Netiquette 101: How to Have Cybersex That Isn't Completely Regrettable

Guidelines for how to safely bang your friends online.

by Drew Millard
Sep 28 2015, 11:10pm

"All Is Full of Love" robots at the Museum of Modern Art's Bjork retrospective.

Welcome to Netiquette 101, in which we'll be using cyber-case studies to teach you basic but valuable cyber-lessons in how to be a better cyber-citizen. Last week, we discussed how to find out if your online friends want to bang. This week, we'll be talking about how to bang your friends, online.

Case Study: Ah, the timeless art of cybersex. What began as two people instant messaging about banging has turned into a hairy-palmed cornucopia of sexting, nude-swapping, video-chatting, and mixed-media sexytime. Much like a Fleshlight full of flesh-eating bacteria, or listening to the Van Halen discography on shuffle, if you're not careful, cybersex can bring you great pleasure and then great pain.

Last December, the Saudi Gazette reported on the systematic cyber-seduction and subsequent blackmail of Saudi men by con artists in Morocco and Algeria. Posing as buxom young women, scammers would contact young Saudis on Facebook, eventually developing online relationships with them and then convincing them to have cybersex (and masturbate for them over Skype). The scammers would then threaten to post the cybersex logs, as well as the videos of them masturbating if they weren't paid off. Around that same time, a member of the Moroccan parliament, Adil Tchikitou, claimed that a cyber-gang led by a 17-year-old boy had tried to blackmail him, claiming that they had footage of the lawmaker masturbating during a cybersex session.

What We Can Learn: Before you fully commit to cybersexual activity with someone you've never met, you should probably confirm that the person is actually who they claim to be. Otherwise, you could be in for a terrible, no-good surprise, like blackmail, or more likely, the uncomfortable realization that you've been duped by someone you're not actually attracted to.

Assuming your cybersex partner is who they say they are, it's important to not jump into anything too quickly, or else you're going to look like a weirdo. Pick up the cues your internet friend (with internet benefits) is laying down. If they chat, "I've been thinking about you a lot lately," maybe respond with, ";)". If they're all, "Ew, not like that!" then let it die. But if they're like, "Yeah, I'm definitely attracted to you," then maybe it's time to ask if they want to take it to video.

Case Study: In 2010, the world was shocked when Deadspin published photos of a semi-flaccid penis that was allegedly attached to the legendary quarterback Brett Favre. According to Deadspin, Favre, who was playing for the New York Jets at the time the photos were allegedly taken, had sent the cock shots to Jets sideline reporter Jenn Sterger as part of an extended—and repeatedly rebuffed—attempt to seduce her. The most embarrassing part of the story? One of the pictures showed Favre wearing what appeared to be Crocs. Ultimately, the NFL's "forensic analysis" (whatever that means) failed to establish a connection between Favre and the photos (or presumably, the Crocs).

What We Can Learn: Sending someone a picture of your bare flesh is a risky proposition. Even if you're sending it to someone you trust who genuinely loves you, that love can turn cold, and that someone can take the nudes you once sent out of love and show them to the world out of hate. Now, I'm an advice columnist and not your mom, so I would never tell you not to send someone a (consensual) nude. Sexting, exchanging nudes, and the like are intimate acts that can strengthen a relationship between two people, and make it an even closer relationship. But just as an insurance policy, you should make identifying your nudes as hard as successfully filing a FOIA request. That means not letting your nudes contain any identifying scars, birth marks, or tattoos. Take the photo against a generic, nondescript background, and if your Crocs somehow make it into the picture, throw them out. And no matter what, don't take a nude featuring your face.

Case Study: The following story comes from a Netiquette 101 reader who wishes to remain anonymous. He met a woman in his area on OKCupid and struck up a correspondence with her. Eventually, our anonymous friend came home drunk one night and hopped on OKCupid, only to find that his new internet penpal was also online. As for what happened after that... I'll let him take it from here:

She messaged me something about how she was horny and wanted to have sex. I assumed she meant she wanted me to come over, so I typed something about calling a cab. But she said she wanted to have sex over the chat on OKCupid. I went with it.

She suggested I send her a pic, but I explained that I had a Razr at the time with a broken camera, so that was out of the question. She said she didn't have a cameraphone either, so she started sending basically everything else sexual you could possibly write and get semi-aroused at via words. I tried to do the same, but it felt overly clinical; how many different ways can you write that you'd like to put your penis into someone?

This went on for like 15 minutes, and then she said she came. I lied and said I did, too.

The next night, I looked for her profile, and found out she completely deactivated it.

What We Can Learn: Having legit, typing-to-another-person-about-fucking-them cybersex is hard, in part because to have cybersex is to more or less extemporaneously collaborate on writing a sex scene with another person. It is exceedingly difficult to pull off without feeling self-conscious, or like a fool. Even great literature contains some absolutely shit-poor sex scenes.

Instead of being all "durr, let's fuck, but online" to your partner, it's way easier to tell them exactly what you want to do to them and have done to you the next time the two of you see each other, in the most specific way possible. This allows you to think about an imagined future in which you'll actually have sex, rather than a real present in which you are simply typing about having sex. And you get bonus points if you actually do the stuff you tell each other about later. Talking to your partner about how the two of you are going to fuck each other and then actually fucking each other like that is a time-honored way to keep your relationship hot and heavy in cyberspace so fractured that neither hotness nor heaviness is often achieved.

If you have any burning netiquette questions you'd like answered, send them to Drew via email ( or on Twitter.

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