By Wakeysub

[Please remember that EVERYTHING that happens on the Island is consensual. Although the use of safewords has consequences on the Island, they are always observed. If the situation called for it, the safeword would stop the scene. The fact that the slave would be rendered unconscious and would have to be carried away on a stretcher is academic. All limits have been agreed on upfront and are strictly observed. The slave in the story had long, detailed conversations with IslandMasterUK during which he was able to draw out all the slaves deeply hidden fantasies and part of the joy of the Island is that it is a “safe” environment where all these fantasies can be realised. Had the slave in our story not been so naïve (or horny and frustrated) he might have been a lot more prescriptive in his limits – but then again, where would the fun be in that? The limits we are seeing played out are the ones which drove the slave’s fantasies in the discussions.

I hope you are enjoying the story – it’s great to get your feedback either here or on my Recon account. If you have any suggestions for where the story should go let me know. After all – he signed up for a four-week holiday and we are only on the second day!!]

Master West leaned forward and clipped the leash onto my collar and disconnected the dildo cord. A yank on the lead pulled me backwards. I struggled to stand and follow him. My jaw ached, and I moved it from side to side to relieve my joints’ stiffness.

He walked quickly across the clearing towards the largest of the buildings. The door was open. We walked straight inside. It was a large room which appeared to have been furnished like a Spanish Inquisition dungeon. Around the walls were narrow cages about 2 metres tall mounted about a metre off the ground. Hooks were hanging from the ceiling. Free-standing frames which looked like they would effectively restrain and expose anyone attached to them were arranged around the room. Hanging from the roof beams were cables with hooks attached. I shivered thinking what activities this room could be used for. My cock started to harden inside its tight prison. My cock head ground back into the pins, just making it get harder.

He dragged me forward towards a heavy-looking metal frame set in the middle of the room. It looked like a St Andrews Cross where the legs had been bent just before the cross’s two lower legs joined. He positioned me at the foot and squatted down to connect my right ankle and then my left to fixing points at the base. My legs were spread wide apart. He put his hand a pushed me forward until my body was lying on the frame. He moved around, keeping his weight on the hand still firmly pressed into my shoulder. He gripped my wrist with his hand and pulled my arm outwards and then fixing it to the restraint point with a snap. My left wrist was more of a struggle to attach. He had to use all his strength to stretch my arm and align my body on the frame. I thought he would rip my arm out of joint and I was relieved when I heard the click as the last restraint locked in place. He knelt next to my head.

“768, you are the main attraction tonight. I can’t believe that you have never been fucked, you sad fucker. Well, tonight that’s going to be fixed once and for all. Your virgin hole is going to be auctioned off to the highest bidder. When the winner has spent a small fortune for the chance to take your virginity, he will make sure that taking his prize is an experience you NEVER forget. I’ve been careful to make sure that your ass hasn’t been touched since you arrived, so you are as tight as possible. Tonight, your sorry hole will be dripping with cum. It will be stretched beyond your wildest imagination. When he’s finished with your ass, you can expect him to want to fuck your other hole. A word of warning – if he feels a single tooth, you will regret it for the rest of your days. That’s you all set -and it’s only 2 hours until the guests arrive.”

He placed a blindfold over my eyes, plunging me into blackness. He smacked me hard on the right asscheek. I tried to imagine what I looked like – spread wide, fully exposed, hairless and marked. How the fuck had I let myself get into this situation – this was only my first full day here. My whole life was turned upside down. I struggled in vain to try and get comfortable. There was no slack in any of my limbs. The only part of me that was still free to move was my head to lift it up, but with the blindfold fit, it would have been a pointless exercise.

Time passed slowly. I found myself closing my eyes and resting on the frame even though it was an uncomfortable position. I was aware of other people moving in the room around me. I heard the sound of metal doors being closed and locked. I assumed that something was happening with the cages around the room. Suddenly there was a crash off to my right. I heard a scream. The screaming just seemed to go on and on. I could hear a stern voice saying, “useless fuck.” I imagined that one of the slaves had broken a rule and was being zapped by his collar. The most disturbing thing was the fact that his screaming just seemed to go on and on. Then silence. The silence seemed more ominous than the screaming – where was the sobbing, the whimpering, the crying? I heard the sound of another door slamming shut and the lock clicking.

“You’ll PAY for that you pathetic cunt.” The menace in the voice filled me with dread.

The noise of preparations continued around me. Occasionally, I was conscious of people brushing past me. Touching my legs or arms as they moved past. Some were dressed, others were naked. I felt ever more exposed in this large room.

Suddenly I was aware of a sensation in the tube of my chastity. I’ve played with electricity on my cock before, so I recognised the feeling of a program stimulating my cock. It was an intense rolling sensation which started close to my balls and drew its way down my cock. My cock was being slowly milked. The effect of this was to make me increasingly horny and encouraged the blood into my caged cock head, causing it to swell and drive the pins deeper and deeper. As I moaned softly, I felt my collar tingle. Struggling to not make a sound it continued to milk my cock. The levels had been perfectly judged. There was no prospect of any release, but it just carried on. I started to thrust my cock forward to try and increase the stimulation of the milking. I didn’t care about the pins I was just desperate to cum. It had been so long since I was last able to drain my balls.

The cage seemed to sense my heightened stimulation. It adjusted the strength to ensure that I was so close to the edge. There was no way of cumming. No release. I was so close. I could feel my balls stirring. I was going to be able to overcome the chastity. I willed myself to cum. I had to cum. I was sure that I could do it. I humped furiously. So close. Any second. One more thrust and I’ll be there.

Suddenly an intense pain hit both my balls simultaneously. It felt like someone had hammered two red hot nails through my balls. So intense. My cock withered in its cage. I grunted; the collar tingled. I had discovered another feature of the cage. It must have detected that I was close to cumming. The milking sensation started again, and the process restarted. I was just getting hornier and hornier.

The room was beginning to fill up – the sound of chattering got louder as the number of men increased. There were people stood around me. The occasional hand ran across my back, side and ass cheeks.

“Got a proper fat pig here.”

“He’s going to squeal so bad tonight. He’ll regret that.”

“His ass looks good and tight.” I felt a finger running down my asscrack and pushing gently at my hole.

“Fuck, he really is virgin. I haven’t seen a hole this tight for years. Someone is going to have so much fun wrecking this tonight.”

“They’ll have to carry him out at the end of the night when his ass is pumped full cum.”

“I just want the chance to suck a few loads out of that tight hole.”

“Most likely they will just ram a plug in his hole and leave him here for the night to stew in his own juices. Fuck, look the horny bastard is fucking the table. He must be excited about what is cumming tonight. I’m going to put a bid in for that hole. Mind you, I’d love to see him bred by one of the 12″ cock brigade. The thought of his tight hole being stretched and torn by one of those massive rods would be so hot. Shit, my cock is throbbing already – either way, I’m going to have to find myself some tight slave ass tonight.”

He pushed his finger into my hole, causing me to moan slightly. He pulled out and smacked me hard on the ass.

The crowd’s noise increased, and I was aware that more and more people were standing around me and touching my body. I felt glasses and plates being rested on my back. I felt a lot of fingers running along my asscrack and testing the tightness of my hole. It reminded me of inspecting the cattle market animals to make sure they are up to scratch. The occasional finger got pushed into my hole. They were always small and barely pushed in at all.

There was a loudspeaker announcement. I recognised the voice of IslandMasterUK. My cock throbbed in its cage, intensifying the milking sensation.

“Welcome to the Island for our weekly meet. Tonight, we have a special attraction as we will be auctioning our new slave, 768’s virginity. I know it’s hard to believe that a 54-year-old gay cunt could still be virgin. From talking to him and many of his contacts, I am prepared to guarantee that his hole is virgin tight. He confided in me that he had never been able to take anything larger than the thinnest plug without being overcome with pain. I am sure we will all help him get past the pain barrier tonight, gentlemen.”

There was general laughing and conversation. A hand slapped me hard on the cheek.

“All funds raised from the sale of his virgin tight hole will go towards the maintenance of the club. We are always looking for new equipment for you to use on the slaves. The more we raise, the more fun you can expect in the future. Now, this truly is a once in a lifetime experience. How often do you get the chance to fuck a virgin ass with no consideration for the bottom? 768 told me he wanted it to be a memorable event when he was fucked for the first time. I am sure we can guarantee that can’t we?” There was a ripple of applause around the room with shouts of “fuck yeah.”

“So, what am I bid?”

I could hear men shouting number all around me. The longer it went on, the more excited the bidding seemed to get. I couldn’t focus enough to listen to the state of the bidding with the hands running over my body and my cock still being milked by the chastity cage. The number of people bidding started to diminish, and eventually, it was down to two voices on either side of the room. Almost as soon as one would call out a number, the other one would increase the bid. This went on for some time. Neither of them seemed prepared to accept that he had lost out. Then it was over.

“Sold, the ass is yours.” IslandMasterUK shouted. “I know you need no encouragement to make it memorable. Having seen your cock in action before, this is a sight I would happily pay to see myself.

Even with the blindfold in place, I could feel the people around me moving to get a better view of what was about to happen. I felt a pair of strong hands fondling my ass. They were kneading my ass. Rolling and spreading my cheeks. The first spank took me by surprise. He had massive hands and force from his spanking drove me hard into the frame. I lost count when he got to 10 strikes. It was all I could do to stop myself from screaming. I was terrified of being zapped by my collar. I knew that with all my muscles stretched as they were, it would be absolute agony when they tried to spasm.

I felt his body pushing down on my back as he leant in over me. He whispered in my ear.

“My gorgeous fuckpig- I’m going to make you squeal and squeal for everyone in the room to hear. Your tight little hole is going to feel so good around my 11-inch prick. I’m going to be kind and lube my cock because I don’t want you fucking damaging it. Don’t worry though I’m going to make sure you never forget tonight.”

Even as he leant over me, I could feel his massive throbbing cock pushing at my asshole. He placed his hands on my shoulders and gripped tightly. He drove forwards. My ass was tight. I tensed as he started to drive in.

“Open you fat bastard.” He gripped my shoulder tighter and shouted in my ear.

The pressure at my hole increased. Despite myself I tensed My asshole squeezed tightly closed. I could feel his throbbing cock pushing at my hole. It hurt like hell as he drove himself into my hole, pulling on my shoulders to force himself into me. I knew that I had to try and relax my hole if he wasn’t going to tear me apart. My brain no longer had control. He drew back slightly and rammed forwards. His cock was slick with lube and precum. He pushed firmly against my hole. Finally, I felt him sliding inside. The pain was indescribable as he pulled himself deeper and deeper.

I cried out; the collar zapped me. It was at a low level. With the pain I felt in my ass, any sensation from the collar was paled into insignificance. I felt him slide deeper and deeper. The pain just got more and more intense. I was convinced that my asshole had been ripped by the massive cock. There was no way that my ass could stretch that much. He let go of my shoulders, I felt his hands grip me at my waist. He pulled back slowly and then rammed back in quickly. He drove me into the frame. The milking sensation in my cock increased nearly matching his thrusts. My balls were being zapped frequently by the cage. The pain was so severe. He was pulling all the way out now and pushing his cock deep inside with a single thrust. I tried to squeeze my hole to keep him from hurting me so much. He laughed.

“The sad fuckers trying to grab my cock – he obviously doesn’t want this to ever finish.”

He kept on thrusting, I grunted and screamed with each thrust. He grabbed my hair and pulled my head back as he buried his cock deep in my guts. I could feel his cock pulsing as he pumped his load into my ass. He held in place with his cock buried deep in my destroyed hole. He slumped back down on my back. I felt his weight on top of me, pressing me down. I heard men’s voices all around me, commenting on his performance and staking a claim to use my hole later in the evening. I felt him lift off me and my ass felt suddenly empty. I could feel his cum dripping out of my hole. A tongue pressed itself to my hole. I felt someone pressing their face into my asscrack. Someone started lapping at my hole. Pressing their tongue into my ravaged hole trying to get every drop of his cum. He had moved round in front of me and lifted my head by firmly gripping my hair and pulling it back to lift my head.

He slapped me across the face with his shit-stained, slick cock. The men crowded around him were laughing as he moved it back and forth.

“Mouth.

I instinctively opened my mouth. He pushed his stinking, sticky cock into my mouth. Even when I gagged, he continued to lunge forward. I struggled to handle his massive cock. He knew how to position his cock to make me gag with every thrust. He pulled it out of my mouth.

“Lick”

I put out my tongue and carefully licked the head of his cut cock. It smelt and tasted disgusting. My ass hadn’t been cleaned before I was fucked, so I licked off a mixture of my ass and his fluids. He gripped my hair tightly and used his grip to make sure I was doing a good job. The tongue at my ass was driving deeper and deeper. As he pulled out, I felt another cock pushing at my hole. The second cock was big but not as big as the first. He pushed in dry using the remainder of the cum in my hole as his only lube. He pumped slowly and steadily as I focussed on cleaning the cock in front of me. The Fucker was obviously frustrated that I wasn’t reacting enough to his fucking. He pulled right out and pounded home, driving the cock deep inside like a pile driver. Each thrust made me moan, causing my collar to start issuing small shocks.

I lost count of how many times I got fucked that night. After each of the fuckers had cum, I would feel the tongue pushing into my hole and drawing the cum from inside me. I don’t know whether it was the same person each time or whether there was a group who were getting off on eating the cum out of a wrecked hole.

A large cock was rammed into my mouth for cleaning when I felt the flogger on my ass. It was swung with full force and the strands wrapped around when it hit. It hurt like hell. I would have cried out if it wasn’t for the cock rammed down my throat. On the sixth stroke, they changed the angle, so the strands struck me on the balls. It took me by surprise. My balls were so full and tender. As a reflex action, I closed my mouth. Biting down and catching the cock head with my teeth. The cock withdrew quickly from my mouth. He gripped my hair firmly and lifted my head. He slapped me hard on the cheek, I saw stars.

“The fucker bit me. The fucker bit me.”

I wanted to say sorry. I got no more than the first syllable out of my mouth before my collar exploded. Every muscle in my body seemed to go into spasm.

I could hear the heated voice of the owner of the cock and the more relaxed voice of IslandMasterUK. The former demanded that I be punished for abusing a top and that it should be a punishment I never forgot. IslandMasterUK assured him that he would take care of it and that I would never bite another cock. This seemed to appease the cock owner. When IslandMasterUK told him that it would all be fixed before his next visit, he seemed happy. When he was told that he would have free rein to use me as he wished on the next visit, he was positively purring.

Master West started speaking in my ear.

“768 – you fuckwit. What did I tell you about biting? We will have to make sure it will NEVER happen again.”

He slipped a pecker gag into my mouth, ignoring my attempts to gag. I felt him pulling on the straps and the familiar click of the padlock.

I felt another cock pushing at my torn asshole. He glided in smoothly on the cum from all the previous users of the hole. I couldn’t believe the difference between that first cock which had hurt so badly when it ripped open my hole, and now my hole was so abused you could drive a lorry into it.

I felt him thrusting inside me and adding his load to the collection.

As he pulled out, I felt pressure at my ass as a large butt plug was pushed into place. Despite everything I moaned into the gag as my hole stretched wider and wider until it hit the widest part of the plug and my hole gripped the neck of the plug holding it firmly in place.

I felt the restraints release and a yank at my collar pulled me up and dragged me staggering blindly out of the crowded room. He moved quickly, I followed, stumbling to keep up. I heard the sound of a heavy door opening. The blindfold was removed. I was back in the cell again.

“In.”

I climbed in and lay in the required position. As soon as restraints made contact, they locked in place. When he was happy that I was fully restrained he fitted the headphones. The cage door closed with a loud click. The familiar, comforting sound of waves started playing loudly in the headphones. I relaxed despite the pain in my ass and the gag rammed down my throat. Before the door closed and the lights went off, I had descended into a deep hypnotic sleep.

Wakeysub 2021

To be continued …