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

    Chastity 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
    Chastity
    Sissy Chastity
    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
    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
    174.4K 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
    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 instructions
    06:15
    Chastity sissy instructions
    217.1K views
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    78.5K 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
    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
    Chastity Sissy Butt-Chugging Beer on Her Top Bunk Next to the Open Window
    08:13
    Chastity Sissy Butt-Chugging Beer on Her Top Bunk Next to the Open Window
    Traviezisha
    3.3K 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
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    08:23
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    Jessica Bloom
    42.6K 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 big cocked daddy
    02:20
    chastity sissy fucked by big cocked daddy
    91.9K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    76.5K views
    super flat chastity sissy anal dildo squirt
    13:39
    super flat chastity sissy anal dildo squirt
    Juahlovely
    30.7K views
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    11:37
    Tranny Babe in Chasity Cage Gets Fucked by large Dildo
    944.2K views
    Chastity Sissy Anal Orgasms And Licking Cum of Feet  Jessica Bloom and Femdom Polieana
    10:23
    Chastity Sissy Anal Orgasms And Licking Cum of Feet Jessica Bloom and Femdom Polieana
    Jessica Bloom
    59.3K views
    Sissy Dressup Party with Sasha De sade Goes wrong
    01:10
    Sissy Dressup Party with Sasha De sade Goes wrong
    Sissy Joyce
    106.2K views
    chastity sissy splashing on the floor
    12:25
    chastity sissy splashing on the floor
    Juahlovely
    18.9K 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
    Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm
    05:14
    Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm
    Jessica Bloom
    27.6K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    265.7K 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
    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
    Chastity Sissy Dildo Riding Anal Orgasms Using Cum As Lube - Jessica Bloom
    10:20
    Chastity Sissy Dildo Riding Anal Orgasms Using Cum As Lube - Jessica Bloom
    Jessica Bloom
    23.9K 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
    Chastity Sissy training her pussy with BBC dildo
    02:05
    Chastity Sissy training her pussy with BBC dildo
    M MommyOwnsMe
    8.9K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    120.7K views
    chastity sissy self bondage exhibitionism fantasy
    09:26
    chastity sissy self bondage exhibitionism fantasy
    Juahlovely
    14.6K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    112.8K views
    Chastity Sissy Throat Training And Plapping Orgasm - Huge Cum Squirt And Swallow Jessica Blooom
    10:45
    Chastity Sissy Throat Training And Plapping Orgasm - Huge Cum Squirt And Swallow Jessica Blooom
    Jessica Bloom
    8.3K views
    Cute tranny fucked in tiny chastity bareback
    02:11
    Cute tranny fucked in tiny chastity bareback
    Trinit Noir
    39.7K views
    Video Arcade Chastity Sissy
    01:27
    Video Arcade Chastity Sissy
    SissyMindy10
    4K views
    fufu clip sissy anal dildo squirt
    05:56
    fufu clip sissy anal dildo squirt
    Juahlovely
    60.6K views
    Chastity Sissy Sucks Daddy's Cock
    00:59
    Chastity Sissy Sucks Daddy's Cock
    72.7K views
    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
    136.4K views
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    10:06
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    Jessica Bloom
    7K views
    chastity sissy slut vibrator cum
    08:16
    chastity sissy slut vibrator cum
    Juahlovely
    154.2K views
    Chastity Sissy Cumslut Trains Her Asshole And Swallows Her Own Cum, Multiple Prostate Orgasms
    05:50
    Chastity Sissy Cumslut Trains Her Asshole And Swallows Her Own Cum, Multiple Prostate Orgasms
    Jessica Bloom
    11.2K views
    Flat Chastity Sissy
    21:45
    Flat Chastity Sissy
    Juahlovely
    110.4K views
    Chastity sissy Raine playing with HUGE DILDO
    06:33
    Chastity sissy Raine playing with HUGE DILDO
    Rainbow Femboy
    45.7K views
    Chasity cage
    03:55
    Chasity cage
    NikkyTrav
    150K views
    Chastity Sissy Riding a BBC
    04:17
    Chastity Sissy Riding a BBC
    FEMBOIIxFRANKII
    5.2K views
    Negative Cage hardcore Cumload
    02:12
    Negative Cage hardcore Cumload
    boobyb0y
    106.6K views
    Sissy in Chastity,  Sissy Panties, Sissy Tattoo
    01:32
    Sissy in Chastity, Sissy Panties, Sissy Tattoo
    HO77
    17.9K views
    Urethral Tube Stimulation with Chastity Cage
    07:00
    Urethral Tube Stimulation with Chastity Cage
    Reina Hanno
    42.6K views
    Chastity Sissy Fucked by Fucking Machine
    05:41
    Chastity Sissy Fucked by Fucking Machine
    SissyStacey14
    1.6K 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
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Chastity Sissy

    • Chastity Sissy Fucking Machine
    • Caged Sissies
    • Sissy Chastity
    • Chasity Cage
    • First Sissygasm
    • Secret Sissyboy
    • Femboy Slut
    • Femdom Feminization
    • Sissification Process
    • Feminized and Fucked
    • Caged Cum
    • Sissy Cuckold Chastity
    • Trans Slave Humiliation
    • Shemale Tied up
    • Sissyslut
    • Sissy-Boys
    • Extreme Homemade
    • Real Sexy Feminine Crossdresser
    • Prostate Orgasm Tutorial
    • Crossboy With Mommy Clothes

    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