PornPorn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Pornstars
  • Channels
MARCH INTO PLEASURE 🌸✨ 50% OFF – Limited Time!

Sissy Anal Training Porn Videos

Free Videos
Short Videos
Premium Videos
Photos
Sissy
Anal
Training
Sissy Training
Sissy Anal
Anal Sissy
Sissy Anal Training Compilation
Latex Sissy Anal Training
Femdom Anal Training for Sissy Boyfriend
Sissy Crossdresser
Sissy Feminization
Sissy BBC
Sissy Chastity
Sissy Husband
Sissy Compilation
Sissy Fucked
Amateur Sissy
Sissy Blowjob
Sissy Cuckold
Sissy Gangbang
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Trust The Fucking Process
    52:41
    Trust The Fucking Process
    Q Queerfc
    1.1M views
  • SISSYALINE TRAIN YOUR SISSY PUSSY
    09:06
    SISSYALINE TRAIN YOUR SISSY PUSSY
    plutoR
    499.5K views
  • Shemale Anatomy
    03:06
    Shemale Anatomy
    3M views
  • Sissy Dildo Trainer (advanced)
    17:02
    Sissy Dildo Trainer (advanced)
    230.3K views
  • sissy anal cumming trainer
    56:50
    sissy anal cumming trainer
    ayrtonp
    779.7K views
  • You're Straight Right- - Sissy Hypno Training
    03:07
    You're Straight Right- - Sissy Hypno Training
    dave1701a
    963.5K views
  • Sissy Dreams 3
    26:07
    Sissy Dreams 3
    1.3M views
  • Sissy training dreams
    26:14
    Sissy training dreams
    pained_expression
    257.2K views
  • Sissy identity
    08:50
    Sissy identity
    S Scenedude
    720.2K views
  • Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.
    06:11
    Dildo Training for Sissies, Femboys, Anal Sluts and Other Cock-hungry Holes - Ride Your Dildo Full of Passion.
    Sissy Slut Chantal Sweet
    30.6K views
  • Anal training for experienced anal sluts
    27:27
    Anal training for experienced anal sluts
    T TravonParis
    245.6K views
  • My Total Destruction in Pink: Extreme Anal Stretch & Loss of Control
    06:48
    My Total Destruction in Pink: Extreme Anal Stretch & Loss of Control
    Melinda James
    just added
  • Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    softboixladyathena
    927.4K 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
    624.7K views
  • Sissy Mind Alteration Video!
    04:45
    Sissy Mind Alteration Video!
    461.4K views
  • SissyAline - Train your sissy pussy, be a buttslut
    09:06
    SissyAline - Train your sissy pussy, be a buttslut
    A AlineSissyRefugee
    443K views
  • 3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2.6M views
  • Fucked up Butthole
    00:36
    Fucked up Butthole
    1 122859215
    just added
  • Sissy Jackpot
    18:43
    Sissy Jackpot
    D DuncanPinderhughes
    148.8K views
  • Nasty Sissy Gapes Her Thick Ass Hard with Huge Dildo Then Humiliated ATM
    11:45
    Nasty Sissy Gapes Her Thick Ass Hard with Huge Dildo Then Humiliated ATM
    star-power69
    just added
  • Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    softboixladyathena
    533.5K views
  • Fat Ass Redhead Gothic Shemale Anal Gape Destruction with Monster Butt Plug and Huge Dildo
    06:40
    Fat Ass Redhead Gothic Shemale Anal Gape Destruction with Monster Butt Plug and Huge Dildo
    fermerino
    1K views
  • Try something new
    01:00
    Try something new
    slutysissy4bigcock
    384.2K views
  • Petra in virgin white,s
    01:03:39
    Petra in virgin white,s
    PetraTVsletje
    10.6K views
  • Filthy Slut PMV
    02:02
    Filthy Slut PMV
    B BBhamsterxx
    1.2M views
  • Sissy bitch training
    04:02
    Sissy bitch training
    ita_sissywhore
    142.6K views
  • A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    u useme42
    830.7K views
  • Sissygasm, tied to fuck machine with feet in the air
    10:18
    Sissygasm, tied to fuck machine with feet in the air
    D Danania
    671 views
  • sugar Cravsitt Presents: BBC 3
    58:34
    sugar Cravsitt Presents: BBC 3
    2.4M views
  • Sexy Indian Sissy Destroying Her Tight Ass
    07:49
    Sexy Indian Sissy Destroying Her Tight Ass
    Your Toy
    just added
  • Sissy Poppers Trainer 1
    04:07
    Sissy Poppers Trainer 1
    347.2K views
  • Part 3 POV Blowjob and Viber Fucking a Sexy Witch Until Cum
    08:12
    Part 3 POV Blowjob and Viber Fucking a Sexy Witch Until Cum
    Sofi_elfqueen
    just added
  • How to train your sissy ass
    17:41
    How to train your sissy ass
    709.8K views
  • sissy
    10:39
    sissy
    l leadelei
    116.3K 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
    117K views
  • Girl and Trans Double Fuck Cucumber!!!
    01:14
    Girl and Trans Double Fuck Cucumber!!!
    Lola Spais
    1K views
  • sissy training
    39:53
    sissy training
    g goodnb
    152.7K views
  • Sissy Riding a Huge Dildo
    02:20
    Sissy Riding a Huge Dildo
    Annastasia Trap
    835 views
  • anal orgasm training
    10:17
    anal orgasm training
    ayrtonp
    166.1K views
  • Fisted
    07:55
    Fisted
    Aurora_Spreads
    2K views
  • Sissy  Mind Fuck
    09:35
    Sissy Mind Fuck
    puchu3k
    801.6K 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
    373.8K views
  • Guide To Anal Training
    10:59
    Guide To Anal Training
    k krasi_2001
    262.9K views
  • Fucked up Butthole
    00:36
    Fucked up Butthole
    1 122859215
    just added
  • Hot Sissy Compilation
    10:52
    Hot Sissy Compilation
    b bft990
    1.8M views
  • Anal Squirt Mistress Training Sissy Booty
    01:58
    Anal Squirt Mistress Training Sissy Booty
    Lola Spais
    1K views
  • Sissy Trainer 5 - Sissy's Love Toys
    04:13
    Sissy Trainer 5 - Sissy's Love Toys
    B BoundSissySlut
    328.2K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 17
  9. ...
  10. 32
32
Sissy Training
Shemale Sissy Training
Sissy Anal Trainer Instructions
The Ultimate Sissy Trainer
Sissy Motivation Anal Trainer
Sissy Trainer
Shemale Anal Training
Sissy Bitch
Shemale Training
Permanent Sissification
Sissygasm
White Sissies 4 Black Masters
Sissy Humiliated
How to sissygasm
Male to Female Transformation
Femboy Sissification
Extreme BDSM Torture
Ass Trainer
Feminization Training
Sissification Process
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