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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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 Pimped Out Porn Videos

    Free Videos
    Short videos
    Photos
    Sissy
    Pimp
    Pimped Out
    Pimped Out Sissy Husbands
    Cuckold Sissy Pimped Out
    Sissy Slave Pimped Out From Mistresses
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Sissy Slave
    Amateur Sissy
    Sissy Blowjob
    Sissy Cuckold
    Sissy Gangbang
    Best Videos
    By clicking the content you will also see an ad. AD
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    684.1K views
    Sissy Pig Candii Devine Pimped Out To  A Couple
    00:40
    Sissy Pig Candii Devine Pimped Out To A Couple
    10.7K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Story of when daddy pimped me out. First week. Anal toy.
    08:50
    Story of when daddy pimped me out. First week. Anal toy.
    Sunaxfemiknulla
    17K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    284.4K views
    Small Dick Sissy Fag Jes Brinch
    06:55
    Small Dick Sissy Fag Jes Brinch
    Sissy Cindy Slut
    2.5K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    FetishEmmanuella video 2 - Garbage Prostitute - part 1
    02:01
    FetishEmmanuella video 2 - Garbage Prostitute - part 1
    Emmanuella Stavrinou
    9.9K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    FetishEmmanuella video 4 - Garbage Prostitute - part 3
    03:34
    FetishEmmanuella video 4 - Garbage Prostitute - part 3
    Emmanuella Stavrinou
    9.4K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.1M views
    FetishEmmanuella video 5 - Perverted prostitute in Cheap  Shiny Pvc Vinyl  Tattered Clothes
    01:24
    FetishEmmanuella video 5 - Perverted prostitute in Cheap Shiny Pvc Vinyl Tattered Clothes
    Emmanuella Stavrinou
    3.9K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    TV Monique - On a truck stop
    03:01
    TV Monique - On a truck stop
    GummipuppeMonique
    29.8K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    737.5K views
    Sissy bottom bitch Jes Exposed
    07:11
    Sissy bottom bitch Jes Exposed
    Sissy Cindy Slut
    2K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    917.1K views
    Sissy Monique - Showing myself in front of a porn cinema - Part 1
    02:50
    Sissy Monique - Showing myself in front of a porn cinema - Part 1
    GummipuppeMonique
    3.8K views
    Completely Submitted and Feminized
    08:12
    Completely Submitted and Feminized
    Pure Ts
    44.5K views
    FetishEmmanuella video 10 - Kinky in Thigh High Boots - part 1
    04:56
    FetishEmmanuella video 10 - Kinky in Thigh High Boots - part 1
    Emmanuella Stavrinou
    2.5K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.3M views
    Worthless CD Whore Trisha Trash Practices Her Deep Throat Skills
    03:32
    Worthless CD Whore Trisha Trash Practices Her Deep Throat Skills
    Trisha Trash
    1.9K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    FetishEmmanuella video 14 -  I am the biggest Whore POUTANA  in Cyprus part 2
    03:12
    FetishEmmanuella video 14 - I am the biggest Whore POUTANA in Cyprus part 2
    Emmanuella Stavrinou
    just added
    Teaching a Fag his place
    13:47
    Teaching a Fag his place
    Kimberhaven
    809.8K views
    Anus gets pounded hard. Cd anal fuckmachine.
    06:44
    Anus gets pounded hard. Cd anal fuckmachine.
    Sunaxfemiknulla
    536 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
    FetishEmmanuella video 13 -  I am the biggest Whore POUTANA  in Cyprus part 1
    03:12
    FetishEmmanuella video 13 - I am the biggest Whore POUTANA in Cyprus part 1
    Emmanuella Stavrinou
    just added
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    464.5K views
    I want to be your biker slut or a whore!
    06:21
    I want to be your biker slut or a whore!
    Victoria Lecherri
    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
    Faggot sissy Lauren tries out her new dildo
    03:46
    Faggot sissy Lauren tries out her new dildo
    Lauren green
    2.2K views
    Many crossdressers fucked scrnrs
    01:09:02
    Many crossdressers fucked scrnrs
    1.4M views
    FetishEmmanuella video 11 - Kinky in Thigh High Boots - part 2
    09:49
    FetishEmmanuella video 11 - Kinky in Thigh High Boots - part 2
    Emmanuella Stavrinou
    just added
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M views
    FetishEmmanuella video 12 - Vinyl Thigh High Boots -part 2
    03:51
    FetishEmmanuella video 12 - Vinyl Thigh High Boots -part 2
    Emmanuella Stavrinou
    just added
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    361.6K views
    Worthless cross dressing whore Trisha Trash can’t even wait to get her makeup on
    02:11
    Worthless cross dressing whore Trisha Trash can’t even wait to get her makeup on
    Trisha Trash
    3.2K views
    A Prostitute Offering Herself on the Street
    02:29
    A Prostitute Offering Herself on the Street
    Wesley Fudedor
    313.1K views
    Im your plaything daddy, your willing cumthirsty whore
    10:06
    Im your plaything daddy, your willing cumthirsty whore
    Sunaxfemiknulla
    1.3K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    925.8K views
    Cd ass fucked by horny terminator!
    05:42
    Cd ass fucked by horny terminator!
    Sunaxfemiknulla
    342 views
    Sissy Slut Motel
    58:39
    Sissy Slut Motel
    721.7K views
    FetishEmmanuella video 6 - Red Vinyl Skirt
    04:13
    FetishEmmanuella video 6 - Red Vinyl Skirt
    just added
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    1.8M views
    Anal cd slut fucked by machine til asspussy is drooling
    06:01
    Anal cd slut fucked by machine til asspussy is drooling
    Sunaxfemiknulla
    just added
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    103.6K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Pimped Out

    • Daddy Fucking Sissy Femboy
    • Dirty Talking Crossdresser Fucked
    • Slutty Nasty Crossdressing Gurl
    • Made to Crossdress and Suck Cock
    • Femboys in Lingerie
    • Sexy Dressed Like Slut
    • A Pretty Boy Gets Feminized
    • Degraded Sissies
    • Pimped Out
    • Secret Sissyboy
    • Sissys Get Blacked
    • Horny Femboys
    • Turning Cuck Husband Into Faggot
    • The Sissy's Future
    • Feminine Boys
    • Crossboy With Mommy Clothes
    • Caught Crossdressing by Mom
    • Chastity Gangbang
    • Extrem Crossdressers
    • Very Girly Ladyboys

    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