Whisper: I Caught My Boss with His Pants Down

*As told to Kally from someone who wishes to be anonymous

I have been in this law firm since the very beginning and enjoyed my time working for one of the partners as a paralegal for 13 years. When he retired, his son took over his position and inherited me as his paralegal as well. Although it is a small firm, business is flourishing and we have plenty of regular clients that keep us on our feet. Bosses are generous with our salary increments and bonuses. All of us are like family and we are pretty close knitted.

My boss, James, the youngest son of the previous partner, is a friendly no-nonsense kind of guy. He is attractive mid-thirties family man with an equally attractive wife and three children. I enjoyed working with him and he pulled in as much weight around the office as the older partners do. As we are getting more cases, it is not surprising to see the lawyers working overtime and overdrive with their paralegals late into the nights and sometimes over the weekends as well but I was well compensated for both my time and effort.


One late summer last year, my son had measles and I had to miss work for a week. James was very generous about my absence and even transfer another paralegal from another section to cover my duties. Recovering from measles, my son developed complications that led to him having a prolonged fever and delayed recovery. With worries about my son at the back of my mind and inability to contribute extra hours after work, I struggled with my daily tasks and my work just kept piling up. James kept the covering paralegal, Elaine on to help me clear up some of my backlogs. Elaine is the sort of girl you’ll like on first sight. She is like the next door girl with a clean wholesome look and there’s just something about her that makes you trust your deepest secrets with. She is smart, bubbly and hardworking.

Rumours begin to start around this time that James is having an affair. I suspected that the rumours have spread to his wife’s ears as I bumped into her thrice in a month, “casually dropping by” the office to see James. It has never happened before. Colleagues started to ask me if I heard or know anything but I didn’t.

One night, I remembered I left my iPhone at my work desk, only after I reached home. Instead of going straight back to the office to retrieve it, I decided to have dinner with my son and putting him to bed before heading out to the office. That way, I reasoned, I might put in an extra two hours in filing some of the court documents tonight.

As it is, I reached my firm around 10 pm and I saw from afar that James’ office lights are still on. Recalling that James had left early for a dinner appointment, I figured that he probably forgot to switch the lights off. I barged into his office without thinking and there, basking in half naked glory are James and Elaine on the carpet. I totally blanked out. I remembered murmuring a half-hearted apology and rushed straight to the lift without looking back. I even forgot to take my iPhone with me. Again.


I was back into the office the next day and so was James and Elaine. I couldn’t look at both of them in the eye. It was business as usual and neither of them shows any discomfort or indication that something unusual happened last night. It was as if I dreamt up that incident!

It became obvious that both of them are having an affair as I started to notice all the signs like how they timed their lunch breaks to coincide and how they always stayed back after work. Elaine even started to doll herself up and dressed in sexier blouses and shorter skirts. On some personal level, I was uncomfortable working with both of them, knowing that James is cheating on his wife. I admit it is none of my business and I shouldn’t judge on their private lives. In the end, I was offered to transfer to another branch office nearer to my home and I took it.

Every now and then, I’ll bump into James whenever he comes over to my branch for the monthly partners meeting. It will always be a nod and a smile but nothing more. The image of his naked butt will forever be stuck in my mind.

*As told to Kally from someone who wishes to be anonymous

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13 Comments Add yours

  1. The V Pub says:

    How embarrassing!!

    Liked by 2 people

  2. Paul says:

    I was a single male during my ten year tenure as chair of a university English Department. I had sixteen faculty in my department and one secretary. I remember walking in on the Dean–it was after hours–and sitting on his desk was a dream of a girl. She was down to the third button on her blouse. She turned to me and said, “hi.” as if nothing were amiss. She laughed, waved to the Dean, who looked as if he had just swallowed a cyanide pill, and walked out. Her unbuttoned blouse wide open revealing what any man would honestly say were a pair of lovely young breasts. I think by the time she got to the outer door, she had gotten the blouse buttoned. The Dean tried to shake it off, but well, it was just too damned much.

    We talked and he told me “that sort of thing happens a lot.” I asked him what did he do on those occasions. He flipped the question. “What would you do?” My instant response was: “Stop her.” I mean we’re talking about a young lady, maybe twenty-two, from another office somewhere in the building. He just shrugged. He told me I was naive. A few years later he was gone.

    Getting “close” to office workers happens, I think, naturally. I recall my secretary. She knew everything that was going on. We talked. We traveled together. She was married, had two kids. I even baby-sat the youngest one in the office on Fridays. He was a good kid. We never moved past our working relationship, but I think we both knew how close we had gotten. She’d call me on the phone when she was upset with her mother. I went to her parties. She was African American. I was white, so I’d be the only white guy at the party, but I knew most everybody and we all liked each other and drank Crown Royal. I knew her husband. We didn’t see each other so much. He was a truck driver, but when we were together we talked and laughed. My point being, lines slowly become blurred. My secretary and I were so comfortable with each other. I remember talking with a co-chair, who confided in me after he had fired his secretary. He said, “your secretary is your second wife.” I never forgot that. It’s simply impossible in many cases in the professional arena not to get very close to a co-worker. And I think you can stretch and/or blur the line but it’s still a line, and if you cross it…well, it’s never good.

    Great post.

    Liked by 1 person

    1. Kally says:

      Thank you for sharing your thoughts and your story. Yes, I do agree sometimes it is hard to differentiate the blurred lines especially when temptation are involved.

      Liked by 1 person

  3. Oh gosh. May all be blessed with love and Light. Kally thank you for a caring and honest post. Blessings, Debbie

    Liked by 1 person

    1. Kally says:

      Thank you Debbie for reading it! 😊

      Liked by 1 person

  4. Denny Sinnoh says:

    Maybe he just had an itch.


    I actually have a funny story about how I was once changing from work pants to gym shorts in my office and a maintenance man walked right by my window when I had my pants down.

    I was on the 5th story of a building. The window only looked out to an asphalt roof. I should have turned my blinds but I figured, there is no one who would walk by on the small asphalt area just outside my office. I have never seen anyone out there before.

    You guessed it. Janitor walked right by when I had my pants down.

    Now two-weeks later I was changing again. Should I go turn those blinds? I though. I mean — what are the CHANCES? So I did not turn the blinds. Guess what happened. yup maintenance guy caught be pulling my pants down at the exact moment he moved past the window.

    True story. Please share this story with Mabel Kwong.

    Liked by 1 person

    1. Kally says:

      Hahaha. Thanks for sharing the funny story, Denny. Must be embarrassing for you to be caught in such situation. I’ll be red in the face if it’s were me.

      Liked by 1 person

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