PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    BLUE MONDAY SALE 💛🎉 Brighten the year’s saddest day
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Bareback
    • Creampie
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy Dressing Up
    Best Videos
    By clicking the content you will also see an ad. AD
    Sissy dressing up slowly in pastel-colored bedroom
    07:52
    Sissy dressing up slowly in pastel-colored bedroom
    Crossdresserkitty
    1.1K views
    Boss fucks the ass of delicious trans secretary
    07:40
    Boss fucks the ass of delicious trans secretary
    Marine Laveau
    198.3K 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
    Cross Dressing Student and Tutor Playing with Each Other
    08:12
    Cross Dressing Student and Tutor Playing with Each Other
    Crossdressing Amateurs
    302.8K views
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    03:09
    A dress, heels and a chastity cage. Trying a huge dildo and cumming in my tights!
    Starlightfemboy
    437K views
    Green Satin Dress, Tits, no bra and cum
    12:37
    Green Satin Dress, Tits, no bra and cum
    Sarahsatinslut
    26.3K views
    My stepdad fucks my ass while I'm home alone
    07:29
    My stepdad fucks my ass while I'm home alone
    Marine Laveau
    59.1K views
    Fabulous in Green: Three Wigs, One Dress, and Smooth Girly Legs!
    09:09
    Fabulous in Green: Three Wigs, One Dress, and Smooth Girly Legs!
    Crossdresserkitty
    605.6K views
    Black Lingerie Crossdresser Fucks Black Dress Petite Trans Woman
    06:05
    Black Lingerie Crossdresser Fucks Black Dress Petite Trans Woman
    Bailey Wilde
    223.4K views
    Sexy legs with silver dress and heels
    08:10
    Sexy legs with silver dress and heels
    Queen Sibel
    195.6K views
    Mature Cross Dressing Duo Blow and Jerk Each Other off Until Completition
    08:01
    Mature Cross Dressing Duo Blow and Jerk Each Other off Until Completition
    Crossdressing Amateurs
    180.2K views
    Would you like to feel my bulge in my dress
    05:15
    Would you like to feel my bulge in my dress
    Hollycd1
    16.1K views
    Trans Stepmother Discovers Your Secret Sissy Closet
    07:15
    Trans Stepmother Discovers Your Secret Sissy Closet
    Natalie Napoli
    14.2K views
    No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
    04:44
    No Escaping Bondage - Sissy Maid Punishment - Steel Rigid Ankle-Wrist Spreader
    Derek6699
    268.7K views
    Sexy TS Lucia Maya in pink dress & heels FUCKS HER ASS & CUMS!
    24:21
    Sexy TS Lucia Maya in pink dress & heels FUCKS HER ASS & CUMS!
    Lucia Maya
    222.2K views
    no hands cumming
    17:59
    no hands cumming
    rieli
    378K views
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    23:36
    Sissy Maid Gets Locked in Bondage and Chastity to Be Fucked by Her Sex Doll
    Sissy Candy
    30.9K views
    Amazing facial cumshot on my slut of a boyfriend after an epic mutual ass-licking
    06:55
    Amazing facial cumshot on my slut of a boyfriend after an epic mutual ass-licking
    DotadaSP
    734.6K views
    Now Her Life Has Purpose
    08:12
    Now Her Life Has Purpose
    Pure Ts
    33.1K views
    Princess Bunnie: Pin-up Masturbation and Cumshot
    02:09
    Princess Bunnie: Pin-up Masturbation and Cumshot
    Princess Bunnie
    17.4K views
    Dressed in White and Ready to Submit
    08:12
    Dressed in White and Ready to Submit
    Pure Ts
    22.1K views
    Under My Skirt: Best Stocking & POV Compilation
    05:28
    Under My Skirt: Best Stocking & POV Compilation
    Medi Voi
    8.6K views
    Delicious trans sucks his cock until all the milk comes out in a jacuzzi
    07:30
    Delicious trans sucks his cock until all the milk comes out in a jacuzzi
    Marine Laveau
    28.3K views
    Young sissy sucking and getting fucked by Daddys BBC in pink mesh dress
    03:47
    Young sissy sucking and getting fucked by Daddys BBC in pink mesh dress
    Ericka Sprinkle
    161.9K views
    Pretty trans caresses herself and cums
    08:42
    Pretty trans caresses herself and cums
    Sabrina Iu
    23K views
    I'm in public but I forgot to wear panties
    05:09
    I'm in public but I forgot to wear panties
    cd_aysemmm
    159.4K views
    Princess Bunnie: Crossdresser MILF masturbating
    07:01
    Princess Bunnie: Crossdresser MILF masturbating
    Princess Bunnie
    43.4K views
    Dress Up Sissy Costume Tasks
    10:49
    Dress Up Sissy Costume Tasks
    Natalie Napoli
    23.5K views
    elegant skinny mistress with blue dress and lipstick huge cock cumshot
    02:49
    elegant skinny mistress with blue dress and lipstick huge cock cumshot
    Nadja Cox
    159.4K views
    Josie Blade all the good stuff
    31:14
    Josie Blade all the good stuff
    Josie Blade
    390.5K views
    Fucked Against the Wall in My Casual Dress
    08:12
    Fucked Against the Wall in My Casual Dress
    Josie Blade
    352.2K views
    The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
    10:53
    The Sissy Pain Whore was ass fucked head down in a toilet. Alina The Whore got sissygasm and both her greedy holes got feeded
    alinanightsky
    274.9K views
    Cumming in my Sparkly Blue Leotard Dress
    03:26
    Cumming in my Sparkly Blue Leotard Dress
    KelseyCobalt
    195.8K views
    Amazing cum shot featuring Alexandra Braces in a red dress, pantyhose and Converse
    03:24
    Amazing cum shot featuring Alexandra Braces in a red dress, pantyhose and Converse
    Alexandra Braces
    48.3K views
    Red dress
    15:14
    Red dress
    Roni Swallows
    23.9K views
    Huge as Sissy shakes ass in Pink Dress
    04:37
    Huge as Sissy shakes ass in Pink Dress
    Ruby Robby
    86.4K views
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    11:21
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    Sissy Candy
    51.8K views
    Sissy slut shoots cum into her own mouth
    10:34
    Sissy slut shoots cum into her own mouth
    Natasha Sparklez
    75.9K views
    Crossdresser riding dildo with black dress and heels
    07:34
    Crossdresser riding dildo with black dress and heels
    Queen Sibel
    48.6K views
    Very hot policeman fucks trans girl until she destroys her ass
    07:32
    Very hot policeman fucks trans girl until she destroys her ass
    Marine Laveau
    37.8K views
    Rough Sex with cute Tranny Girl! Clothes Ripping! CBT! Moutfuck! Facials!
    01:18
    Rough Sex with cute Tranny Girl! Clothes Ripping! CBT! Moutfuck! Facials!
    TV_Helena
    32.3K views
    Sissy Dressed Up And Playing With My Cock
    23:43
    Sissy Dressed Up And Playing With My Cock
    Sissy Paige
    35K views
    Guy brutally fucks tranny in the mouth and cums in her face!
    01:11
    Guy brutally fucks tranny in the mouth and cums in her face!
    Allmylinks
    102.1K views
    Sexy Thick sissy in fishnets at work
    05:29
    Sexy Thick sissy in fishnets at work
    Ruby Robby
    48.5K views
    An afternoon in the park with Janice Renee
    02:29
    An afternoon in the park with Janice Renee
    Janice Renee
    234.2K views
    Used and humiliated! Tranny has to piss in, two guys cum and piss on her!
    01:17
    Used and humiliated! Tranny has to piss in, two guys cum and piss on her!
    TV_Helena
    139.1K views
    CD emo outdoor walking at railway station. slut outfit
    30:07
    CD emo outdoor walking at railway station. slut outfit
    emy4all
    158.9K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Dressing

    • Sissy Boys Dress Girls
    • Crossdresser First Time With a Man
    • Boy Dressed as Girl
    • Mature Crossdressers and Sissys
    • Crossdressing Bridal Lingerie
    • Femboy in Skirt
    • Transvestite Dressing up
    • Crossdress Fucked
    • Caught Wearing Sisters Clothes
    • Secret Sissyboy
    • Transvestites Sissies
    • Sissy-Virgin
    • Sissification Process
    • Cross Dressers
    • Your-Sissyslut
    • Male to Female Transformation
    • Sissy-Slut-Jenny
    • Trans High Heels XXX
    • The Sissy's Future
    • Transformed Into Slut
    xHamster
    • Press
    • 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
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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