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

    Sissy Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Dress
    Sissy Dress Cum
    Sissy Cock Dress
    Sissy Dressed and Fucked
    Shemale Dresses Sissy Fuck
    Cuckold Sissy Husband Dress
    Sissy Boys Dress Girls
    Sissy Crossdresser Transparent Dress
    Sissy Satin Swing Dress
    Mature Sissy Party Dress
    Wife Makes Dress Like Sissy
    Shemale Dresses Sissy to Fuck
    Sissy Crossdresser Christmas Party Dress
    Sissy Maid Dress for Mistress
    Sissy Instructions JOI Dress up
    Sissy Getting Fucked Wedding Dress
    Sissy 1950 039 Prom Dress
    Sissy Faggot Playing Dress up
    Cross Dresses or Anal Sissy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Julian069 silver partydress 75
      04:02
      Julian069 silver partydress 75
      Julian069
      19.7K views
    • Little Blonde Sissy in Black Skirt and Stockings
      03:12
      Little Blonde Sissy in Black Skirt and Stockings
      SissyfrenchDoll
      4.9K views
    • Sexy Maid Dress and Satin Panties, Sissy Clity Cum End
      07:06
      Sexy Maid Dress and Satin Panties, Sissy Clity Cum End
      Nylonpty
      31.8K 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
    • 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
    • Masturbate in a sexy black outfit
      07:28
      Masturbate in a sexy black outfit
      WanidaCrossdresser
      4.4K views
    • Beautiful girl likes this dress
      05:45
      Beautiful girl likes this dress
      JessicaXD
      969 views
    • Sexy chika bimbo walking around in sexy dress
      05:17
      Sexy chika bimbo walking around in sexy dress
      Letany Ponny
      178.3K 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
      Sissy Candy
      18.8K 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
      SissyKanisa
      20.9K views
    • Trying on a new outfit
      05:39
      Trying on a new outfit
      Olivia-H
      2.8K views
    • Paula Peril Captured and Hogtied
      06:46
      Paula Peril Captured and Hogtied
      Oolasbf
      22.1K 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
    • White Slut Sissy
      03:06
      White Slut Sissy
      SissyfrenchDoll
      3.7K views
    • Sissy Bride Riding Her Doll
      18:07
      Sissy Bride Riding Her Doll
      Sissy Candy
      6K views
    • Playing with myself while enjoying a cigarette
      05:09
      Playing with myself while enjoying a cigarette
      Denise_smokeslut
      12.8K views
    • Suck mommies gorgeous clitty - good boy!
      05:40
      Suck mommies gorgeous clitty - good boy!
      Cindy Belfast
      16.6K 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
      22.4K 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
      5.2K views
    • Learning How to Dress to Attract Men
      04:04
      Learning How to Dress to Attract Men
      Nancy Rose
      33.8K 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
      21.4K views
    • Relevant Short videos

      Please suck my little trans dick🥺
      Please suck my little trans dick🥺
      SissyGurl_Autumn
      20.2K views
      Lovely blue pleated dress
      Lovely blue pleated dress
      Rachel_biTV_uk
      28.2K views
      Faggot femboy in hottest outfit warming her holes ready for daddy to come fuck her
      Faggot femboy in hottest outfit warming her holes ready for daddy to come fuck her
      Vyktorya Kaner
      10.1K views
      Crossdresser Kellycd2022 sexy milf cumshot moment in black pvc dress and seamless pantyhose
      Crossdresser Kellycd2022 sexy milf cumshot moment in black pvc dress and seamless pantyhose
      Kellycd2022
      12.9K views
      Outdoor exhibition in the forest with schoolgirl outfit
      Outdoor exhibition in the forest with schoolgirl outfit
      Justine Love
      15.9K views
      Shiny transvestite hip thrust in tight nylon dress
      Shiny transvestite hip thrust in tight nylon dress
      Kara Fetishdol
      6.8K views
    • Sexy Crossdresser kellycd2022 in pink outfit and heels
      18:18
      Sexy Crossdresser kellycd2022 in pink outfit and heels
      Kellycd2022
      7K views
    • Cute Blonde Teen in Dress Fucked Anal
      06:12
      Cute Blonde Teen in Dress Fucked Anal
      Fembaby
      17.7K 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
      1.4K views
    • Kellystar518 in NO ASS - NO KEY!
      11:36
      Kellystar518 in NO ASS - NO KEY!
      Kellystar518
      20.9K 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
    • 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
    • Office Wear Masturbation
      12:46
      Office Wear Masturbation
      Sissy Paige
      24.8K views
    • Cum with me! Dirtytalk and POV
      03:39
      Cum with me! Dirtytalk and POV
      Sissy Slut Chantal Sweet
      48.4K 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
    • 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
    • Do Whatever the Viewer Wants with a Transparent Chinese Dress...
      11:12
      Do Whatever the Viewer Wants with a Transparent Chinese Dress...
      KANAe
      15.6K views
    • Sexy submissive girl in sexy dress
      06:37
      Sexy submissive girl in sexy dress
      Letany Ponny
      61.2K 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
      26.1K views
    • Hot trans CD in tight gray dress teasing huge cock
      06:41
      Hot trans CD in tight gray dress teasing huge cock
      CuteCynthia
      9.9K views
    • Spandexfemboy - Psychodelic Sissy Anal Fuck
      16:26
      Spandexfemboy - Psychodelic Sissy Anal Fuck
      Spandexlover89
      2.7K views
    • Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      08:12
      Spandexfemboy - Huge BBC Anal Sissy Fuck Music and Groan
      Spandexlover89
      1.5K views
    • Blonde shemale in red latex dress teases with her cock out
      08:57
      Blonde shemale in red latex dress teases with her cock out
      TS Latex
      19.3K 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
    • Trans girl in a very short dress rubs his big cock to squeeze out all his cum
      15:11
      Trans girl in a very short dress rubs his big cock to squeeze out all his cum
      Kayndrift 0wtis
      just added
    • Princess Bunnie: White Satin Dress Masturbation
      09:34
      Princess Bunnie: White Satin Dress Masturbation
      Princess Bunnie
      4.4K views
    • Kitsy gets hand spanked OTK.
      11:43
      Kitsy gets hand spanked OTK.
      Kitsy Meow
      17.5K views
    • its inevitable, once you dress up like a girl
      05:22
      its inevitable, once you dress up like a girl
      90.7K views
    • misr4 - Burgundy lingerie
      06:38
      misr4 - Burgundy lingerie
      misr4
      8.3K views
    • Sissy Maid Gets Her Collar Locked to Her Doll's Cock!
      19:22
      Sissy Maid Gets Her Collar Locked to Her Doll's Cock!
      Sissy Candy
      3.1K views
    • Sissy Whiteboi dress Girly, and show off!
      09:39
      Sissy Whiteboi dress Girly, and show off!
      Sissy Cindy Slut
      1.1K views
    • SWEATER DRESS MESS EXTENDED CLIP
      05:43
      SWEATER DRESS MESS EXTENDED CLIP
      Syn Thetic
      16.5K 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

    • Degraded Sissies
    • Short Skirt Bend Over
    • Bulge Tights
    • Shemale Underwear
    • Mrs Samantha
    • Asian Dominatrix
    • Tranny Bikini
    • Transexual Nudes
    • Lingerie Creampie
    • Horny Femboys
    • Makeover
    • German Crossdresser01
    • Ladyboy Leather
    • Homemade Lesbian Strapon
    • White Whore for Black Pimp
    • Cuckold Pegging
    • Chasity Cage
    • Cross Dresser
    • Lipstick Fetish
    • Transvestite Dressing
    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