The Chicago Chronicles Part I: Sass & Class

Chicago, Piano Bar, Redhead Piano BarI didn’t realize I was being sassy until I saw him copy my pose.

“Jim?” I said, as he approached the elevator bank.

“Anais?” he replied, as he leaned against the wall with his right hand and put his left on his hip. That was definitely sassy.

“Would you like to join us for a drink?” I asked, now standing up straight and un-sassy-ing myself.

“Sure,” he said, as we all got in the next elevator together.

We had just met at an industry conference and I remembered talking to him earlier in the day and liking his eyes and thoughts. He talked like a human being, not like a marketing machine–what I was used to with most finance guys. I didn’t know anyone in Chicago and a friend, who was largely known as the industry sleazebag, had just asked me out for drinks. He would likely be a good source for stories, but annoying. I didn’t want to go alone with him, so I used Jim as a buffer. Besides, he was a local and would probably know where to go.


A piano bar nearby. Someone was playing something blues-y. I ordered a gin martini, dirty. We talked about the industry, current events, gossip, traveling. I don’t remember, really. Mostly, I was just staring into his eyes. They were a perfect piercing blue. Dark eyelashes that naturally curled upward, probably the envy of every woman who spends time trying to curl hers with that ridiculous-looking instrument in the morning. They were kind, pretty, almost feminine. But the rest of him wasn’t feminine at all: dark thick eyebrows, a square jaw, broad shoulders and I could tell he was well built under that suit.

We drank more. He suggested going to another bar. Said he knew many nice ones in his neighborhood, but couldn’t possibly go there “looking like this.”

“Looking like what? In a suit?” I objected, knowing all too well about switching between the professional and alternative worlds. “Just take the jacket and tie off, and you should be fine.”

He looked at me skeptically and didn’t seem to agree.

“Oh, come on!” I was feeling feisty and proceeded to undo his tie for him.

“What are you doing?”

“I’m taking it off, what do you think I’m doing?”

“In fact,” I said, as I took it off him and looped it around my own neck. “There, that’s better.”

He offered a half smile. Larry, our industry friend, looked at us with a mixture of amusement, annoyance and discomfort.

“So, can we go to that bar now?”


Sarah Palin naked, polar bear, rifleThere was another bar, or three. One of them was a relaxed dive-y pub with dark wood paneling. It had paintings by local artists on all the walls. One of which was of Sarah Palin standing naked on top of a dead polar bear and holding a rifle. It was around the time that she and John McCain were running for office against Obama and Biden.

I kept switching between whiskey and gin, not minding the headache it’d give me later, and becoming sassier as the night wore on. At a certain point, I wound up revealing that I was taking burlesque classes in New York and was due to perform later that summer. This somehow led into talking about my being bisexual. Larry asked me if I had ever had sex with a woman, you know, with strap-ons. I said I had. Jim said something to the effect of: “if you aren’t born with a dick, you’ll never know how to use one like a man does.” I scoffed and rolled my eyes. We ordered more drinks. They threw the straws out of theirs.  I told them I thought it was funny that men are always so against straws.

“Straws are just fine by me,” I said. “In fact, I quite like them,” as I closed my lips around mine, pursed them and looked up at them, or really just at Jim, seductively.  They looked at me with hungry eyes, the way that men look at you when they want it, but can’t have it, at least not right then and there.

Every time Jim went to the bathroom, to get drinks or was otherwise out of earshot, Larry kept asking me: “You like this guy? You want me to leave? I can leave, you know.” I wasn’t sure what I wanted. I wanted a fun night out in a new town.  I wanted to wash away the bad taste of last night, which I had spent with a crazy drunk anarchist in New York. But then, yes, I wanted him, but I didn’t want to admit it.


The three of us wound up back at his house later. He gave us a tour and fed us more wine. Two floors and a basement. He lived alone. There was no evidence of a wife or a girlfriend, I noted to myself. Several bicycles were hanging from the ceiling in the basement. He was into cycling. Had participated in some races, including the Tour de France. I had never ridden a bike in my life.

Larry and I roamed around his house, talked and sipped wine, he asked me several more times if I wanted him to leave. I kept shaking my head: no. But he opted to go back to his hotel soon anyway. Jim walked him to the door and pointed him in the direction of where he can find a cab. I was almost blind drunk at that point, but I realized I was making a decision by staying.

Jim sat next to me on the couch, my back was turned to him and I had hugged my knees into my chest. He put his arm around me, then moved it over to my legs and between them. He started rubbing my crotch with his fingers. It was probably the first time anyone had gone straight there without kissing me first, I thought. I wondered if I should turn around and kiss him or keep going in “Pretty-Woman-fashion.” Thank God there was a precedent for this. Eventually our bodies naturally turned in such a way that we collided into a kiss. His lips were soft but intentional, firm. Our hands wondered all over each other’s bodies, we started drunkenly fumbling around with each other’s clothes. Buttons were suddenly a very cumbersome matter. He took my pants off and put his hand on my cunt that was super wet from hours of anticipation. I could see he wasn’t surprised.

When I was completely naked, he told me to go to his room, I obliged and crawled into his bed, under the covers. Maybe I was trying to cover up my nudity, but was this any time for modesty, really? He joined me in his room a few minutes later, set a glass of water down on the nightstand, stripped the covers off the bed and off of me. He was completely naked now, too. We rolled around and wrestled with each other in bed. He pulled my hair and bit my neck. The next thing I knew, his cock was inside me. Suddenly, it felt like I wasn’t just waiting for this all night, I was waiting for it for a much longer time. A missing piece of some puzzle. He felt like everything I ever wanted. I went from obsessing with his eyes, which I could barely see anymore in the dark, to obsessing with his skin. It was tight, toned and completely smooth, he had no hair on his chest or back at all. I stroked his arms as I felt him slide in and out of me and pressed my legs around his torso. He fucked me hard and rough, like the dirty slut I felt I was being that night. And, at the same time, slowly and rhythmically, methodically, as if he were a boyfriend that loved me for years.  Maybe he was right. Women can’t learn to fuck this way.


I woke up the next morning with his arms wrapped around me. It took me a few seconds to remember where I was and what was happening. He stirred in bed behind me, then hugged me tighter. My alarm clock pierced through my groggy consciousness. I turned it off. He started grinding against me. I felt his cock getting hard. This time he had me bend over in front of him, so he could fuck me from behind. I wasn’t drunk anymore. I felt clear and lucid. My mind was registering every inch of him that was inside me, next to me around me, slapping my ass, pulling my hair, drawing me towards him as if his life depended on it. I looked out his window, which was directly in front of me. It was gray and raining, I could see the back of another building and a plant that vined all around it. The raindrops would fall on the leaves, weigh them down and then roll off. I filed that image away in my mind, wishing that our brains worked like computers. That if I saved that picture on a disk or USB drive, every time I’d pull it up, I’d also feel the way I felt when he was fucking me.


He decided to work from home that day, as we had only slept a few hours and felt like we had drunk our livers off the night before. I had to go back to the conference and cover it.

“Would you like some coffee,” he asked.

“I’d love some!” I said, as I jumped out of the bed and threw some of my clothes back on.

I sat across from him at the kitchen table, sipping my coffee, while he leafed through the morning’s Wall Street Journal. And just like that, we went back to talking about the financial news du jour.

He walked me outside to hail me a cab later. When one arrived at the curb, Jim wrapped his arms around me to say good bye. A question hung on the tip of my tongue, but I had no idea what it would even say. He silenced it with a kiss. We thanked one another for a great night and off I went, with a copy of his Journal.

I processed everything while in the cab. Was this the first time I had hooked up with someone in the industry? Yes, I think it was. Was it inappropriate? Probably. But I didn’t much care. He worked in an area that I didn’t report on much. I would never need to talk to him again. He lived in a different city. It was a fun night in Chicago. This was all. I would never see him again.