Sex and the Chronically Single Girl


One gal recounts the lessons learned from her sexcapades.

For one of my classes, we had to read Sylvia Plath’s The Bell Jar. The book’s protagonist Esther has an obsessive worldview of sex. At one point Esther says she sees the world divided between people who had sex and those who hadnǯt. To some degree, upon entering college and first discovering my own sexuality, I could relate to Esther’s social dichotomy. I felt as though everyone around me was having hook ups, and I was the one on the sidelines.

I finally got to enter the game of sex January of freshman year when I lost my virginity to a friend after a dorm party. Since them, I have had four other sexual partners. Each of them taught me something about sex and also about myself. I hope these lessons are relatable to others in some capacity.

  1. Losing My Virginity
    The Story:
    I definitely didn’t lose my virginity the way I thought I would. Coming from the south where I had friends who were already married or engaged, I came into college expecting to find my husband. In my dream world, I would lose my virginity to someone who I had been dating for a while and someone with whom I was in love. Instead, I lost it to one of my guy friends after a party. We started fooling around and next thing you know, my metaphorical cherry was popped. In the immediate aftermath, I ran back to my room crying in shock and disappointed in myself. A couple days later, the friend and I exchanged a brief “Are you good?” and moved past the incident.
    The Lesson: Losing one’s virginity is not always a fairytale. Though I probably would not wish my first time on someone else, this sexual experience helped me think more critically about what I wanted out of other sexual experiences. Losing my virginity also helped me discover that what I first needed out of sex was more self-love and confidence.
  2. Sex in a Bathtub
    The Story:
    During the summer before sophomore year, I was working in Cambridge. One night, I went out to a party with some friends who were also around for the summer. We all got obliterated and there was this sexual energy around us. We all started making out with each other, and I ended up having sex with one of the guys at the party in the bathtub as the party was going on. While this definitely wasn’t my finest moment, it was the first time I allowed myself to get caught up in the moment and just go for it.
    The Lesson: Everyone is entitled to a sloppy and passionate sex session. While a bathtub is not an ideal place for sex (cramped spaces equal cramped hips), I let go of my inhibitions (though the alcohol certainly helped.) Sex isn’t always going to take place in a bed, nor will it always be pristine. As long as you are safe (however you define it) and consenting, sex can be wet, slippery, and slightly sudsy.
  3. The Foreign Exchange
    The Story:
    Right after finals ended, I went to a party in Quincy and met this cute British guy visiting a friend for the weekend. We ended up hitting it off (crazy dancing to Beyoncé can really bring people together), and I brought him back to my room. And this is where I forayed into period sex. We were making out and clothes started coming off. He was reaching to my panties when I said I was on my period. He said he didn’t mind and we ended up having ~amazing~ sex. When we were done (read: I was exhausted) and he was getting ready to leave, he asked for a goodbye blowjob. I promptly showed him the door. I put in work without the “thank you” of an orgasm, so I wasn’t going to give him a third one.
    The Lesson: You are not obligated to do anything during sex. While I am a huge believer in reciprocation, if you are not feeling a sex move or the other person has not put in enough time, don’t do it. The other lesson — period sex can feel great, but it will wreck your sheets.
  4. The One Who Got Away
    The Story: About a week after The Foreign Exchange, I hooked up with a guy I knew from the volunteer program I did. I was about to leave campus in two days for an internship in New York, but I was hoping this hookup could turn into something more. However, the next night when I tried to make a repeat of previous evening activities, I was shut down. Yeah, it stung a little bit, but I had the summer to heal (hot finance interns in New York for eye candy).
    The Lesson: Sex is not a tool to get someone to like you. If you want something more serious, you should make that clear from the beginning. The other person can’t guess what is on your mind, especially if it is a first time hook up. While hooking up can be easier, you will end up more disappointed going in thinking that sex will change someone’s mind.
  5. The Bed Warmer
    The Story:
    The time between The One Who Got Away and The Bed Warmer was eight months. In that time span, I had not even kissed someone. So, by the time the Bed Warmer came around, I was practically a starved woman. I went to a party with one of my roommates early junior spring where we ended up getting obliterated to celebrate our new 21-year-old statuses. The first night I brought this guy home, we didn’t have sex. Instead, he spent most of the night going down on me, refusing my offers of reciprocation. He invited me over for a movie the next night and I foolishly brought popcorn to his room. I was yet familiar with the “Netflix and Chill.” We continued to have sex almost weekly for the remainder of the semester. With the Bed Warmer, I tried so many positions and started gaining confidence in my sexual abilities and got comfortable asking for what I wanted out of the sex. Though the Bed Warmer has since graduated, I still think fondly of our sexcapades.
    The Lesson: Communication and experimentation are so important to good sex. I also learned that you can have amazing chemistry with someone without being in a committed relationship. I also emphasize that if you are going to have a consistent hook up buddy, there’s no reason to not get the best sex out of the deal.
  6. ?????
    This year has been a little dry on the sex front, but I am confident that the drought will be over eventually. Each of the sexual experiences I have had taught me a great deal about sex and, most importantly, about myself. I have learned what turns me on and that self-confidence makes all the difference. This is not to say that awkward sex moments won’t happen (sex is particularly squelchy!), but that it is okay to revel in those moments. I am looking forward to recounting lessons about life, love, and sex in future sexcapades as I continue to build self-confidence.

Anonymous hopes to fill in number six by the end of the school year!