I'm a more mature (I prefer the term mature to older) guy and I find it difficult to find mature guys (on dating sites) who want to date/hook up with other mature guys. I find a great majority want much younger guys.
Had a friend who was unable to remove a metal cockring and ended up at the ER with FIREMEN (!) having to cut it off with a saw. Sounds hot but he was in great pain and was, needless to say, overwhelmed with embarrassment.