Reddit, what was the boldest sexual advance that you ever made?

I'll tell you all the pickups I can remember.

I went to an all-boys boarding school, in England, during the Bush presidency, so you can imagine my American accent and exceptionalism didn't go down well. I left that school strong academically, but weak socially, sexually and spiritually. College was a fresh start, and I wanted to be the confident, popular kid...so first freshman party, I see a beautiful woman dancing with her friend in the middle of the party and I say, "Come dance with me." It worked and she became my first girlfriend.

Second one we will skip because I was super drunk and that was a mistake. She basically picked me up anyway.

Third one we were chilling in a one of the dorm rooms, me, the lady, and her friend. Her friend left the room to use the bathroom, so I took the opportunity. She was laid out on a beany bag and I just stood up, walked over to her, and kissed her while she was lying there. She became a longtime lover but we never dated properly...there was this one night after we knew each other well, and she had had a bit to drink...I swear to God she came 20 times in 30 minutes before I stopped counting. Yeah, pretty glad I made that move, and it was probably also my most aggressive.

I've also had women make moves on me a couple times. Most recently in Paris, a woman told me she, "Wanted to give me pleasure," which was an instant winner. My second girlfriend also sought me out at a party. We met each other through friends on a trip to Joshua Tree. I watched her camp around for a couple days but never approached her. She was super beautiful, but for some reason I didn't do it at the time...but my luck was in, and she saw me at a party, and just came up to me and said, "Hey!" and we started talking. Took her back to my dorm and we're listening to music and she kisses me first as well. There is little more attractive in life than a woman who knows what she wants.

I've also elicited moves from women. Was flirting outrageously with a girl in her apartment. Her brother and his friends leave, and she asks, "What do you want to do now?" and I said, well, we could make out. And she says okay, so I say, "Are you going to kiss me? No one ever kisses me..." sad puppy eyes.

The only one one-night stand I've had in my life, I just asked her if she wanted to sleep with me; she was pursuing me aggressively all night, so at that stage you just invite her over.

I think most of the time woman want a man to seize the moment, that lull in the conversation she breaks with a soft sigh or heavy breath, and just kiss them. But last weekend for example, I was in a situation with a woman where she talked me into having a crush on her. I'd missed the earlier opportunities to be direct and just kiss her, because at the time I was thinking of another woman, before I spoke to this one some more and realised she was cool. So I asked her if I could kiss her, instead of just doing it, and she said, 'No.' Followed by something along the lines of maybe tonight. I've turned No into Yes (more like yeaaaaahhhhhhhhshsssssss) before more than once, but there is something incredibly attractive about a woman, like I said, who knows what she wants and seizes the moment. So that's a tip ladies, if you don't get approached in the exact way you'd hoped, but are into the dude...'No' is the least sexy thing to hear, ever, and 9 times out of 10 you'll miss your shot by not going with the moment.

/r/AskReddit Thread