Love & Sex

My First Time: Female, 18, New York

Pin it

Female, 18, New York

The first time I met him, I was strolling through the dorm hall on my first day of university. I must have looked like a lost child because that’s when he approached me and asked if I needed help finding my dorm. He wasn’t drop dead gorgeous, but definitely not a hideous beast either. He was just cute, plain, old Jack. Back then, I was very naïve in the ways of the male race. I had never kissed a boy, let alone had sex with one. I was pretty enough, but never put myself out there in high school, resulting in a boyfriend-less life.

I can remember my attitude being rather negative around people in general, despite my petite, girlish exterior. Jack was a “skater boy,” without the grunge-y, angst-y disposition. He was blonde with shaggy, but surprisingly clean-cut hair. I always thought of him as being asexual (besides a brief sexual relation with a girl from high school,) and I wouldn’t be shocked if he had thought the same of me. We both went through an entire year of college without being in the remotest of relationships.

By our sophomore year, we were inseparable. I didn’t have many friends in high school, and he was the best friend I had ever dreamed of having. About a week before winter vacation, he asked me if I would go to New York with him for his cousin’s wedding. He said he needed a “hot date” to impress his family. I wondered why he had chosen me of all people.

After a beautiful wedding, we sat on a single queen sized bed in a cozy hotel room. The lights were all off besides the dim, blue glow of the television. Jack flipped through channels as I idly stared at the screen. The idea of sleeping in such close proximity to Jack’s shirtless body gave me chills. I didn’t know if it was a sexual chill or an awkward chill. I thought about how I had been a virgin for 18 years and at this rate, would continue to be for a very long time. I felt a sudden impulse to get it over with.

“Jack?” I looked over at his pale, muscular body. “Would you have sex with me if I asked you?”

He widened his eyes and shut off the TV. We sat in the dark and I marinated in shame, wishing I hadn’t asked.

“Now?” his voice nearly cracked.

“Well yeah,” I shrugged in the darkness. “You’ve done it once before, right? You know what to do.”

“I don’t know…” he said.

“Yeah I know, I’m weird and gross and it’s awkward,” I said sheepishly.

“No it’s not that,” he said quickly. “I just don’t think…I’m very good at…you know, sex stuff.”

I burst out laughing as I clicked on the nightstand light. And for some reason I still can’t explain, I threw my arms around him and kissed his lightly freckled cheek.

“Please?” I asked.

“Since you begged,” he said faux-causally, then smiled a warm smile. I loved his smile.

He ran over to his bag and pulled out a condom. I didn’t ask why he had it. Did he know we we’re going to have sex? Was he planning on having sex with someone else in New York? Before I could think anything else, he dropped his boxers to reveal the weirdest thing I had ever seen in my life (I know, I’m a prude.) It was just so long and dangly. He strode over to me and pulled my shirt over my head. I yelped a little as he ripped my bra off and tugged my shorts and underwear off at once. He seemed like he was good at “sex stuff.”

He put both hands on my shoulders.

“Relax,” he said. “And tell me if you don’t want to go further.”

“Let’s go all the way, Jack-y,” I laughed as he started to go down on me. My laughs turned into moans of pleasure and soon enough he was “ready” enough to get inside me. I thought it would be glorious, like all my friends had said. But really, the moment he entered me, I knew it wasn’t going to end with us floating away on a fluffy cloud. I screamed (and not out of pleasure this time,) while he thrust in and out of me. I felt myself get really wet and I figured that I was done. He cringed and put his face against my cheek. In one swift moment he fell beside me. I didn’t even have to ask him to put his arm around me. He squeezed me into his chest and didn’t exchange another word. At that moment, feelings of friendship, trust, and love filled my head. I knew Jack was for me. I knew we loved each other. And I could see us being together for a long time.

The sad thing about Jack and me is that we haven't spoken in five years. He found a girlfriend who, evidently, hated me. She had him whipped and I never could muster enough confidence to win him back. They married right out of college and I have no idea where he is now. She cut me off from him and my only regret is that I didn’t take the leap of faith like I did with the sex. I probably should have asked him to marry me in New York.

Image via icanteachyouhowtodoit