The Perils of Cuckolding

Matthew Richardson Columns, Lawyer 17 Comments

I think it’s high time I get back to sharing some shameful tales over the past year that you’ve missed out on. May as well start off with the worst one. Most of the stories, I’ve told make me seem pretty deplorably, and frankly, I am. But, I still have some minimal code of ethics, boundaries even I won’t cross. At least I thought I did. I stupidly crossed one recently and am still paying the price for it. A few months back I committed one of the cardinal sins a human being can commit. I slept with a married chick who is married to a guy I work with, and it’s costing me my sanity.

Before you judge me, let me give you a little back-story, Nicole worked on my floor for the past 2 years and works in my group. We have spoken maybe a dozen times, mostly work related. I’ve stared at her abundant cleavage in a conference room for lack of better visual aids, but I never ever considered hooking up with her. For starters, she is terribly unattractive, (fat, bad teeth, dead hair) but you know that hasn’t stopped me before. Having sex with unattractive girls who are lionesses in bed should be a staple of every single guy’s diet and certainly is one of mine. Let’s be honest, there’s only so many times you can have a hot chick not blow you or give you any sort of sexual satisfaction. However, Nicole also seemed like the type that was also a terrible lay, so she really held zero appeal. Also, there was the trivial fact that I recently noticed her rocking a large engagement ring. Since I don’t give a crap about her, I didn’t bother to find out who the lucky bastard was. I never figured it would have any significance in my existence on this planet. Big Mistake. FYI, If you ever end up sleeping with a woman who is married, it’s best to know in advance who you have wronged, so you can keep an eye out for his vengeance.

A few months back, we had our group outing at a fancy Italian restaurant on the Lower East Side. I sat between a partner I actually like and Marcus, my buddy and younger associate I have been attempting to mold in my image for years. We drank heavily. After dinner, the crowd thinned out and a few of us went to generic upscale lounge. I honestly have no idea where the next two hours went, or how things led to this moment, but next think I knew, a meaty ringed hand was firmly clasped to my leg. I looked up and saw a pretty decent looking blond girl. It literally took me a few minutes to process that this was Nicole. She looks a lot better when I’m drunk and she has make up on and presumably spanks.  My first instinct was to start sucking face, but then I notice other colleagues still floating around the bar. Upon closer inspection, it was only my friend Rachel who was busy trying to sleep with a partner who hates his wife and kids, so I knew we weren’t in any real danger of being outed by two other shadeballs.  So I proceeded with a degree of caution.

Me: What are you doing?
Nicole: Let’s get out of here.
Me: I live a few blocks away.
Nicole: Don’t tell anyone about this.

She wants discretion. Good. Fuck caution. All systems go. We stumbled into the street and walked a few blocks trying to hail a cab.  I spotted a cab and the second I let go of her to put my arm up, her heel got caught on the street and she stumbled forward. She staggered around like a wounded bull who just got jabbed in the gut by a bullfighter, and then she fell face first into a puddle. It was the kind of slo-mo classic movie stumble, that if I were so inclined, I probably could have swooped in to stop. Instead I watched her fall flat into a disgusting NYC pool of mud and hot dog water. I was completely reviled by the sight of her fat puddly body. By all rights, that should have been a sign from God telling me not to follow through with this. But I ignored him like I usually do and shoved her fat quivering body into the cab.

We stumbled through my hallway and into my apartment. No small talk, no chitchat, straight to the bedroom. I made sure the puddly mess disrobed before touching my Egyptian cotton sheets.  She removed her spanks and I climbed on top of her amorphous blobby mass. After a 4–6 minute piss poor performance by me (I could blame it on her looks or the mass quantities of booze, but that would be unprofessional of me), I got up and put my pants on to start guiding her out back into the wilderness.

Her: It’s late, do you mind if I stay the night?
Me: Are you insane, what is your husband gonna think?

Sadly, that was the first time this ethical dilemma even registered for me and only because I truly was repulsed by the thought of her sleeping next to me.

Her: I’ll tell him I slept at a friends.
Me: Absolutely not. You have to leave.
Her: Fine. Jerk. I’ll go. But promise just to act normal when you see him tomorrow. Don’t be weird.
Me: WHAT???? Why would I see him ever?
Her: Because we all work on the same floor.
Me: (sobering up a bit) Come again? What now? Who are you married to?
Her: You’re joking. You know I’m married to Andrew.
Me: Andrew the squirrelly looking tax guy, that uses the same bathroom I do everyday, holy shit, what the fuck were you thinking?
Her: Relax. It’s no big deal.

With that bombshell dropped, she tried to casually roll over and fall asleep. I sat up furious and suddenly alert, and demanded she go home to her poor cuckold immediately. I started shoving clothes towards her and I think she realized her suggestion of a slumber party was utterly insane.  I’ve been in bad situations before, I know the answer is never to say screw it let’s make it much worse. She got dressed, I shoved her into a cab without any more words exchanged. I took a deep breath. Even for me, a new low had been reached. I could barely sleep the rest of the night.

The next day at work, I was on edge. I’ve done a lot of scummy things, but I try never to put myself in a position where someone might have good reason to murder me.  First I had to find out if anyone knew anything. I was worried that anyone actually saw us leaving the bar together, but after talking to Rachel (the only other associate left at the bar), it was clear she was focused on whether anyone had seen her doing anything shady with the married partner. So it seemed clear the only people who knew about this were me and Nicole. I thought long and hard about my options:

  1. I could come clean and tell Andrew I made a terrible mistake.
  2. I could wait for Nicole to tell Andrew and have him attempt to murder me.
  3. I could say nothing, hope she said nothing and live in fear for the rest of my life here.

Obviously I chose option 3. Who the hell ever comes clean about something like that? Surely, Nicole had nothing to gain by admitting her sins to her cuckold. I got an email from Nicole that morning asking me if I could drop off a bracelet she left in my apartment. I didn’t respond, but I had brought the bracelet to work, so I simply inter-officed the bracelet down the hall and chose never ever to speak or look at her again, outside of forced work interaction. I have no idea what motivated her to cheat on him and I don’t care. I can only assume she chose me because she assumed I would be stupid enough to take the bait (I was)  and that I would take it to the grave. Also correct. I am likely to bury this dark secret with the rest of them in my overflowing closet of scumbaggery. Now all I had to do was avoid getting murdered by the cuckold. After all, I couldn’t know if he knew that he had been cuckolded. And I couldn’t know how a cuckold would react to being cuckolded. (Sorry, once you’ve been involved in cuckoldery, typing the word becomes addicting.)

For some reason this newfound edginess made me race to the bathroom every five minutes that day. Every time I went to the urinal, I started looking into the silver pipes to see if he was behind me with a butcher knife. A few days later, I was mid stream, with my head angled towards the door (the pipe reflection method proved ineffective) and I saw his squirrelly face. I nodded and quickly stopped my stream, trickling some pee on my slacks. I flushed and turned to face my accuser. I had visions of a naked Eastern Promises style knife fight. Part of me was relieved there was no butcher knife, but part of me was a bit disappointed when there wasn’t. We muttered greetings to each other and I walked out, hands unwashed. I have seen him a few more times in the hallway and he has made no indication that is wise to our sinful ways, but that doesn’t mean he’s not lying in wait, ready to strike when my guard is down.

It’s been over 4 months and I’m still on pins and needles every time I take a piss. I’ve recently resorted to being the guy that pees in the stall. It’s downright pathetic. I’m sure part of me feels guilty that I made a cuckold out of this innocent schmo, but I’m mostly annoyed that I can’t pee comfortably in my urinal anymore. So let that be a lesson to you. If you bang another man’s wife in your office, be prepared to give up your urinal privileges.

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  • Strenuous Objector

    I’d say the focused lesson is what you said first, always know the guy you wronged because if you knew it was a guy in the office you probably wouldn’t have guided orca to your place. Then again, I keep my mouth shut, prepare my lines for if she doesn’t, and just go with it. I mean, if he’s going to kill you it’ll probably be with a gun so I doubt your law firm ass could dodge that from your urinal position. Might as well assume no one will ever know and move back on to summer associates.

  • MagicCircleJerk

    Be a true alpha. Realize you now own this guy in every way shape and form. Lose your fear. Otherwise, despite my usual don’t shit where you eat policies, well done.

  • Juris Depravis

    Point of parliamentary procedure: Is he REALLY a cuckold if he does not know about it (or watches or “cleans you up” afterward)?

  • MeanPartner

    You are a scumbag for doing it with an unattractive person. You are a fool for doing it with a married woman. A total idiot. Who are you? Schwarzzenneger of the east? Of course she’ll blab to him one day. Out of spite. Or in a play for tearful forgiveness. He’ll never say a word. Then one day your car will skid and rest on a cliff, too delicately balanced for you to get out. The relief you experience at an approaching car will dissipate faster than a man leaving Alma in midsentence at a bar. He’ll tip your car. A partner will call you in one day raging that “XYZ document” didn’t get filed on time. “But I put it in the box of motions to be filed” you’ll screech. “Malpractice” he’ll say and your career is doomed. You’ll just know He fucked with you somehow. When excessive amounts of porn arrive in the mail addressed to you…when someone knocks on your door at night…when a neighbor accuses you of scratching his car…when you travel abroad and are stopped at Customs…when anyone invites you to go hunting… When even Alma stops talking to you. Nope. I wouldn’t be you now for anything.

  • miserable associate

    Funny article, but you’re a real piece of garbage. If any girl is stupid enough to marry you, you can be sure karma will rear it’s ugly head and she will bang one of your paralegals.

  • Sid

    Thanks for perpetuating the stereotype that lots of sleaze happens in lawfirms.

  • Quadoz

    Ehh don’t listen to these people. You did what you did. I’ve done plenty of terrible things with married women.

    She will blab about it though. Women are run by their emotions. She will get all worked up one day and slam it in that guy’s face. Just remember one thing – DENY DENY DENY.

    You will need to land a few hot chics though. The orca brought down the batting average. You can only have so many chics wearing the mascot uniform in the team photo man. Clean up that average!

    Keep playing the game brother, you’re not alone out there.

    City Cop by night, Rookie lawyer by day.

  • Guano Dubango

    Matthew, my man! Way to go. So what if the woman was not attractive? She had “parts” and you needed a tight fit.

    Not sure if the effort was worth it. In my country, a man can get castrated for humping another man’s woman, even without benefit of marriage.

    You should check to make sure you did not pick up any thing. Although not possible here, it is best to find another place to bang than your place, because you can have trouble getting rid of the woman after you have made your night deposit.

    I recommend, for unattractive fat women, that you use the freight elevator, which is never in use after 5:00 pm. This way, if the door should open suddenly, you can have the excuse that the elevator was stuck and you were passing time because you were bored. And they may not even know what it is you were doing, because you can always say you were not having real sex, instead you were just “caught up in a wrinkle”. That works for me.

    • Jerry

      You can’t your girl get piped!

  • TK

    Thanks for taking back the word cuckold to mean dude who is gettng fucked over. Too much of the porn I watch tries to make ‘cuckold’ a new trendy term for dude who is willing to watch his chick get banged or be a swinger or some crap. I hate that. A cuckold never knows about it and thats why the term is so unflattering. Dont try to argue this (as the previous poster did) – its in Shakespeare for god’s sake.

    Nice job screwing this poor cuckold and showing him your dominance. Makes up for her unattractiveness.

    • PantyFairy

      You are so so wrong, I am an educated, Good Looking, Married Cuckold and yes I know and like my wife to screw other Good Looking, HUNG, preferably young Studs while I am there or when she does it without me and then tells me all about it when she returns. It is quite satisfying for both of us and has enhanced our sex life tremendously, but if you are insecure or a jealous type it is probably not for you. We love each other very much for 30 years now, but even though we share a great sex life this kinda fun takes it to limits we both enjoy!

  • Alma Federer

    You men gross me out. First, you glorify meaningless sex, and then you denigrate some woman who actually provided it to you. How can we women win? Either we provide you with sex and you call us cheap and can’t wait to get rid of us, or we get denigrated for not providing you sex! We can’t win!

    I therefore renew my call for all women to withhold sex for one week from any men who do not swear off bad habits and promise to be loyal to us.

    • Strenuous Objector

      You can’t win. That’s why men rule the world and women get kicked out of the apartment. You’ll never need to get kicked out though because no one would be slumming that low.

  • diminished capacity

    Why should I be laughing so hard at this? But I am, because the piece is funny even though it’s a little mean. I am a women, and man, you should thank your lucky charms you haven’t gotten poetic justice because you could have gotten the clap or something major instead of a watch your back for the rest of your life feeling. Instead you just end up in a stall feeling what it’s like to be a gal. So I say you go girl and go ahead try to make me laugh till I pee.

  • Bitter Overseas

    Yeah, I’m normally in on the adventures and sexcapades and whatnot, but you’ve been a malicious fool. Look at it this way: at least with him killing you, you’ll feel better about yourself (in some weird past tense kind of way) and so will the rest of the world

  • Karin

    Oh stop feeling sorry for yourself. You did what you did. Feeling embarrassed and a bit ashamed is his job. He’s the one who should be humiliated that his wife is our prowling behind his back. Maybe he’s inadequate and can’t please her. You should just suck it up and smile really big when you walk into the office or she’s going to be blackmailing you with it in no time attorney’s office or not.

    Be a man.

  • M&J

    OK now that is NOT cuckolding!! that is a just a cheating wife
    cuckolding is a 3 way deal WHERE all 3 are in the relationship!

    you should not use the word “cuckolding” for an excuse because suddenly you are feeling guilty for banging your co workers wife

    Maybe you should take the time to chat with her and enplane how you feel about what has happened