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Longest Ladyboy Sex Video - Page 42

2,964 videos
Sweet Ladyboy's Hot Masturbation Session!5:00
Masturbation5/17/24

Sweet Ladyboy's Hot Masturbation Session!

Satisfy your cravings for the ultimate shemale experience with our explicit video of a stunning shemale in action. Watch as she teases and pleasures herself…

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Ladyboy Goddess Fucks Gay Boy Prodigy5:00
Hardcore5/17/24

Ladyboy Goddess Fucks Gay Boy Prodigy

Dominating dick of the seductive shemale penetrates the eager hole of the gay boy in this steamy sex video. Experience the ultimate pleasure of this taboo ho…

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Ladyboy Babe Samara Sucks Cock in the Bath5:00
Blowjob5/17/24

Ladyboy Babe Samara Sucks Cock in the Bath

Watch beautiful shemale Samara seductively suck a hard dick in the bathtub. This steamy scene is not to be missed! For those craving shemale porn, this video…

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Blonde Ladyboy's Slutty Cock Take5:00
Blonde5/17/24

Blonde Ladyboy's Slutty Cock Take

Blonde shemale is a term that has become increasingly popular in recent years, and for good reason. Our video featuring a blonde shemale taking cock like a s…

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Ladyboy Divas ~ Blonde vs5:00
Blonde5/17/24

Ladyboy Divas ~ Blonde vs

Watch the irresistible shemale blonde with curves and muscles that will blow your mind as she gets down with a muscular black dick. The perfect combination o…

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Chubby Ladyboy Fucking with One Dong5:00
Hardcore5/17/24

Chubby Ladyboy Fucking with One Dong

Shemales (a term used to describe female-to-male transgender individuals) are often misunderstood and underrepresented in society. However, this sex video ch…

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Ladyboy Babe Rims and Fucks Her Tight Asshole5:00
Anal5/17/24

Ladyboy Babe Rims and Fucks Her Tight Asshole

Watch as a delicious brunette shemale with a tight asshole gets drilled from side to side by a hung stud. The shim is ready and waiting for your eager eyes t…

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Brunette Ladyboy Fernanda's Dick Riding5:00
Riding5/17/24

Brunette Ladyboy Fernanda's Dick Riding

Brunette shemale Fernanda takes control in bed as she rides on the dick, providing an unforgettable experience for her partner. Get ready for some hot shemal…

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Male or Female, Ladyboy Dominates Both!5:00
Femdom5/17/24

Male or Female, Ladyboy Dominates Both!

Shemale Sex Video ~ Shemale Dominates Horny Girl in Wild Cunt Fuck - In this alpha shemale's video, she takes control of a petite girl and pounds her pussy w…

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Ladyboy Cum Slut Gets Black Rimjob5:00
Cumshot5/17/24

Ladyboy Cum Slut Gets Black Rimjob

Watch as a lean and muscular tranny with an impressive cock takes on a hung black stud in this steamy sex video. The shemale's curves and tattoos make for an…

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Tatted Ladyboy's Sensual Stroking Session5:00
Asian5/17/24

Tatted Ladyboy's Sensual Stroking Session

Watch as a stunning tanned shemale wanks her impressive dick in this steamy video. You won't want to miss a minute of this private solo session, where our sh…

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Sensual Brunette Ladyboy Gets Her Dick Sucked5:00
Blowjob5/17/24

Sensual Brunette Ladyboy Gets Her Dick Sucked

From flirty gazes to seductive moans, this sensual brunette shemale is a true pleasure seeker. As she allows her female lover to pleasure her with eager lips…

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Ladyboy Barbra's Asshole Fucked Raw5:00
Anal5/17/24

Ladyboy Barbra's Asshole Fucked Raw

Enjoy the hottest shemale action featuring sexy Barbra as she gets fucked in the asshole by her partner. Experience the ultimate sexual pleasure with this st…

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Sandy's Hardcore Ladyboy Anal Drilled5:00
Anal5/17/24

Sandy's Hardcore Ladyboy Anal Drilled

Sandy, the gorgeous shemale, takes on a hardcore anal adventure in a wild sex video that will leave you breathless. get ready to witness Sandy's insatiable a…

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Ladyboy's Assfucking Romp with Pretty Brunette5:00
Anal5/17/24

Ladyboy's Assfucking Romp with Pretty Brunette

Welcome to our sex video featuring a beautiful brunette shemale who is experiencing intense pleasure as she receives mind-blowing anal sex. Our shemale perfo…

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Dark-haired Ladyboy Mary Anne's Anal Fuck Fest5:00
Anal5/17/24

Dark-haired Ladyboy Mary Anne's Anal Fuck Fest

Watch the steamy scene of dark-haired shemale Mary Anne as she takes on her partner in a wild anal adventure. Get ready for intense penetration and mind-blow…

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Ladyboy Takes A Monster Cumshot5:00
Cumshot5/17/24

Ladyboy Takes A Monster Cumshot

Watch the hot shemale star in an incredible porn video, with a focus on her amazing ass taking a massive cumshot. The perfect match for fans of tranny porn w…

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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.