Harvey Fierstein certainly knows his way around men in frocks. The writer and actor began his performing career as a drag queen, and drag performance has been the fodder for many of his own plays and musicals, including “Torch Song Trilogy,” “La Cage Aux Folles” and “Kinky Boots.”

As in “Kinky Boots,” the men in Fierstein’s 2014 play “Casa Valentina” appreciate the value of sturdy heels that come in wide-width sizes. But the characters here aren’t drag performers. They’re the patrons of a small Catskills resort in the early 1960s — a place where ostensibly straight men, many with wives and children, can shed their gray flannel suits for the weekend in favor of party dresses and pearls, safe in the company of their fellow cross-dressers.

‘Casa Valentina’ : 2.5 out of 4 CST_ CST_ CST_ CST_ CST_ CST_ CST_ CST_ When: Through Sept.29 Where: Pride Arts Center — The Broadway, 4139 N. Broadway Tickets: $30–$40 Info: pridefilmsandplays.com Run time: 2 hours 10 minutes, with one intermission

But while “Casa Valentina” — now receiving its Chicago premiere in a Pride Films & Plays production — offers an intriguing portrait of gender transgressors in an era of rigid social boundaries, it shies away from really delving into the motivations behind their explorations.

Fierstein was inspired by a real Catskills resort where such gatherings took place, about which details emerged after a furniture dealer discovered a trove of photographs at a flea market in the mid-aughts. Known as Casa Susanna, it was owned by Tito and Marie Valenti. Susanna was the name of Tito’s femme persona; Marie, conveniently for their clientele, ran a wig shop in Manhattan, and could provide feminine beauty lessons along with cooking for her guests.

Fierstein transfers some of these personal details onto his innkeepers. The Chevalier D’Eon is owned by George (Patrick Byrnes) and Rita (Nicholia Q. Aguirre), who met when he walked into her wig shop in search of an upgrade. Valentina is George’s vivacious alter ego, who plays social director at the resort while the warm, practical Rita oversees domestic operations.

On the weekend of the play’s setting, the pair are expecting a small crowd of mostly regular guests: There’s Bessie (Michael Hagedorn), the self-described class clown; Terry (Kingsley Day), the prim and proper elder in a sensible schoolmarm’s bob; Gloria (Josh Marshall), a stylish younger patron; and Amy (Robert Koon), a no-nonsense matron who in her civilian life is a powerful federal judge.

Two characters are new visitors to Chevalier D’Eon. A young man named Jonathan (Micah Kronlokken), who made acquaintance with Gloria’s male counterpart Michael in the ladies’ shoe aisles, is nervously making his public debut as Miranda while his wife is visiting her mother.

And then there’s Charlotte (Danne W. Taylor), a well-known figure within this underground subculture as the publisher of a magazine for men with this particular interest. Charlotte has a vision to expand her magazine into a movement, which she calls “the sorority,” with non-profit status and a mission to normalize transvestism. But her mission this weekend is to persuade the girls of the Chevalier D’Eon to abandon their anonymity and come out publicly as cross-dressers — and to sign affidavits swearing that they are not now, nor have they ever been, homosexuals.

Charlotte’s overt disgust at homosexuality allows Fierstein a bit of time-tempered authorial commentary. Charlotte asserts that 50 years in the future, gay people will still be scuttling through dark alleys, while heterosexual transvestites like herself will be as socially acceptable as smoking cigarettes. We see what you did there, Harvey.

Here, near the end of the first act, is where Fierstein’s script first threatens to become really interesting after an hour of pleasant but epigrammatic exposition. How do these men view their proclivity for feminine clothing? It’s never presented as a fetish, though there are mild allusions to sexual arousal. Bessie is a devotee of Oscar Wilde and jokes about her miserable marriage. Many of the guests, when presenting as their feminine selves, talk about their male identities in the third person, as if they were a separate entity. Might some of these characters identify as gay or bisexual or transgender, if they’d had the framework and vocabulary in 1962 to do so?

Though Fierstein sets up these questions in our minds, he can’t truly answer them, instead pivoting toward soap-opera melodramatics that lead to a deflating-balloon anticlimax. Still, we can enjoy our time with these characters, which are for the most part richly drawn in director Michael D. Graham’s production.

Byrnes is particularly winning in his sort-of-dual role; his businessman George bounds onstage with big Fred MacMurray energy, only to soften before our eyes as he sits down at his makeup table to become Valentina. Aguirre is an anchoring presence as Rita, whose facade of comfort slowly cracks.

Graham’s physical staging isn’t quite as steady as his cast, though; Evan Frank’s crowded, multilevel set design unnecessarily concentrates most of the action in a cramped and ill-defined space. Like Fierstein’s characters, it knocks down fences but keeps hemming itself in anyway.

Kris Vire is a local freelance writer.