The Juicy Tale of Naughty Nurse Meets Pirate Wench

Live-blogging an afternoon cybersex tryst on OkCupid

A pirate wench walks into a sexy nurse’s office and asks, “Could you examine me? I think there’s something wrong with my heart.”

The nurse, in her short white skirt, answers, “Of course, but so I can listen better, I’ll need you to remove your corset.”

Surely this is the beginning of some raunchy joke—the punchline of which involves “plunder” and rubber gloves, no doubt—or maybe an episode of crossover porn. Whatever the case, no one could actually be getting off to this scenario of a pirate and a nurse in an exam room, right? What about when the nurse pinches the wench’s nipples to test for illnesses that could be caught on the high seas?

Well, it’s 4:30 in the afternoon and I am that pirate wench. Life can’t be too bad though, because apparently I own a corset—and presumably a tri-corner hat. Of course, I’m role-playing in online chat. My partner, a forty-something user from California playing hooky from work, is stroking his cock while he instructs me to stick out my tongue and say “Ah.” I don’t have the heart to tell him: for me this is work. I do however muster the sass to suggest that the real disease I suffer from is tasting too sweet, and would he/she please perform that age old medical test of diagnosis through licking.

This all started last month when I interviewed Sam Yagan, the co-founder of OkCupid, the self-declared dating site of hipsters and polyamorous people. Being a little bit of both, I wondered if the site could also be a happy home for cybersex. According to Yagan, not only would it be easy to find partners for online romps, there were already a health helping of OkCupid doing it digital.

Not all the wenchy blame falls on Yagan though. I also point the finger at Audacia Ray, fellow sex writer and head of the Voice blog Naked City. I recently read her book Naked on the Internet—a great intro to a lot of the topics discussed in Click Me. In it, she talks about the culture of sex blogging, which chronicles the juicier details of a writer’s sex life. I liked the idea of doing something similar for my cybersex encounters—making a record of all the faux-mating I do for “research”—so, for fresh material (i.e. a roll in the online grass) I decided to test out Yagan’s claims about OkCupid.

Which is why, on a Friday afternoon, I was roaming a dating site like a perv. Here, in good bloggerly fashion, are the minute-by-minute details of my misadventure.

1:00. I update my meager existing profile, trying to look friendly—and only mildly in the “I want to stick my tongue down your throat way.” I make sure to include cybersex as one of my interests, since this was a Yagan tip for finding partners.

1:30. I run a search of the word “cybersex,” hoping to find other people who think internet sex is the cat’s pajamas (insert “pussy” pun here). Instead, I turn up profile after profile of people saying how much they hate/are digusted with cybersex. For example: “DON’T message me if you’re looking for cybersex.” Hot.

2:00. I decide to take the more subtle approach and scope for users who have their in-system IM turned on—Yagan’s recommended OkCupid private room. 7,701 currents are currently online, but only a few hundred with IM. Oops, apparently most users keep their IM turned off, and maybe for this exact reason. I settle for “stalking” (i.e. checking out the profile of) a tattooed poly girl from Queens and sending her an awkward message asking whether she likes dirty chat. I feel creepy.

2:15. Getting antsy, I finally find two cute-ish potential partners with their IM turned on: a thirty-eight year old woman who works in video games and a twenty-five year old “career nerd.” What can I say, I like them dorky. I click their IM bubbles only to discover that before I can even say “hi” I have to: 1) answer 50 personality questions; 2) upload at least two photos of myself; 3) have been on the site at least 72 hours; and 4) match their personality answers at least 50%.

2:30. Okay, info updated. IMing ahoy! Charming remarks sent. Wait for it… And neither of them respond.

2:35. I say, “Ah, screw it!” and head to Gmail to make a new, cybersex-only email account for sending naughty photos to online lovers—partially as a sign of good faith that, at this rate, I’ll ever find some.

2:36. Oh wait, what’s this, an incoming IM from a guy in California? Well that’s something different entirely. Casual banter quickly turns sexy when we discuss the synaesthetic possibility of orgasms.

2:45 to 4:30.Somehow I’ve gone from zero to sixty. Now I’m role-playing as a pirate wench across from this new partner turned sexy lady nurse. I’m on the theoretical examining table while he gives me a thorough check-up, then cures my illness by fingering me. He also shows me how to make the most of a rubber dildo—medically speaking, of course—and how to use it on my wench friends back on the ship. Silliness aside, or maybe because of the silliness, it’s one of the hottest, most well-written encounters I’ve had in weeks. I actually come out daydreaming about sexy nurses

4:30. I reconsider the potential for cybersex on OkCupid. Sex: check. Initial frustration: check. Eventual eye-patch-wearing fun: check. This could be the start of a great porn crossover affair.

Previously in Click Me: Porn and Pong: Videogame Sex Beyond Grand Theft Auto

Click Me runs regularly on villagevoice.com. Look for Bonnie’s cybersex blogging at Naked City, where it may actually take the form of blogging. Got a question about cybersex? Write to your friendly cyberhood sexpert Bonnie Ruberg to ask advice or to share stories about sex and the internet: bonnie [at] heroine-sheik [dot] com.

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