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it'd be a challenge for most pussys

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Standing Up to the Challenge.

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Who doesn't like a challenge.

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it was more of a challenge than i thought it would be...

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I Accept Your Anal Challenge

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[Challenge] Cum on girls I know. Bonus points if you write dirty stuff on their forehead like "anal whore, cumslut, etc."

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Who doesn't like a challenge.

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

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Anal speed test challenge

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Chinese typewriters and the challenging pains of hot-water piping

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Fuck you, we go 2on2 Kira Thorn & Anna Rey anal challenge with No Pussy / Balls Deep DAP / Gapes / Cumswapping / Swallow GIO505

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Giving herself a challenge

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Challenging Juri [Street Fighter] (Mizaru)

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Please cum in my ass! [Anal] [JOI] (This was a challenge with /u/PornMaker2048, he provided the caption, I did the image)

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[Ella Reese, 23] "I'll start doing anal scenes once I get to 100K...ya'll can hold me to it". Challenge accepted Ella. Challenge accepted...

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[F] Kept my dilating plug in all day at school, it was a challenge but I’ve been so horny

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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]

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Asshole challenge!

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After the warm-up comes the real challenge... [implied anal] [cum]

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Challenge accepted. [blowjob] [implied anal]

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Chubby UK Milf Anna Joy’s Cum Challenge – Can You Cum Twice?

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Make the Sharpie Challenge relevant again

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Fishnet Anal Challenge

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Day 8/? o[f] my August anal sharpie challenge! How far can I get? [OC]

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Day 8/? of my August anal sharpie challenge! How far can I get? [OC]

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Fishnet Anal Challenge

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Fishnet Anal Challenge

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Fishnet Anal Challenge

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

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Rosa - taking on Hilda's Challenge and sitting on a large anal toy (Greenopi) [Pokemon]

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