Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right Virgin territory

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

More to explore