The Prison of My Dreams

by Madam S

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© Copyright 2023 - Madam S - Used by permission

Storycodes: MF/f; bond; cuffs; cage; cell; chain; island; resort; prison; sex; oral; cons; X

This short story is about a business where various BDSM fantasies, like a prison, ponygirl, hucow, slave market, consensual kidnapping, etc., are fulfilled. Customers are women only. The men can go to the island as visitors but don't act directly in the scenes. Scenes are all employee-driven, so SSC (Safe, Sane, and Consensual) is followed. The island is in the Caribbean and can only be reached by boat or in a small private plane. Cell phones are prohibited, which ensures everyone's privacy. Amanda, one of the clients, will tell this tale.

My name is Amanda. I'm 34 years old, 1.65 m, and 62 kg. I'm fit (hot), with big breasts, strong legs, and a thin waist. I've always fantasized about being trapped in prison full of handcuffs and restraints. However, I wanted a safe and controlled environment. I heard about BDSM Paradise, a remote island in the Caribbean, from a friend, and I immediately became interested. I got in touch and received a quote and a form to fill out. The price was too high, but I could afford it (thanks to a nice inheritance I received). The form was quite long, with personal details, medical details, and a list of what they offered, and I would have to mark what I preferred. The list was as follows:

Prison Package: Being arrested inside the island for any reason. Write down the treatment you want to have in prison:

  1. Arrive handcuffed in prison. (sure)
  2. To be frisked and strip-searched. If so, by male or female. (Of course, it's a prison. And the inmate doesn't choose the jailer's gender).
  3. Cell with other inmates or solitary confinement. (Other inmates. Solitary only in case of punishment).
  4. Handcuffs inside the cell. (No, that would be too much).
  5. Handcuffs to get out of the cell. (Yes)

There was nothing else to fill. I signed up for a 14-day package and was informed that I would not be arrested immediately but within those 14 days. I would spend a minimum of 5 and a maximum of 14 days in prison. Either I would be arrested as soon as I arrived, or I could enjoy a 5-star hotel for up to nine days, all expenses paid, and then be arrested. It wasn't a bad deal. As soon as I signed, I received tickets to the British Virgin Islands airport and information on how to take the boat to the island.

I arrived at the airport and soon saw the designated shuttle to take me to the island. I was instructed to take only one carry-on bag. I was also recommended to wear comfortable clothes because I would have to walk, but bring clothes to go out at night. So I traveled wearing jeans, a blouse, and sneakers. I got into the shuttle, and soon we arrived at the port. The boat could have been more beautiful and luxurious. It was a simple boat, like a medium-sized fishing boat. The captain welcomed me and directed me to the passenger section. It was a large cabin with covered windows. The privacy and exclusivity of the place require that we don't know exactly where it is. I had to hand over my suitcase and everything in my pockets (cell phone included) to the captain. He put everything in a bag and said: "On my boat, I demand silence. Do not talk to the other passengers." I entered the cabin and saw five more women, all in their 25s and 40s and all very beautiful. As they were all quiet, I didn't risk starting a conversation.

The journey was boring, an hour across the calm Caribbean sea, but unable to see anything and sitting on a wooden bench. Finally, we arrived at the island. We got off the boat, but they didn't give us the luggage. A hotel employee welcomes us and says that the luggage will be at the hotel and that we should follow him. He says the walk will be short, 30 minutes tops. The walk was very pleasant. The island is beautiful, a piece of paradise in the Caribbean. The path is along a very well-paved sidewalk. Sometimes, I noticed we made some unnecessary curves, but that was ok. The birdsong was also beautiful.

Upon arriving at the hotel, a pleasant surprise, the hotel is beautiful and sumptuous. At the reception, I saw a beautiful receptionist. Her uniform was super low-cut and short. I said I didn't have my luggage, and she said it would be in the room. However, my cell phone would stay with them, as any photo or video was prohibited. My wallet with ID would be kept at the reception, too, since I only needed to use the hotel ID card, and everything would be fine. The ID card opened the room door and would also be my identification on the island. I wouldn't need money because it was all-inclusive. My friend had already told me about it, so I didn't worry.

I went up to my room and was impressed again. A beautiful room with a great island view, a super comfortable king bed, and a large TV with amazing cable service. Finally, a 5-star hotel. As it was still early, I put on beach clothes and spent the day sunbathing and enjoying the beach bar. When I returned to the room, a note was under the door from a welcome party at a nearby bar. Party with live music and lots of beautiful people. Wow, I'll be there.

I took a shower and got dressed for the party. The hotel staff was nice and hot, and the night could end well. I wore a tight-fitting short dress, highlighting my breasts, hips, and legs. Three-inch high heels and sexy lingerie completed my outfit. Light makeup, ponytail, hotel card in her purse, and off we go.

The journey to the bar was on foot. It was less than 30 meters from the hotel, two houses next door. A grand entrance and the music already rolling. It must have been around 10:00 pm, and, at the entrance, an employee dressed exactly like the receptionist, in a super short and low-cut dress, asked to check the purse. I opened it and, as instructed, only the hotel card was available. The employee ran the hotel card through a reader, and nothing happened. She tried several times and said, "something must be wrong. I'll call my supervisor". She then got on the radio and called the supervisor.

The supervisor arrived, and my legs shook. A demigod. About 30 years old, 1.85m tall, super athletic, not pumped up, super tight shirt that emphasizes his chest, dark hair, and stubble. Wow, I was horny and wet. He asked my name, I replied, and he said: "Miss Amanda, come with me, let's see what's going on." We entered a room, and he asked me to sit on a chair. He sat in the other and asked about my documents. I replied that they were at the hotel reception, and he continued to ask me why I was walking around the island without documents and that this was completely against the rules of the place. I tried to explain that the hotel receptionist had asked for it, and he started talking louder, which scared me.

The supervisor said: "Wait, I'll call the hotel." I was more relieved that the hotel would explain everything. Then he arrives and says: "I'm sorry, the hotel reception said this card is invalid." Then two security officers came in. One of them took me by the arm out of the chair. He had me facing the wall, and when he searched me, he said he found a small knife wrapped in my thigh, which was a lie. I tried to argue, and then the other security officer came. In a matter of a few seconds, I was on the floor, face down, with one knee behind my back and my wrists painfully handcuffed behind my back. I tried to flail with my legs, and then a handcuff was placed around my ankles, allowing me to take small steps but no more trying to kick anyone. Finally, when it was time to get up, what a pain; they pulled me by my handcuffed arms, almost dislocating my shoulder. But since every time I tried to speak, I was treated badly, this time, I kept quiet. As they led me out, they each held me by one arm, and because of the shackles on my ankles, I had to take short steps. To add to the humiliation, they paraded me around the bar, the music stopped, and everyone stared at me. I don't know if my dress had ridden up by the movement of them throwing me to the ground or lifting me, and I was pretty sure part of my ass was showing. Ultimately, they put me in the back seat of an electric car, with all the windows tinted, without removing my handcuffs.

We stopped after about 10-15 minutes. Upon descending, I discovered that I was in a jail, and the resemblance to a real jail was striking. I was then taken to a room where I was asked my name, when I arrived, when I was leaving, etc. Then they took pictures of my face from the front and side. Then a policeman arrived who took my handcuffs and asked me to remove my clothes for the search. I stood still and asked, "here?". He continued to stare at me and didn't say anything. Finally, I got the message and, ashamed, took off the dress and heels, leaving only my bra and panties. He continued looking at me and said, "take it all off." Even more embarrassed, I took it off. Next, he ordered me to face the wall and frisk me. He started with the hair, then felt my breasts and put on a glove, and stuck two fingers in my vagina and then, without lubricating, one finger in the anus. At that time, I screamed in pain, and he just laughed. Then he turned me around, told me to open my mouth, and started looking at me in the teeth like a horse. Wow, how angry I was at this time.

He left for a few seconds and returned with a uniform. He ordered me to dress there. Since I was already naked, I started to get dressed:

  1. Some panties, big, not sexy at all. Then a pair of baggy blue fabric pants, probably too large for me.
  2. A T-shirt that fit tightly over her breasts and flared over my belly. I asked if he didn't have a bra, and he ignored me.
  3. A slipper that looked like flip-flops but was made of very poor material.

The entire uniform showed a below-average quality. I noticed that, at the top of my breasts, there was a number on my uniform, 221030. The officer then said to me: 221030, put your wrists forward. At the time, I understood that it would be called from then on. I put my wrists forward and was handcuffed. He also handcuffed me at the feet and secured the two handcuffs with a chain. I couldn't lift my hands, and my steps became even shorter. He gave me a clear plastic bag with a hairbrush, toothpaste, bed linen, and a towel. Oh, how I miss the hotel.

We walked through some doors and into a large hallway. We then arrived at a pavilion with several cells and inmates. It wasn't possible to know who was a guest and who was hired, and I didn't find it interesting to ask. I then arrived at a cell. I went in, and the officer took my handcuffs off. Inside were three more women, also pretty and about my age and dressed like me. A lavatory and two bunk beds were also on each side of the cell. Only one "window" of reduced size faced the outside. However, it was tall and with a railing. From there, you could only see the sky. There was no shower. Then, one of the women, approximately 35, 38 years old, very dark, tall (almost 1.80m), and strong (more chubby than strong), pointed to one of the beds at the top and said: "that is your bed." When I got to the bed, I saw that the bunk bed was solid concrete, and the mattress looked more like a gym mat. I ask from the pillow, and the three of them start laughing. Finally, the brunette, who seems to be the cell's leader, says: "this is not a hotel, 221030". I look down and say nothing. She then comes close to me and, placing her hand on her waist, speaks loudly, "here, when I speak, you answer yes ma'am or no ma'am, do you understand?" Instinctively, I say, "yes ma'am." At that time, I thought: "my fantasy is coming true, but is this what I want?".

Before going to bed, one of the inmates came to me and told me she was returning after two days in solitary. She said that it was hell. You stay naked, with no bed. It is so humid that you get wet if you try to sleep on the floor. There is no shower, only a dirty, stinky toilet. The food is cold leftovers, served only once a day. The water looks like toilet water. She was sure she saw some rats over there, or she was hallucinating. She said that if she stayed there longer, she would go nuts. I don't know if it is true or if she was trying to scare me. However, if she was trying to scare me, she got it. I was terrified and had nightmares about it. I don't want to be there, not even for a second.

To my surprise, in the early morning (or late at night), I feel someone hitting my ass before everyone wakes up. I wake up scared, and one of the inmates says, "Ma'am wants a good morning." I, scared, ask: "what?" Then the other inmate comes along, pulling me off the bed and onto my knees. Then I see the cell leader, a very dark, slightly overweight woman in her mid-40s, sitting on the edge of the bed with her pants down and pointing at her pussy. I try to argue that I'm not a lesbian, but my face is forced between her legs within seconds. From there, she closes her legs over my head (and I realize she's stronger than I thought) and starts to press. I feel a huge pain in my ears and head and start licking. She feels me licking and relieving the pressure. I got the message. I realize that I have no choice, so I start to lick the clit and pussy and also suck with my tongue deep inside her wet pussy. She was excited and moaning, so I stuck my tongue deep inside her pussy and started sucking like it was the most important task of my life. Even though it was my first time, I got wet, and when she came into my mouth, I almost came too. Instinctively, I put my hand on my clit, and one of the inmates slapped my arm and said: "here, only madam comes." I groaned loudly in frustration.

A siren rang when I was still swallowing the madam's juice, and everyone was told to wake up. I was startled, and we all got up. The cell doors were opened, and we were told to line up for breakfast. The three inmates stood before me, and I decided not to complain. There were about 20 or 30 women, and I wondered how many would be "guests" like me and how many would-be employees. The officers handcuffed our wrists to the front and added leg irons on the ankles, making movement slow and difficult. We stayed at the end of the line. We entered a cafeteria with a large table and breakfast consisting of a black coffee, a plate with two slices of bread, and a banana. I looked and thought, "for the price I paid, I could pay for everyone's coffee here." The officers removed the handcuffs and leg irons and said. "15 minutes for breakfast."

The inmate beside me, whom I had never seen, said, "I want your banana." I looked back and said, "what?". Then, out of nowhere, she slaps my plate, knocking it to the floor, and pushes me away. Before I could think, two or three officers grabbed me, knocked me to the ground, handcuffed my wrists tightly behind my back, and put leg irons on my ankles. One of them said, "Troublemaker inmate, come with us." I got up, and the inmate who hit my plate smiled and winked. I immediately thought, "I'm screwed." The officers took me to a room that looked more like a courtroom. They put me in a cell in the corner like a cage. They said, "the judge will be here soon to talk to you. And no, we're not going to take your handcuffs off." Then a man came up to me and said, "you're Nakanda, aren't you?" I look and say "no, my name is Amanda." He apologizes and says he will be my attorney. I smile and think, "what a great lawyer. You don't even know my name."

After a few minutes of boredom and discomfort with my wrists handcuffed behind me (it gives my shoulder a lot of pain), the judge enters. He starts saying. We have inmate 22103040, accused of entering the island with a false card and assaulting an inmate. Is that right, lawyer? And then, to my surprise, the lawyer was kind of ok with it. The judge said that, as I could not get along with other inmates, I would be in solitary confinement until the end of my time on the island. At that time, I said, "Hey, that was not like that." At that moment, everything stopped, and everyone looked at me. Instinctively I looked down. The judge ordered an officer to remove me from the cage and take me to the judge's room next to the court.

The officer takes me out of the cage without removing my cuffs and leads me into a small room. The judge stands, waiting for me, and the officer kicks the back of my knees, "inviting" me to my knees. The judge asks the officer to remove the handcuffs and handcuff me again with my wrists in front of me. The judge then says, "Do you think you can get along with the other inmates?" I reply, head down, "yes, sir." He pulls down his pants, and I see a big flaccid cock. He says, "I need to make sure of this," and puts the cock in front of my mouth.

I got the message and realized I suck or am in solitary confinement. So I started a blowjob and caressed the balls with my cuffed hands. I started to get horny because the dick was good. By the way, the judge was not that bad. He was around 50, with light brown hair and a well-defined body. When I was sucking hard, the officer said, "on all fours." I promptly obeyed without letting the judge dick out of my mouth and felt the officer lower my pants and panties. I was wet from the blowjob, and the officer, laughing, said, "this one is a slut, judge." They both laughed, and, without warning, the officer stuck it to the end in a single thrust. As I screamed, I felt the judge's dick deep on my throat, and I heard them say, "shut up slut." At that moment, I almost came. I always had the fantasy of being fucked that way. It didn't go away for a long time, and I came like crazy, but I didn't stop sucking. The officer cum inside me, and shortly after, the officer took his dick out and cum on my face.

Some cum fell into my mouth, and I swallowed it. Then, when I tried to clean my face, the officer grabbed my wrists and now cuffed them behind my back, and the judge lifted my pants. So there I was with cum running down my cunt, and my face was full of cum, even a little bit running down my chin. At that point, the officer took me back to the audience by the arm. What a shame to walk like that and be in the court cage with cum on my face in front of other people. The judge said, "Apparently, the inmate can stay together with others. However, right after breakfast, she must come to my room every day for inquiry. She goes to solitary confinement if I feel she's a danger to the other inmates. And during the day, she will be working in the maintenance along with the other inmates". I kept thinking, "I'll come every day for inspection. I know well what inspection that will be. And what is maintenance? What awaits me in the following days?"


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