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
    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
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Cuckold First Time Bbc Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    You switched to shemale orientation. Do you want to keep searching in the straight section?
    Sissy
    Bbc
    Cuckold
    First
    Time
    First Time Sissy
    Bbc Sissy Cuckold
    First Time BBC
    Bbc Sissy
    First Time
    Sissy Cuckold
    First BBC
    Sissy Time
    Sissy Crossdresser
    Sissy Training
    Sissy Feminization
    Sissy Husband
    Sissy Chastity
    Young Sissy
    Sissy Fucked
    Best Videos
    By clicking the content you will also see an ad. AD
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    1.9M views
    Instinct Unleashed gameplay parte 1
    35:13
    Instinct Unleashed gameplay parte 1
    jackyxxx
    10.6K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    06:52
    Slutt Crossdresser tells bbc cuckold story and plays it out. The bbc fucks his hot white wife
    MadisonCD2025
    824 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
    Asian Satanic Sissy - First Time BBC Fuck and Cum On Face
    06:04
    Asian Satanic Sissy - First Time BBC Fuck and Cum On Face
    52.5K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    19:58
    MY FIRST TIME FUCK BEAUTIFUL SHEMALE ON UPSTAIRS
    Altmodelbox
    23.3K views
    You Are Just a Hole - Variety Itsol
    10:46
    You Are Just a Hole - Variety Itsol
    Rodrigo Amor
    1.9M views
    It's getting horny. For the first time I took my ass a little harder.2024
    08:50
    It's getting horny. For the first time I took my ass a little harder.2024
    7.5K 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
    218.3K views
    BBC Two Huge Cocks for Tight Little European Trans Ass
    08:12
    BBC Two Huge Cocks for Tight Little European Trans Ass
    Trans and Co
    261K views
    First time cuck sissy record for her mistress
    46:52
    First time cuck sissy record for her mistress
    Assexploringmachin
    2.3K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    798.4K views
    Wife let me wear her clothes and sissygasm
    06:24
    Wife let me wear her clothes and sissygasm
    OneWhoHasFun
    29.6K views
    BBC Fucks a Slutty Crossdresser Without Limits
    32:44
    BBC Fucks a Slutty Crossdresser Without Limits
    Trans and Co
    384.7K views
    Olivia Puts Chastity Cage on My Cock
    05:23
    Olivia Puts Chastity Cage on My Cock
    Asura
    4.2K views
    Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    09:55
    Submissive Sissy crossdresser fucked by BBC - she is a bitch4
    Rozebella
    702.5K views
    Be Mine Only Mine
    03:24
    Be Mine Only Mine
    Stripchat official
    2K views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    What A Convenient Trick by Futanari Kate
    05:14
    What A Convenient Trick by Futanari Kate
    Asura
    2.9K views
    Daddy loves to wreck my asshole in chastity
    06:24
    Daddy loves to wreck my asshole in chastity
    missangell_
    479.4K views
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    06:02
    Horse cock in big white virgin asshole, first try, lubed and ready, but still virgin pussy is tight but juicy
    21K views
    BBC Addiction - MY wife lovec big black cock
    15:05
    BBC Addiction - MY wife lovec big black cock
    tattooedb
    48.3K views
    Trip Of A Life Time
    10:56
    Trip Of A Life Time
    Asura
    2.8K views
    Her ass can fit all my big black cock so good
    06:21
    Her ass can fit all my big black cock so good
    MrNastyXavier
    1.8M views
    Crossdresser Cdmichelle putting on Lace Panties & Lingerie
    06:02
    Crossdresser Cdmichelle putting on Lace Panties & Lingerie
    CdMichelleX
    1.5K views
    Gangbang and double anal for a slutty trans
    01:00:27
    Gangbang and double anal for a slutty trans
    parisjango
    1.9M views
    Eruption imminent gameplay part 20
    05:59
    Eruption imminent gameplay part 20
    Amaran
    2.9K views
    Your little bitch wants hot cum inside her tight and dirty asshole
    06:50
    Your little bitch wants hot cum inside her tight and dirty asshole
    missangell_
    766.7K views
    Crossdresser Cdmichelle Super Cum Shot Licking up PreCum
    07:11
    Crossdresser Cdmichelle Super Cum Shot Licking up PreCum
    CdMichelleX
    1.9K views
    Guy loses bet turns into sissy CD giving blowjob
    04:52
    Guy loses bet turns into sissy CD giving blowjob
    1.3M views
    Sissy Slut White Body Big Butt Big Ass Sexy Crossdresser
    07:27
    Sissy Slut White Body Big Butt Big Ass Sexy Crossdresser
    Crossdresserkitty
    4.3K views
    Sissy Gets Used By Dominant Couple
    08:42
    Sissy Gets Used By Dominant Couple
    Third sex XXX
    1.2M views
    SLUTTY TRANNY JSSEMONTZ puts on LINGERIE and sucks a huge bbc for her first time
    02:36
    SLUTTY TRANNY JSSEMONTZ puts on LINGERIE and sucks a huge bbc for her first time
    JsseMontz
    107.7K views
    She loves to be my favorite fucktoy in bareback
    05:36
    She loves to be my favorite fucktoy in bareback
    MrNastyXavier
    2M views
    (Part 2) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    08:14
    (Part 2) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    MaureenNadh
    78.9K views
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    12:54
    GenderX - Wife Wants Husband To Fuck Her Trans Friend
    GenderX
    2.7M views
    My first time Giving a Blowjob and Eating Cum with a BDSM blind mask
    10:49
    My first time Giving a Blowjob and Eating Cum with a BDSM blind mask
    fermerino
    5.1K views
    Pretty Blonde Femboy Fucked by BBC
    08:01
    Pretty Blonde Femboy Fucked by BBC
    Trans and Co
    207.7K views
    Veronica Sanders fucking a guy for the first time and cumming on his face
    06:05
    Veronica Sanders fucking a guy for the first time and cumming on his face
    Veronica Sanders
    54.4K views
    TS Babysitter gets a Spooky Interracial Gangbang
    19:33
    TS Babysitter gets a Spooky Interracial Gangbang
    Kapri Sun
    371.6K views
    (Part 1) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    09:06
    (Part 1) First Time Tasting My Own Cum And Drinking Piss, Cum On Food Fetish, Asian Transgender Trap Shemale
    MaureenNadh
    27.9K views
    Sissy Hailey Doll gets her holes ruined by BBC😈
    02:05
    Sissy Hailey Doll gets her holes ruined by BBC😈
    Sissy Haileydoll
    666K views
    The First Time Married to a Trans Girl
    35:23
    The First Time Married to a Trans Girl
    EmmaInkTrans
    7.7K views
    Girl forgot to tell her Tinder date that she’s Trans
    07:22
    Girl forgot to tell her Tinder date that she’s Trans
    JsseMontz
    638.7K views
    My first time fucking trans man
    05:33
    My first time fucking trans man
    Nathalia Fontes
    139.9K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Cuckold First Time Bbc

    • Locked Sissy Cock
    • Bbc Breeds Fat CD Pussy
    • First Time Being Fucked as Crossdresser
    • Schoolgirl Tranny Fucking Hard
    • Cute Trap Wank and Cum
    • Crossdressing Husband Caught by Rides
    • Crossdressers Kirsty in an Orgy
    • Bisexual Cuckold Femboy
    • A Pretty Boy Gets Feminized
    • Gay sissyboy Leaked
    • Mature Crossdresser Wants It Bad
    • White Femboys Are so Submissive
    • Sissy Sucking My Cock
    • Sexy Femboy Dancing Sisdon
    • Gothic Bimbo
    • Crossdress Sex Tgp
    • Dildo Sissygasm
    • Amateur White Trans BBC
    • Sissyfication Process
    • Sissycross Anna
    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