Jizz

I bet she feels just a little bit cheated.

BreastEnvy

Truth Or Dare Bet [Cheating] [Bet] [GIF]

xxxcaptions, CheatingCaptions, cuckquean, PornFinder, u_dude_1911

Oh there's absolutely no way you could get her to do that, I'd go double or nothing that you don't have a chance in getting my girlfriend naked. [Bet] [Cheating-esque]

xxxcaptions, NaughtyFunthings

I lost a bet with my friend, but my girlfriend doesn't seem to care [Gf/Friend/Cheating]

xxxcaptions, CheatingCaptions, BrotherCucker, u_fucmywhitegf

you totally cheated on the tests, but it was worth it. [Lost bet] [Blowjob] [Look at dem eyes tho]

xxxcaptions

She hated how you insisted on taking pictures too. [Cheating][Lost bet]

xxxcaptions, u_dude_1911

Lost that bet [cheating]

xxxcaptions

You really thought she'd chicken out... [lost bet] [MF] [cheating]

xxxcaptions, u_dude_1911

Pool Bet [Bet] [Cheating]

xxxcaptions

Who would you bet on?

xxxcaptions, Not_Cheating

The girls were the betting type. [naked] [group] [implied threesome] [implied cheating with permission, I have no idea what to call that]

VanillaCaptions, u_pitchardg

Sexy ass Renee almost made me cheat on my bitch! Thank god I didnt do it! I been with my bitch for 3 years and she almost came through and fucked up a happy home! Man I would be feeling stupid right now! But i bet those titties would have tasted good thou

RuthlessHoes, aa_cups, Bigtitssmalltits, CollegeAmateurs, collegesluts, cuckoldcaptions, knockmeup, xsmallgirls, TinyTits, Titties

Unfair Bet

Not_Cheating

A bet's a bet.

Not_Cheating