What was the boldest sexual advance you ever made?

The most memorable recent one was fairly random...

A friend and I had gone out for a couple of drinks after work but it had gotten a bit out of hand and we'd ended up going into town and ended up at a tiki bar/club.

We'd ended up befriending some nurses that had finished their shift and had a bit of a chat with them.

Basically, the club kicked out around 4am and myself and this nurse ended up separated from our friends. Turns out her friend's house that she was staying at wasn't too far from mine so I said I'll share a taxi and pay for us both as I wouldn't like to leave her in town on her own i the early hours. Literally was just doing a good deed.

We got chatting in the taxi queue and somehow ended up talking about one night stands and things. Finally got in the taxi, which was now heading out of town and she turned to me and said "what's the naughtiest thing you've ever done on a night out then?". I'm usually quite socially awkward but out of nowhere I playfully said "Probably this". I then ran my hand up her leg under her dress and reached into her underwear. I whispered in her ear not to make a sound and then played with her the entire way to her friend's apartment. She came just before we got there.

We didn't even know each other's names or anything about each other and just went our separate ways. The anonymity and spontaneity of it all made it even better. No idea if the driver knew or not.

/r/AskReddit Thread