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Longest Ladyboy Sex Video - Page 6

2,964 videos
301–360 of 2,964
Ladyboy Dominates with Anal Doggy Style10:00
Femdom5/17/24

Ladyboy Dominates with Anal Doggy Style

Watch two shemales in a steamy anal doggy style session as they explore each other's bodies. Get ready for a wild ride as these two experts in the art of sex…

WatchedAnal
Ladyboy Fucks Insane Gays in Wild Orgy10:00
Hardcore5/17/24

Ladyboy Fucks Insane Gays in Wild Orgy

Relish in the raw and unbridled passion of shemales as they engage in a fiery erotic encounter with insatiable gays. Let yourself be transported to a world w…

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Ladyboy's wild threesome with a blissful couple10:00
Threesome5/17/24

Ladyboy's wild threesome with a blissful couple

Get ready for a wild ride with our shemale, as she brings a whole new level of excitement to the bedroom. Watch as she takes on two willing participants at o…

WatchedCouple
Ladyboy Babe Gets Anal Fucked on Camera10:00
Anal5/17/24

Ladyboy Babe Gets Anal Fucked on Camera

Intense shemale action! Watch as a gorgeous bleached babe receives anal sex from a dominant partner. Treat yourself to this forbidden fantasy and discover th…

Watched
Blonde Ladyboy Gives Blowjob for Black Dick10:00
Blowjob5/17/24

Blonde Ladyboy Gives Blowjob for Black Dick

Relish in the sight of a stunning blonde shemale as she performs oral sex on a large black dick. The sensual pleasure is palpable as the shemale intensely su…

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Ladyboy Domenique Takes Control of Cris's Cock10:00
Asian5/17/24

Ladyboy Domenique Takes Control of Cris's Cock

Shemale Domenique shows off her impressive blowjob skills in this steamy video, as she takes on Cris's massive hard dick with ease. With her stunning curves…

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Busty Ladyboy Threesome ~ 3D Fuck with Chick10:00
Threesome5/17/24

Busty Ladyboy Threesome ~ 3D Fuck with Chick

Pornhub presents the ultimate pleasure for fans of shemale porn. This 3D video features a hot busty shemale and a beautiful woman engaging in intense sexual…

WatchedBusty
Redhead Ladyboy Fucks Pretty Sexy Model10:00
Hardcore5/17/24

Redhead Ladyboy Fucks Pretty Sexy Model

Watch a redhead shemale in an intense sexual encounter with a beautiful model. This professional footage will leave you breathless as you witness the passion…

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Ladyboy with Fake Tits Gets Anal Pleasure10:00
Busty5/17/24

Ladyboy with Fake Tits Gets Anal Pleasure

Shemale is a term used to describe a transgender woman with male sex characteristics. In this sex video, a black shemale with fake tits gets her ass fucked b…

WatchedAnal
Ladyboy's Explosive Orgies with Hardcore Lovers10:00
Hardcore5/17/24

Ladyboy's Explosive Orgies with Hardcore Lovers

Starring a gorgeous shemale, this sex video will take you on a journey of raw, unbridled passion. Filled with intense, hardcore action, this video is not for…

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Ladyboy in Stockings Pounds Ass in Anal Sex10:00
Stockings5/17/24

Ladyboy in Stockings Pounds Ass in Anal Sex

Discover the tantalizing world of shemale sex videos. Our exclusive collection features sexy trannies in stockings engaging in wild anal sex that will leave…

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Ladyboy Lucia Matthews Sucks Off Her Lucky Guy10:00
Blowjob5/17/24

Ladyboy Lucia Matthews Sucks Off Her Lucky Guy

Enjoy the passionate sex video of beautiful Lucia Matthews, the seductive shemale who knows how to please her man. With her feminine curves and tantalizing m…

Watched
Leona's Black Ladyboy Blowjob ~ Sooooo Nice!10:00
Blowjob5/17/24

Leona's Black Ladyboy Blowjob ~ Sooooo Nice!

Discover the sensual world of black shemale Leona as she receives a tantalizing blowjob in this exclusive video. Explore the allure of shemales and let yours…

Watched
BDSM Threesome with Blonde Ladyboy in Stockings10:00
Threesome5/17/24

BDSM Threesome with Blonde Ladyboy in Stockings

Satisfy your cravings with this steamy shemale video featuring a blonde shemale wearing stockings in a BDSM threesome. Experience the ultimate pleasure from…

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Sensual Ladyboy Sucks Naughty Neighbor's Cock10:00
Blowjob5/17/24

Sensual Ladyboy Sucks Naughty Neighbor's Cock

Satisfy your cravings with our sweet shemale taking pleasure in sucking a nice dick. Get ready for the ultimate experience that will leave you breathless and…

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Naomi's Wild Ladyboy Romp with a Lucky Guy10:00
Asian5/17/24

Naomi's Wild Ladyboy Romp with a Lucky Guy

Satisfy your desires with the mesmerizing shemale Naomi Close as she engages in an erotic fuck fest with a lucky partner. Let your fantasies run wild with th…

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Ladyboy Double Penetration with Brunette Bliss10:00
Asian5/17/24

Ladyboy Double Penetration with Brunette Bliss

Relish in the tantalizing sight of two gorgeous shemales pounding the sensual brunette in this sizzling sex video. Experience the ultimate pleasure as these…

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Blonde woman gives a deep blowjob to a man10:00
Blowjob5/17/24

Blonde woman gives a deep blowjob to a man

A blonde woman is in an indoor room. She starts giving a blowjob to a man. She takes his penis deep into her mouth. The scene shows a close up of her face an…

Watched
Shemale in black stockings gets fucked by a man10:00
Stockings5/17/24

Shemale in black stockings gets fucked by a man

A woman wearing black stockings and lingerie is in a room. She stands with her back to the camera while a man is between her legs. They engage in hardcore se…

Watched
She-Male Trio ~ Sara T, Vivian & Co10:00
Asian5/17/24

She-Male Trio ~ Sara T, Vivian & Co

Sara T and Vivian are shemale sex goddesses, taking charge in this hot fuck fest with cocky babes. No limits or inhibitions, this steamy scene is not for the…

Watched
Ladyboy Amanda Mantovany's Anal Fuck Fest10:00
Anal5/17/24

Ladyboy Amanda Mantovany's Anal Fuck Fest

Experience the ultimate pleasure with the stunning fake-tit shemale Amanda Mantovany as she takes on anal sex like never before. With her irresistible curves…

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Brunette Ladyboy Camilla Jolie's Fiery Fucking10:00
Hardcore5/17/24

Brunette Ladyboy Camilla Jolie's Fiery Fucking

Brunette shemale Camilla Jolie is a vision of sexual prowess, her skills in pleasuring herself and her partners will leave you breathless. Watch as she explo…

Watched
Ladyboy's Irresistible Assets Get Pounded Hard10:00
Anal5/17/24

Ladyboy's Irresistible Assets Get Pounded Hard

Horny big tits tranny ass fucked hard - this video is a must-watch for all fans of shemale sex. Featuring a gorgeous tranny with big tits, you won't be able…

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Michelle in police cosplay gets a blowjob10:00
Blowjob5/17/24

Michelle in police cosplay gets a blowjob

Michelle wears a police outfit and fishnet stockings. She sits on a black chair indoors. A man performs a blowjob on her. He stays focused on her while she l…

Watched
Ladyboy's Seductive Blowjob Frenzy - 70 chars10:00
Blowjob5/17/24

Ladyboy's Seductive Blowjob Frenzy - 70 chars

Busty shemale is a term that describes an individual who was assigned male at birth but has completed gender confirmation surgery. If you're looking for vide…

Watched
Shemale and blonde woman kissing on a bed10:00
Blonde5/17/24

Shemale and blonde woman kissing on a bed

A blonde woman and a shemale sit on a bed together. They start by kissing deeply. The woman wears a black corset and fishnet stockings. They continue to hold…

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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.