PornPorn Transgender • US
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • 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
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Anal Challenge Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Anal
    Challenge
    Femboy Anal
    Anal Orgasm
    Sissy Anal
    Crossdresser Anal
    Anal Creampies
    Shemale Anal
    Trans Anal
    Double Anal
    Anal Masturbation
    Bbc Anal
    Painful Anal
    Anal Training
    Ladyboy Anal
    Teen Anal
    Anal Dildo
    Anal Cum
    Anal Fisting
    Anal Gape
    Best Videos
    By clicking the content you will also see an ad. AD
    Transsexual anal challenge in Brazil  -  Episode #09
    08:12
    Transsexual anal challenge in Brazil - Episode #09
    She-Male X
    163.4K views
    Transsexual anal challenge in Brazil  -  Episode #13
    09:04
    Transsexual anal challenge in Brazil - Episode #13
    She-Male X
    92.3K views
    Transsexual anal challenge in Brazil  -  Episode #12
    08:12
    Transsexual anal challenge in Brazil - Episode #12
    She-Male X
    123.4K views
    Transsexual Anal Challenge in Brazil - Episode #05
    08:12
    Transsexual Anal Challenge in Brazil - Episode #05
    She-Male X
    34.3K views
    Transsexual anal challenge in Brazil  -  Episode #11
    08:12
    Transsexual anal challenge in Brazil - Episode #11
    She-Male X
    15.5K views
    Transexual anal challenge - Episode #10
    08:12
    Transexual anal challenge - Episode #10
    She-Male X
    8.9K views
    Transsexual anal challenge in Brazil  -  Episode #08
    08:12
    Transsexual anal challenge in Brazil - Episode #08
    She-Male X
    4.9K views
    Transsexual anal challenge in Brazil  -  Episode #20
    08:12
    Transsexual anal challenge in Brazil - Episode #20
    She-Male X
    10.7K views
    Transexual anal challenge - Episode #01
    08:12
    Transexual anal challenge - Episode #01
    She-Male X
    6.7K views
    Transsexual anal challenge in Brazil  -  Episode #18
    08:12
    Transsexual anal challenge in Brazil - Episode #18
    She-Male X
    6.2K views
    Transsexual anal challenge in Brazil  -  Episode #17
    08:12
    Transsexual anal challenge in Brazil - Episode #17
    She-Male X
    14.6K views
    Transsexual anal challenge in Brazil  -  Episode #16
    08:12
    Transsexual anal challenge in Brazil - Episode #16
    She-Male X
    2.9K views
    Transsexual anal challenge in Brazil  -  Episode #07
    08:12
    Transsexual anal challenge in Brazil - Episode #07
    She-Male X
    2.3K views
    Transexual anal challenge in Brazil  -  Episode #19
    08:12
    Transexual anal challenge in Brazil - Episode #19
    She-Male X
    3.9K views
    Strapon Anal Challenge
    05:54
    Strapon Anal Challenge
    She-Male X
    8.6K views
    Transsexual anal challenge in Brazil  -  Episode #06
    08:19
    Transsexual anal challenge in Brazil - Episode #06
    She-Male X
    2.4K views
    Transsexual sexy anal challenge in Brazil  -  Episode #01
    08:12
    Transsexual sexy anal challenge in Brazil - Episode #01
    She-Male X
    3.4K views
    Transsexual anal challenge in Brazil  - Episode #02
    08:12
    Transsexual anal challenge in Brazil - Episode #02
    She-Male X
    1.8K views
    Transsexual anal challenge in Brazil  -  Episode #04
    08:12
    Transsexual anal challenge in Brazil - Episode #04
    She-Male X
    2K views
    Transexual anal challenge - Episode #03
    08:12
    Transexual anal challenge - Episode #03
    She-Male X
    842 views

    Relevant Short videos

    Transsexual Anal Challenge in Brazil - Episode #05
    Transsexual Anal Challenge in Brazil - Episode #05
    She-Male X
    1.5K views
    Spectacular moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Spectacular moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Ylvis88
    382 views
    Iconic moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Iconic moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Ylvis88
    378 views
    Memorable moment from "Crossdresser in chastity and his daily dildo challenge"
    Memorable moment from "Crossdresser in chastity and his daily dildo challenge"
    Jotti99
    349 views
    Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion
    Secretdreamsfuta Intense Ride: Curvy Beauty Takes on Massive Challenge with Passion
    Hatanoxxxmiwa
    397 views
    Powerful moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Powerful moment from "The 30 minutes challenge for myself - Riding the 12 inch King Cock"
    Ylvis88
    421 views
    Transsexual anal challenge in Brazil  -  Episode #03
    08:12
    Transsexual anal challenge in Brazil - Episode #03
    She-Male X
    7.5K views
    Transexual anal challenge - Episode #05
    08:12
    Transexual anal challenge - Episode #05
    She-Male X
    2.2K views
    Transexual anal challenge - Episode #04
    08:12
    Transexual anal challenge - Episode #04
    She-Male X
    1.5K views
    Transexual anal challenge - Episode #07
    08:12
    Transexual anal challenge - Episode #07
    She-Male X
    1K views
    Transexual anal challenge - Episode #09
    08:12
    Transexual anal challenge - Episode #09
    She-Male X
    943 views
    Transexual anal challenge - Episode #08
    08:12
    Transexual anal challenge - Episode #08
    She-Male X
    2.4K views
    Transexual anal challenge - Episode #06
    08:12
    Transexual anal challenge - Episode #06
    She-Male X
    1.6K views
    Transsexual anal challenge in Brazil  -  Episode #14
    08:12
    Transsexual anal challenge in Brazil - Episode #14
    She-Male X
    1.2K views
    Transsexual anal challenge in Brazil  -  Episode #15
    08:12
    Transsexual anal challenge in Brazil - Episode #15
    She-Male X
    1.2K views
    Transsexual anal challenge in brazil  -  Episode #10
    05:07
    Transsexual anal challenge in brazil - Episode #10
    She-Male X
    1.5K views
    Here we goes the CHALLENGE FIGHT, on ring Sabrina VS Ariadny
    43:16
    Here we goes the CHALLENGE FIGHT, on ring Sabrina VS Ariadny
    zenzetosrl
    286.5K views
    CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)
    45:06
    CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)
    zenzetosrl
    1.8M views
    DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 2
    29:36
    DEVILS FILM - Superstar Trans CHANEL SANTINI has been challenged To A Naughty Gangbang PART 2
    DevilsFilmOfficial
    112.5K views
    TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20
    42:06
    TGilrs CHALLENGE (round 50) - Luna Marks 22 cm VS Kiara 20
    zenzetosrl
    436.3K views
    Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella
    43:58
    Here we goes the CHALLENGE FIGHT 216, on ring Lanny VS Marcella
    Pinko CLUB
    616.3K views
    KAROL 24 cm VS LORENA 20 cm - (TGIRLS CHALLENGE 160)
    37:52
    KAROL 24 cm VS LORENA 20 cm - (TGIRLS CHALLENGE 160)
    zenzetosrl
    429.4K views
    TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela
    40:56
    TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela
    zenzetosrl
    528.7K views
    Rosy VS Nathalia (Tgirls Extreme Challenge)
    46:49
    Rosy VS Nathalia (Tgirls Extreme Challenge)
    zenzetosrl
    156.6K views
    TGilrs CHALLENGE (round 23) - Marla 25 cm VS Daniela 20 cm
    42:59
    TGilrs CHALLENGE (round 23) - Marla 25 cm VS Daniela 20 cm
    zenzetosrl
    775.6K views
    Sissy dogging challenge
    05:59
    Sissy dogging challenge
    293.3K views
    TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly
    44:00
    TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly
    zenzetosrl
    334.8K views
    try not to cum CHALLENGE
    17:22
    try not to cum CHALLENGE
    274.4K views
    TGilrs CHALLENGE (round 21) - Valesca Sargentely 22 cm VS
    40:51
    TGilrs CHALLENGE (round 21) - Valesca Sargentely 22 cm VS
    zenzetosrl
    241.5K views
    Geovane VS Renata (Tgirls Extreme Challenge)
    44:20
    Geovane VS Renata (Tgirls Extreme Challenge)
    zenzetosrl
    277.1K views
    Gloria VS Melissa (Tgirls Extreme Challenge)
    40:01
    Gloria VS Melissa (Tgirls Extreme Challenge)
    zenzetosrl
    362.7K views
    TGilrs CHALLENGE (round 24) - Valesca Sargentely 25 cm VS
    40:32
    TGilrs CHALLENGE (round 24) - Valesca Sargentely 25 cm VS
    zenzetosrl
    1.1M views
    BISEXUAL CUM CHALLENGE
    09:00
    BISEXUAL CUM CHALLENGE
    1.2M views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Anal Challenge

    • Three Minutes of Anal Hell
    • Mature Woman Anal
    • Trans Orgy XXX
    • Sissy Ass to Mouth
    • Anally Destroyed by a Big Dick Shemale
    • Dirty Asshole Licking
    • Bi Crossdresser With Strangers in Park
    • Traps Femboys and Sissys
    • 2 Sissies 1 Chastity Cage
    • Mature Blonde Anal
    • Feminized Husband Turned Into Slave
    • Sissy Maid Humiliation
    • Cum Inside Ass
    • Young Anal
    • Teen
    • Post Op Ladyboy Pussy Creampie
    • Public
    • Teacher Fucked School Bathroom
    • Brutal Gangbang
    • 3 Shemales Fucking Each Other

    xHamster

    • Press
    • 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

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile 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