This goes way back... 22 and living in Chicago. I was inexperienced sexually. Was at a sports bar with a mate watching game when an attractive MILF started chatting... Slowly her hands were on my thigh and flirting... She kissed me all of a sudden, pulled me and started kissing... smiled and asked if I liked it... of course I did, she was HOT and very attractive. It was my first time in a bar, milf etc etc and was shy but excited feeling lucky... 15 mins later a guy holding her drink shows up. They whisper as he sit down... I face away not wanting any trouble. But she kept taking and touching, And wanting to kiss me again, when I moved away saying don't want any trouble. She still kissed saying it's OK. After the drink she said they are leaving asking me to come as well. With my friend egging me on to go. We left and she said will ride in my car. Dropped my friend at his place near by. She asked me to park my car the and come in their car. They parked the car some distance away and told me to come sit in front seat. She sat on my legs kissing and undoing my jeans and went down on me. I was shy and bit scared with one eye on the guy... She then sat on my dick and started riding... The guy kept looking at us with out any reaction... slowly I got comfortable too. She rode me till I came... they then took me to their house... Couple of more rounds and left in the morning... The guy just coming into bedroom watching...

I met her regularly for a year. The guy it turns out was her husband, I told her it was first for me, first time being picked up like this in a pub first time with a milf , she was in her 50s, first time in front of someone's partner, and many more first were to come as we met more... Those for another time... I still can't get it out of my mind...