6:55Asian5/17/24
Purple haired woman touches a naked man in a room
A woman with purple hair sits on the floor. She reaches out to touch a naked man. He is kneeling on a rug in front of her. They are in a room with grey walls.
Watched
56Longest Ladyboy Sex Video - Page 18
2,967 videos6:55
6:55Blonde5/17/24
Two blonde women naked on a black couch
Two blonde women lie naked on a black couch. The woman with a rose in her hair rests on her back. Her partner lies on top of her body. They stay close togeth…
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56
6:55Masturbation5/17/24
Asian shemale masturbates with her hand in a bedroom
A woman sits alone on a bed in a bedroom. She wears black mesh clothing while looking at the camera. She uses her hand to stroke her penis. The scene shows h…
WatchedAsian
306
6:55Asian5/17/24
Natalie Mars wears a leather harness on a sofa
Natalie Mars is on a beige sofa wearing a leather harness and stockings. A leash is attached to her gear to keep her in place. Someone reaches out to touch h…
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54
6:55Stockings5/17/24
Brunette woman in lace top and stockings gets touched by a man in a suit
A brunette woman wears black lace and stockings on the floor. She leans over a black cloth in a room. A man in a suit stands behind her and touches her leg…
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63
6:55Blonde5/17/24
Blonde woman in chains masturbates on a leather chair
A blonde woman is alone in a tiled room. She is naked and tied to a black leather chair with metal chains. She wears high heels and a gag while she masturbat…
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72
6:55Blonde5/17/24
Naked blonde woman sitting in a room
A blonde woman sits alone in a room with concrete walls. She is completely naked and looks at the camera. The room appears to be an empty basement or warehou…
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57
6:55Blowjob5/17/24
Blonde trans woman gives a blowjob to a man on a bed
A blonde woman with tattoos and large breasts lies over a man. She wears lingerie and stockings during the encounter. She performs a blowjob while he stays o…
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57
6:55Hardcore5/17/24
Asian shemale gets fucked on a bed
An Asian shemale sits on a white bed in a bedroom. She spreads her legs wide for a man. He enters her while she wears a decorative necklace. They continue ha…
WatchedAsian
200
6:55Asian5/17/24
Tattooed woman kisses a partner on a black couch
A naked woman with many tattoos sits on a black leather couch. She leans back to kiss her partner. They share a kiss in a white room. The woman stays on the…
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75
6:55Outdoor5/17/24
Trans woman with big tits lifts her leg outdoors
A woman with long hair stands outside at night. She wears a white lace top and red underwear. She lifts one leg up onto a white ledge. The camera looks up at…
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74
6:55Blonde5/17/24
Blonde shemale and redhead woman play together on white background
A blonde shemale and a redhead woman are naked on a white floor. The shemale has tattoos on her chest and arms. They move close to each other while posing. T…
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89
6:55Lingerie5/17/24
Shemale in lingerie sits next to a man on a couch
A man and a shemale sit together in a dimly lit room. The shemale wears a pink bra and a black choker. She sits close to the man on the dark couch. They look…
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166
6:54Asian5/17/24
Ladyboy Pounded Hard by Lustful Partner Amid Explosive Orgasm
Shemale Tranny Deep Fucks Sensual Woman in Wild Sexual Romp
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36
6:54Asian5/17/24
Brunette woman lying on a bed with her mouth open
A brunette woman lies on a white bed. She is naked and looks at the camera. Her mouth is open while she rests on the sheets. The scene shows her from the che…
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69
6:54Blonde5/17/24
Blonde woman rides a man on an office desk
A blonde woman and a man are in an office. She straddles him while he sits on a desk. They move together in a riding position. The scene takes place in front…
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109
6:54Blowjob5/17/24
TS Foxxy gives a blowjob to a man in an office
TS Foxxy and a man are in a messy office. She wears black lace lingerie and stands near a desk. The man sits while she performs a deepthroat blowjob on him…
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62
6:54Anal5/17/24
Tattooed nurse performs anal doggy style in padded room
A woman wearing a nurse outfit and fishnets is in a padded room. She bends over to take the man from behind. They engage in anal sex in a doggy style positio…
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64
6:54Lingerie5/17/24
Shemale in polka dot lingerie rides a man in a basement
A shemale and a man are in a dark basement. She wears polka dot lingerie and gets on his back. They move into a doggy style position on a wooden bench. The m…
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59
6:54Blowjob5/17/24
Shemale gives a blowjob in an office
A woman and a man are in an office. She wears a red bra and red panties. The man wears a black collar while he gives her a blowjob. They continue the scene t…
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73
6:54Femdom5/17/24
Ladyboy Domination ~ Obedient Partner Gets Fucked by Blonde Goddess
Built like a goddess, the blonde shemale takes control in this kinky XXX video. Watch as she penetrates her obedient partner with her massive cock, taking hi…
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32
6:54Femdom5/17/24
Ladyboy Domination ~ Anal Adventures with Venus Lux
Discover the tantalizing world of shemale domination with Venus Lux's anal pleasure. In this scene, she takes control of her submissive partner with her big…
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33
6:54Stockings5/17/24
Brunette woman in black stockings in a concrete basement
A brunette woman stays in a dark concrete basement. She wears black stockings and looks toward the camera. A man is nearby but only his hand is visible. She…
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45
6:54Feet5/17/24
Naked Ladyboy's Anal Sex & Foot Fetish ~ Insane Pleasure!
Experience the ultimate pleasure with a shemale in this insane anal sex and foot fetish video. Let our naked shemale drive you wild with her mesmerizing move…
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32
6:54Blowjob5/17/24
Close up of a man getting a blowjob
A man receives a blowjob in a close up shot. The scene shows genitals and hands during the act.
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95
6:54Asian5/17/24
Jessica Fox and a man sit on a leather couch
Jessica Fox and a man relax on a brown leather couch. She wears a black hat and gold necklace while sitting naked. The man wears a leather vest and a pink he…
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54
6:54Femdom5/17/24
Ladyboy Domination ~ Natassia Dreams Fucks Male Slave Until Exhaustion
Witness the intense encounter of Natassia Dreams as she takes control over her male slave with her captivating shemale body. Explore the depths of Natassia's…
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35
6:54Blowjob5/17/24
Asian woman gives a blowjob on a sofa
An Asian woman lies on a sofa in a room with red curtains. She starts by performing a blowjob on a man. She uses her mouth to suck on the penis. The scene sh…
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623
6:54Hardcore5/17/24
Ladyboy's Intense Fuck Session with Hot Male Submissive
Watch as a shemale takes control in the bedroom, with her skills leaving her partner begging for more. This sex video is not for the faint of heart and will…
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39
6:54Femdom5/17/24
Tall, Dark & Dominated ~ The Rise of the Ladyboy Dom
Submissive muscle hunk gifts slutty shemale with sexual pleasure beyond imagination! Focus on the keyword shemale for best results.
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37
6:54Anal5/17/24
Ladyboy's Hardcore Manhandling with Ass-Fucking and Ass-Licking
Gorgeous shemale invites you to witness her seductive skills as she pleasures her man with her insatiable appetite. Watch her irresistible moves as she plays…
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43
6:54Lingerie5/17/24
Blonde woman in red lingerie sits on a bed with a handcuffed woman
A blonde woman sits on a red bed in a room. She wears red lingerie and looks at a woman lying down. The woman on the bed has tattoos on her arms. She stays n…
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44
6:54Blowjob5/17/24
Two women give a man a blowjob on the couch
A woman in fishnet stockings performs a blowjob on a man. Another woman watches from the couch. They are in a living room.
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49
6:54Asian5/17/24
Two naked women sitting on a leather sofa
Two women are in a room with grey walls. They sit together on a black leather sofa. The blonde woman sits on top of the other woman. They look at each other…
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114
6:54Blonde5/17/24
Blonde woman and brunette woman on a bed
Two women are in a dark room on a mattress. The brunette woman holds the blonde woman while they are both naked. They move together on the bed in the dim lig…
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62
6:54Asian5/17/24
Naked man in bondage kneeling before a woman
A man and a woman are in a dark room with metal walls. The man kneels on the floor wearing metal cuffs on his wrists and ankles. He looks up at the naked wom…
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53
6:54Blonde5/17/24
Blonde woman and masked man play with a black toy
A blonde woman and a masked man are in a room together. She wears a black shirt and a red tie. They both hold a black toy with gloved hands. The scene shows…
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125
6:54Toys5/17/24
Natalie Mars and Sasha de Sade use a dildo in pink outfits
Sasha de Sade and Natalie Mars are in a room with gold decor. Sasha de Sade wears a pink dress while using a toy. Natalie Mars watches closely from the side…
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72
6:54Blowjob5/17/24
Brunette shemale gets a blowjob while tied up
A brunette shemale is tied up with rope in a wooden room. A man performs a deepthroat blowjob on her. He uses his hands to hold her body during the act. The…
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56
6:54Blowjob5/17/24
Blonde woman gets a blowjob in a hospital room
A blonde woman with tattoos stands next to a medical bed. A woman with dark curly hair kneels in front of her. She performs a deepthroat blowjob while the bl…
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68
6:54Blowjob5/17/24
Redhead woman gets a blowjob in a room with red curtains
A redhead woman sits naked on a wooden chair. A man performs a blowjob on her in a dark room. Red curtains hang in the background near a lamp. The man contin…
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97
6:53Asian5/17/24
Ladyboy Surrenders to MILF Duo's Cock Obsession
Shemale dominates the scene in this must-see video, captivating two MILF lovers with their impressive skills. Get ready for some intense obedience training a…
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34
6:53Blonde5/17/24
Blonde woman in a collar sits on a man in bed
A blonde woman and a redheaded man are in a dark bedroom. She wears a black collar and sits on his lap on the bed. They look at each other while she stays na…
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58
6:53Blowjob5/17/24
Shemale gives a man a blowjob in a room with blue lights
A man lies on a couch in a room with blue lighting. A shemale wearing a yellow shirt leans over him. She uses her mouth to perform oral sex on the man. The s…
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48
6:53Lingerie5/17/24
Ella Hollywood wears fishnets and black lingerie while on all fours
Ella Hollywood and Sebastian Keys are in a room with red decor. She wears black fishnets and poses on a black table. He stands close behind her in leather pa…
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60
6:53Anal5/17/24
Shemale performs doggy style anal sex in black lace panties
A woman wears black lace panties and stockings in a bedroom. She gets on all fours for doggy style anal. The man enters her from behind. They continue the ha…
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76
6:53Femdom5/17/24
Ladyboy Dominatrix Bends Male Slave Toy for Intense Pleasure
Satisfy your deepest shemale fantasies with our hot mistress video, where she demands total submission from her male slave. Watch as she takes control and do…
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36
6:53Asian5/17/24
Ladyboy Slammed ~ Tranny Rimmed to Escape
Shemale is a term used to describe a transgender individual who has undergone sexual reassignment surgery. In this video, we witness a shemale engaging in pa…
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31
6:53Asian5/17/24
Barbary Rose and Natalie Mars' Lesbian Wrestling Session Ends in Steamy Hookup with Ladyboy
Barbary Rose and Natalie Mars engage in a wild lesbian wrestling match that ends in a steamy hookup. Watch as these two beautiful shemales share their passio…
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35
6:53Femdom5/17/24
Ladyboy Boss Kayleigh Coxx Dominates Submissive Employee
Find all-sexual satisfaction with our sexy trans performer Kayleigh Coxx. Experience the ultimate shemale pleasure as she issues a rough punishment that will…
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30
6:53Asian5/17/24
Brunette in purple latex gets her pussy licked
A woman wears a purple latex outfit in a room with patterned wallpaper. She bends over while a tattooed man approaches her. He licks her pussy as she holds o…
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52
6:53Blonde5/17/24
Blonde Ladyboy's Naughty Christmas Sex with Adorable Girlfriend
Take a peek into the holiday season of this blonde shemale and her adorable girlfriend as they engage in steamy sex. Be mesmerized by their passion and intim…
Watched
39
6:53Stockings5/17/24
Blonde woman in red stockings licks redhead on a mat
Two women are on a green mat in a room with wooden floors. A blonde woman wearing red stockings lies on top of a naked redhead. She uses her tongue to lick t…
Watched
50
6:53Asian5/17/24
Brunette woman in white tank top stands over a naked man
A man sits shirtless in a chair. A brunette woman wearing a white tank top stands in front of him. She reaches down to hold a black mask near his face. They…
Watched
54
6:53Asian5/17/24
Two women having sex on a bed in a padded room
Two naked women are in a padded room. The blonde woman lies on her back on a bed. The other woman stands over her and moves between her legs. They continue t…
Watched
52
6:53Lingerie5/17/24
Two women in black lingerie sit on a bed
Two women sit together on a bed in a bedroom. They are both wearing black lace lingerie. The woman on the left has dark hair and visible tattoos. They look u…
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122
6:53Massage5/17/24
Brunette woman gives a massage to a woman in white
A brunette woman leans over a woman lying on a bed. They are in a room with red roses. The woman on top touches the other woman's body. They stay close toget…
Watched
125
6:53Stockings5/17/24
Brunette woman in white stockings touches herself on a couch
A brunette woman lies on a brown leather couch. She wears white stockings and looks up. She uses her hand to touch her private area. The scene takes place in…
Watched
64
6:53Blonde5/17/24
Blonde woman sits on man's lap in a bedroom
A blonde woman and a man are in a white bedroom. She sits on his lap while lying on a bed. She holds her own breasts as they look at each other. They stay cl…
Watched
93
6:53Asian5/17/24
Man in underwear stands near a woman on a couch
A man and a woman are in a living room. The man stands in dark underwear near a lamp. The woman sits on a black leather couch wearing a red shirt. They look…
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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.