"Trudy" is the most awkward person I know. She is a full-time lesbian, a part-time entertainer, and a freelance assclown. I could probably dedicate an entire blog to her stories, but instead, I'll write a few of her escapades and hope she never Googles herself.
A very good friend of mine (who's name will be changed to "Claudia") is currently dating Trudy. This is how our frightfully awkward friend wormed her way into my life.
During the early stages of their relationship, Trudy was just meeting some of Claudia's friends. One, in particular, was named Lauren. Lauren has a bad habit of dating trashy women. After going through a few detailed examples and pictures of her past flames, everyone agreed that Lauren did, in fact, make poor life choices.
Trudy kicked the awkward level up a notch.
"So, Claudia, why aren't you dating Lauren?"
-silence-
By impling that Claudia was a trashy woman in front of her friends, Trudy earned a night in the doghouse. But it gets worse.
I threw a socially awkward party at my apartment after Thanksgiving. Claudia and Trudy stopped by, each adopting a new habit to make them socially awkward. Claudia's was to slowly pet the hair of the person she was talking to. Trudy's was to rub her nipples and hump everyone in the room. "Socially Awkward" became "Awkward Rape." Even after we dropped the party theme and just dedicated ourselves to four loko and beer, Trudy shoved her hands down 3 peoples' pants and gave two surprised strangers aggressive lap dances.
Tonight's final story of Trudy is a shocker. Readers under 17, close your eyes. Parents, lock your children away.
Claudia invited her friend Angie over for an evening of movies and popcorn. Trudy was, of course, invited as well, and the three of them expected to have a relaxing evening. Wait for it, this gets good.
Trudy and Claudia had ordered a strap on from the local Den and were instructed to pick it up that evening. Since Angie was visiting, they invited her along. Angie didn't want to sit alone in Claudia's apartment while the others had a road trip, so of course she accompanied them. It was only a 15 minute journey, and the three of them had an easy time popping in and out of the store. Trudy couldn't wait to get home and try the new strap-on on. She disappeared for a few seconds in the back room and re-emerged wearing it under her jeans. The entire schlong was sticking straight out between the zipper of her jeans. Claudia's dying of laughter, Angie's shocked, and Trudy is getting even more excited. Since Angie's the least impressed, Trudy decides to make the awkwardness even worse.
She humps her.
With a strap on.
After this escapade, Trudy earned herself a platinum medal in the Awkwardland hall of fame. I challenge you to share a story that even comes close to this level of awkward entertainment.
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