PornPorn Transgender • US
  • Straight
  • Gay
  • Transgender
  • 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
    • 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
    Subscriptions Liked Watch History
    Newest Videos Best Videos Short Videos Top Creators Awards 2025
    • American
    • 4K Porn
    • HD Videos
    • VR Porn
    • Amateur
    • Anal
    • Anal Masturbation
    • Anal Toy
    • Asian
    • Babysitter
    • Bareback
    • BBW
    • BDSM
    • Behind The Scenes
    • Big Ass
    • Big Black Cock
    • Big Cock
    • Big Tits
    • Black
    • Blowjob
    • Bondage
    • Brazilian
    • British
    • Cartoon
    • Chinese
    • Colombian
    • Compilation
    • Couple
    • Creampie
    • Cuckold
    • Cum In Mouth
    • Cumshot
    • Dildo
    • Domination
    • Double Penetration
    • English
    • Fetish
    • FTM
    • Gangbang
    • German
    • Group Sex
    • Guy Fucks Shemale
    • Handjob
    • Hentai
    • Homemade
    • Indian
    • Interracial
    • Japanese
    • Ladyboy
    • Lingerie
    • Massage
    • Masturbation
    • Mature
    • Mexican
    • MILF
    • Outdoor
    • Petite
    • Pissing
    • POV
    • Public
    • Role Play
    • Rough Sex
    • SFW
    • Shemale Fucks Girl
    • Shemale Fucks Guy
    • Shemale Fucks Shemale
    • Sissy
    • Small Cock
    • Small Tits
    • Solo
    • Stockings
    • Teen
    • Thai
    • Threesome
    • Trans Man
    • Trans Woman
    • Transgender
    • Vintage
    • All categories

    Sissies in Chastity Trans Porn Videos

    All Short videos
    Newest
    Best Videos
    Premium Videos
    By Rating
    • By Rating
    • By Views
    • By Comments
    Date
    • All
    • 1 Day
    • 7 Days
    • 30 Days
    • Year 2026
    • Year 2025
    Quality
    • All
    • 720p+
    • 1080p+
    • 2160p+
    FPS
    • All
    • 30 FPS
    • 60 FPS
    Duration
    • All
    • 0~2 min
    • 2~5 min
    • 5~10 min
    • 10~30 min
    • 30+ min
    • Full Video
    Production
    • All
    • Producers
    • xHamster Creators
    Sissy
    Sissy Chastity
    Young Sissy
    Sissy Feminization
    Sissy Crossdresser
    Amateur Sissy
    Sissy Fuck
    Submissive Sissy
    Sissy Blowjob
    Homemade Sissy
    Sissy Lingerie
    Mommy Sissy
    Russian Sissy
    Sissy Gangbang
    Sissy Compilation
    Beautiful Sissy
    Sissy Creampie
    Sissy Dominated
    By clicking the content you will also see an ad. AD
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    FapHouse
    400.3K views
    Bound sissy in chastity gets BBC
    07:46
    Bound sissy in chastity gets BBC
    958K views
    2032 - the Bwno Future
    15:06
    2032 - the Bwno Future
    ChristineWest120
    124.6K 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
    68.2K views
    Sissys in chastity
    03:40
    Sissys in chastity
    780.1K views
    Sissy Chastity Maid Service Training With Ria Bentley
    07:07
    Sissy Chastity Maid Service Training With Ria Bentley
    Ria_Bentley
    45.6K views
    Total Sissy Amnesia
    13:20
    Total Sissy Amnesia
    Natalie Napoli
    31.9K views
    Beautiful Sissy in chastity enjoys being fucked
    09:38
    Beautiful Sissy in chastity enjoys being fucked
    749K 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
    207.3K views
    Sissy in chastity fucked by different people
    01:41
    Sissy in chastity fucked by different people
    Onlyfans
    534K views
    Asian Sissy Chastity Anal Cumshot
    07:41
    Asian Sissy Chastity Anal Cumshot
    CuteAsianSissy
    77.5K views
    Sissy Bride in Chastity
    05:48
    Sissy Bride in Chastity
    Pure Ts
    21.5K views
    real sissy full in chastity
    13:34
    real sissy full in chastity
    Many Vids
    641.1K 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
    182.5K views
    Transgender sissy joyce in chastity shows hormone progress
    05:16
    Transgender sissy joyce in chastity shows hormone progress
    FapHouse
    89.2K views
    All sissy should be loked in chastity
    03:26
    All sissy should be loked in chastity
    347.7K views
    Best Caged Only orgasms compilation
    06:42
    Best Caged Only orgasms compilation
    boobyb0y
    118.6K views
    BBC Daemon Loki Breeds Femboy Trap Nun in Chastity
    03:25
    BBC Daemon Loki Breeds Femboy Trap Nun in Chastity
    Maskedloki9
    582.8K 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
    171.8K views
    How to Put on Flat Chastity Cage Guide (Jessica Bloom)
    06:08
    How to Put on Flat Chastity Cage Guide (Jessica Bloom)
    Jessica Bloom
    34.9K views

    Best Sissies in Chastity Shemale Short Videos

    Thrilling moment from "vlada cute sissy in chastity and her big hole"
    Thrilling moment from "vlada cute sissy in chastity and her big hole"
    Vladasexytrans
    1.1K views
    crossdresser slut | Clip 1
    crossdresser slut | Clip 1
    violet_bisex
    259 views
    Mean Chastity Keyholders Gone Wild
    Mean Chastity Keyholders Gone Wild
    Brat Perversions
    409 views
    Must-see moment from "Vlada fuck ass in chastity cage"
    Must-see moment from "Vlada fuck ass in chastity cage"
    Onlyfans
    1.3K views
    Memorable moment from "Sissy goth in latex self bondage with giant plug and cock gagball"
    Memorable moment from "Sissy goth in latex self bondage with giant plug and cock gagball"
    Vane03_siss
    375 views
    Captivating moment from "Submissive slut play with her big ass with BWC"
    Captivating moment from "Submissive slut play with her big ass with BWC"
    Crystal Phoenix
    845 views
    Fucking Mtf Chastity Charlie 2
    08:12
    Fucking Mtf Chastity Charlie 2
    Jason With Women - Masculine Jason
    30.8K views
    2 sexy slutty sissies and 1 BBC
    03:32
    2 sexy slutty sissies and 1 BBC
    Ericka Sprinkle
    176.9K views
    Sissys Breast Pumping Session Enlarging my boobs
    09:46
    Sissys Breast Pumping Session Enlarging my boobs
    KiraszaSissy
    9K views
    Two sissy sluts sharing the same BBC
    04:29
    Two sissy sluts sharing the same BBC
    Ericka Sprinkle
    194.8K views
    Asian Sissy Mastubate in Chastity and Cum
    07:12
    Asian Sissy Mastubate in Chastity and Cum
    CuteAsianSissy
    84.1K 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
    134.7K views
    Trans Slut Fits Two Huge Dicks, Balls Deep in Her Holes at the Same Time
    10:02
    Trans Slut Fits Two Huge Dicks, Balls Deep in Her Holes at the Same Time
    MJ
    19.7K views
    At Her Mercy: Hot Trans Domme Trains You
    11:12
    At Her Mercy: Hot Trans Domme Trains You
    Many Vids
    42.9K views
    Negative Chastity cum with vibrator
    02:12
    Negative Chastity cum with vibrator
    boobyb0y
    122.8K views
    SISSIES IN CHASTITY
    02:34
    SISSIES IN CHASTITY
    221.8K views
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    11:21
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    FapHouse
    52.8K views
    Fucking after Halloween party with a sissy bitch
    14:12
    Fucking after Halloween party with a sissy bitch
    Saranji
    203K views
    Try to use my new Chasity in restroom
    01:52
    Try to use my new Chasity in restroom
    FapHouse
    158K 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
    67K views
    SISSYBOI FEMBOI WITH CHASTITY CAGE  RIDING INTERRACIAL BBC HARD
    01:35
    SISSYBOI FEMBOI WITH CHASTITY CAGE RIDING INTERRACIAL BBC HARD
    Alesissyboi
    182.4K views
    Chastity ass pounded sissy
    03:43
    Chastity ass pounded sissy
    Lockedupunicorn
    58.1K views
    No Better Place for a Sissy to Cum then Her Own Mouth! Yum!
    06:44
    No Better Place for a Sissy to Cum then Her Own Mouth! Yum!
    MJ
    6.8K views
    Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat
    07:04
    Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat
    MJ
    9.3K views
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    06:12
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    FapHouse
    7.8K views
    sissy in chastity swallow cum
    19:06
    sissy in chastity swallow cum
    Many Vids
    433.3K views
    Trap Caged Orgasm
    01:54
    Trap Caged Orgasm
    FapHouse
    34.7K views
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    06:12
    Big Dick Tranny Claus Disciplines Caged Sissy Christmas Elf
    Ria_Bentley
    7.5K views
    Two sexy slutty sissies sharing a massive BBC
    04:58
    Two sexy slutty sissies sharing a massive BBC
    FapHouse
    62.5K views
    Sissy cuckold in chastity cage watching her girlfriend getting fucked by her lover. Part 2
    08:23
    Sissy cuckold in chastity cage watching her girlfriend getting fucked by her lover. Part 2
    Traviezisha
    10.3K views
    BBC pouding Sissy femboy in chastity missionary
    03:10
    BBC pouding Sissy femboy in chastity missionary
    Alesissyboi
    115K views
    Cute Asian Sissy JOI Cumshot
    06:39
    Cute Asian Sissy JOI Cumshot
    FapHouse
    12.8K 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
    31K views
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 10
    10
    Next

    Categories Related to Sissies in Chastity

    • Male to Female Transformation
    • First Time With Trans Woman
    • Teen Traps and Sissy Femboys
    • Shemale Chastity
    • Beautiful Shemales and Girls
    • Real Family Homemade
    • Shemale Stepmom
    • Fucked in Chastity
    • Shemale Sisters Fucking
    • Mature Transvestites

    Searches Related to Sissies In Chastity

    • Real Sissy Chastity Outdoor
    • Sissy Public Cum
    • Sissy-Virgin
    • Sissies in Chastity
    • Taboo Movies Full Length
    • Extreme Sissy Training
    • Dirty Talk Radio
    • Shemale Army
    • Live Broadcast Sex Trans Woman Sex Video
    • Sissies in Prison
    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