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
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    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

    Sissy Maid In Chastity Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Chastity
    Maid
    Sissy Maid Chastity
    Sissy Maid
    Chastity Sissy
    Chastity Maid
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Sissy Blowjob
    Sissy Gangbang
    Amateur Sissy
    Sissy Cuckold
    Sissy Femdom
    Sissy Slut
    Best Videos
    By clicking the content you will also see an ad. AD
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M 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
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    697.4K views
    Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity
    29:34
    Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity
    Derek6699
    16.8K views
    Sissy Dressup Party with Sasha De sade Goes wrong
    01:10
    Sissy Dressup Party with Sasha De sade Goes wrong
    Sissy Joyce
    118.4K views
    Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded
    19:27
    Suspension Self Bondage Sissy Maid in Chastity, Gagged and Blindfolded
    Derek6699
    11.9K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    Sissy maid in Chastity Ass to mouth and sissygasm
    07:02
    Sissy maid in Chastity Ass to mouth and sissygasm
    Mariana Taylor
    3.6K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    297K views
    Sexy sissy maid in chastity suck dick
    05:24
    Sexy sissy maid in chastity suck dick
    Felixa Branca
    5.7K views
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    05:27
    Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot
    ActorFab
    242.5K views
    Sissy Maid in Chastity Desperate in Bed
    01:24
    Sissy Maid in Chastity Desperate in Bed
    KiraszaSissy
    4.4K views
    Sissy Sex Slave
    07:00
    Sissy Sex Slave
    Kapri Sun
    60.1K views
    Sissy maid in chastity bouncing on large dildo
    01:35
    Sissy maid in chastity bouncing on large dildo
    TamaraTv
    13.3K views
    Transerotica Lovely TS Natalie Mars Rammed Hard After BJ
    19:43
    Transerotica Lovely TS Natalie Mars Rammed Hard After BJ
    Trans Erotica
    169.6K views
    Sissy Maid in chastity rides a dildo
    07:46
    Sissy Maid in chastity rides a dildo
    7.1K views
    Sissy chastity cage hardcore anal playplay
    02:44
    Sissy chastity cage hardcore anal playplay
    Lexi Faith
    124.3K views
    Pink sissy maid in chastity
    00:37
    Pink sissy maid in chastity
    1.7K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    231.7K views
    Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post
    32:38
    Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post
    Derek6699
    66K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand
    09:21
    Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand
    Sissy Candy
    17.9K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    953.2K views
    Sissy Maid in Bondage Sucking and Fucking Her Dildo
    08:22
    Sissy Maid in Bondage Sucking and Fucking Her Dildo
    FapHouse
    2.7K views
    I can't believe i'm posting this! BBC Fucks Sissy
    00:50
    I can't believe i'm posting this! BBC Fucks Sissy
    Onlyfans
    446.3K views
    Sissy Maid in Self Bondage Plays with Her Sex Doll
    25:14
    Sissy Maid in Self Bondage Plays with Her Sex Doll
    Sissy Candy
    11.4K views
    Sissys in chastity
    03:40
    Sissys in chastity
    776.5K views
    Inescapable Self Bondage Steel Fiddle Sissy Maid in Chasity Gagged and Ballet Boots
    37:15
    Inescapable Self Bondage Steel Fiddle Sissy Maid in Chasity Gagged and Ballet Boots
    Derek6699
    11.7K views
    Lola Sissification 2 Part 1 - G018
    07:29
    Lola Sissification 2 Part 1 - G018
    Lola Femme
    714K views
    Sissy Maid in Self Bondage Armbinder Hogtie
    19:09
    Sissy Maid in Self Bondage Armbinder Hogtie
    Derek6699
    5.8K views
    She Is a Feminization Academy Graduate
    08:12
    She Is a Feminization Academy Graduate
    Pure Ts
    74.3K views
    Sissy Maid Spanked and Whipped in Chastity Bondage
    05:25
    Sissy Maid Spanked and Whipped in Chastity Bondage
    Derek6699
    75.7K 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
    280.8K 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
    Sissyfication
    43:09
    Sissyfication
    1M views
    Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom
    07:25
    Sissy Maid Cums & Squirts Hard from Anal Fucking Machine in Chastity Cage - Jessica Bloom
    Jessica Bloom
    25.3K 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
    FapHouse
    138.2K views
    Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine
    11:26
    Latex Sissy Maid Candy in Chastity and Bondage Stuck on a Fucking Machine
    FapHouse
    13.3K views
    Rented Out by His Mistress
    06:12
    Rented Out by His Mistress
    Pure Ts
    71.7K views
    Redhead Sissy maid practicing her sissygasms frustrating in chastity, thick black emperor gloves, fishnets, heels
    04:09
    Redhead Sissy maid practicing her sissygasms frustrating in chastity, thick black emperor gloves, fishnets, heels
    JessicaXD
    1.3K 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
    76.4K views
    Sissy Maid Candy Fucks Some of Her Dildos While Locked in Chastity
    09:33
    Sissy Maid Candy Fucks Some of Her Dildos While Locked in Chastity
    Sissy Candy
    10K 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
    181.3K views
    Sissy Maid Cums in Chastity Self Bondage
    09:35
    Sissy Maid Cums in Chastity Self Bondage
    Derek6699
    4K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Sissy Maid Cums in Chastity and in Bondage and Swallows Her Sissy Cum
    15:26
    Sissy Maid Cums in Chastity and in Bondage and Swallows Her Sissy Cum
    Sissy Candy
    8.9K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    378.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Maid In Chastity

    • Sissy Chastity Fucked by Bull
    • A Pretty Boy Gets Feminized
    • Caught Wearing Sisters Clothes
    • Femboy Domination and Tortured
    • Femdom Bisex Slave Crossdresser
    • Submissive Transvestite Training
    • The Sissy's Future
    • Transformed Into Slut
    • Secret Sissyboy
    • Slutty Nasty Crossdressing Gurl
    • Feminization BDSM
    • Sissyslut
    • Fuck My Ass Please Dirty Talk
    • Male to Female Transformation Fantasy
    • Tied up Gangbang
    • White Whore for Black Pimp
    • Multiple Continuous Cum 10 Times
    • Mini Skirt No Panties
    • Sissification Process
    • Cuckold Humiliation
    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