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
    Sissy Cuckold
    Sissy Femdom
    Sissy Slut
    Sissy Faggot
    Submissive Sissy
    Sissy Cum
    Sissy Creampie
    Sissy Anal
    Sissy Humiliation
    Beautiful Sissy Boy
    Sissy Caption
    Asian Sissy
    Sissy Trainer
    Sissy Bondage
    Homemade Sissy
    Sissy JOI
    Sissy BDSM
    Sissy Pegging
    Transvestites Sissies
    Sissy Femboy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Two Sissy Slut play sexual games
      15:33
      Two Sissy Slut play sexual games
      IskraElectrical49
      151K views
    • Sissy caught on camera using her aunt clothes
      04:27
      Sissy caught on camera using her aunt clothes
      MelanieR
      16.1K views
    • Magic Mask
      05:11
      Magic Mask
      169.2K views
    • High class Sissy Faggot Jes
      13:39
      High class Sissy Faggot Jes
      Sissy Cindy Slut
      2.3K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M 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
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      64K 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
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      247.1K views
    • White boy dressed like a Girl
      07:07
      White boy dressed like a Girl
      Jade Rain
      2.7K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M 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
    • Many crossdressers fucked scrnrs
      01:09:02
      Many crossdressers fucked scrnrs
      1.4M views
    • Crossdresser Sissy poses in sexy dresses & skirts
      05:15
      Crossdresser Sissy poses in sexy dresses & skirts
      4.4K views
    • Dress Up Sissy Costume Tasks
      10:49
      Dress Up Sissy Costume Tasks
      Natalie Napoli
      23.5K views
    • Crossdresser Sissy in very short dresses outside
      05:09
      Crossdresser Sissy in very short dresses outside
      10.7K views
    • My stepmom is a tranny
      16:46
      My stepmom is a tranny
      Combat zone transsexual barebacking
      1.1M views
    • Step dad ask me to seduce him
      05:46
      Step dad ask me to seduce him
      Buddy rider
      6.7K views
    • ladyboy teen shower with her daddy then eat her ass and suck her
      24:48
      ladyboy teen shower with her daddy then eat her ass and suck her
      HeShexxx
      2.3M 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
    • Transformation from a normal guy into a horny made-up sissy sex whore that can be used hard and dirty for hours.
      14:31
      Transformation from a normal guy into a horny made-up sissy sex whore that can be used hard and dirty for hours.
      Denise Humain
      53.5K views
    • Relevant Short videos

      Whiteboi sissy - Horny4evr compilation
      Whiteboi sissy - Horny4evr compilation
      Horny4evr
      6.1K views
      Sissy CD ass
      Sissy CD ass
      RosySissyTrav
      2.3K views
      Femboy with thick thighs fucks himself in the ass with a dildo
      Femboy with thick thighs fucks himself in the ass with a dildo
      Lirisen
      1.7K views
      Wait, Natasha, I Have an Order.
      Wait, Natasha, I Have an Order.
      violet_bisex
      600 views
      Sissy Kanisa's Fitting Room: Change Clothes to Go to Pe Class
      Sissy Kanisa's Fitting Room: Change Clothes to Go to Pe Class
      SissyKanisa
      833 views
      Take off Your Panties and Take Them All in Your Mouth.
      Take off Your Panties and Take Them All in Your Mouth.
      violet_bisex
      478 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
    • I finally let my stepsis fuck my trans pussy
      05:30
      I finally let my stepsis fuck my trans pussy
      CutePinkUnicorn
      618.8K 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
    • Turned into a good girl and used for his pleasure
      08:12
      Turned into a good girl and used for his pleasure
      Pure Ts
      135.2K views
    • Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      02:40
      Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      Spandexlover89
      1K views
    • Sissy Femboy Fucked From Behind
      05:20
      Sissy Femboy Fucked From Behind
      2.7M views
    • Sissy girl walking in the street in high heels
      01:14
      Sissy girl walking in the street in high heels
      Letany Ponny
      64.9K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      115.6K views
    • Fat Boy turning him into a sexy girl
      07:22
      Fat Boy turning him into a sexy girl
      Inflatable Misstress Diana Samantha Raimond
      6.5K views
    • Crossdress Trans Sissy Sloppy BlowJob JOI
      10:15
      Crossdress Trans Sissy Sloppy BlowJob JOI
      IskraElectrical49
      53.1K 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
      25.5K views
    • Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      01:17
      Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
      Allmylinks
      109.8K views
    • Spandexfembox - My Anal Alien Dildo in My Sissy Ass
      11:16
      Spandexfembox - My Anal Alien Dildo in My Sissy Ass
      Spandexlover89
      908 views
    • Sissy cums too early and gets punished with rough fucking
      02:35
      Sissy cums too early and gets punished with rough fucking
      2.1M 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
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      349.3K views
    • Cosplay  Horny Asuka Evangelion Vibrator Crossdresser Tgirl
      03:13
      Cosplay Horny Asuka Evangelion Vibrator Crossdresser Tgirl
      saxer123
      1.6K 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
      304.5K views
    • Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      02:40
      Spandexfemboy - Groan Anal Fuck Sissy Dildo Machine
      554 views
    • Asian shemale gets her tight ass stuffed with huge dildo in the dressing room
      22:27
      Asian shemale gets her tight ass stuffed with huge dildo in the dressing room
      Shemales Tales
      282.3K views
    • Straight boy likes to dress like a girl
      08:20
      Straight boy likes to dress like a girl
      Anaisfeet35
      7.6K views
    • Bulge Walk - Tight Leggings Tease
      08:13
      Bulge Walk - Tight Leggings Tease
      Medi Voi
      31.2K 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
    • Sissy Slut Motel
      58:39
      Sissy Slut Motel
      727K 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
    • I had a big cumshot in unkown hotel
      05:39
      I had a big cumshot in unkown hotel
      Samantha Sissy World
      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 Boy Dressing

    • Submissive Tranny Slut
    • Male to Female Transformation Fantasy
    • Sexy Petite Skinny Tiny Trans
    • Extreme Ladyboy Boots
    • Guy Gets Transformed Into Drag Queen
    • Sissyboy-5
    • Sissy-Slut-Jenny
    • Transvestite Sluts
    • Looking up Skirts
    • Your-Sissyslut
    • Sissy-Lili
    • Transgender Bareback
    • Big Black XXX
    • School Uniform
    • White-Sissy-Slave
    • Try on
    • Fucking Tomboy
    • Panty-Boyy
    • Sissy-Boys
    • Crossdresser-Beyza
    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