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

    Training Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Transformation Training Become Sissy
    Wife Dominates Sissy Training
    Sissy Butt Plug Training
    Sissy Fuck Machine Training
    Sissy Deep Throat Training
    Mrs Lovings Sissy Training
    Latex Sissy Anal Training
    Electric Shock Sissy Training
    Sissy Fag Training Captions
    Sissy Cocksucker Training Captions
    Sissy Bi Cock Training
    Sissy-Dani-In-Training
    Sissy Training for Beta Wimp
    More Sissy Training Penis Shrink
    Big Black Cock Sissy Training
    Kimber Haven BBC Sissy Training
    Sissy Oral Training With Dildo
    Sissy Training Tied to Fuck Machine
    Femdom Anal Training for Sissy Boyfriend
    White Sissy Boi Training for Black Cock
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      476.2K 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
      37.4K views
    • EAT SHEMALE CUM CEI TRAINER PART 2
      35:45
      EAT SHEMALE CUM CEI TRAINER PART 2
      517.3K views
    • I fuck my stepsister's busty for her big pussy
      07:14
      I fuck my stepsister's busty for her big pussy
      Yeison
      2.3M views
    • Sissy Swallow
      08:51
      Sissy Swallow
      342.4K views
    • Mistress Eudora's Anal Slut
      05:28
      Mistress Eudora's Anal Slut
      Loren Aprile
      148.4K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      371.3K views
    • SISSY TRANSFORMATION
      11:07
      SISSY TRANSFORMATION
      653.2K views
    • sissy Trance Sperm Addiction
      14:48
      sissy Trance Sperm Addiction
      292.1K views
    • Admit That You Are a Slut For My Cum
      13:12
      Admit That You Are a Slut For My Cum
      Natalie Napoli
      335.2K views
    • Sissy #1: Accepting Your Destiny
      11:37
      Sissy #1: Accepting Your Destiny
      496.4K views
    • Training to become a sissy cuckold
      03:26
      Training to become a sissy cuckold
      amatorxxx
      624.5K views
    • Sissy identity
      08:50
      Sissy identity
      582.1K views
    • Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
      07:47
      Jerk off While I cum on Your Face Sissy Faggot - Jessica Bloom Humilation JoI
      Jessica Bloom
      328.6K 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
    • AB094 Lustful teacher extreme trained -Milking 65cm dildo  (Chinese and English subtitles)
      03:52
      AB094 Lustful teacher extreme trained -Milking 65cm dildo (Chinese and English subtitles)
      Abby Kitty
      382.2K views
    • Sissy Poppers Trainer 1
      04:07
      Sissy Poppers Trainer 1
      314.8K views
    • SissyAline - Train your sissy pussy, be a buttslut
      09:06
      SissyAline - Train your sissy pussy, be a buttslut
      426.1K views
    • anal orgasm training
      10:17
      anal orgasm training
      155.4K views
    • Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      05:43
      Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl
      alinanightsky
      344K views
    • NO LONGER A MAN! SISSY LOVES COCK NOW!
      07:58
      NO LONGER A MAN! SISSY LOVES COCK NOW!
      717.2K views
    • TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
      06:43
      TS Cumslut Elf Fucked Hard By Santa - Ass to Mouth And Facial Jessica Bloom
      Jessica Bloom
      17.9K views
    • Sissy Training
      12:08
      Sissy Training
      75.7K views
    • POV housemate finds your panties and feminizes you JOI dominant trans girl
      11:53
      POV housemate finds your panties and feminizes you JOI dominant trans girl
      Holly unt
      165.9K views
    • Anal training for experienced anal sluts
      27:27
      Anal training for experienced anal sluts
      231.2K views
    • Kira caught during self-bondage
      02:45
      Kira caught during self-bondage
      Twistedrama
      47.8K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      798.4K views
    • Assfucked by a Sissy
      13:01
      Assfucked by a Sissy
      Natalie Napoli
      15.6K views
    • Sissy Feminization
      07:42
      Sissy Feminization
      426.6K views
    • Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
      05:49
      Anal orgasm, cumshots in my mouth, compilation of my hot cumshots
      LuziaTv
      20.6K views
    • The day I turned into a cumslut!
      02:31
      The day I turned into a cumslut!
      593.7K views
    • Petra,s day in the woods
      30:59
      Petra,s day in the woods
      PetraTVsletje
      89.5K views
    • Sissy faggot fantasy
      29:49
      Sissy faggot fantasy
      292K views
    • Cum ride with me
      12:10
      Cum ride with me
      Katie Fox
      450.6K views
    • Teaching a Fag his place
      13:47
      Teaching a Fag his place
      Kimberhaven
      820.3K views
    • Urethral Tube Stimulation with Chastity Cage
      07:00
      Urethral Tube Stimulation with Chastity Cage
      Reina Hanno
      45.1K views
    • sissy instructions
      04:55
      sissy instructions
      178.3K views
    • Sissy Cum Training
      12:16
      Sissy Cum Training
      138.4K 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
    • Craving CockWhore - Joi Sissy train
      08:45
      Craving CockWhore - Joi Sissy train
      188.4K views
    • Becoming a Sissy
      07:40
      Becoming a Sissy
      500K views
    • Story of when daddy pimped me out. First week. Anal toy.
      08:50
      Story of when daddy pimped me out. First week. Anal toy.
      Sunaxfemiknulla
      19.3K views
    • For Sissies  How to obtain past your oral fixating
      14:15
      For Sissies How to obtain past your oral fixating
      235.4K views
    • Submissive femboy is feminized and fucked
      08:30
      Submissive femboy is feminized and fucked
      Crystal Phoenix
      299.7K 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
    • So You Think You're a Sissy Slut?
      06:37
      So You Think You're a Sissy Slut?
      Mistress Jodie May
      91.3K views
    • Sissies Guide for Loving Anal
      05:04
      Sissies Guide for Loving Anal
      184.9K 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 Sissy

    • Cock Sucking Trainer
    • Instruction for Crossdressers
    • Brainwashing
    • Permanent Sissification
    • Bbc Femboi Compilation
    • Femboy Domination
    • How It Started
    • Cross Dress
    • Ladyboy Bondage
    • Homemade Amateur Lingerie
    • Breeding Party
    • Transgirl Onlyfans
    • Real Schoolgirl
    • Fem Boys
    • Feminized
    • Inverted Chastity Cage
    • On Your Knees
    • Family Nudism Stories
    • Sissysubkrystal
    • Crossdresser Riding
    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