PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale

    Sissy Punishment Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Punishment
    Sissy Punishment Mistress
    Sissy Petticoat Punishment
    Sissy Caning Punishment
    Cuckold Sissy Punishment
    Sissy Maids Punishment
    Sissy Ball Punishment
    Sissy Slut Punishment Bondage
    Sissy Punishment Fucking Machine
    Nasty Punishment for Sissy Boy
    Strict Granny With Sissy Punishment
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      44:10
      Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      alinanightsky
      224.3K views
    • Sissy Punishment!
      00:47
      Sissy Punishment!
      61K views
    • Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
      11:20
      Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
      alinanightsky
      301.3K views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.1M views
    • Extreme Hard Spaking for the Maso Cunt
      08:02
      Extreme Hard Spaking for the Maso Cunt
      ActorFab
      193.6K views
    • Sissy Cums Too Early And Gets Punished With Rough Fucking.
      03:20
      Sissy Cums Too Early And Gets Punished With Rough Fucking.
      953.5K views
    • Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
      12:58
      Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2
      Mamou5891
      59.2K views
    • Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      05:43
      Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      alinanightsky
      341.3K views
    • Black tgirl with giant tool fucking a white ass fat faggot
      11:38
      Black tgirl with giant tool fucking a white ass fat faggot
      Latina Tranny
      1.5M views
    • Shemale Punishes Her Puffy Nipples Until Lactation
      05:40
      Shemale Punishes Her Puffy Nipples Until Lactation
      fermerino
      182.6K views
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      ActorFab
      253.2K views
    • Sissy Slave Tranny Punished & Fucked - Full Video
      10:46
      Sissy Slave Tranny Punished & Fucked - Full Video
      Tranny Danni
      869.2K views
    • Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
      08:09
      Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
      Kitsy Meow
      170.2K views
    • SISSY CUMS TOO EARLY AND GETS PUNISHED WITH ROUGH FUCKING
      02:35
      SISSY CUMS TOO EARLY AND GETS PUNISHED WITH ROUGH FUCKING
      568K views
    • Maso Whore Fucked and Slapped Like Good Slave
      16:30
      Maso Whore Fucked and Slapped Like Good Slave
      ActorFab
      99.3K views
    • Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!
      00:43
      Tranny Domina goes shopping... Public ballbusting and nipple torture in the supermarket and in the city!
      TV_Helena
      519.1K views
    • Melody Tied up, Teased and Analised
      35:07
      Melody Tied up, Teased and Analised
      Melodyfluffington
      457.6K views
    • The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj
      11:12
      The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj
      Kink TS
      12.4K views
    • TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
      12:05
      TRANSEROTICA Sub TS Natalie Mars Bound by MILF Dee Williams
      Trans Erotica
      441.5K views
    • Daddy domination over his sissy sex slave and to taught her that my place is under his balls
      02:46
      Daddy domination over his sissy sex slave and to taught her that my place is under his balls
      alinanightsky
      139.5K views
    • Kigurumi Cuffed and Electrostim
      10:07
      Kigurumi Cuffed and Electrostim
      Vemura
      22.4K views
    • Dia de Muertos Mummy Pumps and Punishes her Lactating Nipples with a Vacuum Machine
      12:49
      Dia de Muertos Mummy Pumps and Punishes her Lactating Nipples with a Vacuum Machine
      fermerino
      22.4K views
    • Hard punishment and sex. KitsyMe0w
      11:33
      Hard punishment and sex. KitsyMe0w
      Kitsy Meow
      130.7K views
    • tranny punishes horny slut Iskra
      01:54
      tranny punishes horny slut Iskra
      IskraElectrical49
      87.8K views
    • anything
      09:14
      anything
      1.4M views
    • sissy faggot punished
      04:00
      sissy faggot punished
      102.7K views
    • Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
      05:03
      Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor
      alinanightsky
      400.7K views
    • Doc punishing his bratty submissive femboy sissy Michele
      23:50
      Doc punishing his bratty submissive femboy sissy Michele
      Sissy Michelle MTF
      151.5K views
    • Hard Belting my sissy slave two
      01:36
      Hard Belting my sissy slave two
      114.3K views
    • Sissy slave Harley Quinn punished and fucked
      04:53
      Sissy slave Harley Quinn punished and fucked
      Tranny Danni
      354.5K views
    • BDSM Sissy Slut get punish and hits
      02:37
      BDSM Sissy Slut get punish and hits
      alinanightsky
      101.2K views
    • Sissy slut non stop edging as punishment
      12:23
      Sissy slut non stop edging as punishment
      99.1K views
    • anal destruction and face slapping for maso whore
      10:41
      anal destruction and face slapping for maso whore
      ActorFab
      91.7K views
    • Trans sissy MILF Karolina electro torture
      13:55
      Trans sissy MILF Karolina electro torture
      T Transmilfkarolina
      109.8K views
    • Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH
      01:16
      Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH
      TV_Helena
      60.9K views
    • Mrs.Principal Punishes Student Roleplay _ Futa Dominium Chapter 2: Carnage
      06:01
      Mrs.Principal Punishes Student Roleplay _ Futa Dominium Chapter 2: Carnage
      Asura
      26.5K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.8M views
    • Punish Chair, Let Me Cum to Becoming a Fountain
      03:18
      Punish Chair, Let Me Cum to Becoming a Fountain
      XiangYan
      6.2K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.7M views
    • Dirty Bitch Punishes Ass
      09:46
      Dirty Bitch Punishes Ass
      Analslob
      3.8K 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
    • Good sissy slut in pink baby-doll outfit take all hit, lick legs, and suck dick from his Owner, for prove that she is good gir
      02:27
      Good sissy slut in pink baby-doll outfit take all hit, lick legs, and suck dick from his Owner, for prove that she is good gir
      alinanightsky
      92.1K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.3M views
    • Sissy Maid Self Bondage Electro Punishment
      36:35
      Sissy Maid Self Bondage Electro Punishment
      Derek6699
      101.2K views
    • Hard Belting my sissy slave
      03:46
      Hard Belting my sissy slave
      125K views
    • Cum Punishment and Education
      07:44
      Cum Punishment and Education
      128.7K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      312.8K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Sissy Punishment

    • Sissy Humiliated
    • Crossdresser Humiliation
    • Caught Crossdressing Pegging Punishment
    • Femboy Punished
    • Feminized and Fucked
    • Extreme Filthy
    • Punishing
    • Feminization Bondage
    • Caged Sissies
    • Rough Sex
    • Permanent Sissification
    • Crossdress Blackmail
    • Sissys Get Blacked
    • Handcuffed
    • Ruined
    • Cruel Domination
    • Secret Sissyboy
    • Sissy Torture
    • Femdom Chastity
    • Forced Orgasm
    Monetize your content
    Become a creator

    xHamster

    • About us
    • 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

    Earn money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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