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

    Dressing Sissy 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
    • Holly's got a bulge in her skirt at the cruising area
      09:11
      Holly's got a bulge in her skirt at the cruising area
      Hollycd1
      19.1K views
    • Carina undresses
      03:17
      Carina undresses
      CarinaDavid
      6.8K views
    • Short Satin Dress with Tights
      03:28
      Short Satin Dress with Tights
      Sarahsatinslut
      3.5K views
    • Hola a qui yo Francis un nuevo video para ustedes
      05:16
      Hola a qui yo Francis un nuevo video para ustedes
      Francispads
      32.3K views
    • MelindaJamesCD Presenting her Ass and Cock in Sexy Outfit
      06:34
      MelindaJamesCD Presenting her Ass and Cock in Sexy Outfit
      Melinda James
      26.6K views
    • Fucked barebacked in my new sexy dress
      02:28
      Fucked barebacked in my new sexy dress
      81.1K views
    • emo cd outdoor walking at railway station. dressed like a slut
      34:16
      emo cd outdoor walking at railway station. dressed like a slut
      emy4all
      43.5K views
    • Red dress and stockings
      05:06
      Red dress and stockings
      Georgia cross
      21.5K views
    • Anal Stretching and Gape with a Dilator - Extreme Anal Insertions
      03:55
      Anal Stretching and Gape with a Dilator - Extreme Anal Insertions
      Jasmine_dlight
      45.1K views
    • mistress in black leather dress with big cock makes you horny and cum big cumshot
      03:16
      mistress in black leather dress with big cock makes you horny and cum big cumshot
      Nadja Cox
      22.1K views
    • Young transgender woman in Japan dressing up as a woman doing something good with anal
      12:25
      Young transgender woman in Japan dressing up as a woman doing something good with anal
      harucoco
      2.7K views
    • Crossdresser locked out of hotel room in sissy dress
      06:27
      Crossdresser locked out of hotel room in sissy dress
      43K views
    • Crossdresser in Vinyl Dresses, Stockings and Mules Caresses Herself.
      03:52
      Crossdresser in Vinyl Dresses, Stockings and Mules Caresses Herself.
      Faustine crossdresser
      1.9K views
    • Thick monster cock fucks me hard in my bikini trans-girl outfit - prettyboi2000x
      15:12
      Thick monster cock fucks me hard in my bikini trans-girl outfit - prettyboi2000x
      Prettyboi2000x
      2.3K views
    • "Come closer: feel the heat of this moment and let yourself be carried away by the passion"
      05:39
      "Come closer: feel the heat of this moment and let yourself be carried away by the passion"
      Melinda James
      49.6K views
    • Cock whore face writing - public toilet and night walk
      24:26
      Cock whore face writing - public toilet and night walk
      AngelSissyWhore
      2.1K 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
    • Erika Oak Shows Off Her Muscular Veiny Girlcock
      03:20
      Erika Oak Shows Off Her Muscular Veiny Girlcock
      Erika Oak
      51.4K views
    • Dressed in Drag and Fucked after Girls Night Out
      12:20
      Dressed in Drag and Fucked after Girls Night Out
      Bailey Wilde
      54.7K views
    • What the FUCK is this? sissy rich boy cross-dress
      11:59
      What the FUCK is this? sissy rich boy cross-dress
      Latina Tranny
      170K views
    • She lets me choose my cute little outfit
      07:50
      She lets me choose my cute little outfit
      Emptyhead
      34.8K views
    • Bubble Butt Fishnets Femboy Faggot Inflatable Knotted Dildo Part II
      02:36
      Bubble Butt Fishnets Femboy Faggot Inflatable Knotted Dildo Part II
      l lbyttslutzora
      12.1K views
    • Crossdresser Danni really missed you all. Nylon, tight dress, high heels and a hard cock i couldnt help but show off and cum.
      10:35
      Crossdresser Danni really missed you all. Nylon, tight dress, high heels and a hard cock i couldnt help but show off and cum.
      Danni Loves
      22.3K views
    • Cum in mouth and all over Alexandra's metal braces
      02:09
      Cum in mouth and all over Alexandra's metal braces
      Alexandra Braces
      62.6K views
    • I take off my dress and walk around naked
      08:47
      I take off my dress and walk around naked
      slurpium
      5.7K views
    • Sissy in Pink
      10:21
      Sissy in Pink
      Emptyhead
      38K views
    • Elisya Amateur In Niqab Clothes Hijab Masturbates To Squirting Orgasm Hard
      05:36
      Elisya Amateur In Niqab Clothes Hijab Masturbates To Squirting Orgasm Hard
      HijabRubberSexDoll
      224.3K views
    • Dominatrix Dresses Up Sissy in Dress
      02:14
      Dominatrix Dresses Up Sissy in Dress
      Bailey Wilde
      50.2K views
    • Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand
      09:21
      Sissy Maid in Hot Pink Dress and Chastity Is Locked to Her Dildo Stand
      Sissy Candy
      17.5K views
    • Hentai Cosplay Dick and chest massage from behind, My Dress-Up Darling Rizu-kyun anime cosplay part.11
      05:24
      Hentai Cosplay Dick and chest massage from behind, My Dress-Up Darling Rizu-kyun anime cosplay part.11
      Haru
      71.1K views
    • Sissy Maid Dildo Stand Bondage and Cum Dump
      16:01
      Sissy Maid Dildo Stand Bondage and Cum Dump
      Sissy Candy
      3.7K views
    • Flower bloom on my dick! (SisK lingerie collection EP3)
      09:54
      Flower bloom on my dick! (SisK lingerie collection EP3)
      SissyKanisa
      54.4K views
    • Dildo in My Ass, Lingerie and Heels on Me
      05:10
      Dildo in My Ass, Lingerie and Heels on Me
      MicziCD
      30.8K views
    • Public Crossdressing... Sissy in very short dresses outside
      05:07
      Public Crossdressing... Sissy in very short dresses outside
      19.4K views
    • A new Messi task; dirty dress and stockings in piss and cum 2
      09:06
      A new Messi task; dirty dress and stockings in piss and cum 2
      Loreleyadd
      2.9K views
    • Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm
      13:05
      Sissy Candy's Gets Used by Her Fucking Machine and Has Her Very First Sissygasm
      Sissy Candy
      53.3K views
    • Crossdresser is shopping for clothes, live in the dressing room
      05:20
      Crossdresser is shopping for clothes, live in the dressing room
      Loreleyadd
      21.3K views
    • Dominatrix Dresses Up and Fucks Sissy
      08:22
      Dominatrix Dresses Up and Fucks Sissy
      Bailey Wilde
      32.9K views
    • Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
      04:41
      Deep throat training in a tight black satin dress, stockings, satin opera gloves, blonde, lipstick, glasses, frustrated in chast
      JessicaXD
      986 views
    • Lot requested outfit and toy - Going deep in to anal
      09:42
      Lot requested outfit and toy - Going deep in to anal
      Ylvis88
      105.2K 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
    • 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
    • FGO Chinese dress Cosplayer, she fucked by sex friend, Tamamo vitch koyanskaya Part.6
      05:14
      FGO Chinese dress Cosplayer, she fucked by sex friend, Tamamo vitch koyanskaya Part.6
      Haru
      149.3K 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
    • Beautiful girl likes this dress
      05:45
      Beautiful girl likes this dress
      JessicaXD
      969 views
    • Julian069 silver partydress 75
      04:02
      Julian069 silver partydress 75
      Julian069
      19.7K views
    Previous page
    Next page
    1
    1. 1
    2. ...
    3. 5
    4. 6
    5. 7
    6. 8
    7. 9
    8. ...
    9. 44
    10. ...
    11. 80
    80

    Searches Related to Dressing Sissy

    • Nice Transvestite Suck
    • Crissy B Cumming
    • Ripping Clothes off
    • Stripping Homemade
    • Leotard
    • Pussy Stick
    • Tranny Surprises Guy
    • Jizz Taylor
    • Surprise Have Dick
    • Envy Darling
    • White-sissy-slave Leaked
    • Sexy Shemales Suspenders Garter Belt
    • Cock Teasing
    • Femboys in Leggings
    • Bridesmaid
    • Lollipop Ginger Nude
    • Gorgeous Transsexual
    • Ladyboy Barbie
    • Tights
    • Jean Shorts
    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