Sex and self esteem… it’s complicated

I have a complicated history with sex. I’ve engaged in it, have sought it out, and have talked about it at length with friends, but my relationship with it is shaky. I wish I could say I was like Samantha Jones, and had sex “like a man”. I even wish I could say I thought of sex as being very special, and only worth sharing with those you love. I wish I knew where I even stood on the matter.

I’ve had sex exactly three times, with three different men, on three different occasions. This is embarrassing for me to admit because I am a woman of a certain age (26) and feel there are, admittedly bogus, standards I feel I need to adhere to. I didn’t lose my v-card until I was 22 and in college. It wasn’t a romantic, life changing event with a man I loved. It was a choice I made to take myself out of the virginity pool. In fact, it was unsafe sex and resulted in my roommate’s boyfriend driving me to the drugstore to get Plan B. And while I was happy to have turned on the “sexually active” switch, the encounter made me feel dirty and unworthy. The guy – who I had met maybe a few days prior – didn’t even kiss me. It was essentially an instructional activity, with him informing me of the “right” things to do. He inadvertently insulted me, and made me feel upsettingly green, but I felt no remorse about my choice because I had finally become “normal”.

The following two times I had sex were more of the same: drunken, deliberate choices to add notches to my belt. The second guy was a complete stranger who I rationalized was safe because he was a student at a religious university, and the third was I guy I vaguely knew from my hometown. Both on the surface made me feel more experienced and confident, but neither was enjoyable or satisfying in any way.

If you look at your female friends, you may notice that they fit pretty neatly into categories. You have the friends that are serially monogamous, who have perhaps had fewer sexual partners than others but have had lots of sexual experience. Then there are the friends who are very connected to their sexuality, who have had lots of partners and enjoy sex more than almost anything. Alternatively, you may have your few remaining virgin friends, who haven’t been in positions where they felt comfortable having sex. If these three categories are circles of a Venn diagram, I’m an outlier. Sure, I’ve technically had sex, but I don’t feel positive about any of my encounters. None of them felt respectful, sexually stimulating, or even worth noting. They simply became stories, ones that I happily retell with a smile at happy hours.

I am completely at odds with my sexuality. Perhaps it’s because of inexperience, or perhaps it’s because I have incredibly low self esteem. I envy the women who unabashedly flirt with men they find attractive, or even the ones who actually accept the date invitations of men on Tinder. It’s a self-fulfilling prophecy: I assume no one will be interested, so no one really is. Sex is such a large part of so many women’s lives, and there’s no real reason it shouldn’t be a part of mine. I’m embarrassed that it’s not.

This story doesn’t have a happy ending yet, but I look forward to a future where I feel sexually confident. I, too, want to discuss dick size at brunch, rather than simply laughing at other people’s comments because I feel I can’t contribute. But most of all, I want to feel beautiful, and worthy of someone’s love or interest. I think that will happen, but maybe not until I can look in the mirror and feel content. It’s like they say, No one will ever want to fuck you until you think you’re fuckable.

Sarah Kathryn is a New York based freelance writer (among other things) who wants you all to get down with your bad selves.

Photo credit: Fritz Luckhardt via Creative Commons


  1. Candive on August 4, 2014 at 5:16 am

    Sarah, It will happen. I had a similar experience, wishing to throw away my virginity in exchange for "experience." For me, my third man because I got to know him; he blew my mind. Don’t just look for a lay, but wait for at least compatible companionship before foraying into the sexual field again.

  2. Romanna Anna Nova on December 16, 2014 at 10:22 am

    I made pretty much the same experience, except that by the age of 26 I managed to collect about 30 pieces of ‘experience’, and now I am 32 and I see the whole thing very differently.
    Sarah, don’t you ever believe that the problem is with you or your beliefs. You are perfectly fine, it’s just that you haven’t yet met a good match of a partner for you, your body is telling you this. Meanwhile you have adopted the only mass-produced way of sensual engagement you know of, which brought you further away from the wisdom of your body and your truth. I know that, because had I waited for the right man, I would be a virgin to date, and my body wouldn’t eventually bring me to a halt and made it clear that I ought to listen, even for the price of being on my own.

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