9:54Anal5/17/24
Ladyboy Pops Cherry with Cock ~ Anal Virgin No More!
Shemale is a term often used to describe transgender women with male biology. In this hott sex video, a shemale takes it up the ass for the first time with a…
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35Longest Ladyboy Sex Video - Page 8
2,964 videos9:54
9:54Anal5/17/24
Ladyboy Cocksucker's Ass Play ~ Too Good to Resist!
Discover the ultimate shemale experience with our exclusive video collection of shemales taking it to the next level. Watch as they suck cock, finger their o…
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40
9:54Hardcore5/17/24
Ladyboy's Soft Boobs Get Fucked Hard
Shemale Sex Video - Perkier Boobs & Harder Cock Fucking!
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40
9:54Blowjob5/17/24
Ladyboy Babe Gives Hot Blowjob ~ Blonde Seduces with Fiery Passion
This steamy video features a blonde shemale teasing her lucky partner with a sensual blowjob. Get ready for an intense experience as you watch this hot shema…
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42
9:54Blowjob5/17/24
Ladyboy Oral Fantasy ~ Enjoy Every Inch of Your Favorite Trans Sex Star!
When it comes to oral pleasure, nothing beats the skills of a shemale. With years of experience in pleasing her partners, she knows just how to tease and sat…
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46
9:51Cam5/17/24
Ladyboy Hosts Live Cam Show ~ Jizz Splashing on the Sheets!
Shemale video - Get ready to witness a steamy sex show featuring a gorgeous brunette shemale who knows how to tease and please. Watch as she confidently play…
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43
9:50Anal5/17/24
Ladyboy Anal Orgasm ~ Strong and Sensual Pleasure
Strong anal for shemale in need for orgasm - This sex video features a shemale in need of an intense orgasm. Watch as she receives strong anal pleasure that…
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26
9:50Femdom5/17/24
Ladyboy Dominates Carla and Maaa ~ A XXX Fantasy for Your Pleasure
Shemale pleasures with Carla and Mia Monroe in this scorching-hot sex video. Watch as these feminine lasses tease and pleasure each other in a passionate dis…
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28
9:50Anal5/17/24
Ladyboy Whore Diva ~ The Ultimate Pleasure Dirty Anal Fun
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31
9:50Anal5/17/24
Ladyboy's Anal Pleasure ~ Hot Lovin' in the Backdoor
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29
9:50Hardcore5/17/24
Sexy Ladyboy Gets Her Face Fucked by a Huge Cock!
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30
9:50Blowjob5/17/24
Ladyboy Rough Scene Along Morena Cock Sucking
Morena is the ultimate shemale experience. With rough sex scenes and hardcore cock sucking, this video will leave you breathless. Starring the hottest shemal…
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28
9:50Anal5/17/24
Voluptuous Ladyboy's Anal Obsession
Voluptuous shemale simply loves anal is a captivating sex video featuring a shemale with an insatiable appetite for anal pleasure. Experience the thrills and…
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27
9:50Asian5/17/24
Ladyboy Morocha Reveals Her Love for Fat Dick
French inseam? Moi? Non, non, nen nen! - Monroe Steele
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35
9:50Busty5/17/24
Busty Ladyboy Ass Fuck ~ 101-degree, A-Frame, Koerner's Dome
Enjoy the steamy scene of a busty shemale getting pounded in the ass. Experience the unique pleasure of a sexy transgender star as they take control in the b…
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34
9:50Asian5/17/24
Curvy Ladyboy's Fat Dick Adventure
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30
9:50Blowjob5/17/24
Ladyboy in Stockings Dominates with Amazing Blowjob
Shemale in stockings delivers stunning blowjob - Best shemale video you'll ever watch! Discover our selection of high-quality shemale videos, featuring the m…
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30
9:50Asian5/17/24
Kiara & Tania's Ladyboy Play Time Revealed!
Title ~ Shemale sex video, featuring Kiara and Tania ~ Description ~ Get ready for an intense and steamy shemale sex video, starring the gorgeous Kiara and b…
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33
9:50Anal5/17/24
Brunette Ladyboy's Anal Pleasure Delight
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31
9:50Anal5/17/24
Ladyboy Star Mariana's Steamy Anal Romp!
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37
9:50Anal5/17/24
Anal with Sexy Ladyboy Brenda ~ A Taboo Desire Fulfilled
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35
9:50Hardcore5/17/24
Morena's Full Hardcore Fuck ~ Ladyboy Porn at Its Best
Morena, a stunning shemale, showcases her irresistible curves in this full hardcore fuck video. Feast your eyes on her perfect body as she takes on two guys…
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35
9:50Anal5/17/24
Ladyboy Anal Madness with Milena ~ The Ultimate Passion
Your sex video features a sensual brunette shemale who takes on a dominant role in the bedroom. Watch her get fucked hard in the ass by a willing partner as…
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46
9:50Anal5/17/24
Morena's Ladyboy Sexual Fusion ~ Mind-Blowing Anal Pleasure
Morena enjoys sensual anal stimulation to the fullest, in this sizzling hot shemale video. Her smooth curves and seductive eyes will leave you craving for mo…
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41
9:50Asian5/17/24
Raw Rim Jobs with a Ravishing Ladyboy
Rough anal with a horny shemale - For those who have a craving for rough anal sex, this shemale is the perfect choice. With her immense stamina and insatiabl…
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33
9:50Anal5/17/24
Ladyboy Goddess Enters Taboo World of Anal with Straight Guy
Ciara Stone takes on two hunky males in the steamy shemale sex video. The scene is hot and intense, with Ciara's curvaceous body on full display as she takes…
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45
9:49Blonde5/17/24
Ladyboy Sexual Kinks with Sexy Blonde
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43
9:20Solo5/17/24
Ladyboy Solo Porn ~ Nasty Posing at its Best!
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27
9:20Hardcore5/17/24
Ladyboy Andrea De Oliviera's Steamy Fuck with a Lucky Man
Watch the wildest sex video of the year with Andrea De Oliviera, the most stunning Brazilian shemale. She fucks like never before with her partner, a lucky m…
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29
9:20Femdom5/17/24
Ladyboy Dominates Fake-tit Blonde with Hard Dick
Shemale porn star, the stunning Fake-tit blonde, is getting it on with huge hard dick. Explore the world of shemale porn and discover the thrill of watching…
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27
9:20Masturbation5/17/24
Tanned Ladyboy's Wild Wanking Session ~ So Sexy You Can't Resist!
Shemales are incredibly sexy and we have a tanned beauty with us here. Watch as she wanks so sensually that you can't take your eyes off her. The way her mus…
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34
9:20Busty5/17/24
Ladyboy's Hot SoloPlay with Massive Tits & Heat Waves!
Shemale sex video ~ Hot bimbo with huge tits in heats!
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27
9:20Asian5/17/24
Ladyboy Goddess Reveals Her Irresistible Dick
Sensual shemale reveals her impressive manhood in steamy sex video.
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37
9:12Blonde5/17/24
Ladyboy's Explosive Masturbation ~ Blonde TS Goes Wild in Intimate Solo Session
Shemale Porn ~ Watch as a blonde tranny jerks off hard as fuck in a very loud home solo. Experience the ultimate transexual pleasure and let your fantasies c…
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44
9:10Masturbation5/17/24
Kalena Rios masturbates alone in her living room
Kalena Rios sits in a room decorated with various paintings. She wears a tan dress and starts touching herself. She continues masturbating while looking at t…
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119
9:10Busty5/17/24
Ladyboy's Fake Tits Tease Hard Dick - EXCLUSIVE VIDEO!
Relish in the sight of a stunning shemale with fake breasts who knows how to pleasure a male member like no other. Watch as she teases and plays with her par…
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27
9:10Busty5/17/24
Ladyboy Goddess Flaunts Fake Tits and Curvy Body
Getting intimate with a shemale can be a mind-blowing experience, and this video of a fake-tit shemale is no exception. Watch as she flaunts her curves and s…
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24
9:10Solo5/17/24
Dirty Ladyboy Solo ~ Unleashing the Inner Beast
Absolut, immer wieder vanilleaehnlich. Flucht, der Speicherinhalt, aber ich denke, dass ist nicht so passioniert an Seinem Leben.
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43
9:10Lingerie5/17/24
Ladyboy Goddess in Lingerie ~ Assy Pleasure
Assy shemale performs in her alluring lingerie in an intimate and seductive video. Discover the ultimate pleasure with this feminine beauty. Don't miss out o…
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31
9:10Solo5/17/24
Trap Queen of the She-Male World ~ Nasty Solo by Kawana
Relish in the lascivious display of shemale Kawana as she engages in a lustful solo performance. Watch as this seductive temptress teases and pleasures herse…
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30
9:10Solo5/17/24
Black Ladyboy's Solo Pleasure ~ A Sexy tease for you!
Enjoy an exhilarating solo scene featuring a stunning black shemale with sexy fake tits. Experience the ultimate pleasure of watching this gorgeous lady touc…
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26
9:10Asian5/17/24
Ladyboy P Jordana ~ Dirty Pleasure Ritual Exposed!
Get ready for a steamy solo session with sexy Patricia as she explores her body in a most naughty way. Don’t miss the excitement as this shemale teases and p…
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29
9:10Hardcore5/17/24
Horny Ladyboy Fucks with Fake Boobs on Camera!
Watch the shemale model with fake tits masturbating her dick on camera. Experience the ultimate transgender porn sensation that will leave you craving for more.
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26
9:10Solo5/17/24
Seductive Ladyboy Solo ~ Leggy Goddess Takes Control
Satisfy your cravings for shemale pleasure with this solo scene featuring a sexy leggy temptress. Watch as she teases and pleasures herself in ways that will…
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32
9:10Blonde5/17/24
Ladyboy Amateur ~ Blonde Wanking Her Nice Dick
Experience the ultimate pleasure with our blonde shemale, as she wanks her nice dick for your viewing pleasure. Our hot shemale will leave you breathless and…
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29
9:10Blonde5/17/24
Ladyboy's Hard Dick Brings Sexy Blonde to Climax
Enjoy watching this sexy shemale pleasure herself with her impressive dick. She's a blonde bombshell with a cock that will leave you drooling. Don't miss out…
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30
9:10Solo5/17/24
Ladyboy's Steaming Solo Session ~ Satisfying Her Desires
Have you ever watched a shemale that will take your breath away? You won't believe the incredible solo scene of this brunette who will leave you speechless…
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33
9:10Asian5/17/24
Racy Ladyboy Encounter in Erotic Bedroom Adventure
Get ready for a steamy night in the bedroom with our filthy shemale! Experience the ultimate pleasure as she takes you on a wild ride filled with passion and…
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38
9:10Masturbation5/17/24
Brunette shemale masturbates on a sofa
A brunette shemale sits on a beige sofa. She has fake tits and wears a necklace. She uses her hand to touch herself while sitting. The scene shows her solo m…
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63
9:10Masturbation5/17/24
Penelope Jolie masturbates while showing her tattoos
Penelope Jolie is alone in a room. She shows off her large tattoos and leopard print bikini. She starts masturbating her body. The video ends with her contin…
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62
9:01Femdom5/17/24
Ladyboy Dominatrix Pummels Tight Hole with Huge Strap-On
Busty MILF shares her shaved holes with eager partner in steamy sex video. Watch as she takes on a massive cock in both her shaved holes, leaving her satisfi…
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39
9:01Blowjob5/17/24
Man gives blowjob to woman in red skirt on couch
A man sits on a leather couch in a living room. He performs a blowjob on a woman wearing a red skirt and black panties. Another woman in a purple shirt stand…
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89
9:00Asian5/17/24
Patricia Bysmark pulls up her panties in a bedroom
Patricia Bysmark stands alone in a bedroom. She is naked from the waist up. She slowly pulls up her patterned panties. The woman looks down at her body while…
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65
9:00Blowjob5/17/24
Ladyboy Bate Takes Bathtub Blowjob in Taboo Romp
Satisfy your desires with the ultimate experience of a shemale blowjob in a steamy bathtub. Get ready to indulge in a sensual adventure that will leave you b…
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22
9:00Solo5/17/24
Ladyboy's Sensual Solo ~ Romantic Cock Tease
Discover the ultimate pleasure of shemale sex with our exclusive lady boy video. Witness the irresistible beauty of our shemale as she seductively strokes he…
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29
9:00Asian5/17/24
Unleash the Ladyboy Queen ~ A Lesbian Fantasy Come True
Watch a sensual shemale pleasuring herself with a sex toy, while a curious lesbian friend can't resist joining in on the fun. Experience the erotic pleasure…
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25
9:00Femdom5/17/24
Ladyboy Domination ~ Tranny Bends Over and Fucks
Watch the ultimate shemale experience with a hot tranny bending over and taking it deep. The perfect intercourse between two horny adults will leave you brea…
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26
9:00Outdoor5/17/24
Asian woman and man having sex outdoors
A woman with glasses and a red top is outside with a man. They start by getting close to each other. The man is shirtless during the encounter. They continue…
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77
9:00Latina5/17/24
Sultry Latina Ladyboy Delights with Cock in Solo Pleasure
Latin shemale delivers ultimate pleasure in solo play with her own cock. Experience the eroticism of a male-to-female transgender performer in this must-see…
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33
9:00Asian5/17/24
Ladyboy Cutie Gets Pampered with Rough Love
Shemale is a term often used to describe a trans woman with a penis. In this sex video, a shemale cutie is being fucked from behind by her partner, showcasin…
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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.