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

    Sissy Dressed Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Crossdresser Dress and Girdle
    Cross Dressing Sissy Loses His Virginity
    Sissy Cross Dressing Husband Loves BBC
    Sissy Maid Dress up for Mistress
    Dominatrix Dresses up Sissy in Dress
    Sissy Secretary Getting Dressed for Work
    Dress Like Sissy and Suck Cock for
    Guys Dress Their Sissy Friend and Fuck
    Dress Like Sissy and Suck This Dick
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Turned into a good girl and used for his pleasure
      08:12
      Turned into a good girl and used for his pleasure
      Pure Ts
      133.9K views
    • Man Dressed as Woman and Fucked by Dominatrix
      06:11
      Man Dressed as Woman and Fucked by Dominatrix
      Bailey Wilde
      212.2K 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
    • Femboy cums in glitter dress
      10:35
      Femboy cums in glitter dress
      Emptyhead
      55.9K views
    • SISSY TRANSFORMATION
      11:07
      SISSY TRANSFORMATION
      652.1K views
    • Nicely Dressed but I Want You Inside Me
      08:12
      Nicely Dressed but I Want You Inside Me
      Ficd
      34.4K views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.5M views
    • Sissy Maid Gets Dressed, Cuffed and Locked and Rides Her Doll
      18:35
      Sissy Maid Gets Dressed, Cuffed and Locked and Rides Her Doll
      Sissy Candy
      45.4K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      240.3K views
    • Red Dress Crossdresser Fucks Red Lingerie Petite Trans Woman
      06:03
      Red Dress Crossdresser Fucks Red Lingerie Petite Trans Woman
      Bailey Wilde
      28.2K views
    • Crossdress Trans Sissy Sloppy BlowJob JOI
      10:15
      Crossdress Trans Sissy Sloppy BlowJob JOI
      IskraElectrical49
      53.1K views
    • Man Transformed into Woman and Fucked Dressed as Maid
      10:34
      Man Transformed into Woman and Fucked Dressed as Maid
      Bailey Wilde
      294.8K 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
    • Man Put in Chastity and Dressed as Maid for Job
      05:17
      Man Put in Chastity and Dressed as Maid for Job
      Bailey Wilde
      31.6K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M views
    • Cute tranny walking public with butt plug! Hard cock stroked til cumshot!
      01:17
      Cute tranny walking public with butt plug! Hard cock stroked til cumshot!
      TV_Helena
      10.6K views
    • Bulge Walk - Tight Leggings Tease
      08:13
      Bulge Walk - Tight Leggings Tease
      Medi Voi
      31.2K views
    • Sissy Sophie trains her hole against the wall
      07:11
      Sissy Sophie trains her hole against the wall
      Sophie Valentine
      71.4K views
    • Tv is for Sissies (Full Video)
      56:35
      Tv is for Sissies (Full Video)
      622.2K views
    • I dressed as a woman and masturbated in my panties
      13:01
      I dressed as a woman and masturbated in my panties
      harucoco
      4K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.4M 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
    • I finally let my stepsis fuck my trans pussy
      05:30
      I finally let my stepsis fuck my trans pussy
      CutePinkUnicorn
      616.5K views
    • Guy First Time Dressed as Woman and Strapon Fuck
      04:51
      Guy First Time Dressed as Woman and Strapon Fuck
      Bailey Wilde
      70.2K 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
    • 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
    • Teen Sissy Already Knows Her Place
      08:12
      Teen Sissy Already Knows Her Place
      Pure Ts
      73.1K views
    • Cum without stroking, Clothed Rubbing JOI
      18:58
      Cum without stroking, Clothed Rubbing JOI
      April Bee
      68.5K views
    • Completely Submitted and Feminized
      08:12
      Completely Submitted and Feminized
      Pure Ts
      49.6K views
    • I Tear off Her Sticky to Better Play with Her
      01:18
      I Tear off Her Sticky to Better Play with Her
      Nady-So
      2.2K views
    • I had a big cumshot in unkown hotel
      05:39
      I had a big cumshot in unkown hotel
      Samantha Sissy World
      1.6M 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
    • Sissy Femboy Fucked From Behind
      05:20
      Sissy Femboy Fucked From Behind
      2.7M views
    • Dominatrix Dresses Up and Fucks Sissy
      08:22
      Dominatrix Dresses Up and Fucks Sissy
      Bailey Wilde
      32.9K views
    • Girl forgot to tell her Tinder date that she’s Trans
      07:22
      Girl forgot to tell her Tinder date that she’s Trans
      JsseMontz
      638.7K views
    • Nady Climbs on My Strap-on Dildo and Fucks Her Anal Pussy
      01:10
      Nady Climbs on My Strap-on Dildo and Fucks Her Anal Pussy
      Nady-So
      2.4K views
    • Trans lingerie haul - with Jennifer Lunden
      20:06
      Trans lingerie haul - with Jennifer Lunden
      Jennifer Lunden
      265K views
    • Trans with a Gorgeous Body Dressed up and Horny for Her Dildo
      07:19
      Trans with a Gorgeous Body Dressed up and Horny for Her Dildo
      Melodyfluffington
      12.9K views
    • Sexy Crossdresser in sheer lingerie gets fucked doggy style
      05:25
      Sexy Crossdresser in sheer lingerie gets fucked doggy style
      MTFXXXVIDS
      55.1K views
    • Dressed as a woman, dressed in Japanese style, and ejaculated in pink underwear
      07:16
      Dressed as a woman, dressed in Japanese style, and ejaculated in pink underwear
      harucoco
      4.3K views
    • Your Little Fag Sissy Princess
      11:31
      Your Little Fag Sissy Princess
      Natalie Napoli
      25.6K views
    • Well-dressed femboy strips naked in the kitchen, fucks her ass and squeezes milk out of her small cock
      18:36
      Well-dressed femboy strips naked in the kitchen, fucks her ass and squeezes milk out of her small cock
      femboyass469
      16K views
    • Sissy Joyce - A real life sissy slave
      01:16
      Sissy Joyce - A real life sissy slave
      Sissy Joyce
      691.4K views
    • Dressed up and Looking Gorgeous
      07:29
      Dressed up and Looking Gorgeous
      Pure Ts
      5.7K views
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      340.1K views
    • Slutty T-girl Dressed Provacatively, Blowjobs and Anal
      17:49
      Slutty T-girl Dressed Provacatively, Blowjobs and Anal
      Melodyfluffington
      46K views
    • BBC Fucks a Slutty Crossdresser Without Limits
      32:44
      BBC Fucks a Slutty Crossdresser Without Limits
      Trans and Co
      384.7K 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 Dressed

    • Femboys in Leggings
    • Transgender Skirt
    • Transvestites Sissies
    • Feminized
    • Crossdresserkitty
    • Boy Dressed as Girl
    • Sissys Get Blacked
    • Schoolgirl Uniform
    • Secret Sissyboy
    • Crossdresserlover Ladyboys
    • Trap Cosplay Porn
    • Man Transformed Into Woman
    • Heavy Makeup Tranny Whore
    • Caught Wearing Sisters Clothes
    • The Sissy's Future
    • Nylon Fetish
    • Femboy Sissy
    • Slutty Crossdresser
    • Crossdressing Homemade
    • Frilly Panties
    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