Weegee’s Lounge on Armitage is one of my favorite watering holes when I visit Chicago on business.  Something about the place brings back memories from my college days in Boston.  A tin ceiling painted an off-white coupled with some old-fashioned hanging lights just all felt familiar to me.  

My second Grey Goose Martini was excellent as usual. The vodka was having its effect as I munched on an olive. 

“Bartender!” shouted a woman who just walked into the establishment. I turned to see a beautiful middle-aged woman in her perfect little black dress that is a staple in every woman’s wardrobe.

She tilted her head a little as the bartender approached and moved a strand of her short strawberry blonde hair behind her ear.

“Vodka Martini with three olives.” She said as she took the corner bar seat next to me.  The bartender went off to mix the classic cocktail.

I absorbed with a practiced glance the woman sitting next to me. The diamond on her left ring finger told me a lot. Her husband had to have been well-off to afford what I determined was at least a two-karat stone.  She looked beautiful, but haggard.  She seemed so tired as she turned her phone upside down on the bar. It was clear that she was here to get away from something or someone.

“Tough day?” I asked her.

She turned her head slightly and I caught her light blue eyes in mine. I watched as her expression went from annoyed to circumspect. “Does it show?” she said.

“Between your body language and your drink of choice, it was pretty easy to guess,” I said with a grin.

“Aren’t you observant.” She glanced up at the bartender as he approached with her drink.

“Another one.” She said quickly to the bartender as she took a big gulp of the newly arrived libation.

“Apparently a really bad day.” I said with a raised eyebrow emphasizing the word “really”.

The woman chuckled.  “Do I know you?”

“No, I am from Cincinnati up here on business. I come to this place whenever I am in town.” I said with somewhat of a reminiscent tone.

“This is the first time I have been here since I met my husband… many years ago…” she trailed off as if her mind drifted off to another place and time. “I forgot how perfect the martinis are here.” She continued as she finished her first drink with another big gulp.

She looked down at her phone as it started buzzing. I watched a cloud of sadness wash over her entire person.  The dread was very clear as she rested her forehead in her hand and stared blankly at the electronic interloper. Her second drink arrived, and she treated it similarly to her first with a large first gulp.

With a deep breath that I could have mistaken for a sigh, she raised her head and straightened her back like she just gave herself a subconscious “suck it up buttercup” pep talk.  I watched as the sadness faded away and she reached for the toothpick spearing her three olives.

We chatted for a little while. It was an easy conversation for both of us.  I told her about my family, my job and a little of why I was in town.  In return, she told me about some great places for dinner and drinks. As we started our third martini the conversation drifted to her dreams that were never to come true.

“It’s not too late,” I said encouragingly.  “You are still young and beautiful.  Just take that first step, it is always the hardest.”

She smiled at the compliment and touched my left arm.  I was finding myself very attracted to this lovely creature. I guessed she was 5’7”. She had a runner’s body with long lean legs. The black dress perfectly displayed her cleavage. I have had one-night stands on past business trips.  I didn’t travel much, and I didn’t cheat on every trip, but there was precedence. 

“Do you want to get out of here?” I asked.

She looked at me thoughtfully for a moment.  She knew that my comment was a euphemism for doing something much more intimate.

“Where’s your hotel?” she asked.

I smiled as I stood up and dropped $200 on the bar. “Not far.”

I opened the door to my hotel room and held the door open for her.  As soon as I was in the door she turned and pinned me up against the closet with a hard and passionate kiss. The evening was a blur of passion and flesh and warmth.

It felt like the goddess under me was trying to suck my soul into her through her warm folds. The soft textures of her tunnel massaging my cock with every thrust pulling me deeper into her. We fucked hard to at least two orgasms each.  In the afterglow, we giggled like teenagers for a few minutes as we caught our breath.  I watched as her c-cup breasts rose and fell with her breathing.

She turned and looked into my eyes for a long minute. Tears were forming. My expression changed quickly until she touched my cheek and said in a reassuring whisper “No. I wanted this too.” It was obvious she was feeling something deep from some long-ago memory in her mind.  We cuddled together and slowly drifted off to sleep.

I awoke at 8 a.m. to an empty bed. I didn’t mind, but it would have been nice to at least know her name. Resigned to get ready for my last workday in Chicago I turned on the TV news.

“…Monica James, the socialite that turned states evidence against reputed mob boss and husband Michael James was found dead of a gunshot wound early this morning near the Chicago River.” The picture they showed didn’t do her justice, but it was clearly the woman I made love to last night.