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Prison Initiation

Category: Gay Male
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There is something particularly humiliating about being arrested covered in cum, piss, and surrounded by big black men, especially when you were once a very well-off businessman with a simple insertion fetish. My whole private life had been exposed in a day, and it affected my professional life a great deal. My face was plastered all over the news for weeks. Obviously they weren’t flashing my cum covered naked ass on the nightly news, but plenty of pictures surfaced on the Internet and were making their rounds. It was a huge scandal.

I went from rich, respected entrepreneur to public humiliation and known deviant freak. My parents knew. My friends knew. My girlfriend knew. The whole world knew who I was, and the prison yard was no different. Everyone there knew who I was, but I’ll be totally candid: I loved it that way.

I was a celebrity the second I showed up. The guards knew me, the prisoners knew me, and the warden knew me. Plenty of the Nazi assholes throughout the prison hated me for being a faggot, but everyone knew that deep down they were all faggots too, they just only happened to like pure white dick (yeah, right). You’d be surprised how much gay sex was going on inside this prison. When all that testosterone is packed in and the urge to fuck something just becomes too great, the closest thing to a woman’s pussy is a man’s mouth or a tight, warm, wet asshole. Lots of men are just fine with the compromise.

Since my arrest, I had been pretty down about my life being upended as it was. The trial was short, as I pleaded guilty to get it all over with. They gave me five years for aiding and abetting escaped convicts. I had bought them clothing and food and water in exchange for their relentless fucking of my tight, muscular body. I hadn’t been working out quite as much, being depressed and all, so I had put on about ten pounds, but it all seemed to go to my ass and thighs. My bubble butt had only gotten more plump and soft. It jiggled a little longer now with each smack and thrust, and I actually liked it even more.

My first day in prison was perfectly memorable. Walking through the gates and halls, all sorts of shouts greeted me, from hateful to congratulatory to sexual. Before I was taken to my cell the guards brought me in and took me to a private area. There was a big tile shower, just like the ones they have in prison movies. I noticed that there was no fire hose, though. That was a relief. I had no idea what it was like to get shot with one and I didn’t want to find out. In lieu of a fire hose there was a big, lavish showerhead hanging down in the center of the shower, and another one hanging on a hose in the wall.

The big officer that took me in the room was a sexy motherfucker. His name was Bryan. He had a short-sleeved uniform that hugged his huge biceps and contoured to every rippling muscle he had. Standing 6’6″, handsome, hairy, and his salt and pepper hair made me think of calling him daddy. Best to let him approach me first, though.

“The warden wants us to prepare you for your first meeting with him,” Byran said. “He knows all about your record and he’s interested in meeting you and making sure that you understand very clearly the rules in this prison. They’re pretty simple but he wants to make sure they’re drilled into your head, or wherever.” He let out a big, booming laugh. I giggled, liking where all of this was going. “Take off your clothes and stand still.”

I listened immediately. I was in no hurry to make enemies or piss anybody off. If Bryan had a brutal domineering side I wanted to see it on good terms. My clothes fell to the floor as he turned on the shower. He walked back to the door we came through and locked the deadbolt. I watched him walk his sexy stroll back to the shower and test the water, all the while staring me down with his thousand-yard glare. I was growing slowly, and I could tell he noticed. He looked at my dick and walked over, still glaring. I looked up at him as he came closer. He smacked my dick to the side and grabbed my chin.

“Rule number one: you don’t cum until we say you can cum. You won’t be cumming tonight until the warden is all finished with you, and that is hours away. You can let your fat cock grow all you want, keep it rock hard, but you will not cum until you are told.”

“Yes sir. I won’t cum until I’m told,” I said, thinking about the most depraved acts I could think of this man performing on me. He slapped my cock again, this time harder, but I was still growing, and he was helping.

“Rule number two: You will submit to all guards on duty, and you will please them when they want. We do a lot of work to make sure the guards around here are good looking, in shape, and hung like horses, and you will worship and serve our fine stock.”

“Yes sir. I will serve all guards at all times.” He smacked my cock back and forth a few times, squeezed it, jerked it a little, and then let it hang.

“Rule number three: You will please anybody the warden tells you to, guard, prisoner, or what have you. He’s going through a lot of trouble here, giving you something that he thinks you might actually enjoy, but he’s using you, so don’t forget that. You are his fucktoy, and he can share his toys with whomever he pleases. He meets senators and congressmen and celebrities all the time, and if he needs a favor he will offer up his prize toy. That’s you.”

“Yes sir, I will happily please everyone the warden tells me to.” By now my cock was raging hard. It stood at attention, and Bryan knew it too. He slapped and fondled, walked behind me, smacked my ass hard, and pressed his finger on my hole. Please let there be more.

“Shower.” That was all he had to say. I walked into the steamy water and soaked my body. I knew the water was bouncing off my big round butt, making me look good, so I gave my booty a shake. It jiggled and jiggled, and I looked over my shoulder at Bryan.

“Next?” I asked him.

“Soap yourself up and wash yourself off,” he replied. “I don’t need to tell you to make it sexy, you’re doing that already. Give me a show.” He massaged his growing and now showing member through his slacks. I looked at him with longing and picked up the soap. I stared him in his eyes while I rubbed the soap all over me. The suds formed and coated me everywhere, collecting in different cracks between muscle and flesh, my big dick standing hard and firm on top of my full balls. I stroked it a little as I watched Bryan stroke his. I turned around and got on my knees, leaned forward, stuck my cock through my legs, and smacked my ass hard. Soap and water splattered everywhere, and I stroked my cock with my other hand. I knew he loved the show.

“Stand up, spread your legs, and put your hands against the wall. Do not turn around and look at me. If you disobey me you will regret it.”

I was anxious to obey him. I scrambled to my feet, walked under the water to rinse off, and assumed the position. I stared at the plain white tile for what seemed like forever. The noise of the shower drowned out any noise Bryan might have been making. My only hope was that he was taking all of his clothes off and sneaking up with a freshly lubed cock ready for impalement.

The time ticked by and finally he was standing at my back. He surprised me with a smack on the ass. My cock had gone flaccid and now hung down between my legs. He grabbed the soft meat and squeezed it, tugged on it, massaged my balls. Once he felt it growing in his hand again he let it go. I looked down and noticed that all he had on were his work boots. Everything else was gone. His massive dick swung with each movement, and his rippling abs taunted my nerves.

Suddenly a cold hard pipe was resting on my balls. He pushed it further under me and I saw it peek around my dick and balls. It was his nightstick. It was shiny and thick, thicker than most, it appeared, and it had to be a good fourteen inches. I was absolutely sure what that was for, and I smiled inside and out.

“You see that big stick?” he asked as he leaned down and spoke in my ear with his deep voice.

“Yes sir.”

“That’s gonna go up inside you soon. I’m sure you’ll love it.”

“Yes, daddy.”

He grabbed my face with his hand and pressed his hard body against mine. He stared into my eyes with determination and power. His big muscles dwarfed mine, and his height helped even more. For the first time I felt his meat in between us. It felt almost as big as the nightstick, and it was so hot the shower seemed cooler than it had before. “That’s good, keep calling me daddy, my little slut.” He shoved his tongue in my mouth, twirled it around mine, and we made out hard. My hands left the wall and wrapped around him what they could. He used my back and ass cheeks to stroke his cock as we dry humped while our tongues danced around. I felt like his little bitch already. I let out a high-pitched moan as I bit his lip, and he sucked my tongue into his mouth.

“Oh, yes, daddy, I’m all yours. Show me how hard prison’s gonna be.”

He let out a beastly grunt and kicked my legs wider. Our bodies parted, and he put the nightstick to my lips. I looked into his eyes as I sucked it in between my lips and twirled my tongue around it. My head went back as far as it would go and he proceeded to start fucking my throat with it. It hurt quite a bit, but it had been a while, and I figured a rough warm up isn’t the worst thing that could happen. My throat needed to be ready for his cock.

I gagged and spit all over his nightstick. He took it and dragged it across my asshole to lube me up. The nightstick came back to my mouth, and his fingers began their dirty work on loosening my hole. It had been a while, but I wasn’t worried in the least. I was ecstatic. I sucked eagerly on his nightstick, wishing it was his fat dick instead, but I served him like I had to (wanted to).

The stick left my mouth and he positioned it at my asshole, spreading my cheeks with his other hand. He kissed me again as he whispered nasty thoughts in my ear and pushed the rounded tip of the stick against me.

“You ready for this, you little faggot? You’re gonna drink daddy’s cum after he’s all finished, slut. You feel that real meat pressing against you? It’ll get bigger. Just you watch. I’m gonna turn your asshole into a used up rag.” Stuff like that, getting me hotter and harder. I was doubtful that he would be anything like Deyron, but who knows? He might know a thing or two about this that Deyron didn’t.

The nightstick broke through the barrier of my asshole. It was a familiar feeling that I had missed. It had been a couple weeks since I last had anyone inside me. I was awaiting that hot meat, but for now I was happy to be pegged by this burly, cum filled man. I could tell he was as into it as I was.

The nightstick was eased into me, and when he found my anal canal he pushed it deeper inside with more force. I squealed with enjoyment as he pushed every inch in. The handle sticking out the side hit my cheeks and I felt full again. All twelve rigid inches inside me, following my spine deep into my bowels.

“Turn around and keep your legs spread,” he commanded. I turned to him and looked up at his sexy face. He kissed me with his hot breath and sucked on my tongue some more. He pushed me back against the shower wall and pushed his cock against mine. “Stroke them,” he said through the intense, passionate kissing. I took both of our hefty cocks in between my hands and yanked on them softly. I stroked from the bottom to the head. The nightstick was still lodged up inside me, and Bryan never forgot it. Our hot cocks looked so sexy pressed together. His dick was about an inch longer, and a bit thicker, but I liked it that way. I could only ever submit to a man with a bigger cock. It wouldn’t seem right, otherwise.

Then he threw me for a loop. He crouched down in his work boots and looked up at me from below my cock. One of his hands grabbed the handle of the nightstick; the other grabbed my throbbing cock.

“The warden wants you to have a rather large load for him later,” Bryan said. “He has many freaky fantasies he wants to try with you, and he always loves a big load to gargle at the end of his fun. I’ll suck your cock until you cum at least five times while I work this nightstick in and out. You tell me when you’re close, I’ll try to sense it, but don’t you dare cum. That cum is for the warden, and you will save it. Do you understand?”

“Yes, sir. Anything to please the warden.”

“Good slut.” He hoovered my dick into his mouth and sucked it like an expert whore. My eyes rolled in the back of my head in pure ecstasy. He made all sorts of sloppy noise as he sucked, and then he grabbed the nightstick. He looked into my eyes with my cock several inches in his mouth, gave the stick a wiggle, and smirked. This guy knew just how to get me going. Without warning he pulled the stick out to the tip. I moaned his name, “Daddy,” and tried to focus on one source of pleasure. The stick was back inside of me again, Bryan’s knuckles pressing against my hole.

He had a tight grip on the handle of that nightstick, and I figured he would be getting rough soon. I was right. He started hard with the nightstick, sliding from tip to hilt with some serious speed. Occasionally he didn’t find my canal and my insides felt like a lightning strike, but he just sucked harder and continued fucking anyway. I was close to cumming, and I wanted it bad, but I shouted, “DADDY!” just in time and he stopped sucking. The stick kept pumping, though, and the sudden reduction in sensation was enough to bring me back from the edge. For the next ten minutes he fucked my hole and sucked my meat to the brink of orgasm over and over.

I collapsed after the last one. Luckily he had pulled the stick all the way out. I laid there on the floor, breathing heavy, sweating in the hot water, my dick throbbing, my bubble butt pointed at my user. Bryan laughed at me with his big burly laugh.

“We’re not done yet. Get on up now.” He spread my buttcheeks and spit inside my open hole. The stick went back in and he assaulted my hole with a bunch of quick pumps. I squealed and scurried to my feet, smiling and laughing.

“You’re amazing, daddy. I hope this is my daily treatment.”

“It won’t be our last encounter, I promise you that. Now, it’s your turn to suck.” He reached down and wagged his dick in my face. His huge meat swung back and forth, hypnotized me.

“Yes sir!” I popped my mouth around his dick and brought my hands to his shaft and balls. I looked up at him with my big doe eyes and smiled on his dick. I used everything I had to suck on him. He moaned with pleasure and my paced quickened. His big mushroom head was pressing against the back of my throat, so I adjusted my angle a bit and managed to get another inch inside me. The tight warm tunnel made him twitch. I just smiled and kept pushing. My gagging had gotten much better, and I held him inside me for a while. Finally I gagged and gagged, and pulled his cock out. The sticky slobber came out in strings, connecting lips and cock and balls together. I gobbled him up again and pushed his cock down my throat. This time he went further. I could feel his pubes just barely tickling my nose, but I wouldn’t rest until my nose was resting on his stomach. I worked at Bryan’s meat for a good fifteen minutes, enjoying myself knowing that he was enjoying it. He called me names, held my head down when I tried to pull away, pinched my nose closed and slapped my cheek, fucked my throat at will. I was right where I wanted to be, and he knew it too.

Like a bat out of hell, suddenly Bryan became an untamed beast. He growled and yelled as he held his cock in my throat for a good thirty seconds. I struggled and fought him but his grip was too much. I was gagging and choking. I thought I might have puked, but his cock plugged my throat so tight it must have just gone back down. It seemed like he was cumming, but I couldn’t feel his load. Finally he pulled his dick out of my throat with a grunt and it flopped around, big and hard, dripping all that slobber everywhere. He slapped my face with it over and over, smacked me with his hand, bent down to me, said, “This is your first night for five years, slut. Now I’m really gonna see what you’re made of. Take this spit off my cock, jerk your dick and play with your asshole. I’ll be right back.”

He walked his big, hairy, muscly body across the room with his fat cock swinging and flinging slobber. I marveled at him, wondering how long it would before I would get the pleasure of his domination again. I grabbed the nightstick again and slid down on it, sending it deep. My cock felt so good as I jerked on it, circling the head and taking long strokes here and there. This is what you’ve become: A cock hungry submissive slut. Make the best of the time you spend in here. You might find yourself wanting to stay.

Bryan walked back over to me with a grin. A huge penis pump was capped over his big shlong. He was pumping it slowly as he looked at me. A smile spread over my face as I watched his wonderful penis become inflated and engorged. He strolled over to me looking in my eyes. I stoked my cock and bounced on the nightstick while he approached me. He turned around, poked his ass in my face, and smothered me with it. I leaned on the wall and let him put his weight on me. My tongue lashed at his asshole, my lips smacked and slurped, puckering his tight hole. A stick up my ass, Bryan’s ass in my mouth, my hand stroking my cock, and his hands pumping his cock to an enormous red member. My only wish was that I could watch it all happen.

His beautiful cock grew to the size of the pump, but Bryan kept pumping. It grew redder and redder with each squeeze of the plunger. I backed myself off from an orgasm like a good slut and begged my master for his member. He laughed his hearty laugh and turned around to show me his handiwork. His huge member had filled the entire canister at about fourteen inches long. The three-inch width gave his cock a nine and a half-inch circumference.

“Oh my god, daddy. You know just what I like. Let me see it, please.”

He pulled the pump off his cock slowly. As it came away the sides of his penis inflated beyond the edge of the chamber. Bryan’s big dick had grown to twice its size in every direction. I marveled at it as I bit my lip, eager to see what we were about to do with this thing. The final few inches of his dick popped out of the chamber with a loud pop. I giggled and stared at his huge red rocket. It hung so low now. I picked it up at the base and let the rest of its length sag. It wiggled slowly as I shook it, smiling up at Bryan and kissing the head.

“Oh, daddy. I love this thing. It’s so gorgeous. I can’t believe you’ve done this for me. Thank you.”

With no more hesitation I took his big inflated cock in my mouth with a big slurp. I moaned like a little bitch as I sucked and tongued his dick. Mmm. Mm. Oh yes. Tastes so good. I’m a prison slut. I’m a prison slut.

Bryan threw his head back and let out a loud groan. “OH FUUUUUUCK! Suck my fucking cock, whore!” He grabbed my head and slammed his meat down my throat. I choked on it and loved every second, every inch. I sucked him deep and brought my lips off his mushroom head with a loud pop over and over.

“Yeah, daddy likes that doesn’t he? He likes his little fucking slut. Use me, sir. Use me hard.” I sucked and stroked him with fervor in the sluttiest, nastiest way I could. I had almost forgotten about the nightstick up my ass, but I soon remembered as my thoughts reverted back to my bottom. “Give me your cock in my ass, please, daddy, please!”

Bryan gave my throat a few more hard fucks, held his dick in my throat, let me gag, and then pulled all the way out.

“You got it, slut. Turn around and put that ass in the air,” my master commanded me. I was giddy at the prospect. I turned around as fast as I could, arched my back, took my face to the floor and poked my big round ass in the air. My hands went back and grabbed my cheeks with a smack before pulling them wide apart.

“Oh, yeeeeah! Look at that nightstick, lodged in there still!” Bryan cheered. He reached down, grabbed the handle and proceeded to fuck my asshole with his weapon once more. He was relentless with his long strokes, and when the stick came out he spit all over my hole. He spread his legs and stood over me with his still swollen member hanging hard. He rested his tube sausage in my crack to taunt me with it. The heat warmed my asshole while the weight made my body tingle. It’s coming. He dragged the length up and down my butt a few times as he reached down and squeezed my cock.

“You’re gonna have some serious cum for the warden later, whore. I think he’ll be pleased with both of us.”

Bryan stuffed the head of his cock into my hole hard. All of his gentle treatment had gone out the window now. His cock and balls had taken over and he wanted to spill his thick load. The soft but firm member went in at the perfect angle. His huge deep cock displaced my insides with each thrust.

“Oh, oh. Yes, YES!” I moaned at my treatment. He began to fuck me with serious power now. He sure liked those big long strokes. The sensation in my asshole was hot, tight, pleasurable and painful all at once. A few farts escaped my hole as more air was forced in and out.

“Haha. Fuck yeah, that’s a good slut hole,” Bryan said as he enjoyed my rectum. His cock had gone down a tiny bit in size, but it was still big enough for me. He flopped his cock out, put it in my face, and I sucked on him hard. He fucked my throat, spun me around, and entered my asshole again. The noises escaping our mouths and my ass made for a beautiful, sexy scene. Bryan was in his rhythm now, and I was just enjoying it all. He fucked like a racehorse, and his cock was pretty close to a racehorse as well.

I laid there with my face in the hard tile, my butt in the air, and a prison guard barebacking my asshole with his pumped up penis. It was a strange slap in the face to consider what my life might have become. Would I ever have a normal life again? Do I want one? I could go through life like this as long as I’m taken care of. I was in pure bliss in this submissive position. No matter what I wanted, the next five years would be spent in this place. I was okay with that.

Back to reality, Bryan is still pumping away, and his big booming voice comes out in a howl and groan. His body tightens, his thrusts become shorter, and I know it’s coming. Finally. I had been waiting for some time. No matter how great the sex is, I always want that cum. He pumped his jizz into my asshole, pulled his cock out and came all over my bouncing butt, and moved to my face. I sucked on the tip of his cock as several more cum ropes came free of his balls. I massaged his balls for him and watched the faces he was making. Those masculine grunts and scrunched up faces made me feel accomplished.

My ass hung open for a while before closing up tight. Bryan smacked my lips a few times with his ballooned member as a couple drops of cum stuck to my face. I smile up at my dominator and gave him a sincere thank you.

“What’s next? Do I get to have more fun with the warden later? My balls are getting sore now.”

“Oh you’ll have lots of fun with the warden. He’s got quite the evening planned for you two. This was just your warmup. Now your asshole is primed and you’re nice and horny, so I hope you’re ready for some freaky shit.”

“I am. I can’t wait to cum tonight. Is the warden as sexy and masculine as you?”

“He’s masculine alright. Pretty good looking, yes. He likes some crazy fetish shit, though, so it won’t be your average fuck. Then again, neither was this I’m sure.”

“No, it wasn’t. What now?”

“Stand up and assume the position again,” he commanded.

I listened. He brought a hose over and shoved it up my ass. The power and cold water were such a fucking rush I let out a girly shriek. He pulled the hose out and let me drain before repeating the process several more times. The cum and all the other fluids came rushing out of me. I was clean for the warden. Now I just had to anticipate what was next.

And to think, all this and I haven’t even seen my cell yet. That’s a story for another time.

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