I've had a couple relationships with women much older. First when I was younger (18/19) with very sexy lady in her 40s. It started out as a friendship and turned into more. I think it definitely was a great experience because most of my sexual relationships had been, or at least started out, a little awkward where with here it was just like very fun and low stress and even to this day, never ruined our friendship.

It was great but I still only mostly went for women my age until recently when I moved to Florida. I work a lot and do a lot of odd jobs in my spare time and had been helping out one neighbor. I don't know her exact age because she looks great but she has to be in her early 60s I'd imagine as she is retired. I did a lot of small stuff for her around the house and yard and we were pretty close. Well, eventually we hooked up but it wasn't full on sexual at first, and even when it did become sexual, we still maintained the same relationship.

I've done FWB with girls my age and it just always gets weird, like jealousy kicks in or its not possible to maintain the friendship aspect. I mean I'm a young dude so yeah I like getting in, but tbt if there is nothing else there sometimes It makes more sense to just jack off haha. But with mature women it's different

So now that I'm pretty fully committed to "cougar hunting" I was just looking for other anecdotes, or advice or anything really.