Guys who are over 40 (called Bears or Daddies, depending on their shape) have a lot to offer. They are comfortable in the gay community, not newly out and scared. They have cars, swimming pools, theater tickets, all the material possessions that turn a date from mediocre to spectacular. And they know their way around a bedroom.But when I lived in West Hollywood, it was against social norms to be seen with anyone more than about 5 years older or younger. And since I turned 40 myself, I've been approached by so many twinks that I tend to ignore
But still, I've had some memorable boyfriends and hookups who were 20+ years older than me.
Augustana College
1. Dr. Burton, who taught palaeontology at Augustana and held regular "handcuff parties" for his advanced students. We became "friends with benefits," though I didn't interpret it that way at the time. 23 years.
Indiana University
2. During my first year at Indiana University, I visited a Metropolitan Community Church in Kentucky, and afterwards went out with the minister, Brother Reid, and his boyfriend Terence. While spending the night in the guest room, I wanted to hook up with Terence, but got Brother Reid instead. About 25 years.
3. One night at Bullwinkle's I was offered a drink by a distinguished older man who turned out to be rather wealthy. He took me back to his house, where we sat in a gold-and-white drawing room next to a grand piano, and he called his lover to brag about his luck in picking me up. He said "At this stage of the game, we're mostly business partners anyway." 34 years.
4. Also at Bullwinkle's, I met a Nigerian guy who had hundreds of books on witchcraft and a tattooed penis. About 20 years.
The full list, with uncensored photos, is on Tales of West Hollywood