PornPorn Transgender • US
  • Live Sex
    -50%
  • Premium Premium Videos
  • Pornstars
  • Channels
Annual Ultimate: 50% OFF Our 10th b’day special

Pain 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
  • The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
    10:53
    The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
    alinanightsky
    307.2K views
  • feminisation training
    09:58
    feminisation training
    I IndirectInitiator50
    520K views
  • 25 min of abuse and hard use for the pain whore Alina
    03:04
    25 min of abuse and hard use for the pain whore Alina
    alinanightsky
    61.6K views
  • CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    AZNSWAGDADDY
    1M views
  • Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
    18:54
    Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
    Denise Humain
    9.8K views
  • anal orgasm training
    10:17
    anal orgasm training
    ayrtonp
    172.6K views
  • Pleasure Pain Sissy
    03:14
    Pleasure Pain Sissy
    m mustesna
    50.6K views
  • Pain Slut Kira
    36:28
    Pain Slut Kira
    Twistedrama
    117.2K views
  • Compilation with Weekly Episodes from the pain whore Alina
    02:05
    Compilation with Weekly Episodes from the pain whore Alina
    alinanightsky
    72.7K views
  • Anal training for experienced anal sluts
    27:27
    Anal training for experienced anal sluts
    T TravonParis
    252.6K views
  • Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
    14:42
    Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
    Denise Humain
    37.1K views
  • ioioioioi
    08:39
    ioioioioi
    K Kondoo
    733.5K views
  • Sissy Denise: Nipple torture with combination pliers – Live until the end
    09:37
    Sissy Denise: Nipple torture with combination pliers – Live until the end
    Denise Humain
    6.6K views
  • Contractions
    08:55
    Contractions
    jeannapotter
    96.3K views
  • A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    01:34
    A desperate trap sissy pain whore asks a top man to take her as a sex slave and let him fuck her throat and ass
    alinanightsky
    46K views
  • Shemale Anatomy
    03:06
    Shemale Anatomy
    3.2M views
  • Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
    13:59
    Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
    Denise Humain
    23.8K views
  • shemale dildo hero - inflatable training
    37:16
    shemale dildo hero - inflatable training
    d dildoheroarchive
    174.8K views
  • A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
    28:23
    A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
    Denise Humain
    14.5K views
  • Sissy Poppers Hypnose Training IV
    20:31
    Sissy Poppers Hypnose Training IV
    bkifft
    173.2K views
  • Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    13:53
    Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
    Denise Humain
    6.1K views
  • training
    07:56
    training
    chastitygurl
    136.4K views
  • Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
    05:13
    Sissy Whores Anal Seduction Comeback: Denise Humain as Pink Lingerie Cumslut – Begging for extreme gangbangs, deepthroat & gaping holes!
    Denise Humain
    5.8K views
  • training
    07:28
    training
    chastitygurl
    158.5K views
  • MissRose TS -Preview BBC GIANT XXXL Dildo Painal Moan Outdoors - Shemale Got Caught Anal Stretching - Big Cock Pumping M
    01:29
    MissRose TS -Preview BBC GIANT XXXL Dildo Painal Moan Outdoors - Shemale Got Caught Anal Stretching - Big Cock Pumping M
    MissRose TS
    21.5K views
  • Sissy training instructional
    17:12
    Sissy training instructional
    g gambit2019
    249.5K views
  • Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    09:57
    Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
    Sadee Rain
    34.7K views
  • Sissy bondage & training
    14:30
    Sissy bondage & training
    387.1K views
  • Resistance Means Pain - Dr Vex Sissy Therapy Training Preview
    03:39
    Resistance Means Pain - Dr Vex Sissy Therapy Training Preview
    Doctor-Vex
    602 views
  • sissy training
    15:28
    sissy training
    sexobjekt
    441.2K views
  • BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    07:34
    BDSM TS Sissy Slave Orgasmic Compilation - Horny Trans Shemales
    Denise_Humain
    7.7K views
  • Cock Craving Whore - Sissy training JOI - Femdom
    08:45
    Cock Craving Whore - Sissy training JOI - Femdom
    puchu3k
    421.3K views
  • sissy dildo trainer - emma
    13:39
    sissy dildo trainer - emma
    d dildoheroarchive
    125.4K views
  • Sissy Brainwashing Training
    13:46
    Sissy Brainwashing Training
    s sguy263
    396.4K views
  • Shemale Cock Addiction - Trainer
    02:55
    Shemale Cock Addiction - Trainer
    1.6M views
  • sadistic sissy boy Lucy with his bound slave
    03:41
    sadistic sissy boy Lucy with his bound slave
    slave Martin
    27.5K views
  • Subs Hard Facefuck Training Against the Wall
    06:36
    Subs Hard Facefuck Training Against the Wall
    johnypto
    409.8K views
  • Sissy Training
    12:38
    Sissy Training
    777K views
  • Gloryhole Cum Slut - Training (unknown PMV artist)
    08:11
    Gloryhole Cum Slut - Training (unknown PMV artist)
    MucBY
    747.5K views
  • Sissy Bitch Trainer
    05:47
    Sissy Bitch Trainer
    s sissies_love_BBC
    321.5K views
  • This is advance training for whatabe Nasti Bitches
    16:47
    This is advance training for whatabe Nasti Bitches
    133cooljakesnake133
    212.5K views
  • Cop's doom
    17:43
    Cop's doom
    J JLash
    214.5K views
  • Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    11:20
    Degraded and bound Alina learns that her pleasure is on the secon place during exhausting bdsm session
    alinanightsky
    371.4K 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
    394.3K 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
    305.1K views
  • sissy training video
    11:54
    sissy training video
    ayrtonp
    189.3K views
  • Trust The Fucking Process
    52:41
    Trust The Fucking Process
    Q Queerfc
    1.2M 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
Black
Shemale Fucks Shemale
Amateur
Shemale Fucks Girl
Sissy
Ladyboy
Guy Fucks Shemale
Blowjob
Compilation
Cum In Mouth
Big Black Cock
Big Ass
Mature
Bareback
Creampie
Cumshot
Homemade
Masturbation
Anal
Teen
Domination
Asian
Solo
BBW
Vintage
Transgender
Brazilian
Interracial
Cartoon
Young
Big Tits
Mexican
Lingerie
Threesome
Small Cock
Japanese
Gangbang
Trans Woman
Thai
BDSM
Colombian
Public
Dildo
Couple
MILF
Anal Masturbation
Petite
Trap
Pretty
Rough Sex
Stockings
POV
Small Tits
Outdoor
Babysitter
Cuckold
Hentai
Handjob
Trans Man
Group Sex
Indian
Fetish
Chinese
Hardcore
Massage
Bondage
English
Nude
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