Prison Makes Me a Sissy Pt. 03

The guard returned and took me back to my cell. Hercules wasn't there and it felt so empty. I didn't like being all alone like that, and craved my big strong muscleman who cared for me. It was unsettling waiting for Hercules because I worried that he might have been hurt. As I contemplate that possibility, I became more certain that I had already fallen in love with him. Not only that, my body still felt sticky and damp from the massive wad Blake gave me just an hour earlier, and I knew I was falling in love with him as well. I desperately needed both of them.

The guard brought our dinner and Hercules still hadn't returned yet. I got more and more nervous. I went over to pick up the trays and the guard could see that I was crying. After handing me the trays he said, "Hey, don't worry, he is just fine and wanted me to tell you he will be back soon."

I felt so relieved and wiping tears from my face I thanked the guard, and he responded, "No worries, we like to keep Hercules happy and I know he can't wait to be with you again."

Wow, my heart was full of love when I heard that. I couldn't wait to see him again and the thought of sucking him off overwhelmed me. Then the guard added...

"Oh man, Hercules really destroyed that guy today, worked him over like you wouldn't believe. His fists were like sledge hammers breaking the guy apart. That guy was an asshole anyway and stabbed a lot of prisoners. But now he'll never be the same, physically or mentally."

I thought about how Hercules could crush someone with his fists and it was sort of a turn-on. It would probably be way too brutal and disturbing for me to watch. I ate my dinner but after a few bites I couldn't eat anymore because Blake's massive wad filled me up so much, and I knew Hercules would want to feed me again too.

It seemed like I was already transitioning to a diet of muscleman cum and wouldn't be eating much regular food from here on out. Between Hercules and Blake I would be more nourished than ever. I looked forward to deriving health benefits from their potent sperm as well as getting a more feminine and sexy little body. My skin already glowed from rubbing their sperm all over it for them, and it made me smell so slutty too.

Finally, I heard footsteps from down the hall and Hercules arrived. He was just wearing his workout shorts. I rushed to him and held him tight. I was still wearing the little two-piece outfit and it was obvious he especially liked it. We held each other like we hadn't been intimate for weeks. He cradled my head into his massive and hairy chest. Smelling his manly body again was so comforting and so sexy too. I noticed he smelled even more manly and must have really exerted himself working over that poor guy...

"Oh Hercules, I worried something happened to you. Do you want to talk about what happened?"

"I'm not sure Inshould expose you to that side of my life. It might be too violent for a little sissy like you."

"You must have worked hard on him because you smell very strong and musky right now."

I couldn't help but sniff his stud body, my little penis hardened as I did. His enormous cock expanded in his stinky shorts, overwhelming the fabric, and almost busting through it. He picked me up and carried me to his bed. He gently sat me on the bed, and standing in front of me, removed his shorts.

I stared at the exposed monster cock as he lightly pumped it with his hand, showing off its unreal size for me. It made me moan and whimper, and hearing that he said...

"I guess my manly smell is very powerful now. Is it too much for you Michael?

"No, it's not too much. But it is very manly and musky. The more I'm exposed to it the more it turns me on. Then when you show me how massive your cock is, and I taste it, I go crazy with lust and want your sperm."

Hercules stepped closer and said, "Here, why don't you taste and smell it as much as you want."

I lost myself when all the ultra-manly stimulation took me to a super-slutty state of mind.

He could see my loss of control and said, "Oh fuck, you're so slutty and make me feel like the biggest stud in the world..... Is Blake real manly too?"

I didn't expect that question, and I looked up at him but didn't say anything. Finally, he said, "Don't worry, I'm not jealous. I like knowing you want other big cocks and then come back to me afterwards for even more. It's so hot."

"Well, you were right Hercules. I liked being with the three big musclemen. I really did. They were all so big and muscular. I liked their smooth bodybuilder muscles. They all smelled very manly too. But Blake was the hottest of the three. His smooth giant muscles rivaled your pure size and his scent was almost as manly and powerful as yours... Boy, you sure smell powerful right now."

"I figured you'd like Blake. Next to me he is the biggest stud here, and that includes his massive cock. I already heard that he is very pleased with you."

I kept looking at his giant cock as he continued to lightly stroke it for my pleasure, and said...

"Hercules, the other two big musclemen fucked me, both of them. I liked that too....But they were so big it hurt."

"I'm so glad you let them breed you like that. I heard you did well for the first time. It will get better as they break you in. Those two have pretty big cocks."

"Break me in for what?"

"For me, and for Blake too."

"Oh Hercules, I hope someday that you and Blake can mount me."

"Those two studs will pump you until your ass is completely pounded out. They know what they're doing. We just need to give it some time for your little ass to adjust and develope.... I heard those two guards can't wait to see you again."

"Mmmmmmmm, the thought of taking them again, and especially someday being able to take you and Blake is so hot. I mean, look at this giant thing."

"Here, why don't you suck on it."

I was taking in Hercules manliness and responded. "Oh yeah, let me suck on it....Gosh, it's so musky."

"Enjoy it now Michael, take your time."

With that Hercules put his right hand on the back of my head and pushed my face into his big heavy balls. I rubbed my little turned up nose on them and whimpered as the utter manliness overpowered my senses. They seemed even more plump than normal and I assumed the excitement of busting up the other prisoner triggered higher testosterone surges and subsequent production of large amounts of sperm.....

"Oh Hercules, your big balls are so heavy this morning and must be packed with so much sperm for me."

His massive cock and balls had a manly oily coating all over them his man oil got on my face as Hercules rubbed all that ultra-musky cock and ball meat on me...

"That's it Micheal go for it, take it all in.... Look how your face is getting oily and shinny from my ripe cock and balls."

I had a one-track mind sexually, and emotionally I was in love. There was such a massive amount of both cock and ball meat that I forgot about everything and my mind got singularly focused on getting Hercules off as powerfully as possible.

As I worked on him I would briefly stop and ask about what he did to the prisoner...

"Did you get big and hard when you busted up that bad guy?"

"Yes, especially towards the end when he was defenseless and taking such powerful shots. I got so very big and hard."

"Mmmmmmmm, that sounds so hot. Did it make you want to keep beating him up with your fists?"

"Yeah, I kept going and I liked how I made him whimper in pain and beg me to stop."

As Hercules talked about it he got more and more horny. His enormous cock pulsed and leaked and twitched. It was just so big and manly.

I worked on him sensuously and in doing so communicated my love for him. At one point he tenderly held my head and said...

"Michael, no other sissy has ever understood how I get so turned on when I destroy bad guys, and I love how you like hearing about it."

"Hercules, I do like hearing about it... Look how hard my little penis is when you tell me. You can talk to me about it anytime you want."

"I want to tell you Michael and I like how it excites you."

At that point he pushed his giant cock head into my mouth and couldn't respond. He kept stretching and pumping open my little mouth so I moaned long and loud in acknowledgment of his need to tell me. I felt closer to him as I blew him lovingly.

When he did cum, he unloaded very hard and fed me so much jizz. I rubbed even more on my smooth little body. I gave him the sluttiest cum show ever, moaning as I massaged big gobs of sperm into my smooth white skin, especially all over my hard perky nipples. I pinched both cum covered nipples as I looked up at him like a sexy little slut.

Afterwards we collapsed on his bunk, and I rested on his big muscle body. I had that wonderful feeling of love for him and felt safe and secure. His wad was so thick, rich, and creamy. Its potency was unmatched. I rubbed my little nose into his big chest and through his chest hair. He smelled beyond manly now.

He loved how I sniffed all over his chest and he flexed his muscles for me. I was in heaven and he knew it. The next thing I knew the nightly lights-out buzzer sounded and we settled in for the night. Before we dozed off to sleep I whispered in his ear...

"I love you so much. You are such a manly big-cocked stud and I'll do anything for you."

The next thing I knew it was morning and we woke up, and oh my, his cock was so big and hard. I pulled back the covers to fully expose it and also saw two super-big swollen balls. He needed to feed me my breakfast, and boy did he. This time I was really hungry and ended up consuming almost all of the massive load of multiple thick ropes of ultra-potent sperm. I even rubbed some on my face like it was a moisturizer.

A few minutes later breakfast trays were delivered and Hercules ended up eating everything on both trays because I was just so full. After breakfast Hercules started working out with the weights and I watched him from the bunk. I loved watching him lift weights. As I enjoyed the show another guard came and motioned Hercules over to the bars. They talked and Hercules came to me and said it was time for me to go to the guard's gym again...

"Go enjoy yourself with the bodybuilders and I'll see you back here in a couple of hours. I'll be working out hard and ready for you later."

I did as he told me and this time I wore my little silk robe for them. The guard escorted me to the gym, opened the door to let me in and locked it like last time. I could see the two big studs that fucked me last time, but Blake was not there.

They explained that Blake was at a conference and would be back later in the week. They also said Blake gave them instructions to continue to break me in. My ass tingled slightly in anticipation of that. They both looked so big and muscular, and they already were all pumped up and sweaty. They wore the same little posing shorts that emphasized their big heavy bulges. Their manly smell filled the gym and hit me simultaneously and combined into a powerful muscleman scent. I stared lustfully at their smooth muscular bodies. They looked more heavily muscled and thicker than last time, and one said...

"Do you want to enjoy our bodies before we breed you? After all, we've been working out hard for a while waiting for you."

I wanted to worship their muscles so bad that I immediately went to them and alternating, I rubbed their big hard bodies feeling up their massive muscles, then rubbed my face and nose on them. They both smelled really strong and I was getting more and more turned on, which was the point. They were priming me for a good stretching and pounding.

Then they removed their little shorts to show me their big hard cocks. I got on my knees and spent 10 minutes sucking and licking them, alternating back and forth. They were both so musky and I wanted them to mount me. Their pre-cum tasted so good and there was so much of it.

Once they were fully primed by my oral work they removed my sexy silk robe, moved me over to a counter top, and raised my right leg onto the counter. My left foot was on the floor supporting me. My ass was wide open and they moved my hips slightly to create the best target for their big hard cocks. Both rubbed their hands all over my little body and kept complimenting me about how sexy I was.

They informed me that they were going to continue to pound me open and break me in, but more diligently this time. Then they instructed...

"Now don't touch that little hard penis of yours no matter how bad you want too. If you cum, it has to be from our big cocks methodically pumping you. You need to learn to cum from your ass from now on."

"I want to cum from my ass and I want both your big cocks inside me."

With that the first guard stepped up behind me and inspected my ass closely, saying...

"Look Joe, he's still a little swollen and opened up from last time. Remember how fucking tight that little thing used to be? And look, it's really moist with his natural ass lube. He is already transitioning."

"Fuck yeah, you're right Jim. Let's take advantage of this and get him to the next level... Look, he's arching and spreading out his leg. He wants it bad."

I did want it bad. All their talk was making me crave a big cock pounding. I realized that I did feel moist down there. My ass instinctively knew what was coming and started preparing for the inevitable.

Joe started first and within 5 minutes was balls deep and I was moaning uncontrollably, and I heard him say...

"God damn, this is the best ass I've ever had. He's milking me with it. Fuck!"

Then Jim said, "Let me work that too."

I felt Joe pull and and then Jim, with his even fatter cock mounted me, and two minutes later he was balls deep and pumping me with long slow strokes. They traded off like that for what was probably 45 minutes, encouraging each other...

"Oh fuck, pound out that ass Jim... Just look what you're doing to it."

"Yeah, it's swelling up and look Joe, the lips are all red now."

"Your drilling him out Jim, you really are."

Any pain had ceased soon after they first mounted me, and now it was all pleasure like I'd never experienced. It was so much better than the previous time, and I was whimpering like a slut. I could literally feel my ass expand more and more and heard Jim say...

"Look at this, he's a natural and a genetic freak. No one else could take this big cock pounding so soon. Blake will be pleased."

I reached down to touch my penis and Joe slapped my hand away...

"Remember, no hands, develop your ass orgasm like we said."

Then Jim suggested that he lay back on the weight bench and have me sit on his big fat cook to see if I could bounce on it. Joe helped me off the counter as Jim positioned himself on the weight bench. Joe helped me straddle Jim's waist and I slowly impaled myself on his fat cock.

I soon realized I liked being on top because I could show off my little body and better control the depth and pace. In addition, I could worship Jim's muscles as he flexed for me. I bent down and rubbed my face and nose on his chest and arms as he flexed so big and hard. I even rubbed my nose in his muscular arm pits as he flexed. It had a profound affect on Jim as he grunted and moaned. It made me feel so sexy. I loved his stud smell.

His smelly body was triggering feelings of pre-orgasm and I buried my face in his armpit for more manly scent. Joe moved to the side of us and pulled my head into his crotch. I started sucking his big cock while bouncing on Jim's meat. Joe's cock had been pounding my ass a few minutes earlier, and I could taste it on him. It seemed to add to my excitement and as Jim watched me clean Joe's cock he approached orgasm. I also felt my own orgasm coming and both Jim and Joe encouraged it...

"Let your ass come, just let it, don't hold back."

My little body tensed up, I put both my arms above my head to show off a sexy pose for them. I continued to bounce on Jim and taste my ass on Joe's big cock.

Then it happened: A powerful orgasmic surge from my asshole hit me like nothing I'd ever experienced and my little hard cock started spurting clear gel-like cum onto Jim's stomach. Not only that, but I could feel my ass intensely flutter and pulse on Jim's big fat cock. Jim grunted loudly and started coming deep in my ass, his eyes rolling back in his head. Then I felt ropes of wad slamming against the side of my face and all over my girly body. My arms were still over my head and I felt a massive rope explode into my under arms and across my chest. Joe was unloading all over me.

I collapsed on Jim and kept his semi-hard cock inside my ass, and he said...

"Oh my god, you're fucking ass was like a hydraulic pump on my big cock, pulsing on it so powerfully."

Joe eventually helped me off Jim and they explained that would have to be all for today. They also told me I was well ahead of schedule.

They were breaking me in for giant cock, Blake, and Hercules specifically. For the first time I felt confident that I'd get there soon. I also understood that my ass orgasm was much more powerful and fulfilling than my penis orgasm. I thought about the kind of ass orgasm Blake and Hercules would facilitate. I couldn't wait!

Both Joe and Jim hugged me, which felt good. Then, as Jim hugged me he kissed me on my cheek tenderly and rubbing both his thumbs on my nipples and I instinctively stuck out my little chest for him, when he said,

"You were amazing, just amazing. I will see you tomorrow."

I hugged him tenderly and said I couldn't wait. At that point I could tell I was getting to him, and as they left I heard Joe tell him...

"Jim, you need to stay business-like here. You're getting very enamored with him, and attached... But I can't blame you."

Over the next week Joe and Jim were relentless, fucking my ass over and over again. Opening me up. Boring me out. My asshole was changing for sure. Not only were they making it much larger and thickening the ass lips, but they were getting it so well conditioned.. I was also lubing up naturally, getting so juicy whenever I thought about being mounted by big cocks.

The problem for them was that they liked it so much that both were getting emotionally involved with me, especially Jim. They both started caressing my little body so tenderly, sucking on my sissy nipples, and kissing me. They couldn't wait to show me their big-muscled up bodies and have me rub, lick, and smell them. Not only that, but they each started fucking me twice per session, which lasted well over an hour. My ass was almost ready for Blake and Hercules.

In the mean time I kept sucking off Hercules and worshiping his body. I was changing physically from the effects of the big cocks pounding my ass, stretching out my lips and mouth, eating so much cum, and massaging so much cum on my little body. Specially, my asshole was opened up and developed, my lips got plumper from sucking such big cock, my jaw joint loosened and I could generate more suction, my body got firmer from consuming the nutritious sperm-based diet, and my skin looked whiter and very moist from constantly rubbing wad all over myself.

I was close to being the perfect sissy for Blake and Hercules......