Imprisoned In Chastity

Lynchburg prison was a low security prison for non-dangerous criminals. Mostly white collar criminals with money ended up in this place. It was actually not too shabby a facility. It had single rooms with en suite bathrooms equipped with private showers, drawers for your limited clothing choices and a TV in each room. I was even able to take my Xbox into the prison.

How did I end up here? I was caught cooking the books for the investment bank I was working for. I was high enough up to end up here but not high enough up to get away scot free like my bosses.

I thanked God at the time I didn't end up in a normal prison as at 5"7 and a slight frame I was terrified what would have happened in general population in a rough prison. Oh how it would turn out so different.

As I left the court that day to spend the next four years in the facility I was filled with shame. Why had I allowed myself to be the fall guy? Everybody was on the take but I was paying the penalty. My wife Andrea was furious. Here my high school sweetheart was left alone at 32 years of age. She was a lady of leisure with no children but the money would soon run out. She controlled our marriage and I was infatuated with her. She was the same height as me but she had real curves with massive breasts at 38E and an ass that I worshipped more than money. She made me work for every moment of intimacy. When I was lucky enough to get the signal she was in the mood, I would spend ages on foreplay with my fingers and mouth trying to achieve her orgasm before I would even dream of mounting her with my small five inch pecker. It was weird when we had intercourse as I pumped away at her, I actually felt less of a man as my manhood never felt big enough to satisfy her and rarely could I last long enough to make achieve a penetrative orgasm. Hence why we only had sex that way around once a month if even that frequent. That didn't matter now as I was carted off to prison and as I kissed my bride goodbye I could see genuine anger in her eyes as I let her down.

Entry into the prison did not seem to bad. None of the prisoners looked too menacing and the guards seemed ok. My room was more than adequate considering the circumstances and I was really lucky to get it all to myself. I met my neighbours like Rick, a crooked lawyer from Florida, Joseph, a doctor guilty of serious malpractice and Harold a high profile dentist guilty of a notorious sexual assault on his dental hygienist which he swears he's innocent of. All good guys at first glance.

My life was fine for the first few weeks as I worked my way into the prison environment and routine. It changed overnight when a particular guard returned from his annual leave and was assigned to our wing. His name is Marcus and I knew him from my hometown and school. A big giant of a man well over six foot, Marcus is like a big blond Adonis. He always intimidated me and my friends back in school as he ran the school and scored most of the girls. His eyes lit up when I saw me in my room.

"Well well well, what have we here?" he said.

I replied meekly "Hello Marcus."

He grabbed me to my feet and moved inches to my face, "You will address me properly you little piece of shit, we're not in school anymore. Here you are the convicted little prisoner and I am your worst enemy. I am to be addressed as Mr Maguire. Do you understand?"

I bowed my head and nodded, afraid of this bully. "You married Andrea Browne, didn't you?" Again I nodded without speaking. He proceeded to tell me what a fine piece of ass she was and how he'd fucked her before we got together and she'd always pined for him afterwards.

"Yeah she loved my giant cock, she begged me to take her back after I dumped her. It was kind of pathetic really, but not as pathetic as marrying you", he sneered. "Is she still looking fine or has she ballooned up in weight?" "She's gorgeous," I angrily retorted.

"Don't you raise your voice to me sunshine," with that he turned me around and pushed me into the bed holding my head against the mattress. "Fuck you Marcus," I squealed out with his weight on me.

"Oh really? You will pay for that insubordination. Guard Jones! We have a prisoner here resisting inspection."

With that another large prison officer entered the room. Guard Jones was another giant of a man. A big black fella with burly arms which pinned me down further on the bed unable to escape as Marcus stood up to inspect my room. Marcus started to go through all my stuff as I lay unable to move with Jones holding me down. He went to the drawers and through my clothes before shouting "Ah ha, what have we here Jones? This looks like cocaine and it looks more than just personal usage, have you been trying to distribute this filth in my prison? I'm going to get your prison sentence doubled with this indiscretion alone and may be transferred to a maximum security facility."

I screamed underneath Jones my innocence, I knew the bastard could easily plant that there whilst Jones was busy keeping me pinned down. Marcus told Jones to check on the rest of the wing whilst he interrogated me.

I felt like I was going to vomit. "Why are you doing this to me? I never did anything to you, how can you be such a prick Marcus?"

With that he jumped me again on the bed. "You'll learn eventually, its Mr Maguire to you, understand? I can do whatever I want to you vermin. You thought it was going to be easy in here, well let me tell you how this is really going to go down. You are now my little bitch. One word to the warden with this evidence and you're spending another four years on top of what you got in prison and maybe more if I decide to drum up more shit to stick to you. You will do as I say from this moment on. If I tell you to get down on your knees, you do it in an instant without questioning me. Now bend over the bed to see what we have got."

I lay frightened over the bed as he began to pull down my pants. "No little cotton y fronts won't do Samantha. Let's see what Andrea has been putting up her vagina since she lost big Marcus." Why was he calling me Samantha instead of Sam? He reached around and inside my underwear and felt my penis. He began to rub and stroke it. He began to laugh in my ear. "That is so pathetic, what a tiny little numbin you call a penis," he continued to play with it. "Now I warning you Samantha, you better not get excited with my big hand playing with your tiny clit." This fucking bully had me pinned down and was playing with my cock and demanding I don't get an erection. "Samantha, I remember this one night I fucked Andrea, she came over to my house in nothing but her housecoat. My friends were there and I told her to get lost as we were having a party but she refused to go, so I took her upstairs, removed her jacket and threw it back down the bottom of the stairs and dragged her into the bathroom where I fucked her in front of the mirror at the sink. She was such a whore for my cock. I left her in there naked and went back to my friends. She waited another half hour for my return where she proceeded to blow me whilst sitting naked on the toilet. I came all over her breasts, face and hair. She kept licking me for another twenty minutes until I grew another erection. I made the bitch get down on all fours like a dog as I fucked her in that bathroom with all my friends listening in. She came three times on that bathroom floor. When I was done I told her to get the fuck out. She walked down stairs naked and had to pick up her coat in front of all my friends with her body covered in my sperm. How does that make you feel about your whore wife?"

I was glass eyed into the mattress but my little guy was responding to Marcus' story and actions. To my eternal shame, I started to grow.

"Hahaha, you pathetic worm," I warned you not to get excited. Here feel what a real man has."

With that he unbuttoned his pants with one hand whilst still pinning me down. He reached into his pants and pulled out his penis and began slapping my ass with his member. He taunted me with it and began to move his flaccid penis under my ass cheeks to my own groin to showcase the difference in size.

"Do you feel that? 10 inches baby and it can satisfy any woman. Of even a little sissy girl like you Samantha. You've got a nice little ass that could keep me happy. You just need a little feminization, that's all. Here's what's going to happen. You are now my bitch, I will demand satisfaction now only from you but from your wife. That's right, when you get conjugal rights next Friday, I'm going to be in that trailer with you both and I'm going to fuck Andrea in front of you. Instead of y fronts, you will wear sexy silk lingerie underneath your prison uniform. You will wear perfume, lipstick and clip on earrings. I'm going to enjoy turning you into my little she male. That little penis of yours will get locked up like your rights. I don't want my little bitch getting nasty erections so I have a little chastity device to lock you in. That will keep you horny for me and well behaved. I'll give the key to Andrea to let you out once a month for your conjugal visits but it's up to her how you cum. Do you understand?"

"Yes Mr Maguire," I weakly retorted. The bastard had me. He also had me turned on. I don't know why but the thought of him fucking Andrea in front of me excited me so much. What was wrong with me? Dressing me up in women's lingerie also sounded so naughty but I was terrified of him putting his penis in my ass. I didn't think I was gay. As for the chastity, I had actually begged my wife to lock me up early in my marriage as I spend too much time masturbating but she thought it was weird. Now here I was in prison with my biggest bully about to cuckold me, feminize me and chastise me. There was no way I was going to the warden.

He had me and I had agreed to his terms to avoid extra prison time. "Oh by the way Samantha, no need to tell Andrea, she already knows all of this. We agreed last week when I spend my annual leave at your house fucking her senseless. She can't wait for the real fun to begin."

He left and I stared at my prison wall. What was I really in for?

To be continued?