In this week’s entertaining-as-hell Sex Issue, Chicagoans spill about first times—from hooking up via Craigslist to using a glory hole. Now we want to know about one of your firsts: the very first time. Don’t hold back those juicy or awkward details; that’s why we have a comments section.

Photo: Sean Williams

Our cover shoot for this week’s issue was quite the production—as you can see. After several traditional modeling agencies turned us down due to the racy subject matter (sex, oh my!), we turned to local performance artist Lady Jack, a.k.a. Lindsey Marks, to be our cover model. She did a beautiful job—and modeling for photos isn’t even her main talent. Lady Jack performs and produces burlesque in Chicago and you can catch her in the act (dancing that is, not in a scandalous back-of-a-cab liaison) in The Wild Party Variety Hour, presented by Silent Theatre Company. The Mary-Arrchie Theatre, 735 W Sheridan Rd, Oct 24 at 10:30pm. Admission is $10.

Before I spoke with Hugh Hefner for this week’s Sex Issue, I mentioned the interview to a friend, a longtime Playboy reader. He said he’s always thought that Hefner in interview mode comes across as somewhat blithely unassailable: I’m Hugh Hefner—you know, the luckiest bastard alive.

Which, as it turned out, was pretty much his answer to the first question in our Q&A.

But that was just one impression I had of Hefner when he called from the Playboy Mansion—and, frankly, it’s one he seems to cultivate. As indicated by the following excerpt (not in the published interview), Hefner’s keenly aware of the link between his persona and his product. Read more »

Back in July, we once again stepped into the matchmaker role for some lucky readers looking to score a last-minute summer fling. They filled out a ridiculous questionnaire (but really, no more ridiculous than Salon or Chemistry), we took their photos and the results appeared in our July 30 issue.
What happened next? Were they only contacted by weirdos? Did they have that summer fling they’d hoped for? Did no one contact them at all? We wanted to know, and we figured you did, too. So we asked them to spill it. Check out all the dirty details. Plus, peep two new singles hoping for a little Time Out hookup.

I doubt this was the kind of ring Beyonce was singing about. My Single Ring, a sterling-silver ring featuring the interlocked male and female symbols (if you’re straight) or same-sex symbols (that’s right, if you’re gay), proclaims to the world that you have no attachments and no one to nag about picking up milk on the way home from work. It’s a wedding ring—for single people!

The masterminds behind this new bling, Chicagoans Tim Gould and Scott Gilbert, say it’s “a ring design developed for the single community to identify themselves the way a wedding band identifies someone as being married.” Okay, guys, seriously, I don’t want to hate on some hometown entrepreneurs who are just trying to launch a business, but I thought the way to identify whether you’re is single is to not wear a ring. The absence of ring.

If a dude’s at a bar, and he notices that minx across the room has a silver band on her ring finger, the making-eyes action is over. He doesn’t think to himself, Say, that sure looks like wedding ring, but maybe I should inspect whether there are interlocking symbols on it that will identify whether she plays for my team and/or is single. No, that guy is on to his next lady prey and MGD 64 in 1.2 seconds.

Gould and Gilbert are counting on the newly divorced or otherwise freshly single people to jump on this bandwagon, eager to show off their available status. But as a divorcee (I love calling myself that, it seems so highfalutin yet scandalous), I can say that the best thing about becoming single again was taking off that ring.

Dude, check out our slide show featuring the cast of Vaudezilla’s Rollin’ Out of Here Naked: A Big Lebowski Burlesque, hitting the Gorilla Tango Theatre stage Saturdays in September. Just don’t spill your Caucasian in your mad scramble to grab tickets.

Tomorrow night (Tuesday, August 11) at 7pm, the Sex Positive Film Series features the film Liberty in Restraint at the Hull-House Museum (800 S Halsted St). According to Early to Bed’s blog (e2b is a community sponsor of the film series), the 2005 film explores Noel Graydon’s journey into the world of bondage, discipline and sadomasochism (BDS&M).  To learn more about this amazing (and did I mention FREE!) documentary film series, visit the Sex Positive Film Series web site or call 312-413-5353 for information or ticketing.

Check out my weekly In&Out sex column in TOC or write to me with your sex questions at in&out@timeoutchicago.com.

Ed. note: If you happen to have eyeballs, you may have noticed that the two singles on the cover of this week’s issue, Grace and Charlie, happen to be pretty attractive. Did sparks fly during that cover shoot at Vertigo? Grace gives us the dirt.

Photo: Jimmy Fishbein

New to the whole cover-model scene, late last Monday I was excited but nervous to check out the Time Out cover shoot held at the swanky Dana Hotel. When I found out I was going to be featured in the article, I thought that was enough revenge against a particular ex-boyfriend, but the cover opportunity was just too good to pass up. Armed with my best friend and fellow single Chicagoan (if you want to go on a date, bring a friend and I will too!), we attempted to meet the hair and makeup crew at the psychedelic “Nirvana Suite.” Thank goodness we got too scared by the lack of signage and loud noises coming from behind the door, because when we found a PR lackey to do it for us, it turned out that a little nirvana was being achieved at a Playboy shoot going on in the suite. Just to make sure we “Time Out people” stayed away, they plastered a large sign on the door—guess we didn’t make the cut for that photo shoot.

In the second “Nirvana” suite, I got changed and primped for a “sexy nighttime” look. Charlie, my eligible bachelor co-cover model, got off easy with only a little concealer and powder to cover the aftereffects of a long bachelor-party weekend. After what seemed like eternity (and was long enough that my friend had to leave to make her train), I was led up to the Vertigo Sky Lounge to meet Charlie (who also had the benefit of a few vodka tonics as he waited) and the photographers.

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…is a whole lot more fun than all that boring talk about abstinence, disease, etc. This story about the British Health Service’s new take on sex education reads like something straight out of The Onion. A new pamphlet designed for sex ed classes is titled “Pleasures” and features a masturbation section called “An Orgasm a Day.” Why make kids feel bad about sex when it’s so much fun? Excellent point. Anyone think the horny bastard who first floated this idea ever dreamed someone would take it seriously?

Summer can be quite a turn-on: Lots more skin gets exposed, it’s hot and sticky, and there’s all kinds of food on a stick that one can eat in a suggestive manner (pickles, y’all!).

But what to do when you have all this amorous capital and nowhere to spend it? That’s where TOC comes in. We’ll help you find that special someone, that perfect companion who looks great on your arm as you sidle up to the Hideout Block Party, rooftop bars, Ravinia and more. And hopefully is a great long-term match—if you’re into that kind of thing.

Here’s how to get in on the TOC love connection: E-mail summerfling@timeoutchicago.com with your name, age, neighborhood, photo (very important!), your match preference (girls or guys) and a few events, concerts, fests, bars, restaurants, etc. you want to hit this August and September. You may appear in an upcoming issue!