By Wakeysub

About six weeks before the holiday, a package arrived with a note saying that I shouldn’t open it until instructed in the session. On that night’s call, I reported that the box had arrived, and he smiled and said that was good because it meant I could be fitted for my island chastity. He explained that all slaves on the Island wore a custom chastity managed by the resort. The box contained everything I would need to do the sizing. He told me that he had an extra special chastity planned for me, which he was sure I would appreciate. As a first step, He instructed me to remove my chastity and my PA. He told me that my pubes would have to be removed.

On the Island, all slaves are displayed without pubes as it showed off the chastity to the maximum effect. He told me he had included a bottle of his preferred depilatory spray in the package. You just sprayed it on, waited for 10 minutes, and wiped the hair away. I thought back to a conversation we had had about hair removal when we were discussing activities. I’d told him then about how I loved the idea of chemical hair removal – how it was so much more mechanical and impersonal than a shaving scene. I found the bottle.

He instructed me to spray this liberally over my pubes. I could feel a burning sensation as the spray worked. It felt like the liquid was burning the hair away. After 10 minutes, he told me to use a towel to wipe it all off. This spray was highly effective as it had managed to remove all hair traces, including the roots. He nodded and instructed me that I was to use the spray twice a week until the holiday.

The sizing took the form of a kit that took an impression of my cock and balls – it was the sort of goo that they use to make dental impressions. The kit consisted of a cylinder slightly longer than my cock, a powder packet, and a bottle of liquid. He laughed and said that he didn’t have to tell me to get hard as he could see my cock throbbing in front of him. The last step before the sizing was to take the band provided in the kit and wrap it around my cock and balls, so it held everything tightly in place – this would also determine the circumference of the ball ring which sat at the back of the chastity. I mixed the powder and the liquid in the cylinder. When instructed, I lay down on top of the cylinder. My cock and balls were buried in the goo as far as possible. He told me to reach down and make sure that my balls were buried in the goo.

I reached under and did as I was told. I lay there for 10 minutes with my cock still throbbing hard in the goo. I felt it get progressively warmer, then it slowly cooled. At the end of the 10 minutes, he told me to slowly pull my cock and balls out of the tube. Now it was clear to me why I needed to be smooth for this – trying to withdraw from the gel if any hairs embedded would have run the risk of scalping me. My balls were firmly buried in the now solid gel. I pulled back, and it hurt like hell. He told me to take it slowly as it was essential that I didn’t damage the impression. My cock reacted to the pressure on my balls and started to shrink, retracting from the mould. Finally, I got my balls out of their respective holes, and the impression was free. He told me to cut the band behind my balls so the band’s size would be retained. After I had refitted my PA and chastity, I boxed up the cylinder and the band that had secured my cock and balls and posted them back to the PO Box number He provided.

For weeks all I could think of was my forthcoming trip. I looked forward to my frequent chats with IslandMasterUK. He seemed to have an endless supply of images. The discussions got hotter and hotter as he questioned me on my fantasies in more and more detail. The more we talked, the hornier I got and the more extreme my stories became. My cock just got harder and harder and strained at the bars of my chastity.

Exactly a month before I was due to set off on my trip, another small package arrived. I opened it, there was a black bag secured with a cable tie and a note from IslandMasterUK telling me not to open this bag until instructed. This must be the chastity device that I had done all the sizing for a couple of weeks before. The note went on to tell me that I would need a glass full of ice water and the pliers to remove my PA available next to me during the call.

At the agreed time, I presented myself in front of the camera kneeling as required. The app buzzed, and I clicked to open the chat with IslandMasterUK. He asked if I had received his present – I confirmed I had and thanked him for the gift, He laughed and said that I should wait to thank him until after saw what he had got me. He told me to open the bag. I carefully cut the tie and poured the contents onto the floor in front of me. There were 3 sealed packages – one marked ring, one marked PA, and one marked cage.

As I didn’t have a keyholder, my chastity so far was self-imposed. I had been caged for the last 6 months. To prevent prostate problems, I incorporated a monthly release into my programme. The ideal would have been to find a Master who would restrain me and milk my prostate – this was one of the many fantasies I discussed at length with IslandMasterUK in one of our sessions. I was left with no choice but to remove the cage once a month and drain my balls. So, although I was locked away, I still had the keys, and every month I knew that my balls would be emptied. I had tried to follow my rules – when I wanked it wasn’t to porn, I worked to make it as emotionless and mechanical as possible. I just went into the shower, removed the cage, pumped away on my cock. As soon as I spurted cum, I sprayed my crotch with icy cold water and refitted the cage quickly. A couple of years ago, I decided to get circumcised. Although I preferred the look the main reason for getting cut was that it was a lot more appropriate for chastity to not have all that excess skin inside the cage to trap dirt and smells.

Suddenly I realised that He was talking to me. I was still staring at the 3 black packages in front of me. He told me that this was a custom device made specifically to meet my needs. He acknowledged that my Holy Trainer featured a wire-based anti-pull-out, and it worked well and stopped even my cock from pulling back out to the cage. He said his design was taking this security requirement to a whole new level. He told me to remove my existing cage and put it to one side as I wouldn’t be needing it again. My hands were shaking as I undid the cage, removed the wire loop, which secured my PA when I was wearing it and pulled my cock clear of the cage. It was rock hard. The ring round my balls was still in place. This ring hadn’t been removed since I started wearing the chastity six months ago as I left it in place when I wanked. It made refitting the cage after cumming a lot quicker.

I pushed back on my shaft and managed to get it back through the cock ring, my balls quickly followed. For the first time in six months, I was wearing nothing around my cock and balls. I don’t remember my cock ever looking this big before. I hadn’t seen it without the pubes for a long time, I think that just made it look bigger. Looking at the screen, I could see him smiling and nodding – next to go, the PA. The one I wear in my Holy Trainer is a small segment ring, part of the ring can be removed with pliers allowing it to be fitted or removed. I took the pliers and put them into the ring and squeezed gently to release the locked segment. The section pinged free. After that, removing the ring was easy as you just rotate it until the open part is aligned with the piercing hole and then it comes free.

He told me to open the package with the new cock ring – it was heavier than it looked, and it was hinged at the base so it could be much smaller than one I had on my Holy Trainer which had to be big enough to fit my balls through when I put it on. It was also moulded to cup my balls. Two short machined pins were incorporated – one at the base which would separate my balls and a second at the top. These were obviously to secure the two parts of the cage together. It was an impressive device. The ring looked smaller than the one on my Holy Trainer. He told me he wanted me to look into his eyes as I fitted the ring as he wanted to judge my responses immediately. The design of the ring meant I didn’t have to look at it during the fitting. The base plate had the two definite impressions to cup my balls, my cock naturally aligned as I closed the ring. I couldn’t take my eyes off him as he smiled at me. As I pushed the two halves of the ring together, I was shocked when I heard a loud click. He smiled and just said “security” The fit felt perfect – It was a tight fit but not enough to do any damage. It was impossible to even see any joins and no sign of a keyhole or any way to release it. He saw my puzzled look and told me that you needed special tools to open this cage. I already loved the fit of the ring.

He told me how impressed he was with the fit and how this chastity would be critical to achieving my dreams on the Island. He told me it was time to fit the PA attachment that he has designed specifically for me. He told me to open the PA packet. Inside I found a small metal component I ran it between my fingers – it felt solid – a small plate with a rounded bar bent with a pronounced S at the end. The top of the plate was contoured like the underside of my cock. It was slightly tacky like it had some sort of glue on it. This really was a custom fit. The bottom of the plate was machined so it could be inserted into a suitable slot. The bar was about 2 cm long and was a significantly larger gauge than my existing ring. I had worn a larger ring in my PA in the past, so I was confident that it would fit. I had seen similar PA attachments in chastity devices before, but this one looked more impressive. The profile of the rod looked interesting. The body was profiled like a taper – at the point, it had a diameter of about 4mm, it progressively widened until it got to about 8 mm. I had once told Him about my dream of upsizing my PA – I made it to 6mm previously. I had downsized to a smaller ring to fit with the Holy Trainer.

What made it intriguing was that the taper had been bent through 90 degrees a few millimetres from the end. It had been machined, so the diameter went suddenly from 8mm to 2mm. The 2 mm section continued for a couple of millimetres before increasing to 8 mm again where it connected to the base plate. I could imagine the hole for my piercing stretching to accommodate the widening rod and then closing tightly into the tapered section – once this was on it was going to be a really secure fit.

I was nervous –I love chastity, but am I ready for this?

I saw His handsome face smiling back at me from the screen. He reassured me that the only thing stopping me living all my fantasies was the fitting of this chastity. He told me that he would have loved to restrain me and fit the chastity for me.

I knew then that I would have to do it – I had to make him happy and proud. A small black tube marked lube had fallen out of the package. I applied it liberally to the rod and to the underside of my cock focussing on the piercing site. I lined the attachment up with the hole in the base of my cock. He instructed me to look into his eyes as I fitted it as it would be a life-changing event. I stared longingly at the screen – I would do anything to please the man. I lined up the rod and started pushing it gently forward. I felt it slowly opening the piercing and making its way through. I stared deep into his eyes and heard his encouragement. I felt the resistance increase as the tube got progressively bigger. I winced as the pain in my piercing increased. I maintained a constant pressure, it felt like it was going to tear. Suddenly all the resistance was gone, and it had popped into place. Looking at the bottom of my cock the piercing hole was no longer visible – the 2mm section of the rod ensured that the fixing plate had locked itself firmly into the piercing and was now effectively riveted to my cock from the inside.

The plate had fixed itself to the underside of my cock Looking at the piss slit, there was a small length of rod protruding. I looked at the screen and saw IslandMasterUK smiling at me. He told me that he was so proud of me. I knew I had to fit the chastity for Him. There was no chance of removing the fixing plate now without surgical intervention. I had already committed to going all the way. I really didn’t care – I was so horny, and I just had to get my cock into the chastity that He had given me, that He wanted me to wear. It suddenly struck me that my cock was now permanently fitted with a sound – another of the topics we had discussed. I had only ever tried sounding combined with electro. I squeezed the head of my cock, I could feel the solid metal core inside the cock head. He smiled again and said, “Oh yes, perfection.”

Then it was time for the ice – by this time, the glass was more than half full of ice and ice water. He told me to push my cock into it and hold it there until my cock was soft and numb. I started to think of everything non-sexual I could. Willing my cock to soften so I could get it into its new cage. I don’t know how many minutes it took, but eventually I pulled out of the ice-cold water. My cock was so shrivelled and tiny – it now looked a lot more like the cock which would fit into the new cage.

He instructed me to open the final package and position it over my cock. Again, he told me to look into his eyes as I fitted it. I didn’t even have to look at the cage. I just held it in my hand and moved it in towards my shrivelled cock. The PA plate located itself in a track in the bottom of the cage. I guided it forward until I heard a familiar click. I pulled back slightly, there was no give, the plate had locked itself firmly in place. He nodded at me, told me he was so proud of me, and encouraged me to take the final step and show him that I was committed to this and wanted to achieve this as much as he wanted me to achieve it. I could feel my cock starting to reharden. I had no choice but to push the cage back towards the cock ring, lining up the bars at the top and the bottom. Both pins aligned perfectly and locked with a loud click For the first time, my cock was locked in a cage which I had no access to. This cage didn’t have any “Get out of Jail” option – my cock was firmly locked into this cage. There was no way for me to get out of it until my holiday. I felt my cock hardening in its cage, and I felt short fine pins lining the cage’s head for the first time. There were pins all around my cock head. As I got harder, they were driven into the tender flesh.

He smiled “Oh – I added those because I knew you’d love them. You have to admit that it looks phenomenal. I am so proud of you. I can guarantee that that you will live ALL your fantasies when you come to the Island.

I agreed with him that it looked phenomenal and that I was so grateful for him giving this to me. He smiled. I told him I couldn’t wait to get to the Island, and he said that he couldn’t wait for me to arrive.

My hand went to the cage around my cock, and it felt so solid and secure. My cock was encased in metal, even the cage’s piss slit was closed with a mesh. I had no way to touch it.

Wakeysub 2021

To be continued …