Swindled in Prison

Standing at the changing room, looking at the prison uniform that I would be wearing for the next years. I was still wondering how everything could go so wrong in such a short amount of time. They told me that I only had five minutes to get changed before a guard would come over to haul my ass away.

There was a mirror on the room for some reason. I looked at my face for a moment, trying to remember what I looked like before this chapter of my life. Green eyes, long lashes. Blond hair parted to the right. My face was slightly tanner than the rest of my pale body. At six feet height, most of my muscles were on the bottom part of my body.

My girlfriend broke up with me for not being able to get a higher paid job than her after graduation. We were only dating for a year, but that still hurt as she made me feel like a less of a man. That was the reason why I was so desperate for a new job. I did get the job a few months later, but it seemed like Rina moved on.

My biggest stress reliever was running five miles every morning. That gave me toned leg muscles as a result. At nearly six feet height, running regularly gave me a pretty skinny upper body. I was still evenly toned, but not muscular at all.

I was an executive at the marketing department of a large conglomerate. The work I was doing was nothing glorious, but there was room for growth if I kept on working. And of course, the pay was good enough for me to stay put. I didn't know how the regional manager managed to cook the books to take away millions.

I came to know about the scheme only a week before we were arrested. I knew there would be trouble if it was found out. But I was just a new hire. Having been in the company for only two months, I didn't have the guts to go against my immediate seniors. Being desperate for a job, I just went along with whatever they were doing.

Then it happened! There was a raid. Seven people from the marketing department were arrested, with me being one of them. The next month was a blur for me. We had to go to court. I just looked around, dazed, trying to figure out how and why all of this was happening.

Of course we had good lawyers at hand. We were told that a confession would be necessary to reduce any repercussions for us. I was too naïve. They told me to sign the papers that included my confessions. All of my superiors had done the same. So I also signed the papers. I really thought these corporate workers would have my back. Why would they go behind my back?

I am just a fresh faced 23-year-old college graduate!

I was hit with the longest jail time. I would have to spend three years in a medium security prison. The regional manager, the man that made all the plans and actually got rich off the scheme, was put under house arrest for six months.

I had no way of knowing why anyone would believe that I was responsible for all this. But I was just powerless to protest. I had nowhere to turn to. I have an older brother that lives in another state. I only had a three-minute phone call to let him know that I would be in jail for the next years.

As I picked up my orange trousers, I noticed there wasn't any underwear. I could keep the underwear I was wearing, but I decided against it. As I stood naked, my normally five-inch dick was shrivelled up and seemed smaller than an inch. I had noticeable pubic hair, since hygiene and grooming was not my biggest priority for the previous month.

After putting on my orange attire, I opened the door and was greeted by two guards.

"Harry Sanford!" One of the guards addressed me.

"Where's he going?" The other guard asked

"Block C."

"Heh! Could be worse."

I had no idea how to decipher what they just said. I just stayed quiet and looked at one of the guards.

"Wow!" The guard I didn't look at said.

"Yep!" The man I was looking at nodded. "Let's go Sunny boy!"

I nodded and followed the man. He led me down a long corridor and we entered what I assumed was block C.

After walking for a while, the guard stopped in front of an empty cell at the very end of the block. It was a fairly clean room with two bunk beds that could accommodate four prisoners. The cell was nicer than I had expected it to be. There was a toilet at the back side with a basin.

"Your cell mate is probably out in the rec room." The guard informed me before commanding. "Follow me now!"

I followed the man to the dining area where a lot of people were just hanging around. A number of inmates eyed me up and down, making me quite uncomfortable. Then I was led to the rec room before going to the laundry area.

"The yard's closed. you'll get to see it tomorrow."

So far, despite feeling slightly nauseous about the fact that I'll be spending the next three years of my life in jail, my mind was already trying to convince me that it was doable and everything was going to be alright.

"Dinner's on in a couple of hours," The guard said. "You can hang around the rec room or go to your cell for now."

I decided to rest for a bit in the cell. As I was walking alone, another cellmate whistled to call my attention. I did stop, trying not to attract any unwanted attention on my first day in prison. It was a much taller black man that introduced himself as Amos. He grabbed me by my arms and was very slowly looking up and down my body. I introduced myself to him and said it was nice to meet him.

"Good lord you're submissive!" He said as he came closer. I could smell weed on his breath and briefly wondered how he was smoking marijuana inside the prison.

He then asked me which cell I was staying at. After answering him, he let go of my hand and bade me good luck before slowly walking away. As I was about to exit the dining area, another guy came closer to me and told me to just be nice to my cellmate and everything was going to be alright. Wondering what he meant by that, I kept walking to my cell.

This time, there was a man inside the cell working on something in the bottom bunk of the left side. As soon as I went inside, the man stood up and came up to greet me. I put out my right hand for a friendly handshake, but the man grabbed my hand tightly and pulled me in for a hug.

He was slightly shorter than me with a bulkier build. He was a dark haired middle aged man that did not look threatening like the other convicts.

"Oh you're back sweetie," The man started kissing my cheeks in between sentences. "Daddy missed you so much, I'm so happy that you're not mad at me anymore."

"I ... uh ... excuse mmmmmmm!" A forceful kiss to my lips stopped me from saying anything. Despite keeping my lips shut, this older man forced his tongue inside my lips.

"It's been so long honey, I thought you wouldn't want to waste any time." The man broke the forceful embrace and went back to the bed. "Come here now, I fixed everything, you just need to lay down and take it."

I felt like something was coming up my throat, but there was no vomit. I was horrified to find out that the man was actually holding onto some kind of douche filled with water.

"Come here now, don't be shy! You'll have to do this twice by yourself starting tomorrow."

I was frozen shut in place. I came to the cell to lie down and rest for a while. Not to get my asshole cleaned out.

"I really missed you honey." The man's expression changed a little. "But don't make daddy repeat himself."

The tone of his voice sent a shiver down my spine. I slowly walked over to the man and was thrown on my back onto the bottom bunk. He then pushed my legs upwards so that my legs were lodged against the top bunk. It was an awkward position for me to say the least. But at the swiftness at which my trousers were pulled down and exposed my nether region; something told me that I would be spending a lot of time in the same position.

"Sir, I don't ..."

I was stopped with a hard spank on my ass. "You don't call me sir young man. It's daddy, understand?"

'what the fuck?'

Without warning, the man started grinding his nose against my asshole.

"You smell so nice." Then he slowly rubbed his tongue against my opening. "Let's not get carried away now."

All I could see was my legs against the top bunk. I just closed my eyes and tried to imagine that it was not happening to me. But the cold sensation of the lube on my ass made me aware of the present. The slow insertion of the douche surprised me. It was not the weirdest feeling ever, but it was not something I was used to feeling. The worst was yet to come when lukewarm water was slowly injected in my insides. As the douche was empty, I felt full and needed to relieve myself right then and there.

Then older man instructed me to stay put for ten more minutes like that. Again, I closed my eyes and tried thinking that I was not really there. It didn't work that much. And when I opened my eyes, I saw the man in my peripheral vision. He was violently jerking off with a manic look in his eyes. I told myself that it would be better if he just jerked off instead of using my body.

I was proven oh so wrong really quickly. The man told me to get up and relieve myself on the toilet. As soon as I stood up, the man pulled my pants down completely. I was now only wearing the orange sweatshirt with an immense pressure on my ass.

The man helped me walk up to the toilet at the back of the cell and helped me sit down. I closed my eyes and relieved myself. As soon as I was finished, the man held me by the chin and had me look up at him. Despite being older, shorter and fatter than me, the man exuded undeniable strength and dominance that prevented me from acting out.

As we made eye contact, he started speaking to me.

"Sweetie, it's been so long, I'm sorry," He paused for a moment. The words out of his mouth sounded gentle enough. But the deranged look in his eyes made me was to run away as far as possible. But I was sitting on a toilet at the back of a cell that only we were going to be living in for a while. And this older man was all over me.

"But daddy missed you so much!" He kept talking, one hand stroking my chin, the other, caressing my hair. "It might feel like we're rushing things; but ... by tomorrow, it'll be just like the old times." The man let out a smile. A smile that made shivers run down my spine. "Do you get it?"

I stared at him dumbfounded, not knowing that the man expected an answer out of me.

He clenched his teeth and asked me again. "Do. You. Get. It. Sweetheart?"

I quickly nodded up and down, regretting the day I was born.

"Talk to me son. You know I don't like the silent treatment." His hand around my hair was slowly getting rigid as he said that.

To say my fight or flight instinct took over would be an understatement. I had been wanting to run the fuck away from here for a long time. But I suddenly realized what I would have to do to survive in this situation, with this deranged lunatic.

"I get it daddy ... I uh daddy," I looked him in the eyes trying to dig out the slightest bit of sympathy from the guy. But what it saw was a guy that knew what he wanted and was going to get it even if my teeth are in place or not.

"What is it sweetie?" He wanted me to keep talking. I had to keep going with the façade and walk into what the man had eventually planned for me.

"It's been so long daddy ... I don't even know what to say."

I knew I had chosen the right words as it responded with a soft kiss on my forehead and a low moan.

"I missed you too." I added, trying to please the man.

But that might have been a mistake as the immediate response was a growl and a forceful kiss on my lips. I didn't resist as much this time as he tasted the insides of my mouth vigorously.

"I know you missed our late night daddy-son bonding time haven't you?"

"Yes daddy of course. I missed you so much. But it has been so long."

I could not believe that I was playing into the sick fantasy of this man without even knowing his name. And he didn't even know my name!

"Oh I can't wait any longer." He let go of my chin and I was faced with the angry tip of a sizable penis. "You know what to do."

"Oh daddy! It's been so long; I don't know if I can do this."

"O I'll help you remember. You don't have to put it in your mouth right now." He grabbed me by the shoulders and pulled me. "Come over to the bed right now."

"Daddy please," I could not believe what I was saying. "Please let me suck your cock."

"There's plenty of time for you to worship me down there." He pushed me to the bottom bunk. Both of us completely naked right now, I felt like shrivelling up. "Daddy will let you chose the position."

Not only was I going to be raped, I was given the choice to choose how I was going to be taken. Tears started streaming out of my face. The man literally leaned over and licked the tears straight off my face.

"What's the magic position baby?"

"Doggy ... daddy!" I was defeated. I was defeated the moment I walked inside the cell. No, I was defeated the moment I trusted my bosses to look out for me. and right now, I was about to get fucked in the ass for it.

"Assume the position sweetie."

I went on all fours and the man brought something out from under the other bunk bed of the cell. I turned to see the he had a tube of some sort. I didn't know at the moment, but I should have been thanking my lucky stars that the man had lube handy with him.

The first thing he did with the lube was to apply it to my nipples and shrivelled up dick. With some gentle rubbing, the man had my dick hard in less than five minutes. As I started feeling pleasure in my flesh, the man inserted two finger inside my ass at once. Even with ample amount of lube, it as highly uncomfortable for me and I let out a little groan.

"You don't have to worry about the neighbours now. We are all alone. Don't be afraid to make a little noise."

He kept playing with my dick and balls whilst also fondling my nipples from time to time. I don't know how long it had been, but I was feeling like I was about to cum. The fingers from my ass were gone, making me feel a little empty for a small while. But my ass was soon filled with something much larger.

And I did make a lot of noise when he slowly but surely planted his entire length of dick inside my canal.

"Tell daddy how you like it." The man commanded.

"It hurts daddy! You're too big." I cried out.

"You'll open up soon enough. Stop complaining."

I knew what he meant by that. And he was right. His slow strokes felt less and less painful as time went on. And soon enough, the man shot his load deep inside of me. I felt the tip of his dick pulsating deep inside. And by instinct, I knew that he would be pulling out soon.

But I was wrong. We stayed in that position until the dick inside me went completely flaccid and slowly plopped out of me. He took the name of the position a little too seriously.

When I sat down on the bed afterwards, I felt the sensation of a burning pain inside my anus. The older man saw my discomfort and told me that it would go away pretty soon. And he was going to help me with it.

--

Both of us got dressed up in our jumpsuits for dinner. As we got out of the cell, daddy told me to keep one of my hands inside his back pockets to let everyone else know that I was not to be messed with. He told me that there are pretty bad people out in the world that he was going to protect me from. I wished there was somebody to protect me from him.

During that time, I learned that the man's name was Kenny. Someone asked him about me. He told others that I was his baby boy and I was not to be messed with. During dinner, Kenny fed me small portions and wiped my face from time to time. I looked around and saw that nobody reacted to what was going on with me. So I guessed that things like this was regularly happening inside the prison.

--

After dinner, Kenny led me straight to the cell. And the first night of the rest of my life began.

Kenny undressed the both of us and had me sit on the floor. He then sat on the bed and told me to get to work. I had asked to suck his dick before so that he would now fuck me. Now he wanted me to take my time and slowly worship his cock. And I had no other choice. So I went to work. I just did what I thought would please me the most.

I started by kissing the tip of his dick and slowly licking the entirety of his member. After lathering enough saliva all over his cock and balls, I let my hands go to work. I kept my mouth only on the tip and started vigorously stroking his cock.

He did not last long and came inside my mouth. Despite feeling like puking it all out, I forced myself to drink all of his cum right away.

"Ooh, you have been a hungry boy haven't you?"

After gagging for a little while, I replied, "Yes daddy. Your boy has been so hungry for you!"

"Such a good boy." He had me stand up and sit on his lap. "And good boys get rewards." He then started slowly stroking my cock.

"Your cum in my mouth was enough of a reward for me daddy." I wanted all this to be over. I just needed sleep.

"You have been so nice to daddy; I just know you need a release." He spat on his hands and started giving me a hand job. It took me painfully long to even get erect for the man in front of me. there was enough friction for my dick to get pleasure, but in front of me was a middle aged fat man with hairy chest furiously stroking his hands.

It wasn't until he started rubbing all over my torso with his slimy hand when I slowly, even disgusted with myself, started getting hard. The dirty talking started as soon as I was hard. Kenny kept calling me a whole range of cute and degrading nicknames. But the one constant thing in his talks was that how much he had missed me.

It was a painfully long time before I ejaculated all over Kenny's belly. And by that time, I could feel his hardening dick slowly knocking against my ass cheeks. I knew I had to beg this man to let me rest but I didn't want to anger him. I thought for a long time before choosing my next words.

Then I leaned forward, touched my sweaty forehead against his, and said, "I am so tired daddy; can we please cuddle and go to sleep? Please daddy please?"

His dick was hardening before. But after what I said, it was throbbing against my ass. I just sighed in response.

My torso was on the bed and my legs were hanging from the bunk as I was laying on my belly. Kenny did not waste a minute before plowing my ass. I was groaning and crying as he kept fucking me a lot longer than before. I was pretty sure everyone in the cell block had heard me becoming the bitch of this deranged old man.

I did not have any energy left when he was done with me. Kenny picked me up and granted my wish of cuddling with him to sleep.

Both of us reeked of sex and we were sweat slicked to the point of dehydration. But at that moment, I could not think too much as I was way too exhausted and slowly drifted off to sleep.

---

That night I dreamt of going back to my grandparent's barn and chilling out with my girlfriend Rina. I think in that dream, we were married and moved out to the countryside. I remember feeling a strange sense of elation in my dream.

I was sitting on the front porch with my wife and we were enjoying a drink together. Then I heard something falling off in the tool shed and walked over to investigate.

To my horror, there was a faceless man standing inside. I ran out of the door but ended up in the tool shed again. There was no escape as the faceless man was in front of me and my wife in the sunny weather had vanished.

The faceless man started walking towards me. He was much taller than me. My heart rate went through the roof. But knowing that there was simply no escape; I knew what I had to do. I bent over and pulled my pants down.

There was a demonic laughter that filled the entire room before my ass was penetrated by the faceless monster. I screamed out in pain and woke up from my dream.