PornPorn Transgender • US
  • Videos
  • Photos
  • Short videos
  • Users
    • Live Sex
      -50%
    • Premium Premium Videos
      -60%
    • Pornstars
    • Channels
    50% OFF Tokens for NY Ring in 2026 with the right company on xHamsterLive!

    First Anal Cry Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    HD
    Full HD
    4K
    VR
    Best Videos
    By clicking the content you will also see an ad. AD
    • SISSIES , THE BLACK BOOMERANG IS BACK!!!!!
      02:32
      SISSIES , THE BLACK BOOMERANG IS BACK!!!!!
      476.6K views
    • Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
      08:09
      Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
      Kitsy Meow
      167.5K views
    • SOPHIE KRENS BOUND AND CRY
      01:18
      SOPHIE KRENS BOUND AND CRY
      Sophie Krens
      38.3K views
    • Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      14:26
      Extreme Painanal large dildo with chilli sauce pushes Denise to her limits and makes her cry.
      Denise Humain
      41.8K views
    • Horse Cocked Ebony TS Granny Adrieli Pinheiro Makes BF Cry
      08:11
      Horse Cocked Ebony TS Granny Adrieli Pinheiro Makes BF Cry
      Dream Tranny
      318.3K views
    • Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
      13:53
      Newest Scene Compilation (with new Stuff) incl. Anal, Gaping, Nipple Pain, Humiliation, Sissy, BDSM, Trans, Denise Humain
      Denise Humain
      2.3K views
    • anal machine for sissy crying of joy
      01:25
      anal machine for sissy crying of joy
      Luciejoconde
      10.6K views
    • whore orgasm machine anal
      02:00
      whore orgasm machine anal
      Luciejoconde
      15.3K views
    • Piston Machine Reams Hot and Horny Tgirl Crystal Delicia
      12:05
      Piston Machine Reams Hot and Horny Tgirl Crystal Delicia
      Dream Tranny
      3.8K views
    • Hot Tranny Crystal Delicia Cums Hard After Taking Machine Dick
      12:02
      Hot Tranny Crystal Delicia Cums Hard After Taking Machine Dick
      Dream Tranny
      5.1K views
    • Hot and Horny TS Crystal Delicia Runs a Fucking Machine in Her Ass
      12:05
      Hot and Horny TS Crystal Delicia Runs a Fucking Machine in Her Ass
      Dream Tranny
      3.1K views
    • Trans Hottie Crystal Delicia Has Her Ass Plowed by a Fucking Machine
      10:05
      Trans Hottie Crystal Delicia Has Her Ass Plowed by a Fucking Machine
      Dream Tranny
      3.5K views
    • Cum  teaser
      00:30
      Cum teaser
      Sissy Joyce
      76.9K views
    • ts make her slut
      03:49
      ts make her slut
      741K views
    • Don't Cry Tranny !!! Jerking Off at your Job is a NO NO!!
      02:44
      Don't Cry Tranny !!! Jerking Off at your Job is a NO NO!!
      194.2K views
    • Big Girls Don't Cry
      20:50
      Big Girls Don't Cry
      618.1K views
    • AJ180 Attempts to Fill Her Hungry Hole in Will It Fit
      32:19
      AJ180 Attempts to Fill Her Hungry Hole in Will It Fit
      AJ180
      70.6K views
    • HOT CHICKS WITH HUGE DICKS COMPILATIONS
      15:05
      HOT CHICKS WITH HUGE DICKS COMPILATIONS
      Futanari XXX
      154.9K views
    • Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
      14:42
      Dirty Sissy whore closed, brought up and humiliated into dilapidated residential ruins.
      Denise Humain
      29.8K views
    • AJ180 Is Tight As Fuck! Can She Handle a 12-Inch Dildo Ride
      04:45
      AJ180 Is Tight As Fuck! Can She Handle a 12-Inch Dildo Ride
      AJ180
      46.8K views
    • Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      18:54
      Sissy Denise: Tied Nipples Tortured with Rough Round Brushes
      Denise Humain
      1.4K views
    • Sissy Denise: Nipple torture with combination pliers – Live until the end
      09:37
      Sissy Denise: Nipple torture with combination pliers – Live until the end
      Denise Humain
      2.2K views
    • Dorian and Angelique aka Victorian Age Crying Game
      10:35
      Dorian and Angelique aka Victorian Age Crying Game
      94.5K views
    • Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      13:59
      Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.
      Denise Humain
      19.6K views
    • A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      28:23
      A Day in Sissys Life. Daily BDSM Sex Slave Routine with Fuckslut Denise Humain.
      Denise Humain
      11.6K views
    • AJ180 Cuckold Queen: You & Your Wife Are Sluts
      00:30
      AJ180 Cuckold Queen: You & Your Wife Are Sluts
      AJ180
      38.4K views
    • TS Fucks man
      02:10
      TS Fucks man
      207K views
    • Cry For Love - cumshot compilation with sweet memories of severe spanking
      05:14
      Cry For Love - cumshot compilation with sweet memories of severe spanking
      Chantal Fouet
      3.5K views
    • Sexy body on Jamie Croft is so hot it makes you wanna cry
      01:15
      Sexy body on Jamie Croft is so hot it makes you wanna cry
      Trans 500
      68K views
    • This song is so romantic it makes me cry hehe but i hope you like my little mixx
      05:41
      This song is so romantic it makes me cry hehe but i hope you like my little mixx
      Lizzaali
      3.1K views
    • Guy Gets His First Anal Fuck From Big Tit Tranny Labelly After Party
      32:41
      Guy Gets His First Anal Fuck From Big Tit Tranny Labelly After Party
      Shemale TS Collection
      85.4K views
    • First Anal Porn with Sexslave Linciatrans
      08:12
      First Anal Porn with Sexslave Linciatrans
      ActorFab
      208.4K views
    • Indian hot porn star jazz first Anal sex video fucking with musclear boy with huge cock
      17:29
      Indian hot porn star jazz first Anal sex video fucking with musclear boy with huge cock
      harry1
      3.2M views
    • Guy Gets His First Anal Sex From a Latin Shemale in a Hotel
      21:31
      Guy Gets His First Anal Sex From a Latin Shemale in a Hotel
      Shemale TS Collection
      15.4K views
    • Guy Gets His First Anal Fuck with Big Tit Tranny Jade
      23:28
      Guy Gets His First Anal Fuck with Big Tit Tranny Jade
      Shemale TS Collection
      188.9K views
    • Asian Big Tit Tranny Suzie Gets First Anal Fuck in Hotel
      31:21
      Asian Big Tit Tranny Suzie Gets First Anal Fuck in Hotel
      Shemale TS Collection
      44.7K views
    • Thick FUTA stepmother first anal with step sis (AI upscaled gameplay)
      01:22
      Thick FUTA stepmother first anal with step sis (AI upscaled gameplay)
      adobocreamph
      48.2K views
    • Shy cd gets first anal
      14:23
      Shy cd gets first anal
      567.8K views
    • Big Tit Skinny Tranny Gets Her First Anal Fuck From Naughty Neighbors
      20:53
      Big Tit Skinny Tranny Gets Her First Anal Fuck From Naughty Neighbors
      Shemale TS Collection
      9.1K views
    • NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
      10:44
      NEW TEENY TRANNY TS-Emily Adaire FIRST ANAL CREAMPIE
      Andy Star
      199K views
    • First Anal with volume
      01:18
      First Anal with volume
      78.4K views
    • Asian Ladyboy Pitta Gets First Anal Fuck in Tight Asshole
      34:43
      Asian Ladyboy Pitta Gets First Anal Fuck in Tight Asshole
      Shemale TS Collection
      20.1K views
    • my friend first anal
      01:08
      my friend first anal
      25.7K views
    • My first Anal with a Shemale!!! - Episode #02
      26:32
      My first Anal with a Shemale!!! - Episode #02
      Shemale World
      90.4K views
    • Guy Gets His First Anal Fuck From Horny Tranny
      08:12
      Guy Gets His First Anal Fuck From Horny Tranny
      Shemale TS Collection
      4.4K views
    • SO-SENSUELLA, my first anal Fist.
      05:22
      SO-SENSUELLA, my first anal Fist.
      92.6K views
    • Big Tit Asian Skinny Shemale Teen Aye Gets First Anal Fuck
      20:45
      Big Tit Asian Skinny Shemale Teen Aye Gets First Anal Fuck
      Shemale TS Collection
      13.1K views
    Next page
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5
    6. 6
    7. ...
    8. 41
    9. ...
    10. 80
    80

    Categories

    American
    4K Porn
    HD Videos
    VR Porn
    Shemale Fucks Guy
    Big Cock
    Black
    Shemale Fucks Shemale
    Amateur
    Shemale Fucks Girl
    Sissy
    Ladyboy
    Guy Fucks Shemale
    Compilation
    Blowjob
    Cum In Mouth
    Big Black Cock
    Big Ass
    Creampie
    Bareback
    Cumshot
    Homemade
    Mature
    Teen
    Masturbation
    Domination
    Anal
    Brazilian
    Asian
    Solo
    Transgender
    BBW
    Mexican
    Interracial
    Cartoon
    Japanese
    Young
    Big Tits
    Small Cock
    Vintage
    Thai
    Lingerie
    Trans Woman
    Gangbang
    Threesome
    Colombian
    Petite
    Public
    BDSM
    Rough Sex
    Couple
    MILF
    POV
    Dildo
    Stockings
    Cuckold
    Anal Masturbation
    Trans Man
    Small Tits
    Babysitter
    Outdoor
    Indian
    Chinese
    Handjob
    Group Sex
    Fetish
    Bondage
    Massage
    Hentai
    British
    Pissing
    Double Penetration
    FTM
    Role Play
    Behind The Scenes
    German
    Anal Toy
    SFW
    All categories
    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