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Longest Ladyboy Sex Video - Page 36

2,597 videos
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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Yasmin Rios gives a blowjob to a man5:00
Blowjob5/17/24

Yasmin Rios gives a blowjob to a man

Yasmin Rios lies with a man in a bedroom. She starts giving him a deep blowjob. She uses her mouth and hands on his penis. The scene shows her blonde hair 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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Two naked women posing on a white bed5:00
Asian5/17/24

Two naked women posing on a white bed

Two women are in a bedroom with a large bed. One woman lies on her back while the second woman sits on top of her. They both pose while naked on the white sh…

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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…

Watched
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…

Watched
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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Tamara gets a close up view of a penis5:00
Asian5/17/24

Tamara gets a close up view of a penis

Tamara lies on her back in a room. She looks up while her body is exposed. Her hands rest near her breasts. The camera focuses on the penis in the foreground.

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Jennifer gets fucked by a man on a purple bed5:00
Hardcore5/17/24

Jennifer gets fucked by a man on a purple bed

Jennifer lies on a purple bed wearing a black bra. A man stands over her and begins to have sex. They move together in a bedroom setting. The scene shows the…

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Suzanna Holmes rides a man on a bed5:00
Riding5/17/24

Suzanna Holmes rides a man on a bed

Suzanna Holmes and a man are in a bedroom. She wears black lingerie while they lay on the bed. She climbs on top of him to ride him. They continue having sex…

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Joyla Lisboa and a man naked on the floor5:00
Asian5/17/24

Joyla Lisboa and a man naked on the floor

Joyla Lisboa lies on a tiled floor in a bedroom. A man sits behind her while they touch. They stay close together on the ground. The scene shows them naked i…

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Thayla Andrade gives a blowjob to a shemale5:00
Blowjob5/17/24

Thayla Andrade gives a blowjob to a shemale

Thayla Andrade is in a room with a shemale. She starts giving a deep blowjob to the large penis. She uses her hands to hold the shaft while sucking. The scen…

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Blonde women posing naked in a bedroom5:00
Blonde5/17/24

Blonde women posing naked in a bedroom

Two blonde women are in a bedroom. They are both naked and standing near a bed. One woman leans forward while the other holds her waist. They look at the cam…

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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.