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

    Sissy Fucked Chastity Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Chastity
    Fuck
    Sissy Chastity
    Sissy Fucked
    Chastity Sissy
    Chastity Fuck
    Fuck Sissy
    Sissy Chastity Fucked BBC
    Sissy Chastity Fucked Raw
    Sissy Chastity Fucked by Bull
    Sissy Chastity Brainwashed and Fucked
    Femdom Sissy Chastity Machine Fucked
    Sissy in Chastity Fucked by BBC
    Sissy Crossdresser
    Sissy Training
    Femboy Fucked
    Crossdresser Fucked
    Bbc Sissy
    Sissy Feminization
    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 fucked with some monster dildos
    42:25
    Sissy fucked with some monster dildos
    Niceguy_1991
    319.5K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    chastity sissy fucked by big cocked daddy
    02:20
    chastity sissy fucked by big cocked daddy
    91.9K views
    Sissy Dressup Party with Sasha De sade Goes wrong
    01:10
    Sissy Dressup Party with Sasha De sade Goes wrong
    Sissy Joyce
    109.8K views
    Good sissy fucked by machine
    05:21
    Good sissy fucked by machine
    Lockedupunicorn
    5.4K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Chastity Sissy Fucked by Fucking Machine
    05:41
    Chastity Sissy Fucked by Fucking Machine
    SissyStacey14
    1.6K views
    Cute tranny fucked in tiny chastity bareback
    02:11
    Cute tranny fucked in tiny chastity bareback
    Trinit Noir
    39.7K views
    Sissy fucked by bbc machine, rnd guy fucks me soo good
    25:24
    Sissy fucked by bbc machine, rnd guy fucks me soo good
    Niceguy_1991
    21K 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 fucked by fuck machine cumming
    06:36
    Sissy fucked by fuck machine cumming
    Crystal Phoenix
    5.6K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Caged Sissy Fucked By Huge BBC Dildo
    01:49
    Caged Sissy Fucked By Huge BBC Dildo
    FEMBOIIxFRANKII
    1.9K views
    Down the Sissy Rabbit Hole - My Story
    00:44
    Down the Sissy Rabbit Hole - My Story
    Sissy Joyce
    13.6K views
    Sissy Fucked in Chastity by a Machine
    06:55
    Sissy Fucked in Chastity by a Machine
    Ramona_Gold
    2.1K 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
    70.6K views
    Chastity Sissy fucked by Machine
    01:15
    Chastity Sissy fucked by Machine
    Anaconda85
    4K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    112.8K views
    Sissy fucked hard while in chastity
    06:00
    Sissy fucked hard while in chastity
    2.3K 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
    Caged Sissy Fucked By a Dildo Fuck Machine
    02:00
    Caged Sissy Fucked By a Dildo Fuck Machine
    FEMBOIIxFRANKII
    1.1K 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
    135.7K views
    Sissy fucked by BBC with Fuckmachine
    01:20
    Sissy fucked by BBC with Fuckmachine
    Anaconda85
    753 views
    Sissy clitty leaking in its flat chastity cage from bareback anal pleasure
    09:30
    Sissy clitty leaking in its flat chastity cage from bareback anal pleasure
    Traviezisha
    107.2K views
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    05:45
    I fuck my roommate and fills my butthole full of cum while i'm in chastity
    missangell_
    667K 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
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    09:05
    TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED
    Adam Castle
    365K views
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    01:19
    TGirl in Chastiy has Anal Orgasm Sissygasm🏳️‍⚧️
    Princesszoey
    78.2K views
    2032 - the Bwno Future
    15:06
    2032 - the Bwno Future
    ChristineWest120
    112.7K views
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    78.5K views
    Video editing session turns into a kinky bi and trans foursome orgy
    40:50
    Video editing session turns into a kinky bi and trans foursome orgy
    Spike Essex
    1.2M views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    Sissy Merve Rose Chastity Belt Tattoo Blonde Sexy Tgirl Femboy Body Stockings BBC Fucked Hard Doggy Style Catgirl Tranny Trans
    06:00
    Sissy Merve Rose Chastity Belt Tattoo Blonde Sexy Tgirl Femboy Body Stockings BBC Fucked Hard Doggy Style Catgirl Tranny Trans
    TSMerve
    124.8K views
    sissygasm caged Compilation
    03:17
    sissygasm caged Compilation
    boobyb0y
    267.3K views
    POV: You are fucking me!!
    07:02
    POV: You are fucking me!!
    Sexy Luke
    27.7K 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
    Cumming Inside A Femboy
    02:36
    Cumming Inside A Femboy
    Cassie Coyote
    600.8K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.9M views
    Fisting Double Sissygasm Cumshots
    01:38
    Fisting Double Sissygasm Cumshots
    Lola Spais
    156.4K views
    Sissy in flat chastity cage opening her legs and ass for his male to fuck her bareback
    10:56
    Sissy in flat chastity cage opening her legs and ass for his male to fuck her bareback
    Traviezisha
    130.4K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    27.1K views
    Bound sissy in chastity gets BBC
    07:46
    Bound sissy in chastity gets BBC
    944.5K 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
    60.1K views
    Tranny with chastity cage fucked deep
    02:28
    Tranny with chastity cage fucked deep
    LittleVixenSlut
    24.1K views
    Sissy fucked hard in chastity
    01:39
    Sissy fucked hard in chastity
    3.3K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Fucked Chastity

    • Sissy Crossdresser Anal Fucking Chastity
    • Femboy Cum While Fucked
    • Traps Femboys and Sissys
    • Bound Sissy in Chastity Gets BBC
    • Femboy Fucked Hard
    • Fuck My Ass Please Dirty Talk
    • Femdom With Crossdresser
    • Feminized Husband Turned Into Slave
    • Chastity Sissy Sucks Daddy Cock
    • What Does a Sissygasm Feel Like
    • Sissy-Virgin
    • Submissive Trans
    • Anal Machine Chastity Sissy
    • Two Sissies Crossdresser Bondage 69
    • Beautiful Shemale Can T Stop Cumming
    • Secret Sissyboy
    • Bdsm Tranny Slut
    • Crossdressing Boy to Girl
    • Extrem Crossdressers
    • Femdom Feminization

    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