This one's a more of an embarrassing. I've never been good with attracting women being bit of a loner, shy guy. Anyway, being the virgin that I was, my older brother decided to offer up his girlfriend at the time. They agreed it was fine with each other, and she showed me the ropes. I was pretty awkward about the whole thing, but she let me explore, kiss, and have sex. I didn't last long. We cuddled for a bit, but that's everything. She declined another go, and I respected her decision. It's a little embarrassing, but my brother loves to bring it up and laugh about it.