BUZZFEED: The recent Toast article “Literary Trysts It Gives Me Great Joy to Think About: Oscar Wilde and Walt Whitman” set off a flurry of Facebook shares and likes and a tempest of tweets and retweets. The idea of these two gay literary icons getting together truly was too delicious not to think about.
But Oscar and Uncle Walt were not the only gay writers — past and present — known for their activity between the sheets as well as between the covers. From various biographies, diaries, and memoirs, we know about poet Edna St. Vincent Millay’s intoxicating effect on her fellow female students at Vassar, author Michel Foucault’s penchant for S&M clubs, City of Night author John Rechy’s past as a hustling muscle daddy, and the dirt Edmund White dishes on himself in My Lives and City Boy.
Here are some of the gay past’s greatest writer-to-writer hookups — and a couple of Missed Connections.
Samuel Steward and Lord Alfred Douglas
Thanks to Justin Spring’s award-winning biography Secret Historian, we now know that in addition to being a professor, novelist, pioneering tattoo artist, and author of high-octane porn under the pseudonym Phil Andros, Samuel Steward was also a voracious sexual being. He kept a lifelong tally and voluminous notes on his activities, recording thousands of encounters with men (including for and with Dr. Alfred Kinsey — talk about doing it for science!).
On his first trip to Europe in 1937, Steward made a point of sleeping with Lord Alfred Douglas so that “through physical contact with Douglas he might establish physical contact, by extension, with his great literary hero Oscar Wilde.” The encounter itself was less than thrilling to the twentysomething Steward:
“Lord Alfred was by then sixty-seven, and in anyone’s book that’s old. To go to bed with him was hardly the most attractive prospect in the world — it was terrifying, even repulsive. But if I wanted to link myself to Oscar Wilde… there was no other way.”
Douglas had also become a Catholic and had given up his “homosexual leanings and entanglements…sins of the flesh were obnoxious and uninteresting.” Within an hour and a half after opening a bottle of gin, however:
“We were in bed, the Church renounced, conscience vanquished, inhibitions overcome, revulsion conquered, pledges and vows and British laws all forgotten. Head down, my lips where Oscar’s had been, I knew that I had won. … After I finished my ministrations and settled back, his hand stole down to clamp itself around me. It began to move gently. … ‘You really needn’t have gone to all that trouble, since this is almost all Oscar and I ever did with each other … We used to get boys for each other … We kissed a lot, but not much more.’
Allen Ginsberg and Jack Kerouac and Neal Cassady
Beat Poet Allen Ginsberg has the distinction of having slept with both the author of On the Road, Jack Kerouac, and its “muse,” Neal Cassady. Ginsberg “came out” to Kerouac in 1946, declaring, “You know I love you, and I want to sleep with you, and I really like men” one night as they shared a room together. Kerouac responded with, “Oh no…” then rolled over and went to sleep. Ginsberg was glad not to be completely rejected, and within a year he “blew him [Kerouac] a couple of times” and was on the receiving end of a drunken Kerouac BJ years later, but there was never any great sexual charge between them. Later, as Ginsberg became more open about his sexuality and Kerouac would complain about what “his public” would think about him, Ginsberg had to remind Kerouac of the times he’d drunkenly challenged Ginsberg with phrases like “C’mon, I’ll fuck you.”
Ginsberg had more success with Neal Cassady, who claimed to need sex every day to live — no matter where he got it. Ginsberg shared a “weekend of debauchery” with Cassady in early 1947 a few days after Cassady had had a fight with his wife. Cassady then disappeared for two days, leaving Ginsberg filled with self-pity. They would see each other intermittently until Cassady’s departure from New York in March of that year. Horny and insecure during the breaks between seeing him, Ginsberg would list all the possible combinations of sexual positions he wanted to try when they got together again:
“Try him laying me again, try breast to breast position, try 69 again coming both at once, try sitting on his chest and making him blow me, try laying his mouth, French kissing, etc., make him give me a trip around the world….Have I guts? Trip around the world, complete, winding up with blow job. No, I want some real hip sex, what is it?”
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