The Sexy Cuckold Couple Pt. 01

Story Info
Cuckold couple becomes an owned couple.
3k words
4.31
292.5k
337

Part 1 of the 18 part series

Updated 06/08/2023
Created 10/14/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

First Encounter part 1

The first encounter arose in a very interesting way. My gorgeous wife, Jen and I were at my holiday work party when she whispered in my ear that she found my boss and the CEO of our company incredibly attractive and that he might be the one. I had seen them speaking earlier and knew that he would find Jen attractive. She had been by the office on a number of occasions, but had never formally met. Even more interesting was the fact that he lived just blocks from our new house and I mentioned that to her. Jen smiled and said that she now knew that based on their conversation.

My boss was a very fit, attractive, intelligent male with a lot of confidence. There were rumors that he was a player and enjoyed a number and variety of women. I guess I was not overly surprised that Jen found him attractive and did not think much about it prior to her whisper. The quick background on us is that we had a pretty vanilla lifestyle with kids, but loved to enjoy the wild side a bit when we were able to do so. We had communicated a great deal about the lifestyle, had played with some other couples and had even experimented with BDSM. Jen was bisexual and was typically showing more interest in other women than men which initially kept me feeling very comfortable about our relationship. As the years passed, Jen would often point out attractive men and I started reading and learning more about the presence of other men in a couple's life. The term "cuckold" was uncommon, but the more I read, the more excited I became about having another man, a superior man, enter our bedroom and our life.

We began to discuss more and more frequently the idea of other men and even fantasized about the idea. I was more on the submissive side while Jen was more on the dominate side and she always took the lead with other women and or couples. Now Jen was becoming even more aggressive in our own bedroom and she would whisper in my ear, while making love, how she wished there was a different cock, a larger and thicker cock penetrating her. She began to tease me about my small size even though I felt normal in that department. When inside her, I could last a reasonable amount of time unless she transformed my thoughts to the submissive side and in doing so, would cause me to cum very quickly. Just the mention of a bigger, superior cock would cause me to spurt inside of her and this was becoming more common which led to additional conversations and additional fantasies around cuckolding.

Jen really embraced the idea of humiliating me more and more and it was exhilarating as I quickly learned that I enjoyed and actually loved the torment and degradation. A portion of my life was transitioning towards true submission and servitude of Jen and her desires and I embraced this. Just one example was the fact that Jen was now forcing me between her legs after I came inside her. Previous to our exploration of the cuckold lifestyle, I had enough stamina for us both to experience orgasms, but with this new transformation, she was rarely having orgasms while fucking. This was a great solution for her to have me between her legs and bringing her to orgasm while I cleaned her of my own cum. So while we considered ourselves newbies in the actual world of the "cuckold" lifestyle, we were living a part of it and very interested in bringing the Bull portion into the equation.

Jen whispered again for me to follow her and I politely removed myself from the current conversation and followed her to the bathroom. She locked the door, lifted her skirt, took hold of my hand and shoved my fingers inside her drenched pussy. I was incredibly surprised at how wet she was and in a confused manner, said Brian...my mind raced as I was excited about the idea of another man in our life, but this was not the person. How could Brian, the person who controlled my work life, and our finances, be the man Jen wanted to engage with for this type of behavior? Jen speculated, I bet Brian is very well endowed. My mind regressed back to the gym locker room where I frequently saw Brian. He was not just well endowed, but huge...his cock must have been 7 inches soft and very thick...I snapped back to reality. I immediately avoided the question or statement...instead I said we could absolutely not engage with Brian and that the idea was just crazy. I further justified it...we were really seeking a kinky type male that would not only want to have amazing sexual encounters with Jen, but also would want to engage with us as a couple and control, dominate and humiliate me as part of that relationship.

It was difficult to hide as I started to feel hot and felt my small cock further harden in my dress pants. In my mind I was thinking...Brian was very much this type of guy and likely exactly what we were looking for had it not been for the fact he was my boss. He was very confident (on the border of arrogant to the men in the office), absolutely loved and needed control (ruled the office like a dictator), and was often disrespectful to his subordinates, including me (frequently saying derogatory things when we disagreed or things did not go his way). Even more on par, was the fact that there had even been a rumor a year ago that one of my former colleagues had been fired because he caused some strife and a bit of an uproar about the fact that Brian was having an affair with the man's wife. Jen noticed my cock and rubbed it asking if I was sure about the fact that Brian was not the right Bull for us.

Immediately I snapped back to the present and said there was no chance that Brian was that type of guy or that this was a possible idea. She could not know any better so I thought the conversation was done and we exited the bathroom back to the party.

The cocktails and wine continued to flow throughout the night and as things were starting to wind down we made our way to the door. Brian swiftly met us there and insisted we stay for a bit longer. I thought this was odd, but again did not want to be rude to the host, my boss. He quickly brought us into a small crowd and included us in the conversation. It was very general, but as I would learn later it allowed the party to thin out and within the hour, we were narrowed to five people...one of my colleagues and his wife, Brian, Jen and myself. Brian said to the small group that Jen had been asking about his wine collection and he was going to give her a quick peak leaving the three of us to converse. It was odd to me, but Brian did so very smoothly...it was more of a statement than an offer for others to join...still I did not sense that my colleague or his wife thought it was strange which comforted me.

After some small talk, my colleague and his wife departed leaving me alone while my wife and my boss were exploring his wine collection. The house was incredibly large and I felt weird trying to venture about trying to find them so positioned myself on a curved couch along the wall in the massive foyer waiting for them to return. My mind was racing as to what may be taking place, but my wife and I had spoken endlessly about how the overall cuckold situation would unfold...Jen and I both agreed and wanted the same thing...there was no desire to play without me present unless the future unfolded in a manner whereby we agreed that it made sense. Still, my mind wandered and even a bit of jealousy started to arise within me as Jen and Brian finally entered the foyer where I sat. Immediately I saw that Jen was flush and I felt a combination of being sick to my stomach and an overwhelming feeling of humiliation. I wanted to scream as I sensed what had taken place, but yet I remained quiet and passive. Even with all the racing emotions within me, my little cock had grown incredibly hard and even though small, the marginal bulge was easily visible in my suit pants. Jen noticed which provided her great comfort and confidence...not that she needed much as the alcohol had clearly taken its toll on her. She turned to Brian, gave him a short, but erotic kiss on the lips and thanked him for the "amazing tour".

I was unsure what this meant, but before I could think further about it, Brian took hold of Jen and engaged in a much longer and deeper kiss. His left hand slid from the back of her neck to the curve of her back and his right hand grasped her bubble ass clothed by her tight sexy black dress. It was short and he reached underneath and slid the dress up so that he could feel her naked ass given she wore only a thong underneath. They both moaned and it felt like minutes that they were intertwined with one another. I was numb and paralyzed and did not know whether to grab my wife and leave or to enjoy what was transpiring. My little cock danced in my pants so it was impossible to hide how excited I was. The embrace finally ended and Brian looked at me. You two run along as you and Miss Jenny have a lot to discuss tonight about your desires for a cuckold lifestyle. My heart raced at his comment as she must have told him that she was my Domme and controlled me in the bedroom, and further about our exploration for a Bull to enter our lives. I was furious given the conversation we had earlier this evening. Still there were no words escaping my mouth and Jen broke the ice by tapping my small bulge...looks like cucky here is excited to have that conversation Brian. I blushed and turned immediately to walk out trying to hide and ignore what was taking place.

As I opened the door, I felt an intense urge to piss. I had not done so all night and the booze had snuck up on me. Without thinking that I was only a few blocks away, I sheepishly asked Brian if I could use his bathroom. What came next was an incredible surprise...Brian sternly said that I was being disrespectful by not appropriately addressing him as Master, that I would soon enough learn my place as his "help". He sternly communicated that I could use the yard for such acts, and then he paused. He said, now that I think about it, both of you have consumed a lot of alcohol tonight and it would be wrong to allow you to drive home. You will remove your clothing and can walk home from here. Both Jen and I looked at each other in disbelief. Brian stroked Jen's cheek and said, let me help you my pet. I stood there in a trance as he unzipped her little black dress. She was as stunning as the day I first met her standing there in her matching black thong and thigh high stockings. Brian told his new pet that she could keep the stockings on but simply pointed and Jen immediately reacted and removed the black thong from her body.

Attention then shifted to me. I bumbled around getting my suit off and then had a moment of real anxiety. Miss Jenny had required me to wear matching black panties this evening. I quickly begged to remain clothed from the waist down, but to no avail. I pulled my pants and panties down together to avoid that embarrassment revealing my incredibly hard cock. Miss Jenny then commented, oh look at cucky's cute boy clit...why don't you show Brian your nice panties honey. I was in a deep submissive state and was mesmerized at what was taking place. I complied and lifted my black panties up my legs and positioned the thong properly between my cheeks. Brian laughed out loud as he fondled Jen's naked back. He said, you can keep those on cucky...it hides that pathetic cock of yours. He turned to Jen and said clearly, you were right, he has a tiny one and I think the term boy clit is very appropriate.

As we stood there, Brian continued to fondle Jen and his large massive hand slid between her legs. Sternly he ordered her to spread her legs. Jen quickly complied and immediately he shoved two of his thick fingers into her dripping cunt. There was a loud squishing sound as he roughly pounded his long fingers in and out of her and she moaned loudly as he did so. Her wetness was evident to us all, and Brian commented to me, wow, your wife is very excited...does she get that excited with you? Without answering, I remained stuck in a trance watching his fingers assault my wife's pussy. After a few minutes, I sensed that Jen was nearing an orgasm on his powerful fingers, and Brian must have sensed that as well as he immediately stopped, yanking his thick fingers from her drenched pussy. Sternly, he told her, you are not allowed to cum without my permission slut. Now both of you get out of here...again, there is a lot for you to discuss.

Like robots we turned, left Brian's door and started our departure. Brian quickly stopped us from his doorway commenting, right there cucky...you can squat and piss there in the yard...oh and no removing your panties...I want to see you piss in them while squatting. I did not think I could feel anymore humiliation this evening, but was clearly wrong. We moved to where Brian directed us and one of his bright outdoor lights immediately went on which was directly on me. Miss Jenny chuckled nervously for me as I squatted. She patted my head like a dog but it brought me enough comfort to relieve my bladder and my piss raced out spraying through my black panties onto the grass, my ankles and feet. Brian laughed...good cucky, now get home my pets.

Jen and I did not talk much on the way home other than her slightly apologizing...I am sorry, but it was like Brian could look into my soul and read my mind. She said, I found myself opening up about our life, our kinky sexual desires and about how we needed a dominant, controlling Bull in our lives...and honestly I think he perfectly fits what we are seeking. After scurrying home and entering our home through the back, we dressed, poured some coffee and engaged in a deeper dialogue. Jen shared that they did not engage in any sexual activity other than some petting and a lot of kissing. She told Brian that she wanted me present for anything sexual as my humiliation and degradation turned her on immensely.

Surprisingly, he strongly agreed and had told her that it was imperative to have me there as a huge part of the turn on for him was taking a man's wife in front of her husband, having her experience incredible orgasms on a superior cock while her husband watched in utter humiliation and ultimate emasculation. He further commented how the husband needed to be obedient, serving them both as they deemed him fit...that the husband would be forced to engage in derogatory acts unimaginable to most of our society. Brian was able to extract freely how we were looking for a Bull to engage with, teach us, and ultimately use for his selfish pleasures. After extracting that information, Brian had laughed as he hoped Jen would be open and candid, but it was not required at all. In fact, Brian continued telling Jen that he had his IT guy look through my work computer and found that not only was I on various cuckold sites and posting things frequently about our desires, but also that we (Jen and I) were emailing back and forth about finding a naughty and devious Bull to enter our lives.

He seemed to know everything and was just so pleasantly surprised when he met Jen, how beautiful and open she was. He told her how he felt he had hit the jackpot. His instruction to her was simple...we could either agree to be his pets and maintain our current lifestyle or he would fire me for insubordination and make sure it was difficult for me to ever find a job in this field again. He may even share some of the sites and postings with friends and family should we not agree. If we did agree, we would be able to maintain our vanilla lives as is, our kids and family would never know or learn about this aspect, but when in his presence, we were his property, we were his ownership to do with us as he pleased. Miss Jenny would still be dominant over me, but he would be our Master and would control us both. He told Jen she would be fucked, stretched, abused, and used in ways she never thought possible and I would have to succumb to extreme degradation and humiliation...again, more than ever imaginable. While neither of us knew what specifically Brian had in store, we realized there was not much of an option for us. I could not be mad at Jen as this would have transpired even without her flirting, but I could not help but wonder how life would be going forward and how the work environment would change given Brian would not only be my boss, but the Bull in our relationship...fucking Jen at his whim, and using us both as pawns in his life as our ultimate Master.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
16 Comments
rickylaw01rickylaw014 months ago

With a few secret recordings this guy could sue his boss's company and the boss personally and walk away with a fortune

CuckRick1952CuckRick19529 months ago

Great story can't wait for the next chapter!

CuckRick

AnonymousAnonymousover 1 year ago

Not a big fan of story's that fuck with someone's work and home life where kids are involved. I would have dared Mr CEO to fire me, then sued him when he did.

Sissyboy48178Sissyboy48178over 1 year ago

This is sounding like a very erotic fantasy so far. I'm looking forward to reading more. Great beginning of a wonderfully decadent story.

AnonymousAnonymousover 2 years ago

How old are their kids? We don't know how many they have nor their ages (kids and parents). Since there are many more chapters to read I am hoping that their lives are not going to be destroyed and that there is some reasonable time limit to their blackmail. I am also hoping that there will be an ending to this story and not left with an unfinished storyline. I like cuckold stories that humiliate the wife and/or husband and activities that really degrade them; I also prefer stories like this that end with the husband and wife finding out that they are stronger together and have the rest of their lives (kids and future grandchildren) with the sordid period of time behind them.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Anna Succumbs to Neighbor's Cock With encouragement of husband, wife becomes more daring.in Loving Wives
Willingly Cuckolded for Love A happily married couple both submit to her Dom ex-lover.in Fetish
Cucked on Vacation With encouragement, wife submits to a hung black gentleman.in Interracial Love
My Daughter made me Cuckold Him Ch. 01 My daughter and boss made me cuckold my husband.in Loving Wives
He Let Them Have Me #01 A charismatic man turns wife into slut and cuckolds husband.in Loving Wives
More Stories