Melissa Gira Grant gets deep about the San Francisco sex scene every Thursday on SEX SF.
Interesting sex lives are all alike; but every boring San Francisco sex life is boring in its own way.
“Justin” moved to the Bay Area from Modesto – not seeking some sexual refuge, but heeding that other great siren call, a software engineering job in the Valley. He’s still in his early 20s, and cute in that slight and skinny way. You would never know that he’s got a secondary encrypted operating system running inside his computer just for his transwoman-on-man porn.
Hip San Francisco sex has little room for someone like Justin. That has nothing to do with “internalized” anything on his part, some lack of sophistication it’s all too easy to dismiss. “I know about Diva’s,” Justin tells me, referring to the club for transwomen and the genetic males who admire them. The reason he doesn’t go isn’t because he’s ashamed – it’s because he doesn’t want to come off as some chaser creep. “I've spent way too much time objectifying them,” he says. “Which is fake, but at some point, you think that real life might be that way. You know it's not, but it's what you see.”
Instead, Justin relies on Craigslist. He probably spends too much time on Casual Encounters, he says, “which is where most of the t4m [transgender-for-male] ads are.”
That is, there aren’t as many ads from transgender women in the regular dating section of Craigslist, and they don’t have a dedicated “seeking” listing except under “miscellaneous romance” – and he’s not just looking to fool around.
Of one woman he tells me, “We IMed some, but the weird thing was she actually seemed more interested in hooking up.”
He also goes for the women who send fairly tame photos. “You worry about anyone who's that comfortable showing you more,” he explains, “and I liked the idea that there could be something more than just a hookup between us. “
Here’s how he arranged his last date.
One night after trading photos with a girl, she told him that she wanted to meet. “I showered and drove over to her place, probably 10 or 15 minutes away. It was a considerably poorer area, but when I walked in, there was a 50-inch plasma. I think her bed was on the floor. I'm not talking shit, there. Mine is, too.”
It wasn’t until Justin was sitting on my own bed that he ever told me any of this: how they shared oral sex with condoms because he was worried about HIV. “I wasn't sure if she was saying ‘stop’ or ‘don't stop’ when she was coming. I erred on the side of caution and picked wrong.” It was only his second time, he says.
Later I ask him, and tell him there’s no wrong way to answer the question, is he more attracted to transgender women than to non-transgender women? Because the first time he told me any of this, he was about to lose his virginity to me, but by my count, he’s hardly an innocent. “I'm not really sure. If Miss Right came along, I'm not sure it would matter.”
"I'm curious why you wanted to interview me about this," he asks. How do you tell someone, who is actually quite brave and self-aware about his desires, that the reason I wanted to know is because so many other people, even and especially in our sexually accommodating port of call, would think him, if they never thought to ask, boring?
Melissa Gira Grant  writes about sex & the internet at her award-winning blog, Sexerati and at the sex workers' group blog, Bound, not Gagged . Her work has appeared in Best Sex Writing 2008, $pread, Make:, Valleywag, The Frisky, and The Huffington Post. She has been featured in the San Francisco Chronicle, Cosmopolitan (France), Wired News, NPR, SexTV, BBC Radio, and Penthouse Forum, among many others.