I was 21 and had a 59 yo lady wear me out. She didn't things to me that I had only read about. Left me drained for the next 36 hours.
In college I hooked up with a divorced MILF at a hotel nightclub/bar. I was 23 and she was 45. She was a lot of fun at her place: kitchen, couch, bed, shower, and then bed again in the morning.
A few years ago I hooked up with a younger woman via craigslist. I was 60 and she was 39. We met Saturday afternoon and she didn't leave until Monday afternoon. We became FWB and would hookup about every 2 weeks. After about 7 fun weekends she wanted to "date like normal people." i told her, "You answered a FWB post. You knew what this was from day one."
Escort: I was 61 and she was 32. I had no idea she was that young. We were at a party of about 30 escorts and 25 men. We met at a dining table as several of us ate dinner. We flirted, we danced, etc. Next thing I know we're naked in her hotel room, lol.
35 year difference for me, I was 19/20 she was 55. Itwas actually a friends mom I was renting a room from. Her husband was a nice guy, he was a chef at an all girls college. He let himself go and got up to well over 400lbs. She was a hot milf and petite I’d find myself hanging around on weekends watching her clean the house. We were flirty for a while and thought it would end there. I asked her for some advice about a girl I was seeing, and one thing led to another and she was showing me rather than telling me. That was the start of the affair and it went on for a year. I’d come home from a club after closing and her husband was getting ready to leave to go to cook breakfast at the college and I’d slide into his bed with her. I ended up getting caught by my buddy one morning while slipping out of her room, that was awkward and very uncomfortable but him and I worked it out. He knew his parents weren’t intimate anymore with how big his dad had gotten. Anyway, she was an amazing woman that showed me how to be the best lover I could be. Every. Youngster should get an education like that. A few years ago we linked up on social media and are friends, she is quite old now, but so am I to, but she’ll always hold a special place in my heart for what we had for that moment in time a long time ago.