First Time For Everything: Hitting The Big O

In the spirit of Columbus, Magellan and Lewis and Clark, I spent my teenage years as a fearless explorer of uncharted carnal terrain, reporting back to my tight-knit group of girlfriends with play-by-plays and handy tips from my randy sexual exploits. I was the first in my high school crew of gals to do pretty much everything: kiss a boy, get felt up, get naked, get fingered (in a movie theater), receive oral sex, give oral sex, and finally, have sex (on the floor of my high school boyfriend’s parents’ basement). A new world of experiences was opening up, and I took on my role as trailblazer with fervor, drive and anthropological scrutiny. That first night on the basement floor, I remember thinking to myself, Wow, the cavemen did this!

For the next few weeks, we worked on it, and for the first time I had an experience of sexuality that was based on my own physical desire. We were rounding all the bases, but it wasn’t so I could brag to my friends or spite the Virgin Mary. It was so I could feel these mystical sensations of tension and release, these chill-inducing caresses of touch and tongue, these moments of passion and mindlessness.

Related: Girl Talk: Why Do Girls Get Depressed After Losing Their Virginity?

While my adventurous nature was a point of pride, the exciting complexity of feeling that sex evoked — in all the forms I had discovered, so far! — also helped to stave off the intense boredom I was feeling with everyday life in the suburbs. I was rebelling against my Catholic parents, and the tasting of all this forbidden fruit while supposedly “sleeping over at Jessica’s house” felt both empowering and iconoclastic. I was turned on by everything sex had to offer.

Except, it turns out, I wasn’t actually turned on.

At 16 years old, I’d never had an orgasm. In my life. In fact, I didn’t even know what an orgasm was. If my friend Eliza hadn’t happened to mention the topic in the school cafeteria on a fateful Tuesday, I might have lived out my days pioneering the sexual badlands without ever, um, coming into my own. I’d slept through biology class. Sex Ed at The Holy Family School never really happened. The Internet hadn’t been invented until I was old enough to be giving my first blow job. And so I had grown up and grown into my sexuality with no one spelling it out for me. I knew that guys “came” (duh!), but even though it sure felt good when my boyfriend went down on me, it had never occurred to me that there was — or should be — an equivalent response for women.

But there sat Eliza, peeling an orange and making an offhand reference to an “orgasm” she had. I somehow knew exactly what she meant, even though I never thought it through before that moment. I assumed it had to have been in my repertoire, at some point … right?

Though internally panicking, I managed to throw down, “An orgasm? I’ve done that. I’ve had that. I think.”

“If you have to think about it, then you haven’t,” Eliza replied.

My girlfriends nodded earnestly in agreement. For the first time on the subject of sex, I was rendered speechless. Not only was I not the first, it looked like I was dead last.

“You’ve never had an orgasm?!” my boyfriend said, with apparent shock, confusion, and imploding ego when I told him about my little discovery.

We’d been having sex for months, and evidently, I had been faking it — without realizing that there was something to fake.

Related: Why Women Really Fake Orgasms

Admirably, my boyfriend rallied, pushed me onto the bed, and said, “For starters, you have to relax.”

For the next few weeks, we worked on it, and for the first time I had an experience of sexuality that was based on my own physical desire. We were rounding all the bases, but it wasn’t so I could brag to my friends or spite the Virgin Mary. It was so I could feel these mystical sensations of tension and release, these chill-inducing caresses of touch and tongue, these moments of passion and mindlessness.

Any time I felt self-conscious, I would tell my boyfriend about my insecurity, and he would tell me I was beautiful. If I had a thought that felt “dirty,” I would say it out loud, and find myself — and my boyfriend — more turned on than ever. Real fearlessness, I found out, was expressing yourself through sex, not just having lots of it. This new frontier of eroticism was more expansive, beautiful and thrilling than I’d ever thought was possible.

One afternoon, as we lay in his bed and he slowly, languidly went down on me, I truly let myself go. I got out of my head by imagining that my brain was actually down … well, you know where (I slept through Bio, remember?!) I let myself feel every chill and sensation. I let my body churn in slowly building intensity.

And it happened. I came!

Related: 5 Things We Didn’t Know About Our Orgasms

But I didn’t want to think about it. I just wanted to lie there, relish it and then make my boyfriend go back for more. As he went down there for round two, and I began to understand how he was playing with all the different anatomical pieces, I had — like Newton, Einstein, and Watson and Crick — what seemed to be a revolutionary idea: I’ll bet I could do this for myself.

Of course, I wasn’t the first of my girlfriends to masturbate either. Twelve years (and countless orgasms) later, I haven’t been the first of my girlfriends to do a LOT of sexual things. But sex is not a competition. The girl who comes first isn’t necessarily the girl having the most fun.

Rebecca Wiegand is co-creator (with BFF Jessica Massa) of multimedia project WTF Is Up With My Love Life?! where she blogs about modern womanhood, love poetry and her f**ked up love life.

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