My Longtime Crush and I

This happened a few years ago. But for background, I’ve had a crush on this girl for forever but I could never get out of the friend zone. She got married and had a kid not long after High School but divorced him. After the divorce, she and I would hang out when we were in each other’s city but nothing ever happened. The closest we got to anything before this story was one time when I stayed with her a couple days and we took her son to the movies, I was really good with him when he got scared and after she kissed me but we stopped because she didn’t feel it was right.

Then this night happened. We were going to a local renaissance fair and a musical afterwards. When we got to the fair I wore a kilt, the traditional way and had to change in front of her at the car. She also had to change in front of me and I saw her tits for the first time. She had always had great tits but seeing them with nothing on made me horny. We had a good time at the fair and made our way to the musical. It was one we both loved and had never seen live.

During the musical(phantom if you were wondering) there’s a really great love song and when it came on I felt her head on my shoulder. I made a move and put my arm around her so she could lean into it a bit more. After the song we went back to normal but she kept peaking at me. After the musical we went and got some food and then decided to go out for drinks. We both had a bit an had to uber back to my place.

As we sat on the couch and talked and had another drink, she told me about her troubles with dating. This included her kinks that guys weren’t into.(she’s kinda dark and it scares guys away). I shared my own issues and how most girls are only looking for marriage and will get it at any costs. The conversation built tension and my all day horny was built up to the max.

When it was time for bed, I was going to let her have the bed and I was going to sleep on the couch. She got up took off her shirt, turned to me and asked if I was coming. She didnt have to say it twice. I followed her into the room and we had our clothes off in no time. We made out for a bit before she climbed on top and started riding me. She was moaning and screaming in pleasure. I eventually flipped her over and fucked her from behind. We changed positions several times and we both came at least twice. The next morning, I woke up to her blowing me and I ended up eating her out before we fucked a final time.

After that day, we entertained dating but my job was too good and she didn’t want to uproot her son’s life. We haven’t seen each other since and now she’s married and happy. I still think about that night often.