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Longest Ladyboy Sex Video - Page 21

2,967 videos
Hentai man fucks woman from behind on a bed6:00
Hardcore5/17/24

Hentai man fucks woman from behind on a bed

A man and a woman are in a bright room. The woman stays on all fours on a white bed. He enters her from behind. They continue the sex on the mattress.

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Ladyboy Dominates Gay Male in Rough Anal Play6:00
Femdom5/17/24

Ladyboy Dominates Gay Male in Rough Anal Play

Shemale is a term that refers to a transgender individual who was born with male genitalia but identifies as female. In this video, a shemale takes on a gay…

WatchedAnal
Gorgeous Ladyboy Seduces with Intense Hard Sex6:00
Asian5/17/24

Gorgeous Ladyboy Seduces with Intense Hard Sex

Stunning hard sex for a gorgeous cock sucking shemale - This sex video features a beautiful and sensual shemale who will leave you breathless with her stunni…

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Zariah Aura gives Michael Delray a blowjob6:00
Blowjob5/17/24

Zariah Aura gives Michael Delray a blowjob

Michael Delray and Zariah Aura are together in a room. Zariah Aura performs a blowjob on him. She uses her mouth to pleasure him. The scene shows them close…

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Tanned Ladyboy Hottie's Solo Jerk Off Session6:00
Masturbation5/17/24

Tanned Ladyboy Hottie's Solo Jerk Off Session

Get ready for a mind-blowing full jerk off solo session by a tanned shemale hottie. Watch as she teases and pleasures herself with her own hands, leaving you…

WatchedSolo
Blonde shemale performs anal sex on a bed6:00
Blonde5/17/24

Blonde shemale performs anal sex on a bed

A blonde shemale wears leopard print and black lace lingerie. She lies on a bed in a bright room. She performs anal sex on a partner. The scene shows her fro…

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Blonde shemale masturbates on a bed, Group16:00
Blonde5/17/24

Blonde shemale masturbates on a bed, Group1

A blonde shemale sits on a bed in a bedroom. She has big fake tits and long hair. She holds her penis and masturbates herself. She looks at the camera while…

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Naked woman with big tits and man in bedroom6:00
Busty5/17/24

Naked woman with big tits and man in bedroom

A woman and a man stand together in a bedroom. She is naked and shows her big tits to the camera. The man holds her waist while they look at each other. They…

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Group sex with a naked woman and three men6:00
Asian5/17/24

Group sex with a naked woman and three men

A naked woman sits on a man's lap during a group sex session. Three men surround her while she stays in the center. They engage in various sexual acts togeth…

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Naked woman posing on a bed in a bedroom6:00
Asian5/17/24

Naked woman posing on a bed in a bedroom

A naked woman lies on a white bed. She looks back over her shoulder at the camera. The room has yellow curtains in the background. She stays in a crawling po…

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Blonde shemale and man relaxing on a bed6:00
Blonde5/17/24

Blonde shemale and man relaxing on a bed

A man and a blonde shemale lie on a bed in a bedroom. The man wears a black shirt and glasses. The shemale wears a grey sweater and black stockings. They sta…

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Brunette shemale rides a man on a red sofa6:00
Riding5/17/24

Brunette shemale rides a man on a red sofa

A brunette shemale sits on a man's lap on a red sofa. They start by hugging and kissing each other. She moves her body against him while they stay close. The…

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Redhead woman gets rimjob from man on bed6:00
Asian5/17/24

Redhead woman gets rimjob from man on bed

A man and a redhead woman are on a bed. The man leans over her to give her a rimjob. She lies on her stomach while he focuses on her. They continue their ses…

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Blonde woman and man sit on a sofa together6:00
Blonde5/17/24

Blonde woman and man sit on a sofa together

A blonde woman and a man sit on a grey sofa. She looks at her phone while he looks at her. They are in a bright room with white walls. The man wears a black…

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Brunette shemale masturbates on a white sofa6:00
Masturbation5/17/24

Brunette shemale masturbates on a white sofa

A brunette woman lies back on a white sofa. She wears black lace lingerie and fishnet stockings. She uses her hand to stroke her penis. The scene shows her e…

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Naked man has sex with a woman on a bed6:00
Asian5/17/24

Naked man has sex with a woman on a bed

A man and a woman are in a bedroom. The woman lies on the bed while the man moves over her. They engage in sex together on the mattress. The scene takes plac…

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Naked woman rides a man on a sofa6:00
Riding5/17/24

Naked woman rides a man on a sofa

A naked woman sits on a man's lap on a grey sofa. They face each other in a bright room. The woman moves her body on top of him. They stay close together on…

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Shemale in pink lingerie poses on a bed6:00
Lingerie5/17/24

Shemale in pink lingerie poses on a bed

A woman with big tits lies on a pink bed. She wears pink lingerie and white stockings. She poses while looking at the camera. The scene takes place in a brig…

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Woman in red tank top kisses a man6:00
Asian5/17/24

Woman in red tank top kisses a man

A woman and a man are together in a bright room. She wears a red tank top while they lean in close. They share a deep kiss. The man holds her as they continu…

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Koko T masturbates on a bed in her bedroom6:00
Masturbation5/17/24

Koko T masturbates on a bed in her bedroom

Koko T lies on a white bed in her bedroom. She has long brunette hair and blue nails. She uses her hands to touch her penis and anus. She continues to mastur…

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Two women have sex on a bed6:00
Asian5/17/24

Two women have sex on a bed

Two women are in a bedroom. One woman lies on her back with her legs up. The second woman leans over her body. They continue to touch each other on the bed.

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Spencer Fox and a woman on a bed6:00
Asian5/17/24

Spencer Fox and a woman on a bed

Spencer Fox lies on a white bed with a woman. She wears a zebra print top while they look at each other. The man has tattoos on his arm and leans in close. T…

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Zoe Sparx and Chanel Santini pose in lingerie6:00
Lingerie5/17/24

Zoe Sparx and Chanel Santini pose in lingerie

Zoe Sparx and Chanel Santini are in a bright bedroom. Zoe Sparx wears a hat and a striped top while looking at the camera. Chanel Santini poses in pink linge…

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Two blonde women have sex with a man on a bed6:00
Blonde5/17/24

Two blonde women have sex with a man on a bed

Two blonde women and a man are in a bedroom. One woman sits on the man while the other woman leans over her. They move together on the bed. The group continu…

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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.