The Brick: Chapter 11

Disclaimer: This is complete fiction. Any resemblance to other works, or real people is purely coincidental.

Please note, the characters in my stories never wear condoms. This is because the sudden urge to play it safe doesn’t really fit in with the mood I’m trying to create. Do not take this as an endorsement for unprotected sex; please do not bareback without first making yourself aware of all the potential risks that are involved. My characters can’t get STI’s ‘cause I don’t want them too, but the real world doesn’t work that way.

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Stud stood outside my cell, waiting for me. We were to be seeing a client together today, which was apparently pretty rare. Smirk told me he’d never seen it happen while he’d been here. Being with another prisoner made me much less nervous about meeting a new client, but a whole new kind of worry came with having to perform with one of my ‘colleagues’. I was in the standard prison uniform jock, but Stud had been given leave to wear clothes he was comfortable in; apparently this client was familiar with him. Even with the permission, he’d still picked fairly revealing clothing – a pair of extremely tight lycra boxer briefs, dark blue and complete with a zip on the front, allowing easy access to his pierced cock. And an equally tight white vest top that showed off his modest but noticeable body tone, and the piercings in his nipple and bellybutton. “Ready?” He said with a grin. He had a shoulder bag hanging off his left shoulder.

I nodded as I walked out the gate. Immediately, he took me by the hips and pinned me against the bars, forcing his mouth against mine and shoving his tongue deep into my mouth. I tasted metal and felt the bump of a tongue stud as he explored every inch of my mouth he could, and two more bumps pressed against my lips from his snakebite piercings, though these ones had points on the ends making them hurt slightly. I rested my arms on his shoulders, quite happy to let him explore – I’d developed an enjoyment for people who kissed me deep and aggressively. Finally, he broke off the kiss and smiled at me. “Good.” He said, approvingly, explaining when I gave him a confused look. “This client likes using the same prisoners regularly.”

He turned to walk up to the office, bidding me to follow as he continued. “Do you know what we’re doing to today?” I shook my head at the question and he let me walk in front of him, leading the way to the private cell gates where I was told we’d be today. “Well,” He said and groped my bare ass cheek. “Let’s just say that this’ll be loosening up a bit more.” I turned around, wide eyed, but he just grinned as he walked ahead of me again. We headed down into the private cell corridor, and towards Studs cell where the client would be meeting us once we were set up. “I wanted to make sure we had some… ‘Chemistry’, in case he wants you to be the new regular; Buck used to be my partner for it, but he… Well, he started enjoying his fisting a bit too much and the client didn’t like how loose he got… You’ll see what I mean.”

Inside, there was a leather sling hanging from the ceiling. The first time I’d seen one, I thought it was some bizarre hammock, but I was soon set straight about its usage. Next to it was a small wooden table, and a little further away was a wooden chair that looked quite comfortable for a fold-away. “In you get.” He said with a smile and a slap on my bum. I walked forwards to the sling and turned so that my back was facing it, climbing up and laying back. The four chains that connected it to the ceiling each had a handle, two for my hands and two for my feet, which I put my respectively limbs in. Stud walked to the table that was now near my ass – my ass hanging at the level of ‘perfect access’. He pulled the bag off his shoulder and opened it up, beginning to pull things out.

First was a large bottle of what he told me was a very good quality lube. After that, a virtual rainbow of different coloured objects began to come out, all clearly designed for the same purpose; my ass. He rubbed my cheek with one hand as he continued removing the objects. “Don’t worry. I won’t be using EVERY one of them.” He grinned before letting go with another slap. They were in all different shapes and sizes, some so large I prayed that they were only for the novelty value, while others were much more agreeable. Some were perfectly smooth, others shaped to look like natural cocks, some had bumps and ridges and funny curves, and one that made me worry the most looked like it was supposed to be the end of a tentacle from some fantasy monster. “And the client knows you’ve only just lost your virginity, so he knows I’ll be starting small.”

The way he said ‘starting’ made me nervous, but I’d learned from the Warden, Smirk and Choke to have at least some faith in the people here and was sure Stud would be okay as well. I leaned back, resting my head on the sling as Stud finally emptied his bag and dropped it on the floor, then turned his attention to my ass. Speaking in a gentler voice, he said “I’ll get you loosened while we wait, yeah?” He rubbed his hands over my cheeks before slipping a finger down the middle and finding my hole. I gasped. One thing The Brick had taught me about myself was that any attention to that spot could instantly get me hardening, regardless of my nerves, especially when it was massaged as gently as Stud was doing now. He took the bottle of lube and coated his fingers in it, making it easy for him to slip one inside me while simultaneously making me whimper.

He found my sweet spot with incredible ease and began pressing against it, making me swell as hard as my jock would allow, before he worked in a second finger and then a third, easily managing to stretch me out. Eventually, he pulled his fingers out and picked up something from the table, applying lube to it and pressing it against my entrance. “Jus’ a li’l plug to keep you while we wait…” He said softly as he slipped it in. It was very little, feeling no longer than Studs fingers did, and only a little thicker. After moving it around inside me for a moment, Stud finally let go and, after wiping the lube off his hand with a cloth he had on the table, spent some time running his hands over my stomach and chest. He asked me if I’d ever thought about getting piercings and told me that he and the Warden could happily pierce any bit of skin on me if I wanted.

I was beginning to be tempted when the cell door opened. We both looked towards it to see a well dressed, older gentleman walk in and close the door behind him, smiling at us. His suit was a pewter grey, his hair was white and he had a moustache. Stud walked over to him as the man said his name, and wrapped an arm around the pierced boy, who leaned in and kissed the man on the cheek. Stud guided him over to me, and gently removed my plug again before allowing man to step up to me. I felt my nerves building but he only gently ran his hands over my ass cheeks and muttering some words of approval before taking me by the hips. He pressed himself against me and through his trousers I could feel an impressively sized hard cock. But he soon let me go and walked over to the nearby chair, taking his seat. He gestured to Stud, which was apparently a sign to begin.

I felt Studs fingers slip into me again, making me gasp from how suddenly they appeared. Checking to make sure I was still loose enough, he scissored out his fingers, pressing against my walls. His fingers soon slipped out again once he’d finished making sure, and he grabbed the first of what would be many different objects intended for my ass today. The first was a simple, smooth one that was smaller than any actual dick I’d seen since arriving at The Brick, and much smaller than Smirks – the only one that had ever been inside me. He coated it in lube and slipped it inside me with ease. Proving the expression about size and how you use it, Stud quickly got me letting out little whimpers of pleasure as he pressed into the reaches of my ass that his fingers and the plug couldn’t get to.

Agreeing with my thoughts on the size, Stud didn’t use it long. It soon came out of me and was replaced by a slightly larger one. This one was designed with a ‘realistic texture’ complete with head, veins and even the impression of a ballsack at the bottom. It might have made me laugh if it weren’t too busy making me moan. It was still smaller than Smirk but big enough to make a real impression on me, as I tightened my grip on the handles of the sling. I looked over to the client who was clearly enjoying the show, groping at his cock through his suit trousers, pumping it gently. I licked my lips, wondering if I’d feel it inside me as I felt the realistic fake leave me.

The next wasn’t realistic, but covered in ridges and ripples. Feeling it move into me was almost like being tickled, letting my ass widen and close around it as the bumps slid in and out. At its widest, it was definitely thicker than any actual cock, and it hurt slightly, though the generous amount of lube that Stud put on it soon took care of that. I couldn’t help but moan louder now as the odd sensation sent shivers through me. I wanted to get myself out of my jock but wasn’t sure if I was allowed. The ribbed one soon left my ass, and was replaced by another that was almost as thick as the thickest ribs of the last. This one was the strangest and by far the most enjoyable of the ones I’d felt so far. I let out the loudest moan I’d made yet as I felt it moving inside me. It felt like it was covered in hundreds of tiny bumps and dips.

I heard the sound of a zip, and looked to see the watcher taking himself out of his trousers. He was as huge as he looked; bigger than the one inside me, bigger than Smirk and almost as big as the Warden. I gasped and moaned as the bumps took my full attention again. It reached deeper than any previous one, making me ache slightly from its length. My fears were confirmed when I finally tried to touch my jocks bulge, only to have my hand batted away by Stud’s other, whimpering as I took hold of the handle once more. Clearly loving my frustration, he moved the bumps harder and faster, turning my whimpers to more moans. I saw him look to the client, who through the haze and panting of his arousal, gave Stud a nod, who then pulled the latest addition out of my ass.

“Last one.” He told me as he took another off the table, holding it so low that I couldn’t see what it was while he applied more lube to it. The first I felt of it was it entering my hole, the tip already nearly as thick as the last two at their widest. I gasped and winced as it slipped further in, widening my ass. It had the most bizarre texture yet. The end was pointed, and grew wider for an inch or two, then suddenly shrank down, then started to grow wider again. The top felt mostly as smooth as the first, ‘no thrills’ one that had been used on me, but the bottom had a very definitive texture to it that felt neither like the bumps nor the ridges of the previous two. I finally managed to summon the strength to pull my head up and look down, seeing that it was the bizarre, tentacle shaped one I’d seen earlier. I realised that the strange texture would be circular shapes, designed to look like the suckers of an actual tentacle.

I heard the client moaning as he continued pumping himself at the sight, and even Stud had a lustful look on his face. The tentacle was stretching my ass further than I’d ever felt before, and probing deeper than I honestly thought could happen. My body ached with pain and pleasure as he slowly moved it in and out of me. I moaned and whimpered and half-formed words before remembering not to speak, desperately wanting to beg for my release, but Stud would give me none so I had no choice but to close my eyes and hope for mercy. Finally, I heard the watcher say Studs name, and though I didn’t see whatever gesture he’d given, Stud clearly knew what to do now. I felt the tentacle remove itself from my ass, and waited for the next thing, but nothing came.

I opened my eyes to see Stud still standing at my ass. His hand was on the bulge of his lycra shorts, rubbing gently. When he saw my eyes open, he grinned, and took hold of the zip on his shorts. He pulled it down slowly, so slowly that each click of the teeth unzipping was separately noticeable at first. Finally, his cock sprung out once the shorts were loose enough to allow it. The size was impressive, but that’s not what made me gasp about it. The amount of metal in it was. In the head, there was an incomplete loop, with a ball on each end of the break in it, and going down the underside of his cock was a ladder of studs which I assumed must have been connected to a bar that went through the cock itself. I gasped at it, which must have amused Stud, as he let out a small laugh.

Wasting no time, he lined up the head of his cock against my hole and, taking hold of my hips, instantly began to press into me, becoming the second person to fuck me. He wasn’t subtle, and began pushing into me quite happily, letting each bump of his ladder pop through my ring one by one, each making me flinch slightly. I thought they might have hurt, but they didn’t – quite the opposite, each new pair of bumps just added more and more to my pleasure. I gasped and threw my head back down onto the sling as his base pressed up against me. He began thrusting in and out, slowly enough to make spikes of enjoyment ripple through my entire body, but slow enough, I could tell, to ensure that it wouldn’t be enough to make me cum.

I could hear the client enjoying himself loudly as he watched the scene, obviously reaching his own end soon. Stud began fucking me slightly faster, then faster still. I moaned as I felt myself building, thinking he was finally going to let me release. The disappointment almost crushed me when I felt him suddenly pull out. He took himself in hand and started beating it aggressively, gasping and bucking his hips, tilting his head backwards. I looked to the client who had just let out an almighty moan, seeing that he’d began shooting his stringy seed over the floor in front of him. Stud came shortly afterwards, shooting his cum onto me, coating my cock and balls and parts of my stomach with the strings. I threw my head back once more, desperately craving release and fearing that I might not get it now.

They simply left me hanging there as the client stood up, wiping himself off with a handkerchief and putting his spent cock back into his trousers. Stud returned his own back into his shorts. Once the watcher had composed himself, he walked over to my side, cupping my face with one hand, smiling sweetly. “Yes…” He said in a deep voice as he leaned in close. “I definitely like you…” He kissed me on the forehead and then moved away. Stud walked with him to the door, and kissed him on the cheek once more, holding the door open and letting the client walk out before closing it again behind him. He turned his attention back to me, walking towards me with a grin on his face.

He stood at my ass once more, taking hold of my hips. “Poor thing…” He laughed, as one hand trailed across my stomach, dragging a finger through a puddle of his cum and slowly moving down to my jock. “I bet this aches, doesn’t it…” He pulled down my underwear, taking hold of my cock, and any hardness I’d lost in the few minutes I’d been neglected instantly flooded back into it as he very slowly began to pump. The fingers of his other hand began to probe once more at my now much looser feeling hole, and I let out a desperate whimper, knowing that this teasing wouldn’t be enough. “Aww…” He spoke with a patronising tone. “Li’l Yelper wants his happy ending?” I nodded my head desperately, not caring about the way he spoke, but it clearly wasn’t enough.

“Puh…” I started to say, so quietly I wondered if he could even hear. “Puh… P-p-please…” He could hear, and it was apparently all he wanted to hear, as the fingers teasing my hole suddenly sunk into me, cutting off my begging and making me gasp. They found my prostate once more and he began pumping my cock much harder. It took less than half a minute for him to send me flying over the edge as I let out a howl, emptying my balls and covering myself with shots of my cum. He pumped out each and every shot, making sure it all went over me.

He left me hanging, panting desperately for breath as he turned his hands left me and he turned his attention elsewhere. I heard him moving around, too exhausted to look at what he was doing, but I guessed that he was packing away his bag once more. After a few minutes, he finally spoke. “Do you plan on sleeping there or something, Yelp?” His tone was friendly and teasing once more, as if we were walking down the street together. When I opened my eyes, he was smiling at me with his bag over his shoulder, ready to go. He helped me out of the sling, and our cum began to slide down me as I pulled my jock back up, too exhausted to be bothered by its presence. We headed back to the personal cells where I’d be able to wash it off in the sink. As we went, Stud spoke once more. “I think you just got a regular, Yelp.” He patted my ass gently as he said it.