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

    First Time Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    First Time Amateur
    Amateur First Time
    First Time Blowjob
    First Time CD
    Cd First Time
    Thai First Time
    First Time Dildo
    Trap First Time
    Beautiful First Time
    Husband First Time
    Couple First Time
    First Time Swallow
    Homemade First Time
    First Time Homemade
    First Time POV
    First Time Full
    First Time Bareback
    First Time Handjob
    Straight First Time
    First Time Straight
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • You will never forget your first time with shemale babe Mel
      12:07
      You will never forget your first time with shemale babe Mel
      Tranny Newbies
      1M views
    • 4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
      06:28
      4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
      Crossdresserkitty
      25.3K views
    • Don't do this to me! I do not like it!
      03:01
      Don't do this to me! I do not like it!
      733.2K views
    • Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
      06:24
      Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
      Crossdresserkitty
      5.8K views
    • Man Dressed as Woman and Fucked by Dominatrix
      06:11
      Man Dressed as Woman and Fucked by Dominatrix
      Bailey Wilde
      210.7K views
    • Mom Crossdresser Madison dressing in sexy outfits with thigh high hose stockings and heels and walks around showing off teasing
      08:31
      Mom Crossdresser Madison dressing in sexy outfits with thigh high hose stockings and heels and walks around showing off teasing
      MadisonCD2025
      just added
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.7M views
    • Big Cumshot Cute Ladyboy Legs Hot Green Dress Sexy Body Pretty Style of Cumming
      06:12
      Big Cumshot Cute Ladyboy Legs Hot Green Dress Sexy Body Pretty Style of Cumming
      Crossdresserkitty
      6.9K views
    • My first man
      01:07
      My first man
      Fruk
      128.7K views
    • ladyboy naked in public with pantyhose and sandals very hot ass enjoy her
      10:11
      ladyboy naked in public with pantyhose and sandals very hot ass enjoy her
      Misaelechowski
      8.6K views
    • First timer can't take it at first try, then he takes it all
      02:20
      First timer can't take it at first try, then he takes it all
      1.8M views
    • Friday flaunt
      01:25
      Friday flaunt
      Granttaylor0711
      3.9K views
    • They made him look like a women and dress him up
      52:52
      They made him look like a women and dress him up
      Alfacontent World
      116.6K views
    • Cute trans in public wearing minidress and heels with very hot ass enjoying pleasure
      09:02
      Cute trans in public wearing minidress and heels with very hot ass enjoying pleasure
      Misaelechowski
      5.4K views
    • Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      10:25
      Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      Trans Angels
      9.1M views
    • Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      07:29
      Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      Crossdresserkitty
      10.7K views
    • Magic Mask
      05:11
      Magic Mask
      168.1K views
    • Amateur crossdresser trying on clothes and playing at being a woman.
      04:45
      Amateur crossdresser trying on clothes and playing at being a woman.
      zulo800
      2.6K views
    • Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
      12:33
      Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
      Futanari XXX
      21.3M views
    • Big White Ass Sissy Crossdresser Lady Boy Purple Dress
      06:18
      Big White Ass Sissy Crossdresser Lady Boy Purple Dress
      Crossdresserkitty
      5K views
    • Another straight guy getting tricked by this hot tgirl
      26:17
      Another straight guy getting tricked by this hot tgirl
      1.1M views
    • +18 Youtube Model Crossdresserkitty Sexy Villager Housewife Dress Long Stockings White BBW Femboy
      05:43
      +18 Youtube Model Crossdresserkitty Sexy Villager Housewife Dress Long Stockings White BBW Femboy
      Crossdresserkitty
      9.3K views
    • Indian Best Threesome Sex! Fuck Both of us
      22:48
      Indian Best Threesome Sex! Fuck Both of us
      indianXworld
      22M views
    • Party Mini Dress Sissy White Body Big Ass Big Butt Booty Crossdresser Femboy Lady boy Gay MTF LGBTQ
      05:36
      Party Mini Dress Sissy White Body Big Ass Big Butt Booty Crossdresser Femboy Lady boy Gay MTF LGBTQ
      Crossdresserkitty
      4.4K views
    • Crossdressed lad tricks a new buddy into fucking
      17:48
      Crossdressed lad tricks a new buddy into fucking
      3.5M views
    • Sissy Crossdresser Sexy Dress Big Ass White Gay Boy Lady Boy Sexy Model
      06:09
      Sissy Crossdresser Sexy Dress Big Ass White Gay Boy Lady Boy Sexy Model
      Crossdresserkitty
      8.3K views
    • Feminized for Girls Night Out (Full Movie)
      23:39
      Feminized for Girls Night Out (Full Movie)
      Bailey Wilde
      548.2K views
    • Sizzling Secretary Vibes: Kitty Stuns in a Blue Dress as the Ultimate Femboy Icon!
      06:05
      Sizzling Secretary Vibes: Kitty Stuns in a Blue Dress as the Ultimate Femboy Icon!
      Crossdresserkitty
      8.4K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      777.1K views
    • Sexy ladyboy legs and mini dress with sandals in hot public
      07:44
      Sexy ladyboy legs and mini dress with sandals in hot public
      Misaelechowski
      3.1K views
    • Mommy Holy - JOI CEI - First Time Cum Eating
      11:15
      Mommy Holy - JOI CEI - First Time Cum Eating
      Holy
      141.1K views
    • Nylon Shemale Mini Jeans Dress Sexy Legs Lady Boy Big Butt Big Ass Sissy Crossdresser
      05:56
      Nylon Shemale Mini Jeans Dress Sexy Legs Lady Boy Big Butt Big Ass Sissy Crossdresser
      Crossdresserkitty
      3.3K views
    • 2 femboys with puffy nipples make love
      04:27
      2 femboys with puffy nipples make love
      4M views
    • Sexy ladyboy striptease solo performance hot short dress big ass
      06:39
      Sexy ladyboy striptease solo performance hot short dress big ass
      Crossdresserkitty
      7.6K views
    • SISSY TRANSFORMATION
      11:07
      SISSY TRANSFORMATION
      649.5K views
    • Party Mini Dress Sissy White Body Big Ass Big Butt Booty Crossdresser Femboy Lady boy Gay MTF LGBTQ
      08:13
      Party Mini Dress Sissy White Body Big Ass Big Butt Booty Crossdresser Femboy Lady boy Gay MTF LGBTQ
      Crossdresserkitty
      7.1K views
    • I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
      08:12
      I Fuck a Beautiful 19-year-old Trans Girl with a Big Dick
      barbanegrazponto1onepov
      2.1M views
    • Blue Dress Crossdresser Sexy Slut Sissy Gay Boy Twink Big Butt Booty Ladyboy Femboy Shemale MTF LGBT
      05:26
      Blue Dress Crossdresser Sexy Slut Sissy Gay Boy Twink Big Butt Booty Ladyboy Femboy Shemale MTF LGBT
      Crossdresserkitty
      6.9K views
    • GenderX - TS Hotty Wakes Up & Catches Friend Jerking Off
      12:51
      GenderX - TS Hotty Wakes Up & Catches Friend Jerking Off
      GenderX
      471.4K views
    • Stepsister trying slut dresses in her private room
      06:01
      Stepsister trying slut dresses in her private room
      Crossdresserkitty
      11.4K views
    • Clara sucks and gets fucked by Mister A. in the bedroom
      12:41
      Clara sucks and gets fucked by Mister A. in the bedroom
      ClaraBCBG
      304.7K views
    • Green Sexy Mini House Dress Shemale Big Butt Sissy Trap Big Ass Tranny Booty Crossdresser Lady Boy F
      05:25
      Green Sexy Mini House Dress Shemale Big Butt Sissy Trap Big Ass Tranny Booty Crossdresser Lady Boy F
      Crossdresserkitty
      3.9K views
    • Trans Taking an Anal Virginity
      08:12
      Trans Taking an Anal Virginity
      Mistress Jodie May
      384.7K views
    • Transgender hot pretty ladyboy short dress white body sexy dancer cosplayer model shemale
      05:28
      Transgender hot pretty ladyboy short dress white body sexy dancer cosplayer model shemale
      Crossdresserkitty
      7.4K views
    • Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
      08:12
      Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
      Elizabeth Stewart
      292.3K views
    • Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      05:51
      Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      Crossdresserkitty
      3.5K views
    • Cross Dressing Student and Tutor Playing with Each Other
      08:12
      Cross Dressing Student and Tutor Playing with Each Other
      Crossdressing Amateurs
      298K views
    Previous page
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to First Time Dressing

    • Sexy Trans
    • Bangkok Thailand
    • Miss Present
    • No Panties Under Dress
    • Xnxx
    • 18 Year School Girl
    • Hottest
    • Sleepover With Stepmom
    • Homemade Amateur Lingerie
    • Cute Surprise
    • Pretty Thai Ladyboy
    • Thai First Time
    • Beautiful Innocent Girl
    • Www Xxxxx Com
    • Boy and Older Women
    • Shy Wife Shared
    • Step Brother and Step Sister Fuck
    • Virgin Porn Tube
    • Penis Sticking Out From Dress
    • Xnxx Hot Sex
    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