Jizz

Post a sexy picture on r/tgw for the 1st time while at an [8]? Challenge Accepted

treesgonewild

My first time beating the Chest was also my first time beating the Purist challenge!

bindingofisaac

Time for seconds. Have a seat if you feel so inclined, gotta have a challenge, right?

ladybonersgw

I havent posted in a long time, how about that bottle challenge thing.

MassiveCock, penis

10 min push-up challenge. First time in the 300 club!

ladybonersgw

[F] That's right ... I wear lace to the gym! Day 1 of the WOGW Unofficial Mod Challenge. It's time to get fit.

Workoutgonewild

30 Day workout and diet challenge - Day 4. I wonder if it matters at what time you post to get more views :)

ladybonersgw

(F)first time on Reddit, accepting a challenge! Should I continue?

gonewild

Ice bucket challenge started in Russia long time ago.

ANormalDayInRussia

Posted some time ago about an upcoming hysterectomy and the challenges I was experiencing because I'm only 25 and cf. I wanted to update and share what a difference the hysterectomy has already made. May be NSFW: Innards

childfree

Challenge #2! Who did I draw? Thanks for the feedback last time.

boltedontits

I enjoy a challenge, which is why i post pictures of my face at stupid times of the day.

GoneWildCD

New challenge for a (f)an. 1000 gets a pussy face shot ;) not a cat this time lol

gonewild

I keep hearing about the charliecharlie challenge thing. Every time I read about it I just imagine this.

Supernatural

Handlebra: because I misread September's challenge every. single. time.

GoneMild, Veronica1993

Ranuary Challenge (05 / 31): Cuddle time with Yukari (Warning: Slightly NSFW!)

touhou

Tp roll challenge: Maybe a bigger tube next time?

NSFWChallenges

I challenge /r/celebjomaterial to cum to Demi Lovato's butthole within 3 minutes (post time in comments)

CelebJOMaterial

Was told in my last post that my one finger challenge was done incorrectly! Hope i have the right hole this time around! ;D

AsiansGoneWild, Dollywinks, anal, scrolller_com, PerPornArchive

40, sober nearly 2 years, trying to exercise to gain more muscle but it's challenging. Step father to 3 teenagers, full time job sitting 40 hours a week. Down 35 pounds since sobriety...

normalnudes

For your next time she promised a challenge. And she delivered.

suckingtogether

Unleashed Her First Cum Face x 4 Sex Scenes <Her First Ever> Cum Face x Lotion Play x Mega Cock x Cosplay Threesome Minami Explores Her Sexuality In First Time Ever Challenges! - SD -Minami Aizawa

JavDownloadCenter, bestof_gangbangs

Guys, are we doing the Heart-Shaped boob challenge? Because I missed out on the 1 finger challenge last time...

AsiansGoneWild, heartshapedboobgw

[M/S] Time to move on to his next challenge.

taboocaptions

Last time I posted my stash someone said it was lacking Premiums... Challenge accepted :>

ABDL

It’s time for a new seven day panty challenge. Everyone who leaves a nice comment on these will be entered and at the end of the week someone be randomly selected for a special treat

WickedBunny

30 days challenge - Day 17 - It’s time to cook (f)

gonewild

My butt sharpie challenge. 46 first time. Think I can beat it with help.

GaybrosGoneWild

[23] My wife challenged me to go the entire time of our trip home for Christmas without cumming and I could do whatever I wanted to her when we get home. Day 5 and these balls are full! Can't wait for the reward though ;)

tinydick

M. 22. ~250 lbs. 5'11". Trying this out for the first time. Trying to make sure you couldn't see any of my tattoos in the photo was a challenge lol.

normalnudes

Guess its daddy selfie time again. Me and my little are doing lent and giving up energy drinks. We've been really good and I took on the extra challenge of pizza too. So as a reward I got this shirt I found today! Now I'm a pizza daddy !

ddlg

Time to edge and tease my enormous cock! Need it milked and drained, my balls emptied to some slut. You upto the challenge? I'll send you videos too ? you can see my cock and my type on my profile, if you think you've got what it takes Kik is the same nam

jobuds

Slut Challenge: Hard Mode: Use Tinder to get tag teamed by 2 guys at the same time.

ilovesluts

[Male BTK] Included my feet this time for more of a challenge

DrawMeNSFW

Time for a real challenge

Ifyouhadtopickone

After every time we fuck, I'll make it a personal challenge to shoot cum on her face without getting any on her hijab

HijabGirls, MuslimSluts, raceplay, BrownHotties, pokimanehot, nsfwCaptionRequest

He had a bit of a reputation. [challenging] [implied] [first time together]

VanillaCaptions

Another anal challenge...butternut this time!..but it was way too big so couldn't get it all they way in...can't win them all :)!!![?][t]

AnalGW

There's just a little more time to get in on my Christmas challenge! More pics and vids are posted all the time, and the next gangbang is now on the radar! Come check me out!

OnlyFans101

He challenged me to see if I could make him cum a 2nd time in 20 mins. Challenge accepted! ?

GirlsFinishingTheJob, VerticalGifs

My Master challenged me to edge 100 times this weekend. I succeeded, so he rewarded me by ruining my cunt, my ass, and then my clit.

OrgasmDenial, TeaseAndDenial

It's Two Weeks Later And Times Are Even More Challenging --- But I Hope You're All Still (M)anaging To Find Ways To Smile

strikeaposegw

First time trying the sharpie challenge.

SharpieChallenge

[F]irst time attempting the challenge! Got to 15. Feel so stretched.

SharpieChallenge

Time For Challenge Number Two!

PornIsCheating

Challenge Time: Let's spread some positivity! ? Go and leave a lovely comment on 3 other GW posts you like and comment here to receive a little something in your DMs! (I will be checking you've done it?) (f)

gonewild

Wipe it down mirror challenge (showing my [f]ace for the second time)

gonewild, u_aretiff

First time striking a pose ... [M] felt like it was time for a challenge!

strikeaposegw

Challenge of the day - how many times can I get hubby to blow his load & how many different places can I take a cumshot? ??

Blowjobs

Time for a plank challenge?

AthleticBabes

A morning pixelart warmup learning Aseprite. I tried adapting one of my existing figure drawing sketches into a small sprite. It was a real challenge working with color for the first time.

PixelArtNSFW

Can you even see my thong? I challenge you to pull it out with your teeth, take as much time as you need.... Your local Thicc Latina (F) 45♥️?

ArizonaGirls

Challenge #7 Time to relax ?

KinkyChallenge

Challenge#7 time to relax

KinkyChallenge, GlitterQueenBeeXx

Challenge accepted! First time posting here and won't be the last!

PLASTT

Seems like I bought myself a challenge this time

ToysGW

First time using colored pencils exclusively to do a drawing....it was fun and challenging thank you to BareLeiaRose

DrawnYouNSFW

Here's a nice little challenge for you! ? Can you name all the ones on the smartphone? Haha, my OF now has a trivia section ? - Spoiler alert ? there will be more 'hardcore' porn quizzing but I will be the contestant next time! The full show will go onlin

u_chicktrainer

Popping a plug in for the first time in weeks is always a pleasant challenge (;

anal_gifs, whenitgoesin, Doggystyle_NSFW, buttplug

CHALLENGE: Distance Challenge, how far can I squirt? Guess how many centimeters I reached this first time ?? Any other girls willing to participate, I am up for the challenge ?❤️

squirting, u_lola_fontaine69, u_Lonely_Self_6024, u_MTF_12, u_Suspicious-Rabbit835, squirtinggonewild