PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    Sissy Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Dress
    Sissy Dress Cum
    Sissy Maid Dresses
    Fully Dressed Sissy
    Sissy Dressed and Fucked
    Shemale Dresses Sissy Fuck
    Cuckold Sissy Husband Dress
    Sissy Boys Dress Girls
    Sissy Crossdresser Transparent Dress
    Sissy Dress up JOI
    Sissy in Pretty Dresses
    Sissy Satin Swing Dress
    Wife Makes Dress Like Sissy
    Shemale Dresses Sissy to Fuck
    Sissy Maid Dress for Mistress
    Sissy Getting Fucked Wedding Dress
    Sissy Instructions JOI Dress up
    Cross Dresses or Anal Sissy
    Sissy Faggot Playing Dress up
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Teen tranny in green latex dress strips and jerks off by the
      06:38
      Teen tranny in green latex dress strips and jerks off by the
      TS Latex
      27.2K views
    • Paula Peril Captured and Hogtied
      06:46
      Paula Peril Captured and Hogtied
      Oolasbf
      22.1K views
    • Sexy Maid Dress and Satin Panties, Sissy Clity Cum End
      07:06
      Sexy Maid Dress and Satin Panties, Sissy Clity Cum End
      Nylonpty
      32.2K views
    • Sexy chika bimbo walking around in sexy dress
      05:17
      Sexy chika bimbo walking around in sexy dress
      Letany Ponny
      178.9K views
    • Shemale and her sex buddy are fucking and sucking with their clothes on
      05:17
      Shemale and her sex buddy are fucking and sucking with their clothes on
      ShemaleTSTiara
      31.8K views
    • Trying on a new outfit
      05:39
      Trying on a new outfit
      Olivia-H
      2.8K views
    • Playing in my lovely blue dress and lingerie - Part 2
      05:25
      Playing in my lovely blue dress and lingerie - Part 2
      Rachel_biTV_uk
      30.8K views
    • Sissykanisa Mix and Match: Beige Stocking X Blue Satin Panties X Blue Satin Dress
      07:54
      Sissykanisa Mix and Match: Beige Stocking X Blue Satin Panties X Blue Satin Dress
      FapHouse
      21.4K views
    • SPH! Tranny Dom humiliates small dick loser! Stop & Go wanking while sniffing shoes!
      01:16
      SPH! Tranny Dom humiliates small dick loser! Stop & Go wanking while sniffing shoes!
      TV_Helena
      23K views
    • Sissy Bride Riding Her Doll
      18:07
      Sissy Bride Riding Her Doll
      Sissy Candy
      6.6K views
    • Cute Blonde Teen in Dress Fucked Anal
      06:12
      Cute Blonde Teen in Dress Fucked Anal
      Fembaby
      17.7K views
    • Fuck a TS shemale wearing full tight clothing in the hotel
      05:48
      Fuck a TS shemale wearing full tight clothing in the hotel
      tsts9
      22.1K views
    • Julian069 silver partydress 75
      04:02
      Julian069 silver partydress 75
      Julian069
      19.7K views
    • Masturbate in a sexy black outfit
      07:28
      Masturbate in a sexy black outfit
      WanidaCrossdresser
      4.8K views
    • Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails
      07:52
      Sissy Dressed up as a Mistress to Get a Sissy of Her Own but Fails
      FapHouse
      18.8K views
    • Little Blonde Sissy in Black Skirt and Stockings
      03:12
      Little Blonde Sissy in Black Skirt and Stockings
      SissyfrenchDoll
      5.3K views
    • Teasing you in my black satin dress, full make up, pearls, opera leather gloves, stockings, suspenders, pearls, chastity, blonde
      01:08
      Teasing you in my black satin dress, full make up, pearls, opera leather gloves, stockings, suspenders, pearls, chastity, blonde
      JessicaXD
      2K views
    • Learning How to Dress to Attract Men
      04:04
      Learning How to Dress to Attract Men
      Nancy Rose
      34K views
    • White Slut Sissy
      03:06
      White Slut Sissy
      SissyfrenchDoll
      3.9K views
    • Sissy Maid in Bondage Sucking and Fucking Her Dildo
      08:22
      Sissy Maid in Bondage Sucking and Fucking Her Dildo
      Sissy Candy
      2.7K views
    • Sissy Presenting New Dress and Small Walk Around Outdoor
      06:06
      Sissy Presenting New Dress and Small Walk Around Outdoor
      SissyDaniella
      2.1K views
    • Sexy Crossdresser kellycd2022 in pink outfit and heels
      18:18
      Sexy Crossdresser kellycd2022 in pink outfit and heels
      Kellycd2022
      7.6K views
    • Tied up and left in the mud! Wet and messy tranny girl pees in her pants!
      01:11
      Tied up and left in the mud! Wet and messy tranny girl pees in her pants!
      Allmylinks
      2.3K views
    • Playing with myself while enjoying a cigarette
      05:09
      Playing with myself while enjoying a cigarette
      Denise_smokeslut
      13.2K views
    • Naughty slut in tight dress and black pantyhose plays public with remote dildo and orgasms with anal and cum after coming back
      11:29
      Naughty slut in tight dress and black pantyhose plays public with remote dildo and orgasms with anal and cum after coming back
      Harinni
      5.6K views
    • Kellystar518 in NO ASS - NO KEY!
      11:36
      Kellystar518 in NO ASS - NO KEY!
      Kellystar518
      21.2K views
    • Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      08:12
      Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      1.8K views
    • Sexy crossdresser kellycd2022 in white dress and sexy see thru bra and panties holiday video
      19:29
      Sexy crossdresser kellycd2022 in white dress and sexy see thru bra and panties holiday video
      Kellycd2022
      6.7K views
    • Sexy submissive girl in sexy dress
      06:37
      Sexy submissive girl in sexy dress
      Letany Ponny
      61.6K views
    • Suck mommies gorgeous clitty - good boy!
      05:40
      Suck mommies gorgeous clitty - good boy!
      Cindy Belfast
      16.8K views
    • Do Whatever the Viewer Wants with a Transparent Chinese Dress...
      11:12
      Do Whatever the Viewer Wants with a Transparent Chinese Dress...
      KANAe
      16K views
    • Sexy Crossdresser kellycd2022 in gold shiny animal print dress and pantyhose heels
      19:37
      Sexy Crossdresser kellycd2022 in gold shiny animal print dress and pantyhose heels
      Kellycd2022
      6.3K views
    • Sexy Crossdresser kellycd2022 in shiny gold dress enjoying an afternoon drive
      45:52
      Sexy Crossdresser kellycd2022 in shiny gold dress enjoying an afternoon drive
      Kellycd2022
      24.5K views
    • Cum with me! Dirtytalk and POV
      03:39
      Cum with me! Dirtytalk and POV
      Sissy Slut Chantal Sweet
      48.8K views
    • Kelly goes for a walk downtown in a tight slutty dress
      05:51
      Kelly goes for a walk downtown in a tight slutty dress
      Kelly Pink
      10K views
    • Sissy attempting to get off in her pink diaper with a wand
      02:44
      Sissy attempting to get off in her pink diaper with a wand
      SissyFoxPrincess
      26.5K views
    • Sissy waking outside in sexy black dress and high heels
      05:01
      Sissy waking outside in sexy black dress and high heels
      Letany Ponny
      150.9K views
    • Crossdresser waiting for bus in short dress at night
      03:57
      Crossdresser waiting for bus in short dress at night
      Niya_cd
      169.9K views
    • Office Wear Masturbation
      12:46
      Office Wear Masturbation
      Sissy Paige
      25K views
    • Spandexfemboy - Psychodelic Sissy Anal Fuck
      16:26
      Spandexfemboy - Psychodelic Sissy Anal Fuck
      3K views
    • Tgirl in Sexy outfit takes off chastity cage, jerks off and finish with a Self Facial
      07:21
      Tgirl in Sexy outfit takes off chastity cage, jerks off and finish with a Self Facial
      Mariana Taylor
      15.3K views
    • Hot trans CD in tight gray dress teasing huge cock
      06:41
      Hot trans CD in tight gray dress teasing huge cock
      CuteCynthia
      10.5K views
    • Sissy Whiteboi dress Girly, and show off!
      09:39
      Sissy Whiteboi dress Girly, and show off!
      Sissy Cindy Slut
      1.3K views
    • its inevitable, once you dress up like a girl
      05:22
      its inevitable, once you dress up like a girl
      91.1K views
    • Masturbation in pantyhose and leather dress (two perspectives)
      06:48
      Masturbation in pantyhose and leather dress (two perspectives)
      Nylonizer
      20.9K views
    • Princess Bunnie: White Satin Dress Masturbation
      09:34
      Princess Bunnie: White Satin Dress Masturbation
      Princess Bunnie
      4.4K views
    • Sybl, my first tease in a dress
      02:55
      Sybl, my first tease in a dress
      Queen Sibel
      41.7K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 6
    4. 7
    5. 8
    6. 9
    7. 10
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Sissy Dressing

    • Free Use
    • Sharing Hotel Room
    • Crossdresserkitty
    • Transvestite Striptease
    • Sloppy Seconds
    • Unexpected Creampie
    • Crazy Trannys
    • See Through Lingerie
    • Slave-Of-Mistress
    • Trapped
    • Private Society
    • Mistress Catriona Dark
    • Hooker Fucks Guy
    • Older Tgirls
    • Hot 40 Plus
    • Skinny but Plenty
    • Dominant Transsexuals
    • Gender Bender
    • Chastity Bottom
    • Fuck Me Fuck Me Fuck Me
    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