Long story yet again, but enjoy. I really loved writing it and I hope you all love reading it. Love to hear your feedback, so let me know what you thought.
The two weeks had come and gone. Tomorrow was the pageant. All of the new inmates, including myself, were nervous with no clue as to what was going to happen tomorrow, but the look on the other inmates faces wasn’t very gratifying. Tyrone took me by the hand that night and pushed me down onto his bunk. “Let’s see how far you’ve come sissy,” Tyrone said, “pucker up them lips and kiss my cock.” Almost without hesitation I kissed Tyrone’s fat cock and got to work. “That’s a good bitch” he said, “get my cock nice and hard.” After about 15 minutes of sucking his juicy black cock, Tyrone finally said, “Alright bitch, we gotta keep you loose for tomorrow. Get on yo hands and knees and stick that ass up in the air. Make sure yo ass is presenting itself to the host cock. That’ll be important for the pageant” he said. So as Tyrone fucked my ass for the next 20 minutes I laid there thinking exactly what this pageant may be, since Tyrone had just given a bit of it away. Tyrone finally came in my ass, threw me out of his bed, and went fast to sl**p. I laid in my bunk for a little while longer contemplating. One of the guards must have heard me, because next thing I hear is “Hey! Get your ass to sl**p.” I tried sl**ping, but just couldn’t. 10 minutes later the same guard walked back. “Alright sissy, if you can’t get to sl**p I think I have something that can help you out. Come over here by the door and get on your knees” the guard said. I crawled down from my bunk and kneeled down in front of him. “Good now take this and start sucking, it’ll help you sl**p” he said. I started sucking on his fat 9” cock, but he had more in mind. He grabbed my head and deep throated the fuck out of my mouth. “That’s it bitch, take that cock.” Finally, he pushed me back off his cock and started stroking his cock in my face. His massive load covered my face and oozed down my body and blossoming tits. But just like the guard said, once he was finished I went right to sl**p covered in cum.
Tyrone woke me up the next morning really early. The sun was just starting to come up over the horizon. “We gotta get you up early and start putting together your outfit” Tyrone said. The pageant started at noon, but all participants were supposed to be ready by 10:30. We had 3 and ½ hours to get ready. Tyrone told me to get my makeup ready as he had to leave and get a few things. So while he left I sat in front of the mirror and went to work. I put on some ruby red lipstick, some eyeliner, and some more makeup to make me a little more feminine like. My hair had grown out so much during my 7 months here, that a wig wasn’t even necessary, Tyrone said that would be a big plus. When Tyrone came back in the room he was carrying a bunch of outfits. After looking through the lingerie, we decided to go with a bride theme. I put on these white silk stockings, a white/ivory corset, these very lacy white panties, and a matching white garter belt. Tyrone even had me wear one of those leg garters that one of the men would pull off me. I thought I looked very sexy. Apparently Tyrone did too, he kept saying off if I didn’t have to be ready for the pageant in 20 minutes, he would throw me on the bed and fuck the shit out of me.
At 10:30 I was e****ted by one of the guards and into the back of the kitchen where I saw the other participants waiting around for instruction. A few more ‘gurls’ arrived after me and then the guards told us to be patient as they would be right back. When the guards came back they were carrying 15 differently sized butt plugs. Each sizing from 1” to 15”. This would be how they determined the order. They randomly drew each of our names out of a hat and told us our position. If you were first, you’d take the 1” butt plug up your ass for the final hour as you were gonna be the first up. If you were last you’d have to take the 15” butt plug as you would have to wait the longest amount of time. We all grew eager, some of wanted to be first so we would take the smaller plugs. But others, like me didn’t want to be first because we knew that’s when the inmates would be the roughest. After the first 5 names were called, I was still left standing. Another 5 names were drawn and I was still standing with 4 other gurls. Finally my name was called as number 11. I now had to sit on the 11” butt plug for the remaining hour. Which wasn’t too bad considering Tyrone’s cock was 12 inches. At noon we could all hear the inmates roaring in the kitchen and music start to play. Round 1 was about to begin.
Round 1 was the appearance round. The guards led us in one by one and let the inmates get a look at us. Some of the more veteran inmates would act as judges. When I was called up I could hear the inmates start to pound the ground. I could tell they wanted me, but that wasn’t the contest. The judges had their look at me and even grabbed my ass and felt my tits. I left feeling pleased, and knowing I would advance. I didn’t grab the highest score, that honor went to Stacy who had previously been Stan, one of the first men I met here who totally came off to me as hetero, guess not anymore. Anyways, I scored a 46/50 and advanced to Round 2. However, the 5 lowest scoring gurls didn’t get to advance and instead were punished. They were sent to the guard shack where the rest of the guards fucked the hell out of them. Boy was I glad not to be a part of that. Round 2 was now going to begin.
Round 2 was a bit more involving. All 10 of us were brought out at the same time. The guard told us all to get on our knees and open our mouths. Another guard named Joe Henson, or Big Joe, walked on the stage. I was now 7th in line since the 5 other gurls had been knocked out. Big Joe walked down the stage getting a look at each of us. Once he was finished he resumed back to the 1st gurl and told her to unbutton his pants and get his dick hard with her hands. He looked like he had a 9” cock from where I was, but once he was fully erect I could see it in all of its 16 inches. “My gosh” I thought, “that’s the biggest cock I’ve ever seen.” There were a couple parts to this round 1: how deep we could take his cock, 2: how long we could hold it, and 3: could we get him to cum. If Big Joe didn’t get to cum each one of us would be punished by Big Joe himself. If we were able to get Big Joe to cum then we would automatically advance to Round 3. The 3 gurls with the lowest scores would not make it to Round 3. We were each given 1 minute to see how far and how long we could take his cock. The 1st gurl only took 8” and didn’t hold it long. When Joe got to gurl number 6 he was looking frustrated. He wanted to cum so bad, and you could see that in his eyes with each passing minute. Gurl number 5 almost had him, but her time expired. Gurl number 6 swallowed Joe’s cock taking an impressive 13” down her throat and held it there for :47 seconds. But no cum for Joe. Next up was me. He waved his cock in front of my face and told me to open wide. I gobbled his massive cock only taking 12” but holding it for :54 seconds, and then to my surprise Joe grunted. He was playing with my blossoming tits while I sucked his cock and when I heard him grunt he grabbed the back of my head and f***ed me down another 2 inches of his cock before he let out a huge moan. I shivered and started to tear up with 14 inches of his cock down my throat and then it happened. I could feel his cum shooting right down my throat and into my belly. And as much as he tried to keep me on, the f***e of his cum shooting was too much and his cock shot out of my mouth and the remainder of his cum went flying all over my body, mostly on my face. Big Joe sighed with relief. He patted my head and said, “Good gurl.” He then got hard again almost instantly and moved on the next. I now knew I was safe and headed to Round 3. The 3 unlucky gurls who finished last in the round now had to be punished. They would have to serve as Big Joe’s servant for the next month. The other gurls and I felt so relieved we wouldn’t be serving Joe as a servant, that man needed constant attention on his cock. Round 3 was now upon us.
Round 3 was a bit more challenging. The inmates who had trained us gurls were now onstage. I saw Tyrone standing there looking pleased. Each one of us would be assigned an inmate and we were to fuck them. The 5 of us who made their inmate cum the fastest would move on to Round 4. But each of the trainers wanted their gurls to win, because you see none of us were assigned to our inmate. I was assigned to Stacy’s inmate and a gurl named Candy, formerly Carl, got Tyrone. I knew Tyrone wouldn’t cum to easily, so I had a good shot. Each one of the inmates laid down on their back and we were to ride their cocks until we could get them to pop in our asses. The guard rang the starting bell and we were off. Stacy’s inmate, Larry, only had a 8” cock so I knew it would only be a matter of time. After 1:21 the first guy popped. Which must have been enough release for Larry who popped his load into my ass only :4 seconds later. After another :11 seconds another guy popped his load, and then after another :16 seconds I heard Tyrone pop his load into Candy. I actually felt a bit jealous knowing somebody else made Tyrone cum. But I had to stay focused. After a close finished, the final inmate popped his load just seconds before another inmate. The 2 losing gurls now had to be punished. They were taken by a group of inmates and fucked savagely while the rest of the pageant went on.
It was now time for round 4. And we came back to the stage, 20 inmates were standing around. Each of them would be randomly selected to one of us gurls until we each had 4 inmates. Our goal was simple, get the guys to cum. My inmates were well rounded. They ranged from 9 inches to 13 inches. No problem I thought. Once the starting bell rang, we all got to work. I had laid one of the inmates down and rode his cock while I sucked another and stroked the other 2. It was a sensational feeling. The guy whose cock I was sucking spurted first. But he wasn’t the first inmate to cum. Stacy had that honor, obviously she was going to be my stiffest competition. I took another cock in my mouth and started sucking away. After a few minutes, I was down to just one guy. Stacy had already claimed her spot in the final round and 2 of the other gurls still had two cocks. I rode my final cock furiously trying to get him to cum, but he wasn’t gonna pop. Meanwhile another one of the gurls somehow managed to finish off both her 2 inmates and move on. There was now just one spot left. The other gurl who still had 2 cocks left wasn’t gonna finish anytime soon, she was struggling and getting tired. So it was down to just me and Candy. Candy was on all fours as her inmate fucked her ferociously, and I was still riding my guy. But I knew I wouldn’t win that way, so I got up and started sucking his cock with a passion. I could hear Candy moaning, thinking “uh-oh” so I went harder and faster. Finally! I could feel my inmates cock start to fill up and before I knew it, he was cumming deep inside my mouth. I was declared the winner. Candy, however, wasn’t so lucky. Even with the Round finished Candy’s inmate still wanted to cum. Angry that he had lost (even though it wasn’t about him), he felt pissed off and really started to pound Candy’s ass. Everyone felt sorry for her as this guy just kept on going. The guards did nothing about it except laugh. Finally he came and pushed Candy down, cum leaking from her aching ass. The guards picked her up and walked her and the other gurl who failed the round to their punishment. They were to be the personal shower cleaners. They had to spend 10 hours each day in the shower area and offer each guy a blowjob or a fuck. Every inmate took full advantage of them. But now it was time for the final round.
In the back stood Stacy, myself, and another gurl named Tara, formerly Tyler. We knew this was it. As we prepared for the final round we could hear a bunch of commotion, we tried to get a look but couldn’t see. Finally we were called up and e****ted by the guards. On the stage now stood 30 inmates, many of which had been in the audience the entire time. Each of us was suck the cock of 10 inmates and get them to blow their loads in our mouths. There was two criteria to this round number 1 being how fast we could get all 10 guys to blow their load and number 2 being how much cum we swallowed. Any cum left on the floor would be added up and deducted from our score. Once the bell rang we had at it. Some of the guys just relaxed and let us do our thing, others were more serious. They would grab our heads and fuck our mouths. I let it happen because it was less work for me, but Tara couldn’t take it. She was gagging and crying almost the entire time. It was a close race between Stacy and I. Each time I got a guy to cum in my mouth she was already moving on to the next. We came down to our 7th guys, and me and Stacy were neck-and-neck. We both got our 7th guy to cum and moved on to the 8th. I felt so entranced watching Stacy suck cock, her thick pink lips wrapped around that cock. It got me even hotter and I started to suck with more passion. Stacy noticed my ruby lips wrapped around the cock of my inmate and was suddenly turned on just as much as I was. It was almost like watching the whole thing in slow-motion. I watched as she pumped her cock dry and the cum shooting down her throat just as she watched me get cum shot into my mouth. When me and Stacy came to our final guy, Tara was just ending her 7th. We pumped hard, trying to get our final guy to cum, but it was Stacy who got hers to cum first. I finished just seconds after. Once Tara finished her task, it was now up to the judges to collect any sperm that accumulated on the floor. It was a difficult contest to measure since one inmate might have more or less cum to produce in our mouths, but the judges tested how much was left on the floor. Now while Stacy may have finished first, it was determined that I was the one who didn’t drop as much cum. The judges would have to make a decision. Tara obviously cumming in 3rd. Her punishment would be to be tied up in the dungeon, as we called it, and be the plaything for everyone. She wouldn’t be fucked at all, but she would be suspended where each inmate would cum in to the room and jerk-off their cocks and cum on Tara. Meanwhile, Stacy and I awaited the results. And when we came back to the stage the judges gave their scores. Stacy scored a 48/50. And when they read my scores I was stunned. 9,10,10,9,10 were my scores, putting me at 48/50. We were tied. Which meant there had to be a tie-breaker. The judges snickered.
They knew what to do if a tie-breaker happened, we and some of the inmates didn’t. The guards left and came back with one of the biggest black men I had ever seen. He was extremely buff and extremely huge. “Ladies, this here is who we refer to as Massive Shawn” one of the guards said. This guy was one of the worst guys in prison. He was never let out of his cell because he was too violent. He had rapped and killed some 40 men and women across the states and was finally sentenced to life in prison. Now he was standing before us. “The tie-breaker is simple, the first sissy to get Massive Shawn here to cum, wins” the guard said. And with that they let Shawn loose. He came behind us, ripped off our clothes and started feeling us. He started with Stacy. He pushed her down on her knees and told her to start sucking his cock, which by the way just happened to by 18 inches of pure man-meat. Once he was done with Stacy, he came over to me. He pushed me down on all fours and told me to arch my back. I presented my ass to him just as Tyrone has taught me. Shawn grinned. He slowly started entering my ass. He parked two inches of his cock in my ass and then stopped and moaned. He was enjoying the tight feeling of sissy ass. He then lost control. He plunged the rest of his cock deep in my ass. I screamed as all 18 inches penetrated my ass. The pain was immense. Shawn just laughed, and took my pain as a sign to go faster. He fucked my ass hard and long. But finally he stopped. He extracted his massive cock from my ass and went back to Stacy. He told her to do the same, but instead of starting slow, he went full throttle into Stacy’s ass. After 5 minutes, he let out a groan. I knew he was about to blow. Stacy was in serious pain. Her entire body lay flat on the ground, tears running down her cheeks. Shawn now grunted. “Here it cums bitch” Massive Shawn said, “looks like you gonna be a winna.” And with that Shawn released. His cum filling up Stacy’s ass. Shawn then grabbed his cock and called me over. He pulled out of Stacy, and with his cock in his hand he pointed it at my face and finished cumming. “Thought you might like some too” he said. Stacy still laid motionless, but nonetheless she was declared the winner. She was now given a choice, she could stay a sissy and keep fucking men or she could go back to being a man and fuck all the other sissies. Stacy took the second option. Stacy, once again Stan, resumed his life as a man and began fucking the other sissy inmates. Once Stacy was declared the winner, it was time for my punishment. “And for finishing in 2nd place, Sissy Katrina here will now be f***ed to prostitute her body to every inmate in here. Including r****g Shawn whom she must fuck at least 3 times” the guard called, “And this begins now!”
So there I remained. While Stan was given his mandom back and a year off his sentence, I was going around as Katrina fucking every cock I saw in the place. Shawn actually proved to be a sensitive lover. We didn’t fuck 3 times, we fucked 8 times. God how I loved the feeling of the 18” black cock grinding my ass. I still remained with Tyrone for another 3 years, but once he went on probation I offered to be Shawn’s roommate. I still entered the Pageant every six months it was held, but I never won. Nor did I ever want to win. After all this time as a sissy slut, how could I ever go back to being a straight man. It just wasn’t in the cards anymore. I spent the rest of my 10 year sentence behind bars and fucking just about every cock available. Once I was let out, I couldn’t stand to be away anymore. So I committed another crime. Which sent my back to prison for another 12 years. It was completely worth it :)
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