I lost my virginity in ugly underwear. Con’t…

Where did I leave off in yesterday’s Weekly Writing Challenge post? Ah yes, eating Oreos and watching vampire flicks wayyy before it was cool for teen girls to watch vampire flicks.

The day after Oreo-Fest 2000, I had migrated from Alyssa’s couch to my family’s couch. We were still on winter break, so I was busy being bored. Then, the phone call came that changed my life. It was my friend Ben calling to see if I wanted to ride with him to our friend Brandon’s basketball game. Yes. I had been friends with both guys forever, and harbored a long-time crush on Brandon.

We go to the game, we watch the game. That’s the boring part. But the ride home…

Let me first paint a picture of Ben’s car for you. A mid-90s, electric blue, 2-door Chevy Cavalier. The inside is a mess. Empty cigarette packs, rolling papers, soda bottles and Burger King wrappers littered the front and back. I thought I was in heaven. Oh right, and there’s no rear view mirror. Hmm.

So we are on the way home from the game, about an hour ride, and the guys an I are chain-smoking Newports and blasting Nelly’s Country Grammar. The guys were also smoking weed, but not me. They were dropping me off at home and my mom and dad were the type of parents that would not find it amusing if their 16 year old daughter came home high after spending the day with the town “hoodlums,” as my mom called them.

I was sitting in the back seat, and Brandon up front with Ben. I’m not quite sure what happened, but at some point in our conversation, I said “fuck you” to Brandon. He turned around.

“You would never,” he said.

Wanting to be badass and flirtatious, I responded, “How do you know? You’ve never tried.”

At this point Ben entered the conversation. “Yea right, B. You would never fuck Brandon.” They laughed, and I knew it was because they knew how naive, inexperienced, and sheltered I had been. This irritated the shit out of me.

The back and forth continued for a minute until Ben finally said, “Ok. Prove it. Have sex with Brandon right now.”

So I did.

Ben pulled the car over and Brandon hopped into the back seat with me. Then Ben started driving again. Yes, ladies and gentlemen, I lost my virginity in the back seat of a 2 door car while someone else was driving. Classy, I know. I don’t remember how it felt physically. I do remember telling Brandon I didn’t know what I was doing, and he re-assured me and told me to “…move around. Don’t just lay there like a dead fish and you’ll be fine.” I also remember my underwear. They were too big, and too high-cut, and an ugly bright purple color. I was mortified when Brandon helped me wriggle out of my jeans and saw them. There was no way to hide them – we were in the back seat of a 2 door car!

I am convinced to this day that it was because of my ugly underwear that I never had sex with Brandon again. Unfortunately, at the time I was so devastated that I had been a one-ride stand for Brandon, that all I could do was blame myself. 14 years later though, I know better. It wasn’t me. It was those God damned underwear.

Tomorrow:
Those Underwear: What Brandon was REALLY Thinking

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