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.

When David first tried to contact me, I was on the bus headed to my friend’s house to watch hockey. I ignored his first call, and he proceeded to call me five more times before he decided to leave a message. The next morning he called again, and by the time I’d had my coffee and felt ready to interact with other humans he had called six more times and left two more messages.

Generally when men exhibit this behavior they are either very serious or total flakes; either way I have a strict “call everyone back” policy, even if it’s not right away. David answered the phone right away and informed me in a flustered manner that he was worried he had somehow offended me. I assured him that this was not the case and I had simply been unavailable both times he called. He seemed fairly respectful, if a bit overly anxious, but that’s pretty normal for young clients. Most of the younger ones opt for the company of professional ladies not so much out of desperation as general awkwardness, as well as an (often unfounded) belief that they couldn’t actually get laid without paying.

Once we’d chatted briefly and established that he wanted to see me at the end of the week, I asked David for two provider references in order to ensure as best as possible that he wasn’t a potentially unsafe client–standard screening procedure for most independent providers. He seemed confused, and when I explained it to him he was silent for so long that I thought my phone had dropped the call. “I’ve never done this before,” he said. This was new, but I am nothing, if not resourceful. I was able to come to a compromise with David, and when he was screened to my satisfaction, we pinned down a time for the booking.

I thought everything was in order: I had reserved space in the dungeon I rent from and put the appointment in my calendar. I gave David directions to the somewhat hidden space, and told him I’d call to confirm on the day of the session. However, David did not feels things were in order quite yet. Leading up to the booking, he called me three times in as many days.

The first time was to ask me what denominations of bill I prefer, to which I replied that he could hand me a stack of singles and so long as it was green it didn’t matter to me. The second time was to ask if I cared that I am taller than he is, to which I replied that I am 6’3 in heels, and am therefore taller than pretty much everyone, though I’d be happy to wear flats if he preferred it. I was starting to get annoyed when David called me for a third time, but when I realized the purpose of this call was to ask if I minded that he was a virgin, I was somewhat taken aback. Of course I didn’t mind, and I told him as much, but I wasn’t really sure what to do. Taking someone’s virginity is supposed to be a huge deal, and he had chosen me, of all people, who had never once deflowered anyone.

As the appointment drew closer I started to freak out more and more. I was going to be the measuring stick by which all other women would be judged. This was huge. I arrived at the space I use to see clients a full hour early so I’d have ample time to get dressed and get the room ready. If I was destroying a virginity, it was going to be perfect.

Finally, David arrived. He had some trouble finding the house, but I managed to steer him in the right direction, and when I let him in the door I was struck by how very small he really was. At 5’2, he barely reached my shoulder even though I’d chosen my thinnest pair of flats for the occasion. Before he could even get his coat off he reached up, and shoved his tongue in my mouth in one of the worst kisses I have ever experienced. I was able to extricate myself quickly, told him to remove his shoes, took his coat, and suggested we “get the boring part out of the way”–my euphemistic way of demanding my fee. Once he handed me the envelope I led him to the room we would be using, excused myself, counted the money, and stashed it in my purse.

When I returned to the room, David was already naked and standing in the middle of the floor, his clothes in a neat pile at his feet. I put on my one hour timer playlist, disrobed and sat down. I patted the bed beside me, ready to have the kind of sex-positive sex talk I assumed was par-for-the-course in this sort of situation. David seemed to have other ideas, though. The minute he sat down, he grabbed my head again and started in on another agonizingly awful kiss. I did my best to steer his surprisingly strong and unyielding tongue, but had very limited success. Finally he broke off the most awkward make out session of my life to ask if we would use condoms when we had sex. I assured him that we absolutely would, and if he tried to do anything else, I’d ring his neck. I then used his question as a segue to pull out the condoms and lube.

Once I got the condom on, I decided the best course of action would probably be a blowjob. According to both clients and personal partners, I’m pretty awesome at blowjobs and I’m very proud of my skills. However, my lips had barely touched the tip of his dick before he told me it was my turn. I’ve talked before about how much I hate oral, especially client oral, but this actually wasn’t terrible so much as it was just strange. David’s idea of oral seemed to be licking around the area of my pubic bone for a few minutes, and then stopping. I was so confused, I hadn’t even realized I was supposed to actually pretend to enjoy it; I may have unintentionally given him the correct impression that he was really doing this whole cunt licking thing super, super wrong.

I had no idea what to do. He hadn’t explicitly stated that he wanted me to give him directions, so I decided to err on the side of caution and just not say anything when he did ridiculous things like putting his finger in my vagina and turning it gently from side to side. I decided to move into actual intercourse and just hoped he would stay true to the virgin stereotype and come quickly, but I had also heard stories of virgins unable to get off at all because of nerves.

Once he gave up ramming helplessly at my pubic bone and stuck his dick in me, he looked truly surprised. “It’s in!” he exclaimed joyfully before jackrabbiting away for maybe two minutes while I pretended to enjoy myself. When he came I showed him how to hold the end of the condom when he pulled out, lest it get caught or stuck, and hoped he wouldn’t want to talk much. He didn’t. After a brief recovery period, David got up, refused my offers of a shower, dressed himself, and asked me to show him out. That was it, that was the end: he was no longer a virgin.

While I straightened up the room and changed the sheets, I wondered if I’d done a good job. David certainly wasn’t the most attractive young man and would most likely have trouble getting laid for free, but in the event that he was able to find a girl willing to overlook his diminutive height, lazy eye, and disconcertingly boyish physique, she wouldn’t exactly be in for throes of ecstasy. I felt a pang of responsibility for releasing a sexual disaster upon the world. Was there a nice way to have given him some better pointers? He seemed so eager and enthusiastic, and I am not good at giving directions or criticism in a gentle manner.

After some thought I decided it didn’t matter, though. A one-time dose of directions weren’t going to teach him how to be good at sex, but a pleasant, no-pressure experience would definitely boost his confidence, which might help him to find a civilian woman who could to teach him how to actually please her. Either way, he had gotten rid of his virginity and I’d both gotten paid…and finally realized what I’d been “missing” in high school. We both won.