January 26th in Posso's Prompts

I was in Chicago visiting some family when my uncle took me to a bar that was totally a place that I stood out in: I didn’t have a leather jacket, I wasn’t tattooed from knuckles to face and everyone I saw had half inch gauged ears. There she was though; this girl with the brightest pink hair I have ever seen to this day. She had piercing green eyes (the color contacts helped alot) and I was mesmerized by how tan she was yet how the black of her lipstick and eye makeup stood out over everything. I was instantly obsessed. She ended up waiting on me and taking my order. We connected on how we both served drunks and people that made idiots of themselves. As my uncle finished his third ‘lunch’ of the day, he wanted to move on, but I had no desire to go anywhere that this real life dream didn’t exist. Drinking slowly, I ended up staying with her and casually chatting until she got cut from her shift around 1am.

“You want a private tour of what I do on an off night? See how a real bartender in an actual big city drinks?”

I was definitely never going to turn this down. To this day, I can still remember wandering Delilah’s, Rose’s Lounge, Irish Eyes and Lilly’s and just strolling the Lincoln Park neighborhood at 4am. We laughed, told stories of our childhoods and how we both were small time townie kids that moved to the city to get away from the people we didn’t fit in with. Shared a few Chicago dogs and made out against her early 90s Yahama Virago. She was extremely proud of her motorcycle and even more happy to make me sit behind her. We went back to her place and probably had one of the most memorable sex experiences I’ve ever had in which nothing went wrong and it was just…well it worked and it didn’t feel like work with expectations. Riding bitch through the city back to my uncles place the next day brought all sorts of looks - this tattooed, pink haired naturally beautiful woman in boy shorts and a crop top driving this nearly 300 pound grown fattie on the back of a motorcycle. Wish there were pictures on the internet of this phenomenon.

Chicago had always had my heart for sports reasons and for the complexity of the big city feel I just never felt when I’d go to Minneapolis/St. Paul. The Cubs had my heart when I was young thanks to my dad. The Blackhawks became my team when there wasn’t a professional hockey team to be found in Wisconsin or Minnesota while I played growing up. Wandering Wrigleyville and the north side made me think I had made a mistake by not living there. Sometimes I still consider moving there while I have nothing that ties me down.

I still get made fun of sometimes when my friends are out with me and a girl on a bike rides by.