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
    • 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
    BLUE MONDAY SALE 💛🎉 Brighten the year’s saddest day
    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
    • Sissy
    • Shemale Fucks Girl
    • 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 Machine Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Machine
    Chastity Sissy Fucking Machine
    Sissy Fuck Machine Orgasm
    Sissy Fuck Machine Training
    Sissy Fuck Machine BBC
    Sissy Punishment Fucking Machine
    Sissy Fuck Machine Cum
    Anal Machine Chastity Sissy
    Latex Sissy Machine Fucking
    Sissy Deepthroating Fuck Machine
    Sissy Anal Machine Fuck Training
    Sissy With Cow Milking Machine
    Femdom Sissy Chastity Machine Fucked
    Sissy Gasm From Fuck Machine
    Sissy Training Tied to Fuck Machine
    Sissy Fucked Machine Get Prostate Orgasm
    Sissy Piss Gasm From Fuck Machine
    Sissy Crossdresser
    Sissy Training
    Best Videos
    By clicking the content you will also see an ad. AD
    Nice Slutty Anal session with 11 inches while online chatting away xx
    13:19
    Nice Slutty Anal session with 11 inches while online chatting away xx
    UksexyLegsTV
    2.2K views
    Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan
    04:01
    Redhead Sissy First Using a Sex-machine This Is a Sweet Gift From a Fan
    Sonechka25
    2.1K views
    Nasty Rem🤍Re:Zero Lewd face of a cute bunny girl cosplayer
    18:18
    Nasty Rem🤍Re:Zero Lewd face of a cute bunny girl cosplayer
    Nasty Azu
    45K views
    Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine
    11:26
    Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine
    Sissy Candy
    13.3K views
    I Lost to the Machine That Used Lightsaber, and I Lost Miserably
    03:01
    I Lost to the Machine That Used Lightsaber, and I Lost Miserably
    XiangYan
    3K views
    BBW sissy gurl fucking my asspussy dildo DP fuck machine.
    05:06
    BBW sissy gurl fucking my asspussy dildo DP fuck machine.
    12.8K views
    Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum
    08:07
    Chastity Sissy Cums From Big Black Cock Fucking Machine And Swallows Her Own Cum
    Jessica Bloom
    11.2K 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
    15.4K views
    cute tgirl DaniTheCutie painfully fucks herself with a very weird looking dildo
    05:05
    cute tgirl DaniTheCutie painfully fucks herself with a very weird looking dildo
    DaniTheCutie
    9.4K views
    Fucking Machine Sissy Anal Orgasm And Cum Play
    09:05
    Fucking Machine Sissy Anal Orgasm And Cum Play
    Jessica Bloom
    10.6K views
    Sissy Cum Best Compilation
    03:49
    Sissy Cum Best Compilation
    Sasha Q
    4.8K views
    Tgirl railed by fucking machine in thigh high PVC boots
    21:38
    Tgirl railed by fucking machine in thigh high PVC boots
    Holly unt
    22.4K views
    TGIRLS HOOKUP: Well Oiled Slut Machine is Desperate For Dick!
    01:59
    TGIRLS HOOKUP: Well Oiled Slut Machine is Desperate For Dick!
    Tgirls Hookup
    25.9K views
    Bimbo Playroom
    03:40
    Bimbo Playroom
    Nikki Pinkz
    30.6K views
    AB108 BadGirl FoxBae Training - Swallow,fucking machine,Futa,Femdom
    05:06
    AB108 BadGirl FoxBae Training - Swallow,fucking machine,Futa,Femdom
    Abby Kitty
    30.7K views
    Slut Goes Crazy on Fuck Machine
    09:16
    Slut Goes Crazy on Fuck Machine
    Analslob
    3.1K views
    Goddess Violet Presents: The Feminization of M
    01:55
    Goddess Violet Presents: The Feminization of M
    12.9K views
    Fisting training with machine
    17:15
    Fisting training with machine
    Niceguy_1991
    33.1K views
    sissy orgasm on a fucking machine !
    16:12
    sissy orgasm on a fucking machine !
    yourprettykate
    16.3K views
    FUCK MY ASS BY  FUCKING MACHINE
    13:28
    FUCK MY ASS BY FUCKING MACHINE
    Fogal101
    3.2K 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
    55.7K views
    Tranny getting fucked by sex machine till she cums without touching herself - UKsexylegsTV
    01:45
    Tranny getting fucked by sex machine till she cums without touching herself - UKsexylegsTV
    UksexyLegsTV
    46.6K views
    Long fucking machine session with multiple large toys
    01:28:33
    Long fucking machine session with multiple large toys
    Ylvis88
    31.6K views
    Tgirl Extreme Piss and Cumshot Fucking Machine
    01:11
    Tgirl Extreme Piss and Cumshot Fucking Machine
    Kimora Creams
    12.5K views
    Fuck Machine Super Cum Caged
    01:25
    Fuck Machine Super Cum Caged
    boobyb0y
    1.5K views
    Sissy Anal Compilation
    14:49
    Sissy Anal Compilation
    SissyDaniella
    1.6K views
    Emmysdesire's Compilation, sissy Cam Model Fuked by her fucking Machine
    11:36
    Emmysdesire's Compilation, sissy Cam Model Fuked by her fucking Machine
    Emmysdesire
    22.8K views
    Sissy Ylvis88 taking 17 inch giant dildo balls deep
    07:53
    Sissy Ylvis88 taking 17 inch giant dildo balls deep
    Ylvis88
    22.6K views
    Cumshot with fucking machine
    05:50
    Cumshot with fucking machine
    DWT_Dani
    4.9K views
    Hot compilation featuring amazing Alexandra Braces Star
    05:17
    Hot compilation featuring amazing Alexandra Braces Star
    Alexandra Braces
    2.9K views
    Sissy in Red playing with Sex Maschine
    12:40
    Sissy in Red playing with Sex Maschine
    SissyDaniella
    5.6K views
    Sissy Jasmine gets filled by THICK dildo
    10:52
    Sissy Jasmine gets filled by THICK dildo
    Jasmine904x
    1.3K views
    Testing out my sissy pussy with 2XL Boss Hogg
    54:54
    Testing out my sissy pussy with 2XL Boss Hogg
    Ylvis88
    30.4K views
    Fuck Machine Fun Part 2
    02:50
    Fuck Machine Fun Part 2
    TSJade95
    2.3K views
    Random strangers abuse my asspussy
    27:56
    Random strangers abuse my asspussy
    Niceguy_1991
    43.5K 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
    40.1K views
    There Is a Luminous Monster in My Room.
    02:43
    There Is a Luminous Monster in My Room.
    XiangYan
    9.3K views
    BBC fucks me hard
    10:07
    BBC fucks me hard
    parttcrossdresser
    17.8K views
    trans with sex machine on full speed getting a good pounding
    04:44
    trans with sex machine on full speed getting a good pounding
    UksexyLegsTV
    4.8K views
    Hard Cock Anal Orgasms From F Machine And Pegging - Jessica Bloom Prostate Milking
    05:27
    Hard Cock Anal Orgasms From F Machine And Pegging - Jessica Bloom Prostate Milking
    Jessica Bloom
    40.7K views
    PART 2 - Rimmed Twink Bred By Mature Dilf From Behind
    05:47
    PART 2 - Rimmed Twink Bred By Mature Dilf From Behind
    32.6K views
    Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
    08:25
    Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
    Sissy Candy
    609 views
    Teen Femboy Get Fucked by Machine
    06:32
    Teen Femboy Get Fucked by Machine
    Fembaby
    8.8K views
    My little swatter cock too soft for the wanker
    05:59
    My little swatter cock too soft for the wanker
    Moitsex
    1.8K views
    Hog Tied with Fucking Machine
    01:01
    Hog Tied with Fucking Machine
    Twistedrama
    47.5K views
    Making depth records - Fucking machine with 17 inch dildo
    12:11
    Making depth records - Fucking machine with 17 inch dildo
    Ylvis88
    38.2K views
    Cum Like a Sissy Slut - Sissy Captions
    05:13
    Cum Like a Sissy Slut - Sissy Captions
    JenniferStarTS
    8.8K views
    • Back
    • 1
    • ...
    • 5
    • 6
    • 7
    • 8
    • 9
    • ...
    • 80
    • Next

    Searches Related to Sissy Machine

    • Cant Handle
    • Sissies in Prison
    • Dubai Night Club
    • Trapped
    • Forced Orgasm
    • Taboo
    • Female Bodybuilder Lesbian
    • Rectal Prolapse
    • Ruined
    • When She Bigger Than You
    • Unlimited Steel
    • Amazing Oopsie Boobs
    • Transvestite Restaurant
    • Married Straight Man Breeds Again
    • Early Hormone Treatment Results
    • Nasty Amateurs
    • Xxxl
    • Best 2025
    • Nylon Masturbation Solo
    • Pervert Italian Family Complete Film
    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