Former Cheerleader

In high school, I was acquainted with people from various social groups. Among that group were the cheerleaders. I'm not going to lie, most weren't attractive in any way, except for one girl. She was about 5'6", thin, light brown hair, nice, bubble butt. I was good friends with her boyfriend. He was the typical high school cliche - football player dating the cheerleader. They dated all throughout high school until Junior year.

Often times, I would be walking behind them as I headed to class and I would just stare at her ass. I would be in a few classes with her so I would check her out and let my fantasies run wild. During Junior year, she moved to attend boarding school. Her and her boyfriend then broke up. Graduation came and went for me and she came back home. I moved to attend University and she stayed.

While at University, I suddenly decided to message her through Facebook - we had been Facebook friends for a few months. We chatted back and forth. She was really nice and had a great sense of humor. We talked about how we had been doing after high school and all that. Eventually, I asked her why her relationship had ended with the guy from high school - he and I were attending the same University. She said that he was physically abusive to her.

I'm not sure how, but the talk of sex came up. I asked her how the sex was with him and she said that it wasn't good. According to her, he didn't last long and once he was done then he was done; didn't care to pleasure her or make her cum. It was after this that I told her I found her attractive and how much I wanted to pleasure her. I was in the library at this time and I decided to head back to the dorms to get some sleep. I expected her to shut down the conversation, but she didn't. Instead, she asked me to tell her what I wanted to do to her. I told her how I wanted to run my hands all over her body and lick every inch of her then have her on her hands and knees as I pulled her hair and fucked her from behind. I left it at that and waited to cross the somewhat busy street. My phone went off, signaling a text message. I opened it and her text said: "Mmm. Would you spank me?" I got hard instantly. I didn't expect her to be into anything kinky. I told her I would love to spank her ass, and how much I enjoyed looking at her ass. She said how much she would like me to spank her. We ended the texting that night.

The next day, I didn't hear from her. I was busy with classes and I expected that night was just late night horniness. Around noon, I met up with a new friend I had made at University a few days before. She and I talked as I walked her to her class. Suddenly, as she and I were walking, I got a text message. I saw that it was from Alyssa and I expected a typical greeting text. I opened the text as my friend was talking and what popped up was a picture of an ass wearing hello kitty panties. Immediately, I closed the text and went back to talking to my friend. We got to her class and went our separate ways. I then found a somewhat secluded part of campus and opened the text to make sure I saw what I saw. Yes, it was a picture of Alyssa's ass in pink, hello kitty panties. Below the picture was the text: "Since you said you like looking at my ass."

Now, if you're expecting me to get to the part where I fuck her, you'll be disappointed. We never got that far. School got busy for me and she started dating a guy who got her pregnant. All these years later and she still has a rocking body. We're still Facebook friends. One day, I did ask her if there was a chance we could've fucked and she replied that it was possible, but it never would've led to a relationship as she was into being in relationships with fat guys. The one time I wish I was fat just for her.