PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    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
    • Black
    • Big Cock
    • 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
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Chastity Pegging Orgasm Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Japanese shemale schoolgirls pegging anal fuck
    07:19
    Japanese shemale schoolgirls pegging anal fuck
    FapHouse
    189K views
    Cuck slave worships Trans Cock featuring Goddess Obsidian
    01:37
    Cuck slave worships Trans Cock featuring Goddess Obsidian
    RealCuckolding
    102.9K views
    Sissy Lucy gets Pegged in Chastity whilst trying to wash up
    02:06
    Sissy Lucy gets Pegged in Chastity whilst trying to wash up
    Spike Essex
    82.3K 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
    119.2K views
    Sissy Latex Maid Lucy gets Pegged In Chastity
    03:18
    Sissy Latex Maid Lucy gets Pegged In Chastity
    Onlyfans
    154K 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
    linktree
    17.7K 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
    2K views
    Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo
    06:39
    Pegged Crossdresser Anal Anal Fucked with a Big Strapon Dildo
    FapHouse
    36K views
    AB093 Photographer feminized squirting-pegging (Chinese and English subtitles)
    02:38
    AB093 Photographer feminized squirting-pegging (Chinese and English subtitles)
    Abby Kitty
    63.8K views
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    11:51
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    Holy
    12.1K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 9
    Bailey Wilde
    9.3K 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
    43.6K views
    Latex sissy in chastity and fucked by Mistress
    05:31
    Latex sissy in chastity and fucked by Mistress
    Abby Kitty
    71.6K views
    Femdom Holy - Degrading Evidence - a Dominatrix story
    20:37
    Femdom Holy - Degrading Evidence - a Dominatrix story
    Holy
    10.2K 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
    8.4K views
    Home Pegging Cumming Sluts
    00:33
    Home Pegging Cumming Sluts
    Lola Spais
    2.5K 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
    26.2K 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
    9.7K views
    Cumming handsfree from pegging
    05:07
    Cumming handsfree from pegging
    Zoeycdgirl
    18.6K views
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    00:50
    Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina
    SissyKanisa
    3.7K views
    Sissy Lucy getting pegged in Chastity with the  dildo
    05:19
    Sissy Lucy getting pegged in Chastity with the dildo
    Onlyfans
    22.8K views
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    06:00
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    Spike Essex
    18.4K views
    Tiny dick ladyboy caged and fucked in webcam
    07:04
    Tiny dick ladyboy caged and fucked in webcam
    SissySimran
    20.9K 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
    76.4K 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
    441.7K views
    How I've made my boyfriend into a anal slut
    04:39
    How I've made my boyfriend into a anal slut
    Trinit Noir
    64.9K 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
    39.9K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    82.7K views
    So Strongly Fucked That I Was Wet Myself
    02:44
    So Strongly Fucked That I Was Wet Myself
    FapHouse
    84.2K views
    Standing Squirt
    02:43
    Standing Squirt
    FapHouse
    79.2K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    116.5K views
    Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits
    01:38
    Milky TGirl in Chastity has Handsfree Sissygasm + Shows her Lactating Tits
    Princesszoey
    94.9K views
    Milk or Tea?
    02:36
    Milk or Tea?
    XiangYan
    19.4K views
    Tranny Girl PUBLIC with a dominant guy! After facial cumshot she continues walking through the city!
    00:43
    Tranny Girl PUBLIC with a dominant guy! After facial cumshot she continues walking through the city!
    TV_Helena
    592.9K views
    TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm
    01:59
    TGirl in Chastity with Lactating Tits has Anal Orgasm Hands Free Sissygasm
    Princesszoey
    78.6K views
    Negative Cage hardcore Cumload
    02:12
    Negative Cage hardcore Cumload
    boobyb0y
    108.6K views
    Trans Girl Forced Orgasm
    08:12
    Trans Girl Forced Orgasm
    Mistress Jodie May
    108.2K views
    Anal Sissygasms In The Woods Chastity Slut Jessica Bloom
    05:17
    Anal Sissygasms In The Woods Chastity Slut Jessica Bloom
    linktree
    34.5K views
    Ride Dildo Challenges 2
    02:46
    Ride Dildo Challenges 2
    FapHouse
    49.6K views
    Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
    07:12
    Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
    Jessica Bloom
    201.2K views
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    06:54
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    Jessica Bloom
    5.5K views
    BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
    06:47
    BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
    Jessica Bloom
    5K views
    Locked, Submissive Trans Sissy in Long Machine Play
    13:58
    Locked, Submissive Trans Sissy in Long Machine Play
    Paula Rainbow
    8.5K views
    16" BBC vs Sissy Slut Jessica Bloom Balls Deep
    07:55
    16" BBC vs Sissy Slut Jessica Bloom Balls Deep
    linktree
    16.4K 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
    4.4K views
    Trap Caged Orgasm
    01:54
    Trap Caged Orgasm
    FapHouse
    33.3K 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
    • 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