Love & Sex

My First Time

Pin it

My First Time - Male, 18 years old, Ithaca NY

Illustration by Thomas Pitilli

Male • 18 years old • Ithaca, NY

Women had never been easy for me. I had a girlfriend one year in high school, but our couplings had always ended the same way, with her hand clamping down on mine, my fingers stopping their exploration one tantalizing inch under the waistband of her panties and still firmly fastened jeans.

I met Sarah the first semester of my freshman year in college, through my new friend Evan. Evan and I shared an interest in hardcore and punk music, and a fashion sense that revolved mostly around those regrettable JNCO jeans and Victory Records T-shirts. Sarah, on the other hand, had a very average-girl look — about five-foot-four, brown shoulder-length hair, a body that was soft but not overweight, always dressed in jeans, sneakers, and simple shirts and sweaters. She was pretty exclusively into Pearl Jam at the time, which Evan and I teased her about in our vain belief that our non-mainstream tastes were far superior.

One night, I'd been hanging out with these Jersey guys who referred to everyone as "brah," as they downed bottles of the Woodchuck they'd been consuming since noon that day. Being straight-edge at the time, I was feeling a failure to connect, so when Evan and Sarah came by, I gladly joined them.

When she left to go to the bathroom, I pulled off the ultra-smooth move of stretching out over the whole couch.

That night I was enjoying myself and feeling expressive — joking, speaking in various accents, being silly. Sarah picked up on my vibe, and pretty soon we were flirting playfully. We all ended up in the lounge of Sarah's dorm watching a bootleg video of the band Earth Crisis, the "singer" screaming about going vegan over relentless, crunching power chords. Sarah said she liked it, even though the recording sounded to me like an industrial vacuum cleaner. (And I was a fan.) She confided that she had a boyfriend back home who was still in high school, but that they had broken up three days before. They were each other's first time, and had been together for three years.

Eventually Evan left to go to bed, and it was just the two of us. I pulled off the ultra-smooth move of stretching out over the whole couch while she left to go to the bathroom, and refusing to move when she returned. The resulting wrestling match quickly dissolved into feverish groping, until an RA found us and kicked us out.

We went back to my room and got back into it over the sounds of my roommate snoring. I was praying that this would be the night I'd finally get to third base, and when I felt the moment was right, I slipped my hand inside her pants. I was ecstatic as she moaned and didn't resist my advance. Having never gotten this far before, I had no idea what I was doing as my fingers moved deeper, through her pubic hair, searching for her vagina. "What are you doing?" she whispered in my ear.

"Um, I'm just…" I mumbled, not wanting to tell her I had never done this before. And then I found it, as my fingers sank into this amazing, warm, wet softness for the first time in my life. By the next morning we had both gone down on each other, but stopped short of intercourse. The next day, Sarah told me it was over, because she was going back to her boyfriend.

I was disappointed, but it turned out that was only the beginning for us. A few days later we were in her room, where she somehow thought that massages would be a fun, platonic activity. This resulted in more oral sex, followed by her crying because she had cheated on her boyfriend. That was the only time she cried, but the hooking up continued unabated for the next two months. It always started the same way, with tentative, "innocent" touching, until we were suddenly naked and desperately working to get each other off, followed by her firm declaration that that was the last time, and she was now committed to her boyfriend.

I had revealed to her that I was a virgin, and one night after starting up with each other in my room, she asked me if I wanted to have sex. I could barely contain myself as I undressed, removed her jeans and panties, and put on a condom. I climbed on top of her, and she reached down and guided me inside of her. I began slowly thrusting into her, afraid I would crush her, until she pulled me down, whispering that it was okay to lie on top of her. I wanted to last as long as possible, but after only a few minutes she said she wanted me to come. Shortly after that I did, and we lay there in the dark for a while not saying anything, her arms around me.

It always started the same way, with tentative, "innocent" touching.

I wanted to be with her, and we were hooking up regularly, but I was never first in her mind or heart, and that led me to finally end our secret romance for good. She was so worried about her boyfriend somehow finding out that she never told any of our friends at school, and so I always had to act like there was nothing going on unless we were behind closed doors.

By the start of the next semester, Sarah had broken up with her boyfriend, gotten heavily into hardcore music, gone straight-edge vegan, and shaved her head. She started picking up guys at shows, and seemed to have a new fling every week. I watched her sudden transformation, uncertain of my role in setting off this new, experimental phase in her life. Looking back, it wasn't everything I wanted at the time, but it was passionate, exciting, frustrating, and fun, and ultimately it's an experience I'm glad I had.