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
    -50%
    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
    -60%
    Dating
    Subscriptions
    • Upload
    50% OFF Tokens for NY Ring in 2026 with the right company on xHamsterLive!
    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
    • Bareback
    • Creampie
    • Cumshot
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Chastity Cuckold Pegging Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy gets pegged
    04:31
    Sissy gets pegged
    192.7K views
    Cuck slave worships Trans Cock featuring Goddess Obsidian
    01:37
    Cuck slave worships Trans Cock featuring Goddess Obsidian
    RealCuckolding
    99.2K views
    Mistress Eudora's Anal Slut
    05:28
    Mistress Eudora's Anal Slut
    Loren Aprile
    137.3K views
    Japanese shemale schoolgirls pegging anal fuck
    07:19
    Japanese shemale schoolgirls pegging anal fuck
    SissyKanisa
    184.1K views
    Anal Room Service with Mistress Lilith
    02:34
    Anal Room Service with Mistress Lilith
    Loren Aprile
    417.1K views
    2 sissy latex nurses getting pegged in Chastity by MILF Lisa
    11:47
    2 sissy latex nurses getting pegged in Chastity by MILF Lisa
    Lisa Essex
    116.6K 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
    58.6K views
    Sissy Latex Maid Lucy gets Pegged In Chastity
    03:18
    Sissy Latex Maid Lucy gets Pegged In Chastity
    Spike Essex
    151.7K views
    Hot sexy Mistress pegging trans sissy joyce
    01:18
    Hot sexy Mistress pegging trans sissy joyce
    Sissy Joyce
    694.8K views
    Home Pegging Cumming Sluts
    00:33
    Home Pegging Cumming Sluts
    Lola Spais
    2K views
    Pegging Hardcore with Mistress Revenge
    05:36
    Pegging Hardcore with Mistress Revenge
    Loren Aprile
    14.1K views
    AB093 Photographer feminized squirting-pegging (Chinese and English subtitles)
    02:38
    AB093 Photographer feminized squirting-pegging (Chinese and English subtitles)
    Abby Kitty
    62.5K views
    The only way a sissy is allowed to have sex with a woman
    07:07
    The only way a sissy is allowed to have sex with a woman
    Traviezisha
    15.1K views
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    11:51
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    Holy
    11.4K views
    Fetish Mistress Domina Eva Milf Femdom Fuck Trans Slut Ekaterina Krieg Latex BDSM Kink Strapon Shemale Sissy Hardcore
    16:50
    Fetish Mistress Domina Eva Milf Femdom Fuck Trans Slut Ekaterina Krieg Latex BDSM Kink Strapon Shemale Sissy Hardcore
    Dominatrix Eva
    628.5K views
    Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF
    12:45
    Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF
    Spike Essex
    42.9K views
    Down the Sissy Rabbit Hole - My Story
    00:44
    Down the Sissy Rabbit Hole - My Story
    Sissy Joyce
    9.1K views
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    01:26
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    FrinaXXX
    842 views
    Sissy hubby with wife.
    19:05
    Sissy hubby with wife.
    130.4K views
    Latex sissy in chastity and fucked by Mistress
    05:31
    Latex sissy in chastity and fucked by Mistress
    Abby Kitty
    70.7K views

    Relevant Short videos

    Memorable moment from "Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF"
    Memorable moment from "Chastity sub gets double anal penetration from big cock TGirl and strap-on MILF"
    Spike Essex
    1.2K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Bailey Wilde
    1K views
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    My Sissy Cums Again From the Huge BBC Oh, This Feels Amazing! I Hope You Can Do This Yourself?
    FrinaXXX
    46 views
    Locked Latex Chastity Sissygasm
    Locked Latex Chastity Sissygasm
    Sissy Sidney
    16.9K views
    straped on caged cum
    straped on caged cum
    boobyb0y
    9K views
    Sissy orgasm in a chastity cage
    Sissy orgasm in a chastity cage
    Laura Lou
    3.6K views
    The Vice Mach 2 chastity cage (prototype) product review!!
    09:16
    The Vice Mach 2 chastity cage (prototype) product review!!
    Sissy Joyce
    30.5K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Bailey Wilde
    8.7K views
    Chasity cage
    03:55
    Chasity cage
    NikkyTrav
    147.8K views
    Femdom Holy - Degrading Evidence - a Dominatrix story
    20:37
    Femdom Holy - Degrading Evidence - a Dominatrix story
    Holy
    10K views
    Cutie Girl pegging tranny
    03:05
    Cutie Girl pegging tranny
    179.5K views
    Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut
    03:12
    Sub Cums Between valentinarosa89 and I - Mistress and Shemale Double Top a Sub Slut
    Jasmine_dlight
    7.9K views
    Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo
    06:39
    Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo
    SissyKanisa
    34.9K views
    Sissy Charlotte locked in E-Stim chastity cage and getting pegged by MILF Lisa
    09:07
    Sissy Charlotte locked in E-Stim chastity cage and getting pegged by MILF Lisa
    Lisa Essex
    25.6K views
    Femdom Pegging Sissy
    05:43
    Femdom Pegging Sissy
    Sasha Earth
    96.1K views
    Cumming handsfree from pegging
    05:07
    Cumming handsfree from pegging
    Zoeycdgirl
    18.2K views
    Cuckold chastity  shemale
    06:15
    Cuckold chastity shemale
    117.3K views
    Strap-on Fuckers: Sissy Slut in Chastity Used by Her Domina
    02:45
    Strap-on Fuckers: Sissy Slut in Chastity Used by Her Domina
    littlemissbrat
    9.4K views
    How to Put on Flat Chastity Cage Guide (Jessica Bloom)
    06:08
    How to Put on Flat Chastity Cage Guide (Jessica Bloom)
    Jessica Bloom
    29.4K views
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    00:50
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    SissyKanisa
    3.2K views
    Mistress Revenge Destroying my Ass in her hotel room
    01:51
    Mistress Revenge Destroying my Ass in her hotel room
    Loren Aprile
    228K views
    Sissy Lucy getting pegged in Chastity with the  dildo
    05:19
    Sissy Lucy getting pegged in Chastity with the dildo
    Spike Essex
    22.5K views
    Sissy Joyce humiliated and pegged by a goddess
    01:09
    Sissy Joyce humiliated and pegged by a goddess
    Sissy Joyce
    133.3K views
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    06:00
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    Spike Essex
    18.1K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    675.8K views
    Tiny dick ladyboy caged and fucked in webcam
    07:04
    Tiny dick ladyboy caged and fucked in webcam
    SissySimran
    20.5K views
    Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging
    07:28
    Sissy Slut Strap on Fucked By Femdom Mistress - Jessica Bloom & Polieana Pegging
    Jessica Bloom
    16.5K views
    PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
    04:42
    PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
    PorchaeTS
    86.6K views
    Week-end confinement
    14:45
    Week-end confinement
    NikkyTrav
    259.1K views
    Permanent Chastity - Locking Using a Permalocker
    01:12
    Permanent Chastity - Locking Using a Permalocker
    FunkyLasers
    107K views
    Sissy in chastity fucked by different people
    01:41
    Sissy in chastity fucked by different people
    Sissy Joyce
    524.1K views
    TGirl Puts on Chastity Cage, Locking Away her Tiny Penis
    01:11
    TGirl Puts on Chastity Cage, Locking Away her Tiny Penis
    Princesszoey
    55.6K views
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    05:11
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    Jessica Bloom
    271.2K 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