Movies Like Bossy MILFS 2

If you liked Bossy MILFS 2 (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
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.
2
Scandalous Sex (2004)
★ 6.9/10
A daughter seeks to restore the reputation of her disgraced father, a wronged college professor. With help of a professional student, she must overcome an ambitious sorority bitch and corrupt college dean.
3
Heartbreakers (2001)
★ 6.2/10
Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then…
4
Bad Sister (2015)
★ 6.6/10
As a top student at St. Adeline's Catholic Boarding School, Zoe senses that something is not quite right about the school's new nun-- a sense proven to be true when it is revealed the "good' nun is an imposter with a…
5
The Four Musketeers (1974)
★ 6.5/10
The Four Musketeers defend the queen and her dressmaker from Cardinal Richelieu and Milady de Winter.
6
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.
7
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
8
Focus (2015)
★ 6.9/10
Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.
9
Adult World (2014)
★ 6/10
Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.
10
Good Luck to You, Leo Grande (2022)
★ 7/10
Nancy Stokes, a retired schoolteacher, is pretty sure she has never had good sex. Now that her husband has died, she is determined to take a tour of sexual vistas that until now she has only imagined. She even has a…
11
Billy Madison (1995)
★ 6.2/10
Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2…
12
Only the Lonely (1991)
★ 6.2/10
Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the…
13
Life of the Party (2018)
★ 6.1/10
When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, who's not entirely sold on the idea…
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
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
16
Hard to Die (1990)
★ 6/10
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
17
WWE WrestleMania XXX (2014)
★ 7.9/10
WrestleMania XXX was the 30th annual WrestleMania professional wrestling PPV event produced by WWE to be held, on April 6, 2014, at the Mercedes-Benz Superdome in New Orleans, Louisiana. The event was the first…
18
Valley Girl (1983)
★ 6/10
Julie, a girl from the valley, meets Randy, a punk from the city. They are from different worlds and find love. Somehow they need to stay together in spite of her trendy, shallow friends.
19
Young People Fucking (2007)
★ 5.9/10
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…
20
Nine to Five (1980)
★ 7/10
Three female employees of a sexist, egotistical, lying, hypocritical bigot find a way to turn the tables on him.