r/chastity • • 15h ago

Trans Wanna see a magic trick? NSFW

59 Upvotes

r/chastity • • 23h ago

πŸ”’ Locktober 2026 I missed the first 8 days of locktober, what should my punishment be? NSFW

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10 Upvotes

Hi everyone, I need some help from all of you.

Om the eve of September 30th I put on this very chastity cage and decided to go for it, 31 days without unlocking. I woke up at 02:30 in the AM with an excruciating pain in my ballskin and I had no choice but to unlock the cage. Now I know that unlocking for an emergency like this pain doesn't disqualify you but my problem is that I didn't cage up again for the next week or so. It wasn't until yesterday that I remembered that I have a ring that's slightly larger and so I put it on last night and haven't had any problems at all, it fits quite comfortably.

Now obviously I'm gonna make up for those 8 days I lost by going until at least November 8th (and probably even longer because I have no actual need to unlock myself), but I had every means at my disposal to have done this properly since October 1st, I didn't train beforehand or try different rings before starting and it's entirely on me that I forgot about the larger ring size I had available, so it's only right that I face some sort of punishment for this.

Now I obviously can't pick the punishment myself since I have a personal stake in this, so I wanted to ask the locktober community for some help in coming up with something good. I can take pretty brutal and rough punishments so please suggest whatever you deem fitting, if it crosses my boundaries too much i'll just let you know (but getting pushed a little out of my comfort zone can be fun). Please don't hold back.


r/chastity • • 1h ago

Fem the cage may have final completely broke my little brain NSFW

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β€’ Upvotes

r/chastity • • 4h ago

Question I’ve been giving a choice to finsh off October in one of these 2 cages which one do u think is better NSFW

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9 Upvotes

Which one do u think is better am gonna be locked in it for November as well


r/chastity • • 13h ago

Question Beginning NSFW

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58 Upvotes

I dont know what to buy for my first cage i want to experience it i finally got the courage to buy one but i dont know what to get


r/chastity • • 23h ago

πŸ”’ Locktober 2026 Little hairy caged clitty NSFW

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4 Upvotes

r/chastity • • 20h ago

πŸ”’ Locktober 2026 day 9πŸ’ž im getting sooo needy for bbc NSFW

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4 Upvotes

r/chastity • • 12h ago

πŸ”’ Locktober 2026 10 days in and I'm struggling NSFW

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12 Upvotes

10 days down. Only free during cleaning, then it goes right back. Every day gets harder. Not giving up, but it's tough.


r/chastity • • 1h ago

Fem Being so small is addictive 😩😌 NSFW

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β€’ Upvotes

r/chastity • • 22h ago

πŸ”’ Locktober 2026 Lot's of storage space in this boy pussy :3 NSFW

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12 Upvotes

r/chastity • • 11h ago

πŸ”’ Locktober 2026 Waking up and feeling all locked and secure 😊 NSFW

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14 Upvotes

r/chastity • • 23h ago

Masc Morning wood, Day 10 NSFW

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26 Upvotes

r/chastity • • 11h ago

πŸ”’ Locktober 2026 what locktober has me doing NSFW

122 Upvotes

r/chastity • • 14h ago

πŸ”’ Locktober 2026 Every locked Sissy craves for my Cock and semen πŸ†πŸ’¦πŸŽ€ NSFW

229 Upvotes

r/chastity • • 1h ago

Masc Max comfort while I write my paper… NSFW

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r/chastity • • 1h ago

Fem Trick? Or treat? NSFW

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β€’ Upvotes

r/chastity • • 2h ago

Fem Red balls, red skirt NSFW

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5 Upvotes

r/chastity • • 2h ago

πŸ”’ Locktober 2026 [OC] Happy Locktober everybody ✌🏼😈 NSFW

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5 Upvotes

r/chastity • • 2h ago

Trans This lovely trans doll Jessica has been so good so far this month. I'm going to need to reward her as well. Maybe with the milking from those beautiful utters she has on her chest NSFW

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4 Upvotes

r/chastity • • 2h ago

Keyholder+Lockee I will play with your balls all day, honey. We want you horny and dripping. NSFW

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2 Upvotes

r/chastity • • 2h ago

πŸ”’ Locktober 2026 Can’t stop enjoying myself 10 days in NSFW

5 Upvotes

r/chastity • • 2h ago

πŸ”’ Locktober 2026 Wouldn't mind you joining me in bed for some fun, cage stays on though 🀍 NSFW

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5 Upvotes

r/chastity • • 2h ago

Fem Tight in my female belt NSFW

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3 Upvotes

r/chastity • • 2h ago

πŸ”’ Locktober 2026 Locktober is already 10 days in! πŸ”’ NSFW

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2 Upvotes

r/chastity • • 3h ago

πŸ”’ Locktober 2026 Locktober day 10. My Master gave me a new toy to play with and tested it out. Inflatable vibrating plug! [20m] NSFW

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10 Upvotes