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Longest Ladyboy Sex Video - Page 39

2,964 videos
Elegant Ladyboy with Small Tits Masturbates5:00
Busty5/17/24

Elegant Ladyboy with Small Tits Masturbates

Elegant Small Tits Shemale Masturbates - WATCH NOW! Discover the allure of shemales with elegant small tits as they pleasure themselves like never before. Ex…

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Ladyboy Natalie's Hot Dick Sucking Session5:00
Blowjob5/17/24

Ladyboy Natalie's Hot Dick Sucking Session

Shemale Natalie invites you to explore her world of sensual pleasures, as she welcomes you into her bedroom for an intimate encounter. Watch as she lavishly…

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Four Ladyboys Double Teamed Him For Anal Fun5:00
Anal5/17/24

Four Ladyboys Double Teamed Him For Anal Fun

Four shemales fuck him in the ass - Online video depicts a man receiving anal sex from four shemales, exploring the world of shemale sex and the pleasures it…

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Ladyboy's Tan Lines and Meaty Stick Action5:00
Asian5/17/24

Ladyboy's Tan Lines and Meaty Stick Action

Take a look at this steamy shemale video that will leave you breathless! Watch as she shows off her tan lines while blowing a meaty stick, then jumps on it w…

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Ladyboy Cop's Analrotting Virginity5:00
Anal5/17/24

Ladyboy Cop's Analrotting Virginity

Come and watch the sexiest and hottest shemale cop in action! Our ladyboy officer is ready to satisfy your wildest fantasies with her anal sex skills. You wo…

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Ladyboy May's Wild Wanking and Fucking Adventure5:00
Masturbation5/17/24

Ladyboy May's Wild Wanking and Fucking Adventure

Shemale May delights in her own pleasure as she wanks, and then invites you to watch her fuck herself to orgasm. With her perfect body and natural curves, sh…

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Sandy Ladyboy's Black Cock Fuck Fest5:00
Hardcore5/17/24

Sandy Ladyboy's Black Cock Fuck Fest

Sandy Shemale, the shemale queen, fucks with a massive black dick in this sex video. She seduces her partner with her beautiful curves and smooth skin, as th…

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Ladyboy in Fishnet Stockings Gets Anal Pleasure5:00
Stockings5/17/24

Ladyboy in Fishnet Stockings Gets Anal Pleasure

Watch as a stunning blonde shemale flaunts her curves in fishnet stockings while engaging in steamy anal play. This NSFW video is not for the faint of heart…

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Ladyboy Drills Hung Fucker till He Cums Hard5:00
Big Cock5/17/24

Ladyboy Drills Hung Fucker till He Cums Hard

Tanned fucker was drilled by a shemale - This sex video features a tanned stud being penetrated by a sexy shemale. Watch as they engage in passionate sex, wi…

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Cute Tanned Ladyboy Fabricia Sucks a Dick5:00
Blowjob5/17/24

Cute Tanned Ladyboy Fabricia Sucks a Dick

Relish in the sight of Cute tanned shemale Fabricia as she expertly performs oral sex on a hard dick. Her skills are not to be missed! Watch now and see exac…

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Ladyboy Gangbang Soccer Star's Wild Ride5:00
Gangbang5/17/24

Ladyboy Gangbang Soccer Star's Wild Ride

Welcome to the hottest shemale gangbang experience for soccer playing guys! Watch as our gorgeous shemales take turns pleasuring you in every way imaginable…

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Slim Ladyboy Fucks and Fists with Passion5:00
Hardcore5/17/24

Slim Ladyboy Fucks and Fists with Passion

Fisting and fucking a slim, shemale beauty - Watch as this stunning, feminine-looking shemale seductively entices her partner with her voluptuous curves and…

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Ladyboy Banging Black Dude in Sexy Threesome5:00
Threesome5/17/24

Ladyboy Banging Black Dude in Sexy Threesome

Relish in the raw passion of shemales as they boldly dominate their black partner in this sexually charged video. Experience the ultimate pleasure as these f…

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Ladyboy Pornstar with Fake Tits Gets Anal Fun5:00
Busty5/17/24

Ladyboy Pornstar with Fake Tits Gets Anal Fun

Discover the ultimate pleasure with our brunette shim with fake tits as she plays with her dick and indulges in hot anal action. Don't miss out on this eroti…

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Ladyboy Dominates with Anal Penetration5:00
Femdom5/17/24

Ladyboy Dominates with Anal Penetration

Shemale is a genderqueer term used to describe individuals who identify as neither entirely male nor female. In this video, a shemale takes control and bends…

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Ladyboy's Anal Thrill on the Deck Chair5:00
Anal5/17/24

Ladyboy's Anal Thrill on the Deck Chair

Discover the ultimate pleasure with our shemale performers, as they reveal their stunning curves and titillating moves. Get ready for an unforgettable experi…

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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.