Love & Sex

My First Time

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Female • 16 years old • Houston, Texas

The first time I gave in to one of the many teenage boys trying to lay me was my freshman year of high school, at the house of a guy I'd known since fifth grade. His name was Colin, and he was the best friend of the boy I was actually in love with, Chandlar.


Illustration by Thomas Pitilli

Chandlar was my best friend growing up, until one night he decided to kiss me. It was one of those kisses that makes you kick back one knee, like in old-timey movies. I realized that the love of my life had been right in front of me in this short and stocky body. The problem was that I'd always imagined my first love to be tall, dark, and handsome, like the guys on the covers of my mom's romance books. Chandlar happened to be the complete opposite. The politics of high school wouldn't allow someone as pretty and popular as I was to be with someone as unattractive as Chandlar, but I couldn't ignore my feelings for him. So I convinced him that the best thing to do was still kiss and fool around but to keep our romance a secret.

The plan worked well for a couple of months, until a mutual friend asked me to confirm some of the intimate details of one of our makeout sessions. I denied it, headed straight to Chandlar's house to curse him out for blabbing, and called our little romance off. I felt betrayed, so from that day on I refused to speak to him.

A month or two later, I missed my best friend, but I was still too stubborn to talk to him. Around this time, one of Chandlar's close friends, Colin, began pursuing me. I didn't like him at all, but I knew that my being with him would kill Chandlar. Colin was everything that Chandlar wasn't. Tall, handsome, and a natural for any sport he tried. One afternoon at our bus stop, Colin asked me to come to his house with him. I immediately thought, "Hell no!" But then I saw Chandlar and knew he was watching, so I agreed. As we walked in the direction of Colin's house, I looked back and met Chandlar's eyes. We both wanted to say something, but neither of us could find the courage.

In Colin's empty house, I lay naked in his bed, with a rap song on repeat as he tried to seal the deal. I had already made up my mind to do it, but I was as stiff as a twig and as dry as a desert. He was trying his hardest to stuff his penis in me, and getting increasingly frustrated that his efforts weren't yielding results. After he'd tried for about fifteen minutes (I kept looking at the clock on his dresser), he finally pushed through and got the head in. It was the worst pain imaginable and I was instantly angry at all of my slutty friends who'd told me it was going to feel great. At that moment I hopped from under him and rushed to put my clothes on. When he asked me why I was leaving, all I could say was "The Simpsons is coming on." I ran down the stairs, out the door, and all the way back home.

Of course the story he told everyone was sexier than what actually happened, but it gave me the courage to go to my former best friend and tell him everything. It resolved our fight and we were once again best friends. We started dating about a month later. I didn't even bother to deny all the rumors about Colin's supposed seduction of me, because the only person whose opinion of me mattered knew the truth. It wasn't exactly the most magical way to lose my virginity, but I don't regret it — it brought my best friend and future husband back into my life.