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

    Anal Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Anal
    Training
    Anal Stretching Training
    Shemale Anal Training
    Anal Training Dildo
    Crossdresser Anal Training
    Sissy Anal Training Compilation
    Latex Sissy Anal Training
    Femdom Anal Training for Sissy Boyfriend
    Sissy Training
    Femboy Anal
    Anal Orgasm
    Sissy Anal
    Anal Creampies
    Crossdresser Anal
    Shemale Anal
    Trans Anal
    Double Anal
    Anal Sissygasm
    Anal Masturbation
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • Trans Slut Will Receive Anal Training From a Dominant Woman
      03:47
      Trans Slut Will Receive Anal Training From a Dominant Woman
      Emmy Angeles
      18.2K views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      658.7K views
    • Asian Twink Femboy Anal Training with Daddy
      03:03
      Asian Twink Femboy Anal Training with Daddy
      346.3K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M views
    • Submissive Ladyboy Anal Training Casting and Fingering
      08:12
      Submissive Ladyboy Anal Training Casting and Fingering
      FilmmakerDiaries
      14.4K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.8M views
    • Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
      07:25
      Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged
      Jessica Bloom
      3.4K 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
    • Anal training for Sissy Blaire_18. Dominatrix Nika inserts anal beads into her Sissy's little ass.
      07:49
      Anal training for Sissy Blaire_18. Dominatrix Nika inserts anal beads into her Sissy's little ass.
      Dominatrix Nika
      32K views
    • sissy training
      39:53
      sissy training
      133.3K views
    • 30 mins anal training for sissies
      30:00
      30 mins anal training for sissies
      51.7K views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      865.9K views
    • Anal Training Riding Dildo Util I Cum Sissy Amateur Crossdresser
      16:54
      Anal Training Riding Dildo Util I Cum Sissy Amateur Crossdresser
      Twokisses
      39.1K views
    • sissy anal cumming trainer
      56:50
      sissy anal cumming trainer
      747K views
    • Trans Anal Training with Dildo
      14:31
      Trans Anal Training with Dildo
      Vanniall
      13K views
    • Damazonia & Natalie Mars - Anal Fisting Strapon
      15:55
      Damazonia & Natalie Mars - Anal Fisting Strapon
      291.2K views
    • Fist Bootcamp (Forest Anal Training)
      01:13
      Fist Bootcamp (Forest Anal Training)
      Revenge
      186.5K views
    • Anal training for experienced anal sluts
      27:27
      Anal training for experienced anal sluts
      231.2K views
    • Sissy Haileydoll In Chastity Anal Training And Gapes
      01:12
      Sissy Haileydoll In Chastity Anal Training And Gapes
      Sissy Haileydoll
      71K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Anal Training
      00:52
      Anal Training
      90.2K views
    • You Are Just a Hole - Variety Itsol
      10:46
      You Are Just a Hole - Variety Itsol
      Rodrigo Amor
      1.8M views
    • Asian Sissy Femboy Slave Squirt During Anal Training Session With Machine While Tied Up And Using Chastity Cage
      07:21
      Asian Sissy Femboy Slave Squirt During Anal Training Session With Machine While Tied Up And Using Chastity Cage
      MaureenNadh
      8.9K views
    • Lena Vesper Gets Fisted & Milked by MILF Bane Jane
      01:11
      Lena Vesper Gets Fisted & Milked by MILF Bane Jane
      Snake_0rgy
      149.4K views
    • Femboy Bitch Bubble Butt Anal Training
      07:21
      Femboy Bitch Bubble Butt Anal Training
      Sissy Slut Chantal Sweet
      2.4K views
    • TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
      09:06
      TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
      556.5K views
    • Chastity Sissy Anal Training Jessica Bloom Anal Instructions
      08:23
      Chastity Sissy Anal Training Jessica Bloom Anal Instructions
      Jessica Bloom
      42.6K views
    • Lena Vesper's Milking & Gooning Session
      08:12
      Lena Vesper's Milking & Gooning Session
      Snake_0rgy
      188.9K views
    • Cute Glasses Shemale Anal Training 2
      12:21
      Cute Glasses Shemale Anal Training 2
      MaureenNadh
      84.8K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      749.2K views
    • Asian Shemale Virgin Ass Anal Training and Ass to Mouth
      27:45
      Asian Shemale Virgin Ass Anal Training and Ass to Mouth
      MaureenNadh
      281.8K views
    • fist and foot in ass
      14:08
      fist and foot in ass
      1.6M views
    • Setsunas anal training enjoyment
      08:03
      Setsunas anal training enjoyment
      Setsuna_Iris
      32.7K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      332K views
    • Futa anal training nurse
      00:37
      Futa anal training nurse
      WaifuStuff
      21.5K 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
    • Sissy strapon anal training
      07:47
      Sissy strapon anal training
      Lola Spais
      1.9K views
    • Long Anal Session for Hurting Emma Tied to the Bench
      01:05:06
      Long Anal Session for Hurting Emma Tied to the Bench
      ActorFab
      269.1K views
    • CD Marty got anal training by hard XL cock of tranny
      05:42
      CD Marty got anal training by hard XL cock of tranny
      Marty-Dim69
      10.9K views
    • Real sissy hypnotic
      24:43
      Real sissy hypnotic
      227.5K views
    • Sissy Anal Training Instructions - Fuck your Ass with Me FULL VID on LayneLovee Manyvids
      01:24
      Sissy Anal Training Instructions - Fuck your Ass with Me FULL VID on LayneLovee Manyvids
      Layne Love
      25.5K views
    • anal orgasm training
      10:17
      anal orgasm training
      154.4K views
    • Extreme Anal Training of cute sissy locked in flat metal Chastity Cage riding big BBC dildo!
      05:54
      Extreme Anal Training of cute sissy locked in flat metal Chastity Cage riding big BBC dildo!
      NAT0NYA
      4.4K views
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • Smoking Sissy Anal Training
      02:28
      Smoking Sissy Anal Training
      27.3K views
    • Open Up my Ass and Piss Inside
      02:23
      Open Up my Ass and Piss Inside
      Loren Aprile
      646.3K 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 Anal Training

    • Anal Stretching Training
    • Extreme Insertion
    • Dildo Instruction
    • Prostate Orgasm Tutorial
    • Inserting Everyday Objects Into My Ass
    • Shemale Anal Training
    • Sissy Butt Plug
    • Public Buttplug
    • Farting on Dick
    • Dildoing
    • Analgasm
    • How to Sissygasm
    • Ruined Orgasms
    • Brainwashing
    • Bondage Pegging
    • Ball Torture
    • Inverted Chastity Cage
    • Cum Eating Instructions
    • Free Trap Rule 34
    • Showing Asshole
    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