The Games We Play Ch. 18

The Games We Play, Ch. 18

This story series involves infidelity, cuckolding, domination, corporal punishment, and chastity. Fun themes for some, distasteful for others. If you fall into the second category and still read the story, remember you were warned.

A VERY SHORT RECAP: The early chapters set up the story of how Julie was sending her husband off on his business trip in chastity while she became her lover's full-time girlfriend. The next chapters documented the crazy fun that Julie and her lover were having while only offering Scott, Julie's husband, just a few details that his wife's lover shared because his wife had cut off all communication. Recently, Scott learned that his wife and his boss had hooked up, seriously hooked up, and chapters 8-9-10 were the fun times Jacob and Julie have together and the fun they had telling Scott all about it. Chapters 11-12-13 saw Scott's return from Europe and the immediate dominance asserted by Jacob and Julie. Chapter 14, 15, and 16 chronicled a day of deep humiliation for Scott which included his trip to Jacob's barbershop, punishment for disobeying and disrespecting his wife, and being the emcee of the company banquet where his wife attended as Jacob's date. Chapter 17 chronicled the intense night of sex and commitment that Julie and Jacob had and this chapter covers the same time frame and finds Scott at the mercy of Jacob's executive assistant, Rachel, a woman who was playing her own game.

This chapter is told from a third-party perspective.

If you like this latest addition to the series, please let me know with a comment, mark it as a favorite, and follow me for alerts to the next chapters. I also love getting direct messages from the Literotica community. I always respond to non-anonymous messages.

Happy reading, and whatever else you might be doing while reading! ;)

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"I want you to strip and I want you to do it slowly." While Jacob had circled Julie while she stripped, Rachel, in her full latex outfit, did the same to Scott. She took her time teasing him and getting him ready for a night he would not soon forget. When he removed his boxers, she saw that his ass was already full of welts and was still glowing red from the punishment he took from his wife.

"It looks like your wife really went to town on you, so I guess I'll just have to enjoy making your other body parts hurt just as much."

As she said that, she whirled around and struck the back of his thighs with the riding crop she was holding. Scott yelped as the sting radiated across his skin, and the sharp pain reminded him that he was now Rachel's toy to be played with. He had a night off from being his wife's and boss's pet and here he was getting abused from his boss's secretary, although he knew if he called her that, he would get seriously hurt. She was Jacob's executive assistant, not his secretary and nobody called her a secretary without catching shit from both Jacob and Rachel. But Scott laughed to himself, he was already taking shit from both, so if he wanted to say secretary in his mind, why not?

At the same time, it was hard not to be in awe of how hot Rachel looked. She had a beautiful young body, tight and trim with perfectly shaped C-cup breasts and an ass the was a work of art. Plus she was wearing a skintight latex suit that showed off her hotness. So, it was hard for Scott not to be distracted from the pain and humiliation he was receiving from this secretary.

Rachel knew Scott was lusting after her. "Stand with your legs spread apart."

Scott obeyed.

"Oh my, look at you in your cage. Your little dick is so tiny. No wonder your wife needs a real man."

She took her riding crop and slapped it against his balls. Scott whimpered. Rachel didn't really cause significant pain, but the promise of such pain had Scott on high alert. Rachel enjoyed playing with Scott and she ran her crop around his exposed balls.

"Tell me Scotty-boy, do you really think your wife will ever come back to you."

She walked behind Scott and put her crop between his legs. He tensed as she ran it up and down the inside of his thighs. He was so tense that he didn't answer Rachel.

She skipped the thigh shot and smacked the underside of his balls. Scott shrieked. It wasn't just the pain; it was the surprise and his vulnerability.

"Answer me cuckold. Do you think your wife will ever be yours again?"

"Probably not Mistress."

"Probably! Ha, you are dreaming. While I fuck with you, I guarantee Jacob is fucking your wife and making her pledge her loyalty. And do you think she is saying, oh no Jacob, I still want to be with my little dicked husband? Oh my god, she is saying YES Jacob I am completely yours. Always yours. You know she has already said it. Jacob doesn't play fair; he gave you to me and he took your wife and she is cumming hard on his cock and proclaiming her felty to your boss. Admit it Scott, you are done. You are out. You are mine to fuck with and she is Jacob's to fuck. Say you understand, say it now!"

She took her crop and hit him hard on his inner thigh. She knew it hurt. Scott squealed. Then he answered with desperation. His words came out breathless and frantic. Rachel loved it!

"My wife belongs to Jacob. I have lost her. She is his. I can't deny it. I am pathetic and she is perfect, but she is his."

Scott started to cry. He realized what Rachel said was true and so was what he had just said. The games were over, the reality was that he had lost completely.

Rachel smiled to herself. Jacob had promised her that if she broke Scott and left him as nothing, he would give Rachel a night she would never forget. She wanted that. She was sure if Jacob experienced her that he would never go back to Julie. Rachel enjoyed toying and torturing men, but her real motivation was breaking Scott to gain access to Jacob who was the man she truly wanted.

"Oh, poor Scott, he locked his dick up, played house boy, and let his boss fuck his wife and he somehow expected that he would still be able to be considered a man and get her back. But you are nothing, and I am going to break you and take your remaining manhood and flush it right down the toilet. At the end of this week, when Jacob returns from his condo and moves in with your wife, you will be irrelevant as Julie will belong to Jacob completely and you will be their servant and fool. They will allow you to serve and you will say nothing because you will be nothing without them even though you will be nothing to them. This is the week that Scott gets broken, and I am going to have great fun doing it!"

As she finished saying this, she started to hit Scott all over with her riding crop. She spun around him and as he tried to prevent getting hit again, she laughed and just kept going.

She finally stopped and then practically screamed at Scott. "On your knees bitch! Now!"

Scott got down on his knees. Rachel's assault had him off kilter. He felt the sting of each blow but felt the sting of his patheticness even more. He was pathetic in the moment, naked and vulnerable, and pathetic overall, no longer a man and certainly not his wife's man.

Rachel walked over to where a low platform sat on the floor. It was maybe the size of a small door and had padding on the top.

"Crawl over here."

Scott obeyed.

"Get on this platform and get on all fours like the dog you are."

Scott obeyed.

And as soon as he arrived, Rachel started to put a collar on him. It was thick leather with rings on it. She secured a chain to one of the rings and for the time being let the chain fall.

She then went over to a table nearby and got cuffs and straps and methodically secured Scott onto the platform. Two cuffs went around his wrist and secured his hands down on the platform. On his legs Rachel expertly used the other four cuff and strap combos to pin Scott on his knees. One set secured his upper calves right below his knees and the final set went around his ankles and held his feet and lower legs down.

Scott did not protest as Rachel secured him to her platform. He was too beaten down by his wife and her lover, also known as his boss, and too enamored with Rachel to protest. Rachel enjoyed his submission and pulled each strap tight. She laughed to herself as he was so passive yet would be so actively abused soon enough.

She let him feel his helplessness for a while and then put her boot up to his face.

"Lick my boot, you worthless turd!"

Scott complied. He was beaten, he was broken. He was helpless and hopeless, matching up with both definitions of that term. He had no hope and he was pathetic and thus Rachel was almost disappointed with how easily she was binding and humiliating him.

Rachel decided to turn up the heat. He was so easily bound that it was time to test him. She went and got a ball gag and held it in front of Scott.

"Time to take away your voice, the way your boss has taken away your authority and made you his personal servant. Open up, cucky-boy!"

Scott once again accepted Rachel's bondage and soon he was gagged tightly. He felt like he was truly Rachel's toy to play with, and Rachel decided to prove him right. She got a butt plug from her table of toys and came over and held it in front of the completely helpless Scott.

"Time to truly make you a bitch. I won't lie, this is going to hurt, but feel free to say no and get up and walk out of here."

She waited a moment as Scott tried to say no and she laughed as he fought against his constraints.

"I guess you want to feel the penetration and be my bitch. OK, then I will oblige!"

She laughed and went around behind Scott and played with him. She teased him, running the tip of the butt plug across his butt hole. She always enjoyed the psychological torture as much as the physical. She loved creating tension and fear in her captives. She continued to up the pressure with Scott by reaching under and squeezing his balls. She knew it hurt but she also knew touching him was something he desired.

She leaned in and said, "You like that, don't you, so be a good bitch and take my plug and maybe I will give those fully exposed and available balls of yours some more attention."

Rachel then got some lube and pored it down his ass crack. She put a rubber glove on and soon Scott froze as her finger started to circle his butt hole. A few moments later, Scott experienced his ass being penetrated as Rachel's finger slid into him. Scott gasped, which was muffled by his gag, but clearly understood anyways.

Soon she was playing with him, inserting and removing fingers and wiggling her fingers inside of him. Scott began to think that it wasn't half bad. It didn't really hurt and his desire for Rachel was so high that he started to crave the penetration and pushed back against it.

"That's it, bitch. Accept it and embrace it, be my obedient bitch. You love it, don't you?" Rachel taunted her captive.

It was time and Rachel removed her fingers and positioned the plug at the entrance to its new home. She started to push it in just a fraction of the way and then she would pull it back out. Scott tensed; it was the wrong response but the one all her previous ass virgins had. Relax and it goes in easier and with less pain, tense up and it hurts like hell. But when an ass plug virgin is involved, there is always tension and always pain, but it still gave Rachel a chance to tease and taunt Scott.

"Just relax and take the plug. You know you want it; you want it for me. Serve me Scott, be my bitch and make me happy!"

As she said this, she started to push the plug in. Scott squealed through his ball gag as the pain hit. Rachel didn't care. She just kept pushing it in, then pulling it out a bit, then pushing it in further. Scott tried to squirm and escape the searing pain. Rachel laughed and showed no mercy.

With one final push Scott became an ass slut. The plug was fully inserted. He was panting and practically crying from the pain. But then he started to calm down as the feeling became more arousing versus painful. The plug created a sensation he had never felt. It made his dick ache and actually release some pre-cum.

Rachel continued to work her magic, and she started to pull the plug out and push it back in. It didn't take long before Scott's pain started to ebb and his arousal flowed. He started to moan and push back.

"Aren't you just the perfect ass slave. You love this and you can't deny it. Scott, my boy, you are now officially my ass slut and you know you love it!"

Scott couldn't actually argue with Rachel and he couldn't believe how good it felt. He moaned and got out an enthusiastic but muffled yes mistress. Rachel loved it. She always got great satisfaction when she converted another ass devotee and she was sure Scott would welcome more ass play based on the fact it only took about 3-4 minutes for him to love the experience.

She fucked his ass a few more times and then pushed the plug all the way in and slapped Scott's ass. Scott felt full and he loved the feeling.

Rachel had one more surprise for Scott. She went over to her table and got one of her favorite toys. It was a stainless-steel ball stretcher an inch and a half long. It was going to be the first time she had ever used it on a guy already wearing a chastity cage. She was looking forward to the challenge.

She walked up to Scott and raised the platform he was on so that he was now face to face with her. She held the ball stretcher in front of Scott.

"You know what this is cucky-boy?" She didn't expect Scott to answer. She just continued, "It is my favorite toy. It is going to stretch your poor little testicles and make them so tender and ready for abuse."

Rachel went behind Scott and started to grab his balls and pull on them. They were already pinched between the base ring and his cage, but Rachel started to pull and squeeze and stretch and Scott started to whimper. He had an incredibly hot young woman massaging his balls. He knew why, but he just didn't care. Scott had not had any sexual contact for a long time and he no longer cared. It felt glorious to have his balls touched. He hadn't had a good cum since before he left for Europe and he was beyond desperate.

Rachel could tell he was enjoying her touch so she changed that and she took her finger and flicked it hard against his right testicle. Scott yelped and Rachel laughed.

"There is no pleasure for you. Jacob gets pleasure courtesy of your slut wife, she cums hard on his cock, and I always love having an obedient little boy to fuck with, but your role is to take it like my gagged ass bitch!"

Scott was in a vortex of frustration, desire, pain, excitement, humiliation, denial, and arousal. The crazy games that had been played at his expense by his wife and his boss seemed tame and even distant. Rachel had him in a state that was shifting so fast he was putty in her hands and that is the way she wanted him to be.

She went back to pulling and stretching and there was pain and arousal and fear. He was very leery of allowing himself to enjoy the touch of this beautiful woman lest she flick him again. Finally, she had him stretched and she opened the device into two half's and placed it around his skin stretching the skin and pushing his testicles to the very end of his ball sack. It wasn't a sharp pain as she closed and secured the device back into a ring, but just moments later he could feel his balls start to ache and it left him incredibly vulnerable.

Rachel rubbed his balls and then squeezed them hard.

"Just wait, the weight will start to take its toll, and if you have ever had blue balls before, this will be just like that. You know of all the toys and whips and flogs I have, that little device is the most frequent cause of one of you little beta boys breaking down and begging me to stop."

Rachel squeezed his balls one more time then tugged down on the device pressuring his testicles. It hurt and Scott could not help but moan. Then Rachel slapped his ass and said, "Enjoy!" And she briskly walked out of the room and turned off the lights. She loved letting her subjects absorb her assaults as they spent an unknown time alone in the dark.

Scott was overwhelmed. He hurt, but he was also aroused. He wanted Rachel to come back, but also feared the other things she might do to him. He had both discomfort and sexual stimulation happening simultaneously, and he was having a hard time separating the two. He wanted Rachel badly, as any man would, but he also wanted his wife, but knew she was with Jacob and certainly wasn't missing him. Scott was beaten but was also craving more. In the end, Scott was exactly where Rachel intended him to be.

With Scott left in the dark with his thoughts, Rachel texted their boss.

Alone in the dark for a few hours. I am not holding back. He is confused and overwhelmed. He will be broken for you soon.

She smiled when she saw the response.

And his wife is entirely mine. Poor Scotty. Keep up the good work and we can start planning our evening together soon.

Rachel loved his message and sent a reply.

It will be an amazing night!

She was thrilled that Jacob emphasized her message. She was making great progress towards Jacob being hers!

Rachel left Scott secured like a dog, plugged, stretched, and gagged alone in the dark for 2 full hours. She took some of the time and masturbated while thinking about Jacob. She was very excited by the thought of being with him.

It was stupid, she was 30 years younger and should be lining up her husband, instead she longed for Jacob. She saw this whole Julie thing as a distraction. Jacob would tire of her and recognize Rachel as his best alternative. She would be his queen and peons like Scott would tremble at her feet. She exploded into an orgasm and then laid in her bed frustrated. She wanted Jacob so badly and was determined to win him. She would take him from Julie, from his wife, and she would become Rachel Stark!

She leapt out of bed and headed to where Scott was bound and gagged and she threw open the door and flicked on the lights.

She startled Scott and he ducked his head as the lights hurt his eyes. She went over to him and grabbed his head with both hands and pulled his head up so she was looking right at him.

Scott was both terrified and immediately aroused. Rachel was a Goddess in her latex suit and while she had been fantasizing about Jacob, he had been fantasizing about her. He had admitted to her and to himself that he had lost Julie entirely and the one silver lining to that was that he was free to think about another woman.

Rachel was a woman many men thought about. And he wasn't on a date with her, but he was with her even if that was as her subject in her dungeon. As he felt the discomfort of his position, he also felt a strong desire for Rachel and a strong desire to be submissive, especially to her. He found himself pushing hard against his cage thinking about submission, about being obedient, and especially about being Rachel's pet.

So, as his head was jerked up and an intense Rachel stared at him, Scott's primary reaction was lust. He wanted her and wanted to serve her and since Julie was no longer available to him in any way, he could have this strong reaction to Rachel and it was OK!

"You are the key, and you are going to help me get Jacob, the ONLY man I want, and then you can get your wife back. But that starts right now with you understanding that I will burn you to the ground if you don't do everything I tell you to do. If you don't help me then I will ruin you personally, professionally, and socially. Do you understand you piece of shit!"

Rachel surprised herself with how angry she was and almost didn't recognize her own voice as it commanded Scott. But this thought didn't prevent her from digging her fingers into Scott's head as she held him. Her eyes blazed and Scott could have no doubt that Rachel was serious.