Prison Makes Me a Sissy Pt. 01

Unfortunately I got involved in drugs and got caught selling some to my friends. That's how I ended up in prison on a five-year sentence. My first day was scary and intimidating. I'm a small skinny guy and still only 19 years old. I have a very white complexion and I look pretty feminine.

My friends would always kid me that I look "so cute." I'd been mistaken as a girl at first glance, many times. I have big blue eyes, full lips, and a little nose that's slightly turned up. Adding to my feminine appearance was the fact that I was pure blonde and had almost no body hair. What little body hair I had was so fine and light in color that it scarcely showed up. It didn't help that I had a little penis and tiny testicles. Whenever I showered at school after gym class I noticed guys liked to look at my little smooth body. Understanding how feminine I looked really concerned me as I entered the prison grounds.

I went through the mechanics of checking into prison and being assigned a cell. I could see that two prison guards looked concerned. I overheard one say, "This little boy is gonna get used and abused if we don't do something."

Then they approached another guard who appeared to be their superior, and talked for about five minutes while I waited for the next step. At that point the two guards came over and said they were going to take me to a cell and my new roommate...

"Look, your roommate might appear scary but if he likes you there's nothing he won't do to protect you in here. Just be patient and nice to him. Got it?"

Now I was literally shaking and replied, "Yes sir."

We went past numerous cells and guys were whistling and calling me bitch and other dirty things. They scared me to death. Then we went down a dark hallway and I could see there was a cell at the very end of it. That's where we were headed.

When we got there I could see it was a much larger cells than the ones we passed. It actually included a lot of what looked like old weight training equipment and lots of very heavy weights. Cell bars went across a 10-foot section that integrated the door. The rest of the walls were solid concrete, so it definitely wasn't like a normal cell. I guessed the cell was about 600 square feet.

There was a giant muscular guy in the back doing the bench press with an extraordinary amount of weight. He grunted as he pumped up a barbell numerous times and it must have had well over 400 pounds on it. The man looked like a giant and as he completed about 12 repetitions he stood up, and looked directly at us. He was the most imposing figure I'd ever seen.

One of the guards said, "Hercules, we have a roommate for you. His name is Michael. Don't let anything happen to him....Pretty please."

Hercules didn't say a word and went back to lifting weights. The other guard said, "This is a very good sign, he didn't say anything. Your in." Then the guards left and I was startled from the loud metalic sound of the cell door shutting.

Hercules was heavily muscled all over his body. Definitely not like those body builders who are so symmetrical. He had the biggest muscles I'd ever seen and there was no proportion or symmetry at all, only enormous muscle size and thickness. He wasn't into super-low body fat either, and just wanted to be as big and strong as possible. Unlike shaved and smooth body builders, he was relatively hairy, like on his big chest. From what I could see he looked about 40 years old.

I had a small bag of things the guards gave me and I could see there were two bunks, and one was unused, so I asked...

"May I put my stuff on this bunk Sir?"

He looked up from across the cell, which was probably 20-feet long, and said...

"That's fine."

I relaxed a little and sat on my bunk, which didn't seem too uncomfortable. I looked around and could only see one toilet and sink in the corner. This was going to be awkward!

I was scared and nervous but tried to strike up a conversation...

"Hercules, I'm so glad to be your roommate. I'm very frightened around here."

"Look, they told me to protect you and no one will ever hurt you... Understand?"

"Hercules, what about you? Will you hurt me?"

"No. I would never hurt a defenseless little guy like you....Never."

For some reason I felt I could trust him. It was like he had a code he stuck too and had some sort of pride about it. But only time would tell. He was in the back of the cell at least 20 feet away from me. He was just wearing fairly small yellow workout shorts and didn't even wear any shoes. He looked all sweaty and pumped up from working out so hard. It was also warm in the cell.

Finally he came over to my side of the cell and stood over the toilet to pee. His massive back was to me. He looked maybe 6 feet 3 inches, and must have weighed 300 solid pounds of pure, dense muscle. From eight feet behind him I watched as he pulled down the front of his shorts and reached in to pull out his cock. As he pulled it out I got a glimpse of some of it when it briefly flopped out from the side of his hip. It shocked me because what I saw looked like the fat end of a very thick baseball bat. I was stunned.

He finished peeing and stuffed the giant cock back into his shorts and turned to go to his bunk. I could clearly see a large mass showing in the front of his shorts. I'm not very big at all and I thought this is going to get real embarrassing if he sees my little cock. I wanted to try and get to know him, and asked...

"Is your name really Hercules?"

"It's just my nickname, everyone calls me that, even the warden."

He also told me the guards would bring our meals to our cell so we don't have to go out in the general population much. Mainly just to take a shower and go to the yard for some fresh air. I immediately worried about taking a shower with a lot of men. He could see I was concerned and said...

"I already told you I would protect you. Don't worry. And besides we only take a shower every third or fourth day, depending on their schedule. Don't worry."

At that point a guard arrived with two trays of food. We sat on our respective bunks and ate. I was starving and actually thought it tasted pretty good. Then I noticed Hercules had a large glass of something thick. He said it was a protein smoothie for his weight training. He also said we get much better food than the other prisoners. I kept wondering what the punch line was.... Why are we getting such special treatment?

After dinner the guards came to retrieve our trays and they also gave me a bag of what appeared to be clothing. After they left I opened it up and there was a little silk robe, small stretchy form-fitting shorts that looked like they would hardly cover my ass, and a sleeveless form-fitting top that only would cover my chest and shoulders.

Hercules was paying close attention as I took the clothing out of the bag, holding up each piece, and he asked...

"Why don't you put on that little silk robe so you can relax and get comfortable."

"Oh, I don't think I should right now."

"It's not a question. I'm not asking."

I was frightened and felt I had no choice so I got up and turning my back to Hercules, took off my orange prison overalls. I could feel his eyes all over me as I slipped off my clothing. He saw the back of my little nude body and I quickly slipped on the silk robe. It was pink and actually felt good on my pale white skin. The robe was so short that when I sat back down on my bunk I had to pull down on the bottom to avoid exposing my butt and crotch. After a long silence Hercules said...

"You look beautiful in that little robe."

"Thanks Hercules.... I guess. I feel sort of silly like this."

"No, it's not silly. It shows off your nice firm body. The pink looks great on you're glowing white skin."

"Oh, I guess I'm glowing because I've been sweating. Probably, from nerves, and it's sort of hot in here too."

"Michael, I like how your smooth, pure white skin glows in the heat."

It was the first time he called me by my name. For whatever reason it was reassuring. Maybe he was bonding with me in some way, and I thought that was a good thing to help ensure my safety. After looking down at the floor and feeling so intimidated, and still gripping hard on the bottom of my robe to keep it down, I looked up at Hercules and said...

"Hercules, I have to be honest. I'm scared to death and I'm confused and emotionally wiped out."

I started to cry and completely broke down. I felt lost and I was more confused than ever. I heard Hercules rise up from his bunk and I panicked as I continued to sob. He came over to me and to my amazement was understanding and tender.

Standing directly in front of me, he reached out his massive arms and hugged me into his body, my face landed on his stomach. Everything hit me hard and I cried like a baby. All my emotions came out and overflowed. Hercules rubbed my back and said....

"That's Ok Michael. You're safe with me. And you'll never have to do anything you don't want to do. Ever. Understand?"

Feeling better, I replied, "I understand. Please don't let anyone hurt me."

"I already told you, no one will hurt you with me around."

Then something else was happening that I didn't expect. I let go of my robe and hugged Hercules tight. My arms were wrapped around his heavily muscled butt, my face nestled into his muscular stomach. I felt his stomach hair on my face. God, he was so smelly, but I was drawn to the manly scent and it somehow comforted me. It was also sort of sexy. Then I felt something extremely big and heavy pushing against my chest and into my neck. It lodged underneath and up into my lower jaw, pushing my head up and back. It was his enormous cock, which was now distorting and stretching out the front of his sweaty shorts.

As I glanced down I could also smell the most powerful musky scent I'd ever experienced. I involuntarily sniffed it over and over, and Hercules could see my reaction. It had a profound impact on me and as I sniffed I realized I was getting very turning on. I assumed it was because I felt so vulnerable and needy. Then I found myself rubbing my face and little nose on his stomach and smelling his skin and hair. Super-strong man musk scent kept rising up from his crotch...

"Michael, are you more comfortable and relaxed now?"

"Yes Hercules, I feel lots better."

"Remember what I said Michael....You don't have to do anything you don't want to, even to me."

Knowing I could stop where this was going made me want to please him. My robe had slipped up above my ass and crotch and my bare bottom was directly on the bunk's sheets. Not only that, but I realized my little cock was rock hard, and I replied...

"I remember. I need you to protect me and take care of me."

"I promise I will. I want to take care of you Michael."

With that he stepped back a few feet and pulled off his shorts, revealing the most massive cock and balls I'd ever seen. I was overwhelmed with the sheer size of what I saw. Not only that, but big gobs of pre-cum were dripping out of the massive mushroom head and down the super-thick shaft. It was at least 12 inches long and thicker than a beer can. He stayed there, showing it to me, and asked...

"Do you want me to come to you now. Tell me."

I paused and felt confused again. Then he added...

"Don't dwell on what your thinking, go with what you feel, and especially what you need."

He was right. In my heart I wanted to taste, smell, and suck his enormous cock. He glanced down at my hard little penis. I didn't even mind that he was looking at it. In fact, it turned me on that he saw it. For the first time in my life I was sexually proud I had such a cute little penis. Now the robe had really cinched up my little body and I felt totally naked down there...

"Oh Hercules, please come to me now."

He stepped forward, presenting his giant cock and balls to me. His cock was sticking almost straight up and I tentatively put my face on the thick shaft, and lightly rubbed on it with my little turned-up nose. The smell was the most erotic scent I'd ever experienced. I couldn't stop myself from moaning. Hercules reached down and opened up my robe, exposing more of my little white body, all smooth and essentially almost hairless. Then I heard him moan, but it was a much deeper manly moan than mine, which was higher-pitched in comparison.

As I continued rubbing my face and nose on his cock I felt slick and sticky fluid start to accumulate on it and then on my face. I instinctively started licking it up. It tasted so good! Hercules moaned deeply again and reaching down pulled my robe off my shoulders and let it drop down to the bunk. Then I felt his big strong hands on me, caressing my little body, and playing with my hard nipples which were sticking up and feeling very sensitive.

I automatically got more into his giant cock. He moved his hands up to my head and tenderly moved it to where he wanted me to focus, which I did eagerly. I wanted to experience his big heavy balls too, which were so smelly. As if reading my mind he pushed my head down so I could fully experience them.

They were magnificent, the size of two tennis balls, and they were extremely heavy. They were so smelly I initially thought it was too powerful. Hercules sensed my apprehension and held my head there and rubbed his big balls all around my face, especially pushing each one into my little nose. I adjusted to their super-strong man smell and ultimately started to crave it. It cleared my mind of everything except big cock. He was scent-marking my face like he owned me outright. At that very moment he made me his little sissy.

Now Hercules wanted to give me a gift of his big wad, but wanted me on my knees to emphasize his utter dominance. He lifted me off my bunk and pushed me down to the floor. I loved feeling totally subservient to him like that. After letting me enjoy his giant balls some more, he stepped slightly back and pushing down his enormous cock, aimed it at my waiting mouth. I instinctively tried to exaggerate my full lips for him as I kissed all over the giant mushroom head. He tried to push it into my mouth but it wouldn't fit. I sucked on what I could and at least half of the giant head entered my mouth.

Hercules kept applying force in an effort to get the entire head into me. My full lips were getting stretched more than I thought possible. My jaw started to ache as it was being torqued open more and more. I felt my entire mouth slowing opening up and releasing. That's when he stuffed the whole head into it.

Then Hercules started really working my mouth with the giant cock head, and my neck was straining to hold my mouth in place as he pumped it. Thankfully, he released my mouth so I could recover. As I rested my stretched out mouth, pumping the giant cock with my little hands, I had incredible urges to suck him off. Frankly, those urges totally overpowered me and I stuck the giant cock back into my mouth, sucking harder this time. I realized I was whimpering now and desperately wanted to make him cum, and he said....

"I'm about to feed you a massive load of thick cream and make you my little sissy slut."

With that I heard him moan louder than ever as he gripped my head harder. My mouth immediately filled with powerful jets of tasty, rich cream, and then more followed, then again, and again, and yet again. At that point I needed to release my mouth from his cannon cock in order to catch my breath and deal with a mouth full of creamy sperm. I was able to pull my mouth off it, but then rope after rope of thick cum splattered into my face and little body. When he finally stopped unloading he stepped back to admire his work and my beautiful cum soaked feminine-like body.

I liked him looking at my little body lustfully, and even seeing what must have looked like such a tiny cock, given how massive he is. I even stood up so he could get a better look, turning to show my tight little ass to him. As I showed off I rubbed his wad all over my body.

Then I started thinking...

What am I doing?

Why do I like this so much?

Hercules could see I was loosing focus and said, "Michael, remember, go with your urges. Don't second guess them."

His reminder brought me back to my sexy feeling and slutty thoughts, and standing in front of him, I kept rubbing wad all over me, even on my little cock...

"Good, keep going Michael. That's so hot."

Hercules sat back on his bunk and watched the show. I was so encouraged that I rubbed wad all over my face and even through my hair, slicking it back as if it was hair gel. Then I felt the urge to rub it all over my butt cheeks and turned my backside to him as I did so. I even arched my back and spread out my cheeks for him. My little index finger lightly massaged my super-tight hole with Clark's sperm.

At that point I was so horny that I started jerking my little penis and within 60 seconds it started spurting little sprays of clear cum, and some got on my hand. I looked directly into his eyes and raising my hand to my mouth, used my full lips and tongue to eat my watery cum.

I felt so connected to Hercules now and went to him. Lying together on his bunk, I rested on top of his manly body. My head was nestled on his massive and hairy chest. I took in his extreme stud smell, and felt wonderful and serine for the first time in my life. Then Hercules said...

"You are amazing.... I just need to tell you something."

"What is it Hercules?"

"We get all this special treatment because I do favors for them. You see, whenever they need a prisoner punished the guards come to me, and direct me to beat someone up. They tell me how bad to hurt them. Sometimes its just a little roughing up. But other times I tear them apart with my fists. In return I get this special cell, and now I apparently I get you too."

"What happens if you refuse?"

"Michael, if I refuse I go back into the general population, and so do you."

"Now I understand what's going on. Do you like beating people up?"

"Sometimes I do. They are bad people and I hurt them. It's just the way it is in here... But, you'll be expected to do things too."

"Me? Like what Hercules?"

"Well, several of the guards are big body builders and they have their own gym here. They want you to go there and service them during their workout, probably a couple of times a week."

"I only want you.... I can't do that!"

"Michael, you have no choice. You must, or I can't protect you. It's OK with me. It is what it is. Besides, given how much you got off on my body you'll probably really like it."

I was still feeling sexy from sucking off Hercules and was somewhat titillated at the thought of also servicing other big stud musclemen, so I accepted my fate. I think I was encouraged because it sounded like Hercules wouldn't be jealous. After all, no one was more muscular, and no one packs the kind of giant cock and balls that he possesses. He knew I would always want him above all else. He also knew that from now on I'd need to suck a lot of big cock...

"Michael, now you have overpowering urges to suck big cock. The thing is, the more you suck on big cock, the more you'll want it. Of course you will crave mine the most, but you'll want other big cock too. Big musclemen need to be sucked off regularly. Believe me, I know what that deep need does to a muscleman. And Michael, I'll like knowing you've been sucking off big musclemen when you come to me, and I'll like their thick wads all over you."

I was reflecting on everything that happened today, and at the same time excited about being with Hercules, and even being forced to be with other big muscleman studs....