I want to have s** with my boss lady

I'm in my 60's, grew up in the 60's and 70's where discussing s** wasn't something people did openly. P*** magazines were hidden and if you approached a woman for s** you were shamed. That was my world. I'm just a normal but h**** man and act like a gentleman around everyone. Now I work at a place part time. My boss is a lady in her 40's, not an attractive woman but is attractive to me. She is a short chubby, not fat, lady. I'm afraid to bring up the subject of wanting to f*** her. She sees me peeking at her t*** when I talk to her and even covers her chest with a jacket that she wears when I come to her office. She's very open about talking to me about life but with all of this Human Resources sexual harassment bullshit I'm afraid to approach her about the things I would like to do to her, or with her. She is married with 4 kids. I'm a married man but the wife and I don't have s**. She's just not interested in it anymore. I don't want to raise red flags at the company and embarrass myself. Any suggestions or advise from anyone who has the same thing happened to them?

Mar 10

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  • See an escort. It's cheaper and less emotionally draining.

  • I used to have lots of s** with my first boss lady.
    I was 22 single & at my first job out of college.
    Traci was 48 divorced, redhead, 4' 10, no t***, maybe 100lb with a crazy fit body and firm a$$ that would stop traffic! First impression was she’s a b**** but we got along. She just did’t care for inefficient people. lol
    She caught me checking her ass out one day and gave me a wink. After that, we started flirting when no one was around.
    There was a bad storm that knocked trees down on her street and her neighbor called to tell her it was a mess and they had no power. Traci planned on finding a hotel for the night.
    I was serious but said it in a joking way, “Don’t waste your money on a hotel. You can stay with me.” I’ll never forget the look in her green eyes when she said, “Are you serious?” I said yes.
    She said, “I need to buy some pjs and I promise not to be a bother and I’ll sleep on the couch.” I took a chance and said, “Why do that? You'd look good wearing my shirt and I was hoping we could share the bed together.” Well, that worked and after a long night of crazy s**, we secretly started seeing each other until she got a promotion and had to transfer to FL.
    We tried the long distance thing for a few months but it didn’t work out.
    She was a crazy wild redhead in bed!

  • Have you communicated with your wife to learn why she is no longer interested and told her how her lack of interest makes you feel? Could it be that may be you both aren't speaking each other's love languages? Have you considered counseling first vs the ideation of cheating? Unless of course you feel you no longer love your wife anymore...

  • Open up and discuss about your asexual life due to wife, show your frustration, wait for her reaction and move ahead accordingly.

  • Do not approach your boss for s**!

  • If she specifically covers up when you approach her then she's probably not interested.

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