The Best and Worst of Cybersex 2007

International threesomes, naked French lessons, and "light and fluffy" breasts

Being a sex writer comes with its perks. While other people are off working nine-to-five jobs and contributing to society, I’m here by my computer, propositioning fellow internet-goers for “research.” Text chat, webcams, virtual worlds, fetishists, first-timers: not only is it fun, it also makes for some seriously colorful stories. That’s why I’ve chosen to look back at the year 2007 the best way I know how: with a list of highlights from my own online sexual encounters. Names have been omitted to protect the innocent, the awkward, and the superlatively bad in cyber bed.

Sexiest encounter with a transgender GI. I admit it: I think writing is hot. Good grammar and vocabulary turn me on. Add some BDSM to a well-crafted sex chat and voilà! Happy New Year to me! Unfortunately, it’s gotten hard to find cybersex partners who compose full sentences—let alone sultry prose. So imagine my delight earlier this year when I found myself on a cyber sofa in the private Second Life home of an eloquent dominatrix. Dressed in a pair of ripped fatigues, she’d brought her submissive along for us to play with—a pretty girl, bound and gagged. My dominatrix spoke enough for two. In between florid descriptions of in-game sex acts, she explained she was a transitioning transgender (male-to-female) in real life, and that she’d recently left the army. I don’t know what impressed me more: her personal story, or her way with words. Who else could have made “cunt” sound elegant while wearing camouflage?

Most discouraging half an hour for the future of cybersex. If you’re looking for a quick online fuck—say to round-out a collection of cybersex transcripts you’re analyzing for linguistics, perhaps—the easiest places to get laid are the AOL chatrooms. Unfortunately, they’re also the most depressing. In a less than 30 minute session I was messaged by more than ten guys; they all used the exact same lines: “Age/sex/location?”; “What do you do for fun?”; “Do you want to suck my cock?” By the end, I had a list of ten stock responses to copy and paste. The most depressing part: no one seemed to notice.

The topless beach where Bonnie got French lessons.
The topless beach where Bonnie got French lessons.

Most educational use of a topless beach. This spring, I was cruising a nude beach in Second Life when I came across a naked avatar standing by himself in the sand. Like many Second Life users, he turned out to speak only French. Lucky for me, our shirt-less flirtations turned into a practice session for my upcoming move to France. Had I been blinded by his well-rendered pecs, or could I really all of a sudden conjugate verbs faster than you could say “animated cyber genitals”?

Most awkward post-coital question about shoes. Just the other day I was instant messaged by a male Click Me fan. While I love hearing from readers, I find that many share the problem of spitting out the question they really want to ask: “Would you like to cyber?” After this reader stepped up to the plate though, I started to wonder if I could possibly be the first woman he’d ever talked to. Thirty seconds after coming, he asked, “Why do women have so many shoes?” Then, “Girls have all these emotions, huh?” Yes, and one of those emotions is “weirded out.”

Hottest in-office story time involving naughty dice. The next best thing to having sex? Hearing about it, in detail. One day this fall I arrived at work to find an email in my inbox from an online partner. With lusty precision, the note recounted the tale of a cyber threesome conducted across the globe. In America, the man in question had rolled a set of naughty dice, while two of his friends in Japan acted out the dice’s instructions (“kiss him,” “lick her,” “fuck him”) in front of their webcam. He watched, masturbated, and documented his orgasm with photos. “Just writing that story got me so hard,” he admitted at the end of his email. Understandably: reading it steamed up the inside of my cubicle for the rest of the week.

Most embarrassing description of a personal body part. Sometimes even the most well-intended compliment can go horribly awry. This summer I bought a Mac, and with it came a built-in camera. For a writer who spends her days getting in people’s virtual pants, such a webcam has only one foreseeable use: nudity. Nervous, I showed my first batch of sexy photos to an online friend. At first he seemed genuinely impressed. But when he started praising my body parts individually, things turned weird. “I really like your breasts,” he said, “they look so light and fluffy.” Light and fluffy? Those are adjectives I use to describe scrambled eggs, not breasts. "Thanks,” I typed back. What else could I say? Ever since, breakfast hasn’t been quite the same.

Most exhibitionistic comment thread on a public blog. A few months back, I blogged about fetishes in cybersex. That got two of my regular commenters talking, and eventually downright near cybering, in the comments of my post. Noticing that they weren’t alone, they finally picked a more private time and place, and they’ve been cyber lovers ever since. On Thanksgiving I got an email from them saying they were “thankful” for “hot and sexy time together, with more to ‘cum’.”

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