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

    Sissy Training Session 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
    • Sissy Brainwashing Training
      13:46
      Sissy Brainwashing Training
      368.8K views
    • Kimber Haven BBC Sissy Training
      08:45
      Kimber Haven BBC Sissy Training
      Kimberhaven
      90.9K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      691.4K views
    • Dreamscape Sissy training
      10:20
      Dreamscape Sissy training
      2.6M views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      510.2K views
    • Sissy Training
      03:11
      Sissy Training
      Sissy Bambii
      81.9K views
    • Sissy Feminization
      07:42
      Sissy Feminization
      426.6K views
    • Sissy training dreams
      26:14
      Sissy training dreams
      250.2K views
    • Sissy Training
      12:08
      Sissy Training
      75.7K views
    • Brat Perversions Mandatory BBC Sissy Training
      00:38
      Brat Perversions Mandatory BBC Sissy Training
      littlemissbrat
      44.8K views
    • AMBERSIS SISSY CUM SLUT
      06:20
      AMBERSIS SISSY CUM SLUT
      471.6K views
    • blonde femboy fuck machine sissy training!
      13:20
      blonde femboy fuck machine sissy training!
      Cassie Coyote
      96K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      112.7K views
    • Sissy Training Volume 4 - Daddy's Home
      05:47
      Sissy Training Volume 4 - Daddy's Home
      302.2K views
    • Sissy #1: Accepting Your Destiny
      11:37
      Sissy #1: Accepting Your Destiny
      496.4K views
    • Sissy Training for Hotel Housekeeping Job
      12:49
      Sissy Training for Hotel Housekeeping Job
      Bailey Wilde
      77.2K views
    • Intense Sissy Training Don't Cum by Sissycouture
      04:15
      Intense Sissy Training Don't Cum by Sissycouture
      447.5K 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
    • Submit to Daddy sissy trainer
      05:26
      Submit to Daddy sissy trainer
      431.1K views
    • Sissy training for your feminization
      04:00
      Sissy training for your feminization
      Samantha Sissy World
      178K views
    • Become Sissy Slut
      10:39
      Become Sissy Slut
      404.8K views
    • Relevant Short videos

      Deepthroat Training Session for Sissy Elodie
      Deepthroat Training Session for Sissy Elodie
      Elodiefrench
      3.4K views
      Sissy Training Cam Session - All Holes
      Sissy Training Cam Session - All Holes
      JessicaXD
      1.5K views
      Sissy Lisa Toy Session 1
      Sissy Lisa Toy Session 1
      Lisa Rhea Deville
      1.3K views
      Sissy Anna Sophia Appreciation Session: Toys, Anal Training, Ass Massage, Spanking
      Sissy Anna Sophia Appreciation Session: Toys, Anal Training, Ass Massage, Spanking
      Sissy Anna Sophia
      551 views
      An Extraordinary Sex Session with This Extraordinary Sissy Who Breaks All the Rules!
      An Extraordinary Sex Session with This Extraordinary Sissy Who Breaks All the Rules!
      Trans and Co
      457 views
      Mind the Gape Training Quickie Session - Membership Teaser
      Mind the Gape Training Quickie Session - Membership Teaser
      Pussless
      27 views
    • Sissy training
      04:13
      Sissy training
      72.6K views
    • sissy training video
      11:54
      sissy training video
      176.2K views
    • BBC vs SISSY TRAINING MONTAGE
      07:47
      BBC vs SISSY TRAINING MONTAGE
      47.2K views
    • Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      01:17
      Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      Allmylinks
      109.8K views
    • Pulsating Asshole During Orgasm - Sissy Training PT 1
      02:15
      Pulsating Asshole During Orgasm - Sissy Training PT 1
      UncutJuicyCock
      90.7K views
    • Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      10:16
      Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
      Jessica Bloom
      72.8K views
    • Sissy Training (again)
      04:58
      Sissy Training (again)
      Nikki Pinkz
      139.9K views
    • I AM SO READY TO BE A SISSY WHORE FOR MEN
      41:14
      I AM SO READY TO BE A SISSY WHORE FOR MEN
      479.5K views
    • Stretching my Ass - Sissy Training
      07:02
      Stretching my Ass - Sissy Training
      Veronica Sanders
      151.4K views
    • Becoming a Sissy
      07:40
      Becoming a Sissy
      500K views
    • Sissy Training 202 Double Trouble
      07:09
      Sissy Training 202 Double Trouble
      TSRyley
      1.9K views
    • Sissies Guide for Loving Anal
      05:04
      Sissies Guide for Loving Anal
      184.9K views
    • Heterosexual No More (Sissy Training)
      00:36
      Heterosexual No More (Sissy Training)
      littlemissbrat
      31.6K views
    • Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      44:10
      Duck typing being: Pain Whore Alina got beaten, slapped, whipped, throat fucked, was made act like duck for bdsm, face covered w
      alinanightsky
      234.8K views
    • Mistress Laura giving me sissy training
      00:34
      Mistress Laura giving me sissy training
      Sissy Joyce
      143K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      796.8K views
    • Sissy Training
      12:38
      Sissy Training
      763.8K views
    • Turned Into A Cock Loving Sissy
      18:35
      Turned Into A Cock Loving Sissy
      813.3K views
    • Sissy training
      08:49
      Sissy training
      parttcrossdresser
      35.3K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      334.2K views
    • Sissy Training - Sissygasm Encouragement Jessica Bloom
      05:29
      Sissy Training - Sissygasm Encouragement Jessica Bloom
      Jessica Bloom
      227.2K views
    • Your friendly Sissy Trainer GERMAN
      09:22
      Your friendly Sissy Trainer GERMAN
      558.2K views
    • Sissy Training Volume 3 - Take BBC like a Bitch
      05:16
      Sissy Training Volume 3 - Take BBC like a Bitch
      325.7K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      938.3K views
    • Smoking Hy-pno sissy training 03
      15:28
      Smoking Hy-pno sissy training 03
      41.2K views
    • Sissy Trainer Rus - Feminization Instruction
      05:01
      Sissy Trainer Rus - Feminization Instruction
      396.3K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 42
    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
    Transgender
    Asian
    BBW
    Mexican
    Cartoon
    Interracial
    Vintage
    Big Tits
    Japanese
    Young
    Small Cock
    Thai
    Gangbang
    Trans Woman
    Lingerie
    Threesome
    Colombian
    Petite
    BDSM
    Public
    Rough Sex
    Couple
    MILF
    Anal Masturbation
    POV
    Dildo
    Cuckold
    Stockings
    Small Tits
    Babysitter
    Trans Man
    Indian
    Handjob
    Outdoor
    Chinese
    FTM
    Hentai
    Fetish
    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