By Wakeysub

For the next month, all I could think about was my trip to the Island. My day to day work became secondary – I lived for my now nightly extended chats with IslandMasterUK. The more we chatted, the more comfortable I felt, the more open I was about my fantasies. By this stage, I think he knew more about what made me horny than I did. He took great delight in getting me as excited as possible every night as he encouraged me to explain in intricate details what I would expect from life as a slave. My cock was now constantly leaking pre-cum.

The days slowly ticked by and then I got the email with the train ticket attached, only the outbound leg was attached. I pulled up the map and found the station. It was a small isolated station on the mainline from London to the south coast. I couldn’t imagine that it was going to be very busy. It was a through ticket, so it covered the complete journey from my local station, the underground, and the train to the south coast. Everything was covered. The email also detailed what I was to wear for the journey – a jockstrap, jogging bottoms, a plain white t-shirt, white trainer socks, and trainers. The only possession I was allowed to travel with was my house key. That was it – no money, no wallet, no phone, nothing. My train journey would be close to 5 hours.

Early in the week, I received a blood test kit – several small plastic vials I had to fill by stabbing my finger with a spring-loaded lancet. I had done this before as I tested for HIV every 6 months even though my sexual contact was minimal. The accompanying note said that the results of the tests would be delivered directly to the Island. All I had to do was fill the 3 vials to the line with blood and post it off. I was reassured that the Island was being responsible and ensuring that its guests were free of STI’s. I posted it the same day and received an email 3 days later from IslandMasterUK confirming that I had a clean bill of health. He instructed me to refrain from sexual contact of any sort with anyone until I arrived at the Island. Given my track record, I didn’t see that that represented a problem.

The following day a large envelope arrived. When I opened it, I found a very detailed contract detailing duties, responsibilities, roles, and rights. An appendix documented my limits – these were broken into the group we discussed in the preparatory chats. The first group was hard limits – things I wouldn’t be prepared to do – children, women, snuff, etc. The second group contained my “Must Have” limits – this covered my requirements for chastity and that I am to be treated as a slave for the duration of my stay. The third group consisted of a list of activities I had discussed with IslandMasterUK. Against each, there was an indication of my experience and my current limit.

Finally, a clause stated that I had willingly agreed that the third group’s limits could be varied by Him or his nominated representative solely at his discretion. Similarly, any other activities not explicitly covered by one of the three groups would be seen as group three. It was a long and detailed document written by a lawyer given the amount of legalese. I found myself skimming large parts of it. The safeword arrangements were documented at length in another appendix. The instructions said that I should initial each page to confirm that I had read it.

The last page of the document was an innocent-looking sheet that contained a series of clauses stating that I had read the contract, that I was agreed to abide by the agreement, that I was aware that once I entered into the agreement I did not have the right to cancel or withdraw from the contract, that I had no right to terminate the agreement, that I was sane and that I was signing the document of my own free will. It looked like any other agreement document. The signature had to be witnessed. The layout of the page meant I could get it witnessed without sharing the contents of the contract with them or telling them what it related to. My hand was shaking when I took the envelope with the contract document to the post office to send it back to Him. It made it even more real. Two days later IslandMasterUK confirmed in our chat that he had received the contract and that he was pleased to see there were no changes from my side and that I was happy to go with what was proposed. I confessed that the thought of asking for any changes to the document had never even entered my head.

The night before my trip, I was anxious, it hit me that I didn’t know what I had let myself in for. I was going all that way without any money in my pocket. Something inside me reassured me that everything would be okay. The chastity helped me here too. This was an expensive custom device. By supplying it, He was demonstrating his commitment to me. I had to also do my part. Besides, there was no way for me to remove the cage without his assistance so, if I didn’t meet up with Him, then any chances of me ever touching my cock or stopping the pins driving into the head are gone. I listened to my conditioning programme, in seconds I was asleep

I was stood on the platform 45 minutes before the train was due to arrive at 10am. No way was I going to miss this train. I got onto the train and took my seat – I looked around the carriage and wondered whether anyone else on the train was off on a similar voyage. The train pulled away with a lurch, it hit me that I was committed –as I moved further and further from home, I got closer and closer to living my fantasies. The journey was so dull, but we were travelling quickly now moving closer and closer to London.

It was nearly 2 months now since my balls were last drained. This meant that I was permanently horny – I killed time by looking around the carriage and imagining that some of the other hot looking men on the train were on the same journey as me. I visualised what they would look like stripped and restrained. This just made me more and more frustrated. The chastity reminded me of its presence as my swollen cockhead ground into the pins. Finally, we pulled into London. The platform clock said the train was on time. I stood carefully making sure that I didn’t jar my cock cage and made my way to the door. I stepped down onto the platform along with the hundreds of people who were on the train with me.

I went straight to the underground platform to get the tube to Waterloo. I don’t have a good track record with cross-London transfers, so my sole focus was to get to Waterloo. The first tube train arrived, and it was packed. I pushed on as I didn’t want to risk waiting for the next train. I ended up stood hanging from a rail by the door. As we pulled into one of the stations, I felt the hand of another passenger casually brush against my cock. I dismissed it as an accident, but they obviously felt the outline of my cage as the hand returned and started to carefully trace the edges of the cage with his fingers. The crowd on the train meant that nobody could see this happening and I wouldn’t have moved even if I had been able to.

I looked up and into the knowing face of a well dressed, handsome man. He kept rubbing his hands over the cage for a few minutes as he looked into my eyes and then he gave my nuts an extra squeeze and then whispered – “Nice package”. I blushed, but my cock reacted in its cage. I winced as the pins went to work. The tube pulled into Waterloo, and I rode the escalators up to the mainline station.

My train had just been put on the board – it was leaving in 15 minutes, but as I didn’t have anything else to do, so I got on board and found my reserved seat. A screen in the carriage listed the stations this train was scheduled to call at. I was relieved to see that the train was express to Southampton, so at least that part of the trip would be as quickly as possible. My station was marked as a request stop on this train – I was right, this was going to be a quiet station. I needed to tell the conductor that I wanted the train to stop. Otherwise, we would just zoom through. I played my game of imagining that the hot men in the carriage were on the same journey as me – there must be a better chance of someone else going to the same destination on this train. There were a couple of blokes sat around the carriage in white t-shirts. No way of knowing if they were on the same journey as me. Imagining them wearing a chastity like mine just made my cock swell in its cage. The screen said we left in 3 minutes.

A whistle blew on the platform, and the doors closed automatically. This was getting very real now. The train pulled away steadily, it was actually happening. We sped south – the conductor wouldn’t come around until after Southampton. I spent my time looking out of the window trying to imagine what was going to happen to me – it struck me that in all our conversations IslandMasterUK had never actually said what would happen as part of my holiday. I had shared so many of my fantasies. If only the smallest part of them came true, then it would be unbelievable. I realise that I’ve not told anyone where I’ve gone but what would I tell them anyway – I don’t know where I’m going, I don’t even know the name of the man I’m meeting up with. Am I mad? I trusted him! I trusted him enough to appear naked and exposed nightly in front of my webcam.

I trusted him enough to lock my cock away in a chastity device, which I am confident I could never release without the keys that he holds. I could get off at the next station and make a phone call. I could go home and forget it all – except for the solid metal cage on my cock. He is offering me everything I’ve ever dreamed of. For that opportunity, I have to push forward. My mind was spinning, and my panic levels were increasing. There was an announcement over the speaker that we were approaching Southampton. It was like a switch was flipped inside me. Suddenly my confidence levels increased, I knew that I HAD to go through with it.

A comforting voice in my head started to tell me that if I ever wanted to be happy again, I had to go through it. I ached for Him to touch me, to be with him. The only way to do that was to push ahead. The train started to slow down, and we pulled into Southampton. Quite a few people got out of the carriage, including one of the blokes in the white t-shirts. There goes that idea. The overhead display listed the stops and showed 10 stops before my station—an hour to go. I shuffle in the seat again and look around. I see the conductor coming round checking the tickets. I get mine out of my pocket. He looks at my ticket and confirms the station’s name, and he tells me that he will let the driver know as I am the only one getting off. This was disappointing, I had hoped that I wouldn’t be the only one disembarking.

He smiles at me, I convince myself that he knows why I’m going there and that I now have a neon sign above my head saying that I’m off to become a slave. I close my eyes, the voice in my head just gets more compelling. I realise that the voice I am hearing is His and it is reassuring. I feel his hands pushing me back into my chair harder and harder. The voice is repeating a mantra that seems so familiar and comforting- I was born to be a slave, I will only be happy when I live as a slave, the Island is the place where I can live as a slave. My lips moved in time to the mantra. Anyone looking at me in the carriage would have thought there was something wrong with me. The carriage speaker announces that we are approaching my station – I have no idea what happened to the time as it literally sped by. What will be waiting for me at the station?

As we start slowing down approaching the station, I move towards the door – I am desperate to get off the train now. The doors open, I step out onto the platform, the doors close behind me and the train pulls away silently. I look left and right – I am alone on the platform.

At the far end, I see a ramp to the car park. There are a couple of men standing watching me. They are both tall and solidly built– well over 6 feet. I move towards the end of the platform. As I approach one of them comes up to me and says my first name, the other smiles when I nod my head. The man who said my name says one word “Key” and holds his hand out. I feel into my pocket and hand over my key – my only possession in the world. He smiles and pockets it quickly He puts his hand on the back of my neck and forcibly guides me towards a white transit van with no windows in the rear portion which is parked in the furthest corner of the car park with nothing parked nearby – the side door is open.

As we move closer, I can see several seats in the centre of the van. He stops and tightens his grip holding me in place as the second man retrieves a box from inside the vehicle. He set the box down at my feet and gets to work. He wrapped a chain around my waist, pulled it tight. A click indicated that it was padlocked in place. He grips my right wrist firmly, twisted it behind me. There must be handcuffs integrated into the waist belt as I feel the cuff ratcheting tightly around my wrist, holding it in place. My left wrist got the same treatment. Before I knew it, both of my hands were cuffed behind my back. The grip on the back of my neck pushed me downwards to make me bend my knees. I feel shackles being closed around my ankles. They are connected by a short chain with a second chain then running up to the waist chain.

The chain isn’t long enough to let me stand up straight, I have to squat. I’m turned and pushed forward towards the van door. I stumble and struggle to lift my leg high enough to get into the van. A push behind me ensures I get into the open door. The hand on the back of my neck guides me towards one of the seats and pushes me down in it. There is space in the seat to accommodate my hands and arms. It has shoulder straps that pull down and clip into a buckle connected to a crotch strap which he pulls from underneath. Lap belts are drawn from the side of the seat and these clip into the buckle as well. I feel firmly held in place on the seat. He reaches up and presses a button on the seat’s shoulder, I hear a whirring, and all of the straps tighten.

The guard stood behind me reaches forward. I see nothing as he fits a blindfold that blocks out all of the light. He laughs – “I’ve been told you need the pecker gag – you told them you struggled to swallow a cock, didn’t you?” I didn’t respond. I felt this large rubber cock head being firmly pushed into my mouth. I tried to use my tongue to expel the gag. It did no good, he just put his hand on the mouthpiece of the gag, and forced it in until it was sat deeply inside my mouth.

He seemed to take delight in pulling the strap on the gag tight. After he had given it a final pull, he buckled it closed. It was finished with a click as he padlocked it closed. My lips were stretched painfully around the cock head. I was panicking as I really couldn’t control my gag reflex. “One last thing to complete your isolation”. I felt him pushing something into my ear, everything appeared muffled. He patted me on the top of my head.

Wakeysub 2021

To be continued …