw Romano and Bianchi approaching Trevor, Torres was there too. I heard they found a new way to get the stash into the prison. No way I'll let my son get into this stuff. Not on my watch."

I had already seen several guys becoming addicts inside those walls. Of course, they have proposed some stuff to me too. The first pills were always free but the more you were hooked, the more the prices were getting high.

Most of the gay sex happening in prison were caused by the needs of a meth head to get his fix.

I was looking at Will a bit differently. How well did he know Romano exactly? What was he doing, spending all his time with him? His attitude in prison was much different than in real life, here, he looked so tough, almost dangerous. When it was just the two of us back in my L.A. apartment, he had a bad boy attitude for sure, but most of the times, he was worried, just like a concerned business man.

A few years had gone by since then, and it only seemed like Will had gone deeper into the traffics. I felt very unease about this side of him.

We were never talking about that though. Well, to be honest, we barely talked at all. When we could have a moment together, we only had a few minutes and it was all about sex. Kind of awkward to ask the top who is fucking you if he is actually smuggling drugs in prison...

Two days later, Falcon came to see me only a few hours before my formal hearing. I had come to the conclusion that the warden had not gotten the message or was not interested but no, I was finally called in. I was still on the fence about the whole plan but it was too late to back down now.

Falcon told me and the rest of my cell that the warden was working on his recommendation letter and needed to check a couple things with me. Ralph was there, he did not show any sign that he knew that anything was going on. He had really learned how to hide his cards well.

"Good luck, Ty. Don't get released too soon, right? I still need you there for the wedding!" Said Xander as I was going.

"Don't worry, I won't miss that for the world." I replied, following Falcon.

The hope was actually to get released in the following March instead of the following September, squashing 6 of my 16 months sentence. I would definitely still be in the prison for Xander's wedding on December 12th.

I passed by Kurtis' cell on my way to the warden's office. He was doing some push ups shirtless, his hot body glistening. Sometimes I wished that he was the one I was meeting in the bathroom instead of Will. Besides the sex fantasies, I missed talking with him. Daddy Ray was a good guy but my times with Kurtis in the laundry room felt different, like we were having real and deep connections.

Maybe I could try to fix things up with him, so we could at least train together, be friends again?

I did not have much time to ponder over this as I was arriving at the warden's office. Falcon had his usual satisfied smile on his face when he knocked at the door. He stayed behind as I walked in.

"Welcome, Braxton. Guard Falcon told me you wanted to see me before I submit my letter. Is that right?"

The warden was wearing one of his fancy suits with a very thin black tie. He always had the same black glasses and he had trimmed his beard a bit. He was sitting behind his office, nibbling on his pen.

"Yes, Sir. I wanted to make sure you had all the information you needed."

I replied, trying to remain casual.

"Tell me, then."

"What... What do you want to know?"

I asked, a bit taken aback. He was actually ready to type something on his computer and I could see that he had gotten my files out; I saw my name on top of one paper and a brown folder with my inmate number "328" on top of it.

"Do you have a support system for when you get out?" He asked in a neutral tone.

I was expecting to take off my clothes, were we really about to do this by the book?

"I... Yes. My older brother will help me out. My best friends as well, Austin and Janice, do you need their full names? My brother is Ryan Braxton, and my friends..."

He cut me off:

"What about your fiancé?"

"He's no longer my fiancé, Sir."

"Really? That's too bad."

He seemed almost genuine but I knew it was all an act. He was probably messing with me.

"That's ok. I... I still have people."

"Sure, sure... But do you have a place to stay then? You were sharing an apartment with your former fiancé, right?"

"Yes, we were. I guess I'll...."

"You guess?"

"I mean, I have not thought this through completely but I'll probably be staying with my brother."

"Across the country? Braxton, did it cross your mind that precisely, you needed to think this through and made sure you had a plan before submitting a request for early release?"

My stomach hurt, I felt stupid. What was I thinking? That I would just have to blow the warden's cock one more time and I would be all set? As I was going through potential options on the spot, I realized that Mallory and Ryan had already two toddlers at home and another baby was due for early January. Would I really impose myself at their place? Could they only welcome me?

"If this is too complicated to stay with my brother, I know that I can stay with my friend Janice until I find a place on my own. I think a change of setting would be good for me anyway." I replied awkwardly.

"Hmmm... And what about work? What's your plan?"

"Well, I had my practice but now..."

"I am fully aware that you are no longer authorized to work in your field. That's quite a deep stain on a resume actually, it will surely set you back for other opportunities. What do you intend to do?"

Again, I felt so dumb not having think about this stuff! What the hell was wrong with me? Maybe if I were spending less time getting fucked by Will in the toilet's stall and more time working towards my future, I would be better off! Out of this prison, I had no job, no fiancé, no place to stay... I even questioned why I was in such hurry to leave this place.

"I... I have leads." I lied, clearly blushing.

"Can you give me some more than that? Your recommendation is pretty empty for now."

"I'd like to write."

I had had this idea in my mind for years but it was the first time I expressed it out loud and to myself clearly. The warden chuckled. I could not blame him. This sounded so stupid.

"To write?" He asked sarcastically.

"Yes, write."

"Solid job that is... Author!"

"I know, there's no guarantee. But this is something I'd really like to focus on. I do intend to have a job to earn some money but when I have some free time, I'd love to write."

"About what?"

"I'm not sure. Maybe my college years."

The warden put his hands in his head. He had listened to a lot of bullshit in his years at the job but he had probably never heard that much crap...

"Who do you think in their right mind would care about your college years, Braxton? You really are giving me nothing, aren't you? What's next, you want to marry Prince Harry? He's already taken, you know!"

"I do not intend to marry any member of the royal family..." I mumbled.

He let go of a heavy sigh and repositioned his glasses on his nose.

"Maybe I should put you in the list with the other crazies to meet with a counsellor, helping you get a job? It will help your file if I could justify that you have taken actual steps towards a real job."

"Sure, then."

"You will commit to that?"

"Of course, what else is there to do in there? Please Sir... I... I really need this recommendation letter."

He typed a few words on his computer and stood up.

"Must be hard, being you."

"What do you mean, Sir?"

"Never struggling once in your life before and now finding yourself fighting to get a low paid job after prison."

"How can you be so sure that life was so easy on me?"

He busted out laughing. The next minute was tough:

"Please! You were born in the perfect middle-class family, up middle class I would even say, in a nice suburban neighbourhood. No drugs. No criminality. Your older brother is a surgeon who literally married another surgeon. You went to college with your parents' money, switching your major and moving across the country after your freshman year! You felt reckless and untouchable enough to fuck with your college professor. And you were right, you did not have to suffer any of the consequences! Then, following your big brother's steps, you became a doctor yourself, a therapist. But as soon as you started practicing medicine, you had sex with your patient... I beg you, tell me how difficult it was for you growing up white and privileged!"

It was worse than being punched in the face. I snapped.

"At least, I did not become a fucking perv who uses his power to rape inmates because he's so uncomfortable with who he truly is! How long before you finally come to terms with your sexuality, Deen?"

I could not believe I have said that to the warden, right as he had my fate in his hands! I regretted my outburst instantly. He was expressionless. I even took a few steps back, fearing he might jump on me over his desk.

"I... Sorry... That was..."

He did not look furious but his lack of reaction felt even worse. He moved from his desk and went to stand, right behind me. He grabbed my wrist from behind. Firmly but not too violently. I felt his breathing on my neck.

"Guilty." He whispered in a soft but terrifying voice.

"Sir?"

"You caught me. I'm a pervert. Guilty as charged. But I will not let everyone say that I'm a rapist."

"No, Sir... This is not what I meant... I'm sorry."

He tightened his hold on me.

"You were the one asking to see me, remember?"

"Yes, Sir. I was..."

"And you are the one who still wants to feel my dick deep in his ass, right?"

He got even closer until he was all up against me. I felt his hard dick against my ass crack. He was really horny. My outburst just got him even more into his dominant role. I should not have been surprised: from the very start, what he liked was to play with the limit, see how far he could push his power. Now, I had offered him a perfect opportunity to let him show how much hold he had on me despite what I was thinking of him.

The warden was rubbing himself against me like a dog.

"Braxton, why did you come in here today? Tell me the truth."

My mouth was dry, I was shaking. And I said it:

"Sir, I came here today in the hope that you would fuck me."

"Because you were craving my big alpha cock?"

He would not have that.

"No... I... I wanted you to draft me a good recommendation letter."

He pushed me against his desk, my upper body lying down in tons of paperwork and he slid down my trousers and boxer briefs in one go.

"Tell me the truth boy, you want my dick?"

"Sir... I...."

"You still want your letter, Braxton?"

"Yes, Sir."

I heard his fly opening. He had never fucked me in the ass before. He was about to. Could I have stopped him if I had tried? Maybe. The truth was, I needed something from him. I did not fight back.

"I hope your teasing was worth the wait, boy."

He murmured, licking my hear. A second later, he spat in my bare ass.

My face against the desk, I thought of what I had done in my life to get to this point. I thought of all of the times that I had acted impulsively or chose the easy way out. I realized that my dick was hard... Damn, my turn on with dominant guys! I would never change! I felt ashamed and horny at the same time.

In no time, he had his dick in my hole. His spit had been the sole preparation for his 7 inches thick dick and I felt like my ass was being torn out. This was insane. I had to bite my fist not to scream! He fucked me dry for maybe ten or fifteen minutes and I could not barely process what was happening. Why the fuck my dick was so hard?

He never got undressed. We never switched position. He just pounded me like that, against his desk, filthy talking to me as my atrocious pain slowly turned into moans of pleasure:

"You fucking white trash, that's what you are."

His balls tapped against my ass.

"Your fiancé could not wait until you got home to empty his balls in another hole. Jesus, he does not what he's missing right now."

I cried when he said that but his dick was hitting my prostate. I moaned louder.

"If I'm a perv, you're no better than me, fucking fag."

I was not better than him.

"You are obsessed with dicks."

Again, it was true.

"How do you like mine? Thick enough for you?"

Another deep thrust inside of me.

"I love it, Sir." I replied.

He spat on my face and fucked me some more.

"How bad do you want my cream in your hole?"

"So bad... Please."

I had been fucked roughly before, but never like that. Was I just doing a job? Paying my freedom with my body? Was I getting raped? Or was I enjoying this? Was it just a roleplay I was willingly taking part in? The worst part in this was my fear that I was actually ok with being treated that way. I could not be into that... Right?

I felt Deen shaking behind me and his jizz filling up my ass. It seemed like a lot. We were still in the same position.