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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Chastity Butt Plug Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Chastity
    Plug
    Butt
    Sissy Chastity
    Chastity Sissy
    Sissy Plug
    Chastity Plug
    Sissy Butt
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Best Videos
    By clicking the content you will also see an ad. AD
    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
    sissy outdoor in chastity, butt plug and tits clamps
    01:26
    sissy outdoor in chastity, butt plug and tits clamps
    2.9K views
    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
    Sissy Chastity and Butt Plug Play
    01:36
    Sissy Chastity and Butt Plug Play
    robbietest
    22.7K 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
    Sissy chastity with a huge and buttplug deep in your ass
    03:31
    Sissy chastity with a huge and buttplug deep in your ass
    Gihcrossdresser
    12.1K 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
    68.5K 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
    16.1K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    76.5K views
    Angel Reina Hanno Stimulates Cream with Golden Butt Plug
    01:07
    Angel Reina Hanno Stimulates Cream with Golden Butt Plug
    Reina Hanno
    2.8K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    120.7K views
    SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG
    05:15
    SISSY SLUT SHOWS OFF AND PUSHES OUT BUTT PLUG
    SlimsissyJessica
    50.5K views
    Down the Sissy Rabbit Hole - My Story
    00:44
    Down the Sissy Rabbit Hole - My Story
    Sissy Joyce
    13.6K views
    Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
    10:30
    Femboy Sissy in Chastity, Anal Gape by Fuckmachine Dildo and Pighole Butt Plug
    G8pess
    15K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    112.8K views
    SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo
    10:55
    SissyCDMish - qos sissy camwhore with chastity cage, butt plug and dildo
    SissyCDMish
    8.6K views
    fufu clip sissy anal dildo squirt
    05:56
    fufu clip sissy anal dildo squirt
    Juahlovely
    60.6K views
    stretching my lil ass more with an inflatable butt plug once again
    15:19
    stretching my lil ass more with an inflatable butt plug once again
    13.6K views
    Flat Chastity Sissy
    21:45
    Flat Chastity Sissy
    Juahlovely
    110.4K views
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    18:40
    Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
    SissyHousewife
    5.6K views
    Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce
    17:39
    Chastity Guide : A review of all metal chastity cages!! - By Sissy Joyce
    Sissy Joyce
    135.7K views
    Tiny dick sissy pissing like a slave in chastity cage and butt plug try to scape chastity cage later
    08:13
    Tiny dick sissy pissing like a slave in chastity cage and butt plug try to scape chastity cage later
    SissySimran
    116.5K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    265.7K views
    Sissy Maid light up Butt Plug
    05:21
    Sissy Maid light up Butt Plug
    Sissy Skylar
    3K views
    This Foot Is so Cute. I Want It My Balls.
    02:51
    This Foot Is so Cute. I Want It My Balls.
    XiangYan
    68.7K views
    Sissy school in chastity and butt plug
    02:12
    Sissy school in chastity and butt plug
    Sexysissysimone
    807 views
    Cute sissy chastity cage try on - 6 different cages for you FULL VID on LayneLovee Manyvids
    01:39
    Cute sissy chastity cage try on - 6 different cages for you FULL VID on LayneLovee Manyvids
    Layne Love
    64.4K views
    using a vibrator on my clit cage and butt plug and flogging myself
    03:46
    using a vibrator on my clit cage and butt plug and flogging myself
    Emma Huntcock
    3.3K views
    Negative Cage hardcore Cumload
    02:12
    Negative Cage hardcore Cumload
    boobyb0y
    106.6K views
    stretching my lil ass with an inflatable butt plug once again
    07:46
    stretching my lil ass with an inflatable butt plug once again
    4.2K views
    chastity sissy slut vibrator cum
    08:16
    chastity sissy slut vibrator cum
    Juahlovely
    154.2K views
    Sissy Femboy Butt Plug Gape My Buckethole
    01:07
    Sissy Femboy Butt Plug Gape My Buckethole
    G8pess
    2.3K 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
    304.9K views
    Sissy girl loves her new inflatable butt plug
    03:25
    Sissy girl loves her new inflatable butt plug
    Lauren green
    815 views
    Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
    07:37
    Inverted Chastity Off, Itty Bitty Clitty Gets Sounded, Pushed Back in & Locked up Again!
    MJ
    201.2K views
    Trans Women Use Dildo, Butt Plug, Vibrator, Chastity and More
    11:18
    Trans Women Use Dildo, Butt Plug, Vibrator, Chastity and More
    Bailey Wilde
    4.8K 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
    Sissy in chastity playing hiding the butt plug
    01:35
    Sissy in chastity playing hiding the butt plug
    TamaraTv
    2K views
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    78.5K views
    Sissy Nikki - Playing with my butt plug in chastity
    01:42
    Sissy Nikki - Playing with my butt plug in chastity
    nikki_x
    3.1K views
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    07:20
    The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
    Sonechka25
    33.2K views
    AB2509 Locked three months Cute femboy cum in flashlight with e-plug
    02:54
    AB2509 Locked three months Cute femboy cum in flashlight with e-plug
    Abby Kitty
    33.7K views
    SissyJoyce Sissygasm
    01:25
    SissyJoyce Sissygasm
    Sissy Joyce
    58.1K views
    Almost Handsfree Tiny-clit, Butt-plugged Sissygasm
    05:39
    Almost Handsfree Tiny-clit, Butt-plugged Sissygasm
    Cindy Belfast
    25.4K views
    Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
    05:13
    Mistress Gives Her Caged Sissy a little Spanking – Obedience and Discipline Lesson
    Lucy Dee
    8.4K views
    Extremly deep anal fuck throught Tunnel Plug open Hole gape
    09:48
    Extremly deep anal fuck throught Tunnel Plug open Hole gape
    Davine
    128.9K views
    Urethral Tube Stimulation with Chastity Cage
    07:00
    Urethral Tube Stimulation with Chastity Cage
    Reina Hanno
    42.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Chastity Butt Plug

    • Sissy Crossdresser Anal Fucking Chastity
    • Vibrating Butt Plug
    • Caged and Plugged
    • Shemale Sissygasm
    • Trans Prostate Orgasm
    • Moaning Femboy Cums With Cock in Ass
    • Femdom Milking Machine Torture
    • Cute Trap Hands Free Cum
    • Public Buttplug
    • Sissy Chastity Anal
    • Squirting Dildo
    • New Cumpilation Best Handsfree Orgasms
    • Ladyboy Prostate Orgasm
    • Huge Cumshot Straight to the Mouth
    • Ball Gag
    • What Is a Sissygasm
    • Extreme Insertion
    • Ladyboys Cumming While Fucked
    • Tranny Electro Stim
    • Transboy Ftm Big Clit Masturbation

    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