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 after I turned 40 myself, I was cruised by so many twinks that the older guys were sort of left out of the equation.
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.
5.
And a professor of political science from Egypt who said "You got what you wanted, now give me what I want." About 25 years.
Texas
6.
My most embarrassing hookup, a guy I picked up in a bar who thought I was a hustler. About 20 years
West Hollywood
7.
In 1987, when Alan moved to Thailand, I moved in with Derek, a former fitness model turned realtor. We were housemates for a long time, and occasionally shared boyfriends. 21 years.
8.
Meanwhile my on-off boyfriend Raul moved in with Heinz, a crazy German senior citizen who was into drag queens, watched the Miss America pageant, and sang "Come away wiz me tu Malibuu" all the time. Really annoying. So why did we hook up? It was late, I was tired, Raul offered. 35 years.
9.
Jasper was a preacher at a Baptist church in Gardena, not out to his congregation ("but I'm working on it"). He believed that the Bible prohibited anal sex, but not oral, so we were free to engage in all the oral we wanted. One date was enough. About 20 years.
10.
Oscar, the retired set designer from Des Moines who claimed to be the ex-lover of President Ronald Reagan. He came to visit me in West Hollywood. I tried every way I could think of to get rid of him, including offering to help him reconnect with his old lover, Ronnie. 46 years!
11.
After I started dating Lee, he introduced me to a whole coterie of older guys, including Randall, who lived in Long Beach and had pierced nipples and a pierced penis. 23 years.
San Francisco
12.
Karol, the Polish artist who had been living on Castro Street since the 1960s, who cruised my friend David every day and finally "whipped it out." OK, he was David's hookup, but still memorable. 31 years.
New York
13.
Kalle, the Swedish bodybuilder with the face like a serial killer that Yuri met in a bath house in Estonia and insisted we share. About 20 years.
14.
At a bath house in Montreal, I met James, an older guy with a nondescript physique who invited me to share his friend -- a muscle god. Why was he acting as a wing man? About 30 years.
15.
Ravi, an older South Asian guy had a house in Brooklyn and held M4M Parties. His partner was much younger and didn't do anything with anyone. The parties ended when the partner died. About 20 years.
Florida
16.
Barney, an ex-bodybuilder who ran a gym. My housemate for four years. We sometimes shared. 19 years.
17.
Gerry, the Georgia boy who had come out 2 years ago at age 65. Once his hookup lived too far away to meet, so he asked to meet halfway, at my house. I agreed, but only if I got to "share." 25 years.
Upstate
18.
The Satyr, one of the Gang of Twelve who had known each other forever and dated each other on and off. He was a name-dropper: he had dated John Travolta, Tom Cruise, Quentin Crisp, and everyone in between. He had an enormous Kovbasa+ and used it to his advantage. 16 years.
Plains
19.
When Yuri visited me recently, I figured that he was still into older guys, and tried to fix him up with Mike, a retired professor of education. 15 years.
20.
My Last Daddy (to date), who comes to the M4M Parties. Upper 70s, built, body by Michelangelo. I hope that I will look that good in 25 years, at age 79!
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