Your First Time Is Awkward

Your first time is awkward.

No matter how much you’ve prepared yourself, you have no idea what you're doing.

I never questioned Caitlin too hard on her first time because mine was most likely just as complicated.

For me, there was Jessica on and off between freshman and sophomore year. The two times we did have sex; I don’t even think I finished.

The first time, I acted like I’d been there before, but really was just worried about not making an ass out of myself. I knew the last guy she’d dated and there was no doubt that the two had hooked up. She assumed I wasn’t a virgin and for some reason I didn’t feel compelled to correct her, let alone be vulnerable and allow her to guide me through the experience. Instead, I lied by omission and pushed forward, enjoying the intrigue of it all, questioning much of it, and fighting off the anxiety of ruining everything with a single awkward move.

I am almost positive that I let her put the condom on. I’d never seen one outside of my high school sex-ed classes. There might’ve been one time where I stole one from the pantry of a friend’s bathroom, but I can’t be certain whether or not I imagined the experience. Memories and fantasies of youth blur together nowadays. If I did take the condom, I no doubt tried it on and used until completion. Imagination or not, the thing worked.

Jessica was my “first time,” if you want to call it that.

Sometimes I don’t count it.

To this day, she has no idea that she was my first.

The most fitting part on the entire story is that I helped build her a loft style bed the day leading up to the encounter. My construction skills are not something to be desired, so while I questioned whether or not I’d be any good during sex, I also worried about the bed crashing to the floor beneath us. It held.

Sex that night ended when she was finished.

All signs led me to believe that she enjoyed it. My reactions during her climax must’ve made her think I was finishing too. In reality, I recall laying back in shock and awe of what was happening before my very eyes.

Girls aren’t the only ones who can fake it.

The second time with Jessica went in similar fashion, except that we were so loaded from a night out on the town that I probably didn’t finish for reasons other than nerves or inexperience.

Now, two years later, I sit next to a girl who I have no doubt made love to countless times and wonder if we are pregnant.