My Trip Out

Gay married man coming out story

I’m not a slut — I’m just popular

In Chicago. I blew off a business dinner and headed up to the Boystown area in the early evening. What a great place, makes DC look downright dumpy. Huge assortment of bars and restaurants and without exception, everyone was downright friendly, they’re not just growing corn out in Iowa anymore from what I could tell.

I went to a couple of places for a quick drink, but the recommendation was Roscoe’s on a Tuesday, drag queen night. Off I go. Roscoe’s is a huge version of JR’s (in DC), wood interior, multiple bars, dance floor and a small outdoor patio for smokers. I start the evening with a omen, older guy, nicely dressed, totally gray hair and I chatting as I pick up a drink at the bar. “Enjoy your evening, you’re tall young, good looking and just emit a great personality, you’ll get hit on a lot, be careful”, he wanders off. He’s told me he was 42. Immediate ego boost for my 46 years.

Out of the gate I run into Eduardo’s Chicago twin. Attractive, loads of hair, smartly dressed, beautiful eyes. He’s by himself, waiting for a friend, doing what I do when I’m by myself in a bar, looking at my cell phone.  I do a low fly by to chat, he’s Puerto Rican. He smiles, we talk, he seems disappointed I’m from out of town, I smell high maintenance, he wants me to chase him. I’m not in the mood. I’m proud, I walked away.

Out of the shadows pops Eric, “Hi! You look lost, why don’t you come talk to me and my friend”. Blond hair, fair complexion, Eric is the dictionary reference to the word, “twink”, he’s cute, thin and definitely gay. Why not I think? Eric is 24 and introduces me to his friend and we sit and chat.  A warning light comes on, shields up, for some reason. Talking I realize how screwed up this guy is, 24 is a young age to be off the tracks already. It’s apparent, Eric is simply looking for someone to take home. It’s not going to be me though, no thanks. I see him later that night with a new guy, glad that’s not me. Another good call.

During the evening 2 pairs of guys are roaming the bar representing & pouring sample shots of a nasty vile energy caffeine drink called Sparks (from Miller Brewing). This same guy comes by 4 times. Sid, is late 20’s, 5’9″ dark complexion, very personable with a beautiful smile and one incredibly hot body. I tell Sid that he should be working the rest of the bar and OK I’ll buy a one of the drinks. “I like being here with you, you’re really easy to talk to”. Ego boost. We continue to talk, he’s well educated, good real daytime job, he’s helping a marketing friend tonight, lived in Europe for a while.

Sid eyes are getting to me, they sparkle. “You’ve got a great dark look, what’s your heritage?”, I venture. “Oh, I’m Mexican, I’m originally from Monterrey”. MAYDAY MAYDAY, I’ve struck an iceberg, send help now. “I have to tell you I have a little Latino problem”, I continue leaning down to kiss him on the cheek. “Well it’s good I’m a little Latino!”, he laughs. He pulls my head down and starts whispering in Spanish to me. Don’t bother sending a rescue team, my ship is sunk, sadly there were no survivors.

Sid goes back to working the room, but 15 min later comes back, he wants me to fill out some registration form for a Sparks contest. OK. He turns around, “use my back to write”. I complete the form. Sid then stuffs the form in his pocket. His marketing partner starts laughing, “he just wanted to get your telephone number!”. That’s OK, I hope he calls.

I’m watching the drag show. Never seen one before. It’s actually pretty amusing. It’s getting late for a school night. I turn, to my right is a young black guy decked in Abercrombie & Finch, smiling, you see his bright personality. I’m thinking younger version of William (back in DC). I smile back, he jumps in. “I’ve been trying to get your attention all night”. Who? Me?

Richard is in top physical shape, he’s tall too, 6’1″, tennis player body. We move back to talk. He’s very sweet, D&G cologne, black guy who sounds white. He’s also 22, lives at home, daddy paying the bills and has just come out. I’m setting a world record for myself tonight I’m thinking. He’s all over me, like a puppy with a new toy, it’s fine, he’s just having a good time.

Richard’s got to drive back to the suburbs, I need to get back to my Magnificent Mile hotel. We exchange telephone numbers. I slip out and fall into cab. The night ends. It’s just after 1:30 a.m.

Prologue: Sorry for the long post and all the details. But I needed a bit of an ego boost. Was worried, I’d lost my “show” mode capability to meet nice people. It’s hard to put yourself out there. I also got re-confirmed that I am simply not interested in taking someone home on a first encounter. There were opportunities last night, I passed on all of them. I like getting to know someone first. That’s going to be my game.

3 Comments

  1. Will I’m delighted that Boytown was such a success for you.
    I also like the new attitude of getting to know guys first. There are a lot of guys out there you might not have a romantic interest in but would make great friends. Friends are always good.

  2. Wow that’s incredible. Everytime I go to a bar I end up standing alone and talking to no one. I usually leave dejected.

  3. I fear I am with Brent. Went to Roscoe’s on a Thursday night, was not that crowded and just could not connect.
    I understand the getting to know. I had a great night last night with a recent friend and while the time in his apt. was incredible,the wandering the City together is what made the evening.
    Enjoy Chicago- I have come to love the place.

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