I Cheated: A Love Story Everyone Here Can Relate To

It has been eight long months since the last time I saw her...

This time last year, ChicagoNow and I were having a wonderful relationship. We were inseparable. I remember I used to take her to the park on my iPhone, or spend a day with her at the beach, or stroll down Michigan Ave. on a crisp winter day holding each other tight. Most of all, I remember those passionate nights we spent together in bed, under the sheets, with my laptop as the only source of light. I loved it when she used to yell out my name when I said something dirty or witty. Sometimes she got angry after I did something stupid, then we would have unrelenting make-up sex for several days. I admit, I said some stupid things on purpose. Life was good my friends, life was real good.

But then I started to get cocky knowing I had this great looking girlfriend who would always take me back no matter what I said or how I behaved. Unfortunately, I did what a lot of cocky douchebag boyfriends do to a great girl, I cheated on her.

At first, I cheated on ChicagoNow with a young and attractive local girl called Chicago Redeye. She was good and she was easy...real easy. Redeye let me read her and write comments all over her using another name, and she liked it. She let me do it practically at will. She particularly liked when we did it late at night and when I was hammed-up wasted. She liked it so much she asked if I could do it faster, harder, and more often. But no floozy can keep me tied down without payment, so I had to drop that ho quick.

Then I hooked up with a gorgeous MILF. Her name was Chicago Tribune. She was old, but had a great face and a body that younger floozies would envy. At first, she acted like she wasn't having it. But all I had to do was whisper in her ear how beautiful she still is after all these years. After that, we started exchanging sexual banter over lunch. Next thing I knew, Tribune and I were doing it in taxis, on buses, on the Metra, and in front of the Sun-Times building. For some reason she and I loved to get together in public. Unfortunately, I knew our torrid affair couldn't last long.

After I ended things with Tribune, ChicagoNow still thought I was true to her. However, I think ChicagoNow knew deep down something was wrong. My cheating got worse. I started experimenting. I messed around with Out Magazine. He was young, good-looking, and very gay. Out Magazine liked to tell me interesting facts, like once he told me, "there are four times as many bottoms in Chicago than tops." I didn't really know what he was talking about most of the time, but hey, he was good to look at. Then I had a one-night stand with Al-Jazeera. She was somebody all my friends told me in the past to avoid, so of course, I just had to try her when she gave me an opening. I remember she talked bad about America and democracy when we were in bed together. I was going to comment against her views, but something about her figure just hypnotized me. It was a wild and passionate night. As we were having unruly sex, I though to myself maybe Al-Jazeera and I could work, but alas, it would have been a long-distance relationship. I left before she could find out who I was.

Subsequent to my carnal experiences with Out Magazine and Al-Jazeera, I was left discombobulated and confused. I stayed away from all technology floozies. I only used my cell strictly for telephone calls, and I stopped using my laptop all together. Then last week, after President Obama was reelected, I pressed the Safari icon on my iPhone and for the first time in a long time I held ChicagoNow in my hand. At that moment, I knew how far I truly strayed. At that moment, I knew I was truly in love.....hope she'll take me back.




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  • You hurt us bad, real bad. I just don't know.

    I think if it's going to work out we're going to have to make it Facebook official.

  • In reply to Jimmy Greenfield:

    You deserve to know that I didn't always use protection during my infidelity. I may have caught something. But a few rashes and painful abdominal pain won't stop true love, right?

  • Based on statements like on Da Bears Blog, you should hold out for your girlfriend to pay you.

    Not like the sap on the Subway commercial who gives up his sandwich just because some floozy said that she was going to be his girlfriend.

  • In reply to jack:

    Jack, I see some things never change, i.e., I still don't understand what the hell you're talking about.

  • will, hope you're well my brother. Good piece.

    We're moving maings, you should come check out the new digs in the new year at dabearsblog.com.

    Come by and post once in a while, god knows you've got nothing to write about your Browns (sorry).

    btw, wanna trade trent for michael bush straight up?

  • In reply to MB30SD:

    I'll be sure to check out dabearsblog when it comes live. Can't believe you guys are leaving. No, I wouldn't want to trade Trent straight up for Bush.

  • Welcome back Gwill!

  • In reply to Kay S:

    Thanks Kay!

    By the way, if you have any attractive and/or flexible single friends who have a habit of making bad choices, send them my way.

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