PornPorn Transgender • US
    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
    • Shemale Fucks Girl
    • Sissy
    • 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

    Anal Machine Chastity Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Anal
    Chastity
    Machine
    Sissy Chastity Anal
    Sissy Chastity
    Sissy Anal
    Chastity Sissy
    Anal Sissy
    Anal Machine
    Sissy Machine
    Anal Chastity
    Chastity Machine
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Compilation
    Best Videos
    By clicking the content you will also see an ad. AD
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    11:37
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    945.7K views
    Fed My Own Cum Strapped to Fucking Machine Chair in Chastity - Sissy Maid
    14:36
    Fed My Own Cum Strapped to Fucking Machine Chair in Chastity - Sissy Maid
    Derek6699
    73.6K 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
    176.1K 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
    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
    70.6K views
    Chastity Sissy Fucked by Fucking Machine
    05:41
    Chastity Sissy Fucked by Fucking Machine
    SissyStacey14
    1.6K views
    fuck machine handsfree cum 20240421
    06:48
    fuck machine handsfree cum 20240421
    WDJRYBB
    99.3K views
    Chastity Sissy Femboy Fucked Hard By Dildo Sex Machine
    02:43
    Chastity Sissy Femboy Fucked Hard By Dildo Sex Machine
    FEMBOIIxFRANKII
    1.6K 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
    Chastity sissy machine fucked
    00:37
    Chastity sissy machine fucked
    27.6K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    78.2K views
    Chastity Sissy Machine Fucked
    06:10
    Chastity Sissy Machine Fucked
    Dangerous
    3.6K views
    Sissy Accidentally cums while rubbing her clit in the little chastity cage
    01:41
    Sissy Accidentally cums while rubbing her clit in the little chastity cage
    KiraszaSissy
    166.9K views
    Chastity sissy taking large with remove'o'balls dildo on fucking machine full speed
    06:55
    Chastity sissy taking large with remove'o'balls dildo on fucking machine full speed
    TamaraTv
    2.9K views
    So Strongly Fucked That I Was Wet Myself
    02:44
    So Strongly Fucked That I Was Wet Myself
    XiangYan
    78.5K views
    Chastity sissy taking large dildo on fucking machine full speed
    07:00
    Chastity sissy taking large dildo on fucking machine full speed
    TamaraTv
    3.5K views
    Down the Sissy Rabbit Hole - My Story
    00:44
    Down the Sissy Rabbit Hole - My Story
    Sissy Joyce
    13.6K views
    Chastity Sissy fucked by Machine
    01:15
    Chastity Sissy fucked by Machine
    Anaconda85
    4K views
    Flat Chastity Sissy
    21:45
    Flat Chastity Sissy
    Juahlovely
    111.6K views
    Sissy gets anal machine fucked by mistress!!!
    15:21
    Sissy gets anal machine fucked by mistress!!!
    Niceguy_1991
    80K views
    Sissy Maid Struggling in new Armbinder and Steel Chastity Belt with 7" Dildo Locked inside
    10:50
    Sissy Maid Struggling in new Armbinder and Steel Chastity Belt with 7" Dildo Locked inside
    Derek6699
    62K views
    Chastity cage and fuck machine makes perfect cum
    14:09
    Chastity cage and fuck machine makes perfect cum
    yourprettykate
    15.9K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    112.8K views
    Sissy slut spitroast training with my fuck machine and dildos
    03:05
    Sissy slut spitroast training with my fuck machine and dildos
    trixied93
    5.3K views
    Sex Chair
    03:06
    Sex Chair
    XiangYan
    61.3K 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
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    02:55
    The Shortest Time! I've Ever Lasted Rubbing My Prostate with a Dildo in My Bare Feet
    XiangYan
    308.6K views
    Sissy in chastity and monster fuck machine
    07:41
    Sissy in chastity and monster fuck machine
    yourprettykate
    37.5K views
    fufu clip sissy anal dildo squirt
    05:56
    fufu clip sissy anal dildo squirt
    Juahlovely
    61.7K views
    Chastity ass pounded sissy
    03:43
    Chastity ass pounded sissy
    Lockedupunicorn
    55.6K views
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    03:09
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    Starlightfemboy
    432.5K views
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    06:54
    Stepdaddies Little Chastity Slut - Fucking Machine Cumshot
    Jessica Bloom
    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
    34.7K views
    Sissy fucked with some monster dildos
    42:25
    Sissy fucked with some monster dildos
    Niceguy_1991
    319.5K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    120.7K views
    Locked, Submissive Trans Sissy in Long Machine Play
    13:58
    Locked, Submissive Trans Sissy in Long Machine Play
    Paula Rainbow
    7.3K views
    Hands Free Sissy Orgasms Vol 5
    14:52
    Hands Free Sissy Orgasms Vol 5
    413K views
    Blonde Trans Fisting Silicone Pussy
    06:22
    Blonde Trans Fisting Silicone Pussy
    Nicole Nicolette
    10.7K views
    Cute tranny fucked in tiny chastity bareback
    02:11
    Cute tranny fucked in tiny chastity bareback
    Trinit Noir
    39.7K 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
    Milk or Tea?
    02:36
    Milk or Tea?
    XiangYan
    16.1K 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
    16" BBC vs Sissy Slut Jessica Bloom Balls Deep
    07:55
    16" BBC vs Sissy Slut Jessica Bloom Balls Deep
    Jessica Bloom
    15.2K views
    Chastity cage and fuck machine are best present
    07:50
    Chastity cage and fuck machine are best present
    yourprettykate
    4.5K 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
    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
    21.5K views
    Fucking my ass while caged and wearing heels - Summer Rayne
    03:57
    Fucking my ass while caged and wearing heels - Summer Rayne
    Summer Rayne
    67.8K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Anal Machine Chastity Sissy

    • Anal Machine
    • Sissy Chastity Sissygasm
    • Trans Prostate Orgasm
    • Destroyed My Ass
    • Fucking Machine Bondage Anal
    • Sissy Chastity Butt Plug
    • Beautiful Femboy Trap
    • Cock Cage Cum
    • Cumming Hard With Butthole Twitching
    • Traps Femboys and Sissys
    • Dildo Sissygasm
    • Extreme Insertion
    • Femboy Trap Compilation
    • Ass Destroy Slave
    • Hot Tgirl Self Facial While Analed
    • Traps Femboys and Sissies
    • Anal Machine Gaping
    • Sissy in Chastity Fucked by BBC
    • New Cumpilation Best Handsfree Orgasms
    • Urethra Torture

    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