Challenge Videos - Gay (11,031)

House dom Trenton Ducati taking the 30MT challenge

House dom Trenton Ducati taking the 30MT challenge

Yeswegays 1 year ago

Sexy Ass Twink gets Held Down and Spitroasted RAW

Sexy Ass Twink gets Held Down and Spitroasted RAW

GayXPS 1 year ago

Time for a bodysuit

Time for a bodysuit

xHamster 1 year ago

A young man stroked off his manstick and jism on the floor

A young man stroked off his manstick and jism on the floor

4Gay 1 year ago

ClubBangBoys - Shaved twink Seal Kris digs challenge

ClubBangBoys - Shaved twink Seal Kris digs challenge

GayTubesTV 3 years ago

BoyCreeper.com - Chris Colt challenge sex tape

BoyCreeper.com - Chris Colt challenge sex tape

GayTubesTV 5 years ago

Gay Compilation #38 Try Not Cum Challenge 4 Min With Gay Porn

Gay Compilation #38 Try Not Cum Challenge 4 Min With Gay Porn

AbGay 2 years ago

Young man sucks two cocks and receives cum in threesome

Young man sucks two cocks and receives cum in threesome

Eporner 2 years ago

”Lustful Sean likes to suck babe Adam big hard meat”

”Lustful Sean likes to suck babe Adam big hard meat”

StarWank 2 years ago

Boys challenge blowjob and gay sex tits drink We were thrilled to get Jerry Ford together

Boys challenge blowjob and gay sex tits drink We were thrilled to get Jerry Ford together

Eporner 2 years ago

Dumb and bulging

55% 0:11 / 28:00

Dumb and bulging

Clips4sale 2 years ago

Machine Challenge: Dominic Pacifico

Machine Challenge: Dominic Pacifico

OurGay 1 year ago

GDude-JP - Model group-tear up romp gig

GDude-JP - Model group-tear up romp gig

UrGayPorn 1 year ago

Working gay: the challenges of same-sex relationships in the workplace

Working gay: the challenges of same-sex relationships in the workplace

SexTubeSpot 2 years ago

”Elder Hill: Hole Training”

”Elder Hill: Hole Training”

StarWank 2 years ago

Public Bathroom Jerk Off

Public Bathroom Jerk Off

GayXPS 2 years ago

HETEROFLEXIBLE - How Guys Climax With Glamorous Guy Jayden Marcos! SEE HIM JACK OFF! TOTAL EPISODE

HETEROFLEXIBLE - How Guys Climax With Glamorous Guy Jayden Marcos! SEE HIM JACK OFF! TOTAL EPISODE

4Gay 2 years ago

Venus 2000 milking machine: maximum speed in 5 minutes

Venus 2000 milking machine: maximum speed in 5 minutes

SexTubeSpot 2 years ago

Searching for poseidons trident: a video challenge

Searching for poseidons trident: a video challenge

SexTubeSpot 2 years ago

Shower Shy

Premium 4K 20:29

BullyHim 3 years ago

Tyler's next challenge is a massive cock from Will Harvey.

Tyler's next challenge is a massive cock from Will Harvey.

Nuvid 11 years ago

Ebony stud Nathan Woods has a truly impressive dick that might intimidate lesser men. Always up for a challenge, master bottom Jay Ross opens wide and swallows it like a champion, stretching his lips around Nathan's girth as it fills his gullet inch by in

Ebony stud Nathan Woods has a truly impressive dick that might intimidate lesser men. Always up for a challenge, master bottom Jay Ross opens wide and swallows it like a champion, stretching his lips around Nathan's girth as it fills his gullet inch by in

ProPorn 13 years ago

Twink is turned gay after having huge cock in his ass

Twink is turned gay after having huge cock in his ass

UrGayPorn 2 years ago

The Gay Simple Life Ep 1: The Big Rig Driving Challenge - NakedSword Originals

The Gay Simple Life Ep 1: The Big Rig Driving Challenge - NakedSword Originals

OurGay 1 year ago

Want Me to Extend My Challenge?

Want Me to Extend My Challenge?

FapHouse 9 months ago

Sprayer Jay Fucked Student Jakub

HD 0:39 / 18:57

Sprayer Jay Fucked Student Jakub

FapHouse 8 months ago

Gay or Nay?

HD 0:27 / 13:45

Clips4sale 9 months ago

Stroking off in an edging compete game (effortless mode)

Stroking off in an edging compete game (effortless mode)

4Gay 8 months ago

February 2025 Video Challenge #16

February 2025 Video Challenge #16

FapHouse 8 months ago

4# Cumshot Challenge - XL Cock with Foreskin at Gloryhole

4# Cumshot Challenge - XL Cock with Foreskin at Gloryhole

xHamster 8 months ago

Naked Yoga - 8 Minutes Tantric Masturbation, Kegel Exercises and Abs Workout - Fitness Challenge

Naked Yoga - 8 Minutes Tantric Masturbation, Kegel Exercises and Abs Workout - Fitness Challenge

RedTube Unknown

Cum Control Challenge!! How Long Can YOU Last Edging?!?!

Cum Control Challenge!! How Long Can YOU Last Edging?!?!

YouPorn Unknown

Ripped Gay Jocks Fucking Ass in the Sunshine

Ripped Gay Jocks Fucking Ass in the Sunshine

XXXShake 1 year ago

Found my prostate during FAILED edging timed challenge (Jay Stroke)

Found my prostate during FAILED edging timed challenge (Jay Stroke)

YouPorn Unknown

Fisting Central: Fist Club Newbies Take on a Challenge

Fisting Central: Fist Club Newbies Take on a Challenge

GaysTubes 8 months ago

Eric Gets His Holes Used

Eric Gets His Holes Used

xHamster 9 months ago

DAY3 - 10 Days cum Challenge - Everyday Cum with Bestvibe Male Sextoy Masturbator Clip 1

DAY3 - 10 Days cum Challenge - Everyday Cum with Bestvibe Male Sextoy Masturbator Clip 1

xHamster 8 months ago

Ruin Orgasm Edgemeplease Cum Shot Challenge

HD 0:39 / 12:30

Ruin Orgasm Edgemeplease Cum Shot Challenge

FapHouse 8 months ago

2172 deux heteros virils acceptent un challengej ai lance un challenge a deux...

2172 deux heteros virils acceptent un challengej ai lance un challenge a deux...

PornBox 5 years ago

Planking challenge by Drew Dixon and Ethan Chase turns to hot sex

Planking challenge by Drew Dixon and Ethan Chase turns to hot sex

PornGem 9 months ago

Big Dick for a Giant

HD 0:39 / 11:02

Big Dick for a Giant

FapHouse 9 months ago

Top five Boys - Beach Soiree Challenge at Flirt4Free

Top five Boys - Beach Soiree Challenge at Flirt4Free

Gayhub 9 months ago

Friendly Wrestling Match Becomes Sexy Fucking

Friendly Wrestling Match Becomes Sexy Fucking

FapHouse 9 months ago

Ugh. Uploading a Large File Is Painful

Ugh. Uploading a Large File Is Painful

FapHouse 9 months ago

”Markie & Dominic”

”Markie & Dominic”

Trashreality 9 months ago

Edging. No Cum - Day 3

HD 0:39 / 13:03

Edging. No Cum - Day 3

FapHouse 9 months ago

ManUpFilms - Queer Colby Jansen condom-free compete

ManUpFilms - Queer Colby Jansen condom-free compete

Gayhaus 1 year ago

The Challenge of Putting a Tennis Ball in Your Ass!

The Challenge of Putting a Tennis Ball in Your Ass!

FapHouse 10 months ago

Youngster strokes off his magnificent man sausage and spunks!

Youngster strokes off his magnificent man sausage and spunks!

Gayhub 11 months ago

Even the large head on his cock was quite the challenge to take in

Even the large head on his cock was quite the challenge to take in

Yeswegays 10 months ago

Part 1 - Edging Challenge Reaction Video

Part 1 - Edging Challenge Reaction Video

FapHouse 10 months ago

Alex Montenegro and Sash West challenges their stepdads to do pushups

Alex Montenegro and Sash West challenges their stepdads to do pushups

MenGem 1 year ago

Fuck Challenge Uiy

Fuck Challenge Uiy

MrGay 1 year ago

Jock has his ass creampied after deep and raw penetration

Jock has his ass creampied after deep and raw penetration

Fapnado 1 year ago

Wild Gay Audition - Dirty Scout's Ultimate Blowjob Challenge

Wild Gay Audition - Dirty Scout's Ultimate Blowjob Challenge

GayxXxWorld 1 year ago

”Kinky Nate Grimes submits to Sebastian Keys torment challenge”

”Kinky Nate Grimes submits to Sebastian Keys torment challenge”

StarWank 1 year ago

Cumshot Challenge - Uncut Xl Cock at the Gloryhole

Cumshot Challenge - Uncut Xl Cock at the Gloryhole

FapHouse 8 months ago

Missionary Boys: Elder's Hard Stretching Challenge

Missionary Boys: Elder's Hard Stretching Challenge

GayPornoTube 8 months ago

”Lusty Nic Sahara & two more dudes prepared their cocks & asses for a hardcor”

”Lusty Nic Sahara & two more dudes prepared their cocks & asses for a hardcor”

ThePornstar 8 months ago

Masonic boy&#039_s 1st anal sex challenge! Dylan Tides anal fucked by the muscular DILF Tyler Saint! The old man hammers his piston deeper and deeper into the boy&#039_s hole!

Masonic boy&#039_s 1st anal sex challenge! Dylan Tides anal fucked by the muscular DILF Tyler Saint! The old man hammers his piston deeper and deeper into the boy&#039_s hole!

XVideos 9 months ago

Silver Daddy Boxer Gutpunch Me Without Gloves

Silver Daddy Boxer Gutpunch Me Without Gloves

FapHouse 8 months ago

PRECUM ALL DAY!! part-two Leaky-Faucet

PRECUM ALL DAY!! part-two Leaky-Faucet

Gayhub 8 months ago

Asian Cock Edging Challenge

Asian Cock Edging Challenge

FapHouse 8 months ago

”Mature makes his lover ride his large cock deep”

”Mature makes his lover ride his large cock deep”

Zatube 6 months ago

Legrand Wolf hones bareback skills on my willing tight ass

Legrand Wolf hones bareback skills on my willing tight ass

FetishShrine 6 months ago

Muscular Legrand Wolf Tests Bareback Skills On My Open Ass

Muscular Legrand Wolf Tests Bareback Skills On My Open Ass

Eporner 6 months ago

”Gustavo Alves & Martino Paiva”

”Gustavo Alves & Martino Paiva”

Zatube 6 months ago

Slow Motion Sex Challenge Mixed Clips Comparison

Slow Motion Sex Challenge Mixed Clips Comparison

xHamster 6 months ago

The Great Bananass Challenge!

The Great Bananass Challenge!

XVideos 3 years ago

Try not to cum challenge with anal masturbation

Try not to cum challenge with anal masturbation

YouPorn Unknown

”Jeffrey has hardcore assfucking fest with Mike Challenger”

”Jeffrey has hardcore assfucking fest with Mike Challenger”

IFuckedYourGF 6 months ago

Handjob Home Alone

Handjob Home Alone

FapHouse 7 months ago

The End of Ageism

The End of Ageism

xHamster 7 months ago

On the edge

xHamster 7 months ago

”Robert Axel endures shocks from zapper & water spray torment”

”Robert Axel endures shocks from zapper & water spray torment”

Zatube 7 months ago

Jack Andy and Seth Santoro turn to missionary at the end

Jack Andy and Seth Santoro turn to missionary at the end

HOMO.XXX 7 months ago

Punch Challenge - Benjamin Blue And Ace Quinn

Punch Challenge - Benjamin Blue And Ace Quinn

AbGay 1 year ago

Noah White takes Legrand Wolfs massive king dick with effort

Noah White takes Legrand Wolfs massive king dick with effort

VikiPorn 6 months ago

”Pierce Paris gave Tony Orlando hard punishment after pissing him off”

”Pierce Paris gave Tony Orlando hard punishment after pissing him off”

Zatube 6 months ago

Trio Takes on the Challenge

Trio Takes on the Challenge

GaysTubes 6 months ago

Hairy Dude Gets Drilled By Horny Twink - NextDoorBuddies

Hairy Dude Gets Drilled By Horny Twink - NextDoorBuddies

XXXShake 1 year ago

”Sucking Str8 Boy Johnny Dick”

”Sucking Str8 Boy Johnny Dick”

Trashreality 9 months ago

John Stone Vs Spencer Reed the Oil Match

HD 0:39 / 45:41

John Stone Vs Spencer Reed the Oil Match

FapHouse 9 months ago

ZIGFRID and RIKKI LATEX CHALLENGE HD 720p

HD 0:20 / 16:40

ZIGFRID and RIKKI LATEX CHALLENGE HD 720p

Clips4sale 9 months ago

Don't Cum If You Want To Go To The Party – Anime JOI Challenge

Don't Cum If You Want To Go To The Party – Anime JOI Challenge

GayXhub 9 months ago

jack hunter challenging goody two shoes devin franco

jack hunter challenging goody two shoes devin franco

FetishShrine 9 months ago

Cum Challenge 2.0 - Hardcore Gloryhole Action

Cum Challenge 2.0 - Hardcore Gloryhole Action

FapHouse 8 months ago

DAY1 - 10 Days cum Challenge - Bestvibe Best Male Sextoy Masturbator for gays

DAY1 - 10 Days cum Challenge - Bestvibe Best Male Sextoy Masturbator for gays

GayXhub 5 months ago

HETEROMANIA JIZZ CONTEST 11 - Who Cums More?

HETEROMANIA JIZZ CONTEST 11 - Who Cums More?

WebcamBros 5 months ago

”Dorm students Erick & Raymond are sucking dicks as gay for pay”

”Dorm students Erick & Raymond are sucking dicks as gay for pay”

Zatube 5 months ago

Cum Control Challenge with Danny D

Cum Control Challenge with Danny D

GayXo 1 year ago

Ice Breaker Challenge with Jaxon Valor & Russel West

HD 1:01 / 20:20

Ice Breaker Challenge with Jaxon Valor & Russel West

FapHouse 5 months ago

Cum With Me Dont Cum Challenge

Cum With Me Dont Cum Challenge

AbGay 4 months ago

Ice Breaker Challenge with Jaxon Valor & Russel West

Ice Breaker Challenge with Jaxon Valor & Russel West

xHamster 5 months ago

”Samuel & Mauricio”

”Samuel & Mauricio”

Zatube 4 months ago

”DADDY'S PRIDE & JOY Tape 8 - Chess”

”DADDY'S PRIDE & JOY Tape 8 - Chess”

LesbianBliss 4 months ago

How to Ask for What You Want

How to Ask for What You Want

xHamster 4 months ago

You're Only Allowed to Touch Yourself if I'm Around

4K 0:46 / 30:11

You're Only Allowed to Touch Yourself if I'm Around

SayUncle 10 months ago

Matt & Leo Have to Hook Up - Getting off on My Homo Homies

Matt & Leo Have to Hook Up - Getting off on My Homo Homies

Gayhub 4 months ago

”FleshPotFilms: Brett Tyler Faces Intense Preparation Before His Cooking Challeng”

”FleshPotFilms: Brett Tyler Faces Intense Preparation Before His Cooking Challeng”

Rainblow 4 months ago

”Ramon Lima & Francisco Macedo”

”Ramon Lima & Francisco Macedo”

LesbianBliss 4 months ago

Surprise! Playing with the Tail Again!

Surprise! Playing with the Tail Again!

FapHouse 3 months ago

”FleshPotFilms: Brett Tyler Faces Intense Preparation Before His Cooking Challeng”

”FleshPotFilms: Brett Tyler Faces Intense Preparation Before His Cooking Challeng”

429Men 3 months ago

Failing NO NUT NOVEMBER, boys still boys, they need to ejaculate. Twink in white briefs stroking on bed

Failing NO NUT NOVEMBER, boys still boys, they need to ejaculate. Twink in white briefs stroking on bed

SissyFlix 1 year ago

Stud in Supense

Stud in Supense

xHamster 3 months ago

Lesson 6. Day 6. First Multiorgasmic Sensations

Lesson 6. Day 6. First Multiorgasmic Sensations

FapHouse 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

HD 0:39 / 10:48

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

FapHouse 2 years ago

Curious Straight Guy - First Gay Blowjob Experience

HD 0:09 / 12:52

Curious Straight Guy - First Gay Blowjob Experience

Sketboy 10 months ago

No. Ksgh14 Climax Lab Ep.54 Foreskin Twink’s Urethral Play Extreme Challenge. Ep.1

No. Ksgh14 Climax Lab Ep.54 Foreskin Twink’s Urethral Play Extreme Challenge. Ep.1

FapHouse 5 months ago

i love a challenge

i love a challenge

PornOne 5 months ago

Anal Challenge - Chapter #02

Anal Challenge - Chapter #02

PornUse 4 months ago

”Mauricio & Samuel”

”Mauricio & Samuel”

LesbianBliss 4 months ago

”University students Erick & Raymond are sucking dicks as gay for pay”

”University students Erick & Raymond are sucking dicks as gay for pay”

LesbianBliss 4 months ago

No.ksgh17 Climax Lab Ep.56 『super Stamina Stud’s First Controlled Release』ep.1-4

HD 1:01 / 17:01

No.ksgh17 Climax Lab Ep.56 『super Stamina Stud’s First Controlled Release』ep.1-4

FapHouse 4 months ago

Rafael and Rocco

Rafael and Rocco

BelamiOnline 8 years ago

challenged trailer

challenged trailer

XVideos 12 years ago

Can nads taste food? Fact or CAP? - TikTok Compete

Can nads taste food? Fact or CAP? - TikTok Compete

Gayhub 8 months ago

Edge Me Please! Cum Control Challenge

Edge Me Please! Cum Control Challenge

FapHouse 8 months ago

Interactive Cocktober Challenge 2025!

Interactive Cocktober Challenge 2025!

LoyalFans 8 months ago

Cumshot Challenge can this young bi guy last long enough to break the record

Cumshot Challenge can this young bi guy last long enough to break the record

Eporner 7 months ago

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