Time Out Chicago / Issue 138 : Oct 18–24, 2007
The Sex Issue
Virgin territory
Chicagoans who’ve made it big tell us about the first time they made it.
By Jason A. Heidemann
“I was 15. The dude was 14 and way more experienced—but let the record show I was no slouch. He was a budding juvie and looked like Steve Perry from Journey. He could spit fire like Gene Simmons using a butane lighter. We were sharing a tent on a camping trip and made out and fell asleep, but then it rained really hard and it woke us up and we got it on.”
—Kelly Hogan, singer-songwriter
Photo: Maia harms
“My first time was supposed to be a carefully crafted evening that would climax at whatever the hotel that is now the W on Lake Shore Drive was called. Way too expensive dinner, drinks and then up to the room, where, in my enthusiasm, I got the worst case of rug burn
ever. To this day, every time I drive by the W, I look up and I think of that smoke-stenched room and my then-bloodied knees.”
—Dean Richards, WGN entertainment reporter and critic 
Photo: Sarah Bank
“Back in the ’60s…I decided that I’d let the Rolling Stones’ Brian Jones be my first lover. That is, if I could ever get him alone. While I was dreaming of the day this would happen, I met Mark Lindsay, the lead singer of Paul Revere and the Raiders. His drop-dead good looks, accessibility and top-of-the charts status made me forget all about Brian. Early the next morning, I became a charter member of the Sexual Revolution—with an A- in Groupie 101!”
—Cynthia Plaster Caster, recovering groupie, plaster penis and breast sculptor 
Photo: Sarah Bank
“She and I stripped, covered ourselves with talcum powder, and went bareback riding on a water-smooth silver stallion under the smiling Norwegian moon. We found bliss beside an ancient fjord where the Vikings sailed their dragon ships. Oh, what a night it was!”
—Roger Ebert, film critic “It was the summer of 1984 and I was living in Willowick, Ohio (home of the black concert T-shirt, faded jeans and feathered bangs). I had this ’65 metal-flake blue Ford Mustang. Lisa, a superhot junior (think Phoebe Cates) who lived on my block, asked me to take her into the city (Cleveland) to buy a dime bag. On our way back we pulled over at Euclid Beach to smoke a joint. With ‘Caribbean Queen’ by Billy Ocean playing on the radio, I made my move. To my surprise she didn’t resist my advances so I kept on marching. By the time I got to home plate I was swooning in ecstasy. When it was over I remember saying, ‘I am sorry.’ ”
—Rodney Alex, owner of Juicy Wine Company 
Photo: Maia Harms
“I was 17 and had just gone to my boyfriend Mark [insert Jewish last name here]’s prom. I was thoroughly unprepared for him being awkward and coked-out during my initiation into adulthood. So we went to a pool party afterward and I haughtily asked, ‘What if you just got me pregnant?’ Then, I gracefully dove into the pool and wouldn’t speak to him for the rest of the evening. It was so much fun that I didn’t fuck anyone for a long, long time.”
—Susan Messing, actress, iO instructor, founder of Annoyance Theatre
