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
    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

    Sissy Anal Pegging Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Anal
    Sissy Anal
    Anal Sissy
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    Best Videos
    By clicking the content you will also see an ad. AD
    Mistress Eudora's Anal Slut
    05:28
    Mistress Eudora's Anal Slut
    Loren Aprile
    145.2K views
    Girlfriend fuck transgirl with hard anal pegging
    05:20
    Girlfriend fuck transgirl with hard anal pegging
    RedLili
    25.2K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.8M views
    Girlfriend Makes Sissy Cum Hands Free Anal Pegging And Cum Eating Jessica Bloom And Polieana
    05:56
    Girlfriend Makes Sissy Cum Hands Free Anal Pegging And Cum Eating Jessica Bloom And Polieana
    Jessica Bloom
    26.9K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.3M views
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    06:00
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    Spike Essex
    18.2K 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
    637.4K views
    Sissy hypno slave getting ready for Anal pegging
    00:44
    Sissy hypno slave getting ready for Anal pegging
    5.5K views
    Anal Room Service with Mistress Lilith
    02:34
    Anal Room Service with Mistress Lilith
    Loren Aprile
    422.8K views
    Imagine You Are Fucking a Boy!
    06:15
    Imagine You Are Fucking a Boy!
    KinkyHome
    69.2K views
    Golden Shower and Piss Enema in the Garden for the Anal Slut
    01:18
    Golden Shower and Piss Enema in the Garden for the Anal Slut
    Loren Aprile
    377.4K views
    Femdom Strapon Pegging Cumshot!
    06:05
    Femdom Strapon Pegging Cumshot!
    KinkyHome
    747.6K 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
    Trans and TV CD Fuckfest
    11:12
    Trans and TV CD Fuckfest
    Mistress Jodie May
    94.6K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    The destruction of Jodie - MILF Lisa and TGirl Lucy anal fucking and pegging Jodie
    15:05
    The destruction of Jodie - MILF Lisa and TGirl Lucy anal fucking and pegging Jodie
    Spike Essex
    226K views
    Hardcore Pegging using my slave's ass to the limit
    02:21
    Hardcore Pegging using my slave's ass to the limit
    Revenge
    333K views
    College Pegging Part 2 - Miss Mk's Office - the Girls Get Dragged Into the Heads Office to Explain What They Have Been up to
    00:53
    College Pegging Part 2 - Miss Mk's Office - the Girls Get Dragged Into the Heads Office to Explain What They Have Been up to
    Jasmine_dlight
    128.4K views
    Pegging Hardcore with Mistress Revenge
    05:36
    Pegging Hardcore with Mistress Revenge
    Loren Aprile
    17.5K views
    Rough hardcore pegging in hospital
    07:47
    Rough hardcore pegging in hospital
    KinkyHome
    509.4K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Sissy CrossDresser Lucy gets pegged by Lisa with a Strapon
    46:18
    Sissy CrossDresser Lucy gets pegged by Lisa with a Strapon
    Spike Essex
    428.1K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    Goth Crossdresser Pegged and Swallows Own Cum
    10:08
    Goth Crossdresser Pegged and Swallows Own Cum
    Bailey Wilde
    40.2K views
    Anal Hike and Humiliation for TS Slave Loren Aprile
    02:09
    Anal Hike and Humiliation for TS Slave Loren Aprile
    Loren Aprile
    417.4K views
    HotTs Trans Ebony Jessica Black fucks Lance Hart’s Ass
    05:49
    HotTs Trans Ebony Jessica Black fucks Lance Hart’s Ass
    Hot TS
    197.2K views
    Open Up my Ass and Piss Inside
    02:23
    Open Up my Ass and Piss Inside
    Loren Aprile
    644.3K views
    AB121 Lustful succubus extreme training
    02:42
    AB121 Lustful succubus extreme training
    Abby Kitty
    156.6K views
    Rough Pegging for my Pig Slut Loren
    01:59
    Rough Pegging for my Pig Slut Loren
    Revenge
    245.8K views
    Trans Threesome Sissy Slut Jessica Bloom Gets Pegged While Sucking Cock
    06:32
    Trans Threesome Sissy Slut Jessica Bloom Gets Pegged While Sucking Cock
    Jessica Bloom
    225.5K views
    Sissy gets pegged
    04:31
    Sissy gets pegged
    195.7K views
    Mistress Jane and Gigi
    02:01
    Mistress Jane and Gigi
    136.3K views
    Mistress Revenge Destroying my Ass in her hotel room
    01:51
    Mistress Revenge Destroying my Ass in her hotel room
    Loren Aprile
    230.3K views
    Predicament Bondage
    22:28
    Predicament Bondage
    Twistedrama
    86.7K views
    why do I suddenly love trannys?
    12:46
    why do I suddenly love trannys?
    1.2M views
    Hard Hole Pegging
    05:33
    Hard Hole Pegging
    Lola Spais
    23.2K views
    Extreme Cock for Sissy Hole!!
    05:24
    Extreme Cock for Sissy Hole!!
    Lola Spais
    274.4K views
    Sissy Maid Pegged for Job
    05:22
    Sissy Maid Pegged for Job
    Bailey Wilde
    81K views
    Blond dominatrix pegging a shemale
    06:48
    Blond dominatrix pegging a shemale
    91.6K views
    Sissy Joyce humiliated and pegged by a goddess
    01:09
    Sissy Joyce humiliated and pegged by a goddess
    Sissy Joyce
    135.8K views
    Being Mistress Revenge's Sissy Slut
    02:04
    Being Mistress Revenge's Sissy Slut
    Loren Aprile
    90.2K views
    Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
    10:08
    Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
    Bailey Wilde
    47.3K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.5M views
    Jessica Bloom Cumshot Compilation 2024
    05:27
    Jessica Bloom Cumshot Compilation 2024
    Jessica Bloom
    40K views
    I finally let my stepsis fuck my trans pussy
    05:30
    I finally let my stepsis fuck my trans pussy
    CutePinkUnicorn
    606.2K views
    Post Op Shemale Lisa in Femdom Bondage & Pegging Sissy Lucy
    31:23
    Post Op Shemale Lisa in Femdom Bondage & Pegging Sissy Lucy
    Lisa Essex
    234K views
    Femdom pegging
    05:27
    Femdom pegging
    49.7K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Anal Pegging

    • Sissy Anal Stretch
    • Extreme Pegging
    • Femboy Ass
    • Crossdresser Butt Plug
    • Husband Pegged in Front of Wife
    • Traps Femboys and Sissys
    • Sissy Anal Orgasm
    • Anally Destroyed by a Big Dick Shemale
    • Cumming Hard With Butthole Twitching
    • Trans Pegging
    • Nylon Crossdressing Fetish
    • Sucking Cock Under the Table
    • Ladyboy Prostate Orgasm
    • Submissive Bottom
    • Beautiful Femboy Trap
    • Erotic Asmr
    • Cum From Behind
    • Tied up Gangbang
    • Two Sissies Crossdresser Bondage
    • Limp Sissygasm

    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