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

    Riding Chastity Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    11:37
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    950K views
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    09:05
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    Adam Castle
    372.9K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    New Chastity BJ COWGIRL FUCK
    15:26
    New Chastity BJ COWGIRL FUCK
    754.7K views
    Sexy BIG ASS TRANS GIRL Giving A HUGE TORSO
    08:12
    Sexy BIG ASS TRANS GIRL Giving A HUGE TORSO
    MarilyDaniela
    257K 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
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Sissy Merve Rose Chastity Bdsm Fucked DoggyStyle New Body Stockings Sexy Blonde Femboy Tgirl trans Tranny Anal Cum BBC Big Black
    05:10
    Sissy Merve Rose Chastity Bdsm Fucked DoggyStyle New Body Stockings Sexy Blonde Femboy Tgirl trans Tranny Anal Cum BBC Big Black
    TSMerve
    29K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    78.2K views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    19.3K views
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    10:16
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    Jessica Bloom
    71.8K views
    Granny tranny Holly riding a BBC dildo and cums in her chastity cage
    03:22
    Granny tranny Holly riding a BBC dildo and cums in her chastity cage
    Hollycd1
    86.8K views
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    05:27
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    ActorFab
    234.1K views
    Trans Chastity Beauties Tease With Toys
    11:09
    Trans Chastity Beauties Tease With Toys
    hothotfilms
    42.4K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.9M views
    Chastity cage and fuck machine makes perfect cum
    14:09
    Chastity cage and fuck machine makes perfect cum
    yourprettykate
    17.4K views
    Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
    01:13
    Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
    Layne Love
    178K views
    Everything a sissy needs .... give it to her
    09:46
    Everything a sissy needs .... give it to her
    kinkydanielle
    14.3K views
    Cute tranny fucked in tiny chastity bareback
    02:11
    Cute tranny fucked in tiny chastity bareback
    Trinit Noir
    41.6K views
    JOKER'S XXX FUN: Messy Makeup Fuck With Tgirl Harley ABRIDGED
    12:16
    JOKER'S XXX FUN: Messy Makeup Fuck With Tgirl Harley ABRIDGED
    Adam Castle
    8.4K views
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    02:55
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    XiangYan
    311.1K views
    My Butthole LooksSo Good Being Stretched Out in the Sunlight
    05:21
    My Butthole LooksSo Good Being Stretched Out in the Sunlight
    MJ
    32K views
    Fuck Machine Sissygasm
    01:30
    Fuck Machine Sissygasm
    boobyb0y
    202.9K views
    SISSYBOI FEMBOI WITH CHASTITY CAGE  RIDING INTERRACIAL BBC HARD
    01:35
    SISSYBOI FEMBOI WITH CHASTITY CAGE RIDING INTERRACIAL BBC HARD
    Alesissyboi
    179.5K views
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    03:09
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    Starlightfemboy
    436K views
    2 slutty sissies making out while riding a BBC
    00:57
    2 slutty sissies making out while riding a BBC
    Ericka Sprinkle
    107.2K views
    Lena Vesper's Milking & Gooning Session
    08:12
    Lena Vesper's Milking & Gooning Session
    Snake_0rgy
    187.8K views
    Ride Dildo Challenges 2
    02:46
    Ride Dildo Challenges 2
    XiangYan
    47.9K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    122.2K views
    Sissy locked in chastity and fucks her self hard trying to cum.
    06:27
    Sissy locked in chastity and fucks her self hard trying to cum.
    Lexa Styles
    10.5K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    267.3K views
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    11:21
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    Sissy Candy
    51.8K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    115K views
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    06:54
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    Jessica Bloom
    5.5K views
    Daddy loves to wreck my asshole in chastity
    06:24
    Daddy loves to wreck my asshole in chastity
    missangell_
    477.3K views
    Sissy riding dildo outside
    10:45
    Sissy riding dildo outside
    SissyDaniella
    25.9K views
    Sissy Sex Slave
    07:00
    Sissy Sex Slave
    Kapri Sun
    50.5K views
    Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
    07:25
    Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
    Jessica Bloom
    3.4K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    220.2K views
    Sissy Merve Rose School girl chastity belt doggy style big black cock  hardcore bdsm blonde sexy tgirl tranny trans femboy baby
    05:06
    Sissy Merve Rose School girl chastity belt doggy style big black cock hardcore bdsm blonde sexy tgirl tranny trans femboy baby
    TSMerve
    9K views
    Sex Chair
    03:06
    Sex Chair
    XiangYan
    63.1K views
    Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom
    10:20
    Ass to Mouth With Over 100 Loads of CUM! Frozen Cum Play Sissy Jessica Bloom
    Jessica Bloom
    17K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Sissy locks her tiny Clitty in inverted Chastity Cage and rides her big Qutoys Dildo
    09:19
    Sissy locks her tiny Clitty in inverted Chastity Cage and rides her big Qutoys Dildo
    Sissy Slut Chantal Sweet
    6.3K views
    Bound sissy in chastity gets BBC
    07:46
    Bound sissy in chastity gets BBC
    946K views
    Chastity cage and fuck machine are best present
    07:50
    Chastity cage and fuck machine are best present
    yourprettykate
    4.5K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    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