The Games We Play Ch. 08

This story series involves infidelity, cuckolding, 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, who up to now was actually doing pretty well as the humiliated and denied cuckold, learned that his wife and his boss had hooked up, seriously hooked up, and in this chapter the cuckold learns more of the story via a very humiliating, but hot situation. You know, the kind cuckolds love.

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 wasn't sure how I was gonna handle it. I was going to go into a live connection with my husband who is currently in Europe and is currently locked tightly in a chastity cage as he has been already for four weeks. I on the other hand, was going to get fucked by my husband's boss live in front of my husband. I wasn't sure if this was going to be too much or too little. This started as a game with my husband, but this seemed out of the realm of a game. That concerned me but didn't stop me from being wet and aroused at the prospect of getting fucked by Jacob right in front of Scott. Funny part was in our world of games it was supposed to be Evan fucking me, and yet, he was off with Jacob's wife and there was only Jacob and he does not play games if they are not for keeps. I couldn't help contemplating how I got to this point.

I set my husband off to Europe on his annual six-week trip of business calls for his company locked in the chastity cage and knowing that I was going to spend six weeks with my boyfriend, Evan, living as a fun and sex filled couple.

Then a funny thing happened one night when we are out at an Italian restaurant, I ran into my husband's boss. A man I had come very close to having an affair with a few years earlier. A man that quite literally had always made me wet when I interacted with him. That night, after we left the restaurant, I gave him a hell of a blowjob in his car and then we went back to his house, and he fucked me multiple times while my boyfriend fucked his wife and then all four of us got busy in the hot tub and we had an amazing time.

The next day, his wife invited us back for more fun, and by the end of the weekend, I was officially his and was going to remain his as long as he wanted. I was his for two reasons, first, it was delicious fun to think that my newest lover was my husband's boss, and second, it was even more delicious each and every time he fucked me because his cock did things to me I didn't think were possible. It didn't hurt that my boyfriend was having fun with his wife, so there was no need to feel guilty related to Evan.

As the weekend wrapped up, it was determined that Jacob, my husband's boss, was now going to be my primary man, although we would likely still have episodes of four-way fun with Evan and Kara. It was also still probable that a different four-way fun would happen with Jacob and me plus my best friend Angela and her boyfriend, Steve. Jacob had already told me that I should plan such an escapade as he wanted to experience the wild Angela and I had already confessed I needed to see Steve again. Steve was a black man with a stereotypically huge penis. For me, his cock is really too big to enjoy every day, but also too big to not want in my pussy on an occasional basis.

So here I am, a crazy distance from the vanilla married woman I was a year ago and even many miles from where I was when I first sent my husband off on his trip locked in chastity and with denied contact. I was now with his boss, and I was with him hard.

Jacob set up this call with my husband and I was in his office wearing an outfit that was not appropriate for the workplace but that wasn't gonna remain on me for very long anyways. There is a very professional camera set up ready to capture all of Jacob's and my fun and project all of that to my husband.

Jacob had told me that he enjoyed fucking me a great deal, but he had to admit that fucking with my husband was quite a bit of fun too. I laughed when he told me this and welcomed him to my world. I learned that I loved fucking with my husband and the funny part was so did my husband. Although I had never fucked with him as hard as today would be.

We were just a few minutes from connecting with my husband. It was 4 p.m. where we were and 10 p.m. where my chastity boy husband was. His dick had been locked tight in a cage the entire time he was in Europe, while better dicks pleasured me pretty much on a daily basis. I sent him away under those circumstances fully understanding that part of the fun was humiliating him, I just didn't realize how far that would go. His boss was about to exert his dominance over me and us. I had my trepidations, but mostly I was just excited as hell.

Jacob looked at me and gave me my instructions. "When we connect, I will lead the call for a while, I'm gonna strip you and I'm gonna start fucking you from behind while you are bent over my desk. For him it's gonna seem like he is sitting in the chair in front of my desk, watching his wife gladly give herself to his boss, which of course you are gladly giving yourself to me. But once I've got everything set up, while I fuck you, you are going to tell him all about our fabulous weekend. He's already aware that we hooked up on Thursday as I gave him the basic description of that, and he knows we spent all weekend taking that hook-up to the next level. He just doesn't know the details. And his wife, while she is gladly getting pounded by my cock, is going to share the details with him."

As I heard Jacob's plan, my excitement grew. This was because any sex with Jacob was exciting, and second, I knew my husband was going to love this. We were going to give my husband something he wants; strong humiliation and a chance to see another man take me. My husband has a significant submissive side and watching his boss fuck me was going to test that side's depth. But I was still convinced my husband would ultimately love the next hour. Jacob explained he also was looking forward to it.

"I'm looking forward to hearing what you have to say and how you describe our weekend. I would describe it as somewhat life changing as now I'm going to continue to fuck you regardless of where your husband is located, and I know you are going to continue to let me fuck you because we both know ours is the best sex you have ever. So, when your husband comes on, just follow my lead until I tell you to start telling the story. Then the floor is all yours, and you can tell the story as you see fit. Sound good?"

I was standing between him and his desk with my butt leaning against the desk, And I straightened up and kissed him passionately and said, "You're the boss," and then we both laughed.

A few moments later the call connected and there on the big TV in front of us was my husband. As Jacob had instructed, he was naked, well, almost naked. On his little dick was the less than 1-inch-long chastity device that he had been locked in since the day he arrived in Europe.

"Hey there, Scott, great to see you. I understand you're doing great work over in Europe. I've been doing some work here too, and it's been quite fun. As you can see, your wife is here with me, and you already know she and I finally finished what we started on the dance floor a couple of years ago. Actually, we finished it over and over and over again this past weekend. So, sit back and enjoy the opening act of our show. I am going to get your wife naked and bent over my desk and I am going to start to fuck her."

Most husbands would be homicidally furious at this point. Not my Scott. He just stayed silent and enjoyed the show's prelude. Jacob kept the show, and my husband's humiliation going as he told the truth about where I was at.

"Your wife is very excited about getting stripped and fucked. Your sweet wife, the woman who sent you to Europe, Isolated and caged while she enjoyed herself is then going to tell you all about our amazing weekend It's a long story, but lucky for both her and you, I can go all night before you witness me filling your wife with my cum!"

As Jacob started saying all of this to Scott, he started to let his hands roam my body, and I immediately realized I didn't care who was watching. I just loved when his strong hands touched me. I just loved melting into his touch and giving myself completely to him.

From the first time I took his cock in my mouth while we drove to his house, to the end of the evening Sunday night when he slowly but powerfully took me in his bed, I have realized that while my boyfriend, Evan, is an incredible man, and has been pleasuring me since my husband left, I ultimately desire to be with Jacob. I just click with him, and my body just melts into his and each time he takes me it is soul-shaking experience, and orgasm!

I am wearing a red dress that is sleeveless and has a scoop front to it. The very first thing Jacob does is reach around and start fondling my breasts through the dress as he tells my husband that I am going to explain how I completely switched teams from team Evan to team Jacob. As Jacob verbally messes with my husband, I can feel the dampness in my pussy rise, and I have a strong desire for Jacob to mess with me in the form of fucking me long and hard!

He lets his hand slide around to the back and unzips my dress. It is quite a moment to know that I am about to have my clothes taken off in front of my husband by his boss. He pulls the dress down the length of my body, and I step out of it and now all I have on is a red bra and a red thong and a pair of hot-as-fuck stiletto heels. My husband can't see the heels, but I know they're there and they make me feel sexy and I know that Jacob thinks my ass is beyond perfect when I'm standing in stiletto heels. And if it pleases Jacob, it pleases me.

Jacob's hands go back to my breasts, and he starts enjoying their feel, and I certainly enjoy the feel of his hands on them.

"As I already told you, Scott, your wife and I have been intimate numerous times. You know, I've always thought that was a funny phrase to mean that we have fucked. So let me rephrase, your wife and I have fucked many times already. But since about mid-weekend, using intimate is appropriate. Yes, we have fucked and we have fucked hard, but we have also become intimate. Like right now, she is greatly enjoying my touch and is getting hot and horny. We are not just fuck buddies, but we are quickly becoming more than that. Your wife feels it, I know it, and you can see it as I'm enjoying getting her naked."

Jacob was not wrong. In just the one long weekend, he had moved in first place, and all I wanted was to feel him take me. I was a strong and independent woman, but I gladly gave myself to Jacob. I used my strength to be loyal to him and I used my independence as my free will to give myself to him fully.

Jacob, meanwhile, reached behind and undid my bra and whispered in my ear, "Take it off completely, so I can enjoy your breasts a little longer before I fuck you in front of your husband."

I did exactly as he wanted; his hands almost immediately went back to my uncovered breasts. His hands felt good as they kneaded my breasts and pinched my nipples. I was breathing heavily and moaning and was pretty much oblivious to the idea that I was doing that in front of my husband. I was doing it because the man who is now my primary lover was making me hot and wet and I wanted him badly.

"I'm gonna finish getting your wife naked and I think we all know that her pussy is ready for me. Isn't that right my little slut? Tell your husband just how wet and wanting your pussy is."

As he said this, he pressed himself against the back of me and I could feel his hard cock against my ass. God, I wanted him.

"Oh, baby, your boss is going to make your wife cum hard! And he will continue to do that anytime he wants because just this past weekend, the number of orgasms his cock gave me has already exceeded the number your dick has ever given me in our entire marriage. Remember how often you had to finish me with your tongue, well, Jacob finishes me with his cock like a real man! He is going to fuck me, and you are gonna watch and see what real sex looks like. You are locked in a cage and are going to remain that way for a very long time, I suggest you enjoy the view because viewing is all you're going to be doing and only occasionally when Jacob is being very nice to you like he is right now. He is letting you see something that you don't deserve to see, so make sure you are a grateful chastity boy and cuckold. Tell your boss how thankful you are that he is making my body tingle, and eventually he will drive me to an orgasm that will be stronger and better than any you ever brought me to."

Jacob laughed at what I said, knowing that it was just outrageously humiliating for my husband to hear. But it was also completely truthful. He stripped off my thong and told me to put my hands flat on his desk. He spread my legs slightly and now I was ready to get fucked. I noticed my husband was completely enthralled, but he still followed my suggestion.

"Thank you, sir, for pleasuring my wife and making her so happy. It is a great privilege to get to witness that."

I was proud that my husband responded as he did. He is my obedient pet, and he was enjoying this whole situation almost as much as I was. Jacob took control again.

"Scott, I'm gonna let your wife take over telling you about the weekend, I'm gonna use my energy fucking her. I want you to see how good I make her feel and know that I will make her feel that way almost every day you're gone. And just to reassure you, nothing is going to change when you return. I will still fuck her daily, and occasionally, when I am in the right mood, I will let you watch."

Then Jacob put his hands on my hips and told me to reach back and help him enter my wet and willing pussy. I didn't hesitate because all I wanted was to feel his cock inside of me again. My husband got to watch his cock-hungry wife insert his boss's cock into herself. Fuck that must has been humiliating. A primal moan escaped my lips as he pushed his cock all the way in. It felt perfect. I realized I knew what I wanted to tell my husband first.

"I am going to tell you all about the weekend, but first I just need to tell you how fucking amazing it feels when Jacob is inside of me. His cock is the perfect size, which, of course is quite a bit bigger and thicker than yours, But the thing that is game changing is that his cock head is massive and that ridge that protects it and surrounds it creates sensations inside of me that I never knew existed and now I am completely addicted to them. Each time he slides into me, his cock head pleasures me at a near perfect level. I will literally never say no to his cock whether it be here on camera with you, or in the hot tub with his wife and Evan, or right in front of you when you return. Jacob's cock owns me and being owned by it is the best thing that's happened to me in a long time. So, before we really get going on the story, I want you to just watch the pleasure I receive as Jacob fucks me."

I then looked back at Jacob and said, "Please take your time and fuck me slow and strong and bring me to my first orgasm. I want my husband to see the truth. To see that you are the best man who has ever fucked me. Then, after that truth is revealed via the orgasm you will give me, I will tell the story as you build a second orgasm in me like you have multiple times already. But first and foremost, I just want to feel the pleasure you provide me and then I can tell my husband how you did that over and over again all weekend long and how you're gonna keep doing that whenever you want because I certainly will never say no."

Jacob laughed and then answered by grabbing me by the hips and driving his cock as deep as it would go and then slowly pulling it almost all the way out and then driving it back into me. Oh, God that ridge felt good as it slid through me. I never knew that traditional intercourse could feel this good.

No one spoke as Jacob took me to my first orgasm in a slow and steady way. I started to pant and moan and finally my first orgasm exploded in me, and it had to look amazing to my husband as I was desperately trying to push back onto Jacob's cock, and I just kept repeating the word yes. And give Jacob credit he might be older man, but he was the energizer sex bunny and he just kept going. I finally calmed down enough to start the story.

"When I arrived with Evan on Friday afternoon, your boss, the man behind me right now pleasuring me at level you've never been capable of, kissed me and told me that he was looking forward to an amazing weekend. He then led me to his bedroom, and he didn't fuck me, he made love to me. It was gentle, but strong and powerful, and he spoke to me with clarity.

He told me that he had wanted me for a long time, and that the previous night was a dream come true for him to have me in the ways we had each other. He told me that I was his now and that his wife and he had already agreed that this weekend I belonged to him and Evan would belong to her. This hit me so hard I started to cry. I've never wanted a man more than I did in that moment. Think of the best, most powerful sex we ever had, and then recognize it wasn't even half as good as that time in bed on Friday night with Jacob.

He made me cum three times before he finally emptied himself into me. Three fucking times. You never made me cum that many times in a month, let alone in an hour! Feeling and hearing him climax felt incredible. I couldn't believe that I had actually made a man as amazing as Jacob happy and satisfied.

We joined Evan and Kara and they had obviously also just fucked. We ordered Chinese and ate and drank wine and we went into the hot tub. That is where more fun began.

Kara and I took turns giving the two men blowjobs. Each of us pleasuring the men back-and-forth. In the end, I was the one who swallowed both men's cum as Kara enjoyed dominating me a little. She held my head as Evan filled my mouth with his ejaculate, something he had done already many times since you left. And soon after, I was bobbing furiously on your boss's cock, and soon after that, I was rewarded with Jacob's mouthful, that I swallowed gladly.

The men were both very satisfied, and then what turned out to be a truly fun part of the weekend, Kara started to kiss me, and I started to kiss her back, and soon we exited the hot tub and went over to their outdoor couch and for the next 45 minutes Kara and I pleasured each other. Eventually the men got out of the tub and sat in the two nearby chairs and drank their wine and watched two women pleasure each other with great gusto.

Yes, that's right baby. Your wife is now a pussy licking lesbian, well not really, but I was for those 45 minutes, and I made Kara come hard. She and I are going to do that regularly because it was way too much fun.

When we were done, we went back to our men, but not the men that we started the evening with. I drove to their house with Evan, and Jacob greeted me with Kara, but I went to Jacob and Evan went to Kara and we excused ourselves into our separate bedrooms, and I am pretty sure they matched our fun, but all I do know is your boss continued to pleasure me late into the evening and early morning. He flat out wore me out but it was the best exhaustion I had ever felt.