PornPorn Transgender • US
    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
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!
    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
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • 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
    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
    436K views
    Green Satin Dress, Tits, no bra and cum
    12:37
    Green Satin Dress, Tits, no bra and cum
    Sarahsatinslut
    26.3K 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
    266.7K 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
    Now Her Life Has Purpose
    08:12
    Now Her Life Has Purpose
    Pure Ts
    31.8K views
    Princess Bunnie: Pin-up Masturbation and Cumshot
    02:09
    Princess Bunnie: Pin-up Masturbation and Cumshot
    Princess Bunnie
    16.3K views
    Dressed in White and Ready to Submit
    08:12
    Dressed in White and Ready to Submit
    Pure Ts
    21.1K 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
    Princess Bunnie: Crossdresser MILF masturbating
    07:01
    Princess Bunnie: Crossdresser MILF masturbating
    Princess Bunnie
    43.4K views
    Huge as Sissy shakes ass in Pink Dress
    04:37
    Huge as Sissy shakes ass in Pink Dress
    Ruby Robby
    86.4K 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
    Sexy Thick sissy in fishnets at work
    05:29
    Sexy Thick sissy in fishnets at work
    Ruby Robby
    48.5K views
    Big Stepsister Is Playing with Her Younger Stepsister
    02:02
    Big Stepsister Is Playing with Her Younger Stepsister
    SissyKanisa
    82.2K views
    Fucking in Sexy Dress with Stepbrother
    06:33
    Fucking in Sexy Dress with Stepbrother
    Crystal Phoenix
    7.2K views
    Sexy Ponny Letany Becoming More and More Feminine
    05:39
    Sexy Ponny Letany Becoming More and More Feminine
    Letany Ponny
    33.1K views
    Ladyboy Princesses cums and plays together
    23:52
    Ladyboy Princesses cums and plays together
    Ladyboy Army Raw
    140.5K views
    Satin Dress & Slut Lingerie makes CUM
    09:09
    Satin Dress & Slut Lingerie makes CUM
    Sarahsatinslut
    5.2K views
    Dominatrix Makes Hot Blonde Sissy Wear Chastity and Get Fucked
    04:17
    Dominatrix Makes Hot Blonde Sissy Wear Chastity and Get Fucked
    Bailey Wilde
    58.1K views
    Sissy secretary outfit
    05:20
    Sissy secretary outfit
    Letany Ponny
    80.2K views
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    16:04
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    Sissy Candy
    16.1K views
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    17:10
    Spandexfemboy - My BBC Dildo Filled Out My Hole
    Spandexlover89
    3.9K views
    Trans dresses as teacher, cosplay, wants to play with his students
    05:35
    Trans dresses as teacher, cosplay, wants to play with his students
    Letany Ponny
    231.7K views
    Exhibition of my big cock in the public woods in slut outfit wanks and cumshots
    05:50
    Exhibition of my big cock in the public woods in slut outfit wanks and cumshots
    Justine Love
    71.7K views
    Sexy Japanese tgirl in Bimbo dress playing with dildo
    04:20
    Sexy Japanese tgirl in Bimbo dress playing with dildo
    Letany Ponny
    115.9K views
    Princess Bunnie: Cumshot in my Favorite Dress.
    02:39
    Princess Bunnie: Cumshot in my Favorite Dress.
    Princess Bunnie
    41.3K views
    Beautiful sissy crossdresser get fucked in white dress
    03:18
    Beautiful sissy crossdresser get fucked in white dress
    Sebnem
    236.7K views
    Denim Girl
    08:12
    Denim Girl
    Melinda James
    16K views
    Sissy in teal dress and pantyhose cums hard with prostate machine
    04:55
    Sissy in teal dress and pantyhose cums hard with prostate machine
    Nylonizer
    2K views
    Kelsey Cobalt Cums in a Red Dress & Stockings
    06:41
    Kelsey Cobalt Cums in a Red Dress & Stockings
    KelseyCobalt
    75.6K views
    Short Satin Dress with Tights
    03:28
    Short Satin Dress with Tights
    Sarahsatinslut
    3.5K 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
    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
    Dominatrix Dresses Up Sissy in Dress
    02:14
    Dominatrix Dresses Up Sissy in Dress
    Bailey Wilde
    50.2K 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
    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
    Dominatrix Dresses Up and Fucks Sissy
    08:22
    Dominatrix Dresses Up and Fucks Sissy
    Bailey Wilde
    32.9K views
    Sexy chika bimbo walking around in sexy dress
    05:17
    Sexy chika bimbo walking around in sexy dress
    Letany Ponny
    178.3K 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
    Sissy Bride Riding Her Doll
    18:07
    Sissy Bride Riding Her Doll
    Sissy Candy
    6K views
    Cum with me! Dirtytalk and POV
    03:39
    Cum with me! Dirtytalk and POV
    Sissy Slut Chantal Sweet
    48.4K views
    Sexy submissive girl in sexy dress
    06:37
    Sexy submissive girl in sexy dress
    Letany Ponny
    61.6K 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
    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
    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
    Crossdresser Dressing Up for Prom Sex
    03:01
    Crossdresser Dressing Up for Prom Sex
    Bailey Wilde
    64.4K views
    Masturbation in pantyhose and leather dress (two perspectives)
    06:48
    Masturbation in pantyhose and leather dress (two perspectives)
    Nylonizer
    20.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Dressing

    • Feminization Sissy Crossdressing
    • Amateur Shemale Crossdresser Femboy
    • Crossdressers in Pretty Dresses
    • Feminized and Fucked
    • Dressing as a Girl
    • Sissy Feminization
    • Crossdresser Dress up
    • Made to Crossdress
    • Crossdressing Homemade
    • Caught Wearing Sisters Clothes
    • Sissification Process
    • Submissive Transvestite Training
    • Femboys in Lingerie
    • Sexy Dressed Like Slut
    • Transgender Skirt
    • Sissy-Virgin
    • Ladyboy Chastity
    • Frilly Panties
    • Femboy Transformation
    • Feminize

    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