While I was #7’s boytoy I met another woman. While at the Skokie court house awaiting court proceedings in my case for DUI number one, I took a stroll with my father and as we discussed somethings. In mid conversation I noticed this very cute black chick checking me out. As we looped around to the other side I proceeded to engage her in conversation. Wasn’t anything to fancy. Just my name, her name, basic bullshit and I got her number.
Afterwards my father and I went into the court room to have my case called. Nothing came out of this, but we’ll see you in a month and a half for more court bullshit. Gotta love the legal system.
Anyways I decided to chat this girl up via the phone and we hit it up great. At this time I had a piece of shit cell phone but at the same time a cell phone none the less. One eventful day I decided to set them up back to back. Mind you at this time I had no drivers license. I took the trains and hour and a half to my ex-gf’s house. Her and I fooled around, but stopped short of having sex. I was saving myself for possibly the other girl. My ex and I hung out abit and after awhile I excused myself saying I was going home.
I hopped on the next available bus and called up girl #8 to let her know I was coming, she gave me all the rest of the info I need then I hung up with her and called up my ex. I bullshitted with her until I got to the stop where girl numbers #8’s place was at. When I got off I realized it was on the edge of boys town and cabrini green.
I get over there and get up stairs to her one bedroom apartment. She’s just chilling in her pj’s watching porn. I was like damn. I had seen her before but she was wearing a coat. This time she had on some little booty shorts and a shirt that looked like it was going to burst from her huge tits. On top of this her waist was to say. Needless to say this was at that point in my life the hottest girl physically that I would fuck.
We started into the same normal small talk, which led into talking about sex (due to the porn), which led into kissing and groping each other on the floor. After awhile she got up, grabbed my hand and led me to the bedroom. Needled to say the sex was amazing. After blowing my load the first time we got into more kinkier talk. This led into a discussion whether I liked anal. I told her before that the girl I gave my virginity to used to finger me in the ass while she gave me head and I liked it.
This chick though I was full of shit so she hopped off the bed, went into her closet and pulled out a small vibrator. She climbed back on the bed and gave me this look like “Alright big talker let’s see if you can walk the walk instead of talk the talk”. She lubed it up, stick it in and proceeded to give me head. I loved it.
In the morning I had her drop me off back in Arlington heights due to having to work. In the weeks that followed I never called her back. For me this was a stupid mistake. We both clicked sexually and conversationally, but I allowed my feelings of loss and longing for my second love to take over and I pursued her instead.
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