Prison Survival Guide

I made my way back to my cell block, hoping that no one would stop me but eventually someone did. He was the only black guard, the badge on his chest identified him as Travis. I wasn't sure why all the guards were white, maybe the Warden's hiring policies were motivated at least in part by racism. Travis' hiring might have been something he was forced into to try to assuage any questions of racism. He motioned for me to come to him and then he placed a hand on my shoulder, half pinning me up against the wall.

He leaned in and whispered in my ear, "Has Andre broken you in yet?"

I was blind sided, how did he know about Andre and I, and to such an extent. "No... not yet." Was all I could muster.

"Well he knows our deal and you can keep skating by doing your things for now but eventually you will need to pay up!" he said angrily.

"Skating by?"

"Oh silly girl. Do you think prison is supposed to be this easy? Did honestly think that no one has noticed you stealing shit from your work duty?" he laughed quietly, his words still said in a confident and firm whisper "not that I give a FUCK. I personally think prison labor done for corporations is fucked, helping ensure people get fed and this place is clean is one thing but paying you cents on the dollar doesn't sit right with me. I know the bullshit 13th amendment; 'Neither slavery nor involuntary servitude, except as a punishment for crime' but I don't have to like it. So if you steal shit in my mind it just helps make it a little more fair in my books... but if I see you like now doing it so brazenly I would normally have to punish you for it... however, Andre did make a deal with me and I haven't had to save your ass from the other guards much until today. Although, I did have to convince them not to just rape you when you came in here earlier this week sauntering through in that tight ass women's uniform."

He could see the shock run over my entire face, what kind of deal had Andre struck with him, how was I supposed to repay him, was this part of how he was keeping me safe, not just from the other inmates but the guards as well. I hadn't even considered the guards being a problem before coming here but now being told what Travis had to do to ensure my virginity cut through my soul, yelling at me a deep truth about the world... at least my world.

"Let's get you to your cell before anyone else sees you."

He put his athletic body in front of mine, changing sides back and forth preventing other guards from being able to see me. Taking me back to my empty cell. Andre must have been off doing something else, maybe eating dinner, the block did seem fairly empty.

"Now don't go doing anything this fucking stupid in the future. I can only protect you so much. If it had been a different guard who had found you, you would have been in a world of trouble." He spoke at a more normal volume as he left.

I could feel my entire body shaking, tears were coming down my face, I held my pillow like a teddy bear. I sobbed quietly until I felt a hand on my shoulder, I looked up, it was Andre. I dropped the pillow and flew into his arms. I told him what had happened. I couldn't really make out what emotions his face was hiding. He didn't say a word until I finish my story.

"You have to be more careful Tabitha. Travis is right, if you had been caught that would have been a week of solitary, if not something worse." He said in a firm but sad tone, showing genuine concern.

"I just wanted to do something really nice for you and Caitlyn had offered me all these things."

"Well let's see what you narrowly escaped capture to bring over here." A smile slowly creeping across his face, reaching over to close our cell door.

I stripped off the pants and shirt revealing the lingerie, he licked his lips. I took that off revealing a lacy bra and panties which got a similar reaction. Then the lacy bra taken off to reveal a rather normal looking white bra and then all the other panties until I was back in just the pair I had started the day in. I stashed all of them, hidden under my mattress.

"Well Tabitha that was very dumb but you did manage to snag quite a few things. Caitlyn must really like you, although she should have known better as well." He said in a calm firm voice.

"I'm sorry Andre... how about I make it up tonight?"

He laughed, "Well like Travis said it won't be me but him you will be making it up to... but having fun later tonight does sound great."

"Well I'm going to go get some dinner and then after lock up we can have our fun." I said in a seductive voice, pouting my lips and blowing him a kiss as I walked out.

I made my way to the cafeteria, asked for just a double helping of salad, wanting to make sure to keep my meal light, which was no problem. I ate and then found Andre hanging out in the entertainment area. I sat down in his lap as we all watched some TV show that I wasn't really paying attention to. I could see the jealousy on all the other men's faces, it was impossible to mistake. When lockup was called, Andre and I headed to our cell.

I had him turn around even though he had already seen me naked for 7 straight nights that week and I put on the white lingerie. I turned him around as he wore the biggest shit eating grin that I had seen from him since earlier in the week. We kissed passionately and eventually I pushed him down on to the mattress. Getting on my knees in front of him, pulling down his pants to reveal his semi hard cock. I took the hardening monster in my mouth and hand. Coating it with as much saliva as I could muster. I swirled my tongue around the head and then began to take more and more inches of him. After a week of sucking his cock nightly, I had gotten used to being able to relax and ignore my gag reflex. Tonight I was determined to take every single inch of his 10" cock. I bobbed my head up and down on his massive tool until I had reached then same 8 or so inch point that was my best previously. I pressed on, so excited from my task that I could feel myself getting hard in my lacy white panties. With all my effort and one final push I managed to get him all down my throat, finally feeling his pubic hair on my nose. I looked up at him his entire cock down my throat and he moaned loudly in approval. I continued to bob my head up and down on his cock, now that I had managed to take his entire length, I could do it again and again with relative ease. It was like being able to do it for the first time proved it was possible. I felt him tense up and I was preparing for his load when I felt his hands under my arm pits, pulling me up.

He whispered into my ear, "tonight I want to make you mine." He put me down on to the mattress, face first, pulling my panties down. He went straight for my ass, eating it out which I was learning was something that he truly enjoyed doing. I was starting to moan loudly, so I grabbed the pillow and buried my face in it. I felt his tongue leave my hole, it's warmth replaced with the cool lube. He easily stuck 3 fingers inside of me, fingering me as he has done all week. Then the fingers left my hole, I got nervous knowing what was coming next. I could feel the tip of his cock slowly pushing to enter my hole. I heard a small pop and then his cock was inside of me. I let out a loud moan that even with the pillow filled the walls of our cell. He just grunted and kept pushing a little more and more of himself into me. He began slowly fucking me, not giving me his entire length. Letting me get used to how much he had given me. Then his paced picked up, every time he went back in, I got a little more of his cock, until it happened. I could feel his hips against mine and his pubic mound up against the top of my ass. I shuddered in pleasure having been completely filled by his huge cock. We kept on fucking my body now able to keep in time with his and match his motions. After awhile I could feel an orgasm building up inside of me. My entire body tensed up, then in a shuddering release of it, let go. I came all over the mattress. My body orgasming must have tipped Andre over the edge cause I could soon feel him shaking, filling my hole with his load. He collapsed beside me, us both panting for breath.

I turned to kiss him passionately. I whispered to him, "was that as good for you as it was for me?"

He nodded and whispered in my ear that he loved me. I kissed him and told him that I loved him too. We cooled off for about 30 minutes before we went again, the second time going much easier. I was even able to mostly ride him. Getting him all the way in while in that position was much more difficult. He eventually filled my hole with the second load of his cum that night.

That became my life. Making underwear and lingerie for other girls by day and being Andre's lover by night. I eventually did have to pay back Travis one evening, giving him a blow job in a hidden room, but that would be the only other man I would ever have inside of me. I eventually talked to the prison doctor, telling him I wanted to go on hormone replacement therapy. It was fairly easy to get. I guess when you have someone looking like me walk into your office, the call was easy to make. I ended up with little B cup boobs. I had wanted to get a boob job but there was no way that was being covered. The State had started to cover bottom surgery but by the time my 5 years came up, I hadn't gotten it yet. I even managed to get a name and gender marker change on all my government documents. The only benefit of being in a government facility is how smoothly that went.

I was released very easily on my first attempt at parole. I was a model inmate, never getting caught stealing, and now has come to terms, admitting guilt as to what I had done. I didn't want to leave Andre but he had been forceful, telling me that he didn't want to be the reason I was still stuck in prison and that I needed to get out before I was forever changed by being inside... but it was a little late for that. Being in prison had turned out to be a great thing for me, allowing me to discover my true self.

Getting a job back in computer security was surprisingly easy. I had been honest with them about my life and that I wasn't allowed to be on a computer for the last 5 years but figured I would be able to be back up to speed in a couple weeks. I quickly rose the ranks, kept taking every opportunity given to me and going after everything I could. By the end of the year, I was in charge of the department. Everyone had recognized my talents and were following my lead. I was able to buy a nice condo close to work and a BMW M5 Coupe to go and see Andre in. I was also finally able to get the D cup boobs I wanted for so long. I wanted to get married but he thought he was never getting out.

I had managed to hire a really good lawyer after pleading Andre's case to multiple attorneys. He figured with the right judge we might get lucky... and we did. She was sympathetic to his case and impressed that Andre had gotten his GED and then an engineering degree while inside. Not to mention having no further charges while inside. Sitting there in the court room, holding Andre's hand, I was almost more nervous then when my own sentence was being handed down... and then it happened, Andre was granted release.

We embraced in the court room with cheers from his family, who I had gotten to know very well over the years. His mom had become like a new mother to me. My parents tried to understand the new me, I think they really did, but they just couldn't deal with who I was now, so our relationship became strained. Only time I had seen them after the first day of my release was on Christmas.

We got married 6 months later. I couldn't believe how much I had thrown myself into all the wedding planning... but I loved my wedding dress even more. Both of our families and his friends showed up, even a few of the guys we had spent time with inside were able to make it. Andre looked stunning in his suit. Suits he would come to wear daily after an engineering firm finally gave him a chance. I had offered to help him find work, a few of our clients were in engineering or had department but he was stubborn and wanted to accomplish it on his own. We moved into a cute little house after the wedding.

After a few years, I eventually saved up enough money to get bottom surgery. The recovery process was brutal but Andre took care of me, taking a lot of time away from the office but still managing to get his work done from home. 6 months later he was able to take my 'virginity' for the second time. It took a lot of work to get up to fitting him inside of my new vagina but we took it slow and found positions that would work for us. We had the rest of our lives together and there was no need to rush anything.