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My First Time
Illustration by Thomas Pitilli
Female • 18 • Singapore
At eighteen, waiting for my results to get into university, I found a waitressing job at an airy European bar-and-restaurant in a huge Chinese shophouse in the central business district. It's in an area equivalent to New York's Wall Street, I imagine. The bar was where the worldly-wise (or so it seemed then) and well-heeled corporate crowd gathered after six p.m. They came from all over besides Singapore — Australia, the U.K., the U.S., India, and the Middle East. I was thrilled to work at a bar (and such a cosmopolitan one!) for the first time. The experienced bartender, a Singaporean Indian boy four years my senior, was outspoken, funny and brash, but had a soft smile for me. I responded naturally, almost reflexively, to him, grinning and chatting every time we shared a working shift.
He summoned the courage to ask me out for dinner to a fancy restaurant. After two dates, we started to kiss. We couldn't stop. We kissed for hours in gardens, beaches, and behind malls; anywhere that afforded us privacy. We both lived with our own parents (as is common in Singapore). He quickly became my first boyfriend. Later, my parents would be horrified to find out that their decent Chinese daughter dated outside of her ethnicity, to a dark-skinned boy. (This non-politically-correct view was common among Chinese Singaporeans ten years ago.)
I'd been reading online teenage sex-advice forums since I was fourteen, and I always thought I would discuss in a mature way how and when I was to have sex for the first time. I didn't recognize that him daring me, three months after we met, on the phone, to cab over at midnight, was an invitation to do the dirty. I sneaked over, rosy-cheeked and giddy with the excitement of a first relationship.
His parents were asleep. Candles were lit, the navy sheets smelled fresh, and we were making out for the first time in complete privacy. We were giggling naked and rolling around. I still didn't have sex in mind — I thought body-kissing and fingering was fun enough for the moment. He had different ideas about what to do with the naked female frolicking in his bed. In Judy Blume, on the online forums, and on television, guys asked before they went in; it just didn't occur to me that my boyfriend wouldn't ask me before sticking himself into me.
So he had me propped up against the wall, legs open and thighs up, and he was fingering me, with one, then two fingers, and then I thought he was pressing the front of his bent wrist against my vagina, but then I realised it wasn't his wrist, because one of his hands was holding my calf, and the other was pushing against my thigh. So I reached to touch my opening, but it was blocked by his cock. I thought, "Wait a minute. His cock is in me!?" I was confused, because it felt strangely like it was still outside, pressing to get in. (Hymen block?) Imagine trying to swallow something that wouldn't go down. For a minute, he backed off and started slapping his cock crudely to maintain his erection, then licked his fingers to lubricate me, then tried to penetrate me again.
"Hey, stop! Stop! Talk to me," I pleaded to his in-his-own-ecstatic-moment face, my mind whirling with the conflict of reality versus "What Was Supposed to Be." "Aren't you supposed to ask me if I'm ready emotionally and physically?" I threw words I had read online to him, my anchors for the moment.
He started blankly at me. "Er, no. You seemed ready." He was so matter-of-fact that I burst into tears and laughter at the same time. I had just lost my virginity, to an utterly insensitive guy I was unfortunately starting to care for. And in a scary position too. Then we tried it again, after he asked me nicely to get on top of him. I didn't see why not, since we had already kind of done it, without a heart-to-heart session. It felt odd, but was no big deal really, like jamming something into my ear. And then it went all the way in. It burned like a scab was being scratched off inside me, but not too painfully. I tried to move up and down, reading enjoyment on his face, and feeling jealous I didn't feel the same. But by the third time he penetrated me, it did feel more like pleasure, and less like pain.
"You have weird, fairy-tale ideas about sex," he said when it was all over, as I stared at the stain on the navy-blue sheet, trying to determine the colour of the wet.
His trademark sensitivity was hardly comforting. I had to get over my mortification by myself.
The relationship lasted four years, to my parents' dismay (and then barely-disguised delight when it ended). In those four years, I learnt, amongst other things, about boundaries and expectations and boyfriend-selection. And most importantly, how to self-pleasure. My first real orgasm with someone arrived with my second sex partner, but that's a whole different story.We're looking for stories about the first time you had sex. Email email@example.com 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.