Back to School in Chicago

By Johnny Jackhammer


I didn’t read 50 Shades of Grey.

I won’t read 50 Shades mainly because I’m a literary snob, and people I trust have characterized the series as an unrealistic description of true Power Exchange in the BDSM community.

But I don’t need that book series to build my interest in kink.  I have long been a kinkster, and my wife, GoodWitchNorth (GWN), and I have been testing out the waters of our local BDSM community.  We are lucky to live in a place that has been jokingly dubbed “the Rope Capital of the World,” so events close to home have been easy to find.

I am glad the book exists however; because anything that opens kink into the mainstream is a good thing.  But even with this advance, sexuality somehow needs to be enrobed in violence and domination to be accepted by the public.  The sensuality that makes the world go ‘round remains taboo.

But in our house, my wife and I are expanding our boundaries, taking the time to plan overnights and getaways that have a kinky edge to them.  We are glad to be over 40, which gives us a solid blend of confidence (to feed my exhibitionism fetish) and open-mindedness (which expands opportunities for her adoration fetish).  Seeking out a sexy event to see and be seen, we enrolled in Kinky Kollege.

Kinky Kollege is a weekend BDSM conference held in the Chicagoland area by the Leather SINS organization.  It’s a pansexual event featuring classes, vendors, a silent auction, networking opportunities, and a dungeon playspace open from 9pm to midnight each day.  The event is held twice a year, with “Prom” held each March and “Homecoming” held each October.  While it’s not a total hotel takeover, it is held in a private space with strict security.

As I write this, KK is fewer than two weeks out.  How does a first-timer prepare for such an event?  My thoughts are to PLAN and then PACK.


For a kink conference, we need to identify our fetishes.  Classes at the “Kollege” run a broad range.  Subjects range from “Rough Body Play” to “Tactile Torture Worship” to “Let’s Get Cracking – Whips 101.”  There are some more sex-centric topics, as well, including “How to Give a Great Blowjob” and “Playing in Public.”  I’ll compare notes with GWN, and I expect that we’ll do more than half our classes together and one or two on our own.  I know that I’m interested in a basic rope class, a session on prostate milking, and some sessions on scene creation and playing in public.  We might hit the “Fist-A-Cunt” session together, if only to watch the demonstrations.

No matter what, though, we’ll probably choose classes for the day on the mornings of the event.   Most of our interests are shared, and we’ll want to stay flexible.   You can check out their course descriptions at their website.

The schedule shows classes in the morning and early afternoon.  Vendors go all day, and dungeon play takes place at 9pm.  There seems to be plenty of free time, so I want to make sure that we also plan for some extended hang time in our room.  Perhaps we’ll make some friends!


Like every BDSM event we have encountered, alcohol is not permitted.  It makes sense, since the action can get fairly risky, making it important for the participants to keep clear minds.  Plus, sex can only be at its best when one is sober; don’t you think?  It might get rougher and sweatier when you have a jag on, but you’re more likely to reach sensual peaks when you are fully present.

Even so, our packing list starts with a bottle of good French vodka and bourbon.  We will take plenty of breaks in our room, so our list will include snacks to match as well as extra glasses to entertain friends.   I’ll make sure to grab some appropriate snacks: sharp cheddar, water crackers, hummus, and fruits.  Good things to keep Happy Hour happy.

Since the event includes classes, followed by social events, followed by dungeon activity, multiple outfits are called for.

As a man, I figure I should have some jeans and tight t-shirts, sharkskin slacks with crisp white dress shirts, sexy underwear, assless chaps (don’t judge me), jocks of various types, and maybe a spray-on tan for my Midwest whiteness.

Women have many more sexy choices available.  I, for one, am very glad for that.  GWN will have a lot of revealing lingerie, sexy dresses, leggings, garters and hose, boots and heels.   Red and black permeate her wardrobe, with some fun and sexy t-shirts for the more vanilla events (like one black shirt that just reads “Area Woman”).

ToysThe last item will be our Toy Bag – I figure that you never know what might be needed while in the dungeon.  I plan to include multiple types of lube, unlubricated condoms (in case GWN fulfills her fantasy of pegging a row of “boy butts”), rubber gloves, and cleansing wipes.  The toys should run the gamut from cock rings and vibrators to paddles and harnessed dildos.  Be prepared for anything, right?

I’ll throw in some erotica and music for good measure.  If the activities don’t meet our expectations, at least we can take advantage of hotel-style relaxation.

I hope that will cover any anticipated needs, but I’m sure there are plenty of discount stores or a mall nearby.

The hotel instructions warn that participants need to keep covered in public areas.  This is especially true in their glass elevators.  Chaps are family-friendly; aren’t they?

What if I wear a cowboy hat???

More to come on this…


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