PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Sissy First Machine Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Cock Milking Machine Makes me Squirt HUGE Load of Cum - Jessica Bloom Cumswallow
      10:22
      Cock Milking Machine Makes me Squirt HUGE Load of Cum - Jessica Bloom Cumswallow
      Jessica Bloom
      197.2K views
    • X-mas night with huge toys and fucking machine
      01:03:42
      X-mas night with huge toys and fucking machine
      Ylvis88
      58.9K 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
      17.3K views
    • Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
      07:12
      Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
      Jessica Bloom
      200.2K views
    • One more go with king cobra and fucking machine
      05:41
      One more go with king cobra and fucking machine
      Ylvis88
      218.7K views
    • Sissy in chastity and monster fuck machine
      07:41
      Sissy in chastity and monster fuck machine
      yourprettykate
      37.5K views
    • "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
      03:01
      "i Work in the Seventh Heaven Bar." "you Are a Waiter?" "no I'm a Milk Maker.
      XiangYan
      53K views
    • Chastity ass pounded sissy
      03:43
      Chastity ass pounded sissy
      Lockedupunicorn
      55.6K views
    • Cow Slut Gets Milked
      01:05
      Cow Slut Gets Milked
      Roxie Black
      204.9K views
    • Devil May Play
      03:18
      Devil May Play
      XiangYan
      29.3K views
    • blonde femboy fuck machine sissy training!
      13:20
      blonde femboy fuck machine sissy training!
      Cassie Coyote
      94.9K views
    • Femboy slut and big black dildo
      06:38
      Femboy slut and big black dildo
      Liza Femb
      8.7K views
    • Just a horny day and sissy driving huge toys in her pussy, double penetration, fisting
      01:22:28
      Just a horny day and sissy driving huge toys in her pussy, double penetration, fisting
      Ylvis88
      161.4K views
    • Merciless Strappado Machine
      01:09
      Merciless Strappado Machine
      Twistedrama
      114.7K views
    • Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
      06:54
      Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
      Jessica Bloom
      5K views
    • Valda's spurting anal juices
      02:07
      Valda's spurting anal juices
      Lady Valda
      145.2K views
    • Trans on a Fuckmachine for Her Neighbor
      06:44
      Trans on a Fuckmachine for Her Neighbor
      Emmy Angeles
      26.1K views
    • Fuck Machine - Anal disassembly
      09:12
      Fuck Machine - Anal disassembly
      LaurelineTV
      72.4K views
    • Finally all in with 15 inch King Cock dildo
      43:06
      Finally all in with 15 inch King Cock dildo
      Ylvis88
      7.9K views
    • Sissy Fuck Machine Training
      07:39
      Sissy Fuck Machine Training
      Mistress Jodie May
      79.9K views
    • A Femboy Is Cuming,and There Are the Changes of His Feet.
      03:19
      A Femboy Is Cuming,and There Are the Changes of His Feet.
      XiangYan
      12.5K views
    • Punish Chair, Let Me Cum to Becoming a Fountain
      03:18
      Punish Chair, Let Me Cum to Becoming a Fountain
      XiangYan
      6.2K views
    • Fucking Machine And Cock Milking Machine Drains Transgirl Balls - Jessica Bloom
      08:29
      Fucking Machine And Cock Milking Machine Drains Transgirl Balls - Jessica Bloom
      Jessica Bloom
      45.1K views
    • Bad Dragon XL Pedro fully in me
      16:11
      Bad Dragon XL Pedro fully in me
      Ylvis88
      9.3K views
    • Sissy fucked with some monster dildos
      42:25
      Sissy fucked with some monster dildos
      Niceguy_1991
      319.5K views
    • Locked, Submissive Trans Sissy in Long Machine Play
      13:58
      Locked, Submissive Trans Sissy in Long Machine Play
      Paula Rainbow
      7.3K views
    • Sissy slut Sasha Q anal orgasm compilation collection
      07:09
      Sissy slut Sasha Q anal orgasm compilation collection
      Sissy_Sasha_Q
      101K views
    • Blonde Trans Fisting Silicone Pussy
      06:22
      Blonde Trans Fisting Silicone Pussy
      Nicole Nicolette
      10.7K views
    • Tranny femdom! Slave gets tranny doms piss and ist fucked by her and fucking machine!
      00:43
      Tranny femdom! Slave gets tranny doms piss and ist fucked by her and fucking machine!
      TV_Helena
      148.7K views
    • Trans Christmas Sissy Elf Milked by Fucking Machine With Huge Dildo! - Jessica Bloom
      08:42
      Trans Christmas Sissy Elf Milked by Fucking Machine With Huge Dildo! - Jessica Bloom
      Jessica Bloom
      71.5K views
    • 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
      17.4K views
    • Double Electric Shock Cum
      02:05
      Double Electric Shock Cum
      XiangYan
      18.3K views
    • Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times
      10:08
      Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times
      Jessica Bloom
      157.7K 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
      49.4K views
    • Creamy Ass Fuck
      05:06
      Creamy Ass Fuck
      Analslob
      11.8K 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
      77.2K views
    • BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
      06:47
      BBC Fucking Machine Makes Sissy Cum Hard in Chastity!
      Jessica Bloom
      4K views
    • Xmas fun with fuck machine
      08:29
      Xmas fun with fuck machine
      yourprettykate
      4.4K views
    • Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
      07:55
      Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
      Sissy Candy
      45.8K views
    • Dirty Bitch Punishes Ass
      09:46
      Dirty Bitch Punishes Ass
      Analslob
      4.6K views
    • Naughty Maid, Big Squirt Whilst Her Pussy Is Being Fucked
      03:13
      Naughty Maid, Big Squirt Whilst Her Pussy Is Being Fucked
      JessicaXD
      3.5K views
    • sissy sarah tits milking machine
      03:39
      sissy sarah tits milking machine
      Sissy_sarah69
      65.4K views
    • Playing with tiny anal dildo
      09:49
      Playing with tiny anal dildo
      Ylvis88
      8.9K 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
      6.8K views
    • Fucking My Ass with Huge Dildos and Cum
      07:22
      Fucking My Ass with Huge Dildos and Cum
      JenniferStarTS
      62.1K 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
      20.3K 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
      23.3K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    9. ...
    10. 80
    80

    Categories

    American
    4K Porn
    HD Videos
    VR Porn
    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
    Masturbation
    Domination
    Anal
    Brazilian
    Solo
    Asian
    Transgender
    BBW
    Mexican
    Cartoon
    Interracial
    Vintage
    Japanese
    Big Tits
    Young
    Small Cock
    Thai
    Lingerie
    Trans Woman
    Gangbang
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Rough Sex
    Couple
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Outdoor
    Handjob
    Chinese
    Fetish
    Hentai
    FTM
    Group Sex
    Massage
    Bondage
    Pissing
    British
    Double Penetration
    Role Play
    Behind The Scenes
    German
    Anal Toy
    SFW
    All categories
    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