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
    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
    • Big Black Cock
    • Cum In Mouth
    • 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 Bitch
    Sissy Suck
    Sissy CEI
    Sissy Crying
    Sissy Hardcore
    Old Sissy
    Sissy Rough
    Fat Sissy
    Sissy Caught
    Degraded Sissies
    Indian Sissy
    Sissy Handjob
    Milking Machine
    Sissy Kissing
    Sissy CD
    Goon Sissy
    Sissy Bride
    Sissy Milking
    Sissy Interracial
    Skinny Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy Candy Is Fucked by Her Machine While in Chastity and Bondage Until She Has a Sissygasm
    07:45
    Sissy Candy Is Fucked by Her Machine While in Chastity and Bondage Until She Has a Sissygasm
    Sissy Candy
    21.2K views
    Cum Compilation New & Huge, Sissygams, No Hands Cum - Cums-compilation-full
    08:12
    Cum Compilation New & Huge, Sissygams, No Hands Cum - Cums-compilation-full
    JenniferStarTS
    2.3K views
    THROAT TRAINING ((LOW ANGLE))
    11:38
    THROAT TRAINING ((LOW ANGLE))
    Gsoqt
    17.2K views
    Shemale tranny gets head and sucks dick then gets fucked and used by a fuck machine
    30:18
    Shemale tranny gets head and sucks dick then gets fucked and used by a fuck machine
    DaddyandLexa
    19.6K views
    Doggy Style Fuck Machine
    08:26
    Doggy Style Fuck Machine
    Analslob
    2.1K views
    Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm
    13:05
    Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm
    Sissy Candy
    53.3K views
    Sissy Daddy's girl with fuck machine (not full)
    00:42
    Sissy Daddy's girl with fuck machine (not full)
    Letany Ponny
    66.7K views
    Creamy bbc
    06:31
    Creamy bbc
    parttcrossdresser
    22.5K views
    Fuck machine PMV
    05:40
    Fuck machine PMV
    Julie Shine
    12.1K views
    Amazing Fucking Machine Double Dildo Duel
    21:29
    Amazing Fucking Machine Double Dildo Duel
    Spike Essex
    7K views
    Femboy in purple remodels ass
    07:22
    Femboy in purple remodels ass
    Klarat
    1.9K views
    Sissy Kate learns how to use the anal fucking machine with Lisa
    15:14
    Sissy Kate learns how to use the anal fucking machine with Lisa
    Lisa Essex
    76.8K views
    Sex Toys Sissy Anal Orgasm Compilation
    01:20
    Sex Toys Sissy Anal Orgasm Compilation
    Sasha Q
    2K views
    Crossdresser gets machine fucked with XXL Monster Dildos #7
    10:07
    Crossdresser gets machine fucked with XXL Monster Dildos #7
    Niceguy_1991
    24.1K 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
    10K views
    Trans Girl Cums While Getting Machine Fucked
    04:05
    Trans Girl Cums While Getting Machine Fucked
    23.1K views
    Watch me being fucked in the ass by a machine from different angles
    06:12
    Watch me being fucked in the ass by a machine from different angles
    cd_vv
    12.3K views
    It Feels so Good to Use a Machine to Fuck My Asshole
    02:43
    It Feels so Good to Use a Machine to Fuck My Asshole
    cd_vv
    2.1K views
    Huge Ass Tranny Fucking Her Ass with Big Toys
    06:36
    Huge Ass Tranny Fucking Her Ass with Big Toys
    JenniferStarTS
    69.2K views
    Anal Slut Chained to the Fuck Machine by Her Balls
    06:48
    Anal Slut Chained to the Fuck Machine by Her Balls
    Priscilla Maria
    23.2K views
    King Cock 14 and 15 inch
    26:21
    King Cock 14 and 15 inch
    Ylvis88
    3.2K views
    Hand free cum from ass fucking
    03:33
    Hand free cum from ass fucking
    Casi CD
    21.3K views
    Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples
    08:14
    Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples
    fermerino
    2.2K views
    Anal fucking with XXL Dildos
    31:22
    Anal fucking with XXL Dildos
    Niceguy_1991
    53.6K views
    Sissy Gets Facial From Dildo Machine
    05:43
    Sissy Gets Facial From Dildo Machine
    MJ
    37.9K views
    My trans stepsister webcam gets fucked
    08:15
    My trans stepsister webcam gets fucked
    Smoker Master
    52.3K views
    Crazy Doggy Dirty Anal Fucking
    08:39
    Crazy Doggy Dirty Anal Fucking
    AsianSissy_Joey
    56.4K views
    Milking Machine Cumshot
    01:29
    Milking Machine Cumshot
    Felicity_cd
    33.8K views
    Throatfucking Machine Sissy Rough
    26:03
    Throatfucking Machine Sissy Rough
    Sissycdslc
    37.9K views
    Today's live session, me getting railed by viewers on xhamsterlive
    01:30:17
    Today's live session, me getting railed by viewers on xhamsterlive
    Ylvis88
    32K views
    Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom
    07:25
    Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom
    Jessica Bloom
    24.8K views
    As the Dildo That Looked Like a Toilet Brush Drove Me Crazy, Cum Sprayed All Over My Shoes
    02:05
    As the Dildo That Looked Like a Toilet Brush Drove Me Crazy, Cum Sprayed All Over My Shoes
    XiangYan
    17.2K views
    Sissy Slut Gooning While Using a Fuck Machine
    07:20
    Sissy Slut Gooning While Using a Fuck Machine
    KittyKaash
    13.9K views
    Fuck Machine Plows Sissy Asshole Deep And Hard - Anal Orgasm in Chastity
    07:27
    Fuck Machine Plows Sissy Asshole Deep And Hard - Anal Orgasm in Chastity
    Jessica Bloom
    6.4K views
    Doc J Dayski Dong pummeling my guts
    02:47
    Doc J Dayski Dong pummeling my guts
    Sparx134
    1.5K views
    Sissyrebelx gets her ass hard by her fuckmachine
    03:05
    Sissyrebelx gets her ass hard by her fuckmachine
    Sissyrebelx
    2.8K views
    Threesome fun with sexy MILF Lisa, horny TGirl Gigi and Bisexual DILF Mike - Part 1
    19:24
    Threesome fun with sexy MILF Lisa, horny TGirl Gigi and Bisexual DILF Mike - Part 1
    Lisa Essex
    43.1K views
    Baby fucked me and make me cum
    05:48
    Baby fucked me and make me cum
    Emmysdesire
    8.5K views
    T-Girl takes a big dildo and loves it
    07:05
    T-Girl takes a big dildo and loves it
    Jenni Wallace
    10K views
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    16:26
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    2.7K views
    Big Sissy CD Ass Pussy Fucked and Gaped Up Close
    04:14
    Big Sissy CD Ass Pussy Fucked and Gaped Up Close
    NKeyCD
    1.8K views
    Threesome Fun with Sexy MILF Lisa, Horny TGirl Gigi and Bisexual DILF Mike - Part 2
    17:07
    Threesome Fun with Sexy MILF Lisa, Horny TGirl Gigi and Bisexual DILF Mike - Part 2
    Lisa Essex
    47.5K views
    10.4 inch dildo slamming my big booty
    03:09
    10.4 inch dildo slamming my big booty
    Shy Boy
    8.5K views
    Rubberdoll Restrained and Rides the Sybian Multiple Precums and Orgasms
    39:14
    Rubberdoll Restrained and Rides the Sybian Multiple Precums and Orgasms
    Hooded June
    5K views
    I Cum From Everything That Goes Into My Ass
    01:29
    I Cum From Everything That Goes Into My Ass
    Sasha Q
    1.4K views
    F-Machine Fucked While Sucking Dick Jessica Bloom Gets Spitroasted With Julia Edge
    07:51
    F-Machine Fucked While Sucking Dick Jessica Bloom Gets Spitroasted With Julia Edge
    Jessica Bloom
    24.2K views
    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
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Sissy Machine

    • Shemales Brutal
    • Cash Twins
    • Fake Vagina Panties
    • Sissycdmish
    • Please Stop
    • Beautiful Model XXX
    • Feminized
    • Crazy Trannys
    • Milking Table
    • Familyxxx HD
    • Bad Dragon
    • Sarah N Tuned Naked
    • Ruthless
    • New Tits Surgery Implant
    • Sissyalicia
    • Twice
    • Transparent Lingerie Try on Haul
    • Cocks Under Skirt
    • Endless Deeply
    • Toyboy
    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