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

    First Time Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Dress
    Time
    First
    First Time
    First Time Dressed
    First Time Trans
    Shemale First Time
    Sissy First Time
    First Time Cum
    First Time Sex
    First Time Crossdresser
    Ts First Time
    Tranny First Time
    Ladyboy First Time
    First Time Anal
    First Time BBC
    Femboy First Time
    First Time Mature
    First Time Creampie
    First Time Lesbian
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3M views
    • Young sissy first time dressing
      00:47
      Young sissy first time dressing
      5.2K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • First time dressing
      02:13
      First time dressing
      21.7K views
    • My stepmom is a tranny
      16:46
      My stepmom is a tranny
      Combat zone transsexual barebacking
      1.1M views
    • First time dressing up
      04:44
      First time dressing up
      1.8K 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
      637.7K views
    • Crossdresser's First Time Dressed as Woman
      00:41
      Crossdresser's First Time Dressed as Woman
      Bailey Wilde
      65.6K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M 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
    • Guy gets fooled into sex with a shemale
      06:15
      Guy gets fooled into sex with a shemale
      Love4TS
      2.6M views
    • Becoming a sissy Crossdressing When nobody is home (Angel Rios's First time on cam).
      02:48
      Becoming a sissy Crossdressing When nobody is home (Angel Rios's First time on cam).
      Angel Rios
      7.8K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M 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
    • Crossdresser shop owner gets fucked by a man in the shop
      13:00
      Crossdresser shop owner gets fucked by a man in the shop
      WanidaCrossdresser
      346.8K views
    • I Receive New Boots and Walk in Them for the First Time
      01:10
      I Receive New Boots and Walk in Them for the First Time
      MicziCD
      9.6K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.1M views
    • Alexa Cosmic transgirl swimming in the sea first time in teal combi dress
      04:22
      Alexa Cosmic transgirl swimming in the sea first time in teal combi dress
      Alexa Cosmic
      12K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      934.6K views
    • First time dressed losing my anal virginity
      00:11
      First time dressed losing my anal virginity
      125.7K views
    • surprise she has dick
      07:34
      surprise she has dick
      255.4K views
    • First time driving dressed
      02:01
      First time driving dressed
      3.1K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      292.2K views
    • First time cross dressing (and I love it)
      01:19
      First time cross dressing (and I love it)
      kekesissy
      15.8K views
    • I am going to make you my little sissy anal slut
      12:42
      I am going to make you my little sissy anal slut
      Sissy Instruction
      121.2K views
    • first time in clothes
      04:17
      first time in clothes
      7.9K 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
    • TGIRLBBW: DEBUTING LETHE OBLIVA!
      03:11
      TGIRLBBW: DEBUTING LETHE OBLIVA!
      Tgirl BBW
      177.6K views
    • FEMBOYISH - Mischievous Petite Femboy In Lingerie Cyrus Stark Teases Horny Roommate Drake Von
      12:31
      FEMBOYISH - Mischievous Petite Femboy In Lingerie Cyrus Stark Teases Horny Roommate Drake Von
      ADULTTIMEGAY
      594.5K 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
      6.2K views
    • Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      08:16
      Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      Elizabeth Stewart
      403.1K views
    • Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      05:32
      Beril, who combines with her lover for a date, has a hard time deciding what to wear.
      Usaberilx
      5.1K views
    • I came from college and daddy was waiting for me
      06:57
      I came from college and daddy was waiting for me
      Sebnem
      406.2K views
    • T Gurl Cums in her dress
      21:03
      T Gurl Cums in her dress
      61.5K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      693.8K views
    • Trans Verbal Demands   -Elegant Look With Glove And Sweet Dress
      13:00
      Trans Verbal Demands -Elegant Look With Glove And Sweet Dress
      Syn Thetic
      68.5K views
    • He Tears His Cute Trans Roommate's Pantyhose To Bang Her
      10:54
      He Tears His Cute Trans Roommate's Pantyhose To Bang Her
      Devils tgirls
      6.1M views
    • Asian femboy seeking attention in short dress
      05:06
      Asian femboy seeking attention in short dress
      Niya_cd
      10K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
      05:26
      Big Butt Booty Slut Crossdresser Sissy Gay White Ass Sexy Dress
      Crossdresserkitty
      81K views
    • I was about to have a happy married life, but I got Fuck by a stranger before marriage.
      18:34
      I was about to have a happy married life, but I got Fuck by a stranger before marriage.
      WanidaCrossdresser
      301.7K views
    • Step dad ask me to seduce him
      05:46
      Step dad ask me to seduce him
      Buddy rider
      6.7K views
    • Hostel Surprise
      37:09
      Hostel Surprise
      3.1M views
    • White nylon Fantasy in blue polka dress
      06:32
      White nylon Fantasy in blue polka dress
      MTFXXXVIDS
      2K views
    • Hot T GIRL with college boy.
      29:02
      Hot T GIRL with college boy.
      2.9M views
    • Compilation of Crossdressing CD Madison who loves to dress slutty and crossdress
      07:10
      Compilation of Crossdressing CD Madison who loves to dress slutty and crossdress
      MadisonCD2025
      612 views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M 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 Dressing

    • First Time Dressed
    • Step Sister Fucked Hard
    • I Fuck My Stepsister
    • Beautiful Trans
    • Virgin Girl First Time
    • Welcome
    • Xxx Com
    • First Time Full
    • Transgender Family
    • Trans Threesome
    • Sexy Trans
    • 18 XXX
    • First Timer
    • 18 Year School Girl
    • Stepdaughter
    • Beautiful Dick
    • Thailand Street
    • Family Fucking Family
    • Bangkok Thailand
    • Xnxx
    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