Love & Sex

My First Time: Female, 16, Toronto

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Female, 16, Toronto

I was sixteen, he was seventeen. We had been dating long-distance (his town was about an hour drive away from my city) for a couple of months at the beginning of the school year. We would meet up during the weekends at a mall in a town in between, then hang out around a nearby Japanese zen garden, making out and feeling each other up and down until my mom came to pick me up and he had to drive back home.

During either our first or second date, he had performed oral sex for the first time, and I was a first-time recipient. We found a clearing in the bushes where he laid down his hoodie and I went down on top of it. That was the most fun I'd had under the still-high September sun.

When we had chatted about it over IM, he let me know that if I wanted him to do that again, I should shave completely. I wasn’t unruly or anything, just neatly trim, but he preferred completely bald. Those were fair terms, I thought.

Unfortunately, this chat history was saved, my compliance recorded. (This was before I learned to put a password on everything.) My mother discovered the dialogue, and in her frenzied, recently laid-off state, she went mental. She thought this meant I would end up just like her: a single mother with a kid who had the uncanny ability to disappoint her at the most inopportune times. She forbade me to see him again, to prevent my (in her mind) otherwise inevitable unwanted pregnancy, which she was now in no position to support financially.

But our puppy love was stronger than that. We still talked for hours each day, trying to figure out how to get him back on my mother’s good side until we came up with our brilliant plan: have a Meet the Parent dinner so my mom could see that our love was real, that our oral lovemaking wasn’t in vain.

He continued to air-dry his undies until it was time to head to the restaurant to greet my mother.

She had just gotten a lead on a new job, and consequently was feeling less like we’d end up like every other broken welfare family out there, and more like my boyfriend could be a decent human being who cared about me. It was a date.

Mid-day that Saturday, she dropped me off at the suburban shopping center (as per usual) with the plan to reconnect with us in the evening after our day of window-shopping and her day at her new office near the mall. My boyfriend and I did a lap or so around the mall before heading to the zen garden around sunset.

With the days ending earlier, and the cold Canadian nights coming earlier than preferable, we'd had the foresight to pack a comforter; laying down a hoodie would no longer suffice. It was nice, nuzzling in the bushes under the stars. Making out under the stars. Groping each other under the stars. Having him push his pants down enough to take his dick out and slip it in me for a pump and a half before an emergency pullout and ejaculation in his boxers, under the stars.

"Oh shit," he said.

He looked around for materials to clean up the mess, and opted to use the comforter to sponge his soiled silk skivvies. “We’re meeting my mom in an hour,” I offered.

He continued to air-dry his undies until it was time to head to the restaurant to greet my mother. He went to the restroom before shaking her hand. While our twilight activities had been over in a flash, time flowed viscously during dinner. Over the course of our courses, my boyfriend managed to keep a straight face while being grilled about his aspirations of being a rock star, playing hockey, his family, and everything else a mother would want to know about the boy who she knew to be orally corrupting her little girl.

When we finally finished dessert and settled the tab, my mom seemed content with my boyfriend's performance during the interview. As we said goodbye, she even gave him a hug. I imagine if she knew my first time had happened just moments earlier, their meeting would have ended in more of a stranglehold.