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

Sissy Bear Porn Videos

4360 Results

Free Videos
Short Videos
Sissy Bear
Premium Videos
Photos
Chastity Sissy
Sissy Lingerie
Sissy Orgasm
Sissy Public
Cute Sissy
Sissy School
French Sissy
Sissy Story
Sissy Mistress
Sissy Swallow
Sissy Whore
Sissy Dominated
Sissy Fisting
Sissy Domination
Sissy Bnwo
Sissy Orgy
Caged Sissies
Sissy Moaning
Sissy Dreams
Sissy CEI
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Sissy Hailey Doll gets her holes ruined by BBC😈
    02:05
    Sissy Hailey Doll gets her holes ruined by BBC😈
    Sissy Haileydoll
    864K views
  • Part 3:-Lanista Bear, Domina Satana takes Frankie in the dungeon fora. good session!
    05:50
    Part 3:-Lanista Bear, Domina Satana takes Frankie in the dungeon fora. good session!
    Aaexperiencesltd
    68.4K views
  • Slamming Sammie
    14:20
    Slamming Sammie
    Justice Trans
    124K views
  • Her ass can fit all my big black cock so good
    06:21
    Her ass can fit all my big black cock so good
    MrNastyXavier
    2.5M views
  • Part 1:- Lanista Bear & Allegro sucking cock in vamp room
    05:34
    Part 1:- Lanista Bear & Allegro sucking cock in vamp room
    Aaexperiencesltd
    56.6K views
  • Breaking in Another Sissy Ass for Your Viewing Pleasure.
    01:12
    Breaking in Another Sissy Ass for Your Viewing Pleasure.
    32.5K views
  • Shemale Anatomy
    03:06
    Shemale Anatomy
    3.6M views
  • Part 2:- Lanista Bear takes Melanie for play time with Bottom Feeder.
    05:55
    Part 2:- Lanista Bear takes Melanie for play time with Bottom Feeder.
    Aaexperiencesltd
    6.7K views
  • Real sissy hypnotic
    24:43
    Real sissy hypnotic
    384.5K views
  • A Pretty Blonde Femboy Fucked in the Kitchen by a Black Guy
    13:45
    A Pretty Blonde Femboy Fucked in the Kitchen by a Black Guy
    Trans and Co
    473.9K views
  • Part 3:- Lanista Bear has Maid Jayne bring in the new sex slave for a test run!
    05:15
    Part 3:- Lanista Bear has Maid Jayne bring in the new sex slave for a test run!
    Aaexperiencesltd
    16.6K views
  • Big dicked Sissy crosdresser trav Riley getting fucked bare by thick uncut dick
    13:50
    Big dicked Sissy crosdresser trav Riley getting fucked bare by thick uncut dick
    Tgirl Riley
    71.6K views
  • Entering the Feminization Academy
    08:12
    Entering the Feminization Academy
    Pure Ts
    221.4K views
  • Part 4:-Lanista Bear, Domina Satana takes Frankie in the dungeon fora. good session!
    05:47
    Part 4:-Lanista Bear, Domina Satana takes Frankie in the dungeon fora. good session!
    Aaexperiencesltd
    44.4K views
  • Sissy Really Pleasure with BBC
    03:57
    Sissy Really Pleasure with BBC
    2.9M views
  • big men big cock
    03:03
    big men big cock
    Shalom70
    1M views
  • Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroasting Cum in Mouth Humiliation Deep Throat BWC
    13:35
    Training Black Sissy Aliza to serve a Big Cock White Daddy Spitroasting Cum in Mouth Humiliation Deep Throat BWC
    Fiona Fortune
    53.8K views
  • Shemale fucked good
    10:01
    Shemale fucked good
    TSLuxylux
    921.2K views
  • Sissy 4: Cum Lover
    10:16
    Sissy 4: Cum Lover
    856.4K views
  • Beautiful Shemale With Huge Tits Surprises Her Friend Masturbating And Ends Up Making Him Cum Hard!
    12:12
    Beautiful Shemale With Huge Tits Surprises Her Friend Masturbating And Ends Up Making Him Cum Hard!
    MarilyDaniela
    2M views
  • HOW TO BE A BETTER SISSY!
    10:42
    HOW TO BE A BETTER SISSY!
    490.5K views
  • Relevant Short videos

    Pretty Gurl
    Pretty Gurl
    Pure Ts
    3K views
    Work Underling Becomes Secret Sissy Fucktoy
    Work Underling Becomes Secret Sissy Fucktoy
    Pure Ts
    3.6K views
    Part 1 - Domina-Satana and Lanista-Bear take me into their Dungeon for the first time | Clip 2
    Part 1 - Domina-Satana and Lanista-Bear take me into their Dungeon for the first time | Clip 2
    Stephanie-Nicole-TV
    3K views
    Meet Sweet Fresh Faced Annabelle!
    Meet Sweet Fresh Faced Annabelle!
    TS-casting Couch
    2.8K views
    Transformative Love
    Transformative Love
    Pure Ts
    3.1K views
    Tough guy turns into the sexiest girl
    Tough guy turns into the sexiest girl
    Pure Ts
    2.6K views
  • Me getting fucked in heels
    13:34
    Me getting fucked in heels
    Johanne95
    1.7M views
  • Sissy Boy3
    33:27
    Sissy Boy3
    2.4M views
  • Sissy Swap Tales Random side Effect
    13:06
    Sissy Swap Tales Random side Effect
    1.9M views
  • Intense Sissy Anal Hypno
    11:54
    Intense Sissy Anal Hypno
    507.6K views
  • Emasculate your mind
    13:52
    Emasculate your mind
    615K views
  • Big Black Cock for Hardcore Anal Domination of a White Sissy
    03:47
    Big Black Cock for Hardcore Anal Domination of a White Sissy
    Trans and Co
    24.2K views
  • Sissy Slut Submits For Daddy
    06:53
    Sissy Slut Submits For Daddy
    Third sex XXX
    1.4M views
  • Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    651.9K views
  • Femboy Venti Moans From Fucking
    07:38
    Femboy Venti Moans From Fucking
    Cailey Katts
    589.8K views
  • Daddy’s lil ragdoll
    05:32
    Daddy’s lil ragdoll
    Kristi-Jo
    208.8K views
  • Sissy Trainer Rus - Feminization Instruction
    05:01
    Sissy Trainer Rus - Feminization Instruction
    513.2K views
  • Sexy Femboi Gets an Injection of Americana
    09:22
    Sexy Femboi Gets an Injection of Americana
    Pure Ts
    71K views
  • Slut femboy hardcore sex anal humiliation
    11:18
    Slut femboy hardcore sex anal humiliation
    Smoker Master
    2.2M views
  • Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    09:55
    Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    Rozebella
    1.6M views
  • Transformative Love
    06:12
    Transformative Love
    Pure Ts
    118.5K views
  • Sissy Hypno Trip # 11
    12:52
    Sissy Hypno Trip # 11
    481.7K views
  • Sissy: A slut documentary
    08:12
    Sissy: A slut documentary
    Brat Perversions
    156.7K views
  • Bound sissy in chastity gets BBC
    07:46
    Bound sissy in chastity gets BBC
    1.2M views
  • Verbal, dominant white daddy pounds Asian femboy
    06:18
    Verbal, dominant white daddy pounds Asian femboy
    631.2K views
  • Sissy gets what she needs
    03:38
    Sissy gets what she needs
    945.3K views
  • Crossdresser Hardcore
    11:15
    Crossdresser Hardcore
    812.4K views
  • Sissy Royale: Royal Sissies Bred Deep in Cum Frenzy by EnbyHalflingBoi
    01:18
    Sissy Royale: Royal Sissies Bred Deep in Cum Frenzy by EnbyHalflingBoi
    EnbyHalflingBoi
    198.6K views
  • Femboy Tries His First BBC
    03:36
    Femboy Tries His First BBC
    mothplayboy
    332.5K views
  • The cute transgender fuck the pillow and suck a big black dick
    11:17
    The cute transgender fuck the pillow and suck a big black dick
    Samantha Sissy World
    468K views
  • Twink femboy gay gets fucked horny by daddy and he wants to be tgirl sissy tranny as a slut
    08:59
    Twink femboy gay gets fucked horny by daddy and he wants to be tgirl sissy tranny as a slut
    Daddy Femboy
    203.5K views
  • Sexy hot naughty Sissy Crossdresser
    10:25
    Sexy hot naughty Sissy Crossdresser
    CindieLove
    966K views
Previous page
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 42
  9. ...
  10. 80
80

Porn Related to Sissy Bear

Old Rimming
Beeg Brazzers
The Cougar Trap
Kinky TS Ladyboy
Sissyslut Jenny
Short Skirt Teen
Smoking Bimbo
Sissy-Boys
Crossdreser Sex
Bad Bitch
Sweet Dollbr
Crossdress Training
Petite Femdom
Scared Sissy
Sisy Boy
Crossboy With Mommy Clothes
Kink Shemale
Sissie
How to Sissify Your Husband
Kimmy Thai
Related Channels
  • #197
    The Crossdresser
    The Crossdresser
  • #280
    Fetish Trans
    Fetish Trans
  • #222
    Rough dildos TS
    Rough dildos TS
  • #199
    Real Tgirls
    Real Tgirls
  • #144
    Crossdressing Amateurs
    Crossdressing Amateurs
  • #329
    my club
    my club
  • #282
    Just for fans
    Just for fans
  • #228
    Skylar Adams xxx
    Skylar Adams xxx
  • View all
Monetize your content
Become a creator
xHamster
  • About us
  • Blog
  • Creator's Blog
  • Advertising
  • xHamster Awards 2025
  • SEO Specialist Job
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
U.S.C. 2257 Notice
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