Have you ever been asked to sleep with a friend's son or daughter?

My business partner, Lily, is a 50-year-old widow. I consider her one of my best friends and we get along perfectly. Her husband died of a heart attack when her daughter was 12, and she hasn’t had any room for men in her life since then.

I’m 36 and single, I was a competitive athlete through my teen years and early 20s until I got lazy and became a workaholic. So I could lose a few pounds but women are receptive when I flirt with them.

So last year, Lily’s only daughter Alyssa graduates from college moves in with her fiance and catches him in bed with another girl - another girl he was engaged to at the same time. She was devastated, trashed his place, quit her job, and moved back home. It was August when Lily spoke to me about how Alyssa was really a shadow of her former self and just not adjusting to life after the breakup. She was concerned about her drinking too much and losing her ambition, so when Lily was going away for a “girl’s weekend” to Vegas, she asked if I could spend some time with Alyssa - maybe take her out for dinner and get her out of the house. I thought nothing of it and agreed.

I picked up Alyssa on Saturday evening and we went out for dinner - sushi and martinis - and we had a great time. Even at 22 she looks like a teenager and was asked for ID at the bar and again by our server. It made her blush - she finds it flattering rather than annoying. So after dinner we took a walk around downtown, and she put her arm around me out of habit. I’d known this girl for 6 years, but hadn’t really seen her since she went away to college. She was a lot like her mother - feisty and independent and outspoken - but she was still hurt and found herself thinking about what she did wrong in her relationship. I assured her that it wasn’t her, but her ex, and that it’s possible to do nothing wrong, and still end up on the losing side. She hugged me tighter over that.

I brought her home and she offered me coffee - telling me that she too was aware that she was drinking too much to forget her ex. So I went in to the house with her - she slipped off her sandals and seemed to glide over the floor in her sundress. I was now starting to get excited over how good she looked. She made coffee with the K-cup machine and on her first sip, she spilled some down onto her cleavage. I laughed and blushed, but she kept her eyes on mine, and pulled the straps off her sundress - she wasn’t wearing a bra. I couldn’t resist - I leaned in, kissed her, and took her upstairs where we had sex - bareback - several times before falling asleep around 3am. In the morning we had one more round before she invited me to shower with her, which got me excited and we attempted another round before I gave up, drained.

She thanked me for a lovely night and I went home. Lily didn’t return from her trip until Monday and came to work on Tuesday morning. She grabbed a coffee, walked into my office, and casually asked me “So how was my daughter?”

I didn’t know what to say and feared the worst, but Lily wasn’t the least bit angry. This was her desired outcome - she wanted Alyssa to feel wanted and sexy, because she was still beating herself up over why her fiance had cheated on her. Alyssa was petite and blonde and very sexy, but her fiance had cheated on her with a tall, dark-haired, voluptuous woman who looked her age and seemed more “exotic”. And she knew that I wouldn’t be able to resist - Alyssa turn’s heads for men and women alike - and I didn’t. Lily then closed the door and we had a very frank discussion about this - she and Alyssa have no secrets and have been a tight duo since her father died. Lily encouraged me to keep spending time with Alyssa - and if we wanted to, having sex, but that she wanted me to be careful with her daughter’s feelings.

The next weekend, Alyssa and I met for dinner again, becoming more comfortable with each other, and at the end of the evening, I asked her to come to my place, since I wasn’t quite comfortable with having sex with her in her mother’s house. And so she did. We have been “friends with benefits” ever since. Alyssa got her act together. She joined a gym, got a job, and found a place of her own in January, though not before I got to spend the night with her with Lily in the next room. We even went away for a weekend - all with her mother’s blessing.

Lily does not shy away from telling me that her daughter regards me as an A+ lover, unfortunately knowing my deepest secrets. This mother and daughter share no secrets - I find that a bit weird - but it’s been a good year and I think I am falling in love with her.