“I always thought of myself as a transgendered person,” said Bond, who is 49, lounging on a sofa in black capri pants and silver sandals. “I just lived my life and I didn’t really have the exact language for what I was.”

That act of semantic self-determination seems to have increased Bond’s creative output, too. The last year has seen a flurry of original recordings, lounge acts, exhibitions, music tours and a short memoir, “Tango,” about growing up in Maryland as a proto-glam “trans child” obsessed with Greta Garbo. Like Bond, the memoir is droll, pensive and filled with zingers teetering between funny and ferocious.

This spring, Bond starred in “Jukebox Jackie,” a play at La MaMa that paid tribute to the Warhol “superstar” Jackie Curtis; traveled to Vienna to sing at an AIDS charity ball; and is performing near Times Square to promote “Silver Wells,” the singer’s second album in two years.

While there are certainly other performers known for turning androgyny into high art, Bond has emerged as a kind of mother hen (make that gender-neutral parent fowl) to the city’s trans community, albeit with some reluctance.

“I find it frightening to think that other people are looking to me to speak for them,” Bond said. “What’s uniquely interesting about people who are transgender is this exploration of a truth that is not evident within the lexicon of society at large.”

That sense of searching wisdom underlies “Silver Wells,” a collection of melancholy covers. The title is a nod to the Joan Didion novel “Play It as It Lays.” Her image, along with Jean Genet’s, appears in shimmering dream-catchers in Bond’s living room, opposite a cartoonishly baroque vanity table, a gift from the children’s book author Ian Falconer.

Bond first read the novel at 15. “It was so stark and, in a way, depressing, but at the end she decides that nothing matters,” Bond said, referring to the book’s protagonist. “And there was something about living as this sort of undercover trans youth and reading that nothing mattered that I found to be very liberating.”

A similar winking nihilism was on display this month at 54 Below, a new cabaret space below the original Studio 54, where Bond is performing on Mondays through July 9. At the kickoff show, the performer, looking vampy in a borrowed Lanvin dress and blown-out strawberry-blond hair, paused between torch songs to reflect on growing older.

“I can’t believe Whitney Houston and I are the same age,” Bond purred. “Well, now I’m my age. She’s dead.”

The punky crowd laughed, and Bond, sensing a rambunctious mood, directed the accompanist to skip the next two ballads, both AIDS tributes. “Let’s just say we’re at Studio 54,” Bond said. “If you want an AIDS memory, take a deep breath.”

The joke was, in some sense, a callback to Kiki DuRane, Bond’s half of the twisted cabaret duo Kiki and Herb. Bond and the musician Kenny Mellman created the act in San Francisco in 1993, as a steely rejoinder to the plague that was decimating the city. They became an underground (and then above ground) sensation in New York, where they headlined Carnegie Hall and performed a Tony-nominated Broadway show.

But Bond grew tired of Kiki, a boozy millennia-old lounge singer, and shed the character in 2008, parting ways with Mr. Mellman. In an interview with New York magazine last year, Mr. Mellman said the two no longer speak. “When I was portraying Kiki, I had this character to hide behind,” Bond said, back at the apartment, a small East Village walk-up decorated like a fading Hollywood star’s boudoir. “Now I’m doing my own things, and it’s a little bit scarier.”

Bond’s living arrangement dictated the new album’s mise-en-scène. The performer’s old loft, above the grungy Mars Bar on Avenue A, was being demolished, sending Bond into temporary exile, not to mention the disorienting effect that came with beginning estrogen treatment.

“I started to really feel it around the same time that I was out of my house and on the road,” Bond said, ashing a cigarette into a garlic jar. “So my body was very adolescent, in a way, and I was living out of two suitcases.”

The songs (by the likes of Leonard Cohen, Ronee Blakley and Kurt Weill) have a theme of dislocation, and they acted as comfort food for Bond, who had also ended a five-year relationship with the singer Nathan (a k a Nath Ann) Carrera.

“I broke up with him on a Thursday and went into the studio to record this record on a Tuesday, so it had some bearing on it,” Bond said with a rueful laugh.

For now, the transitions (at least the obvious ones) are over. But at 54 Below, Bond was still navigating the uncharted. Introducing a doleful Kate Bush song, Bond said: “I don’t know what this song’s about, ladies and gentlemen. But I’ve attached my own meaning to it.”

[BTW, read my (and Annika’s) review of Tango at Autostraddle]