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

    First Time Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Bailey Wilde
      317.4K views
    • Trans Tied Anal Creampie Cumfarts and my First Time Fucked by a CUCUMBER
      13:19
      Trans Tied Anal Creampie Cumfarts and my First Time Fucked by a CUCUMBER
      fermerino
      18.6K views
    • The First Time I Put a 7 Cm Hand in My Ass
      06:52
      The First Time I Put a 7 Cm Hand in My Ass
      Dicktrassy dicktrassy
      12.9K views
    • Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time
      04:16
      Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time
      fermerino
      2K views
    • Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
      01:52
      Anal Training. First Time Using Big Dildo. I Give Up, That's Hurt
      MaureenNadh
      38.2K views
    • Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)
      05:24
      Tranny Gwen Tennyson Destroying Her Ass with BBC Fat Dildo for the First Time (round 1)
      fermerino
      979 views
    • Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time
      04:16
      Fucking My Completely Naked Trans Ass with BBC Dildo for the First Time
      fermerino
      1.5K views
    • First time I put a butt plug in my sissy ass on camera
      04:55
      First time I put a butt plug in my sissy ass on camera
      3.5K views
    • Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
      18:40
      Sissy Tries Butt Plug and Chastity For The First Time - Sissy Housewife
      SissyHousewife
      6.6K views
    • Shemale tries hollow anal plug, anal stretcher for the first time
      05:20
      Shemale tries hollow anal plug, anal stretcher for the first time
      Lucas Nathan King
      6.3K views
    • My First Time Taking This Big Cock I Think I Need to Train My Butt More, It Needs to Go Deeper
      02:00
      My First Time Taking This Big Cock I Think I Need to Train My Butt More, It Needs to Go Deeper
      SashaSuxxx
      1.2K views
    • Emily's first time ever with a sex machine
      01:51
      Emily's first time ever with a sex machine
      Emily Evermore
      1.3K views
    • Amateur Asian Ladyboy First Time Anal Training
      14:44
      Amateur Asian Ladyboy First Time Anal Training
      MaureenNadh
      21.5K views
    • First Time Here
      03:00
      First Time Here
      J JujuTV
      463 views
    • First time whipped
      08:44
      First time whipped
      9.9K views
    • Sissy get fucked by sex machine for first time
      14:07
      Sissy get fucked by sex machine for first time
      SissyDaniella
      3.1K views
    • amateur first time homemade solo dildo
      02:50
      amateur first time homemade solo dildo
      9.4K views
    • Couple Fuck and Cum!!!!!
      02:20
      Couple Fuck and Cum!!!!!
      FrinaXXX
      12.7K views
    • Your Goddess and Queen
      11:45
      Your Goddess and Queen
      Natalie Napoli
      3.4K views
    • Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
      06:21
      Sexy sissy in pink lingerie loves playing with her toys. cross dressing femboy fucks ass riding dildo
      Marcus Domes
      13.2K views
    • Transsexual in adult theater pornteufel.tv
      06:01
      Transsexual in adult theater pornteufel.tv
      88.2K views
    • Discrete tops are fun
      01:40
      Discrete tops are fun
      Karma Rainbow Smith D
      13.3K views
    • Trans Slut Gets Fucked in the Hard Ass - Intense Deep Anal
      01:00
      Trans Slut Gets Fucked in the Hard Ass - Intense Deep Anal
      Sexymarghot
      1.6K views
    • Dumb femboy is getting trained
      02:16
      Dumb femboy is getting trained
      Karol Banaszkiewicz
      1.4K views
    • Double Deep Throat Blowjob Training With Olivia with Huge Plastic Dildo
      06:30
      Double Deep Throat Blowjob Training With Olivia with Huge Plastic Dildo
      Asura
      7.8K views
    • Stupid whore Trisha Trash stuffs her asshole with different butt plugs while sucking a massive dildo
      08:11
      Stupid whore Trisha Trash stuffs her asshole with different butt plugs while sucking a massive dildo
      Trisha Trash
      2.1K views
    • Smoking Sissy Anal Training
      02:28
      Smoking Sissy Anal Training
      28K views
    • Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8
      08:12
      Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 8
      Bailey Wilde
      11K views
    • Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
      06:02
      Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
      24K views
    • Night walk at train station and parking lot with fishnet stocking
      03:26
      Night walk at train station and parking lot with fishnet stocking
      Niya_cd
      21.3K views
    • Monisa Fucking a Guy Hard in the Ass Doggy Style
      01:23
      Monisa Fucking a Guy Hard in the Ass Doggy Style
      Monisa Vanboc
      9.2K views
    • Cum for Me Chun Li
      05:13
      Cum for Me Chun Li
      Xalas
      890 views
    • Lovely Sissygasm caged clitty squirting
      06:51
      Lovely Sissygasm caged clitty squirting
      12.4K views
    • 18yo Fucked by Ebony Futa on Beach Trip.
      01:37
      18yo Fucked by Ebony Futa on Beach Trip.
      Sassy Comics
      11K views
    • Trans crossdressing sissy fucks her asshole  toy and talks about how she wishes it was a real cock in her as she runs her little
      06:20
      Trans crossdressing sissy fucks her asshole toy and talks about how she wishes it was a real cock in her as she runs her little
      MadisonCD2025
      just added
    • Who Wants To Come Stretch My Ass With My Legs Spread Wide On My Back
      00:35
      Who Wants To Come Stretch My Ass With My Legs Spread Wide On My Back
      Soloregin
      8.6K views
    • BDSM Anal Games in a Latex Catsuit.
      08:41
      BDSM Anal Games in a Latex Catsuit.
      4SOMEfckHOl
      1.8K views
    • Femboy sissy slut rides a bottle hard
      05:08
      Femboy sissy slut rides a bottle hard
      J JujuTV
      1.2K views
    • Smooth sissy ass dildo fucking and ass gaping
      02:58
      Smooth sissy ass dildo fucking and ass gaping
      Devotanal
      6.2K views
    • sexual halloween black widow
      05:02
      sexual halloween black widow
      13.7K views
    • Out-door thai  walk show prostitute ladyboy EP2
      00:38
      Out-door thai walk show prostitute ladyboy EP2
      Fampfy Nana
      7.7K views
    • What you NEED
      00:53
      What you NEED
      Karma Rainbow Smith D
      13.7K views
    • Anal snake toy - Sissy in heat and horny
      03:00
      Anal snake toy - Sissy in heat and horny
      Ylvis88
      13.1K views
    • Karmaaaa Rainbow Hybrid lol
      00:36
      Karmaaaa Rainbow Hybrid lol
      Karma Rainbow Smith D
      2.6K views
    • It’s Lovely & Warm in There - Her First Fisting Featuring Jasmine Dlight & Mistress Prin
      00:30
      It’s Lovely & Warm in There - Her First Fisting Featuring Jasmine Dlight & Mistress Prin
      Jasmine_dlight
      1.5K views
    • Sissy femboy whore does it herself in the bathroom
      05:27
      Sissy femboy whore does it herself in the bathroom
      J JujuTV
      535 views
    • Sissy CD Samara Coxxx training her pussy some more - riding a dildo
      02:34
      Sissy CD Samara Coxxx training her pussy some more - riding a dildo
      3.9K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80
    Categories
    American
    4K Porn
    HD Videos
    VR Porn
    Shemale Fucks Guy
    Black
    Big Cock
    Shemale Fucks Shemale
    Amateur
    Shemale Fucks Girl
    Sissy
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Big Black Cock
    Cum In Mouth
    Big Ass
    Bareback
    Creampie
    Cumshot
    Mature
    Homemade
    Teen
    Anal
    Masturbation
    Domination
    Asian
    Transgender
    Solo
    BBW
    Brazilian
    Cartoon
    Vintage
    Mexican
    Interracial
    Big Tits
    Young
    Trans Woman
    Japanese
    Threesome
    Lingerie
    Gangbang
    Small Cock
    Thai
    Petite
    Colombian
    BDSM
    MILF
    Public
    Couple
    Rough Sex
    Dildo
    Anal Masturbation
    Stockings
    Babysitter
    POV
    Cuckold
    Small Tits
    Outdoor
    Trans Man
    Handjob
    FTM
    Hentai
    Group Sex
    Indian
    Fetish
    Chinese
    Bondage
    Massage
    Pissing
    Double Penetration
    English
    Anal Toy
    Role Play
    Behind The Scenes
    British
    SFW
    All categories
    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