Prison Bitch

This story is fictional and contains gay male sex. Forced sex, Prison, corruption and the like. Please move on if this type of story is not to your liking. I hope the rest of you enjoy.

My birth name is Rhett Collins, and I am a 25-year-old male. I recently graduated with a bachelor's degree in finance from a well know University. I was living a carefree life, the good life, before things took a terrible turn for me.

After graduation I traveled abroad for over a year, partying, and womanizing like a true legend. I do not come from a wealth family, in fact just the opposite, my family is poor. I made money trading Crypto Currency, and through the stock market short selling stock and exchanging currency for currency. I have a way with numbers and making big chunks of cash quickly is relatively easy for me. I should be very wealthy by now and living the American dream, instead I am in a Prison cell, on my knees, with "Whitey's" giant cock in my mouth.

Let me back up. My biggest problems in life is the fact that I am lazy, and I love to party. I didn't really work, I supported myself by trading. When I ran low on cash, I would simply sit at a desk in a hotel room or wherever I happened to be at that moment and make a nice chunk using the stock and crypto markets. Sometimes I could accomplish this task in hours, other times it took a few days even up to a week. I would then go and blow the cash on pussy, traveling, partying and the like. I was having the time of my life, young and carefree.

The last good day I had was in Thailand, lounging on the most amazing beach, soft white sand, turquoise water, warm air with gentle trade winds blowing keeping the temp just right. I had my dick sucked twice that morning by the cutest and tightest little slut in the area named Boonsri. Boonsri was under the impression that I was a big-time stockbroker and that I was going to take her back to America with me, to get married and live a life of wealth and luxury.

I had become a master manipulator of women, and that trait afforded me as much pussy as I wanted; my motto was the Dire Straits song, "Get your Money for nothing and your chicks for free.". I am very good-looking guy with a feminine facial structure, long eyelashes, blue eyes, big lips... I have drawn comparison to a young Brad Pitt. The problem is, I am only 5 foot 7 with a small dick. In order for me to hide my shame I became proficient at lying about my wealth, and I perfected this technique. I always made sure to have a thick stack of cash in my pocket to flash at unsuspecting women at just the right moment, this was a gift I possessed, I suppose.

I preferred to frequent the poorer countries and Thailand was my favorite, as the women are usually more than willing to hook up with a wealthy businessman and live the good life back in the states. My plan worked brilliantly; my strategy combined with my good looks gave me my pick of women from the local talent pool. I loved my life this way as I didn't have to worry about disappointing women back home with my small cock anymore. Growing up with a small cock was a devastating experience to go through from the shame in the locker room to the unsatisfied women I bedded. I don't know what was worse, the dissatisfied look or the look of amusement on the women's faces when they saw my dick and I blew my load in a matter of seconds. This humiliation combined with my sense of adventure led to my overseas lifestyle.

The women I encountered overseas were hoping for a better life based on my false pretenses and they wouldn't dare sneer at my inadequate cock and disappointing performance. Instead, they would enjoy their first orgasm complements of my talented tongue, then fake their way through a second orgasm when I "two pump chumped" them. They would then lie and tell me how good I was, and that I was the best they ever had. This was perfect for me, as I got to eat some pussy and got laid without all of the shame. I was lying to them just as they were lying to me, however I wouldn't stick around long enough for them discover I was a fraud. My life was perfect.

Back to the beach in Thailand, I was admiring Boonsri's ass, her pink bikini hugged her in all the right places and contrasted brilliantly with her brown skin, as she walked down to the water from our beach chairs to cool off. I was sipping on a "fufu" drink when I got a call informing me that my parents were killed in an automobile accident. I was devastated and made my way back to the states.

I have no siblings or friends to speak of except for a long-lost uncle. I was left a mess of an estate -my parents were in debt and that responsibility was passed on to me.

After a very emotionally draining funeral, I was sitting alone in my parents small living room, drunk and depressed. I opened the Will my parents left, I already knew they had left nothing to me but debt, but I read through it anyway.

Tears were flowing down my cheeks as I read the last of my fathers' words:

"Don't end up broke and miserable like us son, you are much smarter than that. I beg of you to apply yourself and become a success, change our family name for the better. Make us proud son."

Two weeks later I started working for a massive hedge fund company and we managed trillions in assets. This is where I met my fate.

I was too smart for my own good and my propensity for being lazy got me into hot water with SEC in record time. I was looking at Prison time when my boss approached me with an indecent proposal. He basically said that he could use his connections and power to get me off the hook with no prison time. My boss - Mr. North - is connected and extremely wealthy and powerful. All the wealthy people in this circle "play ball" with each other including some players inside the SEC, judges, prison officials, the FBI, politicians, etc. Anything can be had or accomplished for the right amount of money transferred into secret and untraceable crypto accounts. Add in few insider stocks market tips at just the right moment and you have powerful friends in powerful places at your disposal.

Mr. North proposed that I become his personal cock sucker, his personal fuck toy in exchange for my freedom. I was devastated, disgusted, and terrified. I declined his "offer" thinking that I could outsmart him and the SEC, not fully underestimating the dire situation I was in. The last words he said to me were:

"Big, big mistake Rhett, you underestimate my power and your crime, you will surely get a minimum 5-year sentence, but I will make sure you get 25 years instead pretty boy. One way or another you will be sucking cock; I always get my way sweet lips. I would advise you to become my girl, you will be free and wealthy living in luxury. If you decline my generous offer, you will become a prison bitch and I will get to fuck you anyway. I can guarantee that your slutty lips will be locked around a big cock within 15 minutes of entering your cell. You may as well take my offer, sucking my cock while my driver takes us to a 5-star restaurant, or while traveling to many of my properties throughout the world sounds better than being a prison bitch, right?

I contemplated my disgusting boss's proposal for 5 seconds before telling him to fuck off. I was not a fag and could beat these charges.

My trial went fast, I was convicted and sentenced to 25 years in Prison. I got sent upstate, not into the country club prison that is usually reserved for financial criminals like me. Mr. North wasn't lying when he warned me of his power and influence. My crime should have been a 2 to 5-year sentence in a country club, but I didn't have enough time to make enough money to pay for the type of lawyer that could have exposed Mr. North. Mr. North wouldn't have allowed a good lawyer to defend me anyway so instead I got a public defender who I suspect got his own crypto account filled to the brim as he was useless.

So here I am in Prison, I just finished getting processed and am getting ready to be let into the cell block and to my new cell. I am terrified and shaking as the inmates started cat calling me as I walked.

"Shake that ass sweetheart."

"Look at those cock sucking lips."

"You're going to be my bitch faggot."

It went on and on as I finally made it to my cell. Leaning against the wall next to the door were a couple of tattooed white prisoners with bald heads, they were mad dogging me and licking their lips when the scariest looking of the two said:

"You better race up peckerwood or the black guerrilla family will make you their bitch before they kill you - white boy. Whitey has granted you a temporary protection for next few hours and you will have our temporary protection. This protection expires before lights out tonight, choose carefully."

With that I entered my cell, sweaty and shaky, I felt nauseous. There were two bunks, one occupied someone's belongings and the other was empty. I put my meager belongings on the empty one and sat down. I was trying not to cry, disgusted with the racist men outside when a very large and scary looking white man appeared at the door, he nodded for me to join him outside. The man was covered in tattoos, his head was shinny bald and his eyes were dark and evil looking. He was huge and chock full of muscle. This beast of a man would be able to squash me in one second if he wanted to. Being the coward that I am, I jumped up and scampered to his side like a bitch, this was my first mistake.

This man's name is Whitey, and he runs the prison. He is the leader of the white prison gang and controls the drug trade, prostitution trade and just about all other trades inside of this prison. This was my first day and at that time I had no idea how powerful this thug was. I was about to find out though.

Whitey gave me an ultimatum, choose the whites and their protection or he would hand me over the black guerrilla family, and I was told they would use me then kill me. I am not racist, and I despise everything about racism, but I had no choice here. If I refused the AB's protection, I wouldn't be accepted into the black guerrilla family or the Asian gangs, or Latino gangs, I would be on my own and eaten alive. This is a hard truth about prison, it is dived along racial lines -- either get in line with your group or you won't survive.

Whitey was staring me down as he finished his ultimatum, there were three black gang members standing nearby and ready to pounce if Whitey withdrew his protection. Being the pussy that I am, I agreed to Whitey's proposal and a big terrifying grin spread across his face. Whitey barked a few orders to his soldiers as the black gang members walked away with disappointing looks on their tatted-up faces. Whitey's loyal soldiers immediately scrambled into action, and I saw one of them talking to a Prison guard who then disappeared through a locked door.

I was relieved that I wasn't just beaten up, raped or worse, but I had a sick feeling about Whitey. He sounded ignorant, his vocabulary was terrible, and he smelled of sweat and BO from his weightlifting and exercise routine as he put his giant arm around me and led me to my cell.

"Get your shit and follow me" he barked.

I grabbed my bed roll and meager belongings from the bunk and followed Whitey to his cell. I couldn't believe he had the power to move me like that, but he did. He let me put my things down and make my bed. I had just put my things away where Whitey had instructed me to when he told me to re-make his bed. Terrified, I did as I was told and made his bed, I noticed him looking at my ass as I did so, he then took me out to the yard with his arm around my shoulder.

All the cat calls had stopped, and nobody was mad dogging me, I felt safer, I think. He took me to a weight bench area and said:

"Sit here princess, in the shade and stay cool, I need to pump some more iron before chow."

'He just called me princess, what the fuck, oh my god I'm in deep shit.' My hands wouldn't stop trembling while I stared at the ground like a coward.

"Look at my arms princess while I bench this stack."

I looked up and heard a chuckle in the distance. I watched his huge biceps flex as I was instructed while he pumped out 5 sets of 15. I didn't dare disobey this scary man even though every ounce of my being told me to bolt, to sprint to the wall and try to scale it. Instead, I sat perfectly still like a fucking coward and watched Whitey pump iron.

After chow and the cell door shut I almost fainted. I went to my bunk and buried my head in the corner as Whitey's massive frame stood before me.

"Listen up pussy, we are going to go over the rules and there are going to be a lot of them, but first things first. I need a fucking nut, so take off your clothes and kneel before me. My cock has been throbbing all day in anticipation of your sweet mouth."

I froze for a full minute; I was terrified and in shock when suddenly out of nowhere I felt a sharp pain on my face, I went down, and I went down hard. I came to a couple of minutes later and as I regained my bearings; I saw Whitey standing above me, stroking the largest thickest cock I have ever seen. It was long and fat with veins popping out everywhere, it was as thick as my arm. His balls were massive and hung down low (they reminded me of the giant nut sack the neanderthal hangs from a tow hitch on the rear of a massive dick enhancing truck) he looked at me and spoke mid stroke:

"I don't want to fuck up your pretty face so don't make me Princess. When I give you an order you do it, you do it immediately without hesitation or your punishment will be swift and painful. Now, let's try this again - STRIP."

I immediately unbuttoned my shitty jump suit and removed it along with my used slip-on shoes and socks. I was kneeling with a pair of stretched out prison issue underwear and my new black eye, nothing else.

"Everything bitch."

My hands trembled and tears ran down my face as I removed my underwear. I hung my head in shame as my little limp dick was exposed. The beast of man standing before me took a seat on a stool, his muscular and tatted legs were spread wide, and his balls were hanging low. He had a giant bush of black pubic hair that was matted and sprawling everywhere, his massive cock stood straight up telescoping out of the thick thatch of pubs. The thick throbbing cock was leaking precum, and the deep-seated veins were pulsating. He told me to stand as he wanted to inspect his property. I stood with my head down, never making eye contact, my body was trembling uncontrollably with fear and humiliation, I could hear him stroking his cock behind me.

"Turn slowly slut, I want to see the rest of my property, especially that ass. That's a good girl. Stop. Now spread your legs wider, wider, that's good. Now reach down and grab your ankles. Ooohhh you have a very nice ass and look at that tight pussy, I'm going to have to stretch you out carefully, as I don't want to damage my new cunt on its first night, the infirmary here is a joke, they will never stitch you back up right - and I like my pussy tight."

My tears were dripping on the concrete floor as my hands were wrapped around my ankles, my head was just a few inches off the ground and my feet were spread wider than my shoulders. I was to learn that this horrible position is called "present", and I would come know it well.

"Now without moving from your current position remove your hands from your ankles and reach back to your pussy. Yes. Just like that. Now spread your ass apart, I want a real good look at that virgin hole."

Whitey stared at my asshole for a minute as I trembled, I could see his massive cock throbbing through my legs as he grabbed something from under his bunk. He was doing something at the sink when he told me to come over. There was a small hose attached to a thin nozzle that attached to the tip of the faucet. Whitey lubed the tip and gently worked it into my ass.

"That's it princess nice and slow, we don't want to damage that precious little quim now do we?"

Whitey was whispering in my ear like I was his girlfriend as he "douched my pussy." He was rubbing my back and my ass softly; his fingers were running from my feet to my shoulders as he gave me my first ever enema.

"You will need to do this several times a day, keep this pussy clean. I hope you paid attention as I don't like to repeat myself. I will go over the rules later but for now get back to "present position."

I was back in present position as he devoured my ass pussy with his tongue. He started near my balls and licked upward hoovering around my asshole, tonguing it deeply, sucking it, then repeating the procedure. Nobody has ever licked my ass before, and it was nauseating having another man dominate me like this.

"You have a tasty pussy princess. Do you like it when I penetrate it with my tongue you slut?"

I managed to squeak out a "yes" terrified of what would happen if I didn't answer when the monster slapped my ass so hard, I almost screamed, the sting was almost unbearable.

"You always address me as Sir when in the yard but its Daddy when we are alone. There will be some acceptations to this rule like Mr. Whitey, or sometimes Master will be required. Now try again."

I let out a meek "Yes Daddy", with a shaky, cracking, and sobbing voice.

"I like that sound princess, we will work on your "sexy voice," and in time you will perfect it, we have all the time in the world to work on this slut. Now stand up straight and swallow these two pills."

I did as I was told and stood without asking, fearing for my life. Sir massaged my ass and stroked my little limp dick as I swallowed the pills with a small glass of hootch that Whitey provided me. The hootch tasted like shit but I felt an immediate slight buzz and was grateful for that. I was to learn later that the pills Whitey fed me that night and twice a day, every day after that were estrogen and a super strong dick hardening pill - that kept my little dick hard most of the time. The estrogen would eventually give my body feminine features, fattening and rounding out my ass, it would soften my skin, and I could even grow a small set of Titties.

Whitey was still caressing my ass and balls when he yanked me down to me knees, I was on all fours and my asshole was sticky and wet from Whitey's tongue ministrations. Whitey slid the stool in front of me and sat down. He grabbed the back of my head and pushed down until my lips, were touching his large cock head.

"Lick it up slut, your tight little pussy and slutty ass shaking has created a mess of precum."

He gripped my hair tight with my slight hesitation, so I stuck out my tongue then licked. It was salty and horrible as I licked the sticky substance and brought it into my mouth via my tongue.

"That's my good girl. I can tell this is your first cock, so I won't punish you to severely for this subpar blowjob that I know is coming. You are going to need to pay attention to the techniques I am going to teach you, I like my cock sucked a certain way and you will need to master that. You will be rewarded when your cock sucking skills improves and punished when they are lacking, or you forget the techniques I am generously teaching you. Now take the head inside your cock sucker, that's it just the head. Now suck it like you're giving your high school girlfriend, "old Susie rotten crotch", a hickey. Yes, just like that. Now arch your back and get your ass up. Higher, that's my good girl. You will always present your pussy like this when your sucking cock. Now suck the head harder whore. That's it. That's the way. That's my good girl. Yessssss, very nice you might just be a natural at sucking cock."

"Its time to take it a little deeper now, that's it princess, take my cock inch by inch. That's a good, good girl, that feels really nice. Now put your hands behind your back, keep your pussy up and back arched, no slacking. Your lips were made for sucking this dick, ahhhhh."