Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
HALLOWEEN SALE – 50% OFF! 👻🎃 Limited Time, Big Thrills!

Shy Winn Porn Videos

Ad notice
Free Videos
Short Videos
Shy Winn
Premium Videos
Photos
HD
Full HD
4K
VR
Best Videos
  • HelloLadyBoy Horny Foreigner Gets Big Tit Ladyboy Sex
    11:12
    HelloLadyBoy Horny Foreigner Gets Big Tit Ladyboy Sex
    Hello Ladyboy
    3.9M views
  • The Shy
    01:55
    The Shy
    584.4K views
  • TRANSFIXED - Shy Cis Guy Gets GANGBANGED By 5 BIG DICK TRANS MILFs And His GF! INSANE GROUP SEX ORGY
    15:05
    TRANSFIXED - Shy Cis Guy Gets GANGBANGED By 5 BIG DICK TRANS MILFs And His GF! INSANE GROUP SEX ORGY
    Transfixed
    4.4M views
  • Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.7M views
  • Mejirin - Cum Kissing with a 19-year-old Shy Ladyboy
    02:22
    Mejirin - Cum Kissing with a 19-year-old Shy Ladyboy
    TransFindHer
    195.5K views
  • Sydney Summers and Princess Emmy Give Up On Men
    13:14
    Sydney Summers and Princess Emmy Give Up On Men
    Trans Roommates
    2.2M views
  • i love riding my daddy
    08:47
    i love riding my daddy
    Johanne95
    244.3K views
  • Sissy Mind Alteration Video!
    04:45
    Sissy Mind Alteration Video!
    722.3K views
  • HelloLadyBoy Big Dick Ladyboy Cums Hard With Foreigner
    11:12
    HelloLadyBoy Big Dick Ladyboy Cums Hard With Foreigner
    Hello Ladyboy
    223.6K views
  • Triple X pt1
    42:30
    Triple X pt1
    1.4M views
  • I convince my shy stepsister to get fucked hard in the ass with my big cock while watching
    10:16
    I convince my shy stepsister to get fucked hard in the ass with my big cock while watching
    ROUS
    385.5K views
  • More TS Shailen
    26:26
    More TS Shailen
    497.5K views
  • HelloLadyBoy Petite Shy Pretty Ladyboy Gets The Rough Stuff
    33:19
    HelloLadyBoy Petite Shy Pretty Ladyboy Gets The Rough Stuff
    Hello Ladyboy
    364.7K views
  • You Win Again
    07:34
    You Win Again
    332.1K views
  • You'd fuck her even if you are straight- Don't be shy
    09:51
    You'd fuck her even if you are straight- Don't be shy
    386.8K views
  • Shy cd gets first anal
    14:23
    Shy cd gets first anal
    636K views
  • Helloladyboy Skinny Ladyboy Lets Foreigner Pound Her Ass
    11:12
    Helloladyboy Skinny Ladyboy Lets Foreigner Pound Her Ass
    Hello Ladyboy
    234K views
  • Filthy Slut PMV
    02:02
    Filthy Slut PMV
    1.5M views
  • Petite ladyboy is shy but kinky
    39:06
    Petite ladyboy is shy but kinky
    Shemale Strokers
    64.2K views
  • Small Penis Surprise With two beautiful trans women
    01:38
    Small Penis Surprise With two beautiful trans women
    Cailey Katts
    645.1K views
  • Shy sissy loves bareback
    03:21
    Shy sissy loves bareback
    35.7K views
  • Relevant Short videos

    I'm shy I promise
    I'm shy I promise
    AcrylicCloud
    18.3K views
    Sissy strokes her huge cock in Nylons
    Sissy strokes her huge cock in Nylons
    FemboySammy
    10.5K views
    Shaky legs but also shaky butt!
    Shaky legs but also shaky butt!
    Lutscherina
    6.8K views
    This shy, girly boy is so desperate for approval
    This shy, girly boy is so desperate for approval
    8.1K views
    Okay, I know I’m moving like a goof, and it’s making me shy But hey, I’m trying!
    Okay, I know I’m moving like a goof, and it’s making me shy But hey, I’m trying!
    GojiraCindy
    6K views
    Just a shorty
    Just a shorty
    Lisa B.
    7K views
  • Gorgeous Nerdy Trans Girl Gets Hard Fucking!
    11:12
    Gorgeous Nerdy Trans Girl Gets Hard Fucking!
    English Psycho
    932.5K views
  • CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    1.2M views
  • EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    36:39
    EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    2M views
  • Trust The Fucking Process
    52:41
    Trust The Fucking Process
    1.5M views
  • The Ceremony
    18:00
    The Ceremony
    TiffanyWarmer
    211.7K views
  • Tiny Young and Shy Anri Singer
    16:50
    Tiny Young and Shy Anri Singer
    Shemale Strokers
    405.2K views
  • Little Clitty Soft & Shy – Please Make Her Happy (Soft Voice)
    02:39
    Little Clitty Soft & Shy – Please Make Her Happy (Soft Voice)
    22K views
  • GENDERX FILMS - "I Know A Way To Get Your Vitals Back Down" - Haven Rose
    15:45
    GENDERX FILMS - "I Know A Way To Get Your Vitals Back Down" - Haven Rose
    GenderX
    1.9M views
  • 2 cute and shy T-girls
    12:20
    2 cute and shy T-girls
    Latina Tranny
    2.5M views
  • Sissy Brainwashing Training
    13:46
    Sissy Brainwashing Training
    458.5K views
  • Shec shem 5 9
    03:07
    Shec shem 5 9
    145.8K views
  • Do Not Be Afraid Sissy
    06:12
    Do Not Be Afraid Sissy
    766.5K views
  • Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    922.8K views
  • Losing my virginity to a TS
    03:53
    Losing my virginity to a TS
    4.7M views
  • Vidxxx5
    26:52
    Vidxxx5
    150.6K views
  • Waiting 4 U - Coming Home To Your Horny Trans Girlfriend JOI
    06:44
    Waiting 4 U - Coming Home To Your Horny Trans Girlfriend JOI
    Vanniall
    201.8K views
  • Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    1.1M views
  • Dirty little secret PB
    03:13
    Dirty little secret PB
    403.7K views
  • GENDERX FILMS - Caught Staring - Swim Coach Gets More Than an Eyeful from Kalli Grace
    15:06
    GENDERX FILMS - Caught Staring - Swim Coach Gets More Than an Eyeful from Kalli Grace
    GenderX
    104.9K views
  • Triple X pt3
    11:38
    Triple X pt3
    401.5K views
  • GROOBYVR - Satisfying One Night The Naughtiest Vi
    03:12
    GROOBYVR - Satisfying One Night The Naughtiest Vi
    Grooby VR
    127.1K views
  • Are You Winning, Hoe? TransAngels
    02:05
    Are You Winning, Hoe? TransAngels
    Trans Angels
    178.4K views
  • The sensual performance of Ava Holt and Viviana Rose
    10:46
    The sensual performance of Ava Holt and Viviana Rose
    AltErotic
    184.8K views
  • SissyAline - Limp and Small
    10:29
    SissyAline - Limp and Small
    641.9K views
  • Han S 194
    05:14
    Han S 194
    948.2K views
  • Head so good I Keep Almost Bussin
    18:38
    Head so good I Keep Almost Bussin
    534.1K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 9
9
Categories
American
4K Porn
HD Videos
VR Porn
The Handy
Shemale Fucks Guy
Big Cock
Black
Amateur
Shemale Fucks Shemale
Shemale Fucks Girl
Ladyboy
Blowjob
Sissy
Big Black Cock
Big Ass
Cumshot
Guy Fucks Shemale
Compilation
Cum In Mouth
Bareback
Mature
Anal
Masturbation
Creampie
Teen
Homemade
Domination
Asian
Solo
BBW
Big Tits
Cartoon
Brazilian
Interracial
Japanese
Transgender
Mexican
Young
Small Cock
Lingerie
Gangbang
Threesome
Vintage
Thai
Trans Woman
Colombian
BDSM
Trap
Couple
Dildo
MILF
Public
Petite
Anal Masturbation
Outdoor
Stockings
Rough Sex
Small Tits
Cuckold
Pretty
English
POV
Handjob
Trans Man
Group Sex
Indian
Babysitter
Fetish
Filipina
Hentai
Nude
Ass Licking
Futanari
Hardcore
Massage
Bondage
Chinese
SFW
All recommendations
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