Virgin territory

As part of Time Out Chicago’s annual Sex issue, we asked members of our LGBT community to share the story behind their first same-gender romp.

“My first time was with a guy five years older and much more experienced. It started with cinnamon lube, which I wasn’t prepared for, involved a paddle and ended with his grandmother walking in while I was handcuffed to his bed.”—Jason Steele, RedEye columnist

“When I was 14, a really beautiful 16-year-old cheerleader moved in the house next door. She was smart, outgoing and liked to do splits. One night at a summer wedding reception, we snuck away to the Belmont Rocks with a half bottle of Champagne. After a lot of ‘giggling,’ we returned two hours later with grass-stained dresses minus one of her shoes and my bra. Luckily, everyone had gone by then and we got to drive home with our dignity intact.”—Jenae Williams, nightlife impresario

“The first time I ever had sex with another trans guy, I was 22. This cute boy from Colorado was staying in Logan Square for the summer. The whole evening is a little fuzzy, but dancing at Berlin was definitely a feature. I believe the words ‘secretly, I’m kind of a bottom’ were uttered, to be met with his ‘secretly, I’m really a top.’ There was some tussling and hair pulling, which, when at a public place, generally signals it’s time to go home. To be in bed with someone with similar ideas about his body, similar words for similar parts, similar gender roles and similar wants…totally awesome.”—Simon Strikeback, musician (Actor Slash Model) and filmmaker (Riot Acts, screening at Reeling Film Festival on November 6)

“It was about five Mike’s Hard Lemonades into the evening…ironically, in my girlfriend’s closet, with her best guy friend. She still doesn’t know this. Hopefully she’s not a Time Out reader.”—Scott Cramer, nightlife impresario

“What first time? I’m still waiting for marriage.”—Bill Pritchard, senior vice president of community affairs for ChicagoPride.com

“I remember my hair was in braids, and I went over to her house in my satin pj’s and brought along some hot chocolate, but once the door to her bedroom closed, my memory got cut off. Seriously. When I try to think about what was a phenomenally important and wonderful moment in my life, I just see a door closing in my face.”—Searah Deysach, owner, Early to Bed

“My first time will be about a year from now. I am raising money for sexual-reassignment surgery. Oh, yes, I will be a virgin once again.”—Honey West, cabaret entertainer

“At the first March for Equality, I met this hunky deaf redhead from Beaumont, Texas, who couldn’t hear me very well, but, boy, could he read lips! Like most young gay men after getting their first blow job, I fell in love. He was a deaf dreamboat.”—Fausto Fernós, Feast of Fun podcaster

“My first time was all about who is the top and who is the bottom. That took five minutes.”—Miss Foozie, drag hostess and entertainer

“All I can say is it involved a Brazilian monastery and a festival for Saint Francisco—the protector of ‘natural’ surroundings. Study abroad ’99 was a spiritual experience.”—Khyentse James, founder, Decibelle Music and Culture Festival happening Thursday 15–Sunday 18

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