I ain't answering shit......ok like one or two things
What be yer most awkward sexual encounter?
(Hey, you asked for it...)
Dude, only you and maybe bubble would have the balls to ask this. and I respect you all the more for it.
It's hard to really pinpoint the most awkward sexual encounter, especially when I consider the knowledge I know now as opposed to what I knew at the time of the encounter. I will simply give my top 3 and let you decide for yourself.
1) I am 15 and she is my first girlfriend. She has a thing for making out in public. While I'm fine with this, because it involves me touching her boobies + I am not really fine with this because I don't want to get caught touching her boobies and then some. So we're watching the live action scooby doo movie, her choice not mine, and she wants me to go to town on her. I'm so weirded out by there being a family with young kinds like 3 rows infront of us that I ask if we can turn it down a notch. 2 days later, she broke up with me.
2) I met this chick online, on an online dating site. Long story short, she misunderstands what the word fidget means and now I'm driving to San Antonio (about 50 miles from where I live) to do her in the back of my car (a 2004 jetta. Not the ideal place for two large peple to fuck). I don't know her last name, I don't know what she -really- looks like but I'm just happy to get laid because it had been a month since I got dumped by my only for serious girlfriend. We did the deed, and it was....alright. After we're done we get to talking and it turns out she's kinda crazy. She refers to herself as "mommy" in reference to her pets, shit like that. I've never seen her again. It was my first true one night stand.
3) The last time me and my only for serious girlfrined made love. We were watching that movie with jack nicolson in a crazy house. About 15 minutes in, i noticed she looked uncomfortable. I asked her what was up and she said it hurt. I took this to mean she was not fully over a somewhat recent yeist infection. I stopped and we just cuddled for the remainder of the night. This was on a sunday. On the following tuesday she called and broke up with me. I realized, mothns later while thinking back on the situation that she probably didn't feel anything wrong at all. She just didin't love me anymore and didn't want to have sex with me. In retrospect, it was really awkward.