I don't really have an age preference, but it seems that when I was in my 20s and 30s, I usually ended up with guys 5-10 years older, and when I hit 40, guys 10 or more years younger. I'm over 50 now, but I still get cruised by practically every twink I meet, even those who say "no older guys" on their profiles.
Dating younger guys has some advantages: they're cute, they have boundless energy and enthusiasm, and they are constantly surprised by your stories of life in the 1980s.
But there are disadvantages: they go out too often and stay up too late, they don't fit in with your friends, and even after extensive research, you still can't understand their pop culture references.
Here are my favorite teenage (or twink) boyfriends and hookups who were 10+ years younger than me. Don't worry, they were all over 18.
New York
1.
Conrad,
the 20 year old who came to my room Upstate to fix my computer, said "I'm not into older guys," and grabbed. 17 years.
2.
Mario,
a teenage model studying at Columbia University. We went on one execrable date. 20 years.
3.
Sibu,
the hottest guy in the world, a seminary student met at a conference in South Africa. Dark room hookup, and then "I'm not into older guys." 15 years
4.
Liam,
who I talked to online for several years. He waited until the exact moment he turned 18 to give me a birthday present. 21 years
5.
Jermaine,
the Biggest Guy on My Sausage List. A Harvard undergrad studying political science, and planning to go to law school, we met when I was on a job interview in Boston. 18 years.
6.
The Pizza Boy, an undergrad theater major in Rock Island. My friend Dick actually started dating him, but we shared at Christmastime. 18 years
Florida
7.
Victor,
the Brazilian twink who turned out to be a drag queen, Miss Chita Taboo. 16 years.
8.
The Young Republican,
one of my ex-students who invited me to a Christmas party at his parents' country club. We dated a few times in spite of his politics. 20 years.
9.
The college freshman hitchhiking to Key West who David and I picked up. 20 years
10.
Jean in Paris,
the violist who wouldn't let me touch his instrument. 22 years
11.
The high school bodybuilder.
We dated a few times. I also may have hooked up with a couple of his friends, but don't worry, I made sure they were over 18, too. 26 years.
Dayton
12.
Paul,
the aspiring writer. Boyfriend for about six months, lived with briefly, but he turned out to be too good in bed. 22 years.
13.
The Emo boy who I picked up in London while visiting Yuri and Michael. 26 years.
14.
Austin,
the high school boy who hit on me in the park. Of course, nothing happened, but I'm proud of the way I handled the situation by introducing him to other gay kids. 32 years
Upstate
15.
Chad,
the Satyr's houseboy/boy toy, who worked as a waiter at the Neptune. We dated through the fall and winter. 21 years.
16.
Malik:
picked up by the boy and his dog. 23 years.
17.
Troy,
a 23-year old French major when we started dating. We were together for about five years. 26 years.
18.
Peter,
who rejected me at the bath house the night I became a Creepy Old Guy. He came around later. 28 years.
The Prairie
19.
Andy,
The boy with daddy issues who wanted to rip my clothes off, who I met at a comic book store. Two dates. 30 years.
20.
Scott,
the youngest guy I've ever dated, a 22-year old theater major who wanted to try everything. 32 years
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