A gay story: 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.
—
Kenny started fucking my ass in my sleep. I screamed out and told him to stop.
“What did you say?”
“Please stop daddy!”
“Mommy’s not coming to stop this now baby. You and I have all the time in the world.”
“It hurts daddy!”
He gave me one dep thrust in response. Making me cry out in response.
“The more we do this,” He pulled his dick out with only the tip inside now. “The faster,” He pushed it all in again. “It’ll stop hurting. Then we can go back to enjoying each other’s bodies like before.”
He then kept fucking me at a fast pace for five more minutes before injecting another dose of semen deep inside of me.
My tears didn’t dry this time before slumber took me away. A small part of me wished I never woke up from this.
—
That time I dreamt of being chased by the faceless monster through an endless maze. No matter how fast or how long I was running, the thing was right behind me. I could hear its laughter as I was slowly losing hope.
—
As expected, I woke up restless the next morning.
The good news was that Kenny was not awake. The bad news was that he still had me in a bear hug. My body slowly moved to the rhythm of Kenny’s breathing. I tried to slowly squirm away to get up from the bed. But Kenny quickly grabbed my left pec, and squeezed it like a boob.
He was spooning me from behind, so I slowly tried to see if he was awake or not. To my surprise, he had grabbed me tightly in his sleep. Another slow squirm from me had an arousing effect on his dick. That made me freeze up and completely stop moving.
But I was just trying to delay the inevitable.
Less than five minutes later, Kenny kissed me on my shoulder and said that he was never going to let me go.
I was fucked in that exact position with just spit working as lube. I couldn’t even cry at that time. I wanted to.
But as I was getting used to the pain of forced entry. I felt a strange sensation deep inside me that I never knew existed.
It was a form of pleasure that left me confused.
—
I was able to take a shit without interference that morning. It was still a highly uncomfortable experience to do it with another man in the cell.
Kenny fed me during breakfast again. It was another way of keeping me submissive without anything sexual. I tried looking around to see if anyone else was being spoon-fed or not. What I found was a few examples of obvious hand jobs going on under some tables.
After breakfast, as Kenny started leading me to the yard, a guard approached us. The guard told me to follow him and informed Kenny that I would be on laundry duty.
Kenny just told the guard to keep his hands off me before letting me go.
—
Some of the inmates were given various jobs around the prison. I walked with the guard who showed me where I would be spending most of my day time in the prison.
There was no meet and greet. One of the inmates told me to start folding the laundry that was done. I didn’t even ask anything else and went to work. It was certainly better than walking around with Kenny and wondering when he would ask me to pleasure him sexually.
The work was mind numbing, but it certainly helped me pass the time.
And the time passed pretty quickly.
I was told to go take a shower. And my dread was back as I anticipated the worst as I kept walking to the designated area. Believe it or not, I thought for a moment that having Kenny with me while I walked there would make me feel safer.
But he was nowhere to be seen. I quickly realized that I was going to have to get naked and shower alone in front of who knows how many other inmates.
As soon as I got under the running water, someone squeezed my bare ass. I nearly slipped and fell before someone else grabbed me by the shoulders. The word soon spread around that I was with Kenny. No one else bothered me as I showered.
I felt a strange sense of relief for a moment. But as I was getting dressed, I wondered what kind of man Kenny was that everyone else completely stayed away from me. I wondered if I was really in some kind of danger while I was with Kenny.
I thought I was in a medium security prison where truly dangerous criminals were not going to be put in. But I didn’t get a lot of time to think about it as I saw Kenny approaching me as soon as I got out of the showers.
“You shower already?” He asked.
“Yes … daddy!” I answered nervously.
“It’s alright for today.” He let out a chuckle. “But don’t shower without daddy from now on okay? There are mean people all around here.”
“All of them left me alone after they learned who my daddy was!” I said, trying to impress the pervert.
“That’s good.” He spanked me as he led me for lunch. “But we’ll shower together from now on.” Then he put one hand under my pants and pushed his middle finger inside my ass. There were a lot of people around us and everyone clearly saw what was happening. “We’ll wash each other together, okay?” He asked, one finger knuckles deep inside of me.
“Y … yes daddy!”
“Let’s have lunch for now. We’ll see what we can do later.”
I didn’t think too much of it and we headed to lunch. It was uneventful and Kenny led me to the open yard where people were playing different sports or working out. Kenny led me to a bench and had me sit on his lap for a few minutes.
A small group of men approached us and asked Kenny if I could be loaned out for some time. Kenny kissed me on the neck and told all of them that I was his little boy and I was off limits. I could feel the hardening outline of his dick on my ass. Kenny caressed my inner thighs out in the open for a while before telling me we would be going to our cell right then and there.
My heart rate went through the roof in anticipation of the coming events. Deep down I knew I had to get used to this fate of mine. But getting pummelled in the ass by a sizable dick every day takes a while to get used to. Especially if you used to be as straight as an arrow only a day ago.
I was right to expect that we would be naked as soon as we went to our cell. But I was wrong to expect a dick in my ass straight away. After getting naked, Kenny started caressing my body all over. I felt a strange mix of discomfort and arousal at the time. my half hard dick made me feel ashamed as I looked down to see Kenny was fully hard.
He then softly touched the tip of my cock with his thumb and index finger. I let out a deep sigh, realizing how quickly my body was changing and getting used to the touch of a man almost old enough to be my father.
“You smell so nice baby.” Kenny said after taking a deep breath. “So clean and shiny.” He tweaked my nipples, making me yelp out. “But daddy didn’t get to shower today. I feel all dirty and smelly baby.”
Not knowing what was expected of me, I just pouted in response.
“I want you to help me clean me out.” He looked through me. “Won’t you help your daddy get clean?”
“Of course daddy!” I looked around. “But I don’t think we’ll have enough water in here. Maybe we can go to the shower,”
“The shower is closed after 2.” Kenny cut me off. He put his right thumb on my lips and pushed it inside. Making me suck on his thumb. “Besides, we have everything we have to get clean … Right here!” He pulled my lower lip down, opening my mouth wide. A few drops of drool came down from my tongue.
“You’re already salivating at the thought of it, aren’t you?” He had the predatory look in his eyes again. That was the look that made me submit to the man in an instant.
“Yes daddy! Just tell me what you want from your boy.” I was still having a hard time figuring out what was expected of me. The naked body of the older man did not clue me in as I only noticed the hard dick and thought that he wanted me to suck it.
But Kenny lifted his right arm up and exposed his really hairy armpit. “Get to work. Put that tongue to good use.”
I was frozen at the command and took a step forward. The acrid smell was something I never wanted to get close to.
“Don’t make me repeat myself boy!” Kenny commanded.
I looked him in the eyes, shook my head and dove nose first into the hairy armpit. It was hard for me to not vomit out everything Kenny fed me through the day. He squeezed my ass and told me to take a good whiff before licking him up.
I closed my eyes, gagged a little, and obeyed him. There was no other way around it. I was now licking a hairy armpit of a middle aged man. Kenny let out a low moan and pulled me away. He held my head with both hands and sniffed my mouth.
Then he assaulted my face with his tongue, licking it all over. A minute later I was shoved into his left armpit. After painfully scraping all around the pit, my tongue felt dry as shit and I wanted to wash my own mouth out with soap.
Kenny probably understood how dry my tongue was feeling because he dove his tongue inside my mouth. It did help with the dryness, but my mouth was now wet with Kenny’s saliva.
As he let go of me, I felt like the nightmarish ordeal was over. Kenny sat down on the bottom bunk and told me to get on my knees in front of him. I was mentally ready to take his dick in my mouth.
Right at that moment I heard someone else talk to Kenny from outside.
“This was too easy, wasn’t it?” The man from outside spoke up.
“Dude, just let me and my boy alone.” Kenny hurriedly said. “We have a lot of catching up to do.”
The humiliation of being completely naked on my knees in front of another man didn’t even hit me as hard. I knew this was just the way my life was going to be for at least one year. Then if my parole hearing is denied, it would be three years. And by the way things were accelerating, I thought that this new lifestyle might just stick with me for a little more than three years. And it was only my second day in the jail!
As soon as the man walked away, I focused on the dick in front of me. But Kenny stopped me right away.
“Ooh, eager little boy. We’re not doing that just right now.”
I looked up at him, doe eyed, trying my best to look innocent. Kenny lifted his leg up in front of me and told me to start licking the bottom of his feet. I choked at the thought of it. He was wearing shoes all day, so there was no visible dirt on his feet. But the slight yellowy feet smelled worse than his armpits.
“But daddy, it’s really dirty.”
“That’s the point of showering isn’t it?” Kenny urged me on. “You’ll clean me all over my body.”
With a sinking heart and a stinking nose, I started licking the bottom of his feet. Kenny then instructed me to suck on each of his toes like a penis. I did as I was told. Every chance I got to look up, I saw an untouched throbbing cock, pulsating, waiting for release. Kenny was breathing heavily, basking in the broken boy that was me, pleasuring him in any way demanded.
When I made eye contact with my cell mate, it seemed like he was high on drugs, with a fixated look on my face. After slowly sucking each of his toes, Kenny didn’t have to instruct me on anything and I started kissing and licking his right feet. I had lost track of time. As I worked my way up to his right knee, I don’t know what came over me as I blew him a kiss.
Then I switched legs and started didn’t stop until I made it to his thighs. Then I switched legs again and started working on his thighs. As I alternated between his inner thighs, Kenny let out loud moans. I wanted to get back and see what he was doing, but he quickly grabbed me by the head and held me in place.
He had leaned forward from the bed a bit. All I could see was the inner thighs and a slight glimpse of his hairy asshole. Asshole that was slightly winking at me. It took me a while to realize that Kenny was cumming all over my hair. I closed my eyes and just stay put.
A couple of minutes later, Kenny started lathering his semen all over my head. It was my makeshift hair gel. He pulled my hair back with his hands before pulling me up from the ground and having me sit on his lap.
Then he started showering me with praises. He called me all sorts of sweet nicknames and told me how happy I had made him. I didn’t know how to answer to him so I just looked down.
“That will come later baby.” Kenny suggested. “It’s almost dinnertime.”
I didn’t even know what he was referring to.
“We need to get ready.” Kenny added. “Since you are working in the laundry; see if you can smuggle out some fresh pair of clothes for the two of us. I’m sure you know my size.”
“I don’t know if I could do that … daddy?”
“Nonsense, it’s just your first day, you’ll get the hang of it.”
—
After dinner, we were naked in the cell once again. This time, I was tasked with licking all over the upper body of Kenny. I went to work without question once again. I told myself it is what it is and tried my best to drool over the oversized and hairy upper body of the man in front of me.
After I completed the herculean task, Kenny had me laid over his lap. My back was on his legs.
“I told you good boys get to feel good.” Kenny said as he played with the tip of my cock. “I know exactly what you want you naughty little boy.”
What he made me do next would make Oedipus blush. Kenny pulled my head up and told me to suck on his man boobs. Only the nipple was prominently visible out of a very hairy chest. With the whole act, and Kenny playing with my dick ever so gently, my own dick was rock hard.
It didn’t take long before I shot my own load all over Kenny’s hand. Kenny licked his own hand clean before going back to massaging my penis again. Having ejaculated so recently, I felt an intense mix of pain and pleasure.
I begged Kenny to stop and to my surprise, he obliged. I could feel the hardening dick against my back. I knew what Kenny was going to do, but at my post orgasmic state, I felt hesitant.
Once he started playing with my torso and tweaking my nipples, I knew my hesitations would mean nothing and Kenny was going to have his way with me no matter what. So I relaxed my body and let Kenny have his way with me.
“I know it’s wrong to think of you this way.” Kenny said. “But I sometimes wish we could run away from all this and live together. Just the two of us. Man and wife.”
I had a hard time figuring out if he was messing with me or if he was genuinely out of his mind.
“We’ll be together,” Kenny said as he massaged my body. “You’ll clean the house for me, cook for me, and be there for me. I’ll make sure you can have a comfortable life where you will get whatever you want.”
“That would be wonderful daddy.” I didn’t know where we were in his mind. I’m pretty sure he knew we were in jail. He was actively protecting me from other prisoners.
“I’ll come home tired, from a long day at work.” Kenny kept talking. “You’ll be waiting for me at the front door, on your knees, ready to service me.” He started fondling my soft, flaccid dick again.
“Yeah!” I let out a low moan as I started feeling the sting of pleasure at his hands again.
“I wouldn’t even get to go change before you pull down my pants and start sucking my dick. You want me to feel better whenever I am with you don’t you?”
“Yes daddy.”
“I want to reward you after I notice the clean house and smell the delicious meal you have prepared for me. I know your hole has been aching for daddy dick, isn’t that right baby?”
“Yes daddy!”
“I’ll bend you over and mount you right at the front entrance until I breed that beautiful little hole of yours.”
“You can do that right now daddy!” I could not believe I just invited the man to fuck my ass right now. I just noticed that the dream scenario had me all hot and bothered as I was sporting a boner once again.
Kenny kissed me on the lips in response before continuing with his story.
“Then we will go take a shower together, cleaning each other’s bodies. As you keep rubbing my body and get down on your knees, you’ll see that my dick is hard once again. You’ll want to suck my dick right then and there, but I stop you. I don’t want my baby to catch a cold.”
Kenny was looking forward as he was talking. I thought I could see a real sense of longing in his eyes. I don’t know why felt I felt what it did. But a small part of me really wanted to make his fantasy come true.
“We get out of the shower and help each other dry out.” Kenny continued. “Then I look into your eyes and see that you want to mate like an animal. I’ll throw you over the bed and sit on your face. Having you have a taste of my ass and balls before fucking your mouth. After feeding you your meal; we’ll go down to eat whatever you have made for us.”
“What did I cook for you daddy?” I was into the scenario now. Not to mention, my own added horniness. He was describing a happy life of a couple. So what if both of them happen to be men.
I was dreaming of the exact same thing for so long. Only I was the man in the situation. Well, I was still a man in Kenny’s scenario; just not the dominant one in the relationship.
Kenny was taking his time thinking of what food I had prepared for him.
“You have made me chicken with garlic and butter. And there’s apple pie for dessert.”
“Sound delicious daddy.”
“We have our dinner and then we go to see a movie.”
“What’s the movie about daddy?” I thought he was going to describe some vaguely specific porno.
“It’s about the romance between two men.” Kenny had a thousand-yard stare at that moment. “A romance that is not forbidden. A romance that is pure. Two people fall in love, go through hardships, then make it work together. Then we both cuddle together and fall asleep.”
“What if I get horny daddy?”
“You’re too emotional at the time baby.” Kenny sighed. “I know it’s just wish fulfilment. You are my boy, you are so young. And love between two men will always be forbidden.”
“It doesn’t have to be daddy.”
“It is.” Kenny kissed me on the forehead. Then he started slowly kissing me all over my face.
“I have to confess daddy.” I was completely immersed in the role-play.
“What is it sweetie?”
“I wasn’t waiting on my knees for too long.” I said mischievously. “I just got down on my knees in front of the door right when I heard your car coming up.”
“Oh! And what were you doing before.” Kenny grabbed my hard cock at that moment.
“I was playing with myself. Edging myself all day, thinking about you and your delicious cock.”
“Such a naughty boy.” Kenny pushed one finger inside me.
I didn’t feel any sense of pain or discomfort at the intrusion of the finger. As Kenny arched his finger and tickled my prostate a little, I felt a sense of completion. As if I had found something that was missing for my whole life.
“Daddy will you please …” I could not finish my sentence. I was out of breath.
“Of course I will baby.” Kenny did not make me repeat myself or beg to him. “I know just what you want.”
He then had me sit on his lap, facing him. Our cocks were touching. With how much longer his cock was than mine, it felt natural that Kenny would be the one to fuck my ass. He spat on both cocks and rubbed them together for a good minute or so before penetrating my ass with his dick.
The whole time he was fucking me, Kenny furiously jacked me off, making me cum all over his belly. I was completely spent after cumming twice in such a short time. But Kenny had the strength for the both of us to keep pushing me up and down.
He finished deep inside of me and had me sat on his lap until his flaccid dick plopped out of my hole on its own.
We fell asleep once again with Kenny being the bigger spoon behind me.
—
That night I dreamt that I was sleeping with Rina in a large king sized bed. She was sleeping far away from me.
I saw the door opening up and the faceless monster enter the room. I felt agitated waited for the man to fuck the shit out of me. But the moment never came.
He walked closer to me. The faceless man was much shorter than before. He was breathing heavily and I could vividly see an angry cock pulsating right in front of me. He dangled the dick in front of me. I almost opened my mouth and reached over to suck the dick.
But he pulled away and slowly walked out of the room.
I looked around to see that Rina was not there with me anymore.
—
I woke up the next morning with an immense sense of shame and regret. I was sweet talked into gay sex last night. It was forced sex for the first time. But last night? I dreamed of a life together with my cell mate. I played along with it.
Not only did I played along, I helped him fuck me later. I did not know what just happened to me.
Kenny woke up before me. I looked around to see that he was taking a piss. He was still naked, with his back against me. I wondered how could someone get such a hairy ass and back. I had hair around my ass, but my back was completely smooth.
I looked away as he started turning around.
“You’re up!” Kenny said. “Quick, we need to have breakfast. You don’t want to be late for your job.”
I realized I woke up late. I hastily freshened up and got out for breakfast.
Then I worked my way to folding laundry again. My mind was in turmoil as I kept folding the laundry. There was a loud noise inside one of the rooms where detergents were kept. I turned to see what was happening and someone else told me to forget about it.
Two men walked out of the room almost fifteen minutes later. One of the limping. None of them were assigned to do laundry work. They walked out together, hand in hand.
Then I realized that what just happened to me was nothing out of the ordinary and I would just have to keep going with it. And if all of this changes me as a person and shifts my sexuality; then so be it.
—
When I was done with the laundry work, I walked over to the showers. I peeked inside and didn’t see Kenny there. So I waited for 20 minutes, so that I could shower with him. I was looking down for most of the time, avoiding eye contact.
I was surprised and jumped up at the sudden but hard slap on my ass. I felt relieved to see that it was Kenny.
“Sorry I’m late baby.” Kenny apologised. “The game took a little longer than usual.”
—
Showering together properly was a completely different experience. I had already gotten used to being naked with the man. Although there were other people around us; the way Kenny undressed me and made me feel like we were the only ones there.
Kenny led me to the very corner of the very large shower area. There were plenty of shower heads for each inmate to use. But he had us standing under the same showerhead. Letting go off the cliché, Kenny brought up a bottle of shower gel for us to get clean together.
We lathered each other’s bodies with plenty of gel before Kenny instructed me to run my hands along his body. I obeyed him without thinking about the prying eyes. Pretty soon I was on my knees washing his legs. Of course the inevitable happened and Kenny told me to take my time and clean his cock properly.
I knew that this was going to be in my mouth and ass in a couple of hours. So I was more than happy to oblige.
Then Kenny had me stand up and washed my entire body with water first. Then he brought out another bottle from the corner that I was not familiar with. He then lathered me with some other gel all over my body. The sensation was slightly warmer than before. I asked him what it was. He straight up told me that it was hair removing gel. Kenny had me standing there for more than ten minutes like that before washing my entire body thoroughly.
“So nice!” He commented, while running his hand over my ass.
I didn’t even say anything in return and just went along with everything.
That afternoon Kenny had me sit on his lap for more than half an hour before fucking me.
—
In less than a week, I had gotten used to the routine of the prison life.
We didn’t always have sex first thing in the morning. Sometimes I gave Kenny a blowjob and there were times he had me drink his piss.
During the meals, Kenny still fed me by hand from time to time. Then I was off to work after breakfast. I soon realized that the detergent room was mostly used for sex between people that were not cell mates. I assumed there would be other places for sex and the detergent room was just one of them. Some days two people sneak inside quietly. And there were days when one person pretty much drags the other inside. There are kicking and screaming people that come out of the room subservient.
To think of the authorities? The people that were supposed to put a stop to these things? Well most of the days, it’s a guard bringing in a prisoner to use the detergent room.
So I quickly learned to stay quiet about all that. As long as no one else was going after my ass. My ass was pretty well used in the first place.
That usually happens right after lunch. Some days Kenny would take me outside and walk around the prison yard, groping and caressing me all the way. Other days, we would go straight to our cell and do whatever Kenny had in his mind.
The biggest mind warp happens after lights out. I would either sit on Kenny’s lap or we would cuddle each other. And both of us run along with different scenarios of living happily ever after together. I don’t know how to say it, but I tend to get emotional from the talks most of the time.
Most of the time, while having sex, Kenny made sure I ejaculated while his cock was lodged deep inside of me.
I still had vivid sex dreams most of the nights. But in those dreams, the faceless man had formed a complete face. Kenny was the man in my dreams, fucking me constantly. And there was someone else, another faceless figure that kept getting away from me.
It was the third week of my stay, when I came just from him fucking my ass! The pleasure was always there, but the intense pleasure from the dick in my ass was overwhelming at that moment.
I started crying while Kenny was cuddling with me that night.
He asked me what was wrong. I told him the truth. I told him I didn’t know what was happening to me. I told him I was not used to feeling like this. I also told him that nobody ever cared for me the way he did. I didn’t even know if I was going to be able to go back to normal life again.
Kenny told me that everything was going to be all right. He was going to take care of me, no matter what.
—
That night he said something. Something that completely shattered whatever game he was playing with me. I was sitting on his lap, facing him, flaccid cocks muddled together.
He called me by my name. He said that his boy Harry did not have anything to worry about.
Never before did he say my name nor did I call him by his name. I always had to address him as daddy. And he called me by baby, sweetie, son or whatever he felt like.
That was the first time he said the name Harry.
I asked him how did he know my name.
“Why wouldn’t I know the name of my boy?” Kenny answered.
“You never asked me?”
“We have been together for so long!”
“It’s been three weeks.” I suddenly had the courage to ask him something. “Why are you here in prison daddy?”
His face dropped. I knew I was going to get the truth.
“What are you in here for?” He asked me.
“Money laundering.” I said flatly.
“What kind of criminal do you think they are going to put you with?”
“Similar?” I was unsure.
“My name is Kent Bernhardt.”
“O my god!” I exclaimed.
“You might not have recognized me, but I assume you have heard of me.”
Kenny, the man I have been calling daddy, was one of the biggest swindlers in history. He was responsible for four billion dollars vanishing away from the market. He had been given a lifetime sentence by a grand jury.
“But …” I was at a loss of words. “Why me?”
“What kind of question is that? I mean look at you?” He chose flattery. And it was working.
“That’s why everyone respects you?” I asked. “Not because you are some weirdo?”
“Weirdoes don’t get too far in life boy.” Daddy said. “But money can sure help you. You don’t even know how much I had to spend to keep the warden off from you!”
“The warden … of the prison?”
“So many people wanted a piece of you. I had to pay every single one of them.”
I was thoroughly flattered.
“So,” I realized both of us were getting hard. “You have a life sentence?”
“I’ll be out in six months!” He said matter of factly.
“But your sentence?”
“I’ll die in prison in two years!”
“What?”
“I still haven’t figured out how it will play out. But I will be dead in the public eye in two years. Not a lot of people know what I look like. I can blend in pretty easily.”
“But …”
“And you will be out with me.” Kenny stopped me from speaking.
“Wait!”
“I looked at your case. Utter bullshit. Three years for ten million? And you?”
“I don’t even have a parole hearing before one year.”
“I don’t have any parole hearing.” Daddy lifted me up. “Ever.” Then he lined his dick properly before letting me do all the work. “Baby we’ll live the dream life.” I started bouncing on top of him. “Whatever you want.”
“What about your family?”
“They all bailed on me once they heard I had no money.” He said between moans. “They have no … idea. I am dead to them.”
“Oooh.” I was having trouble speaking as I was completely immersed in sex.
“It will be just you and me baby. Whatever you want. Wherever you want to go. It’s yours.”
I was way too turned on with all the talks and the sheer power of the man underneath me. I was subservient to the man for different reasons before. But now it was complete. I was physically and emotionally subservient to my daddy now.
—
The rest of the prison sentence went in a breeze.
During my second month in the prison, daddy straight up asked me if I wanted my ex-girlfriend Rina to lose her job. He told me she is currently single, and having a hard time on the job she is currently in. If I had said the word, she would be out of a job in a week.
I will not lie, my cock twitched when daddy said that. But I told him that just because she broke up with me doesn’t mean I want her to be homeless. She needs a job.
Daddy kissed me on the forehead and told me I was the sweetest boy in the world. Then I went down on my knees and sucked him off.
In the third month, daddy showered earlier than me once. Leaving me in a state of panic. Not because I was afraid of licking his body anymore. But because I was so used to the routine of showering together.
That afternoon, daddy licked my whole body from head to toe. I told him that he could lick me anytime and I would lick him anytime. Just do not miss the shower time together. I loved his wet body rubbing against mine. It was completely different from sweat slicked friction. I had gotten addicted to feeling his hairy body rubbing against my smooth body.
The biggest surprise for me was during the fourth month of the stay. Daddy walked in my work area and told me to open up the detergent room. I thought we were going to have sex inside, so I obliged.
But inside was another man. His eyes were bulging at me while his mouth was gagged. His hands and knees were bound together.
It was the manager of the marketing department that framed me for his own freedom.
“Daddy what the fuck?” I exclaimed.
“I’m sorry baby.” Daddy apologised. “I know you are too nice. So I didn’t ask you before bringing him here.”
“Aren’t you going to get caught?”
“He is currently under house arrest.” Daddy explained. “His family is on a month long vacation. Sadly it’s only for a month.”
“What are you saying?”
“I think you know exactly what I am saying.”
“I don’t want anything to do with this man.” I said.
“You don’t have to.” Daddy said. “He will be in the prison for the next month. He’d have to serve three years in a month. So, maybe block-d and e. He will be passed around.”
“This is a middle aged man.”
“He has two holes.”
“But you won’t be in trouble?”
“Am I?” Daddy asked the bound and gagged man.
The man vigorously shook his head.
I didn’t want to learn about the circumstances of his prison visit.
I didn’t even see the man for the next month. He came to me at the end of the month to apologise. He was limping, and had trouble speaking. He told me that he was sorry for putting me through all this.
I thanked him for whatever he did. He nodded before limping away.
With the sixth month nearly approaching, we were sitting in the yard, I asked daddy once about getting out of prison. Whether he would leave me and go away first. How I would have to stay alone in prison.
He told me that we would walk out together, hand in hand. I blushed as he held my hand. Some other guy told him to fuck me right there out in the open. I would have done it. But daddy took me to the detergent room for the first time that day.
Despite all the sex people were having there, it really smelled like detergent. It was another passionate session of missionary sex with both of use wrestling out tongues together. I came before him once again.
—
Daddy’s words came true. We really did walk out hand in hand less than a month later.
The first month after release, daddy rented a hotel in Paris with Eiffel tower in sight. Of course we fucked every day like rabbits. But we also walked around out in the open. We ate together in different restaurants. Daddy rented out the top of the Eiffel Tower one day and fucked me there. It was exhilarating.
Out Paris trip ended and we came back home. Home was a two story villa in the middle of a bustling city. Daddy was more than capable of hiring maids and cooks for us. But I didn’t let him. I literally wanted to live out the fantasy of being his home maker.
I learned to cook and cleaned the entire house by myself.
This one-time daddy got all emotional and told me that he could not give me the proper title by marrying me in the court of law. I told him that he didn’t have to do that and I was really happy with him together.
Then I went ahead and bought wedding suits and wedding rings for the both of us. After making love one night, I proposed to him with the ring. To be honest, I did not expect him to cry. But he brought out another ring he had bought or me a while ago. Then we had sex again.
A few days later, we had a mock wedding with a handful of guests present in his modest backyard.
—
Currently I am making chicken with garlic and butter. I had ordered apple pie online and it was going to arrive anytime. As soon as I finished making dinner, I heard daddy’s car getting inside.
After parking the car inside the garage, he walked towards the front door with the apple pie in hand.
“Look what I just got.” He smiled at me.
“I’m still not good at dessert daddy!” I pouted.
“Let me guess,” He kissed me on the lips before saying, “Chicken with garlic and butter.”
“Yes daddy!”
“I need to put this down first baby.” He pointed at the apple pie before I got down on my knees and started unbuckling his belt.
He put the pie on top of the shoe rack as I pull down his underwear. I didn’t get to suck his dick for too long before he leaned over and mounted me. We didn’t have sex during shower. We had dinner together and fell asleep in each other’s arms while watching a movie.
I felt a sense of deep elation inside me before falling asleep.