Chicago Sex Tour: Sex in the Windy City

Taking the Sex in the Windy City Red Light District Chicago Sex Tour with Weird Chicago.

So in typical Val/Emily fashion, this is how our Friday night plans of taking a Chicago sex tour around the city came to fruition:

Val: Look Em, Weird Chicago has a sex tour of Chicago!

Emily: I’ll get the tickets!

Really, neither of us needed any convincing that taking a Chicago red light district tour was a BRILLIANT idea. And really I could have said any event in there and we’d both be up for it…

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After work I met up with Em, her coworkers, Parker (who DID NOT bring any hot law students with him), and Julie at Cactus where we got some beers and chatted (except not with hot law students). We left shortly after though to go grab dinner.

We grabbed a cab from an awesome cabbie and got dropped off at the Hard Rock Cafe. We got cosmos and purple hazes. The waiter made us get those instead of Irish coffees. He was cute and an actor and from Effingham and didn’t like when we asked about the cross. We left him our numbers…

After dinner we went outside where our tour bus was waiting…

Our bus, of course, being the bus for the Sex in the Windy City Weird Chicago Red Light District Sex Tour of Chicago!

Our first stop on the tour was an “Adult Book Store” where our guide, Ken Berg, showed us around, explained the differences between types of butt plugs, anal beads, vibrators, etc. etc… Then we were taken into the private booths in the back of the sex shop to watch porn. Apparently it is actually illegal for women to be back there. But whatever.

You had to put tokens into the booth to watch it and then could flip the channels. There was even animated porn on one of the channels and some guy on guy and a lot of anal. Just in case you were keeping tabs.

This creepy guy then came out of a booth and introduced himself to Em and I.

He was kind of creepy.

The next stop on the tour was the liquor store to get some booze. Em and I got two big bottles and shared. I was already drunk by this point anyways and had to pee pretty badly, but you kind of have to drink when you’re in a sex tour bus looking for sex-related things.

On our way to the next stop we drove through the Viagra triangle (so named because it’s a popular are for older men to take their younger women), and heard all about the advent of brothels and playboys in the Windy City. My only gripe really was that we didn’t really see any of these places on the tour, we were only just told about them.

Oh well, because next up…

It was time to play “Spot the Ho!” aka “Ho or CVS (Common Variety Skank).” We drove up and down Lincoln Avenue in an area where all the hooker motels apparently are. We spotted plenty of CVSs and we spotted a few women who we were pretty certain were whores (we even saw one with a guy closing the door on a motel room…) It was a fun game!

We sped down Lake Shore Drive and then past Comiskey to get to our next location:

the S&M Dungeon of Miss Simone.

Basically it was a really nice apartment that just happened to have sex toys, restrains, masks, etc. over every inch of the wall. Mistress Simone is a pro dominatrix who specializes in medical play, which includes enemas and play piercings and such like that. There were several rooms and several apparatuses and a “Cross Dressing Room.”

At one point I was startled to see someone in the corner in a cage but then realized it was just probably a mannequin. But then later when I got closer I noticed he was moving. Nope, the naked, blindfolded man with a rope hung around his penis standing in a cage was most definitely a real live man…

We also saw a “full service” massage parlor that offers full release…But alas they were closed for the night…

The last stop was Batteries Not Included, which was another Chicago sex shop. We were schooled on the different types of vibrators. We were told things named after animals were good.

What I never understood? Why are vibrators and dildos always given women’s names?

Yup…it was just a typical night in Valryland on a Chicago sex tour… and how did you spend your Friday night? 🙂

p.s. sorry for the lack of photos. I really didn’t think it was appropriate to take pictures of strangers in sex stores and dominatrixes in their natural environment…

p.s. If you’re looking for more sex-related tourist attractions, check out my post on the Khajuraho Sex Temples in India.