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Longest Ladyboy Sex Video - Page 41

2,597 videos
Ladyboy's Ass Desires Black Dildo Mauling4:00
Toys5/17/24

Ladyboy's Ass Desires Black Dildo Mauling

Watch the shemale sensation as she invites a black stud to penetrate her tight ass. Experience the ultimate pleasure as she moans and groans with each thrust…

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Anal Slammed by Blonde Ladyboy Bottoms4:00
Blonde5/17/24

Anal Slammed by Blonde Ladyboy Bottoms

Experience the ultimate pleasure with our blonde shemale bottoms as they take charge in anal sex. Our shemale escorts are ready to please with their perfect…

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Ladyboy in Leather Dominates with Anal Fucking4:00
Femdom5/17/24

Ladyboy in Leather Dominates with Anal Fucking

Experience the ultimate pleasure with our shemale in leather fucking her partner's asshole. Our shemale's incredible skills will leave you breathless and beg…

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Latina shemale with big tits on a bed4:00
Latina5/17/24

Latina shemale with big tits on a bed

A blonde latina shemale lies on a bed. She has big tits and is completely naked. She looks at the camera with her mouth open. The scene takes place in a bedr…

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Ladyboy Strip Tease ~ Ripe for the Picking4:00
Asian5/17/24

Ladyboy Strip Tease ~ Ripe for the Picking

This video is a must-watch for all lovers of shemales. Watch as this cute shemale takes off her slutty dress and teases you with her sexy body. You won't be…

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Ladyboy with a Huge Cock Teases and Pleasures4:00
Asian5/17/24

Ladyboy with a Huge Cock Teases and Pleasures

Shemale is a term used to describe a transgender person with a male biological sex who identifies as female. In this video, we see a hot shemale with a nice…

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Paloma touches a man's penis with red nails4:00
Asian5/17/24

Paloma touches a man's penis with red nails

A man lies down outdoors in the sun. Paloma uses her hand to stroke his penis. She has long red nails that grip his skin. The shot focuses on the hand and th…

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Latina Ladyboy's Anal Outdoor Drilling4:00
Outdoor5/17/24

Latina Ladyboy's Anal Outdoor Drilling

Enjoy the wild side with a Latin Shemale dominating her partner in an outdoor anal drilling. Experience the thrill of forbidden pleasure and let your curiosi…

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Raw Ladyboy Action ~ Bottoms and Tops Outdoors4:00
Outdoor5/17/24

Raw Ladyboy Action ~ Bottoms and Tops Outdoors

Outdoor Shemale Bottoms and Tops Porn Video - Explore our collection of shemale porn videos with hot shemale bottoms and tops in outdoor settings. From muscu…

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Ladyboy Takes Control ~ Outdoor Ass Fucking4:00
Outdoor5/17/24

Ladyboy Takes Control ~ Outdoor Ass Fucking

Outdoor shemale sex with a man getting fucked from behind by a shemale sex partner. Explore our collection of shemale sex videos and see the ultimate pleasur…

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Busty Ladyboy Anal Sex Orgasm with Cumshots!4:00
Busty5/17/24

Busty Ladyboy Anal Sex Orgasm with Cumshots!

Busty shemales take pleasure in anal sex, with multiple cumshots to satisfy their desires. Experience the thrill of shemale sex and explore the world of tran…

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Ladyboy Cocksucker Bends Over for Anal Fun4:00
Anal5/17/24

Ladyboy Cocksucker Bends Over for Anal Fun

Watch the sensual shemale cocksucker as she bends over and gets ready for a thrilling butt fuck, making her anal hole tremble with delight. This is a must-se…

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Ladyboy Goddess with a Huge Ass Gobbles Cock4:00
Anal5/17/24

Ladyboy Goddess with a Huge Ass Gobbles Cock

Shemale with a big ass sucks dick - This sex video features a stunning shemale with an incredibly attractive big ass in action. Watch as she sucks dick with…

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BBC Pounds Ladyboy's Slutty Ass4:00
Anal5/17/24

BBC Pounds Ladyboy's Slutty Ass

Enjoy the ultimate BBC experience with a stunning shemale, as she opens up her slutty ass for an unforgettable ride. This exclusive video will leave you brea…

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Ladyboy's Hard Cock Dominates Threesome4:00
Threesome5/17/24

Ladyboy's Hard Cock Dominates Threesome

Shemale threesome sex video with male and female partners. Sit back and watch as the shemale's cock takes center stage in this erotic adventure!

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Ladyboy Fitness Queens Gangbang Him Outdoors4:00
Gangbang5/17/24

Ladyboy Fitness Queens Gangbang Him Outdoors

Relish in the sight of shemale fitness icons as they unleash their raw sexual energy on a lucky fellow in an outdoor adventure you won't soon forget. These s…

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Ladyboy Queen Fucks Anal to Perfection4:00
Anal5/17/24

Ladyboy Queen Fucks Anal to Perfection

Discover the art of shemale sex with this exclusive video featuring a gorgeous shemale chick as she shows off her incredible skills at pleasuring a lucky par…

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Ladyboy Latina with Big Tits Loves Doggystyle4:00
Latina5/17/24

Ladyboy Latina with Big Tits Loves Doggystyle

Get ready for a steamy latina tranny with big tits, getting down and dirty with doggystyle sex. This shemale is ready to fulfill your wildest fantasies and l…

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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.