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
    +14 MONTHS FREE 😱 🍾 🥂 Happy New Year 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 Caught Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Caught
    Caught Sissy
    Sissy Caught Crossdressing Hotel
    Sissy Gets Caught Caption Story
    Crossdresser Sissy Caught Mom and Dad
    Sissy Caption Sissy Caught by Roommate
    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
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.2M views
    Sissy Caption - Sissy caught by roommate
    01:00
    Sissy Caption - Sissy caught by roommate
    269K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2M views
    Sissy caught gooning by room mates friend gives blowjob and takes it in the ass
    12:54
    Sissy caught gooning by room mates friend gives blowjob and takes it in the ass
    JaymieJameson
    7.9K views
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.8M views
    Sissy caught riding Big Dildos and caged into chastity - teaser
    01:25
    Sissy caught riding Big Dildos and caged into chastity - teaser
    Sissy Slut Chantal Sweet
    32.7K views
    dominant stepmom helps out her sissy slave
    05:59
    dominant stepmom helps out her sissy slave
    Pure Ts
    342.5K views
    Sissy caught on camera using her aunt clothes
    04:27
    Sissy caught on camera using her aunt clothes
    MelanieR
    15.5K views
    Male to female gender transformation smoking whore
    16:00
    Male to female gender transformation smoking whore
    674.4K views
    Bubblebutt sissy caught in alley
    00:42
    Bubblebutt sissy caught in alley
    TeenBubbleButtSissy
    15.4K views
    Sissy cum dump compilation
    28:49
    Sissy cum dump compilation
    2.6M views
    Sissy caught and filmed walking in minishort on public beach
    00:09
    Sissy caught and filmed walking in minishort on public beach
    8.1K views
    I turned my straight roommate intro trans wife
    05:20
    I turned my straight roommate intro trans wife
    CutePinkUnicorn
    450.5K views
    Exposed sissy caught
    00:51
    Exposed sissy caught
    3.8K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3M views
    Princesskitti3 Gets Caught Using Fuck Machine and Fucked Instead by Gwen_nova
    20:02
    Princesskitti3 Gets Caught Using Fuck Machine and Fucked Instead by Gwen_nova
    PrincessKitti3
    160.5K views
    Sissy CD sucks and is fucked
    08:25
    Sissy CD sucks and is fucked
    1.4M views
    Riding dildo on bike in public - caught
    04:05
    Riding dildo on bike in public - caught
    Asiansissypublic
    45.4K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    883.3K views
    I Caught Him Fucking Me, a Trans Girl, on Camera!
    08:12
    I Caught Him Fucking Me, a Trans Girl, on Camera!
    Gray Perrier
    17.9K views

    Relevant Short videos

    Thrilling moment from "Sissy caught gooning by room mates friend gives blowjob and takes it in the ass"
    Thrilling moment from "Sissy caught gooning by room mates friend gives blowjob and takes it in the ass"
    JaymieJameson
    1.1K views
    Unforgettable moment from "Sissy caught gooning by room mates friend gives blowjob and takes it in the ass"
    Unforgettable moment from "Sissy caught gooning by room mates friend gives blowjob and takes it in the ass"
    JaymieJameson
    665 views
    Naked Sissy Caught Walking in Alley
    Naked Sissy Caught Walking in Alley
    Scrap D Flasher
    1.2K views
    Shemale strokes fat cock in public hotel hallway
    Shemale strokes fat cock in public hotel hallway
    Janice Renee
    97.2K views
    tgirl caught masturbating her thick girl cock next to busy street
    tgirl caught masturbating her thick girl cock next to busy street
    Janice Renee
    54.7K views
    femboy milking prostate
    femboy milking prostate
    boobyb0y
    19.3K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    706.7K views
    Kira caught during self-bondage
    02:45
    Kira caught during self-bondage
    Twistedrama
    40.9K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.4M views
    Trap Femboy caught using toys by BBC housemate and gets bred
    04:09
    Trap Femboy caught using toys by BBC housemate and gets bred
    Maskedloki9
    404K views
    Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    271.7K views
    Bad Girl Kylie Caught Smoking
    05:23
    Bad Girl Kylie Caught Smoking
    Darkfetish2k
    6.4K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.2M views
    German amateur 18yo tranny next door do homemade anal porn
    07:45
    German amateur 18yo tranny next door do homemade anal porn
    Transen-von-Nebenan
    708.1K views
    Sissyfication
    43:09
    Sissyfication
    1M views
    I touched a stranger's dick in a gay bar he wet my pantyhose with his cum
    05:08
    I touched a stranger's dick in a gay bar he wet my pantyhose with his cum
    cd_aysemmm
    25.4K 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
    Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
    05:07
    Slut Beril Who Trains At Home Goes For A Walk Outside Public +18 Coward
    Usaberilx
    11.3K views
    Never Expecting to Be a Sexy Girl
    08:12
    Never Expecting to Be a Sexy Girl
    Pure Ts
    448.8K views
    He fucks my ass in the lot
    06:34
    He fucks my ass in the lot
    Valera Toro
    9.7K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    91.5K views
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    11:21
    Pink Sissy Maid Caught Dressing and Playing and Has a Sissygasm Riding Her Doll
    Sissy Candy
    49.3K views
    Sissy Joyce - A real life sissy slave
    01:16
    Sissy Joyce - A real life sissy slave
    Sissy Joyce
    673.9K views
    Public exposure on bike in public showing butt plug
    02:31
    Public exposure on bike in public showing butt plug
    Asiansissypublic
    10.8K views
    family fun 1.mp4
    13:05
    family fun 1.mp4
    1.7M views
    Massive dildo stuffed up ass and exposed in public
    01:34
    Massive dildo stuffed up ass and exposed in public
    Asiansissypublic
    5.5K views
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    01:17
    Tranny girl used rough in public! Clothes ripping! Mouthfuck! Deepthroat! Assfuck! Facial!
    Allmylinks
    68.8K views
    Trans Stepsister Caught Jerking off & Fucking Her Ass with a Dildo
    10:28
    Trans Stepsister Caught Jerking off & Fucking Her Ass with a Dildo
    Eris Jolie
    38.4K views
    Lily DeMure Blowjob & Doggy
    11:54
    Lily DeMure Blowjob & Doggy
    1.6M views
    Butt plug and filled condoms in public riding a bike - caught!
    03:12
    Butt plug and filled condoms in public riding a bike - caught!
    Asiansissypublic
    5.5K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    191.5K views
    CAUGHT PUBLIC SISSY DILDO, LIMP CUMSHOT, STRANGER WATCHES cd
    06:35
    CAUGHT PUBLIC SISSY DILDO, LIMP CUMSHOT, STRANGER WATCHES cd
    CindieLove
    111.2K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    359.3K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Caught

    • Real Caught
    • Sissy Femboy Fucked
    • Straight Guy Tricked
    • Sissyfication Process
    • First Time Crossdressing
    • Secret Sissyboy
    • Crossdresser Sucks Cock Humiliated
    • Wife Catches Husband
    • Dirty Crossdressers Slut
    • Lost a Bet
    • Whored Out
    • Accidentally Cumming
    • Degraded Sissies
    • Sissyfist Nick Leaked
    • Accidental Erection
    • Crossdreser Sex
    • Sissypink Boy
    • Tricked Older Straight Man
    • Feminine Boys
    • Cuckold Humiliation

    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