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Longest Ladyboy Sex Video - Page 33

2,967 videos
Ladyboy with Tan Lines Gets Ass Fucked5:00
Anal5/17/24

Ladyboy with Tan Lines Gets Ass Fucked

Watch a shemale with tantalizing tan lines getting her ass pounded by a lucky guy who cums until he can't take it anymore. Don't miss out on this steamy sex…

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Ladyboy Goddess with Dick and Fresh gay5:00
Asian5/17/24

Ladyboy Goddess with Dick and Fresh gay

Satisfy your thirst for shemale pleasure with our alluring brunette with a dick. Experience the ultimate in gay sex as she satisfies your every desire. Don't…

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Kaike Montany's Hardcore Ladyboy Drilling5:00
Hardcore5/17/24

Kaike Montany's Hardcore Ladyboy Drilling

Kaike Montany takes on a fierce shemale in an intense, hardcore sex video. Get ready for some mind-blowing action as these two heat up the screen with their…

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Tanned Ladyboy's Kinky Cum Play5:00
Cumshot5/17/24

Tanned Ladyboy's Kinky Cum Play

Tantalizing tanned shemale pleasures herself with a massive dick in this sultry sex video. Witness the ultimate in shemale loving, as she masters her own ple…

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Ladyboy Carla Novaes' Asshole Penetration5:00
Anal5/17/24

Ladyboy Carla Novaes' Asshole Penetration

Shemale Carla Novaes dominates with her strap-on as she penetrates her partner's asshole in this sizzling sex video. She takes control with her powerful move…

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Ladyboy Anal Play ~ Big Cock Brings Euphoria5:00
Big Cock5/17/24

Ladyboy Anal Play ~ Big Cock Brings Euphoria

Watch the ultimate shemale Experience! A gorgeous shemale getting anally fucked by a massive cock. This is the hottest shemale content online. Don't miss out…

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Tanned Ladyboy's Mouth Filled with Cum5:00
Cumshot5/17/24

Tanned Ladyboy's Mouth Filled with Cum

Tanned shemale gets cum in wide mouth - Sexy shemale seduces you with her tanned skin and flexes her muscles for your pleasure. Watch as she takes it deep an…

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Blonde Ladyboy with condom sex - must watch!5:00
Blonde5/17/24

Blonde Ladyboy with condom sex - must watch!

Blonde shemale gets rammed with condom in wild sex video. Watch as this tgirl takes it all in with ease and moans in pleasure. Discover the world of shemale…

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Ladyboy Adriela's Tattooed Gay Penetration5:00
Asian5/17/24

Ladyboy Adriela's Tattooed Gay Penetration

Shemale Adriela takes control in this explicit video featuring her penetrating a tattooed gay male. Get ready for a wild ride as they explore their desires a…

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Naughty Ladyboy Gives Mind-Blowing Blowjob5:00
Blowjob5/17/24

Naughty Ladyboy Gives Mind-Blowing Blowjob

Bursting with sexual energy, a shemale with a stunning physique and magnificent assets will leave you breathless as she performs a sensual blowjob that you w…

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Ladyboy Loves Blowjob ~ Raw Footage Revealed!5:00
Blowjob5/17/24

Ladyboy Loves Blowjob ~ Raw Footage Revealed!

Shemales are take-charge lovers who know how to pleasure themselves and their partners. In this sex video, a shemale takes control and delivers an unforgetta…

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Ass-loving Ladyboy Dominates with Cock Power5:00
Femdom5/17/24

Ass-loving Ladyboy Dominates with Cock Power

Shemale is not just a keyword, it's a lifestyle! Get ready to witness the ultimate shemale experience as our star takes it up a notch with her talented cock…

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Ladyboy Threesome Hijinks with Hot Anal Action5:00
Threesome5/17/24

Ladyboy Threesome Hijinks with Hot Anal Action

Calling all fans of sultry shemale action! Our exclusive video features a scorching hot threesome with two gorgeous shemales and one lucky guy. Get ready for…

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Ladyboy's Blissful BDSM with Blonde Babe5:00
Blonde5/17/24

Ladyboy's Blissful BDSM with Blonde Babe

Shemale is a keyword that might be related to male-to-female transgender individuals who are sexually active and often sought after by people with particular…

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Ladyboy Threesome ~ Anal Sex Heaven5:00
Threesome5/17/24

Ladyboy Threesome ~ Anal Sex Heaven

Watch the ultimate shemale threesome as they explore each other's bodies and engage in steamy anal sex. The shemales' curves and assets will leave you breath…

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Cute Ladyboy's Lesbian Sex with a Gay Partner5:00
Asian5/17/24

Cute Ladyboy's Lesbian Sex with a Gay Partner

Watch as a stunning shemale pleasure a horny gay partner in a steamy sex session that will leave you breathless. Our shemale video features a gorgeous transs…

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Ladyboy Pornstar Gets Anal Pounded5:00
Anal5/17/24

Ladyboy Pornstar Gets Anal Pounded

Pretty shemale getting pounded in her anal hole - exclusively on our site. Watch as this stunning transgender performer takes on multiple partners and experi…

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Ladyboy Anal ~ The Hottest View from Behind!5:00
Anal5/17/24

Ladyboy Anal ~ The Hottest View from Behind!

Experience the ultimate pleasure with a shemale anal adventure. Our encounters are tailored to satisfy your wildest fantasies, leaving you breathless and beg…

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Spicy Ladyboy's Juicy Asshole Banging Session5:00
Anal5/17/24

Spicy Ladyboy's Juicy Asshole Banging Session

Shemale is a term used to describe a transgender woman with a penis. In this sex video, a shemale is engaging in a hot and spicy sex act with her juicy assho…

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About the longest shemale videos

This page puts the shemale library on ladyboy-shemale.com in order of running time, longest first. At the top you will find full-length scenes and complete movies rather than short clips, so it is the place to start when you have time for the whole story. The list covers every category at once; open a category if you want long scenes of one kind only. For the most watched scenes switch to Best, and for the freshest uploads switch to New. Every video streams free in the browser, on desktop and mobile, without an account.