The last course of this blog binge is below. I hope you’re as relieved as I am… You can read part 1 here and part 2 is here.

Tuesday, September 14, 2010

In 1990, I moved to Chicago at age 32. I was still a total slut but I had shortened my playlist by then and stepped away from bottoming completely. On the rare times that I did fuck, I was always a top, which I definitely felt more at home doing, but in general, I didn’t focus at all on anal sex.

And then, within days of arriving, I was scanning the personal ads in the Windy City Times, a typical crappy gay newspaper, and I saw the ad for Chicago Jacks. My response was instantaneous: All I wanted to do was find them and sign up. There was no doubt that I wanted this, I only wanted to get in there and experience it myself…

The sign-up process was ridiculously convoluted. I had to make a photocopy of my driver’s license and mail it with a check for $25 to a PO box, all of which could have been a scam but I was a man obsessed. I don’t think I knew how much I’d been craving this scene until the possibility was in front of me. I though of little else. I even think I remember the moment I dropped my envelope in the blue mailbox and began counting the days until I heard something back from them. I knew there was a risk that they were just going to take my money and blow me off. That would be easy enough to do… But I was hopeful and waited.

The envelope had a mimeographed calendar of upcoming events, an address and an information sheet about the club. I mainly remember the calendar, how they had a few events every month in a re-purposed VA hall in Wicker Park owned by the Hellfire Club, a long-lived leather community in Chicago. I saw the schedule had an event for wearing Speedos, and another for underwear… My mind spun.

I will recount the tale of my first Experience at Chicago Jacks another time, but almost instantly, Chicago Jacks became my primary sexual outlet. Yes, I still cruised phone sex lines (this was before computers took over my social life) and the beach and the streets and I very certainly masturbated enthusiastcally on my own, but I was replaying my electric moments at the Jacks, remembering the feeling of multiple loads dripping down both of my legs, the feeling of a man’s impossibly firm butt as he straddled my thigh as he stroked, remembering standing and stroking cock-to-cock with a very relaxed man with a very alert penis, and moment after moment…. I loved that club.

And less than a year after finding and embracing the Jacks, I met a man while working on a play I was understudying for. He was wickedly smart, strange, very funny, talented and sober… We had a lot in common. Three months after meeting him, I told him I loved him and that same night said that I thought I might actually want to be monogamous. I meant it.

I wasn’t trying to drive anything away, and I didn’t feel guilty for anything I had been doing. I just had fallen in love. I don’t think I’d really done that before as an adult, but then again, I’d only been drug-free for two years so adult-hood was actually kind of new to me…

And so ended my time with the Jacks and so began a relationship that is about to enter its 19th year. Much later, I would find out that Chicago Jacks folded a year after I stopped going there. I felt sad.

I don’t know when I started to understand that there was a special fascination for me about the jack-off club experience, but it was definitely there long before I experienced it in the physical world. It has held a fond place in my heart ever since I saw that ad in the Reader and I think that I will always want to support it, even after I’ve lost the ability to participate myself. I know this is my kink, something most men don’t focus on, and I’m completely at peace with this. Many kinds of sex turn me on and satisfy me, and there is only one person in the world I really need to make love with, but I’m grateful that I can do this too.

As Pee-Wee Herman says, I’m the luckiest boy in the world!

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