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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Machine Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Chastity Sissy Machine Ballbusting
    01:25
    Chastity Sissy Machine Ballbusting
    suckyoudry76
    19.1K views
    Tgirl Fucks an Horny Latina Slut!
    21:42
    Tgirl Fucks an Horny Latina Slut!
    Leyne Rodriguez
    108K views
    Fuck machine anal orgasm
    03:04
    Fuck machine anal orgasm
    Sissy-boys
    90.1K views
    21 inches in my ass! BULGE. I'm cumming while a dildo stirs my stomach
    07:08
    21 inches in my ass! BULGE. I'm cumming while a dildo stirs my stomach
    Starlightfemboy
    476.6K views
    this fuck machine goes so deep omg 😵
    01:10
    this fuck machine goes so deep omg 😵
    amyy_babyy_x
    276.7K views
    trans girl gets railed by even BIGGER Hankey’s Toys XXXCALIBUR with fuck machine
    02:30
    trans girl gets railed by even BIGGER Hankey’s Toys XXXCALIBUR with fuck machine
    amyy_babyy_x
    415.7K views
    Sexy tgirl in bodysuit gets fucked by fuckmachine and cums
    02:43
    Sexy tgirl in bodysuit gets fucked by fuckmachine and cums
    Starlightfemboy
    204.8K views
    Trans Slut Fits Two Huge Dicks, Balls Deep in Her Holes at the Same Time
    10:02
    Trans Slut Fits Two Huge Dicks, Balls Deep in Her Holes at the Same Time
    MJ
    15.8K views
    Trans on a Fuckmachine for Her Neighbor
    06:44
    Trans on a Fuckmachine for Her Neighbor
    Emmy Angeles
    24.4K views
    Paula Rainbow takes her first spin on a fucking machine
    07:06
    Paula Rainbow takes her first spin on a fucking machine
    Paula Rainbow
    7.1K views
    Sissy slut spitroast training with my fuck machine and dildos
    03:05
    Sissy slut spitroast training with my fuck machine and dildos
    trixied93
    3.9K views
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    16:04
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    Sissy Candy
    15.2K views
    Sissy slut Sasha Q anal orgasm compilation collection
    07:09
    Sissy slut Sasha Q anal orgasm compilation collection
    Sissy_Sasha_Q
    99.4K views
    fucking machine sissygasm backview
    10:32
    fucking machine sissygasm backview
    Juahlovely
    17.2K views
    Spandexfemboy - Anal Destruction Part 2 BBC Dildo
    35:11
    Spandexfemboy - Anal Destruction Part 2 BBC Dildo
    Spandexlover89
    12.7K views
    Tgirl moaning and fuck machine
    03:19
    Tgirl moaning and fuck machine
    Letany Ponny
    149.1K views
    Patricia Wolford - Machine fucks with XL dildo the sissy in stockings and high heels
    09:36
    Patricia Wolford - Machine fucks with XL dildo the sissy in stockings and high heels
    Patricia Wolford
    18K views
    Fucking Machine Fucks Sissy Femboy
    07:09
    Fucking Machine Fucks Sissy Femboy
    Bottom Jen
    47.9K views
    Bang my ass with your fat dick - Chantal needs it hard
    04:26
    Bang my ass with your fat dick - Chantal needs it hard
    Sissy Slut Chantal Sweet
    6.2K views
    Sissy creamy fuck machine with big cum
    06:51
    Sissy creamy fuck machine with big cum
    Muckyfun
    39.6K views
    Just my deep Belly Bulge training
    01:49
    Just my deep Belly Bulge training
    Miolee
    47.1K views
    White CD Sissy Whore's Ass Destroyed by Massive black dildo
    05:55
    White CD Sissy Whore's Ass Destroyed by Massive black dildo
    NKeyCD
    2.6K views
    Femboy Pounded Nice and Hard
    03:19
    Femboy Pounded Nice and Hard
    Shy Boy
    17.3K views
    This is How You Learn to Love Cock Down Your Throat More then Breathing - Training
    08:13
    This is How You Learn to Love Cock Down Your Throat More then Breathing - Training
    MJ
    30.6K views
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    17:10
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    Spandexlover89
    2.6K views
    ANAL MASTERBATION BY FUCKINGMACHINE THROUGH PANTYHOSE
    06:26
    ANAL MASTERBATION BY FUCKINGMACHINE THROUGH PANTYHOSE
    Fogal101
    20.6K views
    My bitch wants two dicks in her big ass
    06:45
    My bitch wants two dicks in her big ass
    Saranji
    21.1K views
    femboy in pink gets asshole remodeled
    04:14
    femboy in pink gets asshole remodeled
    Klarat
    41.4K views
    MILF gives Titty Fuck and get rimmed until she squirts her juicy cum
    10:27
    MILF gives Titty Fuck and get rimmed until she squirts her juicy cum
    Sissy Slut Chantal Sweet
    86K views
    Sissy Daddy's girl with fuck machine (not full)
    00:42
    Sissy Daddy's girl with fuck machine (not full)
    Letany Ponny
    66.1K views
    White Sissy Bubble Butt Fucked by Machine and Huge Dildo
    05:55
    White Sissy Bubble Butt Fucked by Machine and Huge Dildo
    NKeyCD
    1.7K views
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    16:26
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    Spandexlover89
    2.4K views
    Latex Sissy Maid Fucked by Machine and Plays with Her Sex Doll Toy
    21:40
    Latex Sissy Maid Fucked by Machine and Plays with Her Sex Doll Toy
    Sissy Candy
    9.5K views
    10.4 inch dildo slamming my big booty
    03:09
    10.4 inch dildo slamming my big booty
    Shy Boy
    8.2K views
    Sissy in teal dress and pantyhose cums hard with prostate machine
    04:55
    Sissy in teal dress and pantyhose cums hard with prostate machine
    Nylonizer
    1.2K views
    Sissy Gets Facial From Dildo Machine
    05:43
    Sissy Gets Facial From Dildo Machine
    MJ
    37.5K views
    Doc J Dayski Dong pummeling my guts
    02:47
    Doc J Dayski Dong pummeling my guts
    Sparx134
    1.3K views
    Sissy Slut Gooning While Using a Fuck Machine
    07:20
    Sissy Slut Gooning While Using a Fuck Machine
    KittyKaash
    13.2K views
    SISSY TRAIN WITH BIG TOY FUCKING MACHINE
    06:00
    SISSY TRAIN WITH BIG TOY FUCKING MACHINE
    Fogal101
    2.4K views
    FUCK MY ASS BY  FUCKING MACHINE
    13:28
    FUCK MY ASS BY FUCKING MACHINE
    Fogal101
    2.2K views
    THROAT TRAINING ((LOW ANGLE))
    11:38
    THROAT TRAINING ((LOW ANGLE))
    Gsoqt
    16.7K views
    Sissy CD Femboy in Red Ass Fucked by Machine for 40 minutes
    43:50
    Sissy CD Femboy in Red Ass Fucked by Machine for 40 minutes
    NKeyCD
    990 views
    Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
    10:30
    Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
    G8pess
    15K views
    trans girl stuffed by fuck machine (Double POV) with huge Hankey's Toys XXXCALIBUR
    02:15
    trans girl stuffed by fuck machine (Double POV) with huge Hankey's Toys XXXCALIBUR
    amyy_babyy_x
    55.1K views
    Chastity gets Vibrated Her Clitty Projectile Squirt Cummies, her tiny balls SPANKED, & Turning the Fuck Machine Up to its Max!
    06:20
    Chastity gets Vibrated Her Clitty Projectile Squirt Cummies, her tiny balls SPANKED, & Turning the Fuck Machine Up to its Max!
    MJ
    20.7K views
    Strapped to Fucking Machine Chair in PVC Catsuit Gagged in Chastity
    14:41
    Strapped to Fucking Machine Chair in PVC Catsuit Gagged in Chastity
    Derek6699
    39.7K views
    Solo Orgasm Sissy Sasha Q
    01:11
    Solo Orgasm Sissy Sasha Q
    Sasha Q
    1.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Machine

    • Fuck Machine Extreme Fast
    • Shemale Sex Machines
    • Sissy Femboy Fucked
    • Dildo Sissygasm
    • Fuck Machine Orgasm
    • Traps Femboys and Sissys
    • Daddy Fucking Sissy Femboy
    • Secret Sissyboy
    • Feminization Bondage
    • Sissy-Boys
    • White Boy Becomes Bitch for BBC
    • Sissy Femboy
    • Femboys and Sissys
    • The Sissy's Future
    • Big Ass Tranny Doggystyle
    • Grindr Trans
    • Boys Wearing High Heels
    • Mistress Pussy Licking Femdom
    • Sissyslut
    • Fuck Machine Cum

    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