We’re looking for stories about the first time you had sex. Email with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
I was a bit of a late bloomer – but I was definitely never a prude. I started masturbating at five years old. All my Barbies wanted to flaunt off their shiny beige cleavage for Ken and play time usually involved them rubbing against each other on my family room carpet. I scoured my parent’s extensive book collection for any sex scene, whether it was with 19th century lovers or scaly lizard-like creatures, lapping at humans (seriously – that is in a book). If I stayed up late enough, sometimes I’d get a glimpse of Showcase’s Red Shoe Diaries, and would use those graphic scenes to bolster my sexual imagination for as long as I could.
I met Jon in my second year of university. I was late for the first day of my 8:30 am British history class and the only seat was at the front of the room, right beside. I was wearing tight jeans and he sat up straighter when I settled in to the seat. The first chance we had, he started talking to me. He was funny and I was shy, and after a few weeks of weekly classes, we were chatting online and emailing each other. The holidays came and went and I’d spent my break partying and making out with strangers, seemingly preparing myself for the inevitable with Jon.
A few weeks into second semester, I started going to Jon’s house to hang out. We’d eat, watch TV, talk, and talk more. I’d drive home in the icy January early morning, excited, wondering what was going to happen next. One night, close to when I had to go home, he kissed me, and the next minute, I was on top of him, his hands rubbing my corduroy-covered ass. That night I drove home, near delirious, my clothes smelling like him, and my panties completely soaked. Busy with school, we didn’t see each other constantly, but spent each Thursday morning rubbing our legs against each other in class, and the occasional evening in his small bedroom, hands wandering, my own not really sure what to do.
In February, he invited me to meet his friends at a small party and stay over at his place. Terrified, I ate chocolate-covered coffee beans for energy, followed by way too many rum and cokes. In his bedroom that night, he undressed me. I drunkenly insisted I keep my (duck-covered) socks on and then told him I was a virgin. He was surprised and, I think, disappointed. He slid inside me slowly but we were both too drunk for it to go any further. The next morning, he told me he only had the one condom, so we had to look for the one we used the night before. Finding it on the floor behind his bed, he slid it on and we resumed what we had started. It hurt, but it was quick. A quick trip to the bathroom afterwards showed me I was bleeding. Later on, he asked me to give him a blow job, and taking his above-average penis in my mouth, I didn’t know what to do with my teeth. Wincing, he asked me to stop. That night I showed my friends how big his dick was over coffee and donuts.
We dated for a few months after that, the sex becoming more natural to me. I didn’t know what we were for a long time, until I overheard him tell his grandma I was his girlfriend. He broke up with me through email in July, telling me he didn’t want anything serious, and I cried for a week.