Challenge Videos - Gay (11,707)

These Three In Trouble

These Three In Trouble

Clips4sale 1 year ago

Tied Myself up to Do This Hands-free Cum Challenge

Tied Myself up to Do This Hands-free Cum Challenge

FapHouse 1 year ago

Before & After sex workputs

Before & After sex workputs

XHamster 1 year ago

”Sebastian Keys dominates Brian Bonds in dirty torment challenge”

”Sebastian Keys dominates Brian Bonds in dirty torment challenge”

Faptor 1 year ago

2stage Pumping Size Tube 5x6x12inches

2stage Pumping Size Tube 5x6x12inches

XHamster 1 year ago

BareBrazil.com - Fabio & Yuri - Fabio beats Yuri in arm wrestling and dares him to suck him

BareBrazil.com - Fabio & Yuri - Fabio beats Yuri in arm wrestling and dares him to suck him

Yeswegays 1 year ago

Its challenging to breathe when Im getting choked by DILF Sir Peters gigantic cock

Its challenging to breathe when Im getting choked by DILF Sir Peters gigantic cock

GayCK 1 year ago

challenge to get all my milk

challenge to get all my milk

Flirt4Free 2 years ago

Aaron Challenged Himself to a Physical Orgasm Today

65% HD 0:08 / 0:39

Aaron Challenged Himself to a Physical Orgasm Today

FapHouse 1 year ago

From straight to gay reprogramming 7! Stranger Feet Worship!

57% 0:30 / 15:44

From straight to gay reprogramming 7! Stranger Feet Worship!

Clips4sale 1 year ago

”Beating the Heat”

”Beating the Heat”

Trashreality 1 year ago

10 Gay Questions - Interactive Quiz

HD 0:10 / 18:18

10 Gay Questions - Interactive Quiz

LoyalFans 1 year ago

Cameron Kincade's Excruciating Ass Challenge

Cameron Kincade's Excruciating Ass Challenge

OurGay 2 years ago

Bottom Drew Dixon Raw Fucked By Romeo Davis

Bottom Drew Dixon Raw Fucked By Romeo Davis

GayXPS 1 year ago

Raw: The Last Video: A New Challenge

Raw: The Last Video: A New Challenge

GayTubesTV 1 year ago

Guy Criss is all ready to fill his mouths with three enormous penises

Guy Criss is all ready to fill his mouths with three enormous penises

Yeswegays 1 year ago

Atonement

Zatube 1 year ago

”Fight Fire With Fire”

”Fight Fire With Fire”

Trashreality 1 year ago

Aaron Challenged Himself to a Physical Orgasm Today.ep 4-5

66% HD 1:01 / 16:07

Aaron Challenged Himself to a Physical Orgasm Today.ep 4-5

FapHouse 1 year ago

”Jake Preston Takes Down Reigning Champ Sam Ledger”

”Jake Preston Takes Down Reigning Champ Sam Ledger”

Trashreality 1 year ago

”Talking about the gay porn shooting with Diego Sans & Luis Rubi”

”Talking about the gay porn shooting with Diego Sans & Luis Rubi”

Zatube 1 year ago

”BottomGames - Muscle Hunk Challenges His Naive Straight Friend To Bet His Booty On Game & Wins It”

”BottomGames - Muscle Hunk Challenges His Naive Straight Friend To Bet His Booty On Game & Wins It”

IFuckedYourGF 1 year ago

Tom Baker Trains His Slave to be World Class at Sucking Cock Pt 2 (4K)

66% 4K 0:22 / 13:50

Tom Baker Trains His Slave to be World Class at Sucking Cock Pt 2 (4K)

Clips4sale 1 year ago

The Calvorine: Trapped and Nuttered (Fail Clip)

The Calvorine: Trapped and Nuttered (Fail Clip)

Clips4sale 1 year ago

”Whoever Wins Gets To Fuck The Other.”

”Whoever Wins Gets To Fuck The Other.”

Zatube 2 years ago

Milos Ice Bath Challenge HD

63% HD 0:30 / 55:53

Milos Ice Bath Challenge HD

Clips4sale 1 year ago

”BottomGames - Muscle Hunk Challenges His Naive Straight Friend To Bet His Booty On Game & Wins It”

”BottomGames - Muscle Hunk Challenges His Naive Straight Friend To Bet His Booty On Game & Wins It”

Zatube 1 year ago

Patrick Knight starts his challenge in the pit

Patrick Knight starts his challenge in the pit

PornDR 1 year ago

”THE EASY GAY LIFE - Roman Todd, Cliff Jensen”

”THE EASY GAY LIFE - Roman Todd, Cliff Jensen”

ThePornstar 2 years ago

”THE OTHER SIDE - Scott Finn, Grayson Lange”

”THE OTHER SIDE - Scott Finn, Grayson Lange”

Trashreality 1 year ago

Gorgeous JT Frost fucked the hairy asshole of Mike Challenger in their take turns foursome session

Gorgeous JT Frost fucked the hairy asshole of Mike Challenger in their take turns foursome session

GayCK 1 year ago

Blow challenge: without a love glove - Pierce Paris with Nic Sahara sixty-9 shag

Blow challenge: without a love glove - Pierce Paris with Nic Sahara sixty-9 shag

2BGay 1 year ago

Hot freshmens made to complete challenge set by frat

Hot freshmens made to complete challenge set by frat

BoyFriendTV 13 years ago

Challenges part 1

Challenges part 1

BoyFriendTV 3 years ago

Highly Steaming Dual Spunk

Highly Steaming Dual Spunk

GayDudesFucking 1 year ago

Today's competition: a self-fuck faux-cock challenge

Today's competition: a self-fuck faux-cock challenge

BoyFriendTV 10 years ago

Atonement

ThePornstar 1 year ago

The Never Ending BDSM Challenge That Almost Took My Soul Continues

The Never Ending BDSM Challenge That Almost Took My Soul Continues

FapHouse 1 year ago

”Gym partners can't hide their gay feelings”

”Gym partners can't hide their gay feelings”

ThePornstar 2 years ago

Grayson Lange as a challenge up his sleeve

Grayson Lange as a challenge up his sleeve

PornGem 2 years ago

Missionary Boys: Giant cock Elder Esplin challenge

Missionary Boys: Giant cock Elder Esplin challenge

GayTubesTV 5 years ago

Dakota Lovell: Axel Kane amongst Dakota Lovell challenge

Dakota Lovell: Axel Kane amongst Dakota Lovell challenge

GayTubesTV 4 years ago

BoyCreeper.com - Young Lance Weber challenge

BoyCreeper.com - Young Lance Weber challenge

GayTubesTV 5 years ago

Muscle stud Max Wide slamming golliath dildo before Bobby Ryker hand fisted his hole

Muscle stud Max Wide slamming golliath dildo before Bobby Ryker hand fisted his hole

Eporner 2 years ago

FalconStudios - Attractive cowboy goes in for challenge

FalconStudios - Attractive cowboy goes in for challenge

GaysTubes 4 years ago

Gay Test 3, 2, 1

43% 0:15 / 10:22

Gay Test 3, 2, 1

Clips4sale 2 years ago

The fellow came from school and fapped off in the wc while his parents were working

The fellow came from school and fapped off in the wc while his parents were working

2BGay 2 years ago

Piss afternoon in park2: DIRTY, SMELLY, WET

Piss afternoon in park2: DIRTY, SMELLY, WET

AbGay 2 years ago

A young fellow touches his manmeat

A young fellow touches his manmeat

4Gay 2 years ago

The stud relieves himself taking a tub, faps off his salami and shoots a load

The stud relieves himself taking a tub, faps off his salami and shoots a load

4Gay 2 years ago

Twink's Favorite Is Cum Control.ep. 3-5

HD 0:39 / 14:46

Twink's Favorite Is Cum Control.ep. 3-5

FapHouse 2 years ago

GDude-JP - Pounding with supah sizzling model

GDude-JP - Pounding with supah sizzling model

GayDudesFucking 2 years ago

”Numero 2”

Fapnow 2 years ago

Brotherly Challenge - Ryland Kingsman, Johnny Bandera

Brotherly Challenge - Ryland Kingsman, Johnny Bandera

OurGay 2 years ago

Pain slut Dakota Wolfe takes the 30MT Challenge

Pain slut Dakota Wolfe takes the 30MT Challenge

OurGay 2 years ago

Boy swallows whole MP4

Boy swallows whole MP4

Clips4sale 2 years ago

Rubber Band Challenge to Balls(horizontal)

Rubber Band Challenge to Balls(horizontal)

Clips4sale 2 years ago

Deepthroating Slim Twink Magic C Until He Fills My Mouth With His Thick Cum. His Massive Cock Was A Challenge For My Throat

Deepthroating Slim Twink Magic C Until He Fills My Mouth With His Thick Cum. His Massive Cock Was A Challenge For My Throat

AbGay 2 years ago

Lusty gay dude Mike Challenger faps his hairy schlong

Lusty gay dude Mike Challenger faps his hairy schlong

AbGay 2 years ago

Louis Ricaute was ready for the BBC challenge

Louis Ricaute was ready for the BBC challenge

BoyFriendTV 1 year ago

”Brotherly Challenge”

”Brotherly Challenge”

4Wank 2 years ago

RIKKI HOGTIED in LATEX on the ROTATE TABLE FHD 50fps 1080p

HD 0:30 / 21:23

RIKKI HOGTIED in LATEX on the ROTATE TABLE FHD 50fps 1080p

Clips4sale 2 years ago

GloryholeAndHandjobs: Enrique display black manmeat

GloryholeAndHandjobs: Enrique display black manmeat

UrGayPorn 2 years ago

Winter Barefoot Snow Challenge 19 Jan 24

Winter Barefoot Snow Challenge 19 Jan 24

Clips4sale 2 years ago

Muscle Hunks Bareback Pounding

Muscle Hunks Bareback Pounding

TwinksNHunks 2 years ago

RIKKI AND MECHANICAL TICKLING MACHINE multicam (FHD mp4)

RIKKI AND MECHANICAL TICKLING MACHINE multicam (FHD mp4)

Clips4sale 2 years ago

ZEUS PAINFUL ROPE BONDAGE HD 720p

HD 0:27 / 25:48

ZEUS PAINFUL ROPE BONDAGE HD 720p

Clips4sale 2 years ago

5. Deepthroat Swallowing Corey, a Hung XTube Fan

5. Deepthroat Swallowing Corey, a Hung XTube Fan

AbGay 2 years ago

Slow Strip - Huge Plug - Cum

Slow Strip - Huge Plug - Cum

FapHouse 2 years ago

Sissy Toy Challenge

HD 0:24 / 10:26

Sissy Toy Challenge

Clips4sale 2 years ago

Bas Restrained and CBT

65% 0:59 / 19:04

Bas Restrained and CBT

Clips4sale 2 years ago

Twink's Favorite Is Cum Control.ep. 4-5

HD 0:39 / 14:46

Twink's Favorite Is Cum Control.ep. 4-5

FapHouse 2 years ago

No hands HUMUNGOUS EBONY SCHLONG

No hands HUMUNGOUS EBONY SCHLONG

2BGay 3 years ago

Gay sex cute young homo New stud Ryan Morriassociate's son faces a meaty challenge: the

Gay sex cute young homo New stud Ryan Morriassociate's son faces a meaty challenge: the

Eporner 2 years ago

Teenager bro tries penis blowing challenge gay family

Teenager bro tries penis blowing challenge gay family

SexTubeSpot 5 years ago

Qwop: a running challenge

Qwop: a running challenge

SexTubeSpot 2 years ago

GayAsianNetwork: Very torrid Yura among Takashi rock hard rump humped

GayAsianNetwork: Very torrid Yura among Takashi rock hard rump humped

UrGayPorn 2 years ago

NICKY GLOBAL CHALLENGE CUM or TICKLING multicam (HD mp4) 720p

HD 0:28 / 18:34

NICKY GLOBAL CHALLENGE CUM or TICKLING multicam (HD mp4) 720p

Clips4sale 2 years ago

Brotherly Challenge - BrotherCrush

Brotherly Challenge - BrotherCrush

OurGay 2 years ago

Religious Worthiness Interview Turns Into Full Blown Fuck Sesh

Premium 4K 37:46

Religious Worthiness Interview Turns Into Full Blown Fuck Sesh

SayUncle 2 years ago

”Alex Montenegro & Sash West challenges their stepdads to do pushups”

”Alex Montenegro & Sash West challenges their stepdads to do pushups”

429Men 1 year ago

”Jock has his butt creampied after deep & raw penetration”

”Jock has his butt creampied after deep & raw penetration”

Rainblow 1 year ago

”Sucking Straight Johnny Meat”

”Sucking Straight Johnny Meat”

Trashreality 1 year ago

”Long haired hearthrob Christop gags on Timarrie Bakers big & hard ebony shaft”

”Long haired hearthrob Christop gags on Timarrie Bakers big & hard ebony shaft”

Trashreality 1 year ago

Solo: Big Dicked Tex, Up for a Challenge

Solo: Big Dicked Tex, Up for a Challenge

GayJack 1 year ago

White girl Jessica Diamond anal challenged by big black cock

White girl Jessica Diamond anal challenged by big black cock

YouPorn Unknown

Handsome Nick drilled the hairy asshole of sexy Mike Challenger in the bathroom

Handsome Nick drilled the hairy asshole of sexy Mike Challenger in the bathroom

UrGayPorn 1 year ago

Wild Men, Scene #01

Wild Men, Scene #01

Some.Porn 1 year ago

Game On Part 1

Premium HD 20:37

Men 8 years ago

Chubby Man Vs. Jobber: Fighting on the Bed

Chubby Man Vs. Jobber: Fighting on the Bed

FapHouse 1 year ago

”Winner Alfonso Osnaya gets all the fucking as Grant Ducati bottoms”

”Winner Alfonso Osnaya gets all the fucking as Grant Ducati bottoms”

Trashreality 1 year ago

Adam Ramzi survives thirty minutes of Van Darkholme -Censored- torment

Adam Ramzi survives thirty minutes of Van Darkholme -Censored- torment

Yeswegays 1 year ago

Str8 Boy Seeking His Prostate

HD 1:01 / 15:19

Str8 Boy Seeking His Prostate

FapHouse 1 year ago

Serviced: Staying Hard in Challenging Conditions

Serviced: Staying Hard in Challenging Conditions

GayTubesTV 1 year ago

Passive aguas lindas benjamin Deli Challenge trend 2

Passive aguas lindas benjamin Deli Challenge trend 2

XHamster 1 year ago

Curvy Conversion Audio: Surrender to the Truth of your Attraction or Repulsion by OctoGoddess ft: Encouraged Gay, BBW Worship, Binaural Beats

HD 0:28 / 10:17

Curvy Conversion Audio: Surrender to the Truth of your Attraction or Repulsion by OctoGoddess ft: Encouraged Gay, BBW Worship, Binaural Beats

Clips4sale 1 year ago

masturbating myself off while at my job

masturbating myself off while at my job

Gayhub 1 year ago

Tied Myself up to Do This Hands-free Cum Challenge

Tied Myself up to Do This Hands-free Cum Challenge

FapHouse 1 year ago

Cute Boy Takes His First Huge Cock

HD 0:39 / 20:23

Cute Boy Takes His First Huge Cock

FapHouse 1 year ago

legitimate YEARS SENIOR DUDES MORNING

legitimate YEARS SENIOR DUDES MORNING

Gayhub 1 year ago

Ultra-cute wondrous guy pulverizes with hefty beefsticks , dildak and father's good-sized penis!

Ultra-cute wondrous guy pulverizes with hefty beefsticks , dildak and father's good-sized penis!

4Gay 1 year ago

Getting My Stepbrother Wet

Premium 4K 18:49

Getting My Stepbrother Wet

SayUncle 5 years ago

Gustavo Alves and Martino Paiva

Gustavo Alves and Martino Paiva

Fapnado 1 year ago

Good Boy

XHamster 1 year ago

Young Challenge Video With Cyrus Stark

Young Challenge Video With Cyrus Stark

AbGay 1 year ago

Suited bear in fourway with twinks

Suited bear in fourway with twinks

Some.Porn 1 year ago

Heavyhitterboxer’s Domination: the Ultimate Submission Challenge

Heavyhitterboxer’s Domination: the Ultimate Submission Challenge

FapHouse 1 year ago

Gay Challenge: If You Cum You Eat It - 720p mp4

Gay Challenge: If You Cum You Eat It - 720p mp4

Clips4sale 1 year ago

”Interracial gay assfucking under the trees - Ryan Rose & Pheonix Fellington”

”Interracial gay assfucking under the trees - Ryan Rose & Pheonix Fellington”

Rainblow 2 years ago

”Sexy ass Jaxon Colt gets drilled by James Jamessons huge dick”

”Sexy ass Jaxon Colt gets drilled by James Jamessons huge dick”

Zatube 2 years ago

dick enlargement challenge DAY 4... big balls

dick enlargement challenge DAY 4... big balls

XHamster 1 year ago

Jism with my Uncircumcised penis, foreskin and sack of babymakers

Jism with my Uncircumcised penis, foreskin and sack of babymakers

4Gay 1 year ago

Deepthroating Slim Twink Magic C Until He Fills My Mouth With His Thick Cum. His Massive Cock Was a Challenge for My Throat

Deepthroating Slim Twink Magic C Until He Fills My Mouth With His Thick Cum. His Massive Cock Was a Challenge for My Throat

XHamster 3 years ago

”Gay car mechanics - Brandon Anderson & Roman Todd”

”Gay car mechanics - Brandon Anderson & Roman Todd”

Faptor 2 years ago

Masturbating while pouring cold water

Masturbating while pouring cold water

XVideos 2 years ago

Can testicles taste food? Fact or CAP? - TikTok Challenge

Can testicles taste food? Fact or CAP? - TikTok Challenge

XVideos 2 years ago

”Christian Wilde takes the challenge of cbt & water spray torment”

”Christian Wilde takes the challenge of cbt & water spray torment”

Fapnow 1 year ago

European boys - Twink cum splashers

European boys - Twink cum splashers

FapHouse 7 years ago

DAY6 - 7 Days cum Challenge - One Week cum challenge - Everyday Cum challenge

DAY6 - 7 Days cum Challenge - One Week cum challenge - Everyday Cum challenge

XVideos 1 year ago

Silver Daddy Boxer Gutpunch Me Without Gloves

Silver Daddy Boxer Gutpunch Me Without Gloves

XHamster 11 months ago

92 93 94 95 96

11,707 results found

Related categories

Competition Tease Contest Edging Football Training Submissive In Control Humiliation Messy Funny Noisy Game Punk Begging WTF Jerking Off Worship Locker Room Hazing

Narrow your search

edging challenge cock hero challenge jerk off challenge cum challenge try not to cum challenge edge challenge joi challenge dont cum challenge goon challenge dildo challenge stroke challenge do not cum challenge jerk challenge escape challenge blowjob challenge cum twice challenge naked challenge masturbation challenge tickle challenge wank challenge

Categories Pornstars

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.