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Longest Ladyboy Sex Video - Page 39

2,597 videos
Ladyboy Sluts Debut Anal Duo with Loud Kinks4:56
Anal5/17/24

Ladyboy Sluts Debut Anal Duo with Loud Kinks

Shemale sluts dominate the scene in this extreme anal duo, where kinks are taken to the next level. Get ready for loud moans and pure pleasure as these shema…

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Ladyboy Domination ~ Your Dick is Not Enough4:56
Femdom5/17/24

Ladyboy Domination ~ Your Dick is Not Enough

Unleash your desires with a shemale and feel the thrill of exploring new horizons. Our sizzling hot shemale will tantalize your senses and leave you breathle…

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Interracial couple having sex on a couch4:56
Couple5/17/24

Interracial couple having sex on a couch

A man and a woman are in a room together. He leans over her while she sits on a couch. They engage in sexual activity. The man is naked and the woman wears a…

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Tattooed woman and man have sex on a white bed4:56
Asian5/17/24

Tattooed woman and man have sex on a white bed

A tattooed brunette woman sits on a white bed. A man with many tattoos leans over her body. They engage in sex together in the bright room. The scene shows t…

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Anal Masturbation with Ladyboy in Her Prime4:56
Masturbation5/17/24

Anal Masturbation with Ladyboy in Her Prime

Welcome to a steamy masturbation session with a gorgeous shemale in her late 20s. Sit back and watch as she teases her anal with a toy, squeezing her curves…

WatchedAnal
Trans woman with big tits rides a man on a bed4:56
Busty5/17/24

Trans woman with big tits rides a man on a bed

A naked woman and a man are in a bedroom. She sits on top of him while he lies on the bed. They move together on the white sheets. The scene ends with them c…

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Two women in stockings pose on a bed4:56
Stockings5/17/24

Two women in stockings pose on a bed

Two women wearing lingerie are in a bedroom. One woman lies on her stomach on the white bed. The other woman kneels behind her and looks at the camera. They…

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Two tattooed women have sex on a bed4:56
Asian5/17/24

Two tattooed women have sex on a bed

Two tattooed women are on a white bed in a bedroom. One woman wears white stockings and white heels while lying on her stomach. The other woman wears black l…

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Two men touch a naked woman from behind4:56
Asian5/17/24

Two men touch a naked woman from behind

A naked woman stands between two men in a room. The men reach out to touch her bare skin. They look at her body while holding her hips. The scene shows them…

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Blonde Ladyboy's Hot Hotel Room Hardcore Kinks4:55
Blonde5/17/24

Blonde Ladyboy's Hot Hotel Room Hardcore Kinks

Watch as a stunning blonde shemale takes control in a hot hotel room, engaging in hardcore kinks that will leave you breathless. Experience the ultimate plea…

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Interracial amateur anal sex on a sofa4:55
Amateur5/17/24

Interracial amateur anal sex on a sofa

An interracial couple is in a living room. The woman is on a sofa in doggy style. The man performs anal sex on her. He finishes with a facial cumshot.

WatchedAnal
Ladyboy Jackeline Sobral's Steamy Solo Session4:55
Solo5/17/24

Ladyboy Jackeline Sobral's Steamy Solo Session

Stunning shemale Jackeline Sobral takes us on a sensual solo journey in this must-watch video. Watch her delicate touch lead to passionate pleasures, leaving…

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Sabrina gets a blowjob from a man4:55
Blowjob5/17/24

Sabrina gets a blowjob from a man

Sabrina lies on a bed in a bedroom. A man approaches her and starts a blowjob. She holds onto his body while he works. The scene ends with them continuing th…

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Shemale and man have sex on a couch4:55
Asian5/17/24

Shemale and man have sex on a couch

A naked woman and a man are on a couch in a room. The man moves over her while she lies on her back. They engage in hardcore sex together. The scene shows th…

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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.