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Found 34 movies
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Amator (9) Lakeview Entertainment (7) Lbo Entertainment (7) Severe Society Films (3) Legend (2) Kick Ass Pictures (1) Brat Perversions Films (1) Fun Movies (1) Cx Wow (1) California Star Productions (1) Minx Productions (1) Show moreActors
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Fetish (34) Sissification / Feminization (34) Crossdressing (34) Bdsm (31) Female Domination (31) F On M (23) Bondage (22) Humiliation (21) Pegging (19) Femdom - F On M (19) Submissive Male (18) Feminization / Sissification (18) Strap-On (16) Transsexual (13) Spanking (12) Femdom (11) Domination (11) Pantyhose & Stockings (11) European (10) Anal (10) Show more![Dude Looks Like A Lady Dude Looks Like A Lady](https://cdn.adultfilmindex.com/storage/movies/485/17485_front.jpg)
![Sissy Circus Sissy Circus](https://cdn.adultfilmindex.com/storage/movies/365/89365_front.jpg)
Sissy Circus
2014 | Lakeview Entertainment | Runtime: 1h 6min
![Dude Looks Like A Lady 2 Dude Looks Like A Lady 2](https://cdn.adultfilmindex.com/storage/movies/332/236332_front.jpg)
Dude Looks Like A Lady 2
2001 | Legend | Runtime: 1h 56min | Series: Dude Looks Like A Lady
![Sissy: A Slut Documentary Sissy: A Slut Documentary](https://cdn.adultfilmindex.com/storage/movies/977/300977_front.jpg)
Sissy: A Slut Documentary
2020 | Brat Perversions Films | Runtime: 20min
![Popo-Fotzchen Popo-Fotzchen](https://cdn.adultfilmindex.com/storage/movies/903/305903_front.jpg)
Popo-Fotzchen
2021 | Fun Movies | Runtime: 1h 29min
![Kink School: A Guide To Sissy Slut Play Kink School: A Guide To Sissy Slut Play](https://cdn.adultfilmindex.com/storage/movies/264/292264_front.jpg)
Kink School: A Guide To Sissy Slut Play
2017 | Severe Society Films | Runtime: 3h 22min | Series: Kink School
![Sissy Education 4: Gangbang Slut Sissy Education 4: Gangbang Slut](https://cdn.adultfilmindex.com/storage/movies/533/293533_front.jpg)
Sissy Education 4: Gangbang Slut
2017 | Amator | Runtime: 60min | Series: Sissy Education
![Sissy Education 5: Fickmaschinen Und Andere Nette Gemeinheiten Sissy Education 5: Fickmaschinen Und Andere Nette Gemeinheiten](https://cdn.adultfilmindex.com/storage/movies/534/293534_front.jpg)
Sissy Education 5: Fickmaschinen Und Andere Nette Gemeinheiten
2017 | Amator | Runtime: 59min | Series: Sissy Education
![Sissy Education 6: Eingeritten Sissy Education 6: Eingeritten](https://cdn.adultfilmindex.com/storage/movies/330/294330_front.jpg)
Sissy Education 6: Eingeritten
2018 | Amator | Runtime: 55min | Series: Sissy Education
![Slut Training Slut Training](https://cdn.adultfilmindex.com/storage/movies/071/297071_front.jpg)
Slut Training
2018 | Amator | Runtime: 56min
![Sissy Education 7: Extremely Used Sissy Education 7: Extremely Used](https://cdn.adultfilmindex.com/storage/movies/876/297876_front.jpg)
Sissy Education 7: Extremely Used
2018 | Amator | Runtime: 1h 2min | Series: Sissy Education
![A Model Sissy A Model Sissy](https://cdn.adultfilmindex.com/storage/movies/627/275627_front.jpg)
A Model Sissy
2012 | Lakeview Entertainment | Runtime: 37min
![Owned And Opened Owned And Opened](https://cdn.adultfilmindex.com/storage/movies/910/253910_front.jpg)
Owned And Opened
2008 | Lakeview Entertainment | Runtime: 49min
![Stairway Slut Stairway Slut](https://cdn.adultfilmindex.com/storage/movies/409/265409_front.jpg)
Stairway Slut
2008 | Lakeview Entertainment | Runtime: 27min
![Jade Indica Is A Dominatrix 3 Jade Indica Is A Dominatrix 3](https://cdn.adultfilmindex.com/storage/movies/348/267348_front.jpg)
Jade Indica Is A Dominatrix 3
2010 | Lakeview Entertainment | Runtime: 1h 15min | Series: ... Is A Dominatrix - Lakeview
Corporate Make Over
2006 | Lbo Entertainment | Runtime: Unknown
![Men Into Women Men Into Women](https://cdn.adultfilmindex.com/storage/movies/045/379045_front.jpg)
Men Into Women
2020 | Lbo Entertainment | Runtime: 1h 25min
![Viper 5: Gender Fusion Viper 5: Gender Fusion](https://cdn.adultfilmindex.com/storage/movies/350/385350_front.jpg)
Viper 5: Gender Fusion
1997 | Lbo Entertainment | Runtime: 54min | Series: Viper
Sissy Abduction
2017 | Minx Productions | Runtime: 55min
Pain Dance
2018 | California Star Productions | Runtime: 60min
Sissy Und Cuckold And Loser Training
2018 | Amator | Runtime: 1h 4min
Sissy University
2019 | Cx Wow | Runtime: 2h 0min
![Sissy Training Sissy Training](https://cdn.adultfilmindex.com/storage/movies/706/444706_front.jpg)
Sissy Training
2013 | Amator | Runtime: 1h 5min
Sissy Slut Training
2015 | Amator | Runtime: 1h 10min
![Academy For Sissies: Lesson Make-Up And Wigs Academy For Sissies: Lesson Make-Up And Wigs](https://cdn.adultfilmindex.com/storage/movies/480/410480_front.jpg)
Academy For Sissies: Lesson Make-Up And Wigs
2009 | Severe Society Films | Runtime: 1h 24min | Series: Academy For Sissies
![Academy For Sissies 3: Shaving And Stripping, Being A Well-Groomed Sexy Sissy Slut Academy For Sissies 3: Shaving And Stripping, Being A Well-Groomed Sexy Sissy Slut](https://cdn.adultfilmindex.com/storage/movies/579/428579_front.jpg)
Academy For Sissies 3: Shaving And Stripping, Being A Well-Groomed Sexy Sissy Slut
2010 | Severe Society Films | Runtime: 1h 10min | Series: Academy For Sissies
Valentine Vixens
2020 | Lakeview Entertainment | Runtime: 48min
![Kick Ass Chicks 78: Feminized Kick Ass Chicks 78: Feminized](https://cdn.adultfilmindex.com/storage/movies/499/814499_front.jpg)