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Longest Ladyboy Sex Video - Page 2

2,964 videos
61–120 of 2,964
Busty Ladyboy's Anal Craving ~ A XXX Experience11:57
Busty5/17/24

Busty Ladyboy's Anal Craving ~ A XXX Experience

In this raw and intense porn video, a gorgeous shemale with an insatiable hunger for anal pleasure, takes control of her partner's body. With firm hands and…

WatchedAnal
Two women posing on a bed in a bedroom11:57
Asian5/17/24

Two women posing on a bed in a bedroom

Two women are in a bedroom on a white bed. The brunette woman wears a blue mesh top and kneels. The other woman lies on her stomach next to her. They look at…

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Shemale in stockings performs a rimjob on a bed11:56
Stockings5/17/24

Shemale in stockings performs a rimjob on a bed

A naked woman lies on a bed in a bright room. She wears black fishnet stockings and high heels. She arches her back to perform a rimjob on herself. The scene…

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Blonde woman sits on bed next to naked woman11:56
Blonde5/17/24

Blonde woman sits on bed next to naked woman

A blonde woman sits on a bed in a bedroom. She looks toward the naked woman lying down. The woman on the bed has long hair and jewelry. They are both in a ro…

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Blonde tattooed woman poses naked on a bed11:56
Blonde5/17/24

Blonde tattooed woman poses naked on a bed

A blonde woman with many tattoos lies on a white bed. She looks toward the camera while posing. Her body is completely naked in the room. The scene shows her…

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Ladyboy Seductresses in a Steamy Threesome11:56
Threesome5/17/24

Ladyboy Seductresses in a Steamy Threesome

Watch as two sexy slutty females engage in a steamy make-out session with a seductive tranny in an unforgettable threesome. The tranny's stunning curves and…

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Four naked women posing together in a bedroom11:56
Asian5/17/24

Four naked women posing together in a bedroom

Four women gather in a white bedroom. A blonde woman lies on the bed while her friends stand nearby. They pose together without any clothes on. The group sta…

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Two naked women sit on a bed together11:56
Asian5/17/24

Two naked women sit on a bed together

Two women are in a bright bedroom. They sit together on a grey bed. One woman leans back while the other holds her. They touch each other's skin in the room.

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Ladyboy Khloe Kay's Rough Anal Penetration11:56
Anal5/17/24

Ladyboy Khloe Kay's Rough Anal Penetration

Relish in the intense pleasure of Khloe Kay, a stunning shemale with a small yet impressive dick that will blow your mind. Experience the thrill of watching…

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Two naked women touch each other on a bed11:56
Asian5/17/24

Two naked women touch each other on a bed

Two women are in a bedroom. The woman with dark hair lies on top of the redhead. They touch each other while laying on the bed. The woman on the bottom wears…

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Three women with colored hair hug in a bedroom11:56
Asian5/17/24

Three women with colored hair hug in a bedroom

Three women are together in a bedroom. A woman with bright red hair leans in toward the others. The blonde woman and the orange haired woman embrace her. The…

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Blonde woman rides brunette on a white sofa11:56
Blonde5/17/24

Blonde woman rides brunette on a white sofa

Two naked women are on a white sofa in a bright room. A blonde woman gets on top of a brunette woman. She rides her in a cowgirl position while they hold eac…

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Wild Ladyboy Escapades in X-Rated Naked Fun11:55
Asian5/17/24

Wild Ladyboy Escapades in X-Rated Naked Fun

Welcome to the ultimate shemale sex experience! Get ready for a wild ride as you watch the hottest shemale in town take control in the bedroom. From nude per…

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Ladyboy Homemade Porn ~ Insane Oral Scenes!11:55
Blowjob5/17/24

Ladyboy Homemade Porn ~ Insane Oral Scenes!

Looking for the hottest shemale porn videos? Our homemade collection features shemales in crazy scenes of oral and anal sex that will leave you breathless. F…

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Two women perform a rimjob on a white couch11:55
Asian5/17/24

Two women perform a rimjob on a white couch

Two women are on a white couch in a bright room. A redhead in black lace lingerie lies back against a blue pillow. Her partner performs a rimjob while they b…

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Alexa Scout uses a pink toy on a penis11:55
Toys5/17/24

Alexa Scout uses a pink toy on a penis

Alexa Scout is alone in a room. She wears fishnet stockings and holds a pink toy. The toy rubs against a penis. She continues the masturbation until the end.

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Marissa Minx kisses a man in a white shirt11:55
Asian5/17/24

Marissa Minx kisses a man in a white shirt

Marissa Minx and a man are in a room with white cabinets. They lean in close to each other. The man holds her face while they kiss. They stay close together…

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Four women and a man have sex outdoors11:55
Outdoor5/17/24

Four women and a man have sex outdoors

A group of women and a man gather outside at night. The redhead with tattoos touches the blonde woman. They all interact together in the yard. The group cont…

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Ladyboy Pounded in Rough Manners by Hot Lad11:54
Asian5/17/24

Ladyboy Pounded in Rough Manners by Hot Lad

Strap-on sex session with a shemale, enjoying unbridled passion and kinky pleasure. Watch as they explore each other's bodies, engaging in rough sex acts tha…

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Slutty Ladyboy's Anal Pleasure Session11:53
Anal5/17/24

Slutty Ladyboy's Anal Pleasure Session

Ever wanted to witness a slutty shemale taking things to the extreme? Look no further than this sex video where she takes it up the ass like a pro. With her…

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Three women in lingerie play on a sofa11:52
Lingerie5/17/24

Three women in lingerie play on a sofa

Three women are on a grey sofa in a living room. A redhead in black lingerie lies back while another woman holds her face. A blonde woman joins them on the c…

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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.