All XXX Penitentiary Pussy Butt Boi
A story of what I whish had happened when I was in prison
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Hi: My name is Bobbie. Would you like me to tell you how I became a Penitentiary Pussy-Butt-Boy? Well, it all started with a robbery gone wrong. I wasn’t even in the bank when the guard got shot and I still got almost as much time as the others. So, not long after the trial I was sent to the state’s newest Maximum Security Prison. When I arrived I was stripped searched, given prison clothes and sent over to a desk where an inmate clerk was working. He told me what cell to go to and how to get there. At the time I had no idea why he and the other inmate worker were laughing and joking. I just thought it was because of the poorly fitting prison clothes or maybe some joke about my long dark hair. When I got to the assigned cell there was nobody there but the bottom bunk was empty so I put my stuff on it and made it up neatly with the bed-roll I had been given. After a while as I was looking out the surprisingly large, very much shatter-proof window that faced the walkway of the main compound, the cell door clicked open and a moment later my new cell partner walked in. Leroy was a very large and very dark, Negro. He was easily 6’5” and 250 pounds with heavy facial features and large pinkish lips. He was wearing the all-white clothes of a kitchen worker. He grabbed a bag hanging off the end of the bunk and told me he had to get a shower and would be back at lock-in time. After about 90 minutes there was a lot of noise on the tier and over the P.A. system. All the doors on the wing opened and Leroy came back in the cell. It seemed he had just gotten out of the shower as he was wearing plastic shower shoes and a robe. The guard went by for count while Leroy was unpacking the bag and putting stuff on the small shelf. After the guard passed Leroy pulled a large jug of homemade wine out of the bag. “Got a little something to help ease ya’ first night in this fuckin’ place,” he said. He put two large cups on the sink and filled them up. He passed one to me and told me, “It ain’t the best tasting shit around, but it got a kick to it.” I tasted the wine and he was right it didn’t taste very good but the alcohol content was obvious.

After we finished the wine he pulled a stack of magazines from under his mattress. He handed them to me and said have a look at these. They were dirty mags and mostly seemed to feature older Negro men having sex with young white girls. While I flipped through the very graphic magazines he took a large bottle of lotion from the shelf and set it on the sink/toilet combination that was towards the front of the cell. “If I don’t gets this lotion on my legs while they still damp they gonna itch like crazy tomorrow.” He explained as he put his foot up on the rim of the toilet. When he leaned down to start rubbing the lotion into his ankle and lower leg the robe he was wearing rode up and I could tell he was naked underneath it. In fact I could see his sack and apparently long penis hanging below his thick leg. I had never seen one that hung down that far before. I turned my head quickly back to the magazine when I saw him look my way, maybe too quickly, and I was sure he could tell where I had been looking. He worked his way to his thigh and applied the lotion slowly there. I eventually noticed that while I could still see his large hanging sack I couldn’t see his penis any more. This didn’t make sense until he switched legs and put the other foot up on the toilet. When he did his robe fell open and I could see his penis again. Now it was sticking almost straight out and was at least half the length of his thigh and as big around as my wrist. He seemed oblivious to the fact that his robe was open and bent down to rub lotion into his lower leg but this time moving quickly to his right thigh. As he now slowly rubbed the lotion into the dark skin of his thigh his wrist would occasionally brush his semi-stiff thing causing it to wag and wobble. I didn’t want to get caught staring, but his thing was so big, I had never ever seen one so large, it looked just like the ones in the magazines, and I had always though those were only so big through trick photography or something. With the effects of the wine really starting to hit me I was quickly losing my sense of discretion and kept sneaking peeks at it.

He continued to rub lotion into his thigh and occasionally stroked it down the thick shaft of his thing too. He eventually capped the lotion bottle and stepped closer to me to put it on the shelf. However he didn’t remember to tie up his robe so it remained open and his stiff thing was now pointing slightly up and right at me. I couldn’t help but see it as it twitched a foot from my face. “See anything you like”? Leroy asked his voice slightly tight. I don’t know what came over me, partly the wine’s fault I guess, but I responded, “Yes, and the magazines are nice too.” This while looking right at his big thing. “You like it, go ahead and play with it”, he suggested and took another half step closer. I reached up and stroked it lightly with just my fingertips causing it to throb and jerk upwards. “You ever play with one before?” he asked. “Kind of.” And I told him a little about the times Coach Parker got in the shower with me after a swim meet when I was eleven. “Coach ever teach you how to suck it?” Leroy asked. “Yes, a couple of times.” I admitted. “Why don’t you go ‘head and show me what you learned.” It was more of an instruction than a question and I put the magazines on the bunk, slid off the chair to my knees in front of him and wrapped my hand around the thick dark shaft I had been petting while we talked. It was so thick my fingers didn’t quite go all the way around. I stroked it slowly a few times then kissed the tip. “Go ‘head now, get busy.” He told me. I slid my hand almost all the way up the thick ten inch shaft and pulled the foreskin back revealing the plump pink head. I wet my tongue with saliva and applied it to the plump head, licking it around a few times to make sure it was all coated with spit the way Coach Parker had taught me. Then I slid my lips over it. At first I could only get the head into my mouth, but I soon relaxed my lips and jaw and began to slide my lips down the hard shaft of his huge Negro penis. I bobbed my head up and down a few times and took my mouth from it to look at it while I stroked its full length.

As I stroked it a bit of thin fluid oozed from the tip. I licked the salty fluid off and took the head back into my mouth and began sliding my lips up and down his big hard thing. He was fully erect now and he placed his hand on the back of my head, pressing my mouth further down his enormous hard dick. “Suck it harder”, he grunted and pushed his hips forward forcing almost two thirds of his big Negro dick into my inexperienced mouth. I gagged a bit when the head of his penis tried to enter my throat, but his strong hand kept my mouth in place and his dick buried in my mouth. “Faster.” He whispered. “Suck it faster.” His hand directed the pace of my mouth on his hard dick and soon my lips were flying rapidly up and down the huge ebony shaft while the pink head popped into and out of my throat with each stroke. I grippe d the base of the big black dick with my hand and felt his balls tighten as he placed his other hand on the back of my head. Leroy started pumping his hips in rhythm with my stroking mouth and hand. “MMMMMMMM” he moaned and thrust his hips forward, “God Damn! Suck it! Suck that dick”, he commanded. He rose up on his toes trying it seemed to force the remaining few inches of his big penis into my mouth. His hips jerked and the huge ebony penis twitched in my mouth. A wet heat began filling my sucking mouth. With so much hard cock in my mouth there was nowhere for the thick goo to go and it poured out of my mouth all over his hard thing, down my stroking hand and onto his big tight balls. The flood of salty goo just kept pouring into my mouth running down making his penis slippery and sticky at the same time. “Damnnnn, take the cum, take it.” He groaned. “Oh, fuck yeah. Suck that cum.” He moaned as his Negro dick twitched a few more times then slid wetly from my mouth. “Damn, Coach taught you good. You damn sure can suck a dick.” Leroy told me as he caught his breath after the full orgasm he just had. “You a messy ‘muther fucker though.” He stated, looking down at his sticky, gooey a dick and balls. “You just gonna have to lick it all clean.” He instructed and put his left foot up on the lower bunk. His cock and balls hung freely in front of me as I knelt before him. “Go on. Lick up the mess you made. Lick all that cum off my balls.” He demanded. I leaned forward and slowly began to lick the man-goo from his hairy balls. “You gonna have to lick ‘em harder than that to get the cum off of ‘em.” He told me. I placed my hand behind his heavy dark sack to hold it still while I did as I was told. I licked his balls with my entire tongue wetting and cleaning them. After I had cleaned the white goo from his balls I began to clean his flaccid but still large penis. I licked the shaft with long slow wet licks again and again until I couldn’t taste his salty stuff on it any more, then I cleaned up the head, licking and sucking it until it was nice and clean. By the time I finished cleaning all the goo from his cock and balls he was getting partially stiff again. He stepped away from me and went to the cell door looking out the gap in the steel door towards the front of the long prison tier. When he turned back around I started to stand up and got a massive head rush. I was so dizzy I dropped straight back to my knees. “What’s wrong? The wine hitting you that hard?” he asked. “I guess so.” “Ease up on the bunk and lay down.” He guided me. I started to get up on the bunk and was hit by another rush at least as strong as the first. I turned to lay on my back but Leroy told me. “Na’ don’t lay like that, roll over on your belly and the room won’t go spinning on you.” The small cell had seemed to want to start to spin so I tried it and he was right the spinning stopped. “Thas’ right just stretch out and relax, you’ll be better in a few minutes. “ He was still naked and his big thing was at least halfway hard again as he sat on the edge of the bunk and began to rub my back and shoulders. “Just relax, you fight that wine it’s only gonna get worse.” I tried to relax and started feeling really woozy. I could’t believe how strong that homemade wine was. After a few minutes I must have passed out, tough I seemed to remember Leroy rubbing my arms, wrists, legs and ankles. When I woke back up a few minutes later I looked up to see Leroy standing by the bunk rubbing oil up and down the shaft of his fully erect penis. I tried to roll onto my side to ask him what he was doing that for but it seemed that while I was out my arms and legs had gotten tangled up in the sheets of the bunk. Leroy saw me moving and said, “You jus’ lie still now, If you fight it, it just gonna hurt more.” That’s when I realized I wasn’t tangled up I was tied up. I also quickly discovered that my shorts and underwear were gone and I was on the prison bunk naked! Leroy rubbed more oil onto his huge Negro penis and then climbed onto the narrow bunk behind me. “You gonna be Daddy’s girl tonight.” He told me as he lowered his weight on top of me and pressed his enormous dick between the cheeks of my naked butt. Even Coach Parker had never done that. “You feel that big dick between them fine white cheeks?” he asked. “Wait. What are you doing?” I asked helplessly. He lifted his weight off of me a bit and slipped one hand between us, taking his rock hard dick and rubbing its oily head around and around until he found my tight pink hinny-hole. He pressed it against my opening and started to push forward. “NO! Leory don’t!” I begged as I realized he meant to push his giant dick into my hole. “It’s to big.” I protested. “It’ll never fit.” I tried to explain. “Oh, it gonna fit.” He grumbled as he pressed harder. “You taking all this dick tonight!” The huge pink head was stretching my hole open and with the oil lubricating it the massive dick was pushing past my clenched sphincter. Leroy pressed down again, this time even harder and the big head popped into my butt. “NOOOOOOOOO!” I wailed. “IT HURTS! TAKE IT OUT! PLEASE IT HURTS! I screamed. My wails only spurred him on and he pushed half of his huge hard Negro cock into me with a powerful thrust. “AAAIIIIIIIEEEEEE! ITS TOOOO BIG! YOUR DICK IS TOO BIG!” “That’s right, Daddy like to hear his girl scream.” He whispered in my ear as he hunched on top of me and pressed even more hard dick into my aching hole. “GOD IT HURTS IN MY BUTT, PLEASE TAKE IT OUT! I moaned through the pain of the massive black penis splitting my white bottom apart.” PLEASE STOP!” Leroy eased up and withdrew his dick from my hole, and for just a moment I thought it was over. Then he drove the gigantic dick right back into me, burying its full length inside my butt, driving it into me until his hips pressed my body to the thin mattress of the prison bunk.

“NOOOOOOOOOOOOOOOO!”, I wailed again as the pain of his huge penis penetrating my body rippled through my entire core. “PLEASE, IT HURTS!” He pulled his hard ebony dick halfway out and drove it in again. “Beg for that dick, Bitch.” He ordered. “Beg for it or I just going to fuck you harder.” He warned. I didn’t know what to do. How could I beg for something that hurt so much. “Beg Bitch!” he demanded again after a full deep stroke of his hard cock into my aching ass. “Say: ‘Fuck me Daddy.’” Being tied up and much smaller than the huge black man that was raping me I thought my only hope was to play along, so I said quietly, “Fuck me, Daddy.” Louder, Bitch. Say it like you said “No”, whore!” he ordered as he continued to ram his massive hard cock into my ass with increasing pace. “Fuck me, Daddy” I said in a more or less normal voice. He seemed to like it and slowed the pace of his strokes for a moment. “Say, ‘Make me, Daddy’”, he now whispered into my ear. “Make me, Daddy.” “Louder, bitch”, he demanded and pushed his cock into me to the hilt. “MAKE ME, DADDY.” I screamed as the big Negro dick hit the bottom of my insides, sending a shiver up my spine. “Again!” “MAKE ME, DADDY!” I moaned loudly as the massive ebony cock filled and stretched my pink hole. Leroy settled into a solid pace, running his big Negro dick in and out of my now oil slicked hole. The tight ring of my butt-hole felt every bump and ridge of his massive penis as he slid it in and out of me again and again. He pumped away at my hole for at least ten minutes, ramming it all the way in and pulling it almost all the way back out. A few times it did pop out and he would stop for a second, reach down between us, find my hole again and ram all of his massive ebony dick right back into me. Slowly he picked up the pace of his humping, driving his cock into me faster and faster. Leroy was fucking me good and hard by the time he said, “Say, ‘Cum Daddy.” “CUM, DADDY!” I wailed loudly. “CUM IN ME, DADDY!” I added without prompting. The thought of his massive cock spewing man-goo into my butt like it had in my mouth suddenly excited me and I begged again, “CUM IN ME, DADDY! FUCK YOUR CUM IN ME!” I begged and realized I meant it! His huge dick still hurt, but I started to pump my hips back to him in time with his powerful thrusts. I wanted his cum! I desperately wanted the heat to pour from his Black cock into my hole. “FUCK ME, DADDY. FUCK ME!” I screamed louder than I had protested the first painful penetration of his massive member. “PLEASE, FUCK ME, DADDY! MAKE ME TAKE IT, MAKE ME TAKE IT ALL!” I moaned as I writhed on the prison bunk beneath him. “Yeah, Bitch, I knew you wanted this dick.” Leroy said as he slipped his arms under me to come up and grab my shoulders from below. He pulled me towards the bottom end of the bunk and drove his cock into my tight hole again and again. “Yes, Daddy, Fuck me!” I pleaded, “Fuck me good.” “Yeah. I knew you was gonna like this big dick.” He grunted in my ear. “You gonna be a fine girl for your Daddy.” “God yes!” I moaned as I squirmed beneath him, meeting every powerful thrust of his massive penis with my pumping hips, God, how I wanted him to cum. FUCK MEEEEEE! FUCK ME, DADDY! His Negro cock was huge inside me, twitching as he began to cum deep inside my butt hole. “Do me Daddy, do me naughty. Please, make me be your naughty girl.” “FUCK YES!” Leroy groaned as his big black balls tightened, his dick twitched, and he began to pump cum into me. “Take it you cum loving whore, take Daddy’s nut.” “CUM, DADDY. CUM IN ME, FUCK YOUR CUM IN ME!”, I begged as he pumped his man-goo deep into my pale hinny. “FUCK MEEE, DADDY, FUCK ME! He pounded me hard and fast with his thick hard dick until his balls were empty and his penis grew soft and slid from my oily cum filled butt. Leroy got off of me and sat on the edge of the bunk. He began rubbing my bare bottom with his big rough hand. “That was some damn good ass. I can’t wait to fuck it again.”

“Are you going to do it again? I asked, half afraid he would say yes and half hoping he would. His huge Negro penis had certainly hurt but somehow it felt good to be his girl for a few minutes and I realized I wanted to be this black man’s girl all the time! “Naw, that’s about all the steam I got for tonight. He told me. “We aint gonna have any problems when I takes them ties off, are we? “No.” I promised and added, “Daddy.” As my new Big-Dick Prison Daddy untied me from the bunk he instructed me to shave my legs and underarms the next day, and pretty much everything else. He wanted me hairless except for my long thick brown hair. The next day Leroy went out to work and reminded me of what I had to do that day. He also said he would have a nice surprise for me if I did as I was told. So I did something I had never done before; I shaved my entire body. At first it seemed a bit odd but as I did it and saw the results, and felt the results I got more and more into it. I rubbed baby oil all over my freshly shaved skin. I loved how smooth and sleek I felt, so much so that my thingy got stiff a couple of times, but I resisted the urge to play with it and just let the excitement build until my new prison Daddy got back. It took most of the day but by the time Leroy came back from his job in the prison kitchen I was completely smooth. Only my eyebrows and long brown hair remained. When Leroy did come he looked at at me and just said, “Looks like you got it done right. I'll have that little something for you when I gets back form the shower.” I had no idea what it could be but somehow I figured it would have something to do with being naughty again with his huge Negro thingy. At the same time it had the night before the cell door popped open and Leroy came in. He was carry a paper bag as well as his usual shower bag. He put his stuff from the shower bag on the shelf as he waited for the Correctional Officer to go by and count. The paper bag was sitting on the bunk and the anticipation was killing me. Once the guard went by Leroy pulled another big jug of wine from the paper bag and poured cups. I figured he intended to get me drunk and rape me again.

He sat in the chair at the front of the cell and ordered me to take of my clothes. “Let's see how good you did what you was told.” he said. Even as I was doing it I couldn't believe I was stripping for a Black man. But I did it, I took off everything and kind of even stood on my tippy-toes a bit for him. “Damn, you did get it good, you smooth all over.”, he complimented me. “Turn round let me see that back-side.” he instructed. I did and stood up on my toes even more. I swear I could feel his eyes on the smooth cheeks of my round pale bottom. “Here you go.”, he said and tossed me the paper bag, “Put this on.” I opened the bag and inside was a white dress with pink straps and a pink ruffle at the bottom of its short skirts! It looked to have been made from old prison sheets and was fairly thin and sheer. At the bottom was a pair of bright pink panties made from the T-Shirt material. My heart skipped a beat and then raced as I pulled on the panties and slipped the dress over my head. All to the approving stare of the large Black man I was locked in a cell with. Leroy had undone his robe as I dressed and was stroking his big Negro penis to full erection. The dress was quite short and showed off my long smooth legs, the homemade panties were a bit snug but I did like the way they cupped the cheeks of my butt. “Now you looking like Daddy's girl ought to.” I couldn't take my eyes off his massive hard penis, remembering what it felt like the night before when he raped it into my butt. “Spin round for me, let's see what it look like.” I turned and twirled a couple of times. The loose ruffled skirt of the little dress brushed my thighs as I did and made me shiver. “Come on over here and make Daddy feel good.” He ordered spreading his legs wide so I could kneel before him. I stayed on my toes as I took the three small steps necessary to cross the length of the prison cell and eased down to my knees in front of him. I softly petted and stroked his big black hard-on.

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Misquimakas
Incredibly Wonderful!  Thank you for this enlightening piece of visually dynamic adventure.
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Misquimakas
I LOVE this Story!! Please make or submit MORE! I think it's even better if the Sissy is Forced or coerced into becoming  "Penitentiary Pussy-Butt-Boy!" Thank you So Much.
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