Movies Like My Secretary Is A Secret Transsexual

If you liked My Secretary Is A Secret Transsexual (2009), a movie, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Different for Girls (1997)
★ 7.1/10
Paul and Kim meet when their vehicles collide. Paul is fascinated with the attractive Kim. It turns out that the two were childhood friends in Catholic boys' school, but back then, before the operation, Kim was named…
2
Set It Up (2018)
★ 6.9/10
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
3
Zerophilia (2005)
★ 5.9/10
Luke, a young man insecure about his masculinity, discovers he's a Zerophiliac, with the ability to change sex at will. Join Luke as he journeys into the extraordinary world of Zerophilia where so many crazy questions…
4
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
5
Secretary (2002)
★ 6.8/10
A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.
6
Players (2024)
★ 6.1/10
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
7
Everything You Always Wanted to Know About Sex *But Were Afraid to Ask (1972)
★ 6.5/10
A collection of seven vignettes, which each address a question concerning human sexuality. From aphrodisiacs to sexual perversion to the mystery of the male orgasm, characters like a court jester, a doctor, a queen and…
8
Nine 1/2 Weeks (1986)
★ 6.1/10
An erotic story about a woman, the assistant of an art gallery, who gets involved in an impersonal affair with a man. She barely knows about his life, only about the sex games they play, so the relationship begins to…
9
My Awkward Sexual Adventure (2012)
★ 6.7/10
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
10
I Am Divine (2014)
★ 7.3/10
Harris Glenn Milstead, aka Divine (1945-1988) was the ultimate outsider turned underground hero. Spitting in the face of the status quos of body image, gender identity, sexuality, and preconceived notions of beauty…
11
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
12
Barbarella (1968)
★ 6/10
In the far future, a highly sexual woman is tasked with finding and stopping the evil Durand-Durand. Along the way she encounters various unusual people.
13
Trafficked (2017)
★ 6.6/10
In this story inspired by real characters, three girls from America, Nigeria and India are trafficked through an elaborate global network and enslaved in a Texas brothel, and must together attempt a daring escape to…
14
Sex and Death 101 (2007)
★ 6.2/10
A guy's life is turned around by an email, which includes the names of everyone he's had sex with and ever will have sex with. His situation gets worse when he encounters a femme fatale who targets men guilty of sex…
15
Splendor (1999)
★ 6.2/10
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
16
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
17
Shortbus (2006)
★ 6.2/10
In post-9/11 New York City, an eclectic group of citizens find their lives entangled, personally, romantically, and sexually, at Shortbus, an underground Brooklyn salon infamous for its blend of art, music, politics…
18
A Night at the Roxbury (1998)
★ 6.6/10
Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful…
19
Preaching to the Perverted (1997)
★ 6.1/10
A computer wizard infiltrates a London sex club to get evidence for a shutdown, but falls for the proprietress.
20
Ladies First (2026)
★ 6/10
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.