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

    Sissy First Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Feminization
    First Time
    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
    Sissy Faggot
    Sissy Cum
    Sissy Creampie
    Sissy Humiliation
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      924.6K views
    • I FUCK ON THE FIRST DATE
      07:37
      I FUCK ON THE FIRST DATE
      Third sex XXX
      2.3M views
    • I had my first sex, he came inside me :(
      05:08
      I had my first sex, he came inside me :(
      cd_aysemmm
      109.3K views
    • Skinning her ass with big cock
      01:32:24
      Skinning her ass with big cock
      MundoAmador_
      61.2K 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
      628.4K views
    • Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
      20:30
      Trans Slut With Big Ass Gets Fucked By Trans Beauty - prettyboi2000x
      Prettyboi2000x
      84.6K views
    • Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      18:27
      Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
      Vane03_siss
      217.2K views
    • TS TRAP SISSY DATE HIKE
      06:16
      TS TRAP SISSY DATE HIKE
      1.3M views
    • Sissy Boy Has Prostate Orgasm
      00:46
      Sissy Boy Has Prostate Orgasm
      5M views
    • Thai-Malaysian student cosplay EP2: SisK suck Reina
      06:28
      Thai-Malaysian student cosplay EP2: SisK suck Reina
      SissyKanisa
      1.4M views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      106.2K views
    • Josie Blades First porn with her man
      27:24
      Josie Blades First porn with her man
      Josie Blade
      1.1M views
    • Sissy Femboy Fucked From Behind
      05:20
      Sissy Femboy Fucked From Behind
      2.7M views
    • Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
      07:07
      Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date
      Ria_Bentley
      569.8K views
    • Feminized for Girls Night Out (Full Movie)
      23:39
      Feminized for Girls Night Out (Full Movie)
      Bailey Wilde
      550K views
    • I fuck her ass with desire
      43:32
      I fuck her ass with desire
      World Trany
      55.3K views
    • BBC Fucks a Slutty Crossdresser Without Limits
      32:44
      BBC Fucks a Slutty Crossdresser Without Limits
      Trans and Co
      376.9K views
    • Fisting Double Sissygasm Cumshots
      01:38
      Fisting Double Sissygasm Cumshots
      Lola Spais
      156.4K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      745.4K views
    • 19 years old trans has her first threesome
      10:06
      19 years old trans has her first threesome
      Saranji
      560K views
    • The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      07:20
      The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)
      Sonechka25
      34.9K views
    • BF demolishes my young femboy bussy (2025 Remaster)
      12:36
      BF demolishes my young femboy bussy (2025 Remaster)
      Prettyboi2000x
      64.8K views
    • Best Caged Only orgasms compilation
      06:42
      Best Caged Only orgasms compilation
      boobyb0y
      112.8K views
    • First meeting crossdressing mature sissy
      11:07
      First meeting crossdressing mature sissy
      377.6K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.5M views
    • Femboy Tries His First BBC
      03:36
      Femboy Tries His First BBC
      mothplayboy
      23.3K views
    • why do I suddenly love trannys?
      12:46
      why do I suddenly love trannys?
      1.2M views
    • Feminized Sissy Sluts First Sissygasm With Her Stepmoms Dildo
      00:36
      Feminized Sissy Sluts First Sissygasm With Her Stepmoms Dildo
      ClosetPantyBoy
      464.6K views
    • Completely Submitted and Feminized
      08:12
      Completely Submitted and Feminized
      Pure Ts
      48.6K views
    • Training to become a sissy cuckold
      03:26
      Training to become a sissy cuckold
      amatorxxx
      620.7K views
    • I can't believe i'm posting this! BBC Fucks Sissy
      00:50
      I can't believe i'm posting this! BBC Fucks Sissy
      Sissy Joyce
      440.7K views
    • NEW CUMPILATION, best handsfree orgasms
      05:48
      NEW CUMPILATION, best handsfree orgasms
      boobyb0y
      321.2K views
    • Sissy Accidentally cums while rubbing her clit in the little chastity cage
      01:41
      Sissy Accidentally cums while rubbing her clit in the little chastity cage
      KiraszaSissy
      166.9K views
    • Morgane the trans slut has her first bbc casting
      39:13
      Morgane the trans slut has her first bbc casting
      bijango007
      887K views
    • Video editing session turns into a kinky bi and trans foursome orgy
      40:50
      Video editing session turns into a kinky bi and trans foursome orgy
      Spike Essex
      1.2M views
    • Orgy with the transvestites
      01:00:23
      Orgy with the transvestites
      MundoAmador_
      31.3K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      466.7K views
    • Our First Date
      05:00
      Our First Date
      Cassandra Lovit
      10.6K views
    • Sissy feels cum inside her for the first time
      00:14
      Sissy feels cum inside her for the first time
      Sissy Joyce
      2.3M views
    • POV Night Sister Trans Femboy Blowjob Sexy Eyes Tongue Feet Ass Cum on Tits
      16:56
      POV Night Sister Trans Femboy Blowjob Sexy Eyes Tongue Feet Ass Cum on Tits
      NightSisterLil1
      61.1K views
    • Tgirl Riley offers her little ass in the hallway
      20:16
      Tgirl Riley offers her little ass in the hallway
      Tgirl Riley
      94.1K views
    • He tried a Tgirl blowjob and dont want anything different now
      04:02
      He tried a Tgirl blowjob and dont want anything different now
      Agata Monroe
      21.3K views
    • Sissy Whore Training 3
      19:43
      Sissy Whore Training 3
      cdCrystal
      15.6K views
    • Story of when daddy pimped me out. First week. Anal toy.
      08:50
      Story of when daddy pimped me out. First week. Anal toy.
      Sunaxfemiknulla
      18.3K views
    • I got on Grindr got fucked and had multiple sissygasms
      04:09
      I got on Grindr got fucked and had multiple sissygasms
      OneWhoHasFun
      156.8K views
    • Sissy's first fuck on video
      06:39
      Sissy's first fuck on video
      149.5K views
    • Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      08:12
      Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
      nbnabunny
      1.6M 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 Sissy First

    • Submissive Ladyboy
    • Femboy Fucked
    • Transvestites Sissies
    • Hot Sissy
    • Sissygasm Fuck
    • First Time With Trans
    • Girlfriend Catches Me Crossdressing
    • Straight Guy Tricked
    • Crossdresser Schoolgirl
    • The Sissy's Future
    • Trap Bareback
    • Cross Dressing Faggot
    • Daddy's Girl
    • Sissyslut Harley
    • Trapped
    • Feminize Yourself
    • Male to Female Transformation
    • Feminization Process
    • Inverted Chastity
    • How It Started
    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