He's the Boss Pt. 01

He's the Boss - Part 1

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This is a cuckold story. There you have been warned.

Thanks to a friend who encouraged me to find time to write again. I am hoping this story gets me back into the routine. I hope you enjoy it, and I will do my best to get this and other stories moved forward over the coming months.

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I was at my desk, already hammering away at the long to-do list I had for the week ahead, when a text from my boss made my phone chime.

Traveling with your wife doesn't suck.

My boss never missed the opportunity to tease and humiliate me. The next text was the photo I knew was coming. He loved sending me photos of my wife and the truth be told, I admired his photography skills and his ability to capture my wife looking hot! In the photo my wife was at the table across from him with a coffee and a smile that said last night was great.

The smile says it all, doesn't it!

My boss also knew how to press my buttons. My wife's ample breasts were showcased by the outfit she was wearing and the ring I gave her hung on a chain on her upper chest and the look was hot AF and yet he gut punched me not by pointing out those, but by pointing out her smile. That smile used to be reserved for me, now he saw it much more frequently than I did.

Six months ago, there was never a smile on her face when my boss was involved. She hated him. First, she said he worked me too hard and took credit for all the good things I accomplished, plus he was always fairly cold when he interacted with her. That all changed when he invited us to dinner.

He promoted me and offered to take me and my wife out to dinner on the company tab to celebrate. We went hesitantly but then Mr. Allen was gracious and praised my work. He said he was very impressed with how I handled all the extra work he had given me. He told me it was a test that many of his right-hand men had failed in the past, but that I had shown him real effort and great results. He was also gracious and kind with my wife, engaging with her warmly. We ended up having a good time.

Soon we were working well as a team and being social. I started to notice my wife's distaste for Mr. Allen was replaced by flirtatious behavior. I had no issue with this as my biggest fantasy was my wife cuckolding me. We even started to have hot sex as she teased me that perhaps she had misjudged my boss and maybe she should thank him for my promotion the old-fashioned way! Life was good and it was soon to get better.

About a month ago, we were out for an early happy hour on a Friday afternoon and just as we sat down and ordered drinks, both of our phones rang. There was a major issue with getting an order out to a key customer. That was really my lane, so I excused myself and headed to our building to get things straightened out. I winked at my wife as I exited and told them to hang tight and I would get it fixed and be back before round two of drinks. I was hoping that some of our fantasies would move towards reality as I got in my car. I texted my wife one word: greenlight. She liked my message and while I fixed the work situation I had to concentrate not to do so with a tent in my pants.

Mr. Allen and my wife stayed back to drink the first round we had already ordered but the plan was he would drop her off and join me if I needed him. It turns out the problem was easily solved but did take a few hours, so the plan changed and we decided to meet back at our house and order Door Dash. By the time I got there the flirting between my boss and wife had accelerated and they were sitting on the couch next to each other and I noticed her shirt was unbuttoned by one extra button and she was flushed, and her nipples were hard.

Now most men would have been mad and intervened immediately. But I am not most men, and I had no bigger fantasy than watching my wife be with another man, and adding to that, my favorite other man fantasy was my wife with her boss (he lways flirted with her), but my boss was a close second. So instead of intervening, I grabbed myself a drink and sat in the chair across from them and said nothing. I was curious to see where this would go, and I was rooting for it to go all the way. Boy did I get my wish!

Sarah, my wife, looked at me and I nodded, she knew my fantasy and the nod was my second greenlight message of the night. She turned towards my boss and kissed him. He didn't hesitate to return her kiss. Then his hand went up and he started to molest her breasts. Soon they were making out like horny teenagers and her shirt was completely undone. I just watched and rubbed my hardening dick through my pants. For a cuckold wannabe like me, this was shaping up to be a perfect start to the weekend.

After ten minutes of hot and heavy kissing and petting, Sarah stood up, took off her shirt fully, then unclasped her bra and let it drop, showing off her DD cup breasts to my boss. She climbed on his lap and presented her tits to him. His lips went right to her nipples and my wife moaned in pleasure. I moaned in arousal and Mr. Allen enjoyed himself. Everyone was happy and everyone was going to get happier.

After 10 more minutes of kissing and breast fun, Mr. Allen looked past Sarah to me and said, "Which way to your bedroom?" I pointed in that direction and he and Sarah disentangled and then headed in that direction. I did not try to follow but instead let them have their privacy. They left the door open, so I got to listen to my wife get fucked by my boss. She screamed in delight as she came hard. I came a moment later, and based on the sounds coming from the bedroom, Mr. Allen had staying power and brought my wife a second orgasm before he yelled loudly and claimed my wife as his by cumming deep inside of her.

A few moments later Sarah came out, she was fully naked and had the look of a freshly fucked and highly satisfied woman. She leaned into me, kissed me, and said, "THAT was incredible. I hope you enjoyed that as much as I did. Scott is staying the night, so you are relegated to the couch in the basement. Enjoy the sounds of some seriously great fucking. Your boss is hung, and he knows how to use it! Your wife is going to have a VERY fun night!"

I smiled at my wife, and said, "Enjoy yourself and please don't be quiet!"

She laughed and said, "There is no chance of me being quiet!

She was accurate. I spent the evening masturbating to the sounds of my boss pleasuring my wife. I did fall asleep late and when I woke it was quiet. I went upstairs and was headed for the kitchen when I heard my wife moan. The moan didn't come from the bedroom, but from the kitchen. As I came around the corner, I was met with the sight of Mr. Allen sliding his cock in and out of my eager wife as she was sitting on the edge of the kitchen island. He was in no rush and was pulling himself almost all the way out and sliding back in. I stared and immediately grew hard in my pajama bottoms.

They cared not that I was watching and he slowly but strongly fucked my wife. Eventually his pace increased, and I witnessed a real man taking my wife and making her happy. They came hard together and then started kissing. Eventually he pulled out of Sarah and turned towards me, "We are going to go grab a shower, can you make some coffee, we got distracted!"

They walked by me and headed to our walk-in shower. I made coffee and eggs and toast. When they returned and sat, I served them breakfast. That is what a good cuckold does and being a good cuckold was a dream come true for me.

After they ate, my boss initiated the conversation. "So, according to your wife, last night, and this morning and well, everyday in the near future is going to be great, because she LOVED our sex, and so did you because your fantasy is that your wife has a lover and the extra kick on that fantasy is that there is a boss involved. Is that correct?"

"It is." I decided there was no use denying it, and no benefit to saying more.

"That's good, because I am not going to stop fucking your wife. Today was the start, and definitely not a one-time thing." Then he turned toward Sarah and said, "You got any issue with us being a regular and frequent thing?"

She laughed and said, "I have no issue at all, you can fuck me anytime you want!"

Mr. Allen put his hand over onto my wife's knee and said, "Oh, I will. In fact, give me a moment to set a few rules for your hubby, then I plan to take you back into your bedroom and make you cum, preferably loudly!"

Sarah laughed and said, "Rules, oh my hubby loves to obey rules, but make it quick because I need that perfect cock of yours back inside of me." I am sure that statement was true, but I also knew Sarah was enjoying teasing me. She knew that I didn't just want to be cuckolded, I wanted to be teased and humiliated too. Hard to explain that to most people, but Sarah knew my fetish was genuine and she was enjoying it greatly herself and making it even better for me.

Mr. Allen smiled and said, "Why don't you just climb on board right now and you can ride me reverse cowboy style as we set some things in motion. I bet my employee over there would get a thrill watching his boss fuck his new girlfriend!" I moaned as he said this. I had become a cuckold, and it seemed my boss knew exactly how to make that even better by being the Bull that I desired. I wanted the man fucking my wife to be THE man and I wanted him to assert himself over me. Mr. Allen was doing so perfectly.

Mr. Allen was wearing a pair of my sweats and he stood, pulled them down and his cock was revealed. It was impressive and my wife pulled off her yoga pants and while facing me she lowered herself onto my boss's cock while staring directly at me. She started to pleasure herself and as she did Mr. Allen lifted off her tank top so that her big, perfect breasts were fully on display. He immediately started to fondle them as she rode his cock.

"First rule, these perfect tits," he squeezed them both as he said it, "and her exquisite pussy, totally off limits to you. Let me hear you say it!"

"No sex with my wife, and no touching her breasts." I was obedient. I wanted to be obedient. Obedience was only second to humiliation as a turn-on to me.

"Very good, rule two; you have 48 hours to purchase a small chastity device and lock yourself up."

My wife pressed herself hard onto Mr. Allen's cock, turned her head towards him and said, "Oh, he already has one." And then she turned to me and said, "Be a good boy and go get your cage! I promise I won't cum on your boss's cock until after you are all locked up!"

I did as instructed and brought my cage back into the room where my boss and wife were fucking. And after just watching them enjoy each other, they acknowledged my return. My wife issued the command.

"Strip and lock yourself baby and give your boss one key and me the other!"

I did as instructed and put on my less than one inch long cage. It was very small, and I had to work to get myself into it as the sights and sounds of them fucking had me aroused. I got myself inserted and locked. My desire to be obedient simply overpowered my arousal!

I had worn it for as much as a week in the past, I was pretty sure I was about to start on a journey involving a much longer lockdown. Mr. Allen laughed when he saw me all locked up and laughed even more when I handed him one of the two keys. He was fucking my wife and now he was also one of my keyholders. Life was good for him!

I gave the other key to my wife. She took it and said, "I think it is safe to say we won't be needing this for a while!"

Mr. Allen laughed and said, "Final rule: go get a gold chain from your wife's jewelry box, I saw a few in there, and then take off her wedding ring, and put it on the chain. Then hand it to me." I was waiting for more, especially the why of this command when he said, "Now, cucky boy!" I went and got a chain, came back and my wife held out her finger. We both only wore wedding bands, so I slid it off of her finger, the finger I had put it on about 5 years ago and strung it onto the chain. I handed it to Mr. Allen who proceeded to put it around my wife's neck.

"Sarah, your wedding ring around your neck is the reminder that you are mine and while still married to your husband, he and his ring have just been demoted to second place. Think of it as the reminder who is boss!" As he said this she reached up and held the ring out in front of her and said, "Perfect! I love it!"

Then Mr. Allen grabbed her arms by the wrist and pulled them to her side which fully impaled her on his cock. From there he started to really fuck her. She lost all control and bounced back on his thrusts with all her energy. The ring bounced wildly against her chest, and I was mesmerized by it and watched it as I heard my wife and her lover cum hard together. They wound down from their highs, and he gently massaged her breasts. She grasped the ring again and said, "I think cucky likes this last rule best, he just watched it as my real man fucked me, isn't that right baby, does the sight of the ring you gave me on my neck, not my finger drive you wild?"

It did. I told her yes. She held it out and told me to kiss it. I did. "Thank Mr. Allen for such a great idea!" I did. My humiliation was so high, and my dick pushed hard against my cage. But the reality was I was in cuckold heaven.

"Baby, I think I will spend the weekend with Scott. Mr. Allen to you of course. Is that OK lover?" That last part was directed at my boss. He said definitely. For the next 15 minutes my wife packed up some things and Mr. Allen drank the coffee I refilled for him. As they left, he said, "see you at the office on Monday!" And he left with my wife.

Since that first weekend, my wife and Mr. Allen have had a torrid affair and I have spent the entire time locked in my chastity device. Last week Sarah informed me that my boss had invited her to join him on his business trip. They were going to be gone for almost 10 days and she said they were not going to hide their relationship. Then she laughed and said, "Oh, and the keys are traveling with us. It will be such fun to know you are locked tight while we are free to be a fun and sexy couple. Doesn't that sound great!"

Actually, it did and I said, "It sounds perfect!" and Sarah smiled and kissed me on the cheek and said, "Good boy!" I loved it when she said those exact words.

They left yesterday and as they departed (I drove them to the airport) my wife handed me her phone. "Keep this for me, I am going to focus entirely on being the perfect date for my man and the phone will only distract me. I changed the pin, so just put it somewhere safe for when I return. But for the next 10 days I am entirely this man's woman!" She leaned up against my boss as she said it.

Mr. Allen wrapped his hands around her just below her breasts and said, "Don't worry, I will be sure to send you a few photos and updates, I don't want my best employee and our obedient cucky to go totally without contact!" With that, my boss grabbed my wife's hand and they walked away.

The text of her drinking coffee was the first of his promised updates. I enjoyed it as the cuckold I am and looked over at my task list. He had left me a long list of things to do. In the second column was listed his to-do list. It simply read, "pleasure your wife." I realized I could already cross that one off, but I didn't because I knew that was a task my boss was going to enjoy completing every day. And the truth was, I was going to enjoy it too, just like I would enjoy his next text and next photo. I got back to work. I had my work to do, and he had his. His involved fucking my wife, and mine involved enjoying that thought.

Thanks for reading and I hope to publish the next chapter soon.