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Leather wear

One reader's first time donning leather.


Male, 27, Andersonville
My sex was always vanilla. Sure, it was gay, but I was about as kinky as a head of flat-ironed hair. Still, I harbored a sexual Mr. Hyde that needed release, and so I decided about a year ago to take a walk on the wild side. Turns out the “wild side” is Jackhammer, a multilevel leather bar with an adjoining fetish-gear shop in Rogers Park.

Upon my first visit, my eyes were immediately drawn to the television above the bar. I expected to see the Cubs game or Madonna’s latest music video. Instead, I saw a man pleasing another man in a manner similar to a farmer inseminating a dairy cow. At that moment I wondered if I was not unlike that man’s fist—in too deep.

Thinking if I dressed the part then I could play the part, I wandered into the fetish store. Although I knew nothing about leather wear, I refused to ask the store clerk for assistance, fearing I’d be discovered as inexperienced. Instead, I poked at the various-colored harnesses on the racks, rubbing the leather between my fingers to give the impression I was a connoisseur of fine fetish goods. But my self-consciousness beat out my libido, and I soon fled.

The next week I visited a friend who had a large collection of sex toys, which he proudly displayed on his nightstand. I asked him if he happened to have any leather gear. His eyes lit up, excited he had a new inductee. We went into his bedroom, and he opened his closet door.

It was as if I had found the wardrobe to Narnia, if Narnia were inhabited by custom-made leather harnesses with cock-ring attachments. He let me try one on, helping me weave the straps through the loops, tightening and loosening the garment so that it fit snugly.

The harness felt amazing, and it looked great, too. An eager student, I immediately slipped on chaps and a mask (with detachable ball gag). My friend was incredibly turned on: He went down on me right there. Overwhelmed with pleasure, and completely muted by the gag, I voiced no opposition, and we ended up having mind-blowing sex, complete with cock rings, nipple clamps and a roll of bondage tape.

After that, going to the leather bars was no longer the intimidating ordeal it once was, and to this day I get a wicked boner when I think about my first leather experience.

FIRST TIMER’S TIPS * Make sure your leather wear fits snugly but not too tight. * Sometimes the leather scene can be a little intimidating. But really, it’s just like any other scene, complete with nice guys and douche bags. Find people you connect with, and don’t be afraid to tell an aggressive guy you’re not interested. * Don’t feel the need to buy the most expensive harness or a full set of gear. Leather can be an expensive habit. Start off with a basic piece and slowly amass your collection. * When wearing a ball gag, don’t forget to breathe through your nose.


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