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
    -50%
    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
    -60%
    Dating
    Subscriptions
    • Upload
    50% OFF Tokens for NY Ring in 2026 with the right company on xHamsterLive!
    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
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Dressing Up Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Dress
    Dress up
    Sissy Instructions JOI Dress up
    Sissy Faggot Playing Dress up
    Sissy Maid Dress up for Mistress
    Dominatrix Dresses up Sissy in Dress
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Sissy Fucked
    Sissy Compilation
    Amateur Sissy
    Sissy Blowjob
    Sissy Slave
    Sissy Cuckold
    Best Videos
    By clicking the content you will also see an ad. AD
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2M views
    Sissy dressing up slowly in pastel-colored bedroom
    07:52
    Sissy dressing up slowly in pastel-colored bedroom
    Crossdresserkitty
    1.1K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Dressing up as a Japanese schoolgirl
    05:16
    Dressing up as a Japanese schoolgirl
    Menaiisd
    58.4K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    674.4K 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
    2K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    Crossdresser Dressing Up for Prom Sex
    03:01
    Crossdresser Dressing Up for Prom Sex
    Bailey Wilde
    63.5K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2M views
    SisK CD in purple EP2 dressing up sexy silky panties.
    11:25
    SisK CD in purple EP2 dressing up sexy silky panties.
    SissyKanisa
    45.7K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    MissyNylonLeggs Alone in a Motel Dressing Up
    03:05
    MissyNylonLeggs Alone in a Motel Dressing Up
    MissyNylonLeggs
    2.9K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    SisK dressing up pink satin nightgown
    13:00
    SisK dressing up pink satin nightgown
    SissyKanisa
    19.9K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    271.7K views
    Transvestite slut I love dressing up as a girl and being an obedient little slut.
    08:03
    Transvestite slut I love dressing up as a girl and being an obedient little slut.
    Kelynxxx
    2.2K views
    Crossdresser shop owner gets fucked by a man in the shop
    13:00
    Crossdresser shop owner gets fucked by a man in the shop
    WanidaCrossdresser
    330.7K views
    Spun sissy boy trying on panties n dressing up.
    04:15
    Spun sissy boy trying on panties n dressing up.
    8.9K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    Video of a demon cosplay dressing up as a woman quietly masturbating
    01:50
    Video of a demon cosplay dressing up as a woman quietly masturbating
    Chika
    1.2K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    I love dressing up in pink! Wanna see my pinky?
    05:27
    I love dressing up in pink! Wanna see my pinky?
    Melinda James
    3K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    450.5K views
    Cock sucking, Dressing Up and Cumming with Dee Angels....cum on over...
    43:04
    Cock sucking, Dressing Up and Cumming with Dee Angels....cum on over...
    DeeAngels
    9.7K views
    SISSY TRANSFORMATION
    11:07
    SISSY TRANSFORMATION
    642.6K views
    A video of a blindfolded step sister dressing up as a woman masturbating while streaming
    08:10
    A video of a blindfolded step sister dressing up as a woman masturbating while streaming
    Chika
    1.4K views
    Two Sexy Sissy Do Deep Throat BlowJob
    08:25
    Two Sexy Sissy Do Deep Throat BlowJob
    IskraElectrical49
    103.4K views
    Dressing up and fucking myself in a wet hole while my dick pumps
    02:44
    Dressing up and fucking myself in a wet hole while my dick pumps
    New_Cross_Marta
    1.8K views
    They made him look like a women and dress him up
    52:52
    They made him look like a women and dress him up
    Alfacontent World
    114.3K views
    I enjoy dressing up as a sexy girl and cumming feeling like a bitch
    08:00
    I enjoy dressing up as a sexy girl and cumming feeling like a bitch
    Anaisfeet35
    2.1K views
    Dress Up Sissy Costume Tasks
    10:49
    Dress Up Sissy Costume Tasks
    Natalie Napoli
    19.1K views
    Video of a blonde beauty dressing up as a woman masturbates quietly
    01:36
    Video of a blonde beauty dressing up as a woman masturbates quietly
    Chika
    1.6K views
    Tv is for Sissies (Full Video)
    56:35
    Tv is for Sissies (Full Video)
    608.4K views
    Sissy Caption - It's not gay if you dress up like a girl
    01:00
    Sissy Caption - It's not gay if you dress up like a girl
    639.2K views
    Sissy Femboy wears various sexy women clothes
    05:11
    Sissy Femboy wears various sexy women clothes
    34.4K views
    Princess Bunnie: Pin-up Masturbation and Cumshot
    02:09
    Princess Bunnie: Pin-up Masturbation and Cumshot
    Princess Bunnie
    15K views
    I finally let my stepsis fuck my trans pussy
    05:30
    I finally let my stepsis fuck my trans pussy
    CutePinkUnicorn
    586.3K 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
    25.6K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    448.8K views
    boys are brothers and dress up like sissy girls and CUM
    24:54
    boys are brothers and dress up like sissy girls and CUM
    Nikki Ladyboys
    705.8K views
    Sissy Slut Motel
    58:39
    Sissy Slut Motel
    712.5K views
    Princess Bunnie: Crossdresser MILF masturbating
    07:01
    Princess Bunnie: Crossdresser MILF masturbating
    Princess Bunnie
    40.9K views
    Your Little Fag Sissy Princess
    11:31
    Your Little Fag Sissy Princess
    Natalie Napoli
    22.1K 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
    270.3K views
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    08:12
    Trans Porn Trans Girl Cumming While Creampied by a Huge Uncut Cock
    nbnabunny
    1.6M views
    Dress up time for you
    06:35
    Dress up time for you
    73.6K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    342.5K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Dressing Up

    • Feminization Sissy Crossdressing
    • Dressing as a Girl
    • Crossdresser Dress up
    • Sexy Dressed Like Slut
    • Femboy Sissification
    • Sissyfication Process
    • Feminized by Wife
    • Femboys in Lingerie
    • Femdom Crossdress
    • First Time Crossdressing
    • Man Transformed Into Woman
    • Feminine Boys
    • Crossdresser Makeup
    • Femboy Dress
    • Secret Sissyboy
    • Crossdressing Feeling Girly
    • Feminize Yourself
    • Men Dressed as Women
    • Tranny Short Skirt
    • Putting on Chastity

    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