I used to be on Craigslist like crazy and had all sorts of crazy hookups.
I had an amazing first date with this sexy older milf twice my age who loved having a younger mans attention and thne I fucked her sideways.
I once " Got lost" on the way to a sex party and ended up fucking a girl at a hotel we stopped at on the way when maybe finding the club wasn't as interesting as tearing eachothers clothes off was.
I had one hookup who would sneak me into her parents house toblow me and I had to hide on the side of the bed as she carried a conversation with her dad.
I went out with this sexy crazy gamer chick ( showed up to the date wearing cat ears years before that was cool for e-girls) who was obsessed with me and would basically beg me to fuck her hoping I'd nut hard enough to make her my girlfriend (would have worked if she was less intense)
I had a hookup who would stop by my place because she had a creampie kink and would just come by to have me fill her pussy up .
I used to fuck a nurse who would come over to my place after intense shifts to destress her
I was on-call for a while for this sexy latina stoner chick who also had a creampie kink and would call me over so that she could ride me until i nutted deep in her super messy place.
I had a fun very brief summer fling with this super cute 21 year old who was in my state for a visit and just wanted to find a guy to have some fun with .
I got plenty more but those are some of the hotter ones I can think of