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
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    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

    Jerk Off Challenge Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Jerking
    Challenge
    Jerking off
    Shemale Jerking off
    Condom off
    Circle Jerk
    Jerk off Instruction
    Caught Jerking off
    Trans Jerking off
    Jerking Together
    Shemale Challenge
    Jerk off Encouragement
    Jerking off Together
    Jerking Cum
    Cum Challenge
    Sucked off
    Solo Jerk off
    Caught Jerking
    Edging Challenge
    Shemale Jerk
    Best Videos
    By clicking the content you will also see an ad. AD
    I had a big cumshot in unkown hotel
    05:39
    I had a big cumshot in unkown hotel
    Samantha Sissy World
    1.5M views
    Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!
    01:13
    Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!
    TV_Helena
    42.6K views
    Hung Sexy Tranny Babe Gets Handjob & Cums
    04:33
    Hung Sexy Tranny Babe Gets Handjob & Cums
    2.8M views
    2022 Christmas Cum Eating Challenge CEI
    16:00
    2022 Christmas Cum Eating Challenge CEI
    April Bee
    21.5K views
    Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
    13:19
    Cum eating instructions hung tgirl eats her own cum to show you how it's done, humiliation feminization JOI
    Holly unt
    67.9K views
    SisK Pantyhose Challenge EP3.2: Jerking off until cum
    07:56
    SisK Pantyhose Challenge EP3.2: Jerking off until cum
    SissyKanisa
    36.1K views
    EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    36:39
    EAT SHEMALE CUM HYPNO CEI TRAINER PART 3
    1.6M views
    You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN
    00:43
    You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN
    TV_Helena
    16.1K views
    Most cute sissy trans cumshot a bigload
    05:24
    Most cute sissy trans cumshot a bigload
    Samantha Sissy World
    708.9K views
    Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH
    01:16
    Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH
    TV_Helena
    59.7K views
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    03:02
    POV - Straight Guy SEDUCED by Hung Blonde BWC Trans Girl - Cadence Caliber
    TS Cadence Caliber
    122.6K views
    Coffee and SheDick Edge November edge challenge
    07:25
    Coffee and SheDick Edge November edge challenge
    MerlinMystique
    1.6K views
    Ts witch JOI - "lets frot and cum"
    06:37
    Ts witch JOI - "lets frot and cum"
    Erica Cherry
    90K views
    THE CHALLENGE WAS TO SEE HOW LONG SHE LASTS
    00:25
    THE CHALLENGE WAS TO SEE HOW LONG SHE LASTS
    97.7K views
    Surprise Compilation
    02:14
    Surprise Compilation
    2.4M views
    Warm and sticky cum inside nylon pantyhose (SisK Vlog Pantyhose Challenge EP2.2)
    09:13
    Warm and sticky cum inside nylon pantyhose (SisK Vlog Pantyhose Challenge EP2.2)
    SissyKanisa
    56.6K views
    Making My Cock Explode
    08:09
    Making My Cock Explode
    TSRyley
    46.7K views
    SisK Pantyhose Challenge EP3.1: Shiny White
    17:14
    SisK Pantyhose Challenge EP3.1: Shiny White
    SissyKanisa
    57.8K views
    Dirty Talking T-girl Cums
    06:05
    Dirty Talking T-girl Cums
    1.2M views
    Self-training 49. M-shaped leg spread challenge on a public beach
    32:35
    Self-training 49. M-shaped leg spread challenge on a public beach
    megu2002
    855 views
    Edging & Cumming with Toys 3
    19:48
    Edging & Cumming with Toys 3
    1.5M views
    Self-training 49: M-leg Split Challenge at a Beach
    08:12
    Self-training 49: M-leg Split Challenge at a Beach
    megu2002
    770 views
    Cumshot compilation 2 - Beautiful tranny, ladyboy big orgasm
    06:52
    Cumshot compilation 2 - Beautiful tranny, ladyboy big orgasm
    2.7M views
    Self-training No. 48: Tackle-ass Exposure Challenge Walk
    11:12
    Self-training No. 48: Tackle-ass Exposure Challenge Walk
    megu2002
    969 views
    Hazel shoots another load
    09:33
    Hazel shoots another load
    1.7M views
    ill Sophies 4 minute Cum Challenge
    04:04
    ill Sophies 4 minute Cum Challenge
    Ill Sophie
    13.7K views
    Shemale worship JOI
    11:45
    Shemale worship JOI
    462.7K views
    Transsexual anal challenge in Brazil  -  Episode #07
    08:12
    Transsexual anal challenge in Brazil - Episode #07
    She-Male X
    2.3K views
    Trans Erica Cherry wants to fuck you rough (dirty talk)
    19:28
    Trans Erica Cherry wants to fuck you rough (dirty talk)
    Erica Cherry
    107.1K views
    Transsexual anal challenge in Brazil  -  Episode #03
    08:12
    Transsexual anal challenge in Brazil - Episode #03
    She-Male X
    7.5K views
    Swallow My Cum
    15:15
    Swallow My Cum
    TSRyley
    240.6K views
    Transsexual anal challenge in Brazil  -  Episode #06
    08:19
    Transsexual anal challenge in Brazil - Episode #06
    She-Male X
    2.4K views
    Ladyboys Shemales Cumming With Help
    07:11
    Ladyboys Shemales Cumming With Help
    3.8M views
    Transsexual sexy anal challenge in Brazil  -  Episode #01
    08:12
    Transsexual sexy anal challenge in Brazil - Episode #01
    She-Male X
    3.3K views
    Straight Boy Test (Shemales, Cock)
    16:59
    Straight Boy Test (Shemales, Cock)
    1.7M views
    Transsexual anal challenge in Brazil  - Episode #02
    08:12
    Transsexual anal challenge in Brazil - Episode #02
    She-Male X
    1.8K views
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    11:53
    POV housemate finds your panties and feminizes you JOI dominant trans girl
    Holly unt
    160.9K views
    Transsexual anal challenge in Brazil  -  Episode #04
    08:12
    Transsexual anal challenge in Brazil - Episode #04
    She-Male X
    2K views
    Cum Pumps Under Pressure #2
    16:42
    Cum Pumps Under Pressure #2
    857.3K views
    Get sucked off by a mexican CD CHALLENGE
    06:09
    Get sucked off by a mexican CD CHALLENGE
    81K views
    One-your-knees Bad Boy!
    08:29
    One-your-knees Bad Boy!
    Reds Trans Stars
    149.9K 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
    281.7K views
    Cumshot Compilation Part 1
    14:15
    Cumshot Compilation Part 1
    10M 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
    girlcock brainwashing - sink even deeper
    17:10
    girlcock brainwashing - sink even deeper
    390.1K 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
    106.5K 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
    364.1K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Jerk Off Challenge

    • Jerk off Encouragement
    • Suprise I Have a Dick
    • Shemale Cock Surprise
    • Cum Challenge
    • Fast Jerking Trans
    • Solo Masturbation Orgasm
    • Sexy Dirty Talk While Masturbating
    • Watch Me Jerk off
    • Cumming in Own Mouth
    • Surprise Cock Reveal
    • Live Cam Masturbate
    • Cum Begging
    • Transgender Taboo Porn
    • When She Bigger Than You
    • Complete Penis Erection Process
    • The Hottest Thing I've Ever Seen
    • Pulsing Cumshot Down Throat
    • Sucking Shecock
    • Helping Hand Huge Explosion
    • Sissy Truth Dare

    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