There’s a first time for everything

Slide show photographs by Stephanie Gladney

My first time…

having sex in a bathhouse

in a threesome

I cheated on my spouse

having sex in public

using a glory hole

PLUS:

Week in the life of a sexpert
It’s a tough job, but someone has to do it. Time Out Chicago‘s sex columnist does more than answer your sex queries. She thinks sex full-time.

Sexcerpts
Some helpful highlights from TOC sex columnist Debby Herbenick’s new book, Because It Feels Good.

Summer of love?
Our singles report back on their flings, or lack thereof. Plus, two new singles.

Sexy lingerie
Steam up the bedroom with a new set of briefs and bras.

How sexy are your sheets?
Your bedding can give your one-night-stand insight to who you are.

Chicago’s sexiest hotels
Spend the night in one of these five sexy hotel rooms.

Hugh Hefner
For our Sex Issue, who but Hef?

Freakonomics
Remember when your big sister and her friends would take those sex quizzes in Vogue and kick you out of the room? Well, you’re a big kid now, so you can take your own—trouble is, you’re reading Time Out Chicago. Take our sex quiz to see how freak you really are.