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Trials of a Cuckold  

awaygames69 50M
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5/19/2018 12:49 pm
Trials of a Cuckold

Susan had advertised himself on the kink sites as a bisexual sissy transvestite for a number of years. He was looking for a female who would indulge a long term cuckold/wittol relationship. Finally a woman named Yvette answered his call. She had been through the marriage mill with now grown up . She had played the dutiful wife all these years and been faithful to her now ex-husband. Many times through these years she had longed for sexual excitement outside the marriage but her conscience and fear of consequences kept her in check. Now the were out of the way things were different. She found the courage to demand a divorce and Jim offered little resistance. Yvette certainly didn’t want to find another man and start another vanilla relationship, she wanted something different. She read a magazine article about men who liked their wives to have sex with other men while they watched or assisted and though somewhat freaky, this really got Yvette’s bells ringing. It led her to research extensively into this fetish interest and everything about it pleased her. The thought of having a faithful, devoted and loving partner while having the freedom to enjoy sexual pursuits with others could lead to a wonderfully satisfying lifestyle.

Yvette arranged to meet Susan over coffee and discuss each other’s interests and goals. She was fully aware the relationship should not only be based on mutual sexual interest but also shared general interests, ideals, humour and pure attraction. Yvette found Susan to be a slim, fit, moderately good looking guy, articulate and personable as well as a convincing tranny which was a good start. She got him to discuss what kind of things he was looking for in a cuckold relationship. What Yvette then realised was how much assertiveness on her behalf was going to be required for a relationship like this to work. Yvette had never thought of herself as dominant over anyone or had ever tried to be but it was going to be necessary to fulfil the desires of both parties. What was delightful to hear from Susan was that he loved chastity and all the physical and psychological connotations that accompanied it. The idea of having a man’s penis locked up in a device and completely under her control as a key holder was extremely appealing. Susan admitted he had never as yet been in a sexual situation where he was restrained and a partner was pleasing herself with another in front of him so he could not guarantee how he would feel about it. Yvette decided she would immediately starting putting Susan to the test. She said,”Susan, I’m doing a lot of dating at the moment now I’m a free woman, so I’d like to see how keen you really are to embrace this lifestyle. To warn you it’s going to be very hard for you to keep up with me. I’m dating someone this evening and I want to test your obedience and resolve so if you can be available from 6pm I will text you your instructions later.”
A rush of excitement filled Susan over what might happen later this evening. At about 6pm He received the following text from Yvette, “Hi Susan, I’m meeting a guy for dinner at Carlito’s in town. Be there for 7pm sharp and wait on the opposite side of the road to Carlito’s. As it’s very cold outside be sure to wrap up warm.” Susan was somewhat puzzled at the request and how things were going to transpire this evening. Would he have any interaction during the date or would he meet her afterwards?

Susan made sure she was there just before 7pm opposite Carlito’s. Soon after she saw Yvette with a man across the street walking towards Carlito’s. He watched them go in and soon they were given a table at the front window where they sat down and made themselves comfortable. He could then see Yvette on her phone texting and moments later Susan’s phone pinged to signal an incoming message. Susan read Yvette’s message, “I can see you Susan, if you can move further down the road but still remain in my view I will be in touch soon.” Susan moved down the road as instructed and waiting trying to look as casual and inconspicuous as possible. It was perishing cold and he was glad he wore thermals, hat, scarf and gloves. Only his feet were unable to withstand getting cold. About an hour later another text pinged on Susan’s phone, a message from Yvette. It read, “I can see from this distance your feet are getting cold from the way you are stamping them. Assuming you are wearing zip front trousers I want you to discreetly take out your genitals and let them hang outside of your trousers. Don’t worry, your long over coat will keep you from any embarrassment but I want your cock and balls to be cold like your feet.” Susan obeyed and with a little awkward movement to get them past pants and thermal leggings they were out. Yvette was right, after the cold wind had drafted up under his coat a few times his balls and foreskin did feel the bite of cold. To pass the time Susan wondered and contemplated the reward of his suffering.

About an hour later another message pinged and Susan could distantly make out Yvette and her companion were getting up to leave. The next message read, “We are just going down the road to a bar for a couple of drinks. Follow us at a distance and then wait outside.” On exiting Carlito’s Susan watched Yvette lean in to the man as she walked along. They soon arrived at Misty’s club bar and entered. Susan waited again and drifted into fantasy about how the evening might turn out. Would Yvette finally invite him to join them or perhaps even better have some kind of threesome fun.

Time passed slowly but eventually the couple emerged from bar entrance. They hugged and cheek kissed before the man turned and walked off down the street. Yvette stood alone at the edge of the pavement and waited. About a minute later she raised her hand. Susan momentarily thought she was signalling him to come over but then a taxi suddenly pulled up and Yvette got in. It drove off and Susan felt the sting of embarrassment and humiliation sweep across the skin of his wind chilled face. A few moments later his phone pinged and he read the message, ”Thank you for this evening Susan. Now go home and get yourself warm and I’ll be in touch soon. Good night.” More prickles crossed his face to drive home the disappointment but for now he was more concerned to get out of the cold and think about it later.

Later in bed Susan did think about it. The humiliation was actually very arousing. He had always felt like a person on the outside looking in and now it was happening literally. This arrangement happened another couple of times before Yvette decided to push things further. After another lunch together, Yvette announced she wanted to nudge things along. She was now on web sites where attached women were looking for a little on the side. She had sifted out a few potential dates and found a guy who was perfectly agreeable for her ‘partner’ to have full knowledge of her activities. Yvette informed Susan that all would become clear on the date. The following evening Susan was ordered by Yvette to reserve her a room at the Winston Hotel in town and to be wearing a chastity device under his attire and to also bring the key to its lock. Once there, Susan gave her the key and they waited in the foyer for a short while before her date appeared. Yvette and Susan stood up to greet him. Yvette said, “Hello Bryn, I’m Yvette and this is my partner Susan.” Susan’s cheek reddened at being introduced with a girl’s name. Yvette kindly interjected and said Susan should go and pay for the room so they all went over to the check-in desk. Once the concierge had booked them in Susan wondered what he must be thinking of this odd menage-a-trois. When they arrived at their room door Yvette commandeded Susan to unzip his trousers and pull them and his pants down slightly. Brynn could now see Susan was wearing a pink chastity device and really didn’t know where to look. Yvette said, “This is how I like to keep my partner when I am with other men as she dangled the key on it’s little chain. Susan, pull your pants up. You are now to wait outside this room until we come out. If anyone passes by and asks why you are standing outside you are to answer ‘I’m just waiting for my wife to finish her business’, understood?.” Brynn was now smirking wryly as he and Yvette entered the room and the door clicked shut in Susan’s face. Susan could hear the two of them laughing loudly inside the room imagining it was almost certainly at his expense. It soon went quiet and Susan’s anxiety compelled him to bring his ear to the door to listen. Shortly after, Susan felt a tap on his shoulder. He turned round to see a waitress carrying a room service tray who said, “Excuse me sir, are you locked out of your room?”. Susan’s stomach churned with nausea and embarrassment at the response he had to make but worse was to come. His phone rang and it was Yvette who said, “Tell whoever that is ‘this is the business she’s finishing’ and pass the phone to her. Susan handed the phone over and the waitress listened. The sound of grunts and sighs as bodies slapped together came down the phone. The waitress handed the phone back, put her hand across her mouth and walked away down the corridor trying to stifle giggles and maintain the tray’s balance with great difficulty. The next two hours went by uneventfully thankfully for Susan. It was nothing of the sort for Yvette and Brynn when they appeared at the door with damp hair and flushed faces. Susan could smell that they had just showered together and a surge of lustful jealousy went through him as he imagined their wayward hands swilling each other’s soapy bodies. Yvette had one last nasty surprise for Susan and said, “Susan, Brynn and I are going for a drink and then making our way home. Here’s your chastity key. I want you to go into the room, take your clothes and your chastity device off and lie on the bed. You will see Brynn’s used condom on the bedside drawer. Put it in your mouth, make the cum ooze out by chewing it and masturbate yourself thinking about what we’ve just been doing. Once you’re done, have a shower and put your device back on. As the room’s all yours now you can sleepover if you like. I’ll be in touch.” Susan did exactly that since it made a nice change to stay in a hotel room but it was an uncomfortable night’s sleep as he kept getting aroused and the pain of his cock being prevented from hardening woke him up numerous times.

Yvette was pleased with Susan’s progress in the relationship and had enjoyed humiliating him as a man. Now she wanted to do it to Susan as a transvestite. They arranged to go as a couple to a swingers club, one which had a good number of single people too. It was fun getting ready for the night ahead and Yvette helped Susan with his make-up and getting dressed. Yvette felt a sense of warmth and pride as she surreptitiously observed Susan on the way in the taxi but it was going to be another ordeal for her submissive sissy. They arrived and got settled at the club by mingling and chatting with some people. Yvette liked these clubs in the way the chit chat was a feeler as to who you might partner up and have fun with later. Yvette told Susan to leave her alone for a while so she could go and chat with a couple of men she had her eye on. After a while Yvette called Susan to come over and told him to accompany her to the ‘lockable room’. Once in the room Yvette introduced Mark and Shaun to Susan and he curtseyed to them which made them smile. Yvette told Susan to lift the front of her skirt up exposing his caged appendage and said, “ As you can see guys, my partner is under my control this evening and will do everything I tell him to. His cock will take no part in the proceedings and I might allow him to watch us. Susan, for now can you turn and face the wall!”

Behind her Susan heard the rustle of clothing and increasing breaths along with the sound of male mouths sucking and slavering over female flesh. The sounds then soon switched to Yvette’s mouth where she had obviously gone down on her knees to give oral sex. The slight pause between each slurp and gag suggested she was going from one cock to the other. Susan started to harden in his cage and the familiar constrictive pain seared through his penis. To now he had not disobeyed Yvette once and wondered what harm could be done by taking just a quick peek. He turned to look and was immediately met with a sharp feminine reprimand, “I never said you could turn round, face the wall now, wimp!” A sting of shame and embarrassment struck Susan as Yvette quietly informed her lovers I would be dealt with later. The squeak of springs informed Susan that three bodies had gotten onto the bed and the gasps and brushing of skin confirmed the action was now getting serious. A crinkle of wrapper followed by a snap of rubber meant that cocks were stiff and now ready to go to work. Susan heard Yvette’s first deep sigh as the first cock penetrated and then there was a more agonised sigh as the other presumably entered her anus. Susan tried to imagine their position and surmised Yvette must be on top of one and the other kneeled doggy behind. A slowly increasing rhythm of male grunts and female gasps started to build and the room got noticeably warmer and humid from the energised and perspiring bodies. Susan longed to be able to masturbate and released or at least be allowed to watch but his otological torment continued. The sound of nipples been sucked hungrily signalled the nearing of Yvette’s climax. She shouted, “God I’m gonna cum, cum with me you dirty fuckers!”. A male and female voice subsequently resonated the room with their orgasm and Susan squirmed in a mental anguish of envy and arousal. He wondered what happened to the other man’s climax and Yvette gave the answer, “Oh Mark, if you haven’t come yet you can finish off inside Susan. Susan, can you bend over, slowly lift your skirt and keep your cheeks parted with your hands.” Mark watched and needed no second invitation. He slipped out of Yvette’s anus, went to grab a bit of lube and within seconds his freshly smeared cock was prodding at Susan’s entrance. The cooler air around Susan’s open cheeks was soon overwhelmed by the heat and pain from Mark’s searing shaft as it surged it’s way in. Susan brought his hands to rest on his knees for better balance as strong male hands gripped his hips. A familiar thud of discomfort hit Susan’s anal wall and thrusts rattled his flaccid penis in its cage. Susan never got an erection during anal sex because his male responses were completely switched off. While watching, Yvette stated that when he was ready to come Mark was welcome to whip off his condom and shoot in Susan’s mouth. That was exactly what he ended up doing so Susan had another load of sperm digesting in his stomach.

As the months went by Yvette and Susan got much closer and were now living together. Yvette’s dominion of Susan had also progressed and she now had Susan in permanent chastity which was much easier to enforce living under the same roof. Susan was kept very busy and always had a list of chores to complete after his day at work. Yvette is very health conscious and ensured a strict diet for Susan so he would always perform at his best and without the lethargy caused by alcohol, drugs, smoking or over indulgent eating. Though there was much intimacy between them Yvette always preferred to sleep alone unless she had a lover stay over. The level of authority Yvette had in the relationship was emphasised in the fact that she had a lock on her bedroom door and Susan’s room had the door removed from its hinges to ensure no privacy. Yvette regularly had lovers in her bed and it depended on the persuasion of her lover as to how much Susan was involved. The least was that Susan had to leave the house the whole time he was there and stay /sleep in the car. The most involvement was Susan being used as a mattress for Yvette to lie on while she was being fucked. This was very pleasurable for Susan when coital juices trickled down past Yvette’s anus and into Susan’s mouth.

One day Susan came home from work as usual and as he stepped through the door he was immediately greeted by the sound of female moans coming from upstairs. Yvette had never made an arrangement without letting him know before which was strange. There was a trail of man’s and woman’s clothing leading up the stairs which he followed towards the noises coming from Yvette’s room. On entering, on the bed he saw a huge black, naked muscular body embraced by a pair of slim white arms and two small feet bookending his neck. The only real movement was powerful glutes driving downwards and inwards. Susan stood and watched open mouthed for what seemed like a few minutes as they continued oblivious of his presence. Then Yvette turned her head to one side and caught sight of Susan as the stupefied voyeur and just brazenly held his gaze as she gasped at every thrust of her lover. With his face buried in Yvette’s neck the huge black beast made a final thrust and let out a huge grunt and spewed his seed deep inside her. Still staring at Susan, tears of joy rolled from Yvette’s eyes as the huge bulk sagged with spent fatigue on top of her.

Susan said, “How come you didn’t tell me about this Yvette?”

Smiling in afterglow and smoothing her hands up and down her lover’s back Yvette replied, “Darling, this is the next step of our evolving relationship. Could you get a new front door key cut as Leon here will be needing it. Don’t worry it won’t affect anything between us, he’ll just be regularly dropping by. Now run along, there’s a list of jobs written down in the kitchen. Oh, and close the door behind you.”

Susan’s arms and legs felt numb and limp but his cock was expanding fiercely inside its cage. He turned and walked out, closing the door quietly behind him to go downstairs and get on with the tasks assigned. Susan wondered whatever would be next….

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