6:58Femdom5/17/24
Ladyboy Domination ~ Ass-Fucking a Gagged Man
This video features a shemale taking charge in the bedroom as she unleashes her passion on an unsuspecting man. With her stunning curves and insatiable hunge…
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44Longest Ladyboy Sex Video - Page 16
2,967 videos6:58
6:58Asian5/17/24
Bride looks in a mirror while a photographer takes her picture
A woman wears a white wedding dress and veil. She holds a silver hand mirror to check her face. Another woman stands next to her and uses a camera to take ph…
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142
6:58Asian5/17/24
Jessica Fox uses a collar on a man in a latex outfit
Jessica Fox wears a brown latex bodysuit in a wooden room. She stands over a man wearing a leather collar. The man looks up at her while she holds him. They…
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51
6:58Asian5/17/24
Carley gives a handjob to a man on a bed
Carley sits on a bed in a bedroom. She holds a man's penis with both hands. She performs a handjob while looking at the camera. The man stays in a POV positi…
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56
6:58Asian5/17/24
Man and woman sitting together on a couch
A man and a woman sit on a grey couch in a living room. The woman wears a white sleeveless top and a light skirt. She smiles while sitting next to the man in…
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56
6:58Asian5/17/24
Man touches a naked redhead in a garden
A man and a woman are outside in a tropical garden. The woman is completely naked and shows her body. The man reaches out to touch her genitals. They stay cl…
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109
6:58Blonde5/17/24
Blonde woman and man in a kitchen with another woman
A blonde woman sits on a kitchen counter. A man sits between her and a dark haired woman. He leans in to kiss the dark haired woman. They all stay together i…
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62
6:58Busty5/17/24
Brunette with big tits gets fucked in doggy style
A brunette woman with big tits is in a white room. She wears black lingerie while a man penetrates her from behind. They move in doggy style on a surface. Th…
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127
6:58Asian5/17/24
Three naked women inside a yellow tent
Three women are inside a small yellow tent. The blonde woman on the left looks at her friends. The brunette woman holds her large breasts while sitting. They…
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72
6:58Blowjob5/17/24
Shemale gets a blowjob from a blonde woman in a group
Four women are in a room with a chalkboard. A blonde woman performs a blowjob on a shemale. The other women watch the action from nearby. The group stays tog…
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65
6:58Asian5/17/24
Brunette woman in green bodysuit pulls at her clothes
A brunette woman with tattoos stands in a room. She wears a lime green bodysuit. She looks down at the camera while pulling on her clothes. The shot shows he…
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67
6:58Blonde5/17/24
Blonde shemale with big tits sits on a man on the couch
A blonde woman and a man sit together on a couch. She wears a gold top and fishnet stockings. The man wears sunglasses and a black shirt. They pose closely f…
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56
6:58Asian5/17/24
Brittney Kade gets held by a man in a pink skirt
Brittney Kade and a man are in a bright room. The man holds her bare buttocks while she leans forward. She wears a pink skirt near a glass door. They stay cl…
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67
6:58Asian5/17/24
Two naked women posing together on a bed
Two women are in a bright bedroom. The brunette woman with tattoos crawls on all fours on the mattress. The blonde woman stands behind her and places her han…
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84
6:58Blonde5/17/24
Blonde woman watches as her friend gets her breasts touched in a sauna
Two women are inside a wooden sauna. A blonde woman in a purple towel sits and watches her friend. Another woman lies back while someone touches her big tits…
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60
6:58Blonde5/17/24
Blonde woman in white bodysuit lies on pink bed
A blonde woman lies on a pink bed in a room with pink lights. She wears a white bodysuit and pink high heels. The room has metal chains hanging from the ceil…
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64
6:58Asian5/17/24
Two naked women kissing on a bed
Two women lie together on a white bed. One woman leans over her partner to kiss her neck. They hold each other closely while naked. The scene stays focused o…
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75
6:58Blonde5/17/24
Two blonde women naked on a bed
Two blonde women are in a bedroom. One woman lies on her back on the bed. The other woman sits over her legs and holds them. They stay close together while n…
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81
6:58Blonde5/17/24
Tattooed blonde woman poses naked on a chair
A blonde woman with tattoos sits in a room. She is naked and shows her tattoos on her back and legs. She poses on a black chair near a display case. The room…
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96
6:58Outdoor5/17/24
Three women have fun in a public bathroom stall
Three women gather inside a white bathroom. A woman in a yellow top bends over a toilet. Another woman in red stands near the stall door. The third woman in…
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193
6:58Asian5/17/24
Three women relaxing on a sofa under pink lights
Three women sit together on a dark sofa. They are covered by a large pink blanket. Pink lights glow in the background behind them. The women look towards the…
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101
6:58Hardcore5/17/24
Naked woman gets fucked on a green sofa
A woman lies on a bright green sofa. A man holds her hips and moves inside her. She has her arms raised above her head. They continue the sex until the man f…
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115
6:58Threesome5/17/24
Blonde shemale and man have a threesome in a bedroom
A blonde woman with tattoos and black stockings sits on a man's back. The man performs anal sex on a second woman lying on the bed. They continue the hardcor…
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184
6:58Asian5/17/24
Tattooed woman in latex skirt performs doggy style on man
A woman wearing a black latex skirt and fishnet stockings is in a dark room. She gets on all fours over a man with tattoos. They engage in doggy style sex on…
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205
6:58Asian5/17/24
Brunette woman in yellow shirt touches a naked woman
A brunette woman wearing a yellow shirt sits in a room. She reaches out to touch the neck of a naked woman. The naked woman sits on a white sofa. They look a…
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206
6:57Asian5/17/24
Brooke Bangs gets her genitals handled by a man
Brooke Bangs lies on a bed wearing black lace panties. A man reaches down to touch her. He holds her large breasts and genitals. The scene shows her body up…
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58
6:57Blonde5/17/24
Blonde woman in black bodysuit stands near a man
A blonde woman wears a black bodysuit in a room with bare walls. She stands by a table while a man looks up at her. The man stays close to her legs. They are…
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89
6:57Busty5/17/24
Shemale with big tits wears fishnets and rides a man
A shemale with big tits and fishnet stockings is in a bedroom. She sits on top of a man to start riding him. They move into doggy style for anal sex. The man…
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95
6:57Masturbation5/17/24
Solo Asian shemale masturbates on a white sofa
A woman lies on a white sofa in her bedroom. She wears black stockings and a bracelet while looking at the camera. She uses her hand to masturbate her penis…
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136
6:57Asian5/17/24
Frenzied Ladyboy Rounds with Fishnets ~ Devouring Cock in Crazy Rounds!
Watch as an Asian shemale in sexy fishnets devours cock in a crazy round of sexual pleasure. Don't miss the intense moment where she swallows and cums, leavi…
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25
6:57Anal5/17/24
Ladyboy's Tight Ass Gets Roughly Fucked 'til Exhaustion
Man fucks tight shemale's ass until exhaustion - In this sex video, a man engages in rough sexual intercourse with a shemale, focusing on her tight asshole u…
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36
6:57Big Cock5/17/24
Ladyboy Pounded Hard in the Ass by Big Cock
Shemale Pleasure - Watch sexy shemales loudly begging for more cock into their ass. Get ready for intense orgasms and wild sex acts that will leave you wanti…
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26
6:57Asian5/17/24
Slutty Ladyboy Nun Nina Lawless Seduces Jailed Man ~ Nina's Sizzling Sinful Surprise!
Nina Lawless in a kinky role as a slutty nun! Watch her and a jailed man experiment with their desires and cross boundaries in this sexually charged video. F…
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30
6:57Femdom5/17/24
Ebony Ladyboy Dominates Her Man in Hot Anal Fuck Session
Watch incredibly addictive ebony shemale fucks her man in the ass until the last drops. This explicit sex video is not for the faint-hearted. The shemale's s…
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29
6:57Femdom5/17/24
She-Male Domination ~ MILF Ass Spanking and Slavery Treatment
Discover the world of shemale domination with this exclusive video of a dominant MILF who knows how to put her male slave in his place. Watch as she spanks h…
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34
6:57Asian5/17/24
Thin Ladyboy's Sultry Slutty Surge ~ Banging with the Best!
Looking for the hottest shemale sex video? Check out this steamy scene featuring a slutty thin shemale ready to bang! Get lost in the pleasure as she shows o…
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35
6:57Femdom5/17/24
Ladyboy Domination ~ Rough Anal Play with a Male Slave
Shemales are known for their powerful dominance in the bedroom, and this sex video is no exception. Featuring a hot shemale thoroughly dominating her male sl…
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35
6:57Asian5/17/24
Tattooed Ladyboy Ts Foxxy Gets Blown
Ts Foxxy, a gorgeous tattooed shemale, is truly in her element as she enjoys an intense blowjob. Her passionate moans are music to the ears of her lucky part…
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35
6:57Blonde5/17/24
Ravishing Ladyboy Seduces Thirsty Young Blonde with Dick Play
In this steamy scene, a sexually hungry young blonde is granted access to a wealth of dick by a lustful shemale. With such an abundance of phallus at her fin…
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35
6:57Anal5/17/24
Asian Ladyboy's Deep Anal Pleasure ~ Taboo or Temptation?
Asian shemale is a term used to describe a person who was assigned male at birth but identifies as female or as having both male and female genders. In this…
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35
6:57Asian5/17/24
Ladyboy Goddess Jessica Fox Ravishes Issueless Male's Anus!
Bringing you the hottest shemale porn videos, featuring Jessica Fox as she takes control and destroys her partner's asshole. Experience the ultimate pleasure…
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33
6:57Asian5/17/24
Ladyboy Mia Little and Natalie Mars' Steamy Locker Room Romp
Find yourself in awe as the gorgeous shemale Mia Little and the stunning Natalie Mars work up a sweat in the locker room. This steamy sex video is not to be…
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36
6:57Massage5/17/24
Ladyboy Pounded Hard in Private Nuru Massage Session
Discover the ultimate pleasure of shemale sex as this slutty babe takes on the biggest hammering she's ever had. Get ready for some intense action that will…
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36
6:57Cam5/17/24
Asian Ladyboy Queen Shows Off Huge Tits in Private Cam Solo
Watch now as an alluring Asian shemale with impressive curves and large breasts delights in a personal tranny cam solo. Get lost in the hypnotic movements of…
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36
6:57Blowjob5/17/24
Ravished by a Sexy Ladyboy ~ Anal and Oral Seduction
Strong anal and oral seduction with a shemale - Full HD video description ~
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39
6:57Threesome5/17/24
Chelsea Marie and Arielle Aquinas' Ladyboy to MILF Threesome
Sensual shemale Chelsea Marie teams up with experienced MILF Arielle Aquinas in a steamy lesbian adventure. The two beauties engage in passionate oral sex, t…
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36
6:57Blonde5/17/24
Blonde woman and tattooed man sitting together indoors
A blonde woman and a tattooed man sit in a bright room. They look directly at the camera and smile. The woman wears a purple striped top. They stay seated ne…
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49
6:57Blonde5/17/24
Blonde woman uses a pink dildo on a leather couch
A blonde woman sits on a black leather couch in a white room. She wears red lingerie and red eye makeup. She uses a pink dildo on her body while lying back…
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90
6:57Feet5/17/24
Ts Foxxy & Cytherea's Ladyboy Foot Job, Blow Job, Fingering, and Cream Pie
Shemale sex videos are always a thrilling experience, and this one is no exception! Starring Ts Foxxy and Cytherea, this foot job, blow job, fingering and cr…
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42
6:57Asian5/17/24
Two women in fairy cosplay sitting on a bed
Two women wear colorful fairy outfits in a bedroom. They sit together on a white bed. The woman in pink looks at the woman in purple. They pose for the camer…
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46
6:57Anal5/17/24
Ladyboy Sexperts ~ Seductive Anal Fantasy Revealed!
Get lost in a world of pure pleasure with our seductive shemale, who knows just how to fulfill your deepest desires. Experience the ultimate in anal pleasure…
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44
6:57Asian5/17/24
Three naked women play on a white couch
Three women are naked in a living room. A redhead woman lies on her back on a white couch. A blonde woman leans over her body. Another woman stands and touch…
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47
6:57Threesome5/17/24
Ladyboy's Irresistible Cock Steals the Spotlight in Restless Threesome
Shemale dominates this steamy threesome as a horny couple can't resist her irresistible charms. Amidst the restless action, the tranny's dick takes center st…
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45
6:57Asian5/17/24
Whipped by a Black Ladyboy ~ Thin Tranny Takes it Hard in the Backside
Satisfy your cravings for shemale action with this steamy scene of a black stud fucking a skinny tranny in the ass until she falls exhausted. Explore the wor…
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43
6:57Anal5/17/24
Tranny Temperature Rises with Intense Anal Seduction
Unleash your wildest fantasies with a seductive shemale, experienced in giving mind-blowing anal pleasure. Our busty tranny will blow your mind with her expe…
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45
6:57Blonde5/17/24
Blonde women and a dark haired woman in a white room
Three women are in a bright white room. A woman with dark hair kneels on a bed. Another woman sits beside her while a blonde woman stands close by. They are…
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50
6:57Riding5/17/24
Naked woman rides another woman on a bed
Two women are in a dark room with a bar. One woman is naked and climbs on top of the other. She rides her while the woman on the bottom lies face down. They…
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66
6:57Asian5/17/24
Two naked women posing on a red leather sofa
Two naked women are in a living room. They sit together on a red leather sofa. One woman leans back while the other sits up. They pose for the camera in the…
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65
6:57Asian5/17/24
Two naked women having sex on a white bed
Two women are in a room with white curtains. One woman lies on her back on a white bed. The second woman gets on top of her and rides her. They continue movi…
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68
6:57Asian5/17/24
Tattooed woman kisses a man in a tiled room
A tattooed woman and a man are in a room with white tiles. She leans in to kiss him closely. They stay close together while she holds his face. The scene sho…
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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.