My friend and I were swapping "awkward sex encounters" the other day. Mind you, I've got almost zero sex encounters in total, unless you count the 8 years with the ex, but to call those "encounters" might even be pushing it a bit.
Anyway, right around the time my divorce was getting under way but before Gray and I were technically a couple, I flew to California with my sister and her newborn to visit family. I had met a guy through work who offered to get us free tickets to Disneyland and California Adventure, so of course we took him up on it. Trouble was, he wanted to go with us. And not only go with us, but meet us in Anaheim the night before and stay in a hotel near the park.
My sister, crazy new breastfeeding mother that she was, opted out, but I agreed because he and I had been on a couple dates and got along pretty well. And I really wanted to go to Disneyland.
Here's where it starts to get awkward. The plan was for me to go stay the night with this guy AT A HOTEL, and then my DAD would bring my sister to meet us in the morning.
I know. But it made perfect sense at the time.
Having never been with anyone other than the ex, I was bound and determined to have a good time. Except it turned out that this guy was a Flipper Face. And by "Flipper Face", I mean that I may as well have been making out with a dolphin. It was AWFUL.
He was a very nice guy, and generous, don't get me wrong. But that just meant that I was a prostitute, not that I was into him. Right?
Ok, so the next morning, my poor horrified father (what must he have been thinking?!) dropped off my sister at the hotel and left to go home and babysit his new grand daughter.
The three of us walked uncomfortably around the theme park until around lunch time (my sister is the type to GIVE ME SHIT, so you can imagine what I heard that day despite how very hard I was trying to forget the events of the previous evening). We decided to hit up one last ride - Pirates of the Caribbean - before heading over to California Adventure for lunch where the only booze on the property was sold.
Did I mention he was a little...husky? When he went to sit in the rear of the little Pirate gondola, it literally went under water and sloshed about 40 gallons of god knows what up into the boat. He was soaked from the waist down, but my sister and I managed to ride the entire thing without putting our asses in the trough behind us, probably thanks to a lifetime of public toilet hovering.
Now we were uncomfortable, HE was uncomfortable, and it didn't take long before he began to complain that his wet denim shorts were chaffing his thighs. Great. Even better.
So we had a really expensive, marginally edible meal over at CA. AD. and a few of their million dollar keg beers before he announced that he wasn't feeling well and disappeared into one of the park's bathrooms for, like, 30 minutes or so. Time enough for my sister to go shopping and come back. THAT'S HOW LONG HE WAS IN THERE.
Then we had to buy sunscreen for him to slather on his thighs.
You know...from all the chaffing.
Then he bought us an expensive dinner, took us home, and drove to San Diego (not a short drive, if you're wondering). I nearly DIED when I realized I'd left one of my shoes in his trunk. This meant further contact was unavoidable. I could live without the shoe, but I knew he would use it as an excuse to see me next time he flew into MN.
Which he did. And then we had the horrible conversation about "what went wrong".
Wow, was that as awful for you as it was for me? Ok, so back to my original point - my friend was telling me about HER most awkward sexual experience, and it was so awesome that I asked if I could share it with you people. And she agreed, because she was drunk. Or something.
So there was this guy she knew in high school who always had a huge crush on her but never made a move because she was dating his best friend. (Ah, high school politics). They happened to run into each other years later as adults and I can't remember if she said they went on a date, but he still had a crush on her and she wasn't sure if she liked him.
He convinced her to come watch movies at his house which, of course, translates to "let's make out and maybe I'll be able to slip you a little...well, we'll just see how it goes with the making out", but it didn't take long for her to realize that he was a Hoover Face.
Her entire mouth/lip/chin area was in his mouth AT ALL TIMES. She said it was so bad that when he turned to take a drink of his beer, she pretended to fall asleep. In less than 5 seconds. And she continued to pretend to be asleep for, like, over an hour.
But he wasn't giving up.
So eventually, somehow, she decides to just leave but he really wants to get freaky, so she jokingly tells him that she'll have sex with him if he puts on her bra and panties. Mind you, she thought it would be a deal breaker for him and he'd send her on her merry way.
Except he does it. HE FUCKING DOES IT. And he's standing there in her underwear and she politely asks for it all back and she gets dressed and she leaves.
Now...I might be wrong, but he was either into lingerie or he was fucking desperate to get laid.
Anyhow, I would LOVE to hear your awkward sex stories if you got 'em. Who are you kidding, I KNOW you freaks have 'em! Lay 'em on me! Help wash the taste of Flipper out of my mouth!!