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

    Fuck Machine Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the gay section?
    Sissy
    Fuck
    Machine
    Sissy Fuck Machine
    Sissy Fucked
    Fucking Machine
    Fuck Sissy
    Machine Fuck
    Sissy Fuck Machine Orgasm
    Sissy Fuck Machine BBC
    Sissy Fuck Machine Cum
    Sissy Deepthroating Fuck Machine
    Sissy Anal Machine Fuck Training
    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
    Femboy Fucked
    Best Videos
    By clicking the content you will also see an ad. AD
    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
    201.2K views
    Small Dick Sissy Playing with a Fuck Machine - Sissy Captions
    05:38
    Small Dick Sissy Playing with a Fuck Machine - Sissy Captions
    JenniferStarTS
    16.9K views
    fuck machine handsfree cum 20240421
    06:48
    fuck machine handsfree cum 20240421
    WDJRYBB
    100.5K views
    Fuck You Ass with a Fuck Machine - Sissy Training 003
    05:20
    Fuck You Ass with a Fuck Machine - Sissy Training 003
    JenniferStarTS
    586 views
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    10:16
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    Jessica Bloom
    72.8K views
    Fucking My Ass with a Fuck Machine - Sissy Slut
    00:45
    Fucking My Ass with a Fuck Machine - Sissy Slut
    JenniferStarTS
    1K views
    blonde femboy fuck machine sissy training!
    13:20
    blonde femboy fuck machine sissy training!
    Cassie Coyote
    96K views
    Beautiful Big Ass Tranny MILF in Fishnet Enjoying Her Fuck Machine - Sissy Slut Big Ass
    01:24
    Beautiful Big Ass Tranny MILF in Fishnet Enjoying Her Fuck Machine - Sissy Slut Big Ass
    JenniferStarTS
    1.3K views
    Lena Vesper's Milking & Gooning Session
    08:12
    Lena Vesper's Milking & Gooning Session
    Snake_0rgy
    199.2K views
    Fuck Machine - Sissy Tranny MILF
    00:48
    Fuck Machine - Sissy Tranny MILF
    JenniferStarTS
    1.3K views
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    11:37
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    956.6K views
    Destroying My Ass with a Fuck Machine - Sissy Whore
    07:28
    Destroying My Ass with a Fuck Machine - Sissy Whore
    JenniferStarTS
    677 views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Fucking My Big Fat Ass with a Fuck Machine - Sissy Slut
    02:30
    Fucking My Big Fat Ass with a Fuck Machine - Sissy Slut
    JenniferStarTS
    961 views
    Sex Chair
    03:06
    Sex Chair
    XiangYan
    65.6K views
    Destroying My Ass with a Fuck Machine - Sissy Trainning
    07:42
    Destroying My Ass with a Fuck Machine - Sissy Trainning
    JenniferStarTS
    586 views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Throatfucking Machine Sissy Rough
    26:03
    Throatfucking Machine Sissy Rough
    Sissycdslc
    38.2K 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
    34.8K views
    Fucking Machine Sissy Anal Orgasm And Cum Play
    09:05
    Fucking Machine Sissy Anal Orgasm And Cum Play
    Jessica Bloom
    10.6K views

    Relevant Short videos

    Fuck You Ass with a Fuck Machine - Sissy Training 003
    Fuck You Ass with a Fuck Machine - Sissy Training 003
    JenniferStarTS
    1K views
    Destroying My Ass with a Fuck Machine - Sissy Trainning
    Destroying My Ass with a Fuck Machine - Sissy Trainning
    JenniferStarTS
    392 views
    Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy
    Sissy Motivation 4: Sex Machine Sissy Trainer, Sissy Instruction, Sissification, Femboy
    Margo-apollo
    892 views
    Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.
    Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.
    Traviezisha
    143 views
    sissy fuck machine
    sissy fuck machine
    Jade Sissy
    12.2K views
    Satanic sissy gets fuck machine
    Satanic sissy gets fuck machine
    Chrissie Satanas Whiteboi
    4.7K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.
    02:12
    Submissive Sissy Slave Tied and Fucked by Machine. Sissy Ass Drilled by Machine.
    Traviezisha
    715 views
    Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times
    10:08
    Fuck Machine Sissygasm Milking Jessica Bloom Cums Multiple Times
    Jessica Bloom
    158.7K views
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    05:56
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    Elvi Lynx
    64.6K views
    this fuck machine goes so deep omg 😵
    01:10
    this fuck machine goes so deep omg 😵
    amyy_babyy_x
    281.9K views
    Trans girl Jenni wants to be your girlfriend.  Models her lingerie for you.  Fuck machine play time
    09:07
    Trans girl Jenni wants to be your girlfriend. Models her lingerie for you. Fuck machine play time
    Jenni Wallace
    124K views
    Fuck machine anal orgasm
    03:04
    Fuck machine anal orgasm
    Sissy-boys
    106.5K views
    Chastity cage and fuck machine makes perfect cum
    14:09
    Chastity cage and fuck machine makes perfect cum
    yourprettykate
    19.8K views
    Sissy gets fucked by BBC in her sexy pink lingerie 🙇🏻‍♀️
    14:57
    Sissy gets fucked by BBC in her sexy pink lingerie 🙇🏻‍♀️
    Sissy Amina
    45.7K views
    Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
    01:30
    Cute Fat Ass Trans First Time Fuck-machine and Self Footjob
    Melodyfluffington
    91.8K views
    I was tied to the bed and masturbated mercilessly without using my hands I think I like to be tied up I'm more interested in BDSM
    16:23
    I was tied to the bed and masturbated mercilessly without using my hands I think I like to be tied up I'm more interested in BDSM
    Usaberilx
    47.7K views
    Fuck Machine
    00:45
    Fuck Machine
    boobyb0y
    38.8K 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
    72.3K views
    Sissy slut spitroast training with my fuck machine and dildos
    03:05
    Sissy slut spitroast training with my fuck machine and dildos
    trixied93
    6.3K views
    Missionary
    02:12
    Missionary
    Twistedrama
    9.3K views
    Fuck Machine - Anal disassembly
    09:12
    Fuck Machine - Anal disassembly
    LaurelineTV
    73.5K views
    Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
    01:13
    Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - full video on LayneLovee Manyvids
    Layne Love
    179.8K views
    Sissy Fuck Machine Training
    07:39
    Sissy Fuck Machine Training
    Mistress Jodie May
    81K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Xmas fun with fuck machine
    08:29
    Xmas fun with fuck machine
    yourprettykate
    5.7K views
    Anal machine creamy hard assfuck.
    23:50
    Anal machine creamy hard assfuck.
    Bootyanal
    183.7K views
    Chastity cage and fuck machine are best present
    07:50
    Chastity cage and fuck machine are best present
    yourprettykate
    4.5K views
    sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!
    09:09
    sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!
    yourprettykate
    35.7K views
    Tgirl moaning and fuck machine
    03:19
    Tgirl moaning and fuck machine
    Letany Ponny
    151.1K views
    Fucking machine and big toys makes me squirt and cum
    24:48
    Fucking machine and big toys makes me squirt and cum
    Muckyfun
    99.8K views
    Fuck Machine Cam Session - Latex Hood, Bra, Stockings, Suspenders, Chasity, Ball Gagged
    07:46
    Fuck Machine Cam Session - Latex Hood, Bra, Stockings, Suspenders, Chasity, Ball Gagged
    JessicaXD
    4.3K views
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    23:36
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    Sissy Candy
    32.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Fuck Machine Sissy

    • Sissy Fuck Machine
    • Femboy Sissification
    • Sissygasm
    • Sissyboy-5
    • Trans High Heels XXX
    • Femdom Extreme
    • Nasty Tranny Cum Whore
    • Your-Sissyslut
    • Crossdresser Get Fucked so Hard
    • Sissy-Slut-Jenny
    • Dirtysissykitty
    • Crossdressing Bondage Slut
    • Sissies in Prison
    • Feminization BDSM
    • All My Roommates Love 10 Part 1
    • Intense Faggot Verbal Humiliation Tgirl
    • Submissive 039 Chastity
    • Ftm Beast Boy
    • Degrading Sissy
    • Monster Cock Rough Anal Shemale
    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