Skip to content
ladyboyshemale

Longest Ladyboy Sex Video - Page 4

2,964 videos
Sultry Ladyboy Marcella's Anal Fucking Debut10:00
Anal5/17/24

Sultry Ladyboy Marcella's Anal Fucking Debut

Welcome to a world of forbidden pleasure where gender norms are broken, and desires take flight. Step into this taboo world where a stunning shemale named Ma…

Watched
Sweet Ladyboy's Green Cucumber Playtime10:00
Asian5/17/24

Sweet Ladyboy's Green Cucumber Playtime

Satisfy your desires with our hot shemale videos featuring the most beautiful and alluring ladies. Watch as they pleasure themselves with green cucumbers, ta…

Watched
Ladyboy's Hot Blowjob ~ Dripping with Cum10:00
Blowjob5/17/24

Ladyboy's Hot Blowjob ~ Dripping with Cum

Our sex video features a gorgeous shemale with a stiff dick in her mouth, ready to pleasure any man who dares to come close. Her feminine curves and alluring…

Watched
Ladyboy Domination ~ Fake Tits and Doggy Style10:00
Femdom5/17/24

Ladyboy Domination ~ Fake Tits and Doggy Style

Brace yourself for an explosive sex video featuring a shemale with striking fake tits. The siren's sultry gaze will captivate you as she enthusiastically eng…

Watched
Ladyboy's Hot Blowjob ~ Stunning Sex Video10:00
Blowjob5/17/24

Ladyboy's Hot Blowjob ~ Stunning Sex Video

Find full-length sex videos featuring gorgeous shemales and their lovers in intimate moments. Watch as these stunning shemales tease, please and get pleasure…

Watched
Milena's Ladyboy Hotspot ~ A 3some to Remember10:00
Threesome5/17/24

Milena's Ladyboy Hotspot ~ A 3some to Remember

Experience the ultimate in erotic pleasure with stunning shemale Milena Marianna as she takes center stage in a scorching hot 3some. Watch as she seductively…

Watched
Ladyboy Facesitting ~ A Hitman's Wet Dream10:00
Asian5/17/24

Ladyboy Facesitting ~ A Hitman's Wet Dream

Shemale Dominatrix Punishes Unsuspecting Hitman with Insatiable Blowjob - In this steamy sex video, a shemale dominatrix takes control of a hapless hitman an…

Watched
Ladyboy Goddess Dominates with Anal Toy10:00
Femdom5/17/24

Ladyboy Goddess Dominates with Anal Toy

Shemale is a term sometimes used to describe a transgender individual with male genitalia. In this sex video, a shemale is engaging in anal sex, showcasing h…

WatchedAnal
Ladyboy gets pounded by hung nigger10:00
Big Cock5/17/24

Ladyboy gets pounded by hung nigger

Shemale is a term used to describe a transgender individual who has male genitalia, but identifies as female. In this sex video, the shemale is being pleasur…

Watched
Ladyboy Teighjianna's Hot Fucking Adventures10:00
Hardcore5/17/24

Ladyboy Teighjianna's Hot Fucking Adventures

Teighjianna, the sexy tattooed chick who loves shemales, is fucking in this hot sex video. She's ready to take on any challenge and offers an unforgettable e…

Watched
Ladyboy's Hard Dick Gets Sucked to the Bone10:00
Blowjob5/17/24

Ladyboy's Hard Dick Gets Sucked to the Bone

Shemale is a term used to describe a female-to-male transgender individual. In this video, a hot shemale is seen getting her dick sucked by an eager partner…

Watched
Ladyboy's Amorous escapade with a Lucky Lover10:00
Asian5/17/24

Ladyboy's Amorous escapade with a Lucky Lover

Shemales are known for their wild and uninhibited sexual appetites, and this video is no exception. Watch as a beautiful shemale takes on a lucky man in a ra…

Watched
Anal sex with Ladyboy bombshell Vittoria T10:00
Anal5/17/24

Anal sex with Ladyboy bombshell Vittoria T

Vittoria T, the famous fake-tit shemale, is back and better than ever in this steamy anal adventure. Don't miss the chance to witness Vittoria's incredible t…

Watched
Ladyboy Dominates Old Cock in Missionary Pose10:00
Femdom5/17/24

Ladyboy Dominates Old Cock in Missionary Pose

♀️ Shemale TS Pornstar Hardcore Fucks Older Man in Missionary Pose ~ Cum Explosion! ☝️ Forget everything you've seen before - this shemale pornstar is taking…

Watched
Redheaded Ladyboy's Wild Orgy with Her Friend10:00
Asian5/17/24

Redheaded Ladyboy's Wild Orgy with Her Friend

This sex video features a stunning redhead shemale and her friend engaging in passionate and steamy lovemaking. Watch as they explore each other's bodies, ta…

Watched
Ladyboy Blowjob Overload ~ Fake-Tits Take Over10:00
Blowjob5/17/24

Ladyboy Blowjob Overload ~ Fake-Tits Take Over

Relish in the pleasure of the beautiful shemale as she receives an unforgettable blowjob, her flawless body accentuated by her silicone breasts. Experience t…

Watched
Ladyboy Fucks with Fake Tits and Anal Pleasure10:00
Busty5/17/24

Ladyboy Fucks with Fake Tits and Anal Pleasure

Shemale is a term used to describe a transgender woman with male genitalia. In this video, the shemale is shown engaging in anal sex, highlighting her unique…

WatchedAnal
Ladyboy Anna Hickhiman's Anal Banging Pleasure10:00
Anal5/17/24

Ladyboy Anna Hickhiman's Anal Banging Pleasure

Anna Hickhiman, the tanned shemale, shines in this explicit anal scene. With her stunning looks and impeccable skills, she's a true delight to watch. Gorgeou…

Watched
Ladyboy's Sweet Blowjob for a Big Black Cock10:00
Blowjob5/17/24

Ladyboy's Sweet Blowjob for a Big Black Cock

Discover the intense pleasures of a shemale encounter. Our captivating blonde babe is a true master at providing mind-blowing blowjobs. Watch as she takes on…

Watched
Ladyboy Porn ~ Nasty Bangin' with Sexy Babe10:00
Asian5/17/24

Ladyboy Porn ~ Nasty Bangin' with Sexy Babe

Shemale is a term used to describe a transsexual woman who has undergone sexual reassignment surgery. In this sex video, you will witness some of the sexiest…

Watched

From our partners

Ad
Ad
Ad
Ad
Ad
Ad

Related labels

All labels

Popular Searches

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.