PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
    • Premium Premium Videos
    • Pornstars
    • Channels

    Cuckholding First Time Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    First
    Time
    First Time
    Young First Time
    Crossdresser First Time
    First Time Shemale
    First Time Virgin
    First Time Anal
    Homemade First Time
    Cd First Time
    First BBC
    First Date
    First Time Trans
    Sissy First Time
    First Time Ladyboy
    Adult Time
    First Trans
    First Time Sucking
    First Blowjob
    Straight First Time
    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
    • Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
      14:12
      Cuckhold gets Fucked by the Wife's Bull Fiona Fortune Sissy CD Cuck
      Fiona Fortune
      108.6K 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
      634.4K views
    • Cuckhold's secrets
      18:11
      Cuckhold's secrets
      157.5K 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
      399.5K views
    • Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      10:25
      Jade Venus Is Meeting Her Mother-In-Law For The First Time And Her Pussy At The Same Time - Trans Angels
      Trans Angels
      9.1M 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
    • First Time Anal
      08:41
      First Time Anal
      Pure Ts
      78.4K views
    • Guy gets fooled into sex with a shemale
      06:15
      Guy gets fooled into sex with a shemale
      Love4TS
      2.6M views
    • Trap takes BWC for the first time from daddy
      00:54
      Trap takes BWC for the first time from daddy
      3M views
    • surprise she has dick
      07:34
      surprise she has dick
      254.3K views
    • My first time with a trans girl !!
      14:58
      My first time with a trans girl !!
      Lina Mila
      2.1M 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
      292.3K views
    • HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
      01:12
      HIS FIRST TIME FUCKED BY A LADYBOY AND HE CUM
      1M views
    • Hostel Surprise
      37:09
      Hostel Surprise
      3.1M views
    • First Time Glory Hole
      09:03
      First Time Glory Hole
      441.6K views
    • Guy loses bet turns into sissy CD giving blowjob
      04:52
      Guy loses bet turns into sissy CD giving blowjob
      1.3M views
    • Blonde gurl's first time.
      04:01
      Blonde gurl's first time.
      1.3M views
    • Fucking of a Lifetime - Variety Itsol
      10:36
      Fucking of a Lifetime - Variety Itsol
      Rodrigo Amor
      3.4M views
    • First time with a tranny (shemale) and we enjoy tasty cock
      07:11
      First time with a tranny (shemale) and we enjoy tasty cock
      2.8M views
    • Ultimate cuckold tranny humiliation!
      05:36
      Ultimate cuckold tranny humiliation!
      Femdom Austria TS
      69.3K views
    • Relevant Short videos

      First time going out like a sissy slut !
      First time going out like a sissy slut !
      MommyThongs
      65.4K views
      Rian uploads for the first time
      Rian uploads for the first time
      18.5K views
      Virgin wanted to have unforgettable first time with both of us
      Virgin wanted to have unforgettable first time with both of us
      AcrylicCloud
      6.2K views
      First Time Straight Guy Blowjob With Trans girl in a Hotel
      First Time Straight Guy Blowjob With Trans girl in a Hotel
      7.5K views
      First time with new toy x
      First time with new toy x
      Sophie1087
      3.2K views
      Pissing in my roommates sink for the first time
      Pissing in my roommates sink for the first time
      BunBunBoi
      3.5K views
    • MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
      20:51
      MY STEPBROTHER WANTS TO TRY FOR THE FIRST TIME WITH A TRANS GIRL
      yesid
      1.1M views
    • I turned my straight roommate into my wife
      06:06
      I turned my straight roommate into my wife
      CutePinkUnicorn
      2.1M views
    • FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
      03:12
      FEMOUT - Cutie Pixie Pond First Time To Show Her Goodies
      Femout
      18.8K views
    • family fun 1.mp4
      13:05
      family fun 1.mp4
      1.8M views
    • My first time with a real transsexual...
      08:12
      My first time with a real transsexual...
      She-Male X
      665.5K views
    • Surprise! She has a cock!
      00:49
      Surprise! She has a cock!
      301.5K views
    • FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
      03:11
      FEMOUT XXX - First Time Black Teen petite Tgirl masturbates
      Femout
      655.1K views
    • Tricking my neighbor and fucking his ass
      03:49
      Tricking my neighbor and fucking his ass
      Elizabeth Stewart
      594.6K views
    • TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
      10:25
      TRANS ANGELS - Izzy Wilde Meets Her Stepbro Sage Roux For The First Time And In No Time Gets His Cock Out To Suck - TRANS ANGELS
      Trans Angels
      747.7K views
    • My stepmom is a tranny
      16:46
      My stepmom is a tranny
      Combat zone transsexual barebacking
      1.1M views
    • first time taking BWC in ass and i like it. Part 2
      00:39
      first time taking BWC in ass and i like it. Part 2
      1M 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
      215.1K views
    • M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
      01:29:57
      M584G02 My son who has returned for the first time in a few years is a transcendental transsexual.
      M MBM3988
      912K views
    • Wife Catches Husband With TS Girl, Makes Him Sucks Her Dick
      12:52
      Wife Catches Husband With TS Girl, Makes Him Sucks Her Dick
      GenderX
      1.3M views
    • Beograd first time with transgirl
      01:59
      Beograd first time with transgirl
      395.3K views
    • Another straight guy getting tricked by this hot tgirl
      26:17
      Another straight guy getting tricked by this hot tgirl
      1.1M views
    • Your Very First Time - Trans Femdom GFE with Melissa Masters
      03:40
      Your Very First Time - Trans Femdom GFE with Melissa Masters
      Melissa Masters
      366K views
    • You will never forget your first time with shemale babe Mel
      12:07
      You will never forget your first time with shemale babe Mel
      Tranny Newbies
      1M views
    • Young guy fucked in the ass for the first time by a tranny
      17:25
      Young guy fucked in the ass for the first time by a tranny
      1M 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
    • My First Time With a BBC
      08:45
      My First Time With a BBC
      384K views
    • Facefucking My Boy Til I Flood His Throat in My Girlcum
      05:48
      Facefucking My Boy Til I Flood His Throat in My Girlcum
      Elizabeth Stewart
      413.9K views
    • First time with my TS stepsister
      01:37
      First time with my TS stepsister
      David Rey
      556.7K 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
    • FEMOUT - Introducing The Valentine Fox First Time Lust
      03:12
      FEMOUT - Introducing The Valentine Fox First Time Lust
      Femout
      14.8K views
    • How I've made my boyfriend into a anal slut
      04:39
      How I've made my boyfriend into a anal slut
      Trinit Noir
      60.1K 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 Cuckholding First Time

    • Wife Taking Black Cock
    • Swallowing Strangers Cum
    • Sucking Very First BBC
    • Cumming in Guys Mouth
    • Surprise I Have a Dick
    • Shemale Surprises Guy
    • Cuckold Humiliation
    • Cuming While Being Fucked
    • My Wife's Boyfriend Fuck My Ass
    • Turning Cuck Husband Into Faggot
    • He Can't Take It
    • Blowjob With Swallowed
    • Reverse Cowgirl
    • Breeding Bitch
    • Maybe the Best Cocksucker
    • Asian Femboy Poked Cums Handsfree
    • Crossdresser Caught Fucking Dildo
    • Prostate Orgasm No Hands
    • Oral Domination
    • Extreme Dirty Talking
    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