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

    Cuckold Sissy Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Cuckold
    Training
    Sissy Training
    Sissy Cuckold
    Sissy Crossdresser
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    Sissy Boy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • My wife told me to play this
      11:13
      My wife told me to play this
      953.3K views
    • Sissy Training . How should she pee ? Like a real girl
      05:31
      Sissy Training . How should she pee ? Like a real girl
      Ashlie
      3.9K views
    • EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
      36:39
      EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
      1.6M views
    • Sissy training Extreme CBT electric shock cock pain bdsm
      00:20
      Sissy training Extreme CBT electric shock cock pain bdsm
      iFetFuc
      84.1K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      650.2K views
    • Sissy Training 2
      13:08
      Sissy Training 2
      Z ZZ4
      3.3K views
    • Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
      13:19
      Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
      Holly unt
      70.9K views
    • Sissy training
      16:05
      Sissy training
      SissySimran
      11.9K views
    • Ultimate cuckold tranny humiliation!
      05:36
      Ultimate cuckold tranny humiliation!
      Femdom Austria TS
      67.1K views
    • Between the Lines & Between My Legs
      14:17
      Between the Lines & Between My Legs
      Gray Perrier
      84.2K views
    • sissy Trance Sperm Addiction
      14:48
      sissy Trance Sperm Addiction
      290.4K views
    • Training to become a sissy cuckold
      03:26
      Training to become a sissy cuckold
      amatorxxx
      615.7K views
    • Wife teaches sissy cuckold to eat cum and films it
      05:07
      Wife teaches sissy cuckold to eat cum and films it
      Ashlie
      19.9K views
    • sissy Cuckold SLUT training
      05:15
      sissy Cuckold SLUT training
      164.8K views
    • cuckold swap his wife for a shemale and his wife got fucked
      10:38
      cuckold swap his wife for a shemale and his wife got fucked
      Borntrans
      3.3M views
    • Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
      05:07
      Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
      Usaberilx
      13.5K views
    • BBC Addiction - MY wife lovec big black cock
      15:05
      BBC Addiction - MY wife lovec big black cock
      tattooedb
      41.9K views
    • Come cum inside me black daddy
      01:16
      Come cum inside me black daddy
      Dirtysissywhore
      107.1K views
    • Hypnotic sissy cum.
      13:29
      Hypnotic sissy cum.
      187.1K views
    • Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!
      08:12
      Your Trans BFF Wants to Make You Her Boyfriend's Mall Slut!
      Melissa Masters
      79.7K views
    • EAT SHEMALE CUM CEI TRAINER PART 2
      35:45
      EAT SHEMALE CUM CEI TRAINER PART 2
      513.7K views
    • PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
      04:42
      PorchaeTS tries new homemade chastity Dick dildo to pleasure the Mrs. Total mind trip.
      PorchaeTS
      87.9K views
    • How to Swallow Your Own Cum - Sissy Training Guide
      08:54
      How to Swallow Your Own Cum - Sissy Training Guide
      Jessica Bloom
      121.7K views
    • Sissy coming home from work
      16:12
      Sissy coming home from work
      SissyDaniella
      20K views
    • Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
      13:12
      Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
      Fiona Fortune
      212.5K views
    • Caged Sissy try get pleasure by anal dildo play
      11:54
      Caged Sissy try get pleasure by anal dildo play
      SissyDaniella
      29.8K views
    • Wife films her cuckold eating his own cum
      02:06
      Wife films her cuckold eating his own cum
      Ashlie
      9K views
    • Suck me off 100 Times a Day
      12:40
      Suck me off 100 Times a Day
      Natalie Napoli
      68.8K views
    • Wife makes sissy husband suck BBC
      00:39
      Wife makes sissy husband suck BBC
      307.6K views
    • Sissy fucking new pussy hole
      15:06
      Sissy fucking new pussy hole
      SissyDaniella
      11.2K views
    • GenderX - Wife Wants Husband To Fuck Her Trans Friend
      12:54
      GenderX - Wife Wants Husband To Fuck Her Trans Friend
      GenderX
      2.7M views
    • Sissys deepthroat training on a BBC
      01:59
      Sissys deepthroat training on a BBC
      WaifuStuff
      70.9K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Futanari Mistress Shows you How to Use a Chastity Cage!
      10:17
      Futanari Mistress Shows you How to Use a Chastity Cage!
      fermerino
      6.9K views
    • Sissy Whore Training 3
      19:43
      Sissy Whore Training 3
      cdCrystal
      14.2K views
    • Sissy Intro at home and pleasing BBC Dildo
      13:05
      Sissy Intro at home and pleasing BBC Dildo
      SissyDaniella
      13.7K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.7M views
    • Horny Sissy on Way Home
      14:02
      Horny Sissy on Way Home
      SissyDaniella
      12K views
    • SISSY CUCKOLD
      04:24
      SISSY CUCKOLD
      178K views
    • Sissy Compiliation
      12:49
      Sissy Compiliation
      SissyDaniella
      6.4K views
    • Teaching a Fag his place
      13:47
      Teaching a Fag his place
      Kimberhaven
      804.7K views
    • Sissy in Red playing with Sex Maschine
      12:40
      Sissy in Red playing with Sex Maschine
      SissyDaniella
      5.3K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      736.2K views
    • Sissy get fucked by sex maschine on table again.png
      11:00
      Sissy get fucked by sex maschine on table again.png
      SissyDaniella
      3.6K views
    • Good cuck
      23:02
      Good cuck
      307.8K views
    • My husband became a sissy
      06:14
      My husband became a sissy
      Kmarcouple
      14.7K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      352.8K 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 Cuckold Sissy Training

    • Femdom Sissy Training
    • Turning Cuck Husband Into Faggot
    • Crossdresser Fucking Boss in Hotel Room
    • Dirty Talking Wife Cuckold
    • How I Became a Shemale Slave
    • Cock Worship Trainer
    • Mrs Loving Sissy Training
    • Feminization BDSM
    • Femboy Sissification
    • Crossdressing Husband Caught by Wifes
    • Tranny Submissive Servant Girl
    • Sissyfication Process
    • Sissy Cocksucker Training
    • Married Straight Man Breeds Again
    • Girlcock Brainwashing
    • Sissy-Dani-In-Training
    • Slut Trainer
    • The Sissy's Future
    • Secret Sissyboy
    • Sissy-Virgin
    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