Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
AWARDS '26 SALE 🏆👑 Stars Shine, Prices Drop

Shy Winn Porn Videos

384 Results

Free Videos
Short Videos
Shy Winn
Premium Videos
Photos
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • HelloLadyBoy Horny Foreigner Gets Big Tit Ladyboy Sex
    11:12
    HelloLadyBoy Horny Foreigner Gets Big Tit Ladyboy Sex
    Hello Ladyboy
    3.7M views
  • The Shy
    01:55
    The Shy
    573.8K views
  • Mejirin - Cum Kissing with a 19-year-old Shy Ladyboy
    02:22
    Mejirin - Cum Kissing with a 19-year-old Shy Ladyboy
    TransFindHer
    167.6K views
  • Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    Goldibottsissy
    1.7M views
  • i love riding my daddy
    08:47
    i love riding my daddy
    Johanne95
    231K 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
  • HelloLadyBoy Big Dick Ladyboy Cums Hard With Foreigner
    11:12
    HelloLadyBoy Big Dick Ladyboy Cums Hard With Foreigner
    Hello Ladyboy
    211.5K 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
    188.8K views
  • Sissy Mind Alteration Video!
    04:45
    Sissy Mind Alteration Video!
    685K views
  • HelloLadyBoy Petite Shy Pretty Ladyboy Gets The Rough Stuff
    33:19
    HelloLadyBoy Petite Shy Pretty Ladyboy Gets The Rough Stuff
    Hello Ladyboy
    356.5K views
  • More TS Shailen
    26:26
    More TS Shailen
    480.8K 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
    382.3K 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
    89.7K views
  • Velma Is Such a Clumsy and Shy Girl
    14:00
    Velma Is Such a Clumsy and Shy Girl
    MadameMorganXXX
    153.5K views
  • Small Penis Surprise With two beautiful trans women
    01:38
    Small Penis Surprise With two beautiful trans women
    Cailey Katts
    588.2K views
  • Petite ladyboy is shy but kinky
    39:06
    Petite ladyboy is shy but kinky
    Shemale Strokers
    60.3K views
  • Shy cd gets first anal
    14:23
    Shy cd gets first anal
    s shonzy
    629.5K views
  • Helloladyboy Skinny Ladyboy Lets Foreigner Pound Her Ass
    11:12
    Helloladyboy Skinny Ladyboy Lets Foreigner Pound Her Ass
    Hello Ladyboy
    222.4K views
  • Filthy Slut PMV
    02:02
    Filthy Slut PMV
    1.4M views
  • Little Clitty Soft & Shy – Please Make Her Happy (Soft Voice)
    02:39
    Little Clitty Soft & Shy – Please Make Her Happy (Soft Voice)
    Man_with_clitty
    13.1K views
  • Relevant Short videos

    I'm shy I promise
    I'm shy I promise
    AcrylicCloud
    17.7K views
    Sissy strokes her huge cock in Nylons
    Sissy strokes her huge cock in Nylons
    FemboySammy
    10K views
    Shaky legs but also shaky butt!
    Shaky legs but also shaky butt!
    Lutscherina
    6.5K views
    This shy, girly boy is so desperate for approval
    This shy, girly boy is so desperate for approval
    adoralee0829
    7.7K 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
    5.5K views
    Just a shorty
    Just a shorty
    Lisa B.
    6.8K views
  • The Ceremony
    18:00
    The Ceremony
    TiffanyWarmer
    180.7K views
  • Vidxxx5
    26:52
    Vidxxx5
    t trucejenner
    86.4K views
  • CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    AZNSWAGDADDY
    1.2M views
  • Trust The Fucking Process
    52:41
    Trust The Fucking Process
    1.5M views
  • 2 cute and shy T-girls
    12:20
    2 cute and shy T-girls
    Latina Tranny
    2.4M views
  • EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    36:39
    EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    f faceofoblivion
    2M 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
    1.5M views
  • The sensual performance of Ava Holt and Viviana Rose
    10:46
    The sensual performance of Ava Holt and Viviana Rose
    AltErotic
    97.9K views
  • Tiny Young and Shy Anri Singer
    16:50
    Tiny Young and Shy Anri Singer
    Shemale Strokers
    397.6K views
  • Shec shem 5 9
    03:07
    Shec shem 5 9
    j juanpericoshec
    143.5K views
  • Gorgeous Nerdy Trans Girl Gets Hard Fucking!
    11:12
    Gorgeous Nerdy Trans Girl Gets Hard Fucking!
    English Psycho
    886.6K 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
    175.7K views
  • Sissy Brainwashing Training
    13:46
    Sissy Brainwashing Training
    451.4K views
  • GROOBYVR - Satisfying One Night The Naughtiest Vi
    03:12
    GROOBYVR - Satisfying One Night The Naughtiest Vi
    Grooby VR
    116.5K views
  • Are You Winning, Hoe? TransAngels
    02:05
    Are You Winning, Hoe? TransAngels
    Trans Angels
    167.2K views
  • Losing my virginity to a TS
    03:53
    Losing my virginity to a TS
    4.6M views
  • Do Not Be Afraid Sissy
    06:12
    Do Not Be Afraid Sissy
    pantycum666
    756.5K views
  • Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    softboixladyathena
    1.1M views
  • Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    softboixladyathena
    898.3K views
  • SissyAline - Limp and Small
    10:29
    SissyAline - Limp and Small
    634.9K views
  • GOON To Your Girlfriend's Girl Cock
    15:06
    GOON To Your Girlfriend's Girl Cock
    Kitty Quinn
    965.1K views
  • shemale Anal young cum Girl Fuck Big Pussy Transgirl cumming teen Ladyboy
    07:45
    shemale Anal young cum Girl Fuck Big Pussy Transgirl cumming teen Ladyboy
    SissyGirlTs
    89.9K views
  • Triple X pt3
    11:38
    Triple X pt3
    386.8K views
  • Head so good I Keep Almost Bussin
    18:38
    Head so good I Keep Almost Bussin
    525.7K views
  • What Her Name Pls! thank
    05:00
    What Her Name Pls! thank
    2.8M views
  • I Kept My Veil On and You Have No Idea What You’re About to See
    05:15
    I Kept My Veil On and You Have No Idea What You’re About to See
    MTFXXXVIDS
    13K 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
Sissy
Blowjob
Big Black Cock
Cum In Mouth
Guy Fucks Shemale
Big Ass
Compilation
Cumshot
Bareback
Mature
Creampie
Anal
Homemade
Masturbation
Teen
Asian
Domination
Solo
BBW
Cartoon
Brazilian
Interracial
Big Tits
Mexican
Japanese
Transgender
Young
Small Cock
Lingerie
Threesome
Gangbang
Vintage
Trans Woman
Thai
Colombian
BDSM
Trap
Couple
Public
MILF
Petite
Anal Masturbation
Dildo
Small Tits
Rough Sex
Stockings
Cuckold
Pretty
Outdoor
Group Sex
POV
Handjob
Babysitter
Trans Man
Indian
Fetish
English
Hentai
Filipina
Ass Licking
Hardcore
Nude
Futanari
Bondage
Chinese
Massage
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