PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    BLUE MONDAY SALE 💛🎉 Brighten the year’s saddest day

    Sissy Loses Bet Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Lost Bet
    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
    Submissive Sissy
    Sissy Femdom
    Sissy Boy
    Sissy Slut
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • 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
    • Brand New Asian Femboy Lauren Carter Loses Bet & Dresses up
      07:08
      Brand New Asian Femboy Lauren Carter Loses Bet & Dresses up
      Andre Stone
      2K views
    • Another straight boy turned by Elizabeth Stewart
      04:05
      Another straight boy turned by Elizabeth Stewart
      Elizabeth Stewart
      3.1M 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'll fill your asshole with cum to overflowing
      06:01
      I'll fill your asshole with cum to overflowing
      MrNastyXavier
      1.9M views
    • Sexy Bella loses a bet...and her clothes...
      05:33
      Sexy Bella loses a bet...and her clothes...
      8.1K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • WOMAN DOING A PRIVATE DANCE IN OXXO FOR LOSING BET
      08:08
      WOMAN DOING A PRIVATE DANCE IN OXXO FOR LOSING BET
      NATALIASTARXXX
      4.5K 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 LOSES IT WHILE EDGING ON A MAGIC WAND PLUGGED AND CAGE
      07:47
      SISSY LOSES IT WHILE EDGING ON A MAGIC WAND PLUGGED AND CAGE
      11.3K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.2M views
    • Little young sissy loses her anal virginity with a big dildo and gets a creampie. Sexy fat girly ass tranny.
      07:28
      Little young sissy loses her anal virginity with a big dildo and gets a creampie. Sexy fat girly ass tranny.
      fermerino
      8.1K views
    • 3 anal orgasm and hot creampie for skinny trans whore
      16:52
      3 anal orgasm and hot creampie for skinny trans whore
      ActorFab
      1.9M 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
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      798.4K views
    • The Lost Bet
      01:28
      The Lost Bet
      Sissy Shelby Kiss
      8.4K 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
    • The Bet
      05:04
      The Bet
      Athena Apollonia
      4.8K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M 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
    • Lovely young girl is a shemale with big cock
      08:11
      Lovely young girl is a shemale with big cock
      10.6M views
    • Relevant Short videos

      Warming myself up for all my horny friends, Going live in my nostalgic favorites! Any bets they  have me play with My "
      Warming myself up for all my horny friends, Going live in my nostalgic favorites! Any bets they have me play with My "
      JolieAnn
      6.2K views
      The Bet
      The Bet
      Athena Apollonia
      1.3K views
      I bet you’re already imagining what comes next
      I bet you’re already imagining what comes next
      IskraElectrical49
      567 views
      I bet you would love coming to the office if I showed up
      I bet you would love coming to the office if I showed up
      JessicaXD
      161 views
      Am I making you touch yourself? I bet you are horny af watching me tease in my black lace dress, fully fashioned stockings
      Am I making you touch yourself? I bet you are horny af watching me tease in my black lace dress, fully fashioned stockings
      JessicaXD
      140 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
      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
      171 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
      654 views
    • My wife told me to play this
      11:13
      My wife told me to play this
      965.6K 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
    • Shemale Anatomy
      03:06
      Shemale Anatomy
      2.8M 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
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      476.2K views
    • Bet you don't watch
      08:55
      Bet you don't watch
      Tulip jeans
      2K 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
    • Missy123sassy sissy femboy lost bet cheerleading
      00:42
      Missy123sassy sissy femboy lost bet cheerleading
      Missy123
      4K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      938.3K views
    • Cd slave bet
      01:43
      Cd slave bet
      Mika
      1.4K 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
    • Asuka Bends Over Teasing Daddy Until He Loses Control and Dives in
      03:40
      Asuka Bends Over Teasing Daddy Until He Loses Control and Dives in
      SA247365
      57.9K 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
    • Valeria Loses the Game and Has to Let Herself Be Fucked Hard and Deep.
      13:29
      Valeria Loses the Game and Has to Let Herself Be Fucked Hard and Deep.
      Valera Toro
      396.8K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      696.3K views
    • Sissy College Twink Alexis Loses her Virginity
      01:29
      Sissy College Twink Alexis Loses her Virginity
      477.8K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      293.3K views
    • Lose Control
      06:52
      Lose Control
      156K views
    • A Prostitute Offering Herself on the Street
      02:29
      A Prostitute Offering Herself on the Street
      Wesley Fudedor
      341.2K views
    • Sissy Hollyanne has anal orgasms and loses control
      04:15
      Sissy Hollyanne has anal orgasms and loses control
      Sissy Hollyanne
      70.7K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.4M views
    • Rose the sissy gets punished for losing her butt plug
      02:22
      Rose the sissy gets punished for losing her butt plug
      Rose Jenny
      29.5K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      371.3K views
    • Anal Pleasure With Thick Dildo Stretching Lose & Cumming On Asshole
      12:45
      Anal Pleasure With Thick Dildo Stretching Lose & Cumming On Asshole
      Soloregin
      4.3K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      510.2K 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 Sissy Loses Bet

    • Fuck My Ass Please Dirty Talk
    • Straight Friend Loses Bet
    • Sissy Femboy Fucked From Behind
    • White Femboys Are so Submissive
    • Sissy_tammy
    • Secret Sissyboy
    • Turning Him Into a Complete Bitch
    • Dick Too Big
    • Most Feminine Girl Ever
    • Real First Time
    • No Mercy
    • Wife Encourages Husband Bi Sex
    • Sissy-Slut-Jenny
    • Ruined
    • Out of Control
    • He Can't Take It
    • When She Bigger Than You
    • Sisy Boy
    • Lossing Virginity
    • Uncensored
    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