PornPorn Transgender • US
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Crossdressing Roulette Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdressing
    Crossdressing Homemade
    Caught Crossdressing
    Crossdressing Sluts
    Crossdressing Husband
    Vintage Crossdressing
    Crossdressing Daddies
    Crossdressing Faggots
    Grandpa Crossdressing
    Christmas Crossdressing
    Crossdressing Couple
    Crossdressing Pvc
    Crossdressing Amateurs
    Cock Roulette
    Crossdressing Tranisa
    Crossdressing Men
    Crossdressing Fantasy
    Kigurumi Crossdressing
    Crossdressing Doctor
    Crossdressing Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy secretary fucked hard bent over the table
    06:50
    Sissy secretary fucked hard bent over the table
    Ashley Roze
    932.9K views
    The stepsisters always deliver
    08:12
    The stepsisters always deliver
    Pure Ts
    171.4K views
    shemale cum sissy slut cums Trans cumming
    16:14
    shemale cum sissy slut cums Trans cumming
    SissyGirlTs
    35.6K views
    extreme masturbation
    11:11
    extreme masturbation
    TSquennAna
    148.8K views
    Cumshots 2024 Part II
    05:19
    Cumshots 2024 Part II
    Strapsex
    346.6K views
    Thick Cock with New Morning Coat
    06:40
    Thick Cock with New Morning Coat
    Sonitchka
    34.9K views
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    44:10
    Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
    alinanightsky
    233.7K views
    Sissy crossdress anal slut gets thick uncut dick bare in her little ass
    53:14
    Sissy crossdress anal slut gets thick uncut dick bare in her little ass
    Tgirl Riley
    151.9K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    28.1K views
    Stroking my throbbing dick for you
    01:27
    Stroking my throbbing dick for you
    barbiebelladollz
    67.6K views
    Chubby crossdresser getting fucked by BBC bareback
    01:30
    Chubby crossdresser getting fucked by BBC bareback
    470.9K views
    Crossdresser Sexy Dances  Salsa
    04:47
    Crossdresser Sexy Dances Salsa
    Ashe Vex
    18.8K views
    Petite bitch begs for this huge cock deep inside her dirty asshole
    05:12
    Petite bitch begs for this huge cock deep inside her dirty asshole
    MrNastyXavier
    246K views
    Crossdresser Sucking Nice Cock 7
    18:09
    Crossdresser Sucking Nice Cock 7
    475.8K views
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    05:56
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    Elvi Lynx
    63.6K views
    I love to ride your dick hard like a good bitch
    05:19
    I love to ride your dick hard like a good bitch
    missangell_
    234.6K views
    Tranny dominates you at work
    07:05
    Tranny dominates you at work
    Kymmy Harper
    706.3K views
    Sweet 18yo Trans Girl Anal Mastrubation
    06:34
    Sweet 18yo Trans Girl Anal Mastrubation
    Fembaby
    43.7K views
    Mature Sissy Gets Her Slutty Ass Fucked Hard
    18:54
    Mature Sissy Gets Her Slutty Ass Fucked Hard
    Trans and Co
    56.3K views
    BF demolishes my young femboy bussy (2025 Remaster)
    12:36
    BF demolishes my young femboy bussy (2025 Remaster)
    Prettyboi2000x
    68.8K views
    Crossdress Trans Sissy Sloppy BlowJob JOI
    10:15
    Crossdress Trans Sissy Sloppy BlowJob JOI
    IskraElectrical49
    52K views
    Asian Sissy Chastity Anal Cumshot
    07:41
    Asian Sissy Chastity Anal Cumshot
    CuteAsianSissy
    70.8K views
    Cute tranny girl used in public! Grabbing! Spanking! Slapping! Mouthfuck! Facial!
    01:17
    Cute tranny girl used in public! Grabbing! Spanking! Slapping! Mouthfuck! Facial!
    Allmylinks
    44.3K views
    Petite bitch loves to fuck in pantyhose with her roommate
    06:23
    Petite bitch loves to fuck in pantyhose with her roommate
    MrNastyXavier
    197.3K views
    Trans Girl Masturbating and Cums All Over Her Self
    03:44
    Trans Girl Masturbating and Cums All Over Her Self
    Bellaroar
    153.3K views
    filling the ass of the horny Trans Neighbor
    10:40
    filling the ass of the horny Trans Neighbor
    Smoker Master
    91.5K views
    Hot Ebony TS Gets Stroked and Deepthroated During Sleepover
    06:10
    Hot Ebony TS Gets Stroked and Deepthroated During Sleepover
    EROS ORISHA
    134.5K views
    Mature Trans Gets Fucked by a Black Guy
    36:38
    Mature Trans Gets Fucked by a Black Guy
    Trans and Co
    359.6K views
    Sexy Crossdresser Sucks and Fucks
    03:21
    Sexy Crossdresser Sucks and Fucks
    788.3K views
    Creamy cumshot on cute toes. Femboy Kiko Candy fucks feet and cums on them in stirrups
    05:23
    Creamy cumshot on cute toes. Femboy Kiko Candy fucks feet and cums on them in stirrups
    Kiko Candy
    124.7K views
    Step brother get final outdoor blowjob
    05:11
    Step brother get final outdoor blowjob
    Rozebell
    624.2K views
    Sucking My Own Cock Til I Cum
    05:50
    Sucking My Own Cock Til I Cum
    Emily Meadows
    142.7K views
    Rigid3d D3d Destroying a Beautiful Tasty Slut Swallowing a Huge Monster Cock Sweet Huge Tight Ass
    07:06
    Rigid3d D3d Destroying a Beautiful Tasty Slut Swallowing a Huge Monster Cock Sweet Huge Tight Ass
    taptapKO
    206.8K views
    Mia was betrayed by her friend and husband. Eliel loves Mia but doesn't miss an opportunity to be sucked by a
    07:12
    Mia was betrayed by her friend and husband. Eliel loves Mia but doesn't miss an opportunity to be sucked by a
    Mirella Diniz
    866K views
    This Sissy Tgirl Will Get Her Ass Strap-on and Fuck
    02:53
    This Sissy Tgirl Will Get Her Ass Strap-on and Fuck
    Emmy Angeles
    26.9K views
    Giulia Furacao Fucks Good with Leo Fortunatto
    07:10
    Giulia Furacao Fucks Good with Leo Fortunatto
    Mirella Diniz
    323.7K views
    I fuck my stepsister's busty for her big pussy
    07:14
    I fuck my stepsister's busty for her big pussy
    Yeison
    2.3M views
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    07:20
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    Sonechka25
    36.1K views
    First meeting crossdressing mature sissy
    11:07
    First meeting crossdressing mature sissy
    379.9K views
    shemale loves to be pushed into her uterus
    10:10
    shemale loves to be pushed into her uterus
    Branquinha Large
    292.6K views
    Hot Trans Girl Cums inside her own Anal Self Fuck Creampie - Kinkysky18
    07:10
    Hot Trans Girl Cums inside her own Anal Self Fuck Creampie - Kinkysky18
    KinkySky
    247.6K views
    Sissy Chastity Maid Service Training With Ria Bentley
    07:07
    Sissy Chastity Maid Service Training With Ria Bentley
    Ria_Bentley
    40.6K views
    Delicious pink pussy from my young redhead friend
    06:21
    Delicious pink pussy from my young redhead friend
    Nathalia Fontes
    1.8M views
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    21:12
    Ria Bentley Gets Impregnated by Her 10" Bull Date
    Ria_Bentley
    207.4K views
    POV you're fucking a hot white bitch
    05:22
    POV you're fucking a hot white bitch
    MrNastyXavier
    101.9K views
    Cute tranny in chastity playing with big dildos and anal fisting and fisting
    04:20
    Cute tranny in chastity playing with big dildos and anal fisting and fisting
    Trinit Noir
    22.3K views
    Legs Spread Getting Pounded Into Headboard
    02:58
    Legs Spread Getting Pounded Into Headboard
    Bottom Jen
    226.9K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 80
    • Next

    Searches Related to Crossdressing Roulette

    • Burlesque
    • Blackadder Dickgirls 11
    • Nipple BDSM
    • Big Cocks Big Cums Compilations
    • Aranxasmith Amazing Cumpilation
    • Gender Bender
    • Femboy Rimming
    • Pink Panties
    • Unexpected Cock Surprise Trannybizarre
    • Wife Pegging
    • Tall Leggy Tgirl Cumshot
    • Undressing
    • Accidental Ejaculation During Massage
    • Futa Breeding Futa Female
    • Lesbian Piss Drinking
    • Precum Eating Compilation
    • Double Chastity
    • I Know Your Secret
    • Fake Vagina Pants
    • Sissygasm Trainer

    xHamster

    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025

    Help

    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster

    Legal

    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults