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

    Working Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    She loves to be my favorite fucktoy in bareback
    05:36
    She loves to be my favorite fucktoy in bareback
    MrNastyXavier
    2M views
    Working from Home is so much fun with a Sissy Secretary.
    28:11
    Working from Home is so much fun with a Sissy Secretary.
    Lisa Essex
    113.2K views
    BBC Two Huge Cocks for Tight Little European Trans Ass
    08:12
    BBC Two Huge Cocks for Tight Little European Trans Ass
    Trans and Co
    259.9K views
    Petite sissy girl working out her hole
    01:06
    Petite sissy girl working out her hole
    AliceBloodyTears
    48.3K views
    He filled my ass with it, his drips a lot
    07:53
    He filled my ass with it, his drips a lot
    Piou_Sissy
    252.8K views
    I fuck my stepdaughter miste my husband is at work lesbian sex
    09:06
    I fuck my stepdaughter miste my husband is at work lesbian sex
    catalinagrande
    21.8K 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
    312.1K views
    I ended Covering his face with my Cum - Veronica Sanders
    05:22
    I ended Covering his face with my Cum - Veronica Sanders
    Veronica Sanders
    28.9K views
    sexy cd cums while getting fucked by BBC
    10:58
    sexy cd cums while getting fucked by BBC
    946.1K views
    Turned Into a Working Slut
    08:12
    Turned Into a Working Slut
    Pure Ts
    5.7K views
    I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
    05:59
    I ended up in this sissy hole. I love fucking and sucking a big dick and showing them what a real blowjob part4
    Rozebella
    161.7K views
    After-Work Indulgence of a Secret Trap OL
    06:35
    After-Work Indulgence of a Secret Trap OL
    Miyamizu Mitsuha
    1.8K views
    Lover fucked Vika Tverskaya rough
    06:04
    Lover fucked Vika Tverskaya rough
    vika_sissy
    77.6K views
    Work break
    08:12
    Work break
    TSRyley
    4.2K views
    Tgirl Squirting Literally Flashing Ass and Doing a Lot of Squirting
    08:12
    Tgirl Squirting Literally Flashing Ass and Doing a Lot of Squirting
    barbanegrazponto1onepov
    619.7K views
    Nancy from Day Work to Night Work
    16:11
    Nancy from Day Work to Night Work
    Nancy Rose
    44.9K views
    Pretty Blonde Femboy Fucked by BBC
    08:01
    Pretty Blonde Femboy Fucked by BBC
    Trans and Co
    207.7K views
    Pride Of My Work: Drooling Blowjob
    07:32
    Pride Of My Work: Drooling Blowjob
    Asura
    10.7K 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
    437K views
    Husband goes to work slut expands her hole when she is alone at home so that as soon as her husband arrives she will fuck him so that she is relaxed and happy
    08:16
    Husband goes to work slut expands her hole when she is alone at home so that as soon as her husband arrives she will fuck him so that she is relaxed and happy
    Usaberilx
    4K 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
    501.8K views
    Are You Ready for Our Daily "work Out"?
    05:45
    Are You Ready for Our Daily "work Out"?
    jiannalust
    11.2K views
    Femboy Fucked by this rascal with a bbc
    23:38
    Femboy Fucked by this rascal with a bbc
    Travsexysensuel
    283.1K views
    Shemale Ting Xuan Solo with Vibrators and Black High Heels at Work
    06:09
    Shemale Ting Xuan Solo with Vibrators and Black High Heels at Work
    Taiwancdgirl
    1.1K views
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    05:45
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    missangell_
    673.7K views
    Asian Trap Masturbation After Work
    20:25
    Asian Trap Masturbation After Work
    MaureenNadh
    52.7K views
    Fucking in all positions
    05:15
    Fucking in all positions
    Celine LAFFITE
    94.6K views
    Audrey tgirl: her hooker job and waits for her clients
    01:25
    Audrey tgirl: her hooker job and waits for her clients
    Audrey Tgirl
    51.1K views
    This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
    01:16
    This is how you treat a sissy slut! Guy uses tranny brutally in public and cums on her face!
    TV_Helena
    548.7K views
    Sissy working out and showing off
    04:30
    Sissy working out and showing off
    TeenBubbleButtSissy
    29.5K views
    Boss fucks the ass of delicious trans secretary
    07:40
    Boss fucks the ass of delicious trans secretary
    Marine Laveau
    193.3K views
    Sissy Vanessa works out with her new BBC dildos
    06:42
    Sissy Vanessa works out with her new BBC dildos
    Vane03_siss
    17.2K views
    Shemale and guy fuck till both cum
    13:31
    Shemale and guy fuck till both cum
    TSLuxylux
    1.9M views
    I Cross-dress and Masturbate with an Anal plug until I cum while the Mechanic Works in his Workshop.
    08:06
    I Cross-dress and Masturbate with an Anal plug until I cum while the Mechanic Works in his Workshop.
    fermerino
    1.7K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    Larissa1sexdoll. Trans Streethooker in Brussels
    01:06
    Larissa1sexdoll. Trans Streethooker in Brussels
    Larissa1sexdoll
    73.3K views
    Crossdresser shop owner gets fucked by a man in the shop
    13:00
    Crossdresser shop owner gets fucked by a man in the shop
    WanidaCrossdresser
    347.8K views
    train station slutwalk public whore exposed compilation
    09:06
    train station slutwalk public whore exposed compilation
    SusyTrav_AnalQueen
    8.6K views
    Fake Job Interview Bags a Crossdresser
    06:12
    Fake Job Interview Bags a Crossdresser
    Pure Ts
    32.9K views
    TsCammy sends this video to you while u are at work, what do you do?
    04:28
    TsCammy sends this video to you while u are at work, what do you do?
    Tscammy
    38.4K views
    handz free shemale cumming while getting fucked
    13:40
    handz free shemale cumming while getting fucked
    2.4M views
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    10:01
    Working on Sissy Slave Denise Humain Nipples for hours Part 1
    Denise Humain
    70.4K views
    Rubbing My Feet on the Guy's Cock and Licking My Feet and Sucking His Cock (foot Fetish) Creamy Cock. (valeria Toro)
    16:07
    Rubbing My Feet on the Guy's Cock and Licking My Feet and Sucking His Cock (foot Fetish) Creamy Cock. (valeria Toro)
    Valera Toro
    90.2K views
    When you don't feel like going to work
    05:22
    When you don't feel like going to work
    Emily Rossi
    21.5K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Work it sissy trainer
    07:04
    Work it sissy trainer
    261.7K views
    Girl forgot to tell her Tinder date that she’s Trans
    07:22
    Girl forgot to tell her Tinder date that she’s Trans
    JsseMontz
    638.7K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Working Sissy

    • Giving Him an Experience
    • Schoolgirl
    • Drag Queen Fucks Guy
    • Feminization Bondage
    • Cuckold Wife BBC
    • Trap in Lingerie
    • Slutwife Secrets
    • Combat Zone Transsexual Barebacking
    • Sisy Boy
    • Female Domination
    • Sissy-Virgin
    • Panty Tease
    • Stockings Bareback
    • Extrem Crossdressers
    • Men Dressed as Women
    • A Sissy's Purpose
    • Straight Guys Fantasy
    • Sissysubkrystal
    • Amateur Tgirl
    • Couple Dominated

    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