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My First Time
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I grew up very sheltered, which meant I was a late bloomer with girls. My first date was with a woman a number of years older than me while I was still in college. It went well and, other than a lot of nervousness and fumbling over words. At the end of the night we went in to hug and I ended up ejaculating in my pants. I figured I really messed up and that she wouldn't want to see me again, but she ended up calling me and we had a long conversation. The entire time I was trying to keep it together or bring it up and make some excuses but she skirted around the topic.

We ended up going out for a while so she was my first real girlfriend. Later she confessed that she knew immediately and that's why she wanted to see me again. Things had changed though, I never felt quite right with her and the age difference was very apparent.

I was mortified when it happened and to this day I always worry it's going to happen again.

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26 posts with the exact same title by 21 other authors
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10 months ago