I (33f) have always had a close professional and personal relationship with my boss, Willy (52m) He hired me 8 years ago, before I even met my husband, who I have now been married to for 5 years. One night after work, a bunch of us went to happy hour and Willy and I ended up being the last two people there. We were hanging out and having fun at the bar just talking about random things when I brought up Willy's dating life. This led to Willy admitting to me that he hasn't had much time to focus on dating because work takes up so much of his time. He went on to say he was mostly just looking for intimacy and not a relationship and that he was even looking into paying for it. Then Willy jokingly propositioned me to be his sugar baby, but I just laughed it off and reminded him I have a Job and a husband.

Later that night when I got home, I got a text from Willy apologizing for being inappropriate earlier. I replied that it was fine and I totally understand the situation he was in and that maybe it would be different if I was single. Willie responded "well maybe your husband would be interested in the money? I'll give you $2500 for one night if you change your mind." I was shocked at the amount of money. Just then my husband walked in and asked who I was texting....

To speed this story up... I told my husband about my conversation and offer from Willy. To my surprise, my husband told me that if I wanted to do that and give him some of the money, he was ok with it! I thought about it for a few days... I definitely was not attracted to Willy, who was 20 years older than me. Other than the age, he wasn't horrible looking. He is black, tall, in good shape, and has a nice smile. Ultimately, it was the money that made up my mind and I let Willy know that I would accept his offer if he was serious. So we made plans for that weekend....