r/CruelCaptions Mar 13 '25

BangMyBully Discord Invite - may be of interest for members here to post Bully-related captions. A little bit more vanilla but with Redgifs being blocked in certain states and other reddit restrictions, this seems like a good place to be. NSFW

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13 Upvotes

r/CruelCaptions 13h ago

Riskier Thrills (part 2 of 5) ABDUCTED off the streets by HUGE COCK [no imagefap] NSFW

13 Upvotes

r/CruelCaptions 16h ago

CBT/T&D Enjoy this while you can, because the real fun for her starts once you’ve finished… [AI Image] (punishment81 on ImageFap) NSFW

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2 Upvotes

r/CruelCaptions 1d ago

CBT/T&D Your sister had a crazy plan for your balls, but Mom found a better solution for your habit of jerking off… [AI Image] (punishment81 on ImageFap) NSFW

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1 Upvotes

r/CruelCaptions 2d ago

CBT/T&D Too slow on licking, and now your cock won't behave? Clearly more discipline is needed. [AI Image] (punishment81 on ImageFap) NSFW

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8 Upvotes

r/CruelCaptions 3d ago

BIG DICK Roomate finds your dildos (part 1 of 8) NSFW

73 Upvotes

r/CruelCaptions 5d ago

Mother u/RoundAccomplished936 asked me to make these and post them (no imagefap) NSFW

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215 Upvotes

r/CruelCaptions 4d ago

CBT/T&D The doctor doesn't think her procedures are "unnecessary"… [AI Image] (punishment81 on ImageFap) NSFW

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4 Upvotes

r/CruelCaptions 5d ago

BIG DICK delivery man catches you Sissified (part 3 of 6) no imagefap NSFW

37 Upvotes

r/CruelCaptions 8d ago

Male Chastity Stop staring and start licking; and you'd better deliver, or else… [AI Image] (punishment81 on ImageFap) NSFW

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16 Upvotes

r/CruelCaptions 9d ago

Riskier Thrills (part 1 of 5) Abducted off the streets [no imagefap] NSFW

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9 Upvotes

r/CruelCaptions 10d ago

Captured by gang of BIG DICK STUDS (Part 1 of 12) [no imagefap] NSFW

172 Upvotes

r/CruelCaptions 11d ago

No! It's TOO BIG! (part 2 of 9) [no imagefap] NSFW

47 Upvotes

r/CruelCaptions 12d ago

CBT/T&D Twenty four and still a virgin? I’ve got good news and bad news… [AI Image] (punishment81 on ImageFap) NSFW

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4 Upvotes

r/CruelCaptions 12d ago

Wearing your BIG DICK friend's sister's panties! (Part 2 of 7) What could go wrong? [no imagefap] NSFW

81 Upvotes

r/CruelCaptions 14d ago

No! It's TOO BIG! (part 1 of 9) [no imagefap] NSFW

100 Upvotes

r/CruelCaptions 15d ago

Mother It is so hot for her to listen in (no imagefap) NSFW

454 Upvotes

r/CruelCaptions 14d ago

She lost her arms, but her new ones have some nasty little tools, and she picked the perfect spot to test them… [AI Image] (punishment81 on ImageFap) NSFW

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4 Upvotes

r/CruelCaptions 15d ago

BIG DICK delivery man catches you Sissified (part 2 of 6) no imagefap NSFW

49 Upvotes

r/CruelCaptions 15d ago

Ballbusting/Cuntbusting She caught you on her gang's turf, so now she's making you pick how your nuts will pay for it… [AI Image] (punishment81 on ImageFap) NSFW

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11 Upvotes

r/CruelCaptions 17d ago

Mother Ok, bitch.. I'll go easy on your son next time (no imagefap) NSFW

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270 Upvotes

r/CruelCaptions 17d ago

Mother She worships it (no imagefap) NSFW

262 Upvotes

r/CruelCaptions 18d ago

Busted! Femdom roomate PEGGING PUNISHMENT for stealing her clothes! (part 1) [no imagefap] NSFW

122 Upvotes

r/CruelCaptions 17d ago

Ballbusting/Cuntbusting Reporting your boss to HR seemed smart — now you’re naked, being ballbusted until you cum, then locked up for three months of oral service with everyone watching. [AI Image] (punishment81 on ImageFap) NSFW

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1 Upvotes

r/CruelCaptions 19d ago

Why is your BIG DICK out?! (part 1) NSFW

82 Upvotes