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

    Sissy Boy Dressing 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
    • S1UTTRANSPUP - Sissy Boy in dress enjoys stretching her hole
      10:32
      S1UTTRANSPUP - Sissy Boy in dress enjoys stretching her hole
      S1utTransPup
      494 views
    • Evening ruffle jumpsuit on tranny sissy boy ready for night
      06:37
      Evening ruffle jumpsuit on tranny sissy boy ready for night
      Lakshmi Trans
      6.4K views
    • S1UTTRANSPUP - Sissy Boy in dress stuffs her hole with HUGE ANAL BALLS
      16:25
      S1UTTRANSPUP - Sissy Boy in dress stuffs her hole with HUGE ANAL BALLS
      S1utTransPup
      621 views
    • S1UTTRANSPUP - Sissy Boy in dress fills her hole with BAD DRAGON DILDO
      07:35
      S1UTTRANSPUP - Sissy Boy in dress fills her hole with BAD DRAGON DILDO
      S1utTransPup
      532 views
    • S1UTTRANSPUP - Sissy Boy in dress takes HUGE DILDO
      14:35
      S1UTTRANSPUP - Sissy Boy in dress takes HUGE DILDO
      S1utTransPup
      592 views
    • S1UTTRANSPUP - Sissy boy in dress enjoys taking your 9 inches
      09:07
      S1UTTRANSPUP - Sissy boy in dress enjoys taking your 9 inches
      S1utTransPup
      450 views
    • Priscilla in her Sissy Boy Outfit
      00:54
      Priscilla in her Sissy Boy Outfit
      4.5K views
    • Wife let me wear her clothes and sissygasm
      06:24
      Wife let me wear her clothes and sissygasm
      OneWhoHasFun
      28.3K views
    • boys are brothers and dress up like sissy girls and CUM
      24:54
      boys are brothers and dress up like sissy girls and CUM
      Nikki Ladyboys
      713.8K views
    • Cumming in my Sparkly Blue Leotard Dress
      03:26
      Cumming in my Sparkly Blue Leotard Dress
      KelseyCobalt
      195.8K views
    • Sissy Femboy wears various sexy women clothes
      05:11
      Sissy Femboy wears various sexy women clothes
      35.8K 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
    • Sissy Play
      11:16
      Sissy Play
      Dark Films Trans
      5.1K 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
    • Take off Your Panties and Take Them All in Your Mouth.
      16:50
      Take off Your Panties and Take Them All in Your Mouth.
      violet_bisex
      2.2K views
    • Public Crossdressing... Sissy in very short dresses outside
      05:07
      Public Crossdressing... Sissy in very short dresses outside
      19.4K views
    • Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      08:12
      Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      1.5K views
    • Suck mommies gorgeous clitty - good boy!
      05:40
      Suck mommies gorgeous clitty - good boy!
      Cindy Belfast
      16.6K views
    • Spandexfemboy - Psychodelic Sissy Anal Fuck
      16:26
      Spandexfemboy - Psychodelic Sissy Anal Fuck
      2.7K views
    • sexy outfit and ejaculation on my mirror
      06:44
      sexy outfit and ejaculation on my mirror
      slurpium
      2.8K views
    • Wait, Natasha, I Have an Order.
      16:40
      Wait, Natasha, I Have an Order.
      violet_bisex
      1.4K views
    • Sissy caught on camera using her aunt clothes
      04:27
      Sissy caught on camera using her aunt clothes
      MelanieR
      16.1K views
    • High class Sissy Faggot Jes
      13:39
      High class Sissy Faggot Jes
      Sissy Cindy Slut
      2.1K views
    • Going out with my sexy pink look part 2
      05:59
      Going out with my sexy pink look part 2
      Letany Ponny
      125K views
    • Sexy leopard coat on sexy girl with high heels boots
      03:41
      Sexy leopard coat on sexy girl with high heels boots
      Letany Ponny
      78.2K views
    • Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      07:35
      Big White Sissy Ass Crossdresser Slut Twink Gay Fem Boy Lady Boy Emo Style Flowered Sexy Dress
      Crossdresserkitty
      1.5K views
    • Crossdresser Sissy poses in sexy dresses & skirts
      05:15
      Crossdresser Sissy poses in sexy dresses & skirts
      4.4K views
    • Crossdresser Sissy in very short dresses outside
      05:09
      Crossdresser Sissy in very short dresses outside
      10.7K views
    • Step dad ask me to seduce him
      05:46
      Step dad ask me to seduce him
      Buddy rider
      6.7K views
    • My stepbrother asked me to wear my stepmother's clothes, I did, and he called me a gay boy and laughed :((
      05:07
      My stepbrother asked me to wear my stepmother's clothes, I did, and he called me a gay boy and laughed :((
      cd_aysemmm
      1K views
    • Sissy Kanisa's Fitting Room: Change Clothes to Go to Pe Class
      02:41
      Sissy Kanisa's Fitting Room: Change Clothes to Go to Pe Class
      SissyKanisa
      5.1K views
    • Sissy Kanisa Jerking off with Pink Satin Dress and Lace Glove
      04:54
      Sissy Kanisa Jerking off with Pink Satin Dress and Lace Glove
      SissyKanisa
      1.8K views
    • Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      02:40
      Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      Spandexlover89
      894 views
    • Sissy girl walking in the street in high heels
      01:14
      Sissy girl walking in the street in high heels
      Letany Ponny
      64.6K views
    • 4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
      06:28
      4K Shemale Cute Sissy Crossdresser 3 Hot Dresses White Gay Boy Slut Twink Big Butt Big Ass
      Crossdresserkitty
      25.3K views
    • Spandexfembox - My Anal Alien Dildo in My Sissy Ass
      11:16
      Spandexfembox - My Anal Alien Dildo in My Sissy Ass
      Spandexlover89
      908 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
    • Cosplay  Horny Asuka Evangelion Vibrator Crossdresser Tgirl
      03:13
      Cosplay Horny Asuka Evangelion Vibrator Crossdresser Tgirl
      saxer123
      1.6K views
    • Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      02:40
      Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      554 views
    • Straight boy likes to dress like a girl
      08:20
      Straight boy likes to dress like a girl
      Anaisfeet35
      7.6K views
    • Pizza Delivery Boy Fucks Guy that Paid for Pizza by Dressing as Woman
      01:52
      Pizza Delivery Boy Fucks Guy that Paid for Pizza by Dressing as Woman
      Jake Grand
      14.6K views
    • A Femboy Dressed Up Candy Makes Hot White Body Attract Bad Boys
      07:24
      A Femboy Dressed Up Candy Makes Hot White Body Attract Bad Boys
      Crossdresserkitty
      just added
    • Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
      06:24
      Crossdressing tricks if you don't have a girl dresses don't worry you can make it from your own boy
      Crossdresserkitty
      5.8K views
    • Big cock shemale in black latex outfit fucks a stud in
      08:03
      Big cock shemale in black latex outfit fucks a stud in
      TS Latex
      6.3K views
    • Sissy in Purple Dress Plays with her Vibrator
      08:08
      Sissy in Purple Dress Plays with her Vibrator
      Oolasbf
      7.3K views
    • Sis-k Pinky Chinese Dress Ep1: Get Dress up
      04:55
      Sis-k Pinky Chinese Dress Ep1: Get Dress up
      SissyKanisa
      6.9K views
    • Young Feminine Boy Drssed Up A Woman Dress Off White Big Booty Smooth Feminine Skin
      05:45
      Young Feminine Boy Drssed Up A Woman Dress Off White Big Booty Smooth Feminine Skin
      Crossdresserkitty
      just added
    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 Boy Dressing

    • Crossdresser First Time With a Man
    • Sissy Boy Skirt and Stockings
    • Beautiful Femboy
    • Femboys in Lingerie
    • Crossdressing Homemade
    • Dirty Crossdressers Slut
    • Cross Dressing Faggot
    • Amateur Crossdress
    • Secret Sissyboy
    • Men Dressed as Women
    • Femboi Fucked
    • Feminized Male
    • Crossdresserkitty
    • Femdom Feminization
    • Sissyslut Harley
    • Guy Gets Transformed Into Drag Queen
    • Sissys Get Blacked
    • Schoolgirl Uniform
    • Ladyboy Dress
    • Shemale Miniskirt
    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