PornPorn Transgender • US
  • Videos
  • Moments
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X (ex Twitter)
    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
    • Shemale Fucks Shemale
    • Big Cock
    • Black
    • 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
    THANKSGIVING MEGA SALE 🤍🎉 Grab the hottest deals!
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Shemale Fucks Shemale
    • Big Cock
    • Black
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Bareback
    • Big Ass
    • Creampie
    • Cumshot
    • Teen
    • Homemade
    • Mature
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Punishment Cbt Porn Videos

    Free Videos
    Moments
    Premium Videos
    Photos
    Sissy Caught
    Sissy Outdoor
    Two Sissies
    Sissy Secrets
    Sissy Confusion
    Sissy Boyfriend
    Degraded Sissies
    Sissy Sex
    Sissy Hardcore
    Sissy Bride
    Sissy Kissing
    Sissy Interracial
    Skinny Sissy
    Sissy Missionary
    Sissy Pussy
    Ai Sissy
    Sissy Dress
    Spun Sissy
    Sissy Rimming
    Sissy Torture
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy Schoolgirl Punishment: Part 1
    07:11
    Sissy Schoolgirl Punishment: Part 1
    67.6K views
    Sexy punishment by hard sissy dick for misspelling
    29:48
    Sexy punishment by hard sissy dick for misspelling
    Anna Rios
    149K views
    A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    01:34
    A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    alinanightsky
    37.8K views
    Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump
    07:40
    Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump
    fermerino
    1.5K views
    Trans Girl with Big Puffy Nipples Lactating and Gets her FAT ASS Spanked and Punished
    07:06
    Trans Girl with Big Puffy Nipples Lactating and Gets her FAT ASS Spanked and Punished
    fermerino
    5.4K views
    Rebeccas Pervertions 8
    11:21
    Rebeccas Pervertions 8
    Rebeccafuxx
    15.2K views
    More maintenance spanking for Kitsy. OTK punishment.
    06:53
    More maintenance spanking for Kitsy. OTK punishment.
    Kitsy Meow
    21.2K views
    Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation
    01:00
    Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation
    Disciplinater
    16.9K views
    Sissy Maids Punishment
    07:53
    Sissy Maids Punishment
    Derek6699
    26.1K views
    Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
    14:26
    Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
    Denise Humain
    40K views
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    23:29
    Sissy Maid Icy Hot Wooden Pony Punishment 2
    Derek6699
    37.1K views
    Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.
    18:52
    Kitsy Me0w. Traditional OTK hand spanking. Sissy transgender with beautiful round ass and thick thighs.
    Kitsy Meow
    24.1K views
    Transgirl lactation, young sissy milks her hormonate tits, teen shemale torture her nipples and slaps them.
    07:50
    Transgirl lactation, young sissy milks her hormonate tits, teen shemale torture her nipples and slaps them.
    fermerino
    50.6K views
    A Sexy Sissy Deer Is Hardcore Fucked by Santa, Deep Throat, Cum on Face, Whipping of a Naughty Girl Turned Into a Cute Reindeer
    00:46
    A Sexy Sissy Deer Is Hardcore Fucked by Santa, Deep Throat, Cum on Face, Whipping of a Naughty Girl Turned Into a Cute Reindeer
    Disciplinater
    30.8K views
    Dirty Bitch Punishes Ass
    09:46
    Dirty Bitch Punishes Ass
    Analslob
    659 views
    Please Don't Tell Countess!
    08:58
    Please Don't Tell Countess!
    Marcy Bathory
    15.9K views
    Tranny dom punishes the perverted panty sniffer! Now he's her bitch!
    01:16
    Tranny dom punishes the perverted panty sniffer! Now he's her bitch!
    TV_Helena
    20K views
    Lustful goth punishes her cunt
    05:05
    Lustful goth punishes her cunt
    Lewdy Lamb
    1.3K views
    New task - cock torture with toothpaste in pantyhose 3
    05:18
    New task - cock torture with toothpaste in pantyhose 3
    Loreleyadd
    32K views
    Kelli gagged with a pee covered penis gag
    05:08
    Kelli gagged with a pee covered penis gag
    Kelli UK
    12.1K views
    Kitsy gets hand spanked OTK.
    11:43
    Kitsy gets hand spanked OTK.
    Kitsy Meow
    16K views
    Sissys Wooden Pony Ballet Boot Torment
    33:24
    Sissys Wooden Pony Ballet Boot Torment
    Derek6699
    19.9K views
    Sissy Ruined Orgasm, Edging And Sounding Hard Cock - Chastity Punishment
    05:20
    Sissy Ruined Orgasm, Edging And Sounding Hard Cock - Chastity Punishment
    Jessica Bloom
    6.4K views
    My first time to try 15 inch King Cock with high speed fucking machine
    08:08
    My first time to try 15 inch King Cock with high speed fucking machine
    Ylvis88
    40.5K views
    Huge dildo is pushed deeper into the ass by rubber bands. BDSM TS self bondage torture. Huge Tits Cup-Z Anal Fuck Extreme deep
    06:07
    Huge dildo is pushed deeper into the ass by rubber bands. BDSM TS self bondage torture. Huge Tits Cup-Z Anal Fuck Extreme deep
    Endless Deeply
    51.8K views
    BDSM Transgirl Lactation Rough Punishment Homonate Puffy Boobs Shemale
    14:51
    BDSM Transgirl Lactation Rough Punishment Homonate Puffy Boobs Shemale
    fermerino
    62.2K views
    Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
    14:42
    Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
    Denise Humain
    27.7K views
    Thick Futa Shemale Nun Fucks Missionary Anal
    08:10
    Thick Futa Shemale Nun Fucks Missionary Anal
    Wraith931
    2.7K views
    Sissy Pussy Wrecking POV
    08:37
    Sissy Pussy Wrecking POV
    Brat Perversions
    690 views
    Voyeurism. Watching My Sissy Slave Do My Sadistic Tasks, Fuck Her Throat and Torment Her Lustful Tender Body
    01:23
    Voyeurism. Watching My Sissy Slave Do My Sadistic Tasks, Fuck Her Throat and Torment Her Lustful Tender Body
    Disciplinater
    13.6K views
    Sissy balls torture ballbusting
    12:44
    Sissy balls torture ballbusting
    cdvaleria1996
    13.8K views
    Nasty Viper🤍Being too sexy can be wrong, and bad Nikke deserves punishment!
    05:21
    Nasty Viper🤍Being too sexy can be wrong, and bad Nikke deserves punishment!
    Nasty Azu
    32.9K views
    Big Nipples Trans Girl Punishes and Slaps her Lactating Tits with Clamps and a Bbc Dildo
    08:19
    Big Nipples Trans Girl Punishes and Slaps her Lactating Tits with Clamps and a Bbc Dildo
    fermerino
    1.1K views
    Roommate Feminized and Fucked for Punishment
    11:12
    Roommate Feminized and Fucked for Punishment
    Bailey Wilde
    53.6K views
    Nun fuck sissy sinner hard and deep
    06:51
    Nun fuck sissy sinner hard and deep
    Saranji
    14.7K views
    Icy Hot Wooden Pony Self Bondage Torture
    17:40
    Icy Hot Wooden Pony Self Bondage Torture
    Derek6699
    24.9K views
    Sucked Under the Bed Helpless and Exposed
    02:45
    Sucked Under the Bed Helpless and Exposed
    Valerie Parker
    558 views
    Spit Slave Cleaning Duties Part 1 of 2 Clean Jessicas Spit And Heels
    08:22
    Spit Slave Cleaning Duties Part 1 of 2 Clean Jessicas Spit And Heels
    Jessica Bloom
    7K views
    Contraband - Part 2 - Heathrow Dungeon Come to Punish for Her Smuggling
    01:35
    Contraband - Part 2 - Heathrow Dungeon Come to Punish for Her Smuggling
    Jasmine_dlight
    8.6K views
    Kitsy gets Maintenance spanking. Adorable socks and feet.
    06:19
    Kitsy gets Maintenance spanking. Adorable socks and feet.
    Kitsy Meow
    12.6K views
    Sissy gets soanked by Domina
    01:39
    Sissy gets soanked by Domina
    Aliska
    8.5K views
    Cute Secretary Trans Girl Cumming and Pissing after Slapping her Balls and Jerking with a Dildo in her Ass
    06:46
    Cute Secretary Trans Girl Cumming and Pissing after Slapping her Balls and Jerking with a Dildo in her Ass
    fermerino
    1K views
    I tied my dick so it wouldn't get hard
    05:07
    I tied my dick so it wouldn't get hard
    cd_aysemmm
    4.1K views
    Spanking naughty Schoolgirl Daphne, close-up shots while chained to the bed and receiving some spanking as punishment
    14:24
    Spanking naughty Schoolgirl Daphne, close-up shots while chained to the bed and receiving some spanking as punishment
    Mrs Samantha
    8.1K views
    Blonde Mistress punishes her Slave Sissy Ass
    32:50
    Blonde Mistress punishes her Slave Sissy Ass
    31.9K views
    10 Minutes of Torment
    18:23
    10 Minutes of Torment
    Derek6699
    21.9K views
    POT in ties
    05:28
    POT in ties
    Jessie Flowers
    8.9K views
    • Back
    • 1
    • ...
    • 4
    • 5
    • 6
    • 7
    • 8
    • ...
    • 80
    • Next

    Searches Related to Sissy Punishment Cbt

    • Ladyboy Ing
    • Hard Doggy
    • Black-Metal-Tranny
    • Sissynat
    • Spitting
    • Your-Sissyslut
    • Detroit Tgirls
    • Sloppy Blowjob
    • Orgasm Denial
    • Look More Girly
    • Femdom Emasculation
    • Naughty at Home
    • Dirtysissykitty
    • Brutal Creampie
    • Sisy Boy
    • Chastity Caged Girls Twitter
    • Furry Shemale Comic
    • Beautiful Passable Crossdressers
    • Sissy for Bambi
    • Sissy-Cori

    xHamster

    • xHamster Shop
    • 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 - 2025, 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