PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels
    WINTER MAGIC SALE ❄️☃️ Snowy discounts, hot deals!

    Sissy Boyfriend Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Boyfriend
    My Sissy Boyfriend
    Sissy Boyfriend Strapon
    Sissy Boyfriend Training
    Sissy Crossdresser and Boyfriend
    Passionate Sissy Fucked Boyfriend
    Asian Sissy and Boyfriend
    Fucking a Sissy Cheating Boyfriend
    From Boyfriend to Sissy Boyfriend
    Woman Turns Boyfriend Into Sissy Slave
    Femdom Anal Training for Sissy Boyfriend
    Sissy and Her Boyfriend Enjoying Sex
    Maddie Wright Boyfriend Sissy Slut Sara
    Sissy Crossdresser
    Sissy Training
    Bbc Sissy
    Sissy Feminization
    Young Sissy
    Sissy Husband
    HD
    Full HD
    4K
    VR
    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
      3M views
    • My Sissy Boyfriend 07
      18:22
      My Sissy Boyfriend 07
      406.3K views
    • shemale dresses sissy to fuck
      16:14
      shemale dresses sissy to fuck
      2.1M views
    • My Sissy Boyfriend 23
      19:43
      My Sissy Boyfriend 23
      203.4K views
    • Dads Bestmate Bangs Femboy
      05:11
      Dads Bestmate Bangs Femboy
      mothplayboy
      788.3K views
    • Lara Page sissy boyfriend
      15:47
      Lara Page sissy boyfriend
      93.6K views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M views
    • Tgirl dominates her sissy boyfriend
      06:01
      Tgirl dominates her sissy boyfriend
      Transsensual
      102.1K views
    • I turned my straight roommate intro trans wife
      05:20
      I turned my straight roommate intro trans wife
      CutePinkUnicorn
      506.6K views
    • My Sissy Boyfriend 22
      17:37
      My Sissy Boyfriend 22
      46.1K views
    • dominant stepmom helps out her sissy slave
      05:59
      dominant stepmom helps out her sissy slave
      Pure Ts
      369.2K views
    • Sissy Boyfriend Sex Denial
      03:45
      Sissy Boyfriend Sex Denial
      Brat Perversions
      2.5K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Ebony shemale  fuck sissy boyfriend
      22:33
      Ebony shemale fuck sissy boyfriend
      215.9K views
    • Never Expecting to Be a Sexy Girl
      08:12
      Never Expecting to Be a Sexy Girl
      Pure Ts
      473K views
    • Girlfriend Sissy Boyfriend to Go on Date With Man
      00:21
      Girlfriend Sissy Boyfriend to Go on Date With Man
      Bailey Wilde
      21.5K views
    • Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      08:16
      Taking a straight guy home to turn him into my faggot - Elizabeth Stewart
      Elizabeth Stewart
      402K views
    • Cute young blonde tranny with nice dick loves to assfuck her sissy boyfriend
      19:36
      Cute young blonde tranny with nice dick loves to assfuck her sissy boyfriend
      61.5K 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
    • Sucking some dudes cock while my boyfriend is at work
      05:18
      Sucking some dudes cock while my boyfriend is at work
      JsseMontz
      565.1K views
    • Sissy Femboy Fucked From Behind
      05:20
      Sissy Femboy Fucked From Behind
      2.7M views
    • My boyfriend came to see me and fuck my ass well
      09:53
      My boyfriend came to see me and fuck my ass well
      Piou_Sissy
      29.2K 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
      636.6K views
    • Anal Bareback Straight Boyfriend Pounded By My Huge Brazilian Cock In Paris Montmartre
      07:41
      Anal Bareback Straight Boyfriend Pounded By My Huge Brazilian Cock In Paris Montmartre
      DotadaSP
      533K views
    • Loser Boyfriend Gets Feminized and Fucked
      08:12
      Loser Boyfriend Gets Feminized and Fucked
      Pure Ts
      291.2K views
    • Ladyboy Horny Want Boyfriend Fucking Her Bareback Cumshot Part 2
      19:42
      Ladyboy Horny Want Boyfriend Fucking Her Bareback Cumshot Part 2
      Poynew Oyy
      50.3K views
    • A guide to sissication: Beginner - Am I a sissy?
      23:32
      A guide to sissication: Beginner - Am I a sissy?
      748.2K views
    • BBC Boyfriend Put His Big Python in My Sissy Ass - Part2
      09:24
      BBC Boyfriend Put His Big Python in My Sissy Ass - Part2
      Rozebella
      15.9K views
    • Sissy CD sucks and is fucked
      08:25
      Sissy CD sucks and is fucked
      1.4M views
    • Sissy Enjoy her BBC Boyfriend
      11:44
      Sissy Enjoy her BBC Boyfriend
      370.7K views
    • Sissy cum dump compilation
      28:49
      Sissy cum dump compilation
      2.6M views
    • TS Ria Bentley Has Hardcore Morning Sex With Boyfriend Brandon Lee Harrington
      07:07
      TS Ria Bentley Has Hardcore Morning Sex With Boyfriend Brandon Lee Harrington
      Ria_Bentley
      227.9K views
    • Daddy's Good Girl!
      08:12
      Daddy's Good Girl!
      Pure Ts
      932.5K views
    • the DREAM of the girl next door, a sporty trans girl after training puts her boyfriend to suck in the kitchen
      01:24
      the DREAM of the girl next door, a sporty trans girl after training puts her boyfriend to suck in the kitchen
      GiGiMoon81
      160.9K views
    • Male to female gender transformation smoking whore
      16:00
      Male to female gender transformation smoking whore
      693.8K views
    • Amazing facial cumshot on my slut of a boyfriend after an epic mutual ass-licking
      06:55
      Amazing facial cumshot on my slut of a boyfriend after an epic mutual ass-licking
      DotadaSP
      734.6K views
    • Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
      08:12
      Sexy Trans Girl Tricks Straight Boy and Fucks His Holes
      Elizabeth Stewart
      295.6K views
    • cd sissy having fun with her boyfriend
      07:56
      cd sissy having fun with her boyfriend
      762.8K views
    • Rented Out by His Mistress
      06:12
      Rented Out by His Mistress
      Pure Ts
      61.9K views
    • I LOVE THROATING DUDES WITH GIRLFRIENDS LOL
      02:57
      I LOVE THROATING DUDES WITH GIRLFRIENDS LOL
      JsseMontz
      118.3K views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • My Boyfriend Wants It in the Ass
      14:09
      My Boyfriend Wants It in the Ass
      T ThedarksideX
      11.6K 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
    • bbc Boyfriend Love fuck my hot ass part2 _Rozebell
      10:15
      bbc Boyfriend Love fuck my hot ass part2 _Rozebell
      Rozebella
      176.3K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • I fucked hard my boyfriends ass
      05:45
      I fucked hard my boyfriends ass
      Trinit Noir
      175.5K views
    • How to Train Your Sissy Boyfriend
      08:12
      How to Train Your Sissy Boyfriend
      Brat Perversions
      110.6K 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 Boyfriend

    • Teen Sissy Boy
    • Femboy Fucked
    • Crossdresser First Time With a Man
    • Secret Sissyboy
    • Shemale Twink
    • Turning Cuck Husband Into Faggot
    • Cute Traps for Straight Guys
    • Femboygirlfriend
    • Girlfriend Catches Me Crossdressing
    • Feminine Boys
    • Brutal Tranny
    • Crossdress Gangbang
    • Crossdressers Hardcore
    • Sissy-Virgin
    • Trans Step Sis XXX
    • Two Femboys
    • Bisexual Domination
    • Breeding Boyfriend
    • Tricking My Neighbor and Fucking His Ass
    • Trap Fuck Tumblr
    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