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 Boy Dressing Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Boy
    Dress
    Sissy Boy
    Boy Sissy
    Boy Dress
    Sissy Boys Dress Girls
    Sissy Crossdresser
    Sissy Training
    Lady Boy
    Bbc Sissy
    Sissy Feminization
    Teen Sissy Boy
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Best Videos
    By clicking the content you will also see an ad. AD
    Crossdresser in very short dresses & skirts outside
    05:10
    Crossdresser in very short dresses & skirts outside
    23.8K views
    Playing in my lovely blue dress and lingerie - Part 3
    05:15
    Playing in my lovely blue dress and lingerie - Part 3
    Rachel_biTV_uk
    40.5K 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
    asian femboy learns to be a streetwalker
    08:24
    asian femboy learns to be a streetwalker
    Niya_cd
    19.1K views
    Reina Hanno White Pearl Themed Dress & Sounding
    01:02
    Reina Hanno White Pearl Themed Dress & Sounding
    Reina Hanno
    2.7K views
    Bottom bitch Faggot! Dress up!
    10:32
    Bottom bitch Faggot! Dress up!
    Sissy Cindy Slut
    1.7K views
    cute skinny pale mistress with big cock and long cumshot in your face
    02:08
    cute skinny pale mistress with big cock and long cumshot in your face
    Nadja Cox
    13.4K views
    Let's play before our date!
    05:00
    Let's play before our date!
    Cassandra Lovit
    77.9K views
    Little Blonde Doll Teases You in a Tight Mini Dress (without Panties?)
    01:17
    Little Blonde Doll Teases You in a Tight Mini Dress (without Panties?)
    SissyfrenchDoll
    10.9K views
    cute skinny shemale summer dress huge dildo dirty ride intense cum
    02:20
    cute skinny shemale summer dress huge dildo dirty ride intense cum
    Nadja Cox
    91.2K views
    Horny bitch in luxurious black dress and highheels cums by anal fisting and tortures herself with after-cum stimulation
    14:04
    Horny bitch in luxurious black dress and highheels cums by anal fisting and tortures herself with after-cum stimulation
    Harinni
    4.5K views
    Sexy femboy in sexy dress on high heels
    05:42
    Sexy femboy in sexy dress on high heels
    Letany Ponny
    62.2K views
    Cross dressing sissy cums with dildo in her ass
    06:39
    Cross dressing sissy cums with dildo in her ass
    Vivian Villain
    29.5K views
    Sexy erotic and frivolous in red dress
    01:13
    Sexy erotic and frivolous in red dress
    CarinaDavid
    4.5K views
    Princess Bunnie: Cumshot in my Favorite Dress.
    02:39
    Princess Bunnie: Cumshot in my Favorite Dress.
    Princess Bunnie
    41.3K views
    Risky outdoor piss on picknick bench
    05:13
    Risky outdoor piss on picknick bench
    Annemieke26
    22K views
    Denim Girl
    08:12
    Denim Girl
    Melinda James
    16K views
    Sissy getting fucked in wedding dress
    01:31
    Sissy getting fucked in wedding dress
    148.2K views
    Pink Sissy Maid Candy Is Locked Onto Her Dildo Stand and Rides Her Pole
    40:34
    Pink Sissy Maid Candy Is Locked Onto Her Dildo Stand and Rides Her Pole
    Sissy Candy
    1.9K views
    misr4 - Fleshlight double cumshot
    08:03
    misr4 - Fleshlight double cumshot
    misr4
    17.2K views
    Beautiful sissy crossdresser get fucked in white dress
    03:18
    Beautiful sissy crossdresser get fucked in white dress
    Sebnem
    236.7K views
    Crossdresser in very short dresses & skirts outside
    05:07
    Crossdresser in very short dresses & skirts outside
    45.1K views
    My new short. tight dress turns me on so much i can't hold back my erection, so I decided to fuck and jerk off until I cum
    20:41
    My new short. tight dress turns me on so much i can't hold back my erection, so I decided to fuck and jerk off until I cum
    Bbrgurl
    33.4K views
    Showing myself off in my red bodycon dress. I get myself a little worked up again.
    06:27
    Showing myself off in my red bodycon dress. I get myself a little worked up again.
    JessicaXD
    1.8K views
    I'm going to take it off today, I'm going to take off my clothes and get naked
    06:21
    I'm going to take it off today, I'm going to take off my clothes and get naked
    harucoco
    5K views
    Sissys deepthroat training on a BBC
    01:59
    Sissys deepthroat training on a BBC
    WaifuStuff
    71.9K views
    Slut in dress gets cum in her mouth POV - Laylacross
    10:17
    Slut in dress gets cum in her mouth POV - Laylacross
    84.8K views
    My transparent dress in 3 different suspender stockings
    05:12
    My transparent dress in 3 different suspender stockings
    Loreleyadd
    29K 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
    German sissy in vinyl outfit
    01:31
    German sissy in vinyl outfit
    Furtx
    22.5K views
    Sissy Sophie trains her hole against the wall
    07:11
    Sissy Sophie trains her hole against the wall
    Sophie Valentine
    71.4K views
    Shemale in leather dress gets sucked before fucking her male
    08:22
    Shemale in leather dress gets sucked before fucking her male
    TS Latex
    36.4K views
    Jude as Sissy Dress Promoting Model At Newly Opened Store
    05:45
    Jude as Sissy Dress Promoting Model At Newly Opened Store
    Asura
    4K views
    How Should a Sissy at Work Dress
    03:26
    How Should a Sissy at Work Dress
    59.7K views
    Putting my gorgeous dress on over my luxury lingerie in the woods
    05:07
    Putting my gorgeous dress on over my luxury lingerie in the woods
    Rachel_biTV_uk
    24.8K views
    Sexy Crossdresser kellycd2022 in pink pvc outfit and black fishnets
    19:56
    Sexy Crossdresser kellycd2022 in pink pvc outfit and black fishnets
    Kellycd2022
    6.2K views
    A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out.
    14:30
    A horny slut with perfect body in tight dress and black pantyhose tries new sex toys alone and prepares to go out.
    Harinni
    13.2K views
    Son caught dad in moms clothes and blacmailed him (pov roleplay naughty talk)
    08:51
    Son caught dad in moms clothes and blacmailed him (pov roleplay naughty talk)
    MamaZSekretem
    29.9K views
    Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy
    06:27
    Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy
    Nicole Nicolette
    12.2K views
    My conversation with a guy
    01:42
    My conversation with a guy
    Vladasexytrans
    62.8K views
    Nancy's New Boyfriend
    07:38
    Nancy's New Boyfriend
    Nancy Rose
    28.9K views
    mistress sexy yellow outfit dirtytalk huge cock cumshot
    02:55
    mistress sexy yellow outfit dirtytalk huge cock cumshot
    Nadja Cox
    106K views
    Tranny Femdom SPH! Cockless chastity slave is transformed into a two-hole slut!
    01:17
    Tranny Femdom SPH! Cockless chastity slave is transformed into a two-hole slut!
    TV_Helena
    14.1K views
    Sexy cd sissy slut secret night away from wife dresses and fucks to sissygasm
    08:03
    Sexy cd sissy slut secret night away from wife dresses and fucks to sissygasm
    OneWhoHasFun
    10.6K views
    Sexy Crossdresser kellycd2022 in black sexy seamless pantyhose black dress and mules on a cold morning
    10:25
    Sexy Crossdresser kellycd2022 in black sexy seamless pantyhose black dress and mules on a cold morning
    Kellycd2022
    4.7K views
    Vladasexytrans Wild Anal Play in Black Dress and in Black Stockings
    14:00
    Vladasexytrans Wild Anal Play in Black Dress and in Black Stockings
    Vladasexytrans
    41.1K views
    FetishEmmanuella video 4 - Garbage Prostitute - part 3
    03:34
    FetishEmmanuella video 4 - Garbage Prostitute - part 3
    Emmanuella Stavrinou
    10.3K views
    • Back
    • 1
    • ...
    • 6
    • 7
    • 8
    • 9
    • 10
    • ...
    • 80
    • Next

    Searches Related to Sissy Boy Dressing

    • Bitch Handcuffed
    • Granny Chubby
    • Gender Bender
    • Five Star Hotel Porn
    • Kim Kardashian Xnxx
    • Sissys
    • Bobstgirls
    • Sassy Kashi
    • Retro 1900 1910 1920 1930 1940
    • Sissyslut Harley
    • Stunning
    • Sissyboy Shannon
    • Boys Will Be Girls
    • Sleazy Sleazerson
    • High Class MILF
    • Bimbo Slut
    • Shemale Leggings
    • Horny T-Slut
    • Belly Down Anal
    • Trannylea
    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