Orgasm Roulette

By Poppet Subslut

Terri lives with his Mistress and their two friends. He has been kept in long-term chastity and is used by all members of the household as their submissive sexual toy and plaything. Each month Terri has a chance to be released from chastity and achieve an orgasm. However, before doing so he is set a series of tasks and challenges that he must complete that day to earn the right to have a possibility of release.

Today is the day when Terri has the chance to earn an orgasm, but first he has to endure whatever torments and humiliations the others have planned for him. It is going to be quite a day!

• Language: English
• Publisher: Lulu.com
• Release date: Nov 12, 2017
• ISBN: 9780244947064

Book preview

Orgasm Roulette

Orgasm Roulette

by

poppetsubslut

Copyright © 2017 by poppetsubslut

All rights reserved. This book or any portion thereof may not be reproduced or used in any manner whatsoever without the express written permission of the publisher except for the use of brief quotations in a book review or scholarly journal.

First Printing: 2017 2nd edition

ISBN 978-0-244-94706-4

Chapter 1

The pain woke Terri up. It always surprised him how something so small could, on occasion, cause him such acute discomfort. One minute he was fast asleep, dreaming who knows what, the next he was very, very much awake. Years of experience kicked in and he instinctively rolled over onto his back, focussing his attention on trying to block out the sudden intense, throbbing sensation in his groin. He knew that if he lay there on his back, lay still and blanked his thoughts, then in a few minutes the discomfort would start to fade. The throbbing would ease and so too would the sensation of someone trying to slowly, deliberately and with unrelenting force wrench his testicles from his body, he just needed to try to relax. He lay still and focussed on his breathing, willing himself to relax.

Ten uncomfortable minutes later he pulled the bed sheets to one side in frustration and slipped as quietly as he could out of the bedroom to avoid waking Her Highness who lay sleeping soundly next to him, and waddled awkwardly to the bathroom. His nightie bulged unnaturally between his hips, pushed out by the swollen flesh of his penis as it strained against the metal leash of his chastity cage. He needed to pee, really needed to pee. His swollen bladder increased the pressure on his loins and with it the discomfort he was still experiencing. Until he pissed he knew there was little prospect of his caged erection fading and with it, the pain and his ability to fall back to sleep.

Night time erections were something all men experienced at about this time of the small hours, even him. For most men they were normally just a fact of life, something they woke up with every morning. The biggest annoyance being that they made peeing whilst standing up a somewhat less accurate and more hazardous experience than normal. However, in Terri’s case it had been years, decades even since he had last peed standing up. This was because since soon after he had met Her Terri’s penis had been locked in chastity. At first it had been a game, something played with off and on, but then it had become more serious and now it was, to all intents and purposes, permanent. Wherever he was, whatever time of day or night, Terri’s penis was encased within the confines of a, usually metal, cage. Wearing such a device made pissing standing up a virtual impossibility so Terri was long accustomed to squatting down on the toilet seat to pee. It also meant that his penis never had the space to spring to attention in the morning. Instead it was locked up inside a small one and a half inch metal cage. Erections became all but impossible in the normal sense of the word. Instead Terri cock bulged out of the bars of its cage in a fruitless attempt to break free. It was the same every morning, most times he slept right through undisturbed by the drama in his groin, but occasionally it woke him, and very occasionally it did so painfully. This was one of those occasions.

He flopped down on the toilet seat in the darkness. Judging from the lack of any sign of light outside he knew it was still the middle of the night, many more hours before the day was due to begin, plenty of time left in which to fall back to sleep when eventually the pain of his confined erection subsided. Angling his hips forward and shuffling to the rear of the seat he found a position in which, despite his bulging and straining penis, he was confident that he could push the chastity device down far enough towards the toilet bowl that his piss would stay within the toilet and not spray out across the bathroom floor. That had happened to him once a few years ago, he'd somehow sprayed piss all over his legs, all across the floor and up the door of the bathroom cabinet. He didn't want to do that again!

He took a deep breath and then squeezed his bladder muscles, forcing out a thin jet of urine. It splashed reassuringly into the water in the toilet bowl. He squeezed again and forced out a longer stream. Slowly but surely his caged cock began to subside as the pressure of his bladder subsided. After one final squeeze he gave the chastity device a shake, grabbed some toilet paper and dried himself up and then shuffled out of the bathroom and back along the corridor to the bedroom. Once back in the room he silently slipped back under the covers and lay there motionless in the darkness waiting for his waning erection to fully subside.

The discomfort faded rapidly. He could feel his testicles relax and drop and the pressure around the base of his penis subside. A couple more minutes and he would be fully flaccid again and then he could drop back to sleep. It was unusual for him to have been woken up like this, unusual to experience this level of discomfort. Most days he slept right through or, if he was disturbed, would just roll over onto his back and a minute later all would be fine again. That hadn’t always been the case. When he had first started to wear the chastity device on an extended basis he had been woken regular as clockwork, 2am, 4am, 6am as his cock strained and bulged fruitlessly against the metal confines of his chastity cage. He could just about still remember the time when he hadn’t been locked up, it was…..he mentally calculated in his head….crikey it was. Wow! Was it really that long? Yes, it must be, he was certain. It was just after they came back from a trip to Tallinn, their first weekend away together. That had been 16 years ago. 16 years! It was also the last time they had had sex. Well, that is to say the last time they had had what most people would describe as sex. They still had and enjoyed  sex only that sex for them was different in one fundamental regard. His cock no longer, under any circumstances, penetrated Her.

Back then the device he had first worn was plastic. He still had it. She had chosen it as it would enable him to slip through airport security without it triggering any alarms. However, it was impossible to conceal under tight trousers and after a few weeks of wear it became quite aromatic, no matter how hard he tried to keep it clean. After a few months Her Highness had consented to him getting a metal device and they had chosen the smallest one on the market. It was a very short, stubby metal cage, just a criss-cross of bars really that trapped his penis inside. She could still touch and poke his flesh and it was just the shaft and head that were locked away like that, his testes still hung free, and vulnerable. The device was about half the length of his thumb, just a little fatter. It proved almost invisible to detect under even tight denim. It also highlighted and reinforced the fact that, in truth his cock was almost pathetically small.  Its diminutive size maybe explained a lot about him; his love of giving oral pleasure but complete disinterest in receiving it. His willingness, no eagerness even to have it kept locked away. It was small and pretty useless anyway why not just lock it up as it wasn’t much use for anything else?

At first, after they had returned from that trip to Tallinn, he had been kept locked-up by Her Highness for relatively short periods of time only, normally a few weeks at a time. However, all that had changed in the last decade. For nine years now his chastity had become permanent. She even insisted he keep his device on when they were travelling. At security She would normally join a different queue leaving him to face the humiliation alone of explaining to the security official why it was that he had just triggered the metal detector and that no it was not possible for him to remove the device as he did not have the key, which was the truth. Sometimes they waved him through with a smirk and a laugh behind his back. Other times he was escorted to an examination room where he had to show them that he had indeed been telling the truth, pulling down his pink panties (and yes, they were always pink that was the only colour he was permitted, sometimes lacy, sometimes ruffled, sometimes plain but always pink) to reveal his pathetic little locked up cock. In fact, so often had this occurred that he had come to know exactly where he would be able to find Her Highness after his lonely ordeal with security was over. He would always find Her sat in the nearest café sipping tea and reading when he returned red-faced from his latest humiliating interrogation. She would always remind him that this was just one of the consequences in life of his choosing to submit to Her domination of him. Him being kept in permanent chastity was just one of the many ways in which She controlled his life completely.

Except that his cock wasn’t quite permanently locked away. She had introduced a game. On the first day of each month She would permit him the possibility of being unlocked and of having an orgasm. Whether this actually happened or not was entirely down to his behaviour that day and to luck, or chance. After keeping him in a heightened state of sexual arousal all day She would decide whether or not he had performed and behaved acquitted himself well enough to be allowed to play orgasm roulette. Orgasm roulette consisted of Her rolling a dice in the evening. If, She rolled two sixes he would be unlocked and the chastity device removed and he would be made to orgasm.  It had started out with Her only needing to roll one six, however, about six years ago She had rolled sixes three months in a row. They had been fluke throws but they were enough for Her Highness to order a tightening of the rule. From that point onwards She had instructed that two dice be used and that She had to roll a six with each dice in order for him to be released and ordered to cum. Since then a six had only ever been rolled twice on one occasion and that was over four years ago. He had not experienced an orgasm since then. He had been milked, had his prostate gland in his anus massaged so that he released an involuntary stream of semen but as an experience this was completely different from an orgasm. It did not provide the rush and explosion of pleasure that an orgasm did, rather it was closer in sensation to a very satisfying pee as a long stream of ejaculate drained steadily from him, usually into a glass which he was normally then made to drink.

But, back to the monthly dice game. The rules were simple. If he pleased Her enough for Her to judge that he was permitted to play (and in truth there had rarely been a month when She had decided he did not deserve to play) orgasm roulette then She would take a dice and decide his fate. In the now highly unlikely, but still statistically possible, eventuality that two consecutive sixes were rolled he then had to pick a card out of a hat. On each of the cards would be a written set of instructions detailing quite how he was going to be permitted to orgasm. There were fifty cards in the hat and each card contained a different set of instructions. He had no idea what was written on the cards except that each was purposefully designed to ensure maximum humiliation or embarrassment to him. She had tried to convince him that one of the cards wasn’t designed to humiliate, that it simply said ‘masturbate in front of me until you cum’ but he had never picked this card. Of the 11 cards he had picked over the nine years they’d played the game and successfully rolled a six (now two sixes) each had ensured his winner's orgasm ‘reward’ had been the most embarrassing or humiliating possible. To date he’d been;

masturbated to orgasm by Her Highness on a busy tube train

masturbated to orgasm by Her Highness in a cinema

masturbated himself to orgasm standing naked in front of their lounge window – and then had to lick