A Tale of Three Dates: Part 1

A Tale of Three Dates: Part 1

Three dates, three downers.

This is the first of a three part series describing triple disappointments in dating, and asking the question we all ask ourselves… “Is it me?”

Note: graphic language, brutal honesty, a true dispatch from the gayborhood.

Date #1:

I had agreed to be set up with an acquaintance of my best friend, Dan’s at Sidetrack. Hesitant, hoping for the best and expecting the worst, I still went. I walked up to see Dan standing next to an attractive, buff, brunette, with stunning green eyes. I smirked, surprised at Dan’s pick. As I got closer, the hottie walked away. Apparently, I had jumped the gun.

“Hey,” Dan welcomed. I waved as I chopped my way through the crowd. “O.K. So, this is Ted,” he displayed as a man came around from behind him. I cringed, squinting with one eye open, prepping myself. Soon, relief took over when an adorable, slim-built, brunette, with warm brown eyes reached out, “Hi. Ted,” he introduced.

“Erik,” I replied with a bit of pleasant shock in my voice. I looked over his shoulder to give Dan an approving look. After the intros and some witty banter, I began my line of questioning. Although, a bit shy & reserved, I learned Ted was a successful business man working for a Fortune 500 wireless company, lived downtown, loved the Chicago White Sox & liked to write in his spare time. Asides from the sports thing, I was on board. The night went on pretty much without incident.

What better way to conclude the success of a fix up? I let him take me back to his condo. When I walked in, I was astounded at the space. Exquisitely designed custom furniture filled the rooms. There were 15 foot, floor to ceiling windows that overlooked the Mag Mile. I stood gazing. Before I could take in the view, I saw the reflection of Ted rushing up behind me naked, tossing me on the bed. He climbed on top of me & began stripping off my clothes. How could I argue with that?  He was very intense. I wondered how someone so reserved could have such…stamina in bed. As he threw my legs over his shoulders, I thought, Who cares? But before I could even get into enjoying one position, he would switch it up. “Let’s do it on the dresser!”

Then, he picked me up & slammed my back on the dresser top. “Now let’s do it in the doorway,” he moaned in between deep breaths.

He picked me up & threw me against the door jam with my back arched towards him. “Now let’s do it in the chair!” He laid me down head first in a crescent shaped leather chair with my legs over his shoulders. Not the most comfortable position.

“Now against the window!” Huh? Before I could argue, my face was pressed against glass & he was thrusting into me. Albeit, it was kind of hot, I just couldn’t get into it out of sheer exhaustion & nervous contemplation of what he was going to do next. So, while he pounded away, I surveyed the street below, seeing if anyone was having a sale.

Ooh, H & M! 

I was snapped out of my stupor when he began to come & grunted, “How do you like getting fucked over Michigan Avenue?! Yea!” It took all I had not to laugh.

Keep watching this blog for for Dates 2 & 3…

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