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Requesting Pepper's Dare Compendium

Pepper

Well-known member
Joined
Feb 2, 2026
Location
Canada
Gender
Non-Binary
Pride
Nonbinary Nonbinary
This is a public place for anyone who wishes to train my poor little bum in creative fun ways! Or simply to torture my nipples or embarass me in other ways. I will give a full report, usually with pictures, of any dare I complete!

Here's an example of a report I wrote for Mr. H's plug gauntlet dare in which I had to work through every plug I owned and eventually wet my panties and stuff them inside me djskgnkgnsjsdkgn

I'm happy to discuss my tasks in pm's or in the chat if there are things I would like to be adjusted so it is more doable/fun for me.

Take a look at my toys! My cute pink training panties and also some pics of me are in my album too! My signature should have some other info :3

Here's some general idea of what I'm able to handle:
I have slept with my 2.25'' hush in before, and it was quite comfy. I have worn my 2.6'' glass plug for ~1h. I have worn my 2.7'' blue plug for ~15m. I have stuffed my entire one-piece swimsuit inside me once, for ~5m before I had to take it out and it was quite punishing! I have stuffed my bikini (top and bottoms) inside me 3 times, and kept it in for ~5m each time. I've been made to wet my panties before >.<. I've fit up to 3 pairs of panties inside me, but just 2 was incredibly filling. I've worn my meaner nipple clamps for ~30m before. I've tried to stuff my XS training panties in me before and failed... I haven't been made to wet in my pull-ups or training panties before but as punishment I'd be willing to try it. That's about it, excited to add to this list!
 
With how much you can handle I have an opposing idea. How hard can be something seemingly easy? I want you to wear your most loose plug while you are doing chores around your house. For example making meal, or cleaning something, as long as it require you moving around the house. If it slip out, put it in again. Count how many times it slipped out of your butt during your chores and let us know here. I'll prepare a dare based on how many times it happend.

Maybe some kenel exercises? Clenching could be helpful with keeping the plug in place. Good luck and have fun.
 
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Will do! I'll have this tiny 1'' kitty tail plug in while cooking in a bit :3 (no kitty tail attached tho cuz my roommate is home)
I doubt it'll fall out tho, my bum is pretty tight around most of my toys :p
Here it is next to my 2.6'' glass plug for reference
IMG_9447.jpg
 
I made some buldak instant noodles with a fried egg, mushroom, and some pepperoni! The plug didn't come out of course : P
my bum isn't loose dsnkgksggsdngkjs
 
In this case there's no need to clench it more, we need to go opposite way again - gaping!

You might have experience with it too, I don't know, I don't see it being listed, so start with reading about gaping. While you do so, go through each of your toys, from smallest to biggest. Either thrust with your hand or ride it if possible.

How much time you spend with each is up to you, but when you decide to change and feel you struggle with putting the new toy in, then you have to go back to the same toy for more time until you loosen enough to feel the difference. The thing is to read during this and end up with an article describing anal gaping technique, which you will follow with your biggest toy when you get there.
 
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