Back where I come from a misdemeanor can get you to jail if it's repeated for three times in a row. I was stupid enough to commit the same petty offence three times and I had to stay three months in prison. Those were the worst three months of my whole life...
In the beginning I could not believe I had been imprisoned. What was I doing with all these criminals around me? I didn't deserve this at all but the thought that it was just for three months would ease the pain. After a week or so I got used to the daily routine. A shower in the morning, a terrible lunch, walks in the prison yard along with the other inmates and an uneasy sleep at night.
On my seventh day in prison the guards informed me that the warden wanted to see me but they did not know what it was about. They took me to his office and left me there alone with that 50-year old guy.
'So you're Mr. Jeff R.,' he said.
'I've been watching you for a couple of days now and I have a deal for you. But first let's watch this video I prepared for our meeting.'
I could not believe my eyes. It was a video of myself in the shower. There must have been a small camera on top of the shower, which had been recording all of us. There was nothing I could hide. I just stood there with the warden watching myself on the TV screen with all my private parts exposed.
'I've noticed you since you came here, Jeff! You have a nice, round, hairless ass that every man would like to get his hands on!'
'How dare you talk to me like that? I'm a prisoner, not some whore you picked up from the streets!'
'Well, that can be taken care of!'
'What do you mean?'
'As I told you before, I'm willing to make a deal with you. I will make you my bitch for the rest of your stay here. We will meet and fuck once a week and I will take good care of you. You'll have good food, fresh clothes and clean sheets everyday. But most of all, I'll protect you from the rest of the prisoners. The guards will be constantly on your side and nobody will ever try to hurt you. It's either this or becoming the whole prison's bitch!'
'I' don't believe I'm hearing these things. What kind of a person do you think I am?'
'Think about it, son. You can be my bitch once a week or be raped every day by a different inmate. It's as simple as that. Just think about it and tell me what you have decided.'
'Why should I listen to you? I've been here seven days and nobody has dared to lay a hand on me. Why would they bother me now?'
'Well, we'll just have to wait and see what happens, won't we?'
I didn't like the sound of that. The warden told me that I had a couple of days to think about it and then I would have to give him my final answer.
I returned to my cell and fell asleep. I woke up after a couple of hours and saw my cellmate, Derek, jerking off. But, this time, there was a different look in his eyes. I had watched him masturbate a few times before but nothing happened. He would cum silently and fall asleep. Now he was moaning loudly and he was looking at me.
'Look at my cock, Jeff! Wouldn't you like to feel it in your asshole? Come here, grab my dick, we can have a lot of fun the both of us, you'll see!' he said.
I was terrified. I screamed for help and the guards came to my rescue. They told Derek to behave himself, otherwise they would notify the warden and he would be transferred to isolation. Derek's 'attack' was a surprise for me. Why would he do that after having me in his cell for a whole week? I couldn't find the answer to that question, so I tried to get some sleep.
I woke up the next day and it was time for the morning shower. I took off my clothes and I wrapped a towel around my waist. I got into the shower and I started bathing. I knew that the warden must have been watching me but I didn't care. I had to clean myself up. While I was pouring shampoo on my hair, I felt a hand groping my butt. I froze. I couldn't see who it was so I just shouted trying to scare him off.
'Get the fuck out of here! Leave me alone!'
Whoever it was took off right away. I finished my shower as fast as I could, grabbed my towel and notified the guard that I was ready to return to my cell. While I was waiting for an escort back to my cell, I felt a hand squeezing my ass cheeks very hard and whispering to my ear:
'Your ass is mine! Wherever you go I'll be there to hunt you down and fuck your brains out!'
In a few seconds the stranger disappeared as the guard came to take me back to my cell. This was the final straw for me. First, it had been my cellmate, then, the guy in the shower and now, this guy who threatened to hunt me down and fuck me. Either the warden was right or all these guys were working for him and were trying to scare me and make me take the deal he had offered. In any case, I thought that my life was in danger and that if the warden couldn't have me he would make sure I deeply regretted not accepting his offer. There was only one thing I could do. I would accept his deal and he would fuck me 11 times before I got released. It seemed to me that this was much better than being raped each and every day and catching any STD's from the rest of the prisoners.
I called the guard and told him that I wanted to meet the warden. He took me to his office right away and left us alone.
'I knew you'd make the right choice, Jeff!' the warden said grinning. 'Don't worry I'll take good care of you and your virgin ass...'
'Thank you, sir!' I said feeling some kind of relief.
'Let's not waist any more time! Sit on the couch, I wanna show you something.'
The warden took off his shirt and his pants and stood in front of me wearing nothing but his underwear. His crouch was a few inches away from my mouth. The warden pulled down his last covering revealing a big, semi-hard, thick cock.
'That's the cock that's going to make a man out of you, son! Take a long good look at it. Soon, you'll be begging me to fuck you with it.'
The size of his rod was horrifying. I couldn't begin to imagine how much it would hurt to be fucked in the ass by that old monster.
'Don't be shy! Take it in your mouth and start sucking it, real slow,' he urged me.
I obeyed taking his dick in my mouth. It was wet with pre-cum and hot. I placed my tongue on his red cockhead and started licking it with slow, circular movements. Meanwhile, I was rubbing his balls with my right hand making him even hornier. But that wasn't enough for him. He was into rough sex and he was soon going to prove that to me.
'I told you to suck my shaft not to lick it like a lollipop! I'll teach you how it's done, bitch!'
The warden grabbed both sides of my head and pushed it forward making me gag with his monstrous tool. Then he started pushing back and forth. I was giving him great head and he was enjoying it...
'Yeah, suck that cock, bitch! Show me what a good cocksucker you really are!' he yelled.
As his rod came in and out of my mouth, his balls punched against my chin making me feel like a dirty manwhore. Meanwhile, his cock was still growing and I was wondering how large it was going to become. He pulled out, slapping my face with his hot rod and humiliating me even more.
'You're paying your debts to society, Jeff! When you get out of prison, you'll be the best cocksucking bitch of all time!' he said laughing.
Then he grabbed my hair and pulled my head towards his sack.
'I want you to suck my balls, now. Take each one in your mouth!'
As he grabbed his shaft and kept it straight up, I started licking his hairy balls, one by one as he had ordered me to. I made loud, slurping sounds trying to convince him that I was doing my best to suck his balls real hard.
'You're a good learner, Jeff. Now that you know how to suck, grab my dick and give me a nice blowjob!' he said grinning.
I got hold of the warden's pole and began deepthroating it. I could tell from his moaning that I was doing a much better job than before. While I was sucking the full length of his manhood, I was touching his balls with my free hand and that was driving him crazy. His iron-hard rod came in and out of my mouth several times and each time he pulled out I sucked his cockhead real hard as if trying to squeeze out all the cum in his balls. The warden had enough of my cocksucking and he was now ready for the real McCoy.
'Now that you've tasted your first cock, it's time to take the first one in your back door!'
I was scared. Sucking his shaft was one thing but taking the full length of his monster in my virgin anus was another. However, now it was too late to quit.
'Take off your uniform, lie face down on my desk and spread your legs, Jeff!'
I took off the orange prisoner uniform and assumed the position he told me to. My chin rested on the cold desk and my ass protruded covered only by my white boxers. The warden approached me and took a pair of scissors from the left drawer of his desk. I couldn't even imagine what was that for...
'Relax, boy! I'm just going to play with you for a while. I won't hurt you. You can bet your ass on that!' he said smiling.
As I was bending over he used the scissors to cut my boxers in two. The thin fabric collapsed and fell at my feet revealing my round, untouched ass. The warden stared in awe.
'That's one of the finest pieces of ass I've ever seen and, believe me, I've fucked a lot of guys in this office.'
The warden started groping my butt and squeezing it. He was really excited.
'Spread your butt with both hands, I wanna see your rosebud before I rip it!'
There I was: Bending over, holding my ass cheeks with both hands and showing off my asshole. I couldn't believe I was waiting for another man to fuck me...He spat on his hand and smeared his saliva on his cockhead. That was all the lube I would get.
'Aren't you going to use some lubricant? You promised not to hurt me!' I complained.
'Remember that you are in prison. Besides, you don't need any more lube; my rod is already wet from your blowjob and if I spread more lube on your butthole you won't feel anything...'
I thought that this sounded rational. A strange rush had taken over me. Now that I knew I was going to get fucked from behind I wanted to feel the experience in it's full. The warden's cock touched my asshole. I felt his hot cockhead at the entrance of my crack. With one powerful movement, he shoved the head of his rod in my unprotected rectum. The pain was excruciating. He should have used some lube on me. I thought that there was still time to stop this; after all, he wasn't completely inside me yet.
'You're hurting me! Get out!' I screamed.
'Patience, my boy, you're still in the beginning. Wait till you get used to it,' he said.
'I don't want to! The deal is off! I don't care about anything! Let me go!' I shouted.
'Shut up, bitch! I'm gonna fuck you whether you like it or not! I'm in charge here!' he yelled.
I tried to escape his grip but the warden pinned me down onto the desk and started giving me powerful strokes. It was futile to resist. When he became sure I wasn't going to get away, he resumed his upright position and started fucking me again.
I tried to plead with him to release me...
'Please, let me go! I will suck your cock whenever you like but, please, stop fucking my butt!' I begged him.
'Shut up and take it like a man! I'm gonna teach you a lesson you'll never forget, cumslut!' he said.
After each stroke he would spank my ass real hard. His tool was piercing the utter depths of my rectum. The spanking made my ass completely numb. I could still feel his rock-hard dick hammering my anus but it hurt less than before. The warden was ecstatic. He kept pumping my -until then- virgin asshole, swearing at me and humiliating me.
'Yeah! That's more like it, bitch! There's nothing like a tight, round, hairless ass like yours, Jeff. I knew you'd be a good fuck! Now, spread your butt for me, take it deeper in that sweet hole of yours!' he moaned.
His throbbing cock punctured my ripped butt until he had enough of that position.
'Turn around, boy! I want you to look at me while I make you my cockslave!' he said.
I was now lying on my back. The warden placed my feet on his shoulders and pushed his rod back inside me. Indeed, I could now watch him deflowering my firm butt. The sight of his manhood entering my most private part, made my own cock stand at attention. It was a natural reaction; I couldn't stop it. He noticed it right away.
'I see you like what's going on! You like having a big, fat cock up your ass!' he said.
His strokes became even harder and his pubic hair touched my balls. I became so horny I couldn't control myself. My dick exploded spurting several blasts of hot cum on my stomach.
'Ohhhhh!' I moaned.
'Yeah! Cum, bitch! A cock in your ass is all you need, eh? Wait till you taste my own cum!' he said.
I had lost track of time. How long had he been fucking me? He didn't seem to care. Now, he wanted to fuck me doggy-style...
'Get off the desk and drop on the floor on all fours!' he ordered.
It was time for round three. He assumed his position at my back door and resumed pounding my anal ring. He had grabbed my ass with both hands and he was giving me his most powerful strokes.
'Take it in your ass, bitch!' he grunted.
My asshole had become more flexible and I could endure his thrusts easier than before. My dick had softened and my whole attention was concentrated on my butt. I had never fantasized about taking it from behind before and now I was getting the real thing. Sure, the warden was a bit rough but it was an unprecedented experience. It hurt quite a bit but after a while you get used to this sensation and you start enjoying it. The warden had noticed that. Without even realizing it I was moving my ass backwards trying to take his shaft even deeper inside me...
'Shake your ass, bitch! Fuck that cock in your butt! I know you like it!' he yelled.
Deep inside me I wanted to tell him to fuck me harder and to go deeper and faster but I didn't do it. I didn't want him to know his was right even if my ass gave me away. His throbbing tool continued spearing my tight hole. His thrusts had become faster, his breath was heavy and his balls were slapping against my cheeks. I could hear the sound of his sack beating against my abused ass. He was going to reach his climax. The warden gave me a few more thrusts and then he came splashing my anal walls with his hot, sticky male fluid.
'Yeah! Take it, cumbucket! Take my hot cum in your tight asshole!' he screamed.
He kept ejaculating for several seconds until his cock stopped spasming. He collapsed on top of me with his dick still inside my hole. My violation had been completed. I lied on the floor, cumsoaked, with another man's cock inside my ass.
The warden finally got back on his feet and gave me permission to get dressed and leave. He fucked me another 10 times and he kept his part of the deal. When I got released from prison I didn't tell anyone about my anal adventures. It is a secret I'm going to keep for the rest of my life...