PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Sissy Vacation Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Vacation
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy BBC
    Sissy Chastity
    Sissy Husband
    Sissy Compilation
    Sissy Fucked
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Sissy Slave
    Sissy Boy
    Young Sissy
    Femdom Sissy
    Sissy Slut
    Sissy Faggot
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy identity
      08:50
      Sissy identity
      620.2K views
    • German anal tranny date outdoor on holiday in Mallorca
      17:26
      German anal tranny date outdoor on holiday in Mallorca
      EroCom
      523.7K views
    • Trust The Fucking Process
      52:41
      Trust The Fucking Process
      1M views
    • Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!
      00:43
      Slave for tranny girl! After beach jogging there are sweaty socks and feet for his mouth!
      TV_Helena
      169.9K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      3M views
    • Nylon Sissy Slut Michelle Wake up at the Hotel After a Date on Vacation in Turkey
      01:04:55
      Nylon Sissy Slut Michelle Wake up at the Hotel After a Date on Vacation in Turkey
      Michael Ernandes
      19.6K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      798.2K views
    • fucked a guy on vacation 2023 new video
      01:26
      fucked a guy on vacation 2023 new video
      Vlada Almazova
      48.6K views
    • CD TRAP SISSY EDUCATION TRAINING 101
      01:27:33
      CD TRAP SISSY EDUCATION TRAINING 101
      975.7K views
    • Tranny Cumshot on vacation! Great wet t-shirt number right by the pool!
      01:02
      Tranny Cumshot on vacation! Great wet t-shirt number right by the pool!
      Allmylinks
      7.7K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.4M views
    • ONE OF THE BEST MASTURBATING OUTDOORS SCENE OF ME WHEN NEIGHBORS ARE ON A VACATION I AM GOING OUT NUDE AND PLAYING
      03:51
      ONE OF THE BEST MASTURBATING OUTDOORS SCENE OF ME WHEN NEIGHBORS ARE ON A VACATION I AM GOING OUT NUDE AND PLAYING
      Crossdresserkitty
      13.4K views
    • Submission Sissy Trainer
      03:23
      Submission Sissy Trainer
      1.2M views
    • Kellystar518 - Summer Crush
      06:53
      Kellystar518 - Summer Crush
      Kellystar518
      10K views
    • Sissy #3: Feminize Yourself
      16:07
      Sissy #3: Feminize Yourself
      688.1K views
    • Pai-chan's Urbex - a Forgotten Lakeside Vacation House
      03:32
      Pai-chan's Urbex - a Forgotten Lakeside Vacation House
      Pai-chan
      1.5K views
    • Feminization Positivity Trainer
      03:20
      Feminization Positivity Trainer
      729.8K views
    • Sissy Dreams 3
      26:07
      Sissy Dreams 3
      1.2M views
    • Emasculate your mind
      13:52
      Emasculate your mind
      509.3K views
    • Sissyfication
      43:09
      Sissyfication
      1.1M views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      2.3M views
    • Sissy #2: Becoming A Cock Slut
      15:35
      Sissy #2: Becoming A Cock Slut
      901.3K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.8M views
    • Turned Into A Cock Loving Sissy
      18:35
      Turned Into A Cock Loving Sissy
      845.1K views
    • Sissy  Mind Fuck
      09:35
      Sissy Mind Fuck
      780.6K views
    • Sissy 6
      19:29
      Sissy 6
      1.4M views
    • My wife told me to play this
      11:13
      My wife told me to play this
      997.9K views
    • SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      07:22
      SISSY TEST CHECK HOW NAUGHTY SLUT YOU ARE
      734K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.5M views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.2M views
    • ULTIMATE SISSY TEST
      08:36
      ULTIMATE SISSY TEST
      1.2M views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      1M views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      149.5K views
    • Sissy Mind Alteration Video!
      04:45
      Sissy Mind Alteration Video!
      430.7K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.2M views
    • How to train your sissy ass
      17:41
      How to train your sissy ass
      687.9K views
    • Sissy Jackpot
      18:43
      Sissy Jackpot
      135.2K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      328.5K views
    • ladyboy teen shower with her daddy then eat her ass and suck her
      24:48
      ladyboy teen shower with her daddy then eat her ass and suck her
      HeShexxx
      2.7M views
    • Sissy Boy3
      33:27
      Sissy Boy3
      2M views
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      760.1K views
    • Sissy Feminization
      07:42
      Sissy Feminization
      441.2K views
    • Submit to Daddy sissy trainer
      05:26
      Submit to Daddy sissy trainer
      447.4K views
    • 10 reasons why Shemales are just better
      04:53
      10 reasons why Shemales are just better
      872.8K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      11.3M views
    • The Sissy Test
      17:18
      The Sissy Test
      529.6K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Sissy Vacation

    First Time With Trans Woman
    Femboy Wife
    Sissy Crossdresser and Boyfriend
    Amateur Tranny Fucked
    Caught crossdressing by mom
    Short Skirt Bend Over
    Feminine Boy
    Cross Dresser Sex
    Shemale Striptease Surprise
    Real Family Fucking
    Virgin Anal
    Straight Guys Fantasy
    Homemade Hotel
    Transparent Lingerie Try on Haul
    Unexpected Creampie
    Naked femboys
    Dirty Talking Cock Tease
    She Begs for Cum in Her Ass
    Transgender Taboo Porn
    Beautiful Transvestites
    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