Harlotry: The Story Of How I Deflowered My First Virgin, With All The Awkwardly Gory Details

Harlotry: The Story Of How I Deflowered My First Virgin

Cate is something of a renaissance sex worker and has held numerous interesting jobs in the adult industry. Each week, she shares her stories in Harlotry.

In the six years I’ve been a sex worker I have, to my knowledge, deflowered exactly one man.

It is not as though my career is unfamiliar to firsts: when I was a stripper I gave several guys their first lap dances, most notably a very small metalhead celebrating his twenty first birthday. I sold him on an hour in the champagne room, and within fifteen minutes he had thrown up all his birthday drinks on my shoes and was kicked out. An untold number of clients have come to me to have their first strap-on experience, and even more have come to me to try various other fetishes for the first time. But up until very recently, no one had ever come to me to lose their virginity in a more traditional sense.

I never really did the whole awkward high school fumbling thing. There was no “just the tip!” begging, no messing around with weird Cosmo-influenced blowjob techniques. I learned how to give a blowjob by watching gay porn with my friend while we practiced on popsicles. And the one time a guy mistook my youth for inexperience or unwillingness and asked if he could put in “just the tip,” I laughed in his face and asked if that was really all he was offering me.

In fact, I’ve never had recreational sex with anyone under the age of twenty. When I was a teenager I couldn’t understand what I was supposed to see in boys my age. I instinctively knew that while girls my age were fine and dandy, teenage boys didn’t know what they were doing and teaching them would be far more trouble than it was worth. The closest thing to a high school sweetheart I ever had was the twenty-year-old I selected to rid me of the annoying burden of virginity and proceeded to have casual sex with for almost a year afterwards.

I guess a lot of people assume that once men get to a certain age, they seek out the company of prostitutes like myself in order to get rid of their virginity. However, in my experience this hasn’t really been the case, and none of my close sex worker friends have tons of stories about virgins, either. I know it happens–I’ve spoken to women on the internet who have taken virginities. Still, I was thrown for a loop when I recently had a client whose first experience with sex wound up being with me.

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    • Kaitlin Reilly

      I’m so happy that Harlotry keeps using photos from some of my favorite movies (the Rules of Attraction and Closer both have a very special place in my heart.)

      • http://toyboxkiller.tumblr.com/ Cathryn Berarobitch

        All the credit for that goes to Sam! I’ve only chosen one photo in all the time I’ve been writing this column, and that was the chocolate froyo for my brown shower post.

      • Samantha Escobar


      • http://toyboxkiller.tumblr.com/ Cathryn Berarobitch

        I support and endorse your photo choices 100%.

      • http://toyboxkiller.tumblr.com/ Cathryn Berarobitch

        No wait, that’s two. Because I also chose the picture of GOB Bluth and Franklin for when I was booking escorts on the phone.

      • Samantha Escobar

        I’m obsessed with both of those movies and their book/play forms, especially Rules of Attraction. I’m glad somebody else digs ‘em :D

      • Kaitlin Reilly

        Me too! Rules of Attraction is one of my favorite novels ever.

    • Amanda

      My boyfriend is 5’1″ & I’m 5’5″ – I’ve never minded it, & he’s quite amazing in bed! Great story, I love your posts!

      • http://toyboxkiller.tumblr.com/ Cathryn Berarobitch

        I have a weird prejudice against short men. They can be fine as friends, but I find that when I date them they get pretty weird about my shoe choices pretty quickly, and when I refuse to only ever wear flats their insecurities start spreading elsewhere. So I’ve adopted a “must be this tall to ride” policy of six feet or taller.

    • http://toyboxkiller.tumblr.com/ Cathryn Berarobitch

      Small correction here, I’ve never had recreational sex with any MAN under the age of twenty.

    • Miss_Em

      The last guy I dated, who was 35, was a virgin. I’m 37, and have 20 years of practice under my belt, so it was not a happy moment when I found this out, one month into dating (it’s the longest I’ve ever waited to have sex with a man). I had already surmised as much, given the fact that I had been coaching him on the kissing ever since our first make-out session. I told him that we could have sex when the kissing got good.

      Even during make-out sessions on the bed, I had to tell him to lay on top of me. I felt like a mama-bird teaching the baby bird to fly. I definitely think this all contributed to the demise of any potential chemistry, but I felt bad having dangled sex in front of this man who had been so sweet, loving and attentive all this time. Well, it took a month, but the kissing definitely improved.

      The sex was awkward – his penis was resting up along my vagina for a long time before he realized it wasn’t inside. i also didn’t want to keep pointing out every possible mistake he was making, so I was just being kind of receptive and observing. Another time, when he was inside me in doggie-style, he was so close to me that he couldn’t really thrust, and I had to tell him to back up a little and push and pull, in and out.

      He needs so much experience, and I was happy to help him get some, but I could not stay in that relationship and be happy, no matter how sweet and attentive he is.