PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    Sissy Machine Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Anal
    Sissy Caption
    Sissy Bondage
    Sissy Trainer
    Transvestites Sissies
    Asian Sissy
    Homemade Sissy
    Fucking Machine
    Sissy JOI
    Sissy BDSM
    Sissy Daddy
    Sissy Pegging
    Sissy Femboy
    Black Sissy
    Russian Sissy
    Sissy Maker
    Sissy Dildo
    Mature Sissy
    Sissy Brainwash
    Mommy Sissy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Riding My Fuck Machines Big Black Dildo and It Destroys My Tight Trans Ass!!
      08:41
      Riding My Fuck Machines Big Black Dildo and It Destroys My Tight Trans Ass!!
      PrincessKitti3
      16.6K views
    • Dirty Bitch Punishes Ass
      09:46
      Dirty Bitch Punishes Ass
      Analslob
      3.8K views
    • Big Ass Sissy In Yellow Lingerie Fucked to Double Sissygasm by Fucking Machine
      01:30
      Big Ass Sissy In Yellow Lingerie Fucked to Double Sissygasm by Fucking Machine
      NKeyCD
      5.2K views
    • Creamy Ass Fuck
      05:06
      Creamy Ass Fuck
      Analslob
      10.7K views
    • Punish Chair, Let Me Cum to Becoming a Fountain
      03:18
      Punish Chair, Let Me Cum to Becoming a Fountain
      XiangYan
      4.5K views
    • Jessica Bloom Cumshot Compilation 2024
      05:27
      Jessica Bloom Cumshot Compilation 2024
      Jessica Bloom
      40K views
    • Hard anal machine making me cum. Big dildo in my round ass feels great. Deep creamy assfuck.
      28:53
      Hard anal machine making me cum. Big dildo in my round ass feels great. Deep creamy assfuck.
      Bootyanal
      48.4K views
    • Spinning dildo on fucking machine
      01:15
      Spinning dildo on fucking machine
      AmandaKnight
      21.1K 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
    • Hung Tgirl railed by fucking machine Holly Hunt in cute blue lingerie
      07:08
      Hung Tgirl railed by fucking machine Holly Hunt in cute blue lingerie
      Holly unt
      76.2K views
    • Trans Dom CEI With Cock Milking Machine - Swallow Our Cum Slut
      08:40
      Trans Dom CEI With Cock Milking Machine - Swallow Our Cum Slut
      Jessica Bloom
      22.1K views
    • trans girl pounded with tons of cum lube on fuck machine :)
      01:33
      trans girl pounded with tons of cum lube on fuck machine :)
      amyy_babyy_x
      106.5K views
    • sissy sarah tits milking machine
      03:39
      sissy sarah tits milking machine
      Sissy_sarah69
      64K 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
      19.1K views
    • Getting Fucked By BBC Fucking Machine
      07:31
      Getting Fucked By BBC Fucking Machine
      Bottom Jen
      45.4K views
    • Anal masturbation and hands free cum on the fucking machine for TGirl Lucy
      16:30
      Anal masturbation and hands free cum on the fucking machine for TGirl Lucy
      Spike Essex
      34K views
    • Xmas fun with fuck machine
      08:29
      Xmas fun with fuck machine
      yourprettykate
      3.1K views
    • Stupid and Stuffed
      02:45
      Stupid and Stuffed
      Nikki Pinkz
      58.8K views
    • Double Stuffed Bimbo
      09:50
      Double Stuffed Bimbo
      Kapri Sun
      40.1K views
    • fucking machine squirt
      21:48
      fucking machine squirt
      Juahlovely
      92.9K views
    • Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
      08:25
      Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
      Sissy Candy
      20.8K views
    • Relevant Short videos

      Sissy machine gape
      Sissy machine gape
      nwiguy86
      264 views
      Milking Machine Makes Cow Slut Cum
      Milking Machine Makes Cow Slut Cum
      Roxie Black
      121K views
      GO HARD OR GO HOME XXX - Slut seeing how fast she can take with this huge dildo on her sex machine - UKsexylegsTV
      GO HARD OR GO HOME XXX - Slut seeing how fast she can take with this huge dildo on her sex machine - UKsexylegsTV
      UksexyLegsTV
      54.7K views
      Bent Over Milking for Cow Slut
      Bent Over Milking for Cow Slut
      Roxie Black
      110.8K views
      Milking Machine Makes Slut Moo Like A Bitch
      Milking Machine Makes Slut Moo Like A Bitch
      Roxie Black
      42K views
      Holy machine orgasm
      Holy machine orgasm
      boobyb0y
      23.1K views
    • Fucking Machine Makes Crazy Sissy Squirt
      13:55
      Fucking Machine Makes Crazy Sissy Squirt
      AsianSissy_Joey
      54.2K views
    • Tgirl moaning and fuck machine
      03:19
      Tgirl moaning and fuck machine
      Letany Ponny
      150.1K views
    • Fucking Machine Fucks Sissy Femboy
      07:09
      Fucking Machine Fucks Sissy Femboy
      Bottom Jen
      48.9K views
    • fucking machine sissygasm backview
      10:32
      fucking machine sissygasm backview
      Juahlovely
      18.4K views
    • Sideview of Artemis 115
      34:23
      Sideview of Artemis 115
      Ylvis88
      26.4K views
    • Fucking My Ass with Huge Dildos and Cum
      07:22
      Fucking My Ass with Huge Dildos and Cum
      JenniferStarTS
      62.1K views
    • Chastity cage and fuck machine are best present
      07:50
      Chastity cage and fuck machine are best present
      yourprettykate
      3.5K views
    • Naughty Maid, Big Squirt Whilst Her Pussy Is Being Fucked
      03:13
      Naughty Maid, Big Squirt Whilst Her Pussy Is Being Fucked
      JessicaXD
      2.2K views
    • Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      13:54
      Pvc Catsuit Sissy Gets Fucked by and Fucks Her Sex Toy Doll While Locked in Chastity and Has a Sissygasm
      Sissy Candy
      39.6K 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
      7.3K views
    • Tiny Dick Shemales Having a Sissygasm -sissy Captions
      06:20
      Tiny Dick Shemales Having a Sissygasm -sissy Captions
      JenniferStarTS
      28.8K views
    • A redhead getting butt-fucked from behind
      12:26
      A redhead getting butt-fucked from behind
      Sabrina Iu
      58.6K views
    • Spandexfemboy - Anal Destruction Part 2 BBC Dildo
      35:11
      Spandexfemboy - Anal Destruction Part 2 BBC Dildo
      Spandexlover89
      12.7K views
    • Small Dick Sissy Playing with a Fuck Machine - Sissy Captions
      05:38
      Small Dick Sissy Playing with a Fuck Machine - Sissy Captions
      JenniferStarTS
      16.2K views
    • Sissy compilation
      07:29
      Sissy compilation
      Sissy_Sasha_Q
      54.4K views
    • Sissy Evolution 2: Be Happy. Be a Bimbo
      06:08
      Sissy Evolution 2: Be Happy. Be a Bimbo
      Tiffany Cox
      4.2K views
    • OMG! Whore gets creamy fucked
      05:10
      OMG! Whore gets creamy fucked
      Starbutts
      24.6K views
    • extreme nymphomaniac
      08:05
      extreme nymphomaniac
      TSquennAna
      23.8K views
    • BBW Sissy gurl playing with fuck machine
      01:30
      BBW Sissy gurl playing with fuck machine
      42.4K views
    • Double Machine
      05:36
      Double Machine
      Nikki Pinkz
      105K views
    • Requested fully naked fucking machine short session with moaning
      02:19
      Requested fully naked fucking machine short session with moaning
      Ylvis88
      53.3K views
    • fucking my huge gape 🕳️
      00:50
      fucking my huge gape 🕳️
      amyy_babyy_x
      86.9K views
    • Sissy creamy fuck machine with big cum
      06:51
      Sissy creamy fuck machine with big cum
      Muckyfun
      39.6K views
    • Caged Arab Sissy Amina balls-deep gaping on a BBC dildo
      22:06
      Caged Arab Sissy Amina balls-deep gaping on a BBC dildo
      Sissy Amina
      17.6K views
    • Just my deep Belly Bulge training
      01:49
      Just my deep Belly Bulge training
      Miolee
      48.2K views
    • Analslob"s Stream 7.13
      19:46
      Analslob"s Stream 7.13
      Analslob
      3.2K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    9. ...
    10. 80
    80

    Searches Related to Sissy Machine

    • Submissive Transvestite Training
    • Ball Gag
    • Cat Girl
    • Homemade Rough
    • Bbc Whore
    • Petite Chloe
    • Legs Wide Open While Jerking Cock
    • Cums Three Times
    • Deep Fisting
    • Ladyboy Handsfree
    • Self Bondage
    • Emo Goth TS
    • Feminization
    • Brutal Pegging
    • Smoking During Gang Bang 1
    • Prostate Orgasm Tutorial
    • Pain Slut
    • Sissy-Kuroko
    • Wiki Se'lai
    • Dildoing
    Monetize your content
    Become a creator

    xHamster

    • About us
    • 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

    Earn money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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