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

    Sissy Work Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Boy
    Sissy Slut
    Sissy Cum
    Sissy Creampie
    Sissy Humiliation
    Sissy Anal
    Sissy Caption
    Sissy Bondage
    Asian Sissy
    Sissy Trainer
    Homemade Sissy
    Sissy JOI
    Transvestites Sissies
    Sissy Daddy
    Sissy BDSM
    Sissy Pegging
    Sissy Femboy
    Black Sissy
    Sissy Maker
    Sissy Dildo
    Best Videos
    By clicking the content you will also see an ad. AD
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    08:12
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    nbnabunny
    1.6M views
    "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
    03:01
    "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
    XiangYan
    53K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    376.9K views
    Sexy Thick sissy in fishnets at work
    05:29
    Sexy Thick sissy in fishnets at work
    Ruby Robby
    48.5K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    Sissy BBC Work
    08:05
    Sissy BBC Work
    77.9K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    106.2K views
    Sissy coming home from work
    16:12
    Sissy coming home from work
    SissyDaniella
    20K views
    Her ass can fit all my big black cock so good
    06:21
    Her ass can fit all my big black cock so good
    MrNastyXavier
    1.8M views
    The Queen is largely derived from this work
    32:28
    The Queen is largely derived from this work
    Reynaldo6
    50.9K views
    Night. Park. Car. Fucked a trans slut.
    07:18
    Night. Park. Car. Fucked a trans slut.
    vika_sissy
    229.5K views
    Work Sissy
    06:12
    Work Sissy
    Pure Ts
    2.9K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    692K views
    Your Work Review
    05:17
    Your Work Review
    Cassandra Lovit
    91.2K views
    Completely Submitted and Feminized
    08:12
    Completely Submitted and Feminized
    Pure Ts
    48.6K views
    Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!
    01:17
    Cleaning slave working hard for cute tranny girl! Spitting! Assfuck! Mouthfuck! Deepthroat! Cum in mouth!
    TV_Helena
    18.4K views
    Fucking on the last day of summer, in a cornfield
    03:39
    Fucking on the last day of summer, in a cornfield
    vika_sissy
    342.8K views
    sissy bitch works step daddys bbc with her mouth and throat
    08:55
    sissy bitch works step daddys bbc with her mouth and throat
    73.8K views
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    09:05
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    Adam Castle
    365K views
    Work Sissy
    06:12
    Work Sissy
    Pure Ts
    2.7K views
    Tgirls Closeup Cumshot Compilation for Sissy
    25:07
    Tgirls Closeup Cumshot Compilation for Sissy
    3.4M views
    After work guy fucks trans cute girl
    07:26
    After work guy fucks trans cute girl
    LittleVixenSlut
    5.4K views
    I had a big cumshot in unkown hotel
    05:39
    I had a big cumshot in unkown hotel
    Samantha Sissy World
    1.5M views
    He Doent Let Me Work so Naughty
    10:24
    He Doent Let Me Work so Naughty
    Stripchat official
    566.2K views
    Your little bitch wants hot cum inside her tight and dirty asshole
    06:50
    Your little bitch wants hot cum inside her tight and dirty asshole
    missangell_
    754K views
    The New Maid Is Gonna Work Out Just Fine
    06:12
    The New Maid Is Gonna Work Out Just Fine
    Pure Ts
    2.6K views
    Sissy Dreams 3
    26:07
    Sissy Dreams 3
    1.2M views
    A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
    13:59
    A tempting secretary changed her stocking after work and inserted anal plug without panty to prepare for the secret nightwork.
    Harinni
    5.2K views
    Tgirl Riley offers her little ass in the hallway
    20:16
    Tgirl Riley offers her little ass in the hallway
    Tgirl Riley
    94.1K views
    busy truck stop whore slutwalk naked caught outdoor strangers
    02:25
    busy truck stop whore slutwalk naked caught outdoor strangers
    SusyTrav_AnalQueen
    8.5K views
    Sissy cums too early and gets punished with rough fucking
    02:35
    Sissy cums too early and gets punished with rough fucking
    2.1M views
    Work Underling Becomes Secret Sissy Fucktoy
    08:12
    Work Underling Becomes Secret Sissy Fucktoy
    Pure Ts
    8.2K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Showing myself off in my red bodycon dress. I get myself a little worked up again.
    06:27
    Showing myself off in my red bodycon dress. I get myself a little worked up again.
    JessicaXD
    1.8K views
    A Prostitute Offering Herself on the Street
    02:29
    A Prostitute Offering Herself on the Street
    Wesley Fudedor
    332.8K views
    How Should a Sissy at Work Dress
    03:26
    How Should a Sissy at Work Dress
    59.7K views
    Daddy Milks Trans Girl Prostate
    05:06
    Daddy Milks Trans Girl Prostate
    Gray Perrier
    327.5K views
    The First Thing He Does After Work
    07:42
    The First Thing He Does After Work
    Pure Ts
    5.7K views
    Two Sissy Slut play sexual games
    15:33
    Two Sissy Slut play sexual games
    IskraElectrical49
    147.1K views
    Working that mouth
    05:20
    Working that mouth
    Pandora Xysishe
    18.6K views
    On My Knees and They Fill My Mouth with Lots of Milk
    14:18
    On My Knees and They Fill My Mouth with Lots of Milk
    Valera Toro
    493.3K views
    Playing in pretty panties
    03:12
    Playing in pretty panties
    Rachel_biTV_uk
    35.9K 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
    217.2K views
    Muscled Sissy Working Out Crazy Public Gym Exposure Cumshot
    06:52
    Muscled Sissy Working Out Crazy Public Gym Exposure Cumshot
    Sissy Jessica
    50.3K views
    Behind the Scenes of a Porn Video Featuring a Beautiful European Trans Woman.
    01:13:48
    Behind the Scenes of a Porn Video Featuring a Beautiful European Trans Woman.
    Trans and Co
    156.7K views
    outdoor full naked chastity heels slutwalk at truck stop
    02:25
    outdoor full naked chastity heels slutwalk at truck stop
    SusyTrav_AnalQueen
    5.8K views
    Sissy Femboy Fucked From Behind
    05:20
    Sissy Femboy Fucked From Behind
    2.7M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Work

    • Femboy Gangbang
    • First Time Crossdressing
    • Cd BDSM
    • Crossdresser Hubby Fucked
    • Hot Femboys
    • Trans Gangbanged
    • Tranny Slut
    • Crossdressers Hardcore
    • Teen Destroyed
    • SissyCDSD Leaked
    • Extreme Pain
    • Sissies Fucking
    • Sissynat
    • Interracial Domination
    • Permanent Sissification
    • Chastity Slave
    • Sissypink Boy
    • Feminization
    • Sissy4bbc
    • Bbc Orgy

    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