Love & Sex

My First Time: Female, 21, California

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By sheer chance, Jack and I both ended up in Shanghai that summer.

Female, 21, California

I was a late bloomer in all senses of the word. My first kiss happened at a Halloween party when I was 18 and my first boyfriend a few months later. Jack was a very charming boy I met at a college formal. Both of our dates became too drunk to function. He saw me standing by myself and asked me to dance. I still remember how nice it felt to twirl into his arms. We ended up talking for the rest of the night and on the whole bus ride back to campus. For a month and a half, we were inseparable. I had a lot of firsts that spring. I was eager to experiment with him and learned how to give a decent blow job through trial and error. The first time he went down on me was terrible. Jack was 22 and I was his fourth girlfriend. He respected that I wasn’t ready for sex, but he didn’t like it. Every time we were in bed he pressed his hard dick into me and whispered, “Let’s do it.” So in retrospect, he wasn’t always a gentleman. We spent the summer Skyping from far off places and trying to maintain the fire that we saw in each other.

That summer I thought seriously about losing my virginity to him. I went back and forth. I spoke to my best friend, who was in a similar predicament, at length about the pros and cons and still couldn’t make a decision. In retrospect, I didn’t like the way Jack controlled so many aspects of our relationship and I didn’t want sex to be something he decided we would do.

When we got back to school in the fall, we were in completely different places. He wanted me to be his serious girlfriend and the stability that came with that. I went into the new year excited to not feel like a freshman. We soon fell into familiar sexual habits, aka dry humping and oral sex. Now that we were a few minutes walking distance away from each other, I felt the sexual desires I did last spring. Every time we ended up in bed, our make out sessions became more intense and I won’t deny that I loved feeling his hard-on through my jeans. One night when we were dry humping rather intensely he suddenly pulled his dick out and started rubbing it against my crotch. In that moment, I wanted it very badly. As he was undoing my pants, something didn’t feel right and I stopped him. He got so angry at me that I had to leave. As I walked home, feeling guilty and hurt, I pulled myself out of the situation and I realized that if I lost my virginity to him to make him happy, I would always resent him. The following month, right before I was going to visit his family for Thanksgiving, we broke up. It was mutual and painful, but I felt relieved.

At the age of 21, almost two years to the date after Jack and I first met, I finally had sex. By sheer chance, Jack and I both ended up in Shanghai that summer. I hadn’t spoken to him since we had broken up. After posting a Facebook status about my travel plans, he messaged me. We met up a few weeks into my trip and chatted all night at a Mexican restaurant. At the end of the night, I was about to get into a taxi when he said, “Next time you’ll have to come see my view.” I raised my eyebrows, kissed him on a cheek, and said goodbye. On the way home, I felt this urge. I think I was finally ready.

Two weeks later, we met up for drinks at one of his favorite bars near his apartment. We talked for awhile, though the conversation wasn’t as lively as the last time. I was nervous and he was distracted. After our third bar stop, he asked how I was feeling. I said, “How great is this view of yours?” The next thing I knew, I was pressed up against the glass window of his apartment, really enjoying the view. He kissed my neck and all down my back. When we made it to the bed, I asked him if he had a condom and this time he raised his eyebrows. I didn’t tell him that it was my first time and he didn’t ask.

The experience was mediocre. He came twice and I didn’t come at all. Jack was never observant when it came to my pleasure. When I woke up the next morning, I felt different. The physical act didn’t change me, but making my own decision did. He tried to get some morning action and I rebuffed his attempts. My last few weeks in the city were Jack-free and full of new experiences. Now that I think back, my first time felt good because it was my decision and no one else’s.

Image via Flickr.