The following is a work of fiction. All parties depicted are 18 years of age or older. This picks up right after the previous parts. Please read them in order.

I’m a wealthy playboy. I’m constantly partying and consorting with high-end call girls. Something happens and I go to court and am sentenced to prison for a few months. I have to turn myself in next week. This is not a minimum security place for rich guys, but this prison has a reputation for being a rough place and I’m scared shitless. I have no idea how to act or avoid trouble. I did a lot of searching on the Internet about prison life and I ran across a consultant for people like me who teaches how to survive in prison. I set up an immediate session, transfer a lot of money, and showed up at his place.

The consultant is a big scary looking guy with a lot of tattoos, who looks like he’s spent a lot of time in prison. I’m curious but I’m too nervous to ask him about his time behind bars. We sit down and he explains that most of my fears are fear of the unknown, so he will show me what to expect, and once I’ve experienced many of these things, they will no longer seem as scary. He says that we’ll walk through most of the things that will happen after I turn myself in. He says that the session will last 48 hours and I’ll experience what it’s like to be a prisoner.

The first thing he does is put me up against the wall and tells me to “spread ‘em”. He does a very thorough search, paying special attention to areas where I might hide something, like my crotch. Then he handcuffs my hands behind my back and walks me down a hallway. We go into a small windowless room and he removes the cuffs. He takes my mugshot and fingerprints me. Then he has me empty my pockets and does an inventory of my belongings.

Then he orders me to strip. I slowly strip down to my boxer shorts, and he tells me “Everything” and I remove my underwear. He puts on latex gloves and has me hold my hands out to my sides. He checks my hair. He has me open my mouth, where he shines a flashlight and probes around inside my mouth with his fingers. He grabs my cock and pulls it up, checking behind it, followed by grabbing my balls and checking behind them too. I flinch away when he grabs my balls, which earns them a hard squeeze while telling me not to resist.

He spins me around and bends me over a metal table. I look back to see him lubing up his fingers on his right hand. I protest and start to straighten up, but he grabs the back of my head and pushes me back down on the table, telling me to “hold still”. He puts one of his booted feet between mine and pushes my legs apart while telling me to “spread ‘em”.

I feel a finger go in my ass. He holds it there and tells me that I need to get used to the feeling as he moves it in and out, probing my ass. He tells me that if I resist the cavity search, the guard may insert more than one finger in my ass as punishment. He proceeds to demonstrate that by inserting two fingers. That hurts and I let out a yelp, but he holds them in me.

I say that I may have made a mistake and say that I’d like to cancel this session and leave, offering full payment. He keeps fingering me and says that my ass is really tight, and it’ll be a favorite among the other prisoners and maybe even the guards! He tells me that if I leave now, I’ll miss the most important part about saving my ass while in prison. I reluctantly agree to stay. He says that from this point forward, I won’t be allowed to leave until the entire 48-hour session is complete, and I agree to continue.

Then he handcuffs my hands behind me again and starts walking me down a different hall, while I’m still naked! He explains that the guards like to humiliate the new fish and I’ll probably be brought into the main area naked in front of all of the other prisoners.

At the end of the hall is a door that opened into an area set up like a small prison with some jail cells lining one of the walls. He takes me to one of the cells and pushes me inside, slamming and locking the door behind me. The only thing in the cell is a small bunk and a toilet.

He has me back up against the bars and he removes the handcuffs. He walks away and I curl up on the bunk, still naked. There aren’t any clocks, so I don’t know how much time passed before he came back holding a tray of food. He explains that if I’m put on suicide watch, I won’t be allowed any clothes in the cell, and he wanted to show how that feels.

He leaves the food. I eat some of it, but it’s terrible. He comes back later and takes the tray. Then all of the lights go out at once, leaving a few dim lights on. He comes by and tells me that it’s night and I should try to get some sleep. I toss and turn for a couple of hours when my guard returns again. He tells me to back up against the bars, handcuffs me, opens the cell, and walks me down to a small office without any windows.

There he tells me that because of my twinkish body and tight ass, I’ll likely be raped a lot when I’m put in the general population unless I get some help. I ask how to get help, and he explains that I need someone to watch over me. It could be a prisoner that nobody messes with or a guard. He said no matter who I get, I’m going to have to give special favors in exchange for help. I hesitantly asked what kind of favors he was talking about, and he said that if I want to keep my ass safe, I’ll need to give good blowjobs. There has to be another way, I say, but he replied that unfortunately there isn’t. Then he asks if I want to blow him now, otherwise, he’s going to bend me over the desk and fuck my ass. He says he’ll take it easy on me and coach me about how to give a good blowjob, which is a very important skill to have in prison.

I’m whining that I don’t want to do this, so he bends me over the table and says “Okay, have it your way”. I start freaking out and then say that I’ll blow him, just leave my ass alone! He makes me beg to give him a blowjob before he finally lets me up, and has me kneel before him.

He lowers his pants and takes out this huge cock that I’m not sure will even fit into my mouth. He tells me to open my mouth as wide as I can while telling me what’s going to happen to my ass if I bite him or he feels any teeth.

He tells me to take my time and start out slowly. I kiss his cock head and lick his shaft before I take it in my mouth. I wish I could use my hands to help stimulate him, but they are still cuffed behind my back. He tells me to take him as deep as I can. He’s not even in my mouth halfway before I start to choke and pull back away from him. He tells me some things to try so I can take him deeper into my mouth. I’m moving my head forward and back, taking him a little over halfway when he grabs the back of my head and shoves his cock all the way to the back of my throat. He lets me come up for air and tells me that’s what I need to do in order to make him cum. I say that I can’t take it that deep, and he gives me the choice of doing it myself, or he’ll shove himself in that deep again, and keep fucking my face. I agree to try it myself.

I’m trying my best now and I’m able to take him almost all the way in my mouth for quick thrusts. I feel his breathing start to increase and him tensing up. Then he grabs the back of my head and shoves himself in my mouth hard as I feel his cum filling my mouth. He manages to yell “Swallow it all” as he’s cumming. I try to swallow, but I’m mainly gagging and trying to spit everything out of my mouth. Then he shoves me back and I fall onto the floor, choking, gagging, and coughing.

When I finally calm down a little, he pulls me to my feet and walks me back to my cell. He uncuffs me, locks me inside, and tosses me an orange jumpsuit. He said that I did okay for the first time, but I have a lot of room for improvement, and we’ll be doing a lot more practice during our session. He tells me to get some sleep now, turns and starts to leave, then turns back and tells me “No jerking off or you'll pay with your ass". I’m left alone in my cell for the rest of the night and cry myself to sleep.