Love & Sex

My First Time

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Birds and the Bees

Illustration by Thomas Pitilli

Female • 18 years old • Sarasota, Florida

It was my first semester in college, and I had just started dating someone I thought was my dream guy. He was quiet, spiritual, a year older than me, and ridiculously intelligent. Sometimes he would wear skirts, which I thought was quite charming in its gender-rebelliousness, and he had just shaved his head in a sort of post-freshman-year cleansing. I loved the idea of him.

Almost immediately, he confessed his undying devotion to me, which led me to believe that I, too, was in love. This sentiment later turned out to be a misunderstanding with myself, but I didn't know it at this point. He was my first real boyfriend, and if he said that we were meant to be together forever, I was going to listen.

I don't think he knew how to actually turn a woman on — and neither did I…

I was a virgin and really ignorant about the whole process of sex, but excited about becoming a woman and had optimistic fantasies about how it would happen. I knew what song I would play on my laptop (Bob Marley's "Waiting in Vain"), I knew what underwear I would be wearing (a subtle, lacy, crimson thong), I knew how lofty and spiritually uplifting it would be. I expected my first time with a penis inside of me to instantaneously elevate my soul to a more enlightened state. I would turn into a mini Buddha just by lying there!

The first time he fingered me, I cried a little, not so much from pain but from discomfort. What was this unfamiliar object doing inside of me? Nothing had ever gone in there before — it was uncharted territory, even for my own fingers. I almost felt like I was at the doctor, getting prodded by an instrument while he looked for an abnormality, especially since he didn't even touch or kiss any other part of my body. Although I do think he had good intentions about the whole thing, I don't think he knew how to actually turn a woman on — and neither did I.

I had waited too long to explore myself. I didn't even think of touching myself as an option growing up. I had no idea what an orgasm was, and didn't figure it out until two months after my boyfriend and I had started fucking on a regular basis. That day — the day I gave myself an orgasm — is in my record book as the day I was actually liberated from virginal status. The first time I had intercourse with my boyfriend it was boring, uncomfortable, and surprisingly mundane. I continued to do it solely for his pleasure. The weird part is, I don't even think he realized that I wasn't really getting anything from him sticking his dick inside me, or even thought about asking me how I liked to be touched, or if I had come, or anything. And I was always too scared to ask. I had no idea what was actually supposed to happen during sex, so I just followed suit and kept quiet.

Looking back on it, maybe he was taking advantage of my ignorance. I was a low-maintenance lay. I had pretty much given up. I was convinced that I was someone who just didn't enjoy sex. But after a little while, I started to seriously doubt that (mostly because it felt so unjust!), and I got curious. One night, unable to fall asleep, I googled "clitoris" and "female orgasm." Suddenly I was Columbus finding that uncharted territory, the New World of my body. (Sans slavery, etc.)

But still, I was scared to have an orgasm, maybe due to the constant subconcious sermon of my Roman Catholic upbringing. A little more research and a lot of cautious touching later, a little quiver went through my nether areas, and I knew it had finally happened. In the grand scheme of orgasms, it was tiny, and I certainly didn't turn into a mini Buddha, but I knew that I finally had at least some control over my sexuality — no thanks to my first actual fuck.