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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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 Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the straight section?
    Sissy
    Chastity
    Chastity Sissy
    Sissy Chastity Bondage
    Sissy Chastity Femdom
    Sissy Chastity Anal
    Sissy Chastity Fucked
    Sissy Cumming Chastity
    Sissy Cuckold Chastity
    Sissies in Chastity
    Sissy Chastity Cage
    Sissy Maid Chastity
    Sissy Chastity Humiliation
    Sissy Chastity Slave
    Sissy Chastity Pegged
    Sissy Chastity BBC
    Sissy Chastity Training
    Sissy Permanent Chastity
    Sissy Chastity Slut
    Sissy Chastity Orgasm
    Best Videos
    By clicking the content you will also see an ad. AD
    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
    65.1K views
    Locked in Chastity and Using a Vibrator to Make My Girldick Cum
    06:16
    Locked in Chastity and Using a Vibrator to Make My Girldick Cum
    Gray Perrier
    2.1K 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
    198.9K views
    Sissy Bride in Chastity
    05:48
    Sissy Bride in Chastity
    Pure Ts
    3K 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
    165.1K views
    Chastity sissy instructions
    06:15
    Chastity sissy instructions
    217.1K 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
    172.8K views
    Sissy Chastity Maid Service Training With Ria Bentley
    07:07
    Sissy Chastity Maid Service Training With Ria Bentley
    Ria_Bentley
    35.5K views
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    05:11
    Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana
    Jessica Bloom
    273.5K views
    How I've made my boyfriend into a anal slut
    04:39
    How I've made my boyfriend into a anal slut
    Trinit Noir
    55K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    264.5K views
    Fucking my CAGED little tranny toy and CUMMING on her ass
    03:59
    Fucking my CAGED little tranny toy and CUMMING on her ass
    Freya Frostnymph
    108.3K views
    Sissy Dressup Party with Sasha De sade Goes wrong
    01:10
    Sissy Dressup Party with Sasha De sade Goes wrong
    Sissy Joyce
    98.9K views
    Skitty&M&L in Our first fun Together
    21:22
    Skitty&M&L in Our first fun Together
    Skitty
    83.1K 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
    134.3K views
    Redhead Latina Twerk Ass While Playing with Your Thong
    04:39
    Redhead Latina Twerk Ass While Playing with Your Thong
    Tomas Styl
    just added
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    05:27
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    ActorFab
    221.3K views
    Fun Trans Cheerleader Plays with Her Soft Cock
    08:12
    Fun Trans Cheerleader Plays with Her Soft Cock
    Tomas Styl
    just added
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    680.5K views
    Jasmine is practicing her anal for Mistress
    03:13
    Jasmine is practicing her anal for Mistress
    Jasmine904x
    just added

    Relevant Short videos

    Sissy Chastity Cage Hardcore Anal Playplay
    Sissy Chastity Cage Hardcore Anal Playplay
    Lexi Faith
    3.3K views
    sissy chastity cumshot
    sissy chastity cumshot
    boobyb0y
    3.9K views
    Asian Sissy Chastity and Pantyhose Outside
    Asian Sissy Chastity and Pantyhose Outside
    CuteAsianSissy
    1.9K views
    Quick Sissy Chastity Tease
    Quick Sissy Chastity Tease
    Sophie Kay
    2.1K views
    Sissy chastity maid
    Sissy chastity maid
    Sissyboy-5
    1.7K views
    Asian Sissy Chastity Anal Cumshot
    Asian Sissy Chastity Anal Cumshot
    CuteAsianSissy
    605 views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    118.9K views
    Sissy Locked and Loaded with Cum
    06:40
    Sissy Locked and Loaded with Cum
    Emily Meadows
    just added
    mistress cages sissy
    12:29
    mistress cages sissy
    938K views
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    06:12
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    Ria_Bentley
    just added
    sissy clitty chastity
    07:26
    sissy clitty chastity
    522.9K views
    Sissy Shelby Kiss's New Year's Resolutions for 2026
    03:15
    Sissy Shelby Kiss's New Year's Resolutions for 2026
    Sissy Shelby Kiss
    just added
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    73K views
    Sissy maid, wearing a satin underbust corset, bra, latex stockings and suspenders underneath gets very frustrated in chastity
    05:24
    Sissy maid, wearing a satin underbust corset, bra, latex stockings and suspenders underneath gets very frustrated in chastity
    JessicaXD
    just added
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    76.7K views
    sissy girl jessie sissy adventures become a slutty student practicing for sex ed at home
    04:19
    sissy girl jessie sissy adventures become a slutty student practicing for sex ed at home
    jessiesissyadventures
    just added
    Sissy chastity training
    08:23
    Sissy chastity training
    224.7K views
    Big ass tranny taking it like a pro and gets creampie
    06:28
    Big ass tranny taking it like a pro and gets creampie
    Trinit Noir
    3K views
    Flat Chastity Sissy
    21:45
    Flat Chastity Sissy
    Juahlovely
    108.9K views
    sam_cdsissy sissy crossdresser cums on cam
    24:49
    sam_cdsissy sissy crossdresser cums on cam
    S Sam_cdsissy
    2K views
    Sissys in chastity
    03:40
    Sissys in chastity
    765.1K views
    I sucked his cook so good that he fucked me
    05:17
    I sucked his cook so good that he fucked me
    Trinit Noir
    196.4K views
    Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
    06:23
    Jessica Bloom Dominates Her new Pig Fuck Toy Jenby Doll
    Jessica Bloom
    233.5K views
    Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
    08:25
    Pink Satin Sissy Maid Gets Fucked by Her Fucking Machine and Plays with Her Sex Toy Doll
    Sissy Candy
    just added
    2 Sissies 1 Chastity Cage
    01:09
    2 Sissies 1 Chastity Cage
    Sissy Joyce
    262.1K views
    caged sissy slut ride big dildo in public toilet jessie sissy adventures
    02:26
    caged sissy slut ride big dildo in public toilet jessie sissy adventures
    jessiesissyadventures
    just added
    Subby's Secret... Tranny with chastity belt and gag while shopping!!
    01:15
    Subby's Secret... Tranny with chastity belt and gag while shopping!!
    Allmylinks
    78.4K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    23.2K views
    Transgender sissy joyce in chastity shows hormone progress
    05:16
    Transgender sissy joyce in chastity shows hormone progress
    Sissy Joyce
    83.1K views
    It's Always Nice to Have Friends! Let's Dance!
    02:47
    It's Always Nice to Have Friends! Let's Dance!
    violet_bisex
    just added
    Caught in the electric penis cage and piss me on my seam stockings with boots
    10:00
    Caught in the electric penis cage and piss me on my seam stockings with boots
    Loreleyadd
    134K views
    Sissy in Eunuch Chastity Device Getting Her Ass Drilled by Machine and Shaking Sissygasm with No Cum
    03:32
    Sissy in Eunuch Chastity Device Getting Her Ass Drilled by Machine and Shaking Sissygasm with No Cum
    Traviezisha
    just added
    Urethral Tube Stimulation with Chastity Cage
    07:00
    Urethral Tube Stimulation with Chastity Cage
    Reina Hanno
    39.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 55
    • Next

    Searches Related to Sissy Chastity

    • Chastity Sissy
    • Caged Sissies
    • First Sissygasm
    • Chastity Sissy Fucking Machine
    • Secret Sissyboy
    • Feminized and Fucked
    • Chasity Cage
    • Self Bondage
    • Sissy-Boys
    • Femdom Feminization
    • White Femboys Are so Submissive
    • Crossdressers in Pretty Dresses
    • Sissy-Virgin
    • Crossdresser Humiliation
    • Shemale Tied up
    • Caged Cum
    • Sissys Get Blacked
    • Prostate Orgasm Tutorial
    • Sissy Cuckold Chastity
    • Feminine Trap

    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