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
    • Black
    • Big Cock
    • 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
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • 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

    Chastity Sissy Instructions Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    08:23
    Chastity Sissy Anal Training Jessica Bloom Anal Instructions
    linktree
    43.4K 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
    39.9K views
    Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
    07:28
    Sissy Jessica Bloom Teaches You How To Suck Cock And Swallow Cum
    linktree
    59.8K views
    Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
    07:34
    Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!
    Holly unt
    30K views
    POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass
    21:40
    POV/JOI: Your trans friend helps you jerk off to the alternative and original green light, red light game, by pulling dice out of her ass
    Vane03_siss
    19.8K views
    Feminization Training - Show This To Your Wife
    07:58
    Feminization Training - Show This To Your Wife
    Holy
    68.8K views
    Snowbunny Slave Halloween Costume
    11:08
    Snowbunny Slave Halloween Costume
    Natalie Napoli
    8.3K views
    Sissy Holy - Chastity Masturbation Instructions - how I play with myself
    07:52
    Sissy Holy - Chastity Masturbation Instructions - how I play with myself
    Holy
    42.1K views
    JOI: Sissy Nurse in Chastity Teaches You How to Become a Good Sissy
    11:43
    JOI: Sissy Nurse in Chastity Teaches You How to Become a Good Sissy
    Vane03_siss
    3.9K views
    Sissy in miniskirt and chastity with big dildo outdoor
    02:35
    Sissy in miniskirt and chastity with big dildo outdoor
    dutchsissywhore
    6.6K views
    Sissy Anal Training Instructions - Fuck your Ass with Me FULL VID on LayneLovee Manyvids
    01:24
    Sissy Anal Training Instructions - Fuck your Ass with Me FULL VID on LayneLovee Manyvids
    Layne Love
    26.2K views
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    11:51
    Mommy Holy - JOI - Lock you in Chastity then Anal Milking
    Holy
    12.1K views
    Mommy Holy - The Workload - a JOI story
    50:35
    Mommy Holy - The Workload - a JOI story
    Holy
    14.4K views
    Mommy Holy - JOI CEI - The Juices Are Your Reward
    08:58
    Mommy Holy - JOI CEI - The Juices Are Your Reward
    Holy
    11.7K views
    Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay
    10:00
    Femdom Dildo Encouragement Suck my Dick Sissy POV Rollplay
    linktree
    22.6K views
    Mommy Holy - Feminization - Time For Your First Chastity
    13:02
    Mommy Holy - Feminization - Time For Your First Chastity
    Holy
    8.2K views
    Today is Chastity Day! This won't be fun for you! But for me! JOI CEI
    01:18
    Today is Chastity Day! This won't be fun for you! But for me! JOI CEI
    Mydirtyhobby
    9.8K views
    Mommy Holy - JOI - Time To Take Your Chastity Off
    04:42
    Mommy Holy - JOI - Time To Take Your Chastity Off
    Holy
    6.1K views
    Bday Surprise - Feminized & Fucked by Your Sissy Roommate FULL VID on LayneLovee Manyvids
    01:14
    Bday Surprise - Feminized & Fucked by Your Sissy Roommate FULL VID on LayneLovee Manyvids
    Layne Love
    7.1K views
    Mommy Holy - It's Ok The Doctor Said So - a JOI story with a little CEI
    06:53
    Mommy Holy - It's Ok The Doctor Said So - a JOI story with a little CEI
    Holy
    5.8K views
    Sissy Entertains Her Cock Hungry Cunt in a Hotel Room
    10:40
    Sissy Entertains Her Cock Hungry Cunt in a Hotel Room
    Sonechka25
    3.7K views
    Mommy Holy - JOI - Teachers Pet Gets A Double
    08:21
    Mommy Holy - JOI - Teachers Pet Gets A Double
    Holy
    7.5K views
    You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN
    00:43
    You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN
    Mydirtyhobby
    16.5K views
    a simple rope harness tutorial
    10:32
    a simple rope harness tutorial
    Kittykisses96
    6.3K views
    Mtf Transformation: Naked Grwm (makeup & Dress)
    02:12
    Mtf Transformation: Naked Grwm (makeup & Dress)
    FapHouse
    just added
    I Am Wearing a Chastity Device and Wearing a Miniskirt, Carrying Out the Instructions of the Viewer...
    11:12
    I Am Wearing a Chastity Device and Wearing a Miniskirt, Carrying Out the Instructions of the Viewer...
    KANAe
    5.9K views
    Sissy Instructions
    04:04
    Sissy Instructions
    FapHouse
    726 views
    Flat Chastity Sissy
    21:45
    Flat Chastity Sissy
    Juahlovely
    114.5K views
    Chastity Sissy Machine Ballbusting
    01:25
    Chastity Sissy Machine Ballbusting
    suckyoudry76
    25.6K views
    chastity sissy slut vibrator cum
    08:16
    chastity sissy slut vibrator cum
    Juahlovely
    158.1K 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
    201.2K 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
    74.7K 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
    3.6K views
    super flat chastity sissy anal dildo squirt
    13:39
    super flat chastity sissy anal dildo squirt
    Juahlovely
    31.6K 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
    60.6K views
    chastity sissy splashing on the floor
    12:25
    chastity sissy splashing on the floor
    Juahlovely
    19.3K views
    Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm
    05:14
    Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm
    Jessica Bloom
    28.1K 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
    11.4K 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
    24.4K views
    chastity sissy self bondage exhibitionism fantasy
    09:26
    chastity sissy self bondage exhibitionism fantasy
    Juahlovely
    15K views
    Chastity Sissy training her pussy with BBC dildo
    02:05
    Chastity Sissy training her pussy with BBC dildo
    M MommyOwnsMe
    9.2K views
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    10:06
    Chastity Sissy Slut Anal Training Dice Game Jessica Bloom
    Jessica Bloom
    7.2K views
    Video Arcade Chastity Sissy
    01:27
    Video Arcade Chastity Sissy
    SissyMindy10
    4.1K 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
    8.6K views
    Chastity Sissy Sucks Daddy's Cock
    00:59
    Chastity Sissy Sucks Daddy's Cock
    72.9K 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
    linktree
    11.5K views
    Chastity sissy Raine playing with HUGE DILDO
    06:33
    Chastity sissy Raine playing with HUGE DILDO
    Rainbow Femboy
    46.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Chastity Sissy Instructions

    • Sissy Chastity Fucked BBC
    • Submissive Transvestite Training
    • Sissification Process
    • Caught Wearing Sisters Clothes
    • Fuck My Ass Please Dirty Talk
    • Turning Him Into a Complete Bitch
    • Tied Trans Drilled Hard BDSM Anal
    • The Sissy's Future
    • Instruction for Crossdressers
    • Crossdresser Sub Serves Master
    • Cock Under Dress
    • Caged Sissies
    • Slut Trainer
    • Cuckold Clean up
    • Secret Sissyboy
    • Out of Control
    • Sissypink Boy
    • Cum in Cage
    • Wife Encourages Husband Bi Sex
    • Dildo Instructions
    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