Prison Survival Guide

I nodded not saying a word.

"Tabitha, not to be rude, but I'm taking a wild guess here but I take it that you're a virgin? He said in a hushed tone in a way that I knew he didn't mean to offend me.

"Yeah... I never really left my computer other than go to school and work was at a computer as well. I barely talked to anyone at the office other than my boss. I didn't really have any friends."

"Would you like to change that? I don't mean tonight; we will have to work you up to me but we can get started."

I nodded again, my cheeks felt hot as the sun with embarrassment and anticipation.

He leaned over and began to kiss me passionately. He pulled my shirt over my head, kissed me more and then pulled my pants off. He reached to take my boxers off, stopping, locking eye contact in a way saying 'is this okay' without actually saying it. I nodded slowly and he took them off. He broke the kiss, turned me on to my stomach, kissing the back of my neck and then making his way down. He gave my ass a light playful smack, spread my cheeks, and then I felt his tongue on my hole. I moaned a little, but then his tongue darted in and I let out a loud moan.

"Tabitha" he said slowly and quietly "you are going to have to be a bit quieter or the guards are going to come in and then you will be sent to a different cell."

I reached over grabbing my pillow, shoving my face into it, Andre's tongue, went back into my hole. My moans muffled by the pillow were still a bit loud but better. After getting my hole, very wet, he came back up, sticking his fingers in my mouth, I sucked on them hungrily, he kissed me hard before he pushed one finger against my hole, it slowly sliding in, I moaned into his mouth. I reached down and began to rub his already semi hard cock through his pants. I could feel the monster growing under my hand. He took his finger out, I felt disappointed that my hole was empty, until he stuck 2 fingers in this time causing me to let out another loud moan. My body shuddering under his strength, as he finger banged me I could feel the orgasm building quickly.

I had never played with my own butt hole but it felt amazing when he did it. I buried my face into his shoulder as I could feel it coming, my body began to spasm and then I came harder than I ever had in my entire life. Cum came firing out of my hard little cock. Shooting it all over my body. Andre dipped his fingers of his clean hand into the cum, feeding it into my mouth. I sucked his fingers clean eating my own salty cum... another new thing for me. He sat back against the wall, rubbing himself seductively.

I crawled over to him, helping him take off his pants and boxers together. His large black cock coming to life upon release. I couldn't believe the size of it. I had never seen one that big in real life. It was at least 10" long, I took it in my hand, I attempted to wrap my fingers around it but they weren't long enough to make it all the way around. My thumb couldn't even reach the tip of my middle finger. I thought my hands looked dainty compared to his hands but with them on his cock, it looked so feminine. I began to jack him off as best as I could.

"Babe... please try to suck."

He asked so nicely that I had to try plus he already made me cum. I leaned over, taking the head of his cock in my mouth, feeling my lips stretch to get around it. I tried to take more of it in my mouth but gagged almost immediately.

"Don't choke and die on me now Tabitha." He laughed a bit "Just take as much as you can, if you keep sucking on the head and jerking me off, that will be enough."

I concentrated on doing exactly that. Moving my hand up and down, feeling it hit my lips, I reached out my other hand, messaging his balls. I felt him tense up and groan, knowing what was coming, I prepared and then hot load hit the back of my throat, I swallowed as quickly as I could but it wasn't enough and a good amount came out onto my chin and chest. I sat back, taking my fingers and pushing the rest of his load from my chin into my mouth. He smiled widely.

"I thought that was going to be a lot harder and take a lot longer but damn you're already turning into quite the good slut."

I blushed hard, "Well you did say that I needed to give you something in exchange for your protection."

"I did... but nah it's more than that. You enjoyed that shit. I could see in your eyes."

"You're right, I did."

"Well, that's good! We will just have to work that tight hole of yours to fit me."

I was happy that we was being so gentle and sweet to me. In my moments of panic about prison, I worried, probably way too much, about being assaulted by some guy not caring and just making me his bitch. I was becoming Andre's but not in that way, thankfully. If he wanted to take me that way he could do it easily.

He went over to his bed as there was no way we would have had enough space to sleep together plus the more pressing issue of the guards discovering us. I managed to fall asleep fairly easily, that had surprised me but I did just have the best orgasm ever and a busy day.

The morning came far too early, the sound of all the doors unlocking, I headed to the shower sheepishly behind Andre. He had already seen me naked but having all the other men looking me over like a piece of meat, in the big open showers, was something I was not prepared for. Thankfully it went really smoothly. The guards knew what they were doing, Andre's group, which I guess I had become a part of showered separately from the other groups that would be antagonistic. It felt good to get last nights dried cum off my body.

Feeling mostly fresh and dressed, I was escorted by one of the guards down a long hallway to my work detail. The buzzing sounds of the sowing machines. There wasn't much talking going on. The scene reminded me of videos I had seen from the third world.

The guard in charge came over, a woman in her mid 40s, a bit chubby but from the look on her face I could tell she wasn't one to fuck with, "Ms. Anderson?"

"Mister actually..." I replied.

"You're orange outfit would suggest that but the image standing in front of me suggests something else." She trailed off for a moment, "You're the only 'male' here, so I think I will call one of our other guards to bring you clothes better suited to you, so you and the other girls feel more comfortable around each other."

I couldn't believe what was happening. I knew the guards had a lot of power and leeway in how they handled prisoners but this guard was just supposed to be over seeing the work being done and only acting if someone got out of line at least that was the impression I was given. She radioed loudly for one the guards from the female unit to bring me a full set of new clothes. Everyone in the room was starting at me, though they didn't stop working, my cheeks flushed with embarrassment. In short order there was another female guard in front of me giving me the full female uniform. Pink t-shirt and pants, white cotton panties and bras, which felt just as itchy as the boxers I was currently wearing, the socks and slip on shoes looked to be basically the same.

"I got them to bring you size small cause it looks like you are wearing a size small and it's too big for you. These should fit much better." The older woman said in a cruel voice. "Now get changed!" I went to leave to the bathroom. She grabbed me by the shoulder. "No, silly girl, you will change right here." I'd heard the term 'command voice' before. I hadn't understood what the term meant until now.

"Don't make me repeat myself girl." She said forcefully.

I slowly pulled off my shirt, I could feel every eye in the room on me, my cheeks felt somehow redder than ever, burning hot, I took off my shoes, socks and then pants, standing there in just my boxers. Looking at the guard's face seeing no emotion but annoyance as I finally pushed my boxers off. I had half expected her to make some snide comment about my dick but nothing came out. Instead, she just handed me back the panties first. I pulled them up my legs, they were definitely as itchy as the boxers but now they hugged my ass. I pulled up the pink pants to cover the panties. I had a bit of trouble with the bra but it eventually got on, unsure as to why I needed it, maybe just humiliation and then the shirt over top of it once I finally got it in.

The guard was right. These clothes did fit my body much better. In addition to the panties, the pants also hugged my ass. I wasn't swimming in the t-shirt any longer.

"There we go, finally. Now it's time for you to introduce yourself to the room."

"My name is Tabitha" I said quietly.

"Louder, girl. It's a big room." She said angrily

"My name is Tabitha." I repeated louder.

"Good! I think you are in need of a haircut and make over but that will have to wait until we are done here. Go sit down with Caitlyn. She will show you what we do here." She pointed over to a girl who looked to be not much older than I. She had a very pretty soft face and I couldn't help but wonder what got her here.

I sat with her, hanging on her every word for the instructions on how to accomplish the task. Today we were making panties. She had told me that was the easiest and what everyone started on. Eventually you could move up to bras and lingerie, they paid a little better.

Lunch was given, just a simple ham sandwich, eaten away from the clothes. Caitlyn asked about my life, so I gave her the quick version of it. We weren't given much time to eat then it was right back to work. By the afternoon I had watched her sew enough panties that I felt up to doing it myself. The first couple of pairs went poorly and needed Caitlyn's help to correct them. I finally nailed my first pair, a black soft lacy thong.

An idea crossed my mind unsure if I could pull it off, if I got caught I would be fucked harder than a blind pussy in a dick forest. But my nerves caught up and I went for it. I looked around the room, everyone was focused on their work, the guard was busy looking at another inmate's work, I stuffed the thong into my pants, tucking them under my panties as the pants had no pockets. I stood up and walked over the guard, letting her know that I had to go to the washroom. She told me where it was down the hallway. I went into the washroom and went into the stall. I took off my pants and the itchy cotton panties. I pulled the thong up my legs, it felt so good compared to what I had been wearing. I pulled the cotton panties back over the thong and then pants.

I walked back to the work room and went back to work. Getting lost in the work, concentrating on it like the way I would when studying for a test for a class I hated. The day went by fast. I was ready to go back to show Andre what I had managed to take, but then as I was walking out, I was ushered over to the women's side of the prison.

Right into the salon, in there was a black woman in her mid 30s, she sat me down in the chair, took my hair out of its usual pony tail, it going down past my shoulder blades. She ran a brush through my hair, telling me how beautiful my hair was. I had always taken pride in my hair, taking the best care of it I could afford. She showed me a few pics of famous people's haircuts. I found picture of Kate Beckinsale and I really liked her haircut. She smiled at my choice, as the color was processing, she plucked my eyebrows into a feminine arch and shape, then she put on some long lashes individually, I was amazed at how much effort it took and how they even managed to get inside the prison. She applied some pink inch long press on nails telling me how a lot of the girls that did my job liked having them.

90 minutes later, it was all done. She washed my hair and then blow dried it, styling it in the process. Then she handed me foundation and taught me how to apply it. Finally, a bit of pink lip-gloss and the look was complete. I couldn't believe how I looked. Staring back in the mirror was a beautiful young woman, trying to wipe the smile off my face would be like trying to wipe away the ocean.

I floated on cloud 9 making my way back to the men's side, a few men stared at what looked like a woman before them. I headed to the cafeteria and managed to scrounge up some food, thankfully there was still some spaghetti left. I ate and then headed back to cell block C. I found Andre in our cell reading what looked like an Engineering textbook rather then out and about. Placing his book down, he looked me up and down then the biggest shit eating grin I'd ever seen crossed his face.

"Damn girl! You look fucking amazing Tabitha!" He said with more joy in his voice than I thought I had ever heard.

"Thank you. I'm really glad that you like how I look." I smiled like a child who had just gotten an A on a test.

"Like? I love it! How did you manage to get one of the women's unis?"

"Actually that wasn't my doing, the guard in charge of the work detail made me put them on, something about making the other girls feel more comfortable.. and she was also behind the makeover... But!" I pulled down my pants and the cotton panties revealing the black lacy thong "This was all me!"

He seemed genuinely impressed and maybe a little surprised at the new information.

"You look just about perfect!"

"Just about?" I answered confused.

"I was going to wait awhile for this but the way you are diving in head first tells me that you are probably ready for it. Do you trust me Tabitha?"

"I do!"

"Well then follow me."

With that we headed down a few hallways to a back area that I wasn't shown on my initial tour. We walked into a mock entertainment room. It had a couple of couches, an old CRT TV and a PlayStation hooked up to it. It wasn't much but I guessed this is what passed for luxury in the prison. There was a few black men mulling about. A couple of them playing Mortal Kombat, the other just watching.

Andre could see the look of confusion in my eyes. "You see every group gets their own little entertainment room... well the rooms are shared and scheduled times. We are in the last two hours before lock up. The guards were hesitant when they first came in but realized it helped keep things calmer. It's mostly separated by race but this prison is so damn heavily self segregated... but it's what works and keeps the issues to a minimum."

Andre sat me down to the guy who was watching the guys game and whispered something in his ear. A big smile came across the man's face. He looked around and pulled out a makeshift tattoo gun, then he rooted around in the couch some more, pulling out a small jar of black ink. He turned to Andre.

"So, where are we putting this?"

"I think right above the pelvis, near the hip bone, right or left side, doesn't really matter."

The man turned to me with kind eyes "And you... You are down for this? It's not temporary you will have this for the rest of your life. I mean you could get it covered up on the outside but not while in here realistically."

I tuned to Andre looking at him with questioning eyes, unsure of the words.

He spoke softly "It will mark you as part of our group. It will make things safer for you. Anyone who sees it will know to stay clear."

I nodded anxiously, "I'm down."

The other man motioned me to lie down as he stood up off the couch and kneeled down beside it. I lied down, he gently pulled up my shirt to my navel, then he pulled down my pants and panties down, not off but enough to reveal my public mound, he stopped when he could feel them tugging at my dick indicating the top of the mound. He produced a razor from somewhere and dry shaved my pubic area. It didn't feel great. He looked up at me. He took a pen and drew on the design.

"You ready?"

I nodded and then the buzzing noise kicked in. Then the first line began. It felt horrible. Kind of like a constant bee sting. But as he continued, I settled in getting used to the pain. Andre took my hand in his, offering to let my squeeze it, and so I did. Focusing on my hand in his hand allowed my mind to focus away from the pain. After 30 minutes or so, he was done. He handed me a small mirror so I could look at it. It was a black spade with a flesh-colored Q in the middle. I pondered for a moment and then realized it symbolized the Queen of Spades unsure of what else it might mean. I stood up, the tattoo artist called the attention of the guys gaming to have a look. They both got big smiles across their faces.

"Damn Andre, you got this one turned quick." The one guy said to him.

"I honestly didn't do much, she pretty much just went right for it." He chuckled softly.

I could feel both of the men's eyes practically undressing me and the hunger in their eyes was like someone who hadn't eaten in a month staring at a steak. Andre took my hand and led me back to the cell. After lockup we repeated last night's activities except Andre had somehow managed to track down some lube, that allowed 3 of fingers in my hole. He still ate my ass though like a champ beforehand. I managed to get a couple more inches of his cock into my mouth, slowly figuring out how to control my gag reflex.

After a week of prison life, I had pretty much settled into a routine. Andre showed me a few exercises in the gym to make my ass look even better, he corrected my form on squats. I wasn't surprised that I was doing them wrong. I had even found spare time to start reading a book, Dreamcatcher by Stephen King. It was one of my favorites as a kid and it helped transport me somewhere else. Even just for a moment. Being with Andre was like that too, any time I was with him especially sexually, I found myself able to forget where I was.

Work detail was going well, I was able to power through making so many panties, that they hadn't realized, or weren't concerned that I had stolen a pair a day. There was probably some loss built into their projected numbers. Couldn't expect a bunch of convicts to be making underwear and not have some go missing. I tried to make friends with some of the other girls but most just wanted to keep their heads down and get the work done. Caitlyn on the other hand had become my best friend. Talking to her after a week was like speaking with someone I knew my entire life. I even admitted to her about the panty stealing. She laughed at the revelation and had told me most girls had figured out multiple ways of getting stolen items, then she surprised me and asked if I wanted more stuff, I enthusiastically said yes. I wanted badly to get out of the itchy bra and get something cute to wear for Andre.

After our work day was complete we went back to the women's cell block. At this point no one really questioned me as to what I was doing on either side. On the women's side everyone just seen me as another woman, even the guards, and on the men's side everyone who mattered had gotten used to a female looking guy in women's prison garb walking around. I was even granted the opportunity to hand wash my uniform and given a back up set to wear while they were drying. The prison staff genuinely seemed to care about cleanliness, at least outside of the prisoner's individual cells, and they of course put inmates to the work of keeping it clean. We arrived at Caitlyn's cell where she handed me a few more panties, a couple of bras and a very sexy white piece of lingerie with matching panties. It looked almost like something a bride would wear on her wedding night to me. Which would be perfect for Andre finally taking my virginity.

I asked her confused about how to get it all back without getting caught. She laughed and told me the same way that I had stolen everything else. So I stripped off the itchy cotton prison bra, putting on the two bras over top of each other, all the panties over each other in succession and then finally the lingerie. I put my clothes back on over top. I looked ridiculous and for anyone who starred for too long could tell something was up.