Movies Like Portland Cum: Kyle's First Time

If you liked Portland Cum: Kyle's First Time (2004), a movie directed by Scott Morris, 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
Eating Out 2: Sloppy Seconds (2006)
★ 6.1/10
How far would you go to get the person of your dreams? With the help of Gwen and Tiffani, Kyle pretends to be heterosexual in order to land Troy, the new guy (and nude model) who's turning the heads of both men and…
2
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…
3
Some Like It Hot (1959)
★ 8.1/10
In Prohibition-era Chicago, musicians Joe and Jerry witness a mob hit, and flee the state in an all-female band disguised as Josephine and Daphne, but further complications set in.
4
A Good Old Fashioned Orgy (2011)
★ 5.8/10
A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.
5
The Ritz (1976)
★ 6/10
To escape from a mobster, businessman Gaetano Proclo orders a cab driver to take him to a place where he can't be found. Unfortunately for Gaetano, the place turns out to be a gay bathhouse.
6
Milk Money (1994)
★ 6.5/10
Three young boys pool their money and pay V, a kindhearted prostitute, to strip for them. Afterward, she drives them home to the suburbs -- but then her car breaks down. It's just as well, though, because a mobster…
7
Tongues Untied (1990)
★ 6.7/10
Marlon Riggs, with assistance from other gay Black men, especially poet Essex Hemphill, celebrates Black men loving Black men as a revolutionary act. The film intercuts footage of Hemphill reciting his poetry, Riggs…
8
Professor Marston and the Wonder Women (2017)
★ 7.1/10
The unconventional life of Dr. William Marston, the Harvard psychologist and inventor who helped invent the modern lie detector test and co-created Wonder Woman in 1941.
9
The Climb (2020)
★ 6.1/10
Kyle and Mike are best friends who share a close bond — until Mike sleeps with Kyle’s fiancée. A stormy but enduring relationship ensues between Kyle, with limitless patience, and Mike, who only lives his life by…
10
Weekend (2011)
★ 7.3/10
After a drunken house party with his straight mates, Russell heads out to a gay club. Just before closing time he picks up Glen but what's expected to be just a one-night stand becomes something else, something special.
11
GirlHouse (2014)
★ 6/10
In an attempt to make some extra cash while away at College, Kylie moves into a house that streams content to an X-rated website. After a deranged fan hacks in to determine the house's location, she finds herself in a…
12
The Knack... and How to Get It (1965)
★ 6/10
A nebbish schoolteacher begs his smooth (and misogynistic) pal to teach him 'the knack' – how to score with women. Serendipitously, the men meet up with a new girl in town, as well as a friendly lunatic who can’t help…
13
Voyeur (2017)
★ 5.9/10
Legendary journalist Gay Talese unmasks a motel owner who spied on his guests for decades. But his bombshell story soon becomes a scandal of its own.
14
Intimacy (2001)
★ 6.2/10
Failed musician Jay abandoned his family and now earns a living as head bartender in a trendy London pub. Every Wednesday afternoon, a woman comes to his house for graphic, almost wordless, sex. One day, Jay follows…
15
The Living End (1992)
★ 6.7/10
Two HIV-positive young men — a semi-employed film critic and a hot hustler — tear off on a cross-country crime spree.
16
Edge of Seventeen (1999)
★ 6.5/10
1984, Sandusky, Ohio. A naive 17-year-old navigates heartbreak and self-expression as he explores his sexuality.
17
Desperate Living (1977)
★ 6.3/10
After killing her husband, Peggy Gravel and her murderous maid Grizelda wind up in the crazy town of Mortville, where Queen Carlotta presides over a sleazy collection of misfits.
18
Saltburn (2023)
★ 6.9/10
Struggling to find his place at Oxford University, student Oliver Quick finds himself drawn into the world of the charming and aristocratic Felix Catton, who invites him to Saltburn, his eccentric family's sprawling…
19
Magic Mike (2012)
★ 6.2/10
Mike, an experienced stripper, takes a younger performer called The Kid under his wing and schools him in the arts of partying, picking up women, and making easy money.
20
Bachelor Party (1984)
★ 6.3/10
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.