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Longest Ladyboy Sex Video - Page 29

2,967 videos
Ladyboy's Fierce Fuck Finish with Nasty Facial!5:00
Hardcore5/17/24

Ladyboy's Fierce Fuck Finish with Nasty Facial!

Shemale is a term that often refers to individuals who were assigned male at birth but have a feminine gender identity. In this video, we see a shemale perfo…

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Ladyboy Camille's Face Fucked to Perfection5:00
Hardcore5/17/24

Ladyboy Camille's Face Fucked to Perfection

Experience the ultimate sexual experience with our shemale star, Camillle. Watch as she takes on multiple partners and gets fucked in her face in this wild a…

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Ladyboy Rough Love for Inked Babe!5:00
Asian5/17/24

Ladyboy Rough Love for Inked Babe!

Watch as a tattooed guy gets his fill of a sexy shemale's assets after a steamy kiss. Get ready for a wild ride as this shemale takes control and gives it to…

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Ladyboy's Hardcore Anal Sex with a Lucky Guy5:00
Anal5/17/24

Ladyboy's Hardcore Anal Sex with a Lucky Guy

Experience the thrill of shemale sex with our busty blonde as she pleasures herself with a delicious dildo. Watch as she sucks and fucks herself to ecstasy…

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Slim Guy Gets Busted with Ladyboy' s Fat Cock5:00
Asian5/17/24

Slim Guy Gets Busted with Ladyboy' s Fat Cock

Stunningly seductive, our shemale performer captivates with her slender yet busty figure, as she engages in an erotic fucking session with a slim guy. Experi…

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Ladyboy's Anal Adventure with a Caped Lover5:00
Anal5/17/24

Ladyboy's Anal Adventure with a Caped Lover

Eager to explore their desire, a brunette shemale indulges in an intimate encounter with a man wearing a cap. As their passion heats up, they engage in a ste…

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Juicy Ladyboy Ass Fucked Raw in Anal Fun5:00
Anal5/17/24

Juicy Ladyboy Ass Fucked Raw in Anal Fun

Shemale is a term that is often associated with beautiful females who possess both male and female genitalia. In this sex video, we witness a stunning shemal…

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Ladyboy Dominatrix Gives BJ while Pounding Ass5:00
Femdom5/17/24

Ladyboy Dominatrix Gives BJ while Pounding Ass

Shemale Shim Latina brings explosive passion to this XXX video as she expertly pleasures her male partner with a blowjob and then takes control of the situat…

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Doggy Style with Ladyboy Goddess Leticia5:00
Asian5/17/24

Doggy Style with Ladyboy Goddess Leticia

Doggy style sex with the stunning shemale Leticia - watch her take control and show her skills in this steamy video. Don't miss out on this wild experience t…

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Ladyboy Latex Fetish ~ Tranny Ass Cum Play5:00
Cumshot5/17/24

Ladyboy Latex Fetish ~ Tranny Ass Cum Play

Watch the irresistible shemale in action as she takes on multiple partners and leaves them breathless with her stunning performance. The video is not for the…

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Ladyboy On Leather ~ Fucking on the Sofa5:00
Hardcore5/17/24

Ladyboy On Leather ~ Fucking on the Sofa

Embrace the erotic world of shemales as they pleasure each other on a luxurious leather sofa. Explore the thrilling passion and raw desire of these beautiful…

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Ladyboy Seductress ~ Hot Girl on Girl Action5:00
Asian5/17/24

Ladyboy Seductress ~ Hot Girl on Girl Action

Shemale is a term used to describe a transgender individual with male genitalia. In this sex video, the shemale beauty enjoys an intimate encounter with a ho…

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Busty Ladyboy's Steamy Romp with Meaty Pole5:00
Busty5/17/24

Busty Ladyboy's Steamy Romp with Meaty Pole

Busty shemale is a term often used to describe a transgender individual with a larger chest size. In this sex video, the busty shemale takes center stage as…

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Ladyboy in Sinful Doggy Style - Adults Only!5:00
Asian5/17/24

Ladyboy in Sinful Doggy Style - Adults Only!

For an intense and steamy experience, watch this shemale fuck in doggy style. The video features a gorgeous pre-op transsexual with a stunning body and impre…

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Ladyboy's Stiff Dick Stroked in Sexy Video5:00
Asian5/17/24

Ladyboy's Stiff Dick Stroked in Sexy Video

Shemale porn is getting more popular than ever before! In this video, a stunning transsexual model with a rock hard cock uses her skills to pleasure herself…

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Tiny Tranny Tits Take Down in the Bottom5:00
Busty5/17/24

Tiny Tranny Tits Take Down in the Bottom

Watch as the gorgeous shemale with the tiniest tits takes on two partners in a steamy threesome. The tranny lays in the bottom, taking both partners at once…

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Ladyboy Fucks Tanned Dick ~ Sweet Porn Treat!5:00
Hardcore5/17/24

Ladyboy Fucks Tanned Dick ~ Sweet Porn Treat!

Enjoy a steamy sex video featuring a bold and beautiful shemale, with smooth curves and hot curves waiting to be explored. This tantalizing tape shows a tann…

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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.