Yes many times

My girlfriend (24yrs old) arranged her first gangbang. She's into older men (3yrs our age gap). We were 5 participants, me, her ex boss (48yrs old), her ex professor (51yrs old), her co-worker (39yrs old) and my cousin (44yrs old).

I have watched my ex girlfriend with her best friend.

Fuckin my beautiful and sexy single mom friend and her mom and sister.

8yrs. I'm 25 and she's 17yrs old.

Yes and yes. The first time was with my ex girlfriend and a security guard who caught us fucking in a public place. It was a wonderful experience.

When I became single, I got attracted to older women. Ever since then I had sex with a lot of older women. My oldest hook-up was 64yrs old.