PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    HAPPY LUNAR NEW YEAR! 🌙✨ Faphouse Limited-Time Sale!

    Sissy Halloween Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Halloween
    Funny Halloween Party Sissy Caption
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Sissy Slave
    Sissy Boy
    Young Sissy
    Femdom Sissy
    Sissy Slut
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.8M views
    • Your Satin Sissy Halloween Costume
      10:48
      Your Satin Sissy Halloween Costume
      Natalie Napoli
      2.4K views
    • Sissyfication
      43:09
      Sissyfication
      1.1M views
    • Fat Sissy Halloween Treat.
      11:04
      Fat Sissy Halloween Treat.
      Xshen Hunk
      4.1K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.3M views
    • Happy Sissy Halloween
      01:44
      Happy Sissy Halloween
      JonasBen
      2.4K views
    • Sissy identity
      08:50
      Sissy identity
      613.8K views
    • Fucking after Halloween party with a sissy bitch
      14:12
      Fucking after Halloween party with a sissy bitch
      Saranji
      209.8K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1M views
    • 2 SISSY SLUTS HALLOWEEN GANGBANG
      24:59
      2 SISSY SLUTS HALLOWEEN GANGBANG
      539.9K views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      970.1K views
    • Halloween Succubus cosplay Facesitting Deepthroat Face Fuck, hentai japanese shemale cosplay 8
      04:25
      Halloween Succubus cosplay Facesitting Deepthroat Face Fuck, hentai japanese shemale cosplay 8
      Haru
      26.9K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Sexy Halloween foursome orgy Part 1 with 2 TGirls and mature couple
      25:44
      Sexy Halloween foursome orgy Part 1 with 2 TGirls and mature couple
      Lisa Essex
      27.8K views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      898.9K views
    • Sexy Halloween foursome orgy Part 2 with 2 TGirls and mature couple
      28:50
      Sexy Halloween foursome orgy Part 2 with 2 TGirls and mature couple
      Lisa Essex
      20.7K views
    • Sissy Mind Alteration Video!
      04:45
      Sissy Mind Alteration Video!
      427.2K views
    • Sissy 6
      19:29
      Sissy 6
      1.4M views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      720.5K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      925.4K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      604.9K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      683.9K views
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Sissy  Mind Fuck
      09:35
      Sissy Mind Fuck
      777.6K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      793.9K views
    • Emasculate your mind
      13:52
      Emasculate your mind
      507.7K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.5M views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.9M views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      757.1K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2.2M views
    • sugar Cravsitt Presents: BBC 3
      58:34
      sugar Cravsitt Presents: BBC 3
      2.4M views
    • Tv is for Sissies (Full Video)
      56:35
      Tv is for Sissies (Full Video)
      646K views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      276.1K views
    • My step sister turned me into her trans wife
      05:13
      My step sister turned me into her trans wife
      CutePinkUnicorn
      143.6K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      1M views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      146K views
    • Sissy Boy3
      33:27
      Sissy Boy3
      2M views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      415.8K views
    • Sissy delicious (Part 2)
      13:40
      Sissy delicious (Part 2)
      203.2K views
    • Lily DeMure Blowjob & Doggy
      11:54
      Lily DeMure Blowjob & Doggy
      1.6M views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.7M views
    • Sissy Feminization
      07:42
      Sissy Feminization
      439.9K views
    • Submit to Daddy sissy trainer
      05:26
      Submit to Daddy sissy trainer
      446.2K views
    • My wife told me to play this
      11:13
      My wife told me to play this
      993.9K views
    • SissyFace Sissy Captions Hypno Compilation
      11:18
      SissyFace Sissy Captions Hypno Compilation
      556.2K views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      731.1K 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 Halloween

    Sissy Femboy Lingerie
    Crossdresser and Boyfriend
    Crossdressing Boys
    Crossdress Halloween Costume
    Hot Crossdressers
    Dressing as a Girl
    Tranny Skirt
    Mature Goth
    Femboys in Leggings
    Gay Sissyboy
    Transvestit
    Trap Heels
    Crossdressing Sluts
    Crossdresser Fantasy
    Sissy-Boys
    Sissy Catsuit
    Transvestite Party UK
    Caught Wearing Panties
    Sexy Young Crossdressers
    Cross Dresser Fucked
    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