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Longest Ladyboy Sex Video - Page 3

2,964 videos
Ladyboy Stars in Gruesome Group Sex Debauchery10:00
Asian5/17/24

Ladyboy Stars in Gruesome Group Sex Debauchery

Group sex starring shemales - FREE shemale sex video featuring an exclusive group sex scene with shemales. Watch hot shemale porn stars fuck and suck their w…

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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's Hot Blowjob ~ Stunning Sex Video10:00
Blowjob5/17/24

Ladyboy's Hot Blowjob ~ Stunning Sex Video

Find full-length sex videos featuring gorgeous shemales and their lovers in intimate moments. Watch as these stunning shemales tease, please and get pleasure…

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Ladyboy's Hard Dick Gets Sucked to the Bone10:00
Blowjob5/17/24

Ladyboy's Hard Dick Gets Sucked to the Bone

Shemale is a term used to describe a female-to-male transgender individual. In this video, a hot shemale is seen getting her dick sucked by an eager partner…

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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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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…

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Ladyboy's Sweet Blowjob for a Big Black Cock10:00
Blowjob5/17/24

Ladyboy's Sweet Blowjob for a Big Black Cock

Discover the intense pleasures of a shemale encounter. Our captivating blonde babe is a true master at providing mind-blowing blowjobs. Watch as she takes on…

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Tattooed Ladyboy Pounded Anal Senseless10:00
Anal5/17/24

Tattooed Ladyboy Pounded Anal Senseless

Brace yourself for a wild ride as our inked babe shemale taking charge and showing off her skills by fucking in her anal hole. Get ready for a mind-blowing e…

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Ladyboy's Hot Blowjob ~ Dripping with Cum10:00
Blowjob5/17/24

Ladyboy's Hot Blowjob ~ Dripping with Cum

Our sex video features a gorgeous shemale with a stiff dick in her mouth, ready to pleasure any man who dares to come close. Her feminine curves and alluring…

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Ladyboy Goddess Fucks Brunette Ass10:00
Anal5/17/24

Ladyboy Goddess Fucks Brunette Ass

Satisfy your sexual desires with the seductive shemale brunette who tantalizes with her feminine curves and mesmerizes with her irresistible ass. Experience…

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Ladyboy Destroyed in Anal Pleasure10:00
Anal5/17/24

Ladyboy Destroyed in Anal Pleasure

Experience the ultimate pleasure with our 3D shemale video, where she gets fucked in her anal hole. Our shemale is ready to indulge your desires and take you…

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Ladyboy Blowjob ~ Pleasure for Him and Her10:00
Blowjob5/17/24

Ladyboy Blowjob ~ Pleasure for Him and Her

Discover the ultimate experience of a seductive shemale who knows how to please her partner with her irresistible charm and talent. Watch as she performs a m…

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Ladyboy's Explosive Orgasm after Blowing Cock10:00
Asian5/17/24

Ladyboy's Explosive Orgasm after Blowing Cock

Shemale dominates the screen in this explicit video, taking control of a hard cock before expertly deep-throating it. The tension builds as she moans in plea…

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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…

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Busty Ladyboy's Anal Booty Gets Pounded10:00
Busty5/17/24

Busty Ladyboy's Anal Booty Gets Pounded

Watch as a stunning busty shemale takes on a big cock in her anal booty. Experience the thrill of shemale sex videos that will leave you wanting more. Explor…

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Tiny Tits Meet Big Dick in Ladyboy Anal Romp10:00
Busty5/17/24

Tiny Tits Meet Big Dick in Ladyboy Anal Romp

Teighjianna, a stunning ts pornstar with small tits, invites you to witness her anal sex adventure. Get ready to watch her performing mind-blowing anal sex m…

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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…

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Ebony Ladyboy dominant in White Frenzy10:00
Femdom5/17/24

Ebony Ladyboy dominant in White Frenzy

Welcome to our sex video featuring a hardcore ebony shemale fuck with a white dude. Our shemale performer will take you on a wild ride with her massive breas…

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Sultry Ladyboy Marcella's Anal Fucking Debut10:00
Anal5/17/24

Sultry Ladyboy Marcella's Anal Fucking Debut

Welcome to a world of forbidden pleasure where gender norms are broken, and desires take flight. Step into this taboo world where a stunning shemale named Ma…

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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.