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
    • Black
    • Big Cock
    • 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
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy In Trouble Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos

    Did you mean sissy in double?

    Best Videos
    By clicking the content you will also see an ad. AD
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Sissy Maids in Trouble part 3
    00:25
    Sissy Maids in Trouble part 3
    Shinys Bound SluTS
    19.7K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.7M views
    Sissy Maids in Trouble 2
    00:24
    Sissy Maids in Trouble 2
    Shinys Bound SluTS
    21.2K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.5M views
    Double Trouble on Eid He Camed 2 Times on My Hijab Back to Back
    21:00
    Double Trouble on Eid He Camed 2 Times on My Hijab Back to Back
    Stripchat official
    651.3K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    First sissy clip try! My subscriber sent me a huge dildo and fufu clip so I had trouble putting on as it kept getting erect.
    16:20
    First sissy clip try! My subscriber sent me a huge dildo and fufu clip so I had trouble putting on as it kept getting erect.
    Harinni
    55.6K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    963.5K views
    Sissy maid Lilith gets out of trouble with a guest
    08:12
    Sissy maid Lilith gets out of trouble with a guest
    Pure Ts
    30K 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
    Sissy Training 202 Double Trouble
    07:09
    Sissy Training 202 Double Trouble
    FapHouse
    1.9K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2M views
    Getting out of trouble by giving up the ass
    08:12
    Getting out of trouble by giving up the ass
    Pure Ts
    17.6K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    Trouble Maker
    24:58
    Trouble Maker
    Shelly Robertss
    8.6K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    300.5K views
    The trouble be me.
    01:08
    The trouble be me.
    garters3350
    1.1K views
    Lovely young girl is a shemale with big cock
    08:11
    Lovely young girl is a shemale with big cock
    10.8M views
    Tranny Trouble 1!
    03:08
    Tranny Trouble 1!
    10K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Tranny Trouble 2!
    01:55
    Tranny Trouble 2!
    6.8K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    FapHouse
    2.6M views
    Double Trouble Sissy Ass Tiffany Ciskiss Gapping Ass On Xxl Extrem Anal Dildo
    20:03
    Double Trouble Sissy Ass Tiffany Ciskiss Gapping Ass On Xxl Extrem Anal Dildo
    FapHouse
    11.7K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    704K views
    Sissy getting ready to sleep, but is troubled
    20:43
    Sissy getting ready to sleep, but is troubled
    Michelle Nylon 81
    17K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    840.1K views
    Everything I've done I've done has been so good at it I've had a lot of trouble with the game and I've come out on top
    54:05
    Everything I've done I've done has been so good at it I've had a lot of trouble with the game and I've come out on top
    Reynaldo6
    1.5K views
    Black tgirl with giant tool fucking a white ass fat faggot
    11:38
    Black tgirl with giant tool fucking a white ass fat faggot
    Latina Tranny
    1.6M views
    Sissy Sluts Toilet Troubles
    12:49
    Sissy Sluts Toilet Troubles
    Derek6699
    28.1K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.8M views
    Legs that lead to trouble
    06:36
    Legs that lead to trouble
    Crossdresserkitty
    934 views
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    10:54
    He Tears His Cute Trans Roommate's Pantyhose To Bang Her
    Devils tgirls
    6.2M views
    Spidey in Trouble
    03:25
    Spidey in Trouble
    TiffanyWarmer
    32.3K views
    Don't do this to me! I do not like it!
    03:01
    Don't do this to me! I do not like it!
    742.3K views
    Trannies in Trouble
    13:28
    Trannies in Trouble
    220.9K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    FapHouse
    1.2M views
    Mili In Trouble Forest
    04:58
    Mili In Trouble Forest
    Dogazy
    6.9K views
    shemale dresses sissy to fuck
    16:14
    shemale dresses sissy to fuck
    2.1M views
    Shemale Student In Trouble, Mr. Paris Helps
    07:00
    Shemale Student In Trouble, Mr. Paris Helps
    106.5K views
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    12:33
    Veronica Leal Surprises Stacy Cruz with Her FUTA Dick and Gets Her Tight Ass Destroyed - FULL SCENE
    Futanari XXX
    21.7M views
    Getting home Late Nikki Montero is in trouble
    04:27
    Getting home Late Nikki Montero is in trouble
    She Lesbian POV
    77.9K views
    Feminized for Girls Night Out (Full Movie)
    23:39
    Feminized for Girls Night Out (Full Movie)
    Onlyfans
    557.2K views
    Michelle in trouble
    01:28
    Michelle in trouble
    30.5K views
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    13:12
    Cuckold husband gets hard painful fucking from his wife's bull lover hard humiliation CD Sissy Crossdresser Fiona Fortune
    Fiona Fortune
    221.7K views
    Shemale Student In Trouble, Mr. Paris Helps
    06:11
    Shemale Student In Trouble, Mr. Paris Helps
    44.3K views
    Indian Best Threesome Sex! Fuck Both of us
    22:48
    Indian Best Threesome Sex! Fuck Both of us
    indianXworld
    22.3M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next
    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