PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    Training A Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Mature Sissy
    Sissy Brainwash
    Sissy Pmv
    Sissy Breeding
    Sissy Gloryhole
    Sissy Deepthroat
    Sissy Joyce
    Mommy Sissy
    Chubby Sissy
    Sissy Test
    Latex Sissy
    Sissy Lingerie
    Sissy Strapon
    Sissy Threesome
    Sissy Facial
    Sissy Bukkake
    Sissy Panties
    German Sissy
    Sissy Bnwo
    Sissy Schoolgirl
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy Swallow
      08:51
      Sissy Swallow
      344.3K views
    • All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody
      10:52
      All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody
      Melodyfluffington
      300.2K views
    • Become Sissy Slut
      10:39
      Become Sissy Slut
      407.9K views
    • Between the Lines & Between My Legs
      14:17
      Between the Lines & Between My Legs
      Gray Perrier
      98K views
    • EAT SHEMALE CUM CEI TRAINER PART 2
      35:45
      EAT SHEMALE CUM CEI TRAINER PART 2
      518.6K views
    • You're Straight Right- - Sissy Hypno Training
      03:07
      You're Straight Right- - Sissy Hypno Training
      926.8K views
    • Teaching a Fag his place
      13:47
      Teaching a Fag his place
      Kimberhaven
      823.5K views
    • Mrs Lovings Sissy Training
      10:13
      Mrs Lovings Sissy Training
      2.3M views
    • sissy Trance Sperm Addiction
      14:48
      sissy Trance Sperm Addiction
      293.9K views
    • Sissy: A slut documentary
      08:12
      Sissy: A slut documentary
      Brat Perversions
      37.2K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      822K views
    • Fuck Us Both Billy
      08:12
      Fuck Us Both Billy
      TSRyley
      101.1K views
    • Kimber's BBC Sissy Trainer
      19:45
      Kimber's BBC Sissy Trainer
      Kimberhaven
      210.6K views
    • She's Going to Get Her Ass Fucked in the Kitchen
      04:57
      She's Going to Get Her Ass Fucked in the Kitchen
      Emmy Angeles
      323.4K views
    • Intense Sissy Training Don't Cum by Sissycouture
      04:15
      Intense Sissy Training Don't Cum by Sissycouture
      449.7K views
    • I fuck my stepmom's friend when she's at her house
      07:02
      I fuck my stepmom's friend when she's at her house
      yesid
      478.2K views
    • NO LONGER A MAN! SISSY LOVES COCK NOW!
      07:58
      NO LONGER A MAN! SISSY LOVES COCK NOW!
      718.9K views
    • My Neighbor Fisting My Ass
      08:59
      My Neighbor Fisting My Ass
      Emmy Angeles
      149.2K views
    • sissy anal cumming trainer
      56:50
      sissy anal cumming trainer
      750.2K views
    • Sissy's asshole is filled up to a meter deep
      17:25
      Sissy's asshole is filled up to a meter deep
      Drift3-4
      721.2K views
    • Sissy #1: Accepting Your Destiny
      11:37
      Sissy #1: Accepting Your Destiny
      499.1K views
    • Relevant Short videos

      TV Is a Sissy Wants to Go Outside and Get Caught
      TV Is a Sissy Wants to Go Outside and Get Caught
      JonasBen
      909 views
      Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails
      Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails
      Sissy Candy
      1.4K views
      Fucking My Ass a Cumming Like a Sissy Bitch - Sissy Trainning - Full Movie
      Fucking My Ass a Cumming Like a Sissy Bitch - Sissy Trainning - Full Movie
      JenniferStarTS
      838 views
      Ifetfuc chastity devices and ball stretching toys.  Humiliation as he is turned to a sissy for mistress.  Painful.
      Ifetfuc chastity devices and ball stretching toys. Humiliation as he is turned to a sissy for mistress. Painful.
      iFetFuc
      3.6K views
      What It Is Like to Have a Sissy Girlfriend Pt3
      What It Is Like to Have a Sissy Girlfriend Pt3
      Sissy Millie Lucy
      666 views
      Train to Be a Sissy Whore - Sissy Training 008
      Train to Be a Sissy Whore - Sissy Training 008
      FapHouse
      154 views
    • Ryley Rails Dominates You
      06:51
      Ryley Rails Dominates You
      TSRyley
      54K views
    • girlcock brainwashing - sink even deeper
      17:10
      girlcock brainwashing - sink even deeper
      400.1K views
    • Sissy Throat Fuck Cum Swallow Training
      05:31
      Sissy Throat Fuck Cum Swallow Training
      447.8K views
    • Sissy Training
      12:08
      Sissy Training
      75.7K views
    • My Biggest Anal Dildo Training Vf
      08:12
      My Biggest Anal Dildo Training Vf
      FapHouse
      58.9K 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
      312.5K views
    • Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony
      07:06
      Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony
      Ria_Bentley
      142.4K views
    • sissy instructions
      04:55
      sissy instructions
      179.2K views
    • SISSYALINE TRAIN YOUR SISSY PUSSY
      09:06
      SISSYALINE TRAIN YOUR SISSY PUSSY
      467.9K views
    • sissy training video
      11:54
      sissy training video
      176.2K views
    • Fisting Double Sissygasm Cumshots
      01:38
      Fisting Double Sissygasm Cumshots
      Lola Spais
      164.4K views
    • Sissy Feminization
      07:42
      Sissy Feminization
      428.6K views
    • Trained to Be Completely Subservient to Him
      08:12
      Trained to Be Completely Subservient to Him
      Pure Ts
      109.8K views
    • 2032 - the Bwno Future
      15:06
      2032 - the Bwno Future
      ChristineWest120
      120.4K views
    • Sissy Cum Swallow Training 2
      03:52
      Sissy Cum Swallow Training 2
      463.7K views
    • YOUR MIND IS WEAK SISSY
      05:54
      YOUR MIND IS WEAK SISSY
      527.5K views
    • Big Breasted Sissy Oils Her Big Fat Tits and Enjoys a Big Fat Cock
      08:42
      Big Breasted Sissy Oils Her Big Fat Tits and Enjoys a Big Fat Cock
      Sissy Slut Chantal Sweet
      58K views
    • Sissies Guide for Loving Anal
      05:04
      Sissies Guide for Loving Anal
      185.6K views
    • Extreme Anal Gape Xxxl Dildo & Fuck Machine
      05:56
      Extreme Anal Gape Xxxl Dildo & Fuck Machine
      FapHouse
      67.8K views
    • Becoming a Sissy
      07:40
      Becoming a Sissy
      502.8K views
    • Trans Girl Masturbating and Cums All Over Her Self
      03:44
      Trans Girl Masturbating and Cums All Over Her Self
      Bella Roar
      156.6K views
    • anal orgasm training
      10:17
      anal orgasm training
      156.5K views
    • Sissy Chastity Maid Service Training With Ria Bentley
      07:07
      Sissy Chastity Maid Service Training With Ria Bentley
      Ria_Bentley
      44K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      697.4K views
    • The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      07:20
      The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      Sonechka25
      39.9K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      115.6K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    9. ...
    10. 80
    80

    Searches Related to Training A Sissy

    • 18 Year Old Creampie
    • Ladyboy Prostate Orgasm
    • Prison Bitch
    • Fuck Machine Extreme Fast
    • Domination JOI
    • Huge Toys Insertions
    • Crossdress Blackmail
    • Transsexual Sex Story
    • Sissyslut
    • Tiny Shemales Love Big Cocks
    • Sissys Get Blacked
    • Latex Maid
    • Thrusting Butt Plug
    • Make Me Cum
    • So Deep He Came so Much
    • Bimbo Blowjob
    • Glory Hole Compilation
    • Sick Twisted Mind
    • Cute Homemade
    • Beautiful Tgirls in Very Hot Scenes
    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