Prison Makes Me a Sissy Pt. 04

I'd be remiss if I didn't inform you about taking showers with the other prisoners. We did so two days a week. Hercules is always very protective of me. Because of that I felt relatively safe and started sexually teasing the other prisoners. Most were always looking at me like a prime piece of sissy meat.

I always soaped down Hercules body with my little hands and would spend extra time on his giant dirty cock and balls. He would normally get semi-hard and sometimes even rock hard as I soaped him down. Inevitable he would start to engorge and then I would soap up his muscular ass and clean it as well. I'd try to be as sexy as possible for the other prisoner's viewing pleasure. I would use one hand to soap down his giant cock and balls, and with the other hand I'd reach around him to clean his ass. Of course I would moan loud enough so they could hear me even with the noise from the shower nozzles.

Once Hercules was clean he used his big hands to soap down my little sissy body. I loved it, and I loved showing off my girl body as Hercules rubbed his hands all over me. The other prisoner's excitement grew when Hercules soaped up my little ass. He would spend so much time doing it and he would even insert his fat finger and make me whimper for everyone. I could picture all the prisoners going back to their cells to jack themselves off thinking about me. I thought about all the sperm being released in my honor. I became the most desired sissy in the entire prison.

From the very first shower a group of big super-muscular black guys would always come over to use the shower nozzles closest to ours for a front row seat. Hercules always gave them a look that let them know not to try anything. They all had very big black cocks and they liked to show them to me. They made sure to show off their massive ripped up muscles too. Some looked as big as Blake and Hercules. It's obvious they'd love to have me. I liked turning sideways to them and arching my back so they all got 'em a real good look at my smooth little white body and ass. Whenever I did that their big black cocks engorged and thickened. I could tell they worked out an awful lot and I liked looking at them and wondered what it would be like sucking them off after they lifted weights. I was evolving into being more and more slutty.

Joe and Jim, the two guards that were essentially assigned to develop my ass for Blake and Hercules, worked on me many days. They did their job and I fully transitioned into an ass orgasm-based sissy slut. Not only that, but they completely changed the structure of my ass. My hole looked almost muscular now, and it could contract, vibrate, and pulse very powerfully, especially when I sissy orgasm.

Blake started seeing me by himself. He loved the intimacy of our one-on-one encounters. I noticed that he always checked how my ass was progressing and grew more and more excited as my ass showed such impressive development. I blew him as much as I could. There was something about his enormous cock that made it my favorite to suck on. It was a combination of utter size and girth, big perfectly formed and heavy balls that balanced out the enormous cock, and his wonderful super-manly musk scent and taste. Not to mention, his sperm was absolutely delicious.

I loved intensely worshiping Blake's massive muscles and then sucking him off, usually twice, back-to-back, and after that, returning to Hercules and blowing him as much as he needed. Hercules could obviously tell I'd been sucking off Blake, and it added to his ultra-sexual excitement. He could see lots of Blake's sperm on my little body, and I had the strong scent of Blake's muscles and cock on my sissy skin. Sometimes, while Hercules watched, I would get on my knees and using my hand, scoop up any remnants of Blake's sperm and lick it off my fingers. That's when I felt the sluttiest, and Hercules would say...

"My god Michael, you love Blake's sperm so much. I've never seen anything like it."

"Yes, I do love sperm, especially from you and Blake. My little stomach gets so filled up and you two keep feeding me bigger and bigger wads."

By the time I would start sucking on Hercules he was already close to coming from my sexy actions and slutty comments. As I smelled Hercules I thought about Blake's strong scent too. I liked how Blake and Hercules smelled different and unique. Talk about super-musky and manly smelling! I also liked how Blake was shaved so smooth and was so ripped and heavily muscled, and how Hercules was so hairy and thickly muscled all over.

In addition, I looked forward to being with Joe and Jim and their relentless ass focused sex. They did an amazing job training me to orgasm from my increasingly blown-out hole. I loved how they would trade off and methodically pound me out until I came from the impact of their big cocks.

One day while I was blowing Hercules after sucking off Blake several times, I felt my ass start to contract and spasm on its own. Both Blake and now Hercules were very strongly scented that day, with heavy manly musk, and Hercules was oozing so much pre-cum. I was finally losing myself in it all and reached down with my right hand to rub my fluttering asshole. I moved my index finger all around my fully developing hole. My natural lube coated my finger. Hercules watched my self-love and grunted approvingly. My ass was about to take me over the top. As if sensing my impending sissy orgasm, he exploded and fed me a huge wad. Simultaneously I felt my ass orgasm and it sent jolts of pulsing pleasure throughout my little body as Hercules pulled out of my mouth and covered me in layers of dense sperm.

Afterwards, Hercules said, "Micheal, that's the first time you rubbed your ass for me like that. I think it's almost time I try to mount you... Imagine what I will do to that pussy."

I liked how he referred to my "pussy." It had been transformed due to all the big cock pumping and pounding by Joe and Jim. Hercules was right, I think I'm ready to try giant cocks. I suspect Blake feels the same way.

Not only that, now whenever I contracted my sphincter my ass felt more and more powerful. My sexual nerve endings must have grown and expanded throughout my pussy because it became more sensitive than my little penis. My penis seemed to get even smaller now. Everything was shifting from my little dick to my amazing pussy. Both Joe and Jim would comment at how it would grip their big cocks and how powerful pulsing and twitching actions would milk their big cocks whenever they made my ass orgasm. One time Jim said my ass gripped his big cock so hard he couldn't move it.

The next morning I woke up and sucked off Hercules. It became a morning ritual because it was the only thing that would relieve his aching and massive morning wood. I looked forward to this intimate time with Hercules and I always looked forward to eating his sperm and rubbing it all over my skin. Now, every time I sucked him off he would reach down and finger my ass and it would make me cum real hard. It was a wonderful way to start off the day. I recognized that at any point Hercules could try to mount me. It was only a matter of time.

The guards came early this morning and told me I needed to go see Blake at the gym....

"Michael, let's go, Blake is working out and asked for you."

I said good bye to Hercules put on a new red bikini that Blake got me and was taken to the gym. I modeled it for Hercules and hugged him before leaving. I noticed he got big thinking about me being with Blake. That was a good sign and made me feel even sexier. Hercules knew I'd be super-slutty when I returned to him.

I arrived and Blake was the only one there. Boy did he look pumped up from working out extra hard for me. There was no question he wanted to show off his giant, perfectly proportioned, and sexy smooth muscle body. I went right to him and hugged him tight, and rubbed my little nose all over his sweaty chest. What a musky super-stud. He looked down at my bikini-clad body and said...

"I thought you'd look super sexy in that bikini and I'm pleased you wore it for me."

"I feel so slutty in it and I'm glad it turns you on so much."

He was more smelly than the last time and it was obvious he wanted to be as manly as possible for me. I continued rubbing my face and nose all over his smelly chest and sucked on his nipples. His sweat was getting all over me...

"Oh Blake, you taste and smell like such a stud right now."

Then Blake started caressing my little body and kissing my chest as he moved to my nipples, sucking on them hard...

"Blake, can you can tell that I sucked off Hercules this morning when I woke up? Can you smell Hercules musky body and jizz all over me?"

"Your such a little hore Michael. I like his scent on your little sissy body, and it's hot knowing you sucked off Hercules. There's so much dried cum on you, and the smell of his giant cock is on your breath."

"Mmmmmmmmm, I love sucking on you and Hercules. I just love lots of sperm."

Then Blake got more business-like, and said...

"Michael, I think it time."

I knew exactly what he meant and my ass involuntarily started to pulse and was getting moistened with my natural lube at the thought of it. I looked down and lightly stroked his massive hard on, and said...

"This is such a big thick cock, and I want you to mount me with it and pound me out like only you can."

Blake was overwhelmed with the desire to mount me and pushed me down to my knees, saying....

"Here Michael, work on my big hard cock until your ass gets real lubed and juicy for me. Get this thing as big and hard as possible."

Blake was right, the more I enjoyed his massive cock, the juicier my ass got. I could even feel my lube leaking from my ass and down my leg as my asshole relaxed and opened slightly. Blood rushed to it, swelling it up and sexually sensitizing it. I felt so slutty, and my instinct was to touch it but I wanted to save it for Blake. I couldn't wait for him to examine it.

Then he pulled me up and started caressing my little girl-like body with his big strong hands. He was getting super horny now and he kissed me then started kissing my neck and down to my chest, ultimately focusing on my sissy nipples, sucking on each one. As he sucked on them he was smelling me and moaning, and then I asked...

"Don't you think the smell of Hercules is sexy all over me?"

Blake grunted approvingly and kept at it. Then I continued...

"Hercules gets so dirty and manly for me, and then he keeps feeding me lots of jizz and I get cum drunk.... That's when I think about sucking off your massive cock too and feeding on your delicious giant wad."

As Blake continued to enjoy my nipples I pushed my little chest out more and arched my back. Then I reached back and used my index finger to rub my moistened hole. Blake released my nipples to watch me. I moaned and moaned as I continued to finger my ass for him. Then I instinctively removed my finger and raised it to my sissy lips and mouth. Holding it inches from my mouth, I looked up as Blake and slowly lapped my finger as I smacked my lips. It tasted so sexy, and I was driving Blake crazy with lust.

At that point Blake put me on all fours and got behind me. I arched my back for him. Then he finally got a good look at my ass. I anxiously waited for his reaction, holding my slutty arch and wiggling my ass for him...

"Fuck, look at it, all juicy, and look how it's opening up on its own."

Then he started kissing my ass cheeks and smelling my sissy hole. It triggered something in him and he started licking and lapping on my highly developed pussy. He loved my juices!

I arched as much as I could as he ate me out. My ass relaxed open further and continued juicing up from his mouth and in anticipation of his massive cock. Just as his mouth was about to make me cum he stopped and positioned himself to mount me...

"That's the best tasting ass I've ever had... My god, Joe, and Jim were so diligent and pounded you out good. Look how those lips are so developed. Now let's see what it's capable of."

Blake used his big hands to spread out my ass cheeks. I felt a strong stretching and could tell my hole aches for big cock. It felt so sexy. Then I could feel his massive cock head push up against it and little by little Blake pushed harder on my ass. Surprisingly, his big head popped inside me with hardly any pain and after pausing a few seconds Blake slowly began to bury more cock into my ass. Joe and Jim were very big, but this was a different level. The fullness I felt was astounding. It hurt but it was also pleasurable. Blake was on a mission and methodically pumped more and more giant cock into me...

"Michael, this is unreal. You're fully developed and seemingly fully prepared for massive cock. I'm gonna really pound you out now."

"Oh Blake, you're just so fucking big. Go ahead, pounds out my ass."

He was penetrating me more and more with each powerful pump. Any resistance he encountered was breached easily after several focused pumps of his amazing cock. He was methodically taking my ass to another level.

My ass gave way from the onslaught. The tremendous pressure and stretching from his super-big and thick cock was the most sexual experience of my life. Blake was taking me towards a monstrous orgasm. I could feel it coming like a freight train. His massive cock totally owned my ass now and he didn't let up.

As my impending orgasm mounted onwards I could feel my ass pulsing on Blake's giant cock and I could hear him grunt louder and feel him rotate his hips at the end of each pump to bury as much cock into my ass as possible. His big heavy balls smashed into me.

He pounded me past the point of no return and my ass began to flutter powerfully on his monster cock. At that point I got so emotional that I blurted out...

"I love you so much Blake."

Then I came harder than I ever thought was even possible. My ass generated wave after wave of orgasmic pleasure from head to toe. Simultaneously, Blake exploded with such force that his massive cock literally lifted me off the floor as he unloaded. Once, my powerful ass pulsing relented I could feel his massive cock throbbing inside me. I never felt so feminine, submissive, and sexual as he continued to unload giant ropes of semen that literally filled up my ass.

Blake finally pulled out of me and a torrent of wad followed out and splashed onto the ground. He collapsed on the floor and I collapsed onto him. He was all smelly and sweaty and I loved it. I nestled my head onto his smooth massive chest. As we basked in the glory of what just happened I felt and need to tell him again...

"Blake... I love you so much."

He held me very tight but seemed cautious about divulging his feelings, so I said...

"Blake, you don't have to say anything. I understand. I just want you to know how I feel, about you."

I felt his hug get stronger, as if to let me know he does care deeply about me. That was good enough to set my heart a flutter.

He massive cock was still mostly hard, and it would flop around and hit me as I rested on his big body. I could smell Blake's manly body, but I could also smell my ass on his massive dick.

As if to demonstrate my love for him, I moved down his body and licked my juices off his cock. It tasted so erotic and he hardened as I tongued him, and he said...

"You are the sluttiest and sexiest sissy I've ever had. We are going to be seeing an awful lot of each other. Now suck me off."

Once I finished licking his rock hard cock clean, I focused on sucking it off. I went crazy on it and craved sperm. Blake was holding my head where he wanted it and would periodically move my mouth down to his big heavily scented balls. I loved that so much, and whimpered at the powerful manliness I experienced.

At that point I rotated myself around so he could view my ass. I wanted him to see what he did to it. I knew it was all blow out and swollen, and I knew it was leaking sperm almost continuously. When my ass was positioned near his head and while still licking and smelling his massive balls, I arched so he could see how he blew me open. Blake moaned in a deep man voice, and then said...

"Fuck me, I really drilled you out... So swollen, so pink, so stretched out, and so juiced up with sperm."

"Blake, does that make you feel like a big stud? ...Seeing what your massive cook is capable of doing to ass."

"Fuck yeah, it makes me feel like Superman. Just look at what I did to it!"

Then, I wiggled my ass, and said...

"Yes, you've changed everything now Blake, you really have."

Blake moved my mouth to the head of his cock and I knew he wanted me to make him cum. I was hungry and wanted wad. I sucked and sucked until he convulsed his entire body and shot rope after rope of cum into my mouth and then all over me.

There was no question, Blake wanted me to return to Hercules with his stud scent and sperm all over me. It was as if they both wanted to signal each other what they did to me. I couldn't wait to kiss Hercules as soon as I returned to him...