Movies Like Her First MILF 27

If you liked Her First MILF 27 (2019), a movie directed by Karl Kinkaid, 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
Below Her Mouth (2017)
★ 6.8/10
An unexpected affair quickly escalates into a heart-stopping reality for two women whose passionate connection changes their lives forever.
3
The Little Death (2014)
★ 6.7/10
A comedy film that looks into the loosely connected lives of people with strange sexual fantasies.
4
Hot Girls Wanted (2015)
★ 6.1/10
A first-ever look at the realities of the professional “amateur” porn world and the steady stream of 18-to-19-year old girls entering into it.
5
The World to Come (2021)
★ 7/10
In 1856, two women forge a close connection despite their isolation on the American frontier.
6
The Mother (2003)
★ 6/10
A grandmother has a passionate affair with a man half her age, who is also sleeping with her daughter.
7
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…
8
Meet Monica Velour (2010)
★ 5.8/10
For Tobe, a nerdy, horny, frizzy-haired cineaste who doesn't quite fit in with the average contemporary teen, the pinnacle of womanhood is Monica Velour, a soft-core actress who reached the zenith of her career in the…
9
Camp Belvidere (2014)
★ 6.5/10
Camp Belvidere is a lesbian romance set in the 1950s about the coming of age of Camp Leader Rose and her forbidden encounter with Nurse Gin. It depicts the journey and evolution of a friendship into a romance between…
10
Elena Undone (2010)
★ 6.9/10
The wife of a pastor who preaches against homosexuality embarks on an affair with a female writer.
11
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.
12
From Straight A's to XXX (2017)
★ 5.9/10
When a change of circumstances leaves Miriam unable to pay her college tuition, she makes a surprising decision: to start performing in adult films, using the pseudonym Belle Knox. Miriam lies to her family and her…
13
The Diary of a Teenage Girl (2015)
★ 6.6/10
Minnie Goetze is a 15-year-old aspiring comic-book artist, coming of age in the haze of the 1970s in San Francisco. Insatiably curious about the world around her, Minnie is a pretty typical teenage girl. Oh, except…
14
Class (1983)
★ 6/10
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the…
15
sex, lies, and videotape (1989)
★ 7/10
Ann, a frustrated wife, enters into counseling due to a troubled marriage. Unbeknownst to her, her husband John has begun an affair with her sister. When John’s best friend Graham arrives, his penchant for interviewing…
16
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…
17
If These Walls Could Talk 2 (2000)
★ 6.5/10
The stories of three lesbian couples -- who live in the same house at different periods of time -- who are at a crossroads in their lives. In 1961, Edith loses her lover, Abby, to a stroke. Linda and Amy struggle with…
18
Am I OK? (2024)
★ 6.3/10
Lucy and Jane have been best friends for most of their lives and think they know everything there is to know about each other. But when Jane announces she's moving to London, Lucy reveals a long-held secret. As Jane…
19
Vampyres (1974)
★ 6/10
A duo of bisexual female vampires prey on passing motorists, whom they seduce and murder in the English countryside.
20
Michael Jackson: Dangerous - The Short Films (1993)
★ 8.2/10
Michael Jackson's Dangerous album once again rocketed the global superstar to mega-platinum success! "Dangerous - The Short Films" captures the visual and musical highlights of his most recent string of hit singles. As…