When they say „Go to jail!“ in Monopoly, you’re in for a very restricted round. While the deprivation of freedom is the most characteristic feature of a prison, the accompanying humiliations are even more painful: forced body cleansing, optical alignment with the other inmates, sensory torture through sleep deprivation. All this plays into prison role play.
Being the plaything of sadistic guards, or even worse, being the victim of rape, with the accompanying de facto lack of rights, being unable to do anything about any of these measures, are just a few of the reasons to fear prison to the core. What is an abomination to some is a supreme pleasure to others, because this lack of rights is accompanied by a liberating abdication of responsibility. Thus, the fantasy of prison role play is born.
The fantasy of prison role play
I remember Lennard so well. Without having met me before, The young nouveau riche man from Switzerland had booked two nights straight away, and the program was clear: prison games. To enhance the effect, I added my regular client Olaf as an extra inmate, because being locked up is his thing. The cell wing I rented in Berlin for this prison role play is hidden in a large industrial area. The individual halls are empty in the evening, of course, and convey an eerily erotic feeling.
Olaf picks up my client. As agreed, he receives my new delinquent in front of the street, with his head down and wearing dirty clothes, which gives the impression he’s already affected by incarceration. Olaf just mumbles „Please, come with me“ and starts to move without checking if Lennard really follows him. But he does, and the meter-high walls of the abandoned factory halls, as well as the icy silence of the evening, begin to make his head spin.
Arriving in the main hall, Olaf holds a burlap bag out to Lennard: „Your things have to go in here… everything.“ Well, this is not what Lennard had imagined, after all, he thought he would meet me now. But it’s always an advantage to deviate a little from the classic expectations of the customer – especially in games, where uncertainty is also an exciting factor.
Lennard strips down to his underwear and stuffs everything into the bag. Olaf disappears into the next room with the bag and Lennard’s luggage and announces without eye contact, „The guard is coming now.“
Finally, I make my entrance! In the green police sweater, the thick brown felt pants and the laced boots, I already look like an old-fashioned security guard. The leather gloves, gun, and baton on my belt complete the picture. My upright posture, the precise side parting, and my „mustache“ radiate power consciousness and perversion. And I know it.
„Finally there, huh? We’re firm on discipline and order here. You’re here to serve your sentence, you wimp. You’re nothing here -– just a number. You’re number 17, remember that, and put your hands behind your back when I talk to you.“
It was clear to Lennard that we’d be playing right from the start. He’s already visibly taken by the intro, standing there in nothing but his white panties and bare feet on the dirty concrete, and he clearly senses that I’m loaded and ready for anything.
Humiliated by the guard in prison role play
„Why are you wearing anything at all? Do you think this is a beach vacation or what? Take off your underwear and do it now.“ Within seconds he has the underwear in his hand and wants to hand it to me like a ticket to a ticket inspector. „What am I supposed to do with them? Do you think I have a closet full of underpants made from washcloths like yours? They should have been in the bag, right? Hold them in your own hand. And I want you back where you belong right now – in your cell.“
I turn around, take two steps, and immediately make sure that Lennard (sorry, No. 17) is following me. He dutifully does, and I’m pleased to see that he is erect. We go into the cell wing that is under the main hall. As he passes the first cell, he sees Olaf crouched on his bunk, also naked. Olaf does not look up and seems somehow preoccupied with himself. „You’ve already met number 16.“
The piglet is also due today. The cells are very large and separated by stone walls so the prisoners can’t see each other.
„You may now throw your underpants into the corridor here in front of you.“ I take another step closer to him and say soberly with a smile, „Then you can see the last remnants of your dignity crumpled up in the corridor from the cell.“ The cell door slams shut and the lights go out. „You stay on your cots and I don’t want to hear a peep out of you!“
Only the emergency exit lights at the end of the corridor still provide some light, so Lennard can at least get some orientation: a cot attached to the wall by two chains and covered only by an ugly, rough blanket, a few more grommets in the walls all around that he can make out, as well as a camera pointed steadily at him – that’s about it.
He tells me his thoughts later, „What happens now? Nothing for now? Will he come back now? Will the Dominus dump on me and just leave me here? When the program gets hard, will I be able to do it all? I feel really puny, so naked in this ugly cell, with the guy next door. I’m getting cold. I’m going to walk around a little bit to get my bearings.“
And I? I actually leave them both alone for a whole hour.
After all, we had two days at our disposal, so Lennard should bathe in his own inevitable fantasies. Olaf was instructed not to speak to him. An hour later, the lights come back on. The heavy footsteps of my boots echo as I walk to Olaf’s cell door.
Inside the prison cell
Once inside, I cuff him with his hands above his head, then he receives a loud slap, „Number 16, are you a dirty piglet?“ Olaf answers dutifully and sufferingly, „Yes, I am.“
I know Lennard is listening in on everything and it’s having the desired effect. He later tells me that he wondered, „Is this real? Is he going to do that to me too?“
To Olaf, I say: „Yes, your mind’s rotten, that’s why your little willy is already standing again, you perverted piece of shit.“ I pull on his foreskin and Olaf screams. In fact, Olaf is rock-hard, because this form of humiliation is totally his thing.
I continue to torture him for a few more minutes and always manage to make Olaf scream nice and loud. Again the lights go out and I leave without even looking at Lennard. Later I see on the camera that he had gone very close to the cell door to hear everything very clearly.
Fulfilling his prison role ülay fantasy
After a while, the light comes back on, and this time I go to Lennard’s cell: „What are you doing walking around? You have orders not to move from the bunk! Then I’ll have to tie you up, No. 17.“
I tie him to the bunk and don’t forget to put some rope through his mouth to humiliate him a little. I tie him in a flexible manner, which means he has some room to move in the restraint and can stand it longer. He lets it all happen and I can tell he likes to suffer. „Now we have to see if you have smuggled anything in.“
I calmly and demonstratively put on disposable latex gloves.
It’s clear to the naked Lennard that the only places I could only find something are his body openings. So I first inspect the mouth, which is spread by the rope, and judge it matter-of-factly: „Why are your teeth so crooked? You probably have a few in your mouth from time to time, huh? Serves you right. You obviously can’t behave yourself.“
I illuminate his mouth with a flashlight and feel myself being touched by this intrusion into another’s intimacy. I see his fillings, the different colors of his teeth, and the spit that’s already collecting on the right side of his mouth. I push his head back onto the cot: „The mouth is clean, though not really pretty. There, now you can drool in peace on the cot.“ This boundary crossing stimulates me a lot, and somehow these detailed patterns of the prison role play also bring us closer together.
I lean over to his butt and feel Lennard flinch underneath me. „Wow, what a thick bush you have on your rosette,“ I tell him, pulling a little on the hair around the hole. „That will be shaved clean tomorrow, my friend.“
Now I stick my finger into his butt hole and Lennard sighs. Of course, I treated the finger with some lubricant beforehand. I don’t show this consideration to my prisoner because I want to appear caring, but out of carefulness. This is the great art of BDSM sex work: exploring the playing field on which you can move, going to the edges, but not beyond.
I describe the texture of his hole, and as I feel him there, I become a little more rhythmic in my movements. „I guess 17 is unfucked, huh?“
„No, sir, it’s just been a long time,“ Lennard replies.
„Oh 17, then we’ll make your pussy fuckable as part of your punishment.“
Two full days for the prisoners
I make good on my promise within the setting of our prison role play. I conduct the morning roll, followed by the sporting activities of my convicts in convict clothes in the yard, and then give them „physical training“: My convicts have to shove dildos up each other’s asses.
When nicely stretched, I set them games to see whose cock gets hard first, coupled with strong slaps on their cheeks to increase the pressure. The first hard cock gets to fuck, and the other has to take it. If no one gets hard, they both lose and get a dressing down, but usually at least one of them grows stiff under pressure. It doesn’t stay that way for long,but it’s about having to be fucked, not about enjoying a good ride like in porn.
Of course, the inmates also have to clean the cells. Under my strict control, they sweep the floors and then wipe them clean – on all fours. After that, 16 and 17 have to be washed, of course with a water hose. The convict stands wide-legged, with both hands on the wall, while the fellow prisoner has to hold the hose. I take my washcloth and I ruthlessly scrutinize the convicts‘ private parts: „The pigs have to get really clean.“
Only once they’re thoroughly washed, they get something to eat and a break before our prison role play picks up again in the evening. The second night is experienced much more intensively due to the previous sleep deprivation. This is when their real submissive skills show…