PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition

    Crossdress Bet Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Crossdress
    Lost Bet
    Amateur Crossdress
    Crossdress Blackmail
    Crossdress Gangbang
    Crossdress Lingerie
    Crossdress Fuck
    Crossdress Orgy
    Crossdress Sex
    Crossdress Fucked
    Femdom Crossdress
    Crossdress Husband
    Sissy Crossdress
    Crossdress Public
    Crossdress Cum
    Japanese Crossdress
    Crossdress Training
    Mature Crossdress
    Crossdress Blowjob
    Asian Crossdress
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • The Lost Bet
      01:28
      The Lost Bet
      Sissy Shelby Kiss
      8.4K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M views
    • The Bet
      05:04
      The Bet
      Athena Apollonia
      5K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      822K views
    • Cd slave bet
      01:43
      Cd slave bet
      Mika
      1.4K views
    • I'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      2M views
    • Dumb bet
      01:00
      Dumb bet
      476.4K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Bet  sister
      00:51
      Bet sister
      202.9K views
    • FEMBOYISH - Mischievous Petite Femboy In Lingerie Cyrus Stark Teases Horny Roommate Drake Von
      12:31
      FEMBOYISH - Mischievous Petite Femboy In Lingerie Cyrus Stark Teases Horny Roommate Drake Von
      ADULTTIMEGAY
      608.3K views
    • I Bet you want
      03:48
      I Bet you want
      Ts Eve
      351.6K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.1M views
    • Sissy caption - your best friend bets her ass can make you cum
      05:42
      Sissy caption - your best friend bets her ass can make you cum
      Midorin Nino
      29.7K 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
      FapHouse
      1.6M views
    • Brand New Asian Femboy Lauren Carter Loses Bet & Dresses up
      07:08
      Brand New Asian Femboy Lauren Carter Loses Bet & Dresses up
      Andre Stone
      5K views
    • Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      08:12
      Picking up a Sexy Tgirl off the Streets and Giving Her My BBC
      TGIRLPLAYHOUSE
      2.3M views
    • Video Game Bet With Your Stepsister Melissa Masters: GFE
      03:12
      Video Game Bet With Your Stepsister Melissa Masters: GFE
      Melissa Masters
      38.2K 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
      648.5K views
    • Guy Loses The Bet and Has to Share His Sexy TS Girlfriend Andreza Fernandes
      08:04
      Guy Loses The Bet and Has to Share His Sexy TS Girlfriend Andreza Fernandes
      Dream Tranny
      56.2K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      linktree
      521.9K views
    • I bet I know where you want to cum
      01:21
      I bet I know where you want to cum
      alice_jones
      4K views
    • Many crossdressers fucked scrnrs
      01:09:02
      Many crossdressers fucked scrnrs
      1.4M views
    • I bet you wish you had a girlfriend like me
      04:40
      I bet you wish you had a girlfriend like me
      Goergina Foxx
      5.1K views
    • Walking Naked in Heels. Confident Tgirl Tease You
      05:23
      Walking Naked in Heels. Confident Tgirl Tease You
      FapHouse
      100.5K views
    • You Lost Your Bet with Your Boss Bella Roma
      01:18
      You Lost Your Bet with Your Boss Bella Roma
      Bella Roma
      2.9K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • I am a very horny maid right now, I bet you would love to lift up my cute fluffy petticoat and have your way with me before I do
      02:28
      I am a very horny maid right now, I bet you would love to lift up my cute fluffy petticoat and have your way with me before I do
      JessicaXD
      1.1K views
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      349.3K views
    • Ruckus Bets on Iris Indigo's Tight Ass!
      02:17
      Ruckus Bets on Iris Indigo's Tight Ass!
      139.9K views
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.7M views
    • I will do my bets to get your job back!
      06:15
      I will do my bets to get your job back!
      10.3K views
    • Two Sexy Sissy Do Deep Throat BlowJob
      08:25
      Two Sexy Sissy Do Deep Throat BlowJob
      IskraElectrical49
      140.6K views
    • Am I making you touch yourself? I bet you are horny af watching me tease in my black lace dress, fully fashioned stockings
      01:16
      Am I making you touch yourself? I bet you are horny af watching me tease in my black lace dress, fully fashioned stockings
      JessicaXD
      763 views
    • Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      29:33
      Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
      Ria_Bentley
      2.6M views
    • Curvy Futa PAWG Lost a Bet in the Caseno - She Pays with Her Ass - Sassycomics.mp4
      10:11
      Curvy Futa PAWG Lost a Bet in the Caseno - She Pays with Her Ass - Sassycomics.mp4
      FapHouse
      4.3K views
    • Dating a mature crossdresser
      08:12
      Dating a mature crossdresser
      Pure Ts
      254K views
    • I bet you would love coming to the office if I showed up
      01:26
      I bet you would love coming to the office if I showed up
      JessicaXD
      325 views
    • crossdresser
      18:32
      crossdresser
      513.3K views
    • Sexy Bella loses a bet...and her clothes...
      05:33
      Sexy Bella loses a bet...and her clothes...
      8.2K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.1M views
    • Pretty blonde shemale Adriana Shelldan bet banged by horny jockstrap near the pool
      22:23
      Pretty blonde shemale Adriana Shelldan bet banged by horny jockstrap near the pool
      Shemales Tales
      2.9K 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
      352K views
    • Do you wish to fuck me dressed like this? I bet you do
      00:44
      Do you wish to fuck me dressed like this? I bet you do
      JessicaXD
      415 views
    • Lily DeMure Blowjob & Doggy
      11:54
      Lily DeMure Blowjob & Doggy
      1.6M views
    • I BET WE CAN HIDE IT
      01:26
      I BET WE CAN HIDE IT
      MillytheMinx
      18.3K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      700.3K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Searches Related to Crossdress Bet

    • Caught Crossdressing and Fucked
    • Sissy Crossdresser Confessions
    • Crossdressers First BBC
    • Femboy
    • Secret Sissyboy
    • Amateur Crossdress
    • Femboys in Lingerie
    • Boy Dressed as Girl
    • Sissys Get Blacked
    • Cute Traps for Straight Guys
    • Femboygirlfriend
    • Crossdressing Daddies
    • Guy Sucks Sissy's Cock
    • Wife Catches Husband With Trans
    • Sloppy Toppy
    • Transsexual Surprise
    • Cuck Humiliation
    • Sissy Crossdresser
    • Cross Dresser Cum
    • Male to Female Transformation Fantasy
    Monetize your content
    Become a creator
    xHamster
    • About us
    • 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
    Earn money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    © 2026 xHamster - Free porn videos.
    Desktop 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