Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
HALLOWEEN SALE – 50% OFF! 👻🎃 Limited Time, Big Thrills!

Challenge Porn Videos

539 Results

Free Videos
Short Videos
Challenge
Premium Videos
Photos
Shemale Challenge
Edging Challenge
Cum Challenge
Sissy Challenge
Tgilrs Challenge
Stare Challenge
Jerk off Challenge
Cock Hero Challenge
Try Not to Cum Challenge
Straight Stare Challenge JOI Game
Shemale Cum Challenge
Shemales Tube 8
Day 7
Surprise She Has Cock
Shemale Trick
Music Video
Tranny 20
Addicted to Shemales
Hung TS Compilation
Super Hard Cock
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Victoria Justice - Shemale JOI
    06:07
    Victoria Justice - Shemale JOI
    194.7K views
  • She Noticed Me Touching Myself and Didn’t Stop Me
    04:22
    She Noticed Me Touching Myself and Didn’t Stop Me
    Kris Rose
    242.7K views
  • Sissy dogging challenge
    05:59
    Sissy dogging challenge
    348.6K views
  • My Voice and Moans, I Cum in Slow Motion
    32:36
    My Voice and Moans, I Cum in Slow Motion
    Itelia
    68.1K 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
    327.7K views
  • BISEXUAL CUM CHALLENGE
    09:00
    BISEXUAL CUM CHALLENGE
    1.2M views
  • Best of r slash babecock - Bi confusion and bisexual beats
    02:58
    Best of r slash babecock - Bi confusion and bisexual beats
    1.9M views
  • try not to cum CHALLENGE
    17:22
    try not to cum CHALLENGE
    358.7K views
  • Sissy Joyce Challenge
    01:21
    Sissy Joyce Challenge
    Sissy Joyce
    156.4K views
  • Shemale Cock Worship - Part 2
    06:12
    Shemale Cock Worship - Part 2
    352.4K views
  • RIDE IT BETTER THAN YOUR GF!!TRY NOT TO CUM CHALLENGE (COMP)
    03:20
    RIDE IT BETTER THAN YOUR GF!!TRY NOT TO CUM CHALLENGE (COMP)
    214.7K views
  • TGilrs CHALLENGE (round 24) - Valesca Sargentely 25 cm VS
    40:32
    TGilrs CHALLENGE (round 24) - Valesca Sargentely 25 cm VS
    zenzetosrl
    1.3M views
  • Watch it,accept it.
    10:14
    Watch it,accept it.
    311K views
  • Hot Korra Del Rio Challenges Her Hot Asshole with a Bat
    27:37
    Hot Korra Del Rio Challenges Her Hot Asshole with a Bat
    Shemale Strokers
    68.6K 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
    977.2K views
  • Surprise, I have a penis!
    02:49
    Surprise, I have a penis!
    276.9K views
  • Straight Stare challenge - JOI game
    04:57
    Straight Stare challenge - JOI game
    1.1M views
  • Help your friend
    00:39
    Help your friend
    417.8K views
  • coco transe - crossdressers challenge VF 20171229
    24:14
    coco transe - crossdressers challenge VF 20171229
    385.6K views
  • DEVILS TGIRLS - Perfect Trans Babe Khloe Kay Fucks With Another Married Man
    12:19
    DEVILS TGIRLS - Perfect Trans Babe Khloe Kay Fucks With Another Married Man
    Devils tgirls
    146K 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
    648.4K views
  • Relevant Short videos

    Mitsuha's first leak challenge
    Mitsuha's first leak challenge
    Miyamizu Mitsuha
    8.6K views
    She Noticed Me Touching Myself and Didn’t Stop Me
    She Noticed Me Touching Myself and Didn’t Stop Me
    Kris Rose
    6K views
    ABT250116 20cm Dildo Challenge | Clip 1
    ABT250116 20cm Dildo Challenge | Clip 1
    Abby Kitty
    4.8K views
    You Can Tame the Monster, Do You Accept the Challenge?
    You Can Tame the Monster, Do You Accept the Challenge?
    Blacksharon
    1.7K views
    Hot Korra Del Rio Challenges Her Hot Asshole with a Bat
    Hot Korra Del Rio Challenges Her Hot Asshole with a Bat
    Shemale Strokers
    3.3K views
    The 30 minutes challenge for myself - Riding the 12 inch King Cock | Clip 3
    The 30 minutes challenge for myself - Riding the 12 inch King Cock | Clip 3
    Ylvis88
    3.7K views
  • Sorority Trans Girl Gets Pounding Of Her Life - GenderX
    17:07
    Sorority Trans Girl Gets Pounding Of Her Life - GenderX
    GenderX
    544K views
  • TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela
    40:56
    TGilrs CHALLENGE (round 25) - Luna Marksi 22 cm VS Marcela
    zenzetosrl
    810.4K views
  • Why Straight guys love Tranny Porn ??
    05:00
    Why Straight guys love Tranny Porn ??
    619.2K views
  • TGilrs CHALLENGE (round 21) - Valesca Sargentely 22 cm VS
    40:51
    TGilrs CHALLENGE (round 21) - Valesca Sargentely 22 cm VS
    zenzetosrl
    391.6K views
  • Hot trans fuck
    00:55
    Hot trans fuck
    139.1K 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
    478.2K views
  • Made for sucking
    01:10
    Made for sucking
    567K views
  • TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly
    44:00
    TGilrs CHALLENGE (round 06) - Erika Lavigne 23 cm VS Nikolly
    zenzetosrl
    449.3K views
  • Sissy Captions Priceless
    01:32
    Sissy Captions Priceless
    125.7K 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
    zenzetosrl
    984.7K views
  • sissy fantasy manturned in toa sissy slut fuck
    05:21
    sissy fantasy manturned in toa sissy slut fuck
    146.8K views
  • CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)
    45:06
    CAMILLA 20 cm VS JOLIE 25 cm - (TGIRLS CHALLENGE 129)
    zenzetosrl
    2.4M views
  • Transclips - Surprise I Have a Cock
    13:01
    Transclips - Surprise I Have a Cock
    192.2K views
  • cocotranse - fap challenge PMV - sexy crossdressers
    24:20
    cocotranse - fap challenge PMV - sexy crossdressers
    120.7K 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
    445.2K views
  • Triple X pt1
    42:30
    Triple X pt1
    1.4M views
  • You love it
    00:37
    You love it
    86.2K views
  • TGilrs CHALLENGE (round 42) - Renata Molina 22 cm VS Keylla
    46:50
    TGilrs CHALLENGE (round 42) - Renata Molina 22 cm VS Keylla
    zenzetosrl
    550.9K views
  • The stuff of dreams 2
    02:34
    The stuff of dreams 2
    134.6K views
  • TGilrs CHALLENGE (round 33) - Raphaella Ferrari 23 cm VS
    47:05
    TGilrs CHALLENGE (round 33) - Raphaella Ferrari 23 cm VS
    zenzetosrl
    490.6K views
  • My Cock Was so Hard That It Came Out of My Underwear
    01:30:15
    My Cock Was so Hard That It Came Out of My Underwear
    Tomas Styl
    92K views
  • Would you still date me even my cock is bigger than yours?
    07:32
    Would you still date me even my cock is bigger than yours?
    192K views
  • Shemale and bi JOI
    10:04
    Shemale and bi JOI
    285.7K views
  • Sissy Crossdress Hunting Str8 Cock Random Texing
    02:33
    Sissy Crossdress Hunting Str8 Cock Random Texing
    97.4K views
  • Cute Redhead Elf Trap Cums Huge Load & Eats Every Drop Ahegao Cumplay
    05:29
    Cute Redhead Elf Trap Cums Huge Load & Eats Every Drop Ahegao Cumplay
    Itelia
    162.8K views
  • cum blaster
    00:38
    cum blaster
    427.8K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 8
  9. ...
  10. 12
12

Porn Related to Challenge

Shemale Challenge
Surprise I Have a Dick
Shemale Confusion
Show Me Your Cock
Straight Challenge
Two Shemales Cum Together
Truth or Dare Game
Shemale's Secret
Suprise I Have a Dick
Wife Surprises Husband
Pride
Hung Compilation
Straight Test
Shemale Tribute
Unusual Dick
Gay Test
Shemale Reveal
Are You Straight
Surprise I Have
Trans Encouragement
Related Channels
  • #147
    Sissy Instruction
    Sissy Instruction
  • #179
    Kimberhaven
    Kimberhaven
  • #259
    Tranny Newbies
    Tranny Newbies
  • #174
    Jolie and Friends
    Jolie and Friends
  • #231
    obeylilith.com
    obeylilith.com
  • #280
    Shemale Tugjobs
    Shemale Tugjobs
  • #338
    iwantclips
    iwantclips
  • #232
    Shemale Sex HD Channel
    Shemale Sex HD Channel
  • View all
Monetize your content
Become a creator
xHamster
  • About us
  • Blog
  • Creator's Blog
  • Advertising
  • xHamster Awards 2025
  • SEO Specialist Job
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
U.S.C. 2257 Notice
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