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

    First Time Sissy Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    4K
    HD
    Full HD
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • 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
      5.6K views
    • First Time Anal
      08:41
      First Time Anal
      Pure Ts
      81.1K views
    • First Time Feminized Means First Time Fucked in the Ass
      12:21
      First Time Feminized Means First Time Fucked in the Ass
      Bailey Wilde
      88.5K views
    • Sissy Training After First Time Feminization
      12:20
      Sissy Training After First Time Feminization
      Bailey Wilde
      300.8K views
    • sissy first-time anal orgasm
      01:25
      sissy first-time anal orgasm
      Pinkyfoot
      46.5K 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
      9K views
    • skinny teen femboy getting fucked first time
      08:12
      skinny teen femboy getting fucked first time
      Fembaby
      26.2K views
    • Guy Decides to Dress as Woman for the First Time
      02:21
      Guy Decides to Dress as Woman for the First Time
      Bailey Wilde
      4.1K views
    • Crossdresser Feminized and Fucked for First Time - VERY TIGHT
      01:08
      Crossdresser Feminized and Fucked for First Time - VERY TIGHT
      Bailey Wilde
      11.5K views
    • Caged sissy crossdresser tries on a BBC dildo for the first time Part I
      01:59
      Caged sissy crossdresser tries on a BBC dildo for the first time Part I
      Julie Spiegel
      6.6K views
    • Roommate Feminized and in Chastity for First Time for Girls Night Out
      01:50
      Roommate Feminized and in Chastity for First Time for Girls Night Out
      Bailey Wilde
      7.6K views
    • First Time Frat Boy College Student Fucks Trans Woman in Chastity
      01:53
      First Time Frat Boy College Student Fucks Trans Woman in Chastity
      Jake Grand
      29.7K views
    • Guy Decides to Dress in Drag for the First Time
      02:20
      Guy Decides to Dress in Drag for the First Time
      Bailey Wilde
      3.3K views
    • Virgin Sissy Housewife Fucked with Dildo for the First Time
      12:44
      Virgin Sissy Housewife Fucked with Dildo for the First Time
      SissyHousewife
      3K views
    • My First Time with a Shemale: a Raw and Passionate Audio Journey
      00:32
      My First Time with a Shemale: a Raw and Passionate Audio Journey
      Kathai Neram
      1.1K views
    • First Time Rapper Fucks Hot TS in Chastity
      01:41
      First Time Rapper Fucks Hot TS in Chastity
      Jake Grand
      4.6K views
    • First Time Shaggy Fucks a Trans Woman
      01:25
      First Time Shaggy Fucks a Trans Woman
      Jake Grand
      12.2K views
    • Guy Feminized and Strapon Fucked for First Time
      00:49
      Guy Feminized and Strapon Fucked for First Time
      Bailey Wilde
      3.4K views
    • First time being a sissy slut in public
      05:41
      First time being a sissy slut in public
      Christina Taylor
      10.7K views
    • First Time Squirt
      05:07
      First Time Squirt
      Aashna
      4.5K views
    • First time completely riding this 20x5cm Dildo! And some Selffisting!
      01:16
      First time completely riding this 20x5cm Dildo! And some Selffisting!
      Wormhole94
      1.6K views
    • Shaggy Fucks a Crossdresser for the First Time
      01:26
      Shaggy Fucks a Crossdresser for the First Time
      Jake Grand
      4.5K views
    • First Time Rapper Fucks Transgender in Chastity
      02:19
      First Time Rapper Fucks Transgender in Chastity
      Jake Grand
      2.7K views
    • First Time Rapper Fucks Hot Transgender in Chastity
      02:13
      First Time Rapper Fucks Hot Transgender in Chastity
      Jake Grand
      2.3K views
    • First Time Rapper Fucks Tgirl in Chastity
      02:11
      First Time Rapper Fucks Tgirl in Chastity
      Jake Grand
      2.4K views
    • First Time Rapper Fucks TS in Chastity
      01:41
      First Time Rapper Fucks TS in Chastity
      Jake Grand
      1.8K views
    • Trans Taking an Anal Virginity
      08:12
      Trans Taking an Anal Virginity
      Mistress Jodie May
      389.1K views
    • I had my first sex, he came inside me :(
      05:08
      I had my first sex, he came inside me :(
      cd_aysemmm
      112.3K views
    • trans girl rides triple cock dildo - Hankey’s Toys Three Amigos
      02:24
      trans girl rides triple cock dildo - Hankey’s Toys Three Amigos
      amyy_babyy_x
      178.4K views
    • Kinky X Mas Sissy Slut - Santas little Slut - Big Bells - Big Balls - Big Cock - Condom Pee Orgasm
      11:44
      Kinky X Mas Sissy Slut - Santas little Slut - Big Bells - Big Balls - Big Cock - Condom Pee Orgasm
      Sissy Slut Chantal Sweet
      4.2K views
    • Chantal Sweet - Chapter 1 - The Foreplay - Let's Make Your Cock Beautiful Hard Baby.
      06:21
      Chantal Sweet - Chapter 1 - The Foreplay - Let's Make Your Cock Beautiful Hard Baby.
      Sissy Slut Chantal Sweet
      2.1K views
    • Karla loves to feel a delicious cock inside her tight ass
      09:59
      Karla loves to feel a delicious cock inside her tight ass
      PalmasRecordsMen
      85.5K views
    • Chantal Sweet - Chapter 2 - Cute German Sissy Bounce her Bubble Butt on Huge Cocks
      06:35
      Chantal Sweet - Chapter 2 - Cute German Sissy Bounce her Bubble Butt on Huge Cocks
      Sissy Slut Chantal Sweet
      1.6K views
    • Crossdresser looking for BWC Daddy's
      05:54
      Crossdresser looking for BWC Daddy's
      Lexion onit
      1.6K views
    • Diva bitch-300 lovers in the future after this long wait!lol
      05:02
      Diva bitch-300 lovers in the future after this long wait!lol
      Karma Rainbow Smith D
      81.5K views
    • Sexy sexy sexy
      06:14
      Sexy sexy sexy
      Karma Rainbow Smith D
      41.6K views
    • My first and in my mouth.
      08:38
      My first and in my mouth.
      Veronika37vera
      18.8K views
    • A Shemale's First Experience with a Man - English Audio Sex Story
      00:32
      A Shemale's First Experience with a Man - English Audio Sex Story
      Kathai Neram
      1.3K views
    • Picky bitch
      02:09
      Picky bitch
      Karma Rainbow Smith D
      20.7K views
    • Indian shemale Masturbation
      05:11
      Indian shemale Masturbation
      ShahinTS
      7.6K views
    • Crossdresser Magic: Pretty Looks, Smooth Skin, and a Touch of Dragon Fantasy
      05:16
      Crossdresser Magic: Pretty Looks, Smooth Skin, and a Touch of Dragon Fantasy
      Crossdresserkitty
      8.2K views
    • CUMSHOT WHEN SEXTING WITH LIVE WEBCAM CHATTING HOT BOOTY BIG ASS SMOOTH SKIN MODEL CROSSDRESSER PORN
      07:29
      CUMSHOT WHEN SEXTING WITH LIVE WEBCAM CHATTING HOT BOOTY BIG ASS SMOOTH SKIN MODEL CROSSDRESSER PORN
      Crossdresserkitty
      7.7K 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
    • 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
    • The opening of my hole and the pleasure as I go inside
      05:26
      The opening of my hole and the pleasure as I go inside
      Yolanthe
      3.2K views
    • Dick
      00:56
      Dick
      Karma Rainbow Smith D
      6.5K views
    • A Ssolo Trans Male Enjoy small and BIG Dildo Ends Up Gaping His Ass.
      05:21
      A Ssolo Trans Male Enjoy small and BIG Dildo Ends Up Gaping His Ass.
      Assexploringmachin
      4.1K 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 First Time Sissy

    • First Time Being Fucked as Crossdresser
    • Daddy Fucking Sissy Femboy
    • Secret Sissyboy
    • Crossdressing Homemade
    • Straight Guy Tricked
    • Fuck Me and Cum Inside Me
    • A Pretty Boy Gets Feminized
    • Sissy-Virgin
    • Giving Him an Experience
    • Real Virgin
    • Cute Traps for Straight Guys
    • Crossdreser Sex
    • Dirty Crossdressers Slut
    • Femboygirlfriend
    • Trap Bareback
    • Feminine Boys
    • Amateur Crossdress
    • Beautiful Femboys
    • Please Stop
    • Transgender Homemade
    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