PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Big Sissy Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    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
      961.5K views
    • Big sissy training compilation
      03:50
      Big sissy training compilation
      Lola Spais
      1.5K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      655.9K views
    • Big sissy training
      03:29
      Big sissy training
      Lola Spais
      2.1K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • Big Sissy Training Compilation!
      06:35
      Big Sissy Training Compilation!
      Lola Spais
      10.9K views
    • girlcock brainwashing - sink even deeper
      17:10
      girlcock brainwashing - sink even deeper
      394.7K views
    • Ryley Rails JOI Sissy Training
      06:51
      Ryley Rails JOI Sissy Training
      TSRyley
      15.1K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M 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
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Sissy training for your feminization
      03:56
      Sissy training for your feminization
      Allmylinks
      19.9K views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      864.4K views
    • Kimber Haven BBC Sissy Training
      08:45
      Kimber Haven BBC Sissy Training
      Kimberhaven
      90.9K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      745.4K views
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Bailey Wilde
      299.1K 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
    • Dreamscape Sissy training
      10:20
      Dreamscape Sissy training
      2.6M views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      706.6K views
    • Sissy Training Volume 4 - Daddy's Home
      05:47
      Sissy Training Volume 4 - Daddy's Home
      302.2K views
    • Latin Mature Tranny Predator with Monster Cock Fuck a Slave
      09:21
      Latin Mature Tranny Predator with Monster Cock Fuck a Slave
      8M views
    • Relevant Short videos

      Big Sissy Training Compilation!
      Big Sissy Training Compilation!
      Lola Spais
      1.9K views
      Big sissy training compilation
      Big sissy training compilation
      Lola Spais
      178 views
      Big sissy training
      Big sissy training
      Lola Spais
      169 views
      Sissy Crossdresser Riding a Dildo and Cum Sissy Training Anal Training
      Sissy Crossdresser Riding a Dildo and Cum Sissy Training Anal Training
      Twokisses
      3.6K views
      Fucking My Sissy Ass with Big Toys - Sissy Training 014
      Fucking My Sissy Ass with Big Toys - Sissy Training 014
      JenniferStarTS
      1.9K views
      Sissy Training to get a proper ass to fuck for big black kings
      Sissy Training to get a proper ass to fuck for big black kings
      1.3K views
    • Sissy training for your feminization
      04:00
      Sissy training for your feminization
      Samantha Sissy World
      178K views
    • Sissy  Mind Fuck
      09:35
      Sissy Mind Fuck
      750.7K views
    • Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
      10:08
      Sissy Training - Dominatrix Pegs Goth Sissy and Makes Her Swallow Cum
      Bailey Wilde
      47.3K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • Sissy training
      04:13
      Sissy training
      72.6K views
    • EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
      36:39
      EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
      1.7M views
    • BBC vs SISSY TRAINING MONTAGE
      07:47
      BBC vs SISSY TRAINING MONTAGE
      47.2K views
    • You're Straight Right- - Sissy Hypno Training
      03:07
      You're Straight Right- - Sissy Hypno Training
      921.2K views
    • Sissy Training 202 Double Trouble
      07:09
      Sissy Training 202 Double Trouble
      TSRyley
      1K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      655.8K views
    • Sissy training
      08:49
      Sissy training
      parttcrossdresser
      34.6K views
    • ULTIMATE SISSY TEST
      08:36
      ULTIMATE SISSY TEST
      1.2M views
    • Sissy Training - Sissygasm Encouragement Jessica Bloom
      05:29
      Sissy Training - Sissygasm Encouragement Jessica Bloom
      Jessica Bloom
      227.2K views
    • Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      08:12
      Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      nbnabunny
      1.6M views
    • Sissy Training Volume 3 - Take BBC like a Bitch
      05:16
      Sissy Training Volume 3 - Take BBC like a Bitch
      325.7K views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.5M views
    • Smoking Hy-pno sissy training 03
      15:28
      Smoking Hy-pno sissy training 03
      41.2K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      286.8K views
    • Sissy training 5
      03:08
      Sissy training 5
      KatyKoroleva
      14.3K views
    • Straight Boy Test (Shemales, Cock)
      16:59
      Straight Boy Test (Shemales, Cock)
      1.7M views
    • Slut Sonechka25 moans loudly and ends with cum spray from anal masturbation. Russian voiceover. Sissy training (2)
      02:35
      Slut Sonechka25 moans loudly and ends with cum spray from anal masturbation. Russian voiceover. Sissy training (2)
      Sonechka25
      86K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      924.6K views
    • Sissy training from Katy Koroleva
      06:52
      Sissy training from Katy Koroleva
      KatyKoroleva
      25.9K views
    • sissy anal cumming trainer
      56:50
      sissy anal cumming trainer
      746K views
    • Sugar Cravsitt Presents: Sissy Training 2
      15:08
      Sugar Cravsitt Presents: Sissy Training 2
      88.1K views
    • Feminized for Girls Night Out (Full Movie)
      23:39
      Feminized for Girls Night Out (Full Movie)
      Bailey Wilde
      550K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Categories

    American
    4K Porn
    HD Videos
    VR Porn
    Shemale Fucks Guy
    Big Cock
    Black
    Shemale Fucks Shemale
    Amateur
    Shemale Fucks Girl
    Sissy
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Cum In Mouth
    Big Black Cock
    Big Ass
    Creampie
    Bareback
    Cumshot
    Mature
    Homemade
    Teen
    Masturbation
    Domination
    Anal
    Brazilian
    Solo
    Asian
    Transgender
    BBW
    Mexican
    Cartoon
    Interracial
    Vintage
    Japanese
    Big Tits
    Young
    Small Cock
    Thai
    Lingerie
    Trans Woman
    Gangbang
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Rough Sex
    Couple
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Outdoor
    Handjob
    Chinese
    Fetish
    Hentai
    FTM
    Group Sex
    Massage
    Bondage
    Pissing
    British
    Double Penetration
    Role Play
    Behind The Scenes
    German
    Anal Toy
    SFW
    All categories
    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