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Not proud but he thinks I cucked him the first time, and well the second one, he may not be aware
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So, to be clear, I am not proud of these moments, they were done a long time ago.

In high school there was a kid that was picked on for some things that were out of his control, but also things that he was in control of. One of those things was he would wear those tight OP shorts to school thinking he was trying to be cool, but the problem is, well, everyone could tell that he hadn't grown much in puberty. The joking both to him and behind his back was merciless.

Anyways, he did start to date a girl in HS, but she knew from the beginning that things were not going to work out. When we started talking, she told me that she had told them that it wasn't going to work out, but he must not have gotten the hint. He felt that she cheated on him with me, and that I stole her away. There was some overlap over the end of her relationship and when we started messing around, so technically, he was right.

Fast forward 6 years and I moved back to the area and started working at a store to get my feet on the ground. There was a lady there who was was pretty and we really hit it off. She did mention that she had a boyfriend, but that he was small and really didn't please her. She actually bought me an expensive pair of sunglasses when mine were stolen.

I do not remember how it came about, but she mentioned that she wanted me to come over to her house one night for dinner and meet her BF. We planned to be drinking, so I had brought some clothes with me. Imagine my surprise when I met her BF, it was the same guy from HS. He also looked very surprised to see me, but didn't say anything. We had a great time catching up on life since HS and the lady was very playful with me, especially behind his back. Well we had definitely had some drinks, and they headed to bed while I went to sleep on the couch. Not that long afterwards, she came out and started rubbing me. I asked her about him and she said he was out like a light.

She took my cock out and her eyes went real wide and she said, well, now I know why **** left him for you. She basically confirmed what I always thought, he was very small. She gave me a hell of a BJ, and then told me she needed to get back to him.

I distanced myself from them after that, just because I started to feel guilty. Although in the AM, she did tell me that he woke up when she climbed back into bed and she gave him a kiss. I know, cruel..

They broke up not long after.

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4 months ago