Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Pornstars
  • Channels

Retro Sissy Training 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
  • 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
    477.5K views
  • CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    AZNSWAGDADDY
    1.1M views
  • Girls playing before going out
    47:16
    Girls playing before going out
    Alfacontent World
    259.9K views
  • Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    softboixladyathena
    747.3K views
  • PRETTY EBONY TS JERKOFF COMPILATION
    05:33
    PRETTY EBONY TS JERKOFF COMPILATION
    TWERKINGBOYS
    3.1K views
  • Mrs Lovings Sissy Training
    10:13
    Mrs Lovings Sissy Training
    r rob_admirer
    2.4M views
  • AB105 Christmas Girl's Bondage Party-squiting cumshot
    03:23
    AB105 Christmas Girl's Bondage Party-squiting cumshot
    Abby Kitty
    231.9K views
  • stay limp sissy trainer
    03:37
    stay limp sissy trainer
    251.7K views
  • Sissy 80 day chastity cum
    04:13
    Sissy 80 day chastity cum
    Jess Harper
    93.9K views
  • Ultimate Sissy Fuck Doll Trainer
    07:04
    Ultimate Sissy Fuck Doll Trainer
    Ria_Bentley
    188.2K views
  • Rough fucking high end training with sissy crossdresser
    07:06
    Rough fucking high end training with sissy crossdresser
    Rozebell
    2.1K views
  • Sissy Training
    12:38
    Sissy Training
    778K views
  • AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)
    03:09
    AB085 Lustful Abby Kitty be Master's sissy slave -chastity (Chinese and English subtitles)
    Abby Kitty
    88.6K views
  • Sissy identity
    08:50
    Sissy identity
    S Scenedude
    872.9K views
  • AB104 Sex toy tester surrender  (English subtitles)
    10:17
    AB104 Sex toy tester surrender (English subtitles)
    Abby Kitty
    86K views
  • Submission Sissy Trainer
    03:23
    Submission Sissy Trainer
    1.3M views
  • Retro Sissy Training (Recolored)
    10:42
    Retro Sissy Training (Recolored)
    parisgreen
    119.5K views
  • sissy training
    15:28
    sissy training
    sexobjekt
    441.2K views
  • HA37Bondage maid trained with vibrating anal beads and dildo fuck her! Orgasmic squirting!
    01:29
    HA37Bondage maid trained with vibrating anal beads and dildo fuck her! Orgasmic squirting!
    Shinoda hakumi
    35.9K views
  • Sissy in Training
    01:27:33
    Sissy in Training
    MsMischief
    419.7K views
  • Sissy Kanisa Crossdresser Maid Service Part 2 Dress up
    06:23
    Sissy Kanisa Crossdresser Maid Service Part 2 Dress up
    SissyKanisa
    17.5K views
  • Sissy Mind Alteration Video!
    04:45
    Sissy Mind Alteration Video!
    505.7K views
  • Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR
    22:35
    Lady Alice Compilation 07 Mesmerizing Beautiful (mesmerize Version) View Originals by Subscription 4K Uhd 60 Fps HDR
    Mesmeriza
    26.3K views
  • Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    softboixladyathena
    965.3K views
  • trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039
    15:07
    trailer Mesmeriza 23 02 MOV CINEMA CLIP 321 20240814134325039
    Mesmeriza
    8.7K views
  • Training to become a sissy cuckold
    03:26
    Training to become a sissy cuckold
    amatorxxx
    699K views
  • AB097 Slutty nun degraded Sexual transformation -Edging,squeeze
    03:57
    AB097 Slutty nun degraded Sexual transformation -Edging,squeeze
    Abby Kitty
    24K views
  • sissy training
    39:53
    sissy training
    g goodnb
    167.1K views
  • Lady Alice compilation 07 Mesmerizing Beauty  (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR
    22:35
    Lady Alice compilation 07 Mesmerizing Beauty (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR
    Mesmeriza
    12.5K views
  • Feminization training for white faggot sissy sluts
    05:10
    Feminization training for white faggot sissy sluts
    121.7K views
  • Sissy Kanisa Crossdresser Maid Service Part 3: Fapping Cum in Condom
    07:34
    Sissy Kanisa Crossdresser Maid Service Part 3: Fapping Cum in Condom
    SissyKanisa
    9.3K views
  • Submit to Daddy sissy trainer
    05:26
    Submit to Daddy sissy trainer
    mdmaely
    476.7K views
  • Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    softboixladyathena
    550K views
  • How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    210.1K views
  • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    365K views
  • Sissy chastity training
    08:23
    Sissy chastity training
    A Alexfapb1
    250.4K views
  • Sissy training instructional
    17:12
    Sissy training instructional
    g gambit2019
    250.8K views
  • Sissy Training Volume 9 - Sissy Self-Pleasure
    03:13
    Sissy Training Volume 9 - Sissy Self-Pleasure
    461.5K views
  • TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
    09:06
    TRAIN YOUR SISSY PUSSY, BE A BUTTSLUT
    ayrtonp
    593K views
  • SissyHypno Hard
    04:02
    SissyHypno Hard
    medisosiso4ka
    226.6K views
  • Cocklust sissy trainer
    09:38
    Cocklust sissy trainer
    261.8K views
  • Sissy training for your feminization
    03:56
    Sissy training for your feminization
    Allmylinks
    52.5K views
  • Sissy Training
    12:08
    Sissy Training
    caliguy59
    92.4K views
  • Cock Craving Whore - Sissy training JOI - Femdom
    08:45
    Cock Craving Whore - Sissy training JOI - Femdom
    puchu3k
    423.5K views
  • Sissy Poppers Hypnose Training IV
    20:31
    Sissy Poppers Hypnose Training IV
    bkifft
    175.5K views
  • Feminization Positivity Trainer
    03:20
    Feminization Positivity Trainer
    pantycum666
    766.2K views
  • Sissy bondage & training
    14:30
    Sissy bondage & training
    389K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 41
  9. ...
  10. 80
80
Categories
American
4K Porn
HD Videos
VR Porn
Shemale Fucks Guy
Big Cock
Shemale Fucks Shemale
Black
Amateur
Shemale Fucks Girl
Sissy
Ladyboy
Guy Fucks Shemale
Blowjob
Compilation
Cum In Mouth
Big Black Cock
Big Ass
Creampie
Mature
Cumshot
Bareback
Homemade
Masturbation
Anal
Teen
Domination
Asian
Solo
BBW
Transgender
Vintage
Brazilian
Young
Interracial
Cartoon
Big Tits
Mexican
Lingerie
Threesome
Small Cock
Gangbang
Japanese
Trans Woman
Thai
Pretty
BDSM
Trap
Colombian
Public
Couple
Dildo
Anal Masturbation
Petite
MILF
Rough Sex
Stockings
POV
Outdoor
Small Tits
Babysitter
Cuckold
Hentai
Trans Man
Handjob
Group Sex
Indian
Fetish
Hardcore
Chinese
Massage
Nude
English
Bondage
Pissing
Double Penetration
Webcam
SFW
All recommendations
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