PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    Gay Sissy Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Training
    Sissy Training
    Sissy Crossdresser
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    Sissy Boy
    Sissy Slut
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      864.4K views
    • Compilation cumshot samantha sissy transwoman
      05:39
      Compilation cumshot samantha sissy transwoman
      Samantha Sissy World
      260.6K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      655.9K views
    • Be Gay
      02:36
      Be Gay
      68K views
    • My wife told me to play this
      11:13
      My wife told me to play this
      961.5K views
    • Think This Isn't Gay?
      08:44
      Think This Isn't Gay?
      obeylilith.com
      just added
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • Teen sissy slut secludes herself in nature and fucks her bimbo ass with a huge dilduck
      05:56
      Teen sissy slut secludes herself in nature and fucks her bimbo ass with a huge dilduck
      Sonechka25
      28.2K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      745.4K views
    • Crossdressed Sissy lana get fucked with selfmade gyno chair
      07:37
      Crossdressed Sissy lana get fucked with selfmade gyno chair
      Lana sissy
      16.4K views
    • Real sissy hypnotic
      24:43
      Real sissy hypnotic
      226K views
    • Indian Gay Crossdresser Gaurisissy XXX Sex in Pink Honeymoon Lingerie
      05:29
      Indian Gay Crossdresser Gaurisissy XXX Sex in Pink Honeymoon Lingerie
      Gaurisissy
      5.4K views
    • Sissy  Mind Fuck
      09:35
      Sissy Mind Fuck
      750.7K views
    • Indian Gay Crossdresser Gaurisissy Pressing Her Big Boobs in Balck Saree XXX Sex
      05:36
      Indian Gay Crossdresser Gaurisissy Pressing Her Big Boobs in Balck Saree XXX Sex
      Gaurisissy
      3.2K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      655.8K views
    • Indian Gay Crossdresser Gaurisissy Feeling Horny in Golden Lehanga
      07:14
      Indian Gay Crossdresser Gaurisissy Feeling Horny in Golden Lehanga
      Gaurisissy
      3.3K views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      706.6K views
    • Indian Gay Crossdresser in Rainbow Saree Making Pride for Lgbt XXX
      06:23
      Indian Gay Crossdresser in Rainbow Saree Making Pride for Lgbt XXX
      Gaurisissy
      5.6K views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      709.7K views
    • Workout with my big friend
      07:01
      Workout with my big friend
      Gizly James
      1.2K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • I'm a whore for a client
      03:06
      I'm a whore for a client
      Kinganalbitch
      5.6K views
    • SissyFace Sissy Captions Hypno Compilation
      11:18
      SissyFace Sissy Captions Hypno Compilation
      527.3K views
    • Ripley Rose Rides Her Big Black Dildo
      03:03
      Ripley Rose Rides Her Big Black Dildo
      Ripley Rose
      2.6K views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Sissy anal training
      08:21
      Sissy anal training
      FumikoKatt
      4.5K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M views
    • Mi amigo no de de cojerme
      02:11
      Mi amigo no de de cojerme
      Papiricoo
      3.8K views
    • How You Became A Sissy
      05:20
      How You Became A Sissy
      521.2K views
    • Indian Gay Crossdresser in Golden Lehanga
      01:27
      Indian Gay Crossdresser in Golden Lehanga
      Gaurisissy
      5K views
    • Sissy Summer House Dreams 3
      16:29
      Sissy Summer House Dreams 3
      305.9K views
    • Sasha Earth is a sissy whore fucking her ass with an anal sex toy and dildos at home one
      08:15
      Sasha Earth is a sissy whore fucking her ass with an anal sex toy and dildos at home one
      Sasha Earth
      2K views
    • ULTIMATE SISSY TEST
      08:36
      ULTIMATE SISSY TEST
      1.2M views
    • Crossdresser fuck machine anal training
      09:23
      Crossdresser fuck machine anal training
      CDkimmyslutness
      763 views
    • Sissy Hypno Trip # 11
      12:52
      Sissy Hypno Trip # 11
      361.2K views
    • Mrs Lovings Sissy Training
      10:13
      Mrs Lovings Sissy Training
      2.3M views
    • Become the Whore - Sissy Slut
      07:00
      Become the Whore - Sissy Slut
      195K views
    • sissy training
      15:28
      sissy training
      420.9K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      692K views
    • Ryley Rails JOI Sissy Training
      06:51
      Ryley Rails JOI Sissy Training
      TSRyley
      15.1K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M views
    • How to Swallow Your Own Cum - Sissy Training Guide
      08:54
      How to Swallow Your Own Cum - Sissy Training Guide
      Jessica Bloom
      123.6K views
    • The Sissy Test
      17:18
      The Sissy Test
      513.2K views
    • Sissy training for your feminization
      03:56
      Sissy training for your feminization
      Allmylinks
      19.9K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Sissy training instructional
      17:12
      Sissy training instructional
      229.6K views
    • Sissy Brainwashing Training
      13:46
      Sissy Brainwashing Training
      367.3K 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 Gay Sissy Training

    • Brainwashing You Into Sissy Faggot
    • Sissygasm Training
    • Feminization Male to Crossdresser
    • Trans Trainer
    • Bbc Brainwash
    • Sissification Process
    • Bi Confusion
    • Sissy Trained
    • Bimbo Training
    • A Sissy's Purpose
    • Femboy Transgirl Dom and Sub
    • Permanent Sissification
    • Destroying the Fag
    • Anal Train
    • Sissyfication Process
    • Brainwash
    • First Time Crossdressing
    • Body Swap Gender Transformation
    • Crossdress Training
    • Caught Crossdressing Pegging Punishment
    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