PornPorn Transgender β€’ US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Shy Shy First Timer Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos

    Did you mean shy shy first time?

    Best Videos
    By clicking the content you will also see an ad. AD
    Bruce Willins and a shy transgender woman anal sex
    07:32
    Bruce Willins and a shy transgender woman anal sex
    Nicole Montero
    25.1K views
    Cute Shy Transgender Maid Getting Hard for Us
    01:20
    Cute Shy Transgender Maid Getting Hard for Us
    GoodNewsMedia
    678 views
    Lisa takes her panties off
    02:22
    Lisa takes her panties off
    Lisa B.
    8.2K views
    Leopard print lingerie tease, stockings heels, leather gloves, pears rubbing her pussy
    01:31
    Leopard print lingerie tease, stockings heels, leather gloves, pears rubbing her pussy
    JessicaXD
    342 views
    Ho HO HO Merry Christmas from a shy trap with small titties
    02:02:51
    Ho HO HO Merry Christmas from a shy trap with small titties
    Latina Tranny
    37.4K views
    Sissythai Taste Her Piss (So Shy and Horny)
    08:18
    Sissythai Taste Her Piss (So Shy and Horny)
    Sissythai
    30.2K views
    Reina Hanno in Rem Cosplay Slow Teasing Trailer
    03:03
    Reina Hanno in Rem Cosplay Slow Teasing Trailer
    Reina Hanno
    39.2K views
    Shy guy blows hot trans woman
    10:07
    Shy guy blows hot trans woman
    Tranny Bizarre
    9.8K views
    Lisa plays with her tiny dick
    01:25
    Lisa plays with her tiny dick
    Lisa B.
    8.4K views
    Ruby Stars cute girl, a little bit naughty but heavenly. Shy blonde teen girl first time on webcam kissing a pink dildo.
    16:34
    Ruby Stars cute girl, a little bit naughty but heavenly. Shy blonde teen girl first time on webcam kissing a pink dildo.
    Ruby Stars
    12.3K views
    Star Pheriphery [ Futanari Hentai Game ] Ep.35 First Blowjob for a Shy Giant Futa Cock!
    04:28
    Star Pheriphery [ Futanari Hentai Game ] Ep.35 First Blowjob for a Shy Giant Futa Cock!
    CumInGaming
    559 views
    Super cute teenager tgirl doing a sissy show very shy
    02:54:52
    Super cute teenager tgirl doing a sissy show very shy
    Nicole Montero
    35.2K views
    Lisa meets Mr. Cucumber
    00:52
    Lisa meets Mr. Cucumber
    Lisa B.
    6.2K views
    Gloves ️masturbation
    01:47
    Gloves ️masturbation
    JessicaXD
    538 views
    Shemale hooker handle shy client
    08:53
    Shemale hooker handle shy client
    11.6K views
    I'm wearing an Astolfo swim suit cosplay showing off my hard cock
    02:21
    I'm wearing an Astolfo swim suit cosplay showing off my hard cock
    LalaThePala
    8.1K views
    From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!
    05:13
    From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!
    Crossdresserkitty
    7.9K views
    Shy CD Lynda trying to be sexy
    01:26
    Shy CD Lynda trying to be sexy
    21.3K views
    Very shy tgirl Cinderella with small tits and an uncut cock
    44:36
    Very shy tgirl Cinderella with small tits and an uncut cock
    Latina Tranny
    32.2K views
    Let's masturbate in my room
    01:13
    Let's masturbate in my room
    JessicaXD
    415 views

    Relevant Short videos

    Im jus a shy sissy looking for a daddy
    Im jus a shy sissy looking for a daddy
    gaytwinkkboyyy
    17.4K views
    I'm shy I promise
    I'm shy I promise
    AcrylicCloud
    12.5K views
    Sissy strokes her huge cock in Nylons
    Sissy strokes her huge cock in Nylons
    FemboySammy
    5.2K views
    Pink hair sissy Makizza dancing
    Pink hair sissy Makizza dancing
    Makizza
    7.6K views
    Shaky legs but also shaky butt!
    Shaky legs but also shaky butt!
    Lutscherina
    3K views
    Just a shorty
    Just a shorty
    Lisa B.
    4K views
    Very shy ladyboy with a golf sweater masturbating her dick
    33:47
    Very shy ladyboy with a golf sweater masturbating her dick
    Nikki Ladyboys
    22.1K views
    Shy Post Op Ladyboy Glass Toy Play
    06:13
    Shy Post Op Ladyboy Glass Toy Play
    Ladyboy Pussy
    54.7K views
    Sissy in Nightie Stretches Her Asshole
    02:32
    Sissy in Nightie Stretches Her Asshole
    Elise Woods
    4.1K views
    Shy Ladyboy Teen Zaza Pushing Finger Into Her Ass
    06:13
    Shy Ladyboy Teen Zaza Pushing Finger Into Her Ass
    Ladyboy Gold
    85.6K views
    Shy Girl Evelina Shows Her Shaved Hard Clit
    06:50
    Shy Girl Evelina Shows Her Shaved Hard Clit
    Evelina Trojan
    84.6K views
    She is a very shy European Trap playing with her dick
    46:35
    She is a very shy European Trap playing with her dick
    Latina Tranny
    36.2K views
    Tina - for the first time all naked...and shy !
    02:51
    Tina - for the first time all naked...and shy !
    23.7K views
    Shy tranny Lisa B. wearing sexy outfits
    04:05
    Shy tranny Lisa B. wearing sexy outfits
    Lisa B.
    4.1K views
    Shy but tempting, solo trans soft fantasy
    01:11:05
    Shy but tempting, solo trans soft fantasy
    Reynaldo6
    414 views
    Super cute and shy Asian Ladyboy goes shopping flashing it
    07:10
    Super cute and shy Asian Ladyboy goes shopping flashing it
    Nikki Ladyboys
    71.6K views
    Shy submissive slut Rikki Ryder playing on cam
    22:59
    Shy submissive slut Rikki Ryder playing on cam
    19.4K views
    Shy femboy shows off his big cock
    02:49
    Shy femboy shows off his big cock
    Sony4mony
    12.7K views
    Shy Ladyboy Fat Ass Rimming
    06:11
    Shy Ladyboy Fat Ass Rimming
    Ladyboys Fucked Bareback
    33K views
    Latex and Lingerie - Feeling horny af
    01:00
    Latex and Lingerie - Feeling horny af
    JessicaXD
    457 views
    From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!
    06:03
    From Shy to Slay: Crossdresser Kitty's Personal Transformation Stories!
    Crossdresserkitty
    4.4K views
    Ho HO HO Merry Christmas from a shy trap celebrating xmas
    01:21:01
    Ho HO HO Merry Christmas from a shy trap celebrating xmas
    Latina Tranny
    29.5K views
    Shy tgirl being fucked while another one narrates - part II
    00:25
    Shy tgirl being fucked while another one narrates - part II
    11.6K views
    Shy Ladyboy Big Cock Blowjob
    06:11
    Shy Ladyboy Big Cock Blowjob
    Ladyboys Fucked Bareback
    47K views
    Camera shy tranny posing behind the scenes
    06:03
    Camera shy tranny posing behind the scenes
    Trans 500
    45.4K views
    Natascha Diashow Vol.1 πŸ’œ .
    13:45
    Natascha Diashow Vol.1 πŸ’œ .
    Natascha85
    4.6K views
    Pink stocking on a shy tranny
    01:24
    Pink stocking on a shy tranny
    Lisa B.
    1.9K views
    Cute Amateur Webcam Teen bate
    26:25
    Cute Amateur Webcam Teen bate
    Bluerivercuteteen18
    1.6K views
    She is a very shy Ladyboy trying to make money online
    01:20:42
    She is a very shy Ladyboy trying to make money online
    Latina Tranny
    30.8K views
    Lisa B. Compilation sexy pictures
    01:24
    Lisa B. Compilation sexy pictures
    Lisa B.
    7.6K views
    Shy Shiny Latex Sissy Panty Masturbation And Cum
    06:38
    Shy Shiny Latex Sissy Panty Masturbation And Cum
    J JessikaDoll
    3.9K views
    Shy elf dancing until fuck her tiny hole
    02:08
    Shy elf dancing until fuck her tiny hole
    Sofi_elfqueen
    2.9K views
    Super shy femboy gives a dildo a footjob, handjob, legjob, thighjob, then frots with it
    06:44
    Super shy femboy gives a dildo a footjob, handjob, legjob, thighjob, then frots with it
    xxNeptunian_Chargerxx
    2.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next
    xHamster
    • Press
    • 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
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Π‘ontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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