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Longest Ladyboy Sex Video - Page 34

2,967 videos
Tall Ladyboy Astrid Blowing You Away for Cash5:00
Asian5/17/24

Tall Ladyboy Astrid Blowing You Away for Cash

Controversial, yet seductive, busty shemale Astrid is ready to fulfill your wildest fantasies. Offering the ultimate sensual experience, she takes your breat…

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Ladyboy's Succulent Sucking Session5:00
Blowjob5/17/24

Ladyboy's Succulent Sucking Session

Spicy shemale gets her dick sucked – watch her even more impressive performance in this exclusive sex video. Experience the ultimate pleasure of a shemale' a…

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Dinise, the Slender Ladyboy's Anal Sex5:00
Anal5/17/24

Dinise, the Slender Ladyboy's Anal Sex

Anal sex with slender shemale Dinise - Explore the world of shemale erotica and enjoy the stunning beauty of Dinise as she takes on her partner in a sensual…

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Ladyboy's Hardcore Fuck with Tanned Gay Bae5:00
Hardcore5/17/24

Ladyboy's Hardcore Fuck with Tanned Gay Bae

Watch the newest shemale porn video where a hardcore tanned gay is being fucked by a beautiful shemale. This steamy sex scene is not to be missed!

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Ladyboy Tranny Gets Paid for Cock Worship5:00
Asian5/17/24

Ladyboy Tranny Gets Paid for Cock Worship

Watch our hot Shemale Tranny whore gets paid to take cock. She is eager to please and ready to take your load. Make sure not to miss the hot action and exclu…

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Ladyboy Goddess Adriela's Anal Pleasure5:00
Anal5/17/24

Ladyboy Goddess Adriela's Anal Pleasure

Pretty shemale Adriela getting fucked in her anal by a hung stud. Watch as she moans in pleasure and takes it all in. Shemale ass worship at its finest, don'…

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Latina Ladyboy Gangbang with Explosive Facials5:00
Gangbang5/17/24

Latina Ladyboy Gangbang with Explosive Facials

Venture into the world of shemale pleasure with our Latina shemale gangbang video. Watch as these beautiful, curvesome shemale performers take on multiple pa…

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She-Male Takes Control in Steamy Threesome5:00
Threesome5/17/24

She-Male Takes Control in Steamy Threesome

Watch as a sexy shemale leads a couple into a steamy threesome sex session. Experience the passion and heat as they explore each other's bodies in new and ex…

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Ladyboy Gangbang ~ Black Cock Worship5:00
Gangbang5/17/24

Ladyboy Gangbang ~ Black Cock Worship

Discover the intense pleasure of shemales as they perform unforgettable sex acts with their partners. Watch as these stunning individuals take control and sh…

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Ladyboy Goddess Reigns with Big Ass Lay5:00
Anal5/17/24

Ladyboy Goddess Reigns with Big Ass Lay

Shemale is a term used for a transgender woman with male genitalia who often exhibits feminine characteristics. In this explicit sex video, we see a shemale…

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Black Ladyboy's Anal Pleasure with Hard Dick5:00
Anal5/17/24

Black Ladyboy's Anal Pleasure with Hard Dick

Outrageous XXX video featuring a stunning black shemale taking it deep from a hard dick. Watch her moan with pleasure as she gets anally fucked, leaving you…

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Slutty Ladyboy Fuck ~ Tight Asshole Action5:00
Anal5/17/24

Slutty Ladyboy Fuck ~ Tight Asshole Action

Experience the ultimate pleasure with a gorgeous shemale as she invites you to explore her tight asshole. Get lost in the wild delight of this slutty shemale…

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Ladyboy anal whore enjoys cute tranny teen5:00
Anal5/17/24

Ladyboy anal whore enjoys cute tranny teen

Shemale is a term for an individual who was assigned male at birth but identifies as female. In this video, we have a super cute shemale teen who loves to ge…

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Ladyboy pays it forward with gorgeous manhood5:00
Asian5/17/24

Ladyboy pays it forward with gorgeous manhood

Watch the amazing shemale, Tranny, as she takes control and dominates her man in a wild sex session. With her incredible curves and hard assets, Tranny will…

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Ladyboy with Huge Dick Takes on Anally5:00
Anal5/17/24

Ladyboy with Huge Dick Takes on Anally

Watch now as a stunning shemale with a massive cock takes it deep inside her tight asshole. Let yourself be mesmerized by the sight of this incredible she-ma…

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Ladyboy Dominates White Ass with Massive Cock5:00
Femdom5/17/24

Ladyboy Dominates White Ass with Massive Cock

Welcome to the ultimate shemale experience! This video features a gorgeous black transexual with a massive cock penetrating a willing white male's tight ass…

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Ladyboys get him off in steamy threesome fun5:00
Threesome5/17/24

Ladyboys get him off in steamy threesome fun

Shemale is a term commonly used to describe a transgender individual who was assigned male at birth but identifies as female. In this sex video, you will dis…

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Ladyboy Daniela Marks Brings Double Pleasure5:00
Asian5/17/24

Ladyboy Daniela Marks Brings Double Pleasure

Shemale Daniela Marks takes on two guys in this steamy sex video. Watch as she dominates both men with her impressive curves and impressive skills. Don't mis…

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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.