Chicago 2018

I was telling some friends about my time in Chicago around this time last year and they enjoyed the story. Maybe you will too.

Around two years ago by now, I was sitting at tapas1 with my good friend, Amanda, drinking our favorite pink sangria and texting her boyfriend's wife about what type of (surprise) engagement ring my friend would like best.2 To be clear, this was after our waitress/friend had told us about her wedding and baby plans with her girlfriend. Apparently, her lesbian twin sister who was already married just had a baby and the process was smooth.

It was the usual Friday routine so after we ate and got tipsy we headed upstairs to hit the bong and dance around until one or both of us passed out after the long work week.

Flash forward a year later and I'm flying into Chicago from Costa Rica to meet her at the airport in a reunion of tears, laughter, and more tears. Her wedding was in a few days and so much was left for us to do. First tacos though from the best taco place in the city which is next to the gay bar, the Jackhammer, and leather sex shop. The place is open all night and after 12AM count on seeing costumed men ordering tacos and making out.

I spent the night with her in the same building I used to live in. You know that saying about how when you return to a place you find that it hasn't changed but you yourself are different? It's true and at times makes me nostalgic for the person that I used to be.

The following morning I walked the fifteen minutes to meet my other three friends at their new apartment. We drove to Boystown for a boozy brunch. I can't remember the name of the restaurant (probably due to the amount of Bellini that was consumed) but it was great and as we were finishing up a drag show was starting. They walked with me to a sex shop to help with my task of picking out butt plugs and other such items. I was looking for a tail and the choices were slim. The first tail plug I picked out was rainbow and we agreed that it was much to sugargay so the blue unicorn one was selected. I was surprised to hear that they were worried for me because of the size (which was the smallest) of the plugs. Purchases were made and I walked out with a bag full of plugs, tails, and double ended dildos. From there we headed to my friends car which was ....not in the spot she left it. What no one noticed before was the tow signs and yup her car had been picked up. She started crying, my other friend complained about not wanting to pay for this etc., and I stood there with my bag full of toys. Another girl picked us up and the 200 was paid to get her car out of the impound lot. Damn the man. Enough of this for one day. I linked back up with Amanda for wedding shopping.

Chicago has this street lined with stores which sell fantastic cheap costume jewelry. So many stores and such pretty things. After shopping, we spent the rest of the night laughing until our stomachs hurt and sitting on the beach listening to the sound of the waves from cold Lake Michigan.

The next day was her wedding in the evening and she had a hair and make up appointment in the morning. I woke up to find her crying in panic and I am still to this day ashamed to admit that I was unable to console her. I got her to focus on my list of tasks to do rather than hers and we went on a scavenger hunt through the city for things like Russian sprats (which we found because Chicago is great). By the time we got to her wedding she was done crying and we were ready to celebrate. One of our friends gifted her home made weed cookies which were consumed at the table. Poly weddings are special, the amount of love that goes into the wife being the one to marry the two off is something to see.

The next day was my last day in the city and was mostly spent chilling, drinking, and eating at various peoples houses. There was another boozy brunch, more weed, and of course tacos.

Amanda and I went to the airport together the following morning in a long and bitter sweet car ride. The emotions were short lived though because I almost missed my flight due to the airline not wanting to sell me return tickets. I never before ran through an airport to make an international flight but hey, I did it and all was not lost. Even the guy driving the luggage carriage was cheering me on to let me know I made the flight! That's pretty much Chicago though. If you are smart enough to look past the idea that bullets are flying past your head at any given moment then you'll see the friendly, accepting, and sometimes high cast of characters who make up city that I love.

Pictures below are from Chicago, the wedding, & as a bonus included are additional unflattering images of me mouth-wide-open and midcackle!

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  1. My favorite tapas spot was below our apartment building. The building itself was on the same block as the beach and the neighborhood weed dealer hung out front for a trifecta of convenience. []
  2. I'll never forget the day when she called to say she had something important to tell me and would understand any reaction to the news. Her new friend had hooked her up with her husband, she was in love with him and now in a polyamorous relationship. I told her that was gross and was ashamed of her life choices. Or possibly I said what any true friend would say, which is that I loved her so much and also I had already been in a poly relationship. []

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