PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    Sissy Vacation Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Vacation
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Submissive Sissy
    Sissy Femdom
    Sissy Boy
    Sissy Slut
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M 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
      162.6K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M 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
      17.2K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • fucked a guy on vacation 2023 new video
      01:26
      fucked a guy on vacation 2023 new video
      Vlada Almazova
      47.2K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • Pai-chan's Urbex - a Forgotten Lakeside Vacation House
      03:32
      Pai-chan's Urbex - a Forgotten Lakeside Vacation House
      Pai-chan
      1.1K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.1M views
    • Kellystar518 - Summer Crush
      06:53
      Kellystar518 - Summer Crush
      Kellystar518
      9.5K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      798.4K 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
      12.9K views
    • Sissy Femboy Fucked From Behind
      05:20
      Sissy Femboy Fucked From Behind
      2.7M 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
      7.2K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • Spring Invitation to the Strange Vacation House Weekend Show
      06:52
      Spring Invitation to the Strange Vacation House Weekend Show
      Pai-chan
      1.4K views
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.8M views
    • One day vacation in my private hause whith planty lingeries
      33:03
      One day vacation in my private hause whith planty lingeries
      Jos Jos
      3.9K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M views
    • Karma D quality an generous first
      00:39
      Karma D quality an generous first
      Karma Rainbow Smith D
      7.5K views
    • German anal tranny date outdoor on holiday in Mallorca
      17:26
      German anal tranny date outdoor on holiday in Mallorca
      EroCom
      456.6K views
    • young petite thai ladyboy is fucked by older sex tourist
      39:21
      young petite thai ladyboy is fucked by older sex tourist
      Radical Shemale
      2.9M views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.1M views
    • TRANSFIXED - Trans Lesbians Kasey Kei & Bella Joie Assfuck Charming Stranger While On Vacation
      15:33
      TRANSFIXED - Trans Lesbians Kasey Kei & Bella Joie Assfuck Charming Stranger While On Vacation
      Transfixed
      660.2K views
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      341.2K views
    • Chilean guy in vacations Malaysia getting fucked by ladyboy
      25:35
      Chilean guy in vacations Malaysia getting fucked by ladyboy
      Nikki Ladyboys
      1.4M views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      938.3K views
    • Marriend Guy Thai Vacations ass fucked and internet spreaded
      14:42
      Marriend Guy Thai Vacations ass fucked and internet spreaded
      Nikki Ladyboys
      449.4K views
    • Girl forgot to tell her Tinder date that she’s Trans
      07:22
      Girl forgot to tell her Tinder date that she’s Trans
      JsseMontz
      638.7K views
    • Leaked Thailad Vacations married faggot fucked by a Ladyboy
      15:23
      Leaked Thailad Vacations married faggot fucked by a Ladyboy
      Nikki Ladyboys
      863K views
    • Daddy Milks Trans Girl Prostate
      05:06
      Daddy Milks Trans Girl Prostate
      Gray Perrier
      334.2K views
    • Alpine vacation with a Brazilian hung trans: Taking her thick cock balls-deep while worshipping her cum-loaded rod
      07:19
      Alpine vacation with a Brazilian hung trans: Taking her thick cock balls-deep while worshipping her cum-loaded rod
      DotadaSP
      53.5K views
    • INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
      11:38
      INTIMATE SEXTAPE WITH A GORGEOUS FRENCH TRANS WOMAN WHO FUCKS ME AND GETS FILLED
      Maxime horns
      155.1K views
    • Leaked Thai Vacations Fat Fag ass fucked by 2 Ladyboys
      11:50
      Leaked Thai Vacations Fat Fag ass fucked by 2 Ladyboys
      Nikki Ladyboys
      432.7K 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
      2.3M views
    • Straight British Lad on vacation Fuck a Thai Ladyboy
      02:18
      Straight British Lad on vacation Fuck a Thai Ladyboy
      456K views
    • He filled my ass with it, his drips a lot
      07:53
      He filled my ass with it, his drips a lot
      Piou_Sissy
      253.9K views
    • Thailand Vacation: Petite Girl Wants Her Cock In Her Butt, Why Only?
      27:01
      Thailand Vacation: Petite Girl Wants Her Cock In Her Butt, Why Only?
      WatchMomFuckers
      181.9K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      510.2K views
    • Hot couple fuck a ladyboy on vacation in thailand...........
      06:48
      Hot couple fuck a ladyboy on vacation in thailand...........
      253.1K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      750.2K views
    • I flew to Ibiza with a bestie, I was surprised that she had a dick, she fucked me the whole vacation
      08:17
      I flew to Ibiza with a bestie, I was surprised that she had a dick, she fucked me the whole vacation
      mmiilap
      178.6K views
    • Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      01:17
      Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      Allmylinks
      109.8K views
    • My first vacation in Thailand! I meet this beautiful girl but got a surprise! She spoiled me with her cock and I gave her my spe
      21:25
      My first vacation in Thailand! I meet this beautiful girl but got a surprise! She spoiled me with her cock and I gave her my spe
      NCPORNO
      108.1K views
    • Sensual Shower with a Transgender Goddess - Hard Fist Anal & Sucking
      11:15
      Sensual Shower with a Transgender Goddess - Hard Fist Anal & Sucking
      Maxime horns
      139.8K views
    • hotel maid ladyboy is fucked bareback by sex tourist
      54:43
      hotel maid ladyboy is fucked bareback by sex tourist
      Radical Shemale
      352.1K views
    • Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      08:12
      Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      TGIRLPLAYHOUSE
      2.3M 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

    • Twink Barebacked by Trans
    • Femboy Bareback
    • Sissy Crossdresser Showing off Her Ass
    • Beautiful Femboys
    • Dirty Crossdressers Slut
    • Femboy Fucked
    • Teen 18 Anal
    • Perversion Crossdressing
    • Enjoying a Vigorous Buttfucking
    • Sissy Bra and Panties Crossdresser
    • Girly Boy
    • Sissysubkrystal
    • Secret Sissyboy
    • Balls Deep Penetration
    • Femboy Cum While Fucked
    • She Fulfills His Deepest Fantasy
    • Transvestite
    • Crossboy With Mommy Clothes
    • Crossdress Husband Sucking Cock
    • Cute Transgirl
    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