Jizz

I love bruises, but I don't mark easily. Would any of you ladies be up for the challenge?

dykesgonewild

The response to my challenge was so good that I [f]elt everyone should win :) [P.S. it's still inside me right now while I type this. I used to be such a good girl, what have you done to me GW?]

gonewild

My Roommate told me it's not possible to be sexy in these pajamas. I said challenge accepted what does gonemild think?

GoneMild

Tied up and waiting to be taken. Who is up for the challenge o[f] taming this wild one.

gonewild

Never had anyone able to deep throat me. :( Anyone think they would be up to the challenge?

MassiveCock

i could use a fuck buddy...i think if your up for the challenge it would be fun ;] (bonus facial features in comments)

ladybonersgw

That'll be a challenge

TitsAssandNoClass, HugeDickTinyChick

I know this is probably going to be fucked up but I was waiting for a queen to do this in this week's challenge

rupaulsdragrace

Holding these things up can be a challenge (f)

gonewild

Watching Taylor Swift live would be the real life version of a "You cum- you lose" challenge

CelebJOMaterial

Trying to study in this library can be quite challenging

librarygirls, u_F31sty

Fan requested mirror shot... this proved to be more challenging than I thought. Sorry for poor quality.

GoneMild

For the few people here... This challenge video will be posted soon! ;D x

KiamaFrost

First bad dragon toy is proving to be a challenge. ?

BadDragon

[oth] Whos ready to take the weekend cum challenge? By Monday you balls will be drained! Details inside

Sexsells, SidneyTanlines, throwaway855836

Would you be up to the challenge o[f] retraining my neglected ass?

gonewild

Failed an edging challenge, and lied to my mistress this could be a while... 24hrs and counting

chastity

Getting out of bed is turning out to be a real challenge today

Rubenesque_I_Am, TheMomNextDoor, onmww

We'd be oh so happy to entertain a third sometime... Who's up to the challenge? [F][M] ?

GWCouples

Think it will be a challenge? (18)

MassiveCock

This style of open front top is less common today, but was very popular a few years ago - challenging whether the boob should be revealed from above or below

AltBoobWorld

I [f]ound Acroyoga to be a great challenging workout! ?

Workoutgonewild

Still looking for the one that can convince her to be shared. Anyone up for the challenge?

WouldYouFuckMyWife

Tomorrow the denial challenge will be pinned and posted!

WorshipSelenaGomez, SelenaGomezTribute

Happy birthday to our divine Mistress! Today the denial challenge will be posted!

WorshipSelenaGomez

I heard this was a challenge a while back... anyone up for a revival? (First post here, be gentle!)

ChiveUnderground, ass

Spent most of my day off masturbating and the whole day braless. Challenging myself to be more confident in my sexuality. It's going pretty well. Here are my boobs!

bigonewild, GoneWildSmiles

She was proud, and justifiably so - but that could be her downfall, too... [challenge] [bet] [implied]

xxxcaptions, VanillaCaptions

the climb might be tough and challenging, but the view is worth it. [F/23]

gonewild, ass, booty_queens, UpvotedBecauseButt, collegesluts

Finally, 2 new bra's.. Can be a challenge with my size.. ??

BigBoobsGW

Finally found 2 new bra's! It can be a challenge ??

LingeriePlus

I have an Idea to Try different Dildo's. Would that Be a nice Challenge guys?

sexchallenges

This should be a challenge :P

TrueFMK

Gonna be a challenge not to whip my dick out and start jerking off to Florence Pugh and ScarJo during the Black Widow movie

JerkOffToCelebs, celebJObuds

I've decided that this year there is going to be a challenge aspect to each of your unlocks.

keyholdercaptions, femdomcaptions, HumiliationCaptions

clalaclan philias' glistening bust while being porked (Ltt challenger)[shining series]

hentai, u_BarGamer

Would this be a challenge for your throat? ?

MassiveCock

DP with large Austin - this knot is going to be a fun challenge

BadDragon

Down 20kg (45lbs for the metrically challenged) since February 1st. SW:~135kg, CW:114kg, 16:8, Low carb. This is halfway to where I need to be!

intermittentfasting

Big Boy Tyson (L/M) is Gonna be a Challenge for (M)e ?

BadDragon, baddragongonewild

Measuring up for the challenge! Who’s gonna be the ultimate big clit slut? ??

bigclit, u_theeuroslut

This knot is going to be a challenge [ftm]

BadDragon

How Screwed Would You Be? (Kinky Caption Challenge Oct. 2020 #10)

Fantastical_Femdom, hentaicaptions

Merilyn Sakova could challenge Hitomi Tanaka for being the biggest natural girl...

boltedondicks

Should be choking on my cock while I drive with one hand in your pocket. Who’s up for this challenge? 22 M seeking subs. You know your place

gayslaves

it will be a tight fit, but i love a hard challenge!

adorableporn

She was intending to present it directly too you, but the blindfolds made that challenging. Don't be *too* hard on her.

OfferingHerLeash, Blindfolded

I can be a brat sometimes, can you handle the challenge? ?

DaughterTraining