Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
OKTOBERFEST SALE! 🥨🎪 Limited-Time Faphouse Offer!

Shy Sissy Porn Videos

4360 Results

Free Videos
Short Videos
Shy Sissy
Premium Videos
Photos
Sissy
Shy
Sissy Crossdresser
Sissy Training
Sissy Feminization
Sissy Chastity
Sissy BBC
Sissy Husband
Sissy Fucked
Sissy Compilation
Sissy Slave
Sissy Cuckold
Sissy Gangbang
Sissy Blowjob
Sissy Boy
Young Sissy
Femdom Sissy
Sissy Faggot
Sissy Cum
Sissy Creampie
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Sissy Humiliation Dare Game
    11:31
    Sissy Humiliation Dare Game
    Natalie Napoli
    74.4K views
  • i love riding my daddy
    08:47
    i love riding my daddy
    Johanne95
    224.8K views
  • Sissy Mind Alteration Video!
    04:45
    Sissy Mind Alteration Video!
    672.4K views
  • Sissy Alina Obediently Gives Her Master a Blowjob and Deep Throat and Shows Her Fucked Ass
    00:46
    Sissy Alina Obediently Gives Her Master a Blowjob and Deep Throat and Shows Her Fucked Ass
    Disciplinater
    26.8K views
  • Petite ladyboy is shy but kinky
    39:06
    Petite ladyboy is shy but kinky
    Shemale Strokers
    57.7K views
  • Submission Sissy Trainer
    03:23
    Submission Sissy Trainer
    1.4M views
  • Sissy Jenny being used and abused part 2
    23:24
    Sissy Jenny being used and abused part 2
    t terrel345
    194K views
  • Tiny Young and Shy Anri Singer
    16:50
    Tiny Young and Shy Anri Singer
    Shemale Strokers
    395.3K views
  • The Shy
    01:55
    The Shy
    570K views
  • A Sissy's Dream
    06:16
    A Sissy's Dream
    d dingos75
    1.3M views
  • Shy TS Girl Fucks Fleshlight and Cums
    06:57
    Shy TS Girl Fucks Fleshlight and Cums
    Ellie Exx
    42.3K views
  • Sissy 6
    19:29
    Sissy 6
    k kornetobolenskij
    1.6M views
  • Do you want a Femboy - WEL1
    07:14
    Do you want a Femboy - WEL1
    715.3K views
  • Johanne gets barebacked by her daddy
    04:02
    Johanne gets barebacked by her daddy
    Johanne95
    162.3K views
  • Sissy secrets
    09:42
    Sissy secrets
    717.8K views
  • I was asked to upload this tease i made
    01:53
    I was asked to upload this tease i made
    Sanne
    179.1K views
  • Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    softboixladyathena
    891.2K views
  • Just Your Favorite Transgender Sissy Girl Dancing
    00:52
    Just Your Favorite Transgender Sissy Girl Dancing
    Sissy Joyce
    8K views
  • Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    Goldibottsissy
    1.6M views
  • Rented Out by His Mistress
    06:12
    Rented Out by His Mistress
    Pure Ts
    228.8K views
  • Do Not Be Afraid Sissy
    06:12
    Do Not Be Afraid Sissy
    pantycum666
    752.9K views
  • Relevant Short videos

    Closeted, shy, sissy walks on public trail in only her thong and bra. Bubble butt. Missy
    Closeted, shy, sissy walks on public trail in only her thong and bra. Bubble butt. Missy
    Missy123
    1.8K views
    Shy sissy slut does ass to mouth (ATM)
    Shy sissy slut does ass to mouth (ATM)
    Sissy Webcam Whore
    3.3K views
    Shy Sissy Slut in High Heels | Clip 1
    Shy Sissy Slut in High Heels | Clip 1
    Orchidee35
    66 views
    Sissy strokes her huge cock in Nylons
    Sissy strokes her huge cock in Nylons
    FemboySammy
    9.7K views
    Shaky legs but also shaky butt!
    Shaky legs but also shaky butt!
    Lutscherina
    6.4K views
    Closeted shy Sissy cross dresser pulls panties to the side to pee in public
    Closeted shy Sissy cross dresser pulls panties to the side to pee in public
    Missy123
    2.2K views
  • Sissies1
    01:33
    Sissies1
    nylonfunme
    134.4K views
  • Sissy Dressup Party Sissy Joyce & Sasha De Sade
    08:12
    Sissy Dressup Party Sissy Joyce & Sasha De Sade
    Sissy Joyce
    275.8K views
  • Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    742.1K views
  • Sissy Compilation
    26:22
    Sissy Compilation
    IiSlayeriI
    1.7M views
  • Traps and femboys
    11:47
    Traps and femboys
    609.7K views
  • submitting and being a good girl for mommy
    08:31
    submitting and being a good girl for mommy
    Kittykisses96
    28.7K views
  • Submissive sissy struggles
    06:28
    Submissive sissy struggles
    H_Madman
    225.9K views
  • So You Want to Be a Sissy?
    01:12
    So You Want to Be a Sissy?
    Sissy Joyce
    17.2K views
  • Sissy assfucked and whimpering
    05:44
    Sissy assfucked and whimpering
    i iberia12
    155.9K views
  • A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    u useme42
    1.1M views
  • like a girl (xeriom videos)
    05:37
    like a girl (xeriom videos)
    Nachtelf
    433.8K views
  • #SissyHypno #SissyTraining #SissySlut #Sissification
    11:51
    #SissyHypno #SissyTraining #SissySlut #Sissification
    DaniFemboy
    32.1K views
  • Traps Transgirls & Femboys
    56:15
    Traps Transgirls & Femboys
    1M views
  • Sissy Dreams 3
    26:07
    Sissy Dreams 3
    1.6M views
  • SISSY PMV LIST OF THINGS TO TRY
    05:21
    SISSY PMV LIST OF THINGS TO TRY
    367.8K 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
    9.4K views
  • Sissi
    08:33
    Sissi
    330K views
  • Daddy Humiliates Sissy
    08:15
    Daddy Humiliates Sissy
    200.7K views
  • SISSYSTUDENT: BECOMING A SISSY
    11:05
    SISSYSTUDENT: BECOMING A SISSY
    385.5K views
  • Sissy Slut Motel
    58:39
    Sissy Slut Motel
    950.2K views
  • Sissies Exposed Forever
    04:08
    Sissies Exposed Forever
    58.2K views
  • Young sissy
    06:03
    Young sissy
    422.6K views
  • Sissy Maker Oh So Sweet
    06:50
    Sissy Maker Oh So Sweet
    293.6K views
  • Sissy needs a daddy
    07:21
    Sissy needs a daddy
    268.4K views
  • Boy unexpectedly recruited and transformed into a sissy!
    11:27
    Boy unexpectedly recruited and transformed into a sissy!
    sissyboy092
    135.1K views
  • Sissy Maid Testing Buttplugs and Outfits
    08:19
    Sissy Maid Testing Buttplugs and Outfits
    Sissy Joyce
    118.8K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 41
  9. ...
  10. 80
80

Porn Related to Shy Sissy

Sissy First Time
Sissies Being Used
Shy Crossdresser
Scared Sissy
Secret Sissyboy
Sissyfication Process
A Sissy's Dream
Tricked Into Trap
Shy
Perfect Sissy
Crossdressing Story
Sissyboilucy
Sisy Boy
Feminization Story
The Sissy's Future
Sissy-Virgin
Petite Passionate
Feminized and Fucked
Homemade Seduction
Little Sissy
Related Channels
  • #196
    Sissy Instruction
    Sissy Instruction
  • #90
    Becoming Femme
    Becoming Femme
  • #144
    Sissy Princess
    Sissy Princess
  • #5
    Pure Ts
    Pure Ts
  • #257
    Bad Gurlzz Productions
    Bad Gurlzz Productions
  • #138
    Third sex XXX
    Third sex XXX
  • #187
    Kimberhaven
    Kimberhaven
  • #230
    Cumsissy
    Cumsissy
  • 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