Just doing it

Complicated intimacy with women and men was nothing new to Anna. But when your sex buddy changes gender, the rules change, too.

Helena Echlin

The people with the most baroque sex lives, I've noticed, often are the ones who look the most innocent.

Anna meets me at the House of Shields on New Montgomery Street, a few blocks from the marketing company where she works as a graphic designer. (All names have been changed here.) Still in her office clothes, a convservative blouse and pressed black pants, she has a round, sweet face and brown hair pulled back in a ponytail. To look at her, you'd never think that she has attended workshops on enhancing the female orgasm. Or that she, a lesbian, sleeps with both men and women, sometimes at the same time.

But Anna's sexual adventures aren't enough to give zest to her life. Her work is dull, and she feels frustrated. Like so many confined to offices in the city—where everyone seems to paint, dabble in performance art, or at least blog—Anna views her job as a stopgap until she finds her true calling. That might be easier, she thinks, if she changed her social circle.

"I used to hang out with people who talked about doing something," she says as we begin polishing off hefeweizen. "Now I want to hang out with people who actually are doing something."

Her friend Curits is certainly doing something, although maybe not in the way she means. Curtis is a former woman working hard to become a man. For months he—Curtis already identifies as a man—has been taking testosterone shots. His muscles have gained definition, and his upper lip is dusted with peach fuzz.

Curtis and Anna like to play backgammon and have sex from time to time. Essentially, they are "friends with benefits." That phrase seems inadequate to describe the complicated liaison of a lesbian and a female-to-male transsexual. But whatever you want to call it, the relationship is changing. Anna fears that she is becoming indifferent to Curtis.

"When we get together, it's like, 'What shall we do? Shall we shoot pool or shall we have sex?' And I don't really care which." Anna has the kind of romantic problem you find only in San Francisco. She prefers women, and so the more of a man Curtis becomes, the less she wants to sleep with him. In fact, she is more attracted to Curtis's girlfriend, Wendy.

Things came to a head recently, and as we drain the pint glass, details spill across the table. As Anna and Curtis were fooling around at her place in Oakland, she reached for Curtis's breasts, which he had bound flat to his chest. Curtis pushed her hand away. He went down on Ana, but frustration overwhelmed desire. She craved a female body.

Curtis thoughtfully suggested they call Wendy and invite her over to join in, something they'd done before. She couldn't, it turned out. But on the phone, Wendy invited Anna to think about what she'd like to have happen. After they hung up, Anna decided to write it all down.

"Take off your shirt," she told Curtis. She wrote on his back: Don't let me be in control. Scribbling furiously, she covered all of his skin that wasn't hidden by the binding. Call me little girl. Bite my nipples. Spank me.

Perhaps it's