Wow Max1328 that is a hell of a dare, I'll try to get inspiration from it. The obvious best implement for some good anal stretching is the inflatable plug but you don't list what it's smallest size is so I don't know how possible it is to wear for an extended period of time. Assuming that the inflatable plug is, at its smallest, in the 4.1 to 5.1cm range hopefully the following dare works for you. If not, you can substitute the inflatable plug for a selection of your other plugs as you see fit. I've found a similar looking inflatable plug and it's minimum diameter is 3.1cm, so there is some research to my assumption.
Cleaning is an important part of having an apartment, doing dishes, vacuuming, putting away clothes, or washing used anal toys. A few times a week, you are going to pretend that you are a cute little maid cleaning your master's house. If possible, dress up like a slutty French maid or as close to it as you can. Of course as a slutty maid, one of the most important parts of your uniform is your plug. After getting your maid uniform on, you will insert your inflatable plug, give yourself a good spank on each of your ass cheeks to get them rosy, and pinch your nipples to try making them more prominent. You will then start cleaning with the pump from the inflatable plug hanging from you like a proper anal whore's tail. As you clean, you will routinely inflate the plug whenever your mind wanders away from your duties as a maid. When you inflate the plug you will imagine that it's your Sir squeezing the pump. He has been sitting nearby, working while you clean and has noticed you're slacking. Walking up to you, he squeezes the pump, he knows the only way to get a buttslut's attention is through her ass. Of course Sir also likes to pump the plug up sometimes just for the fun of it, as he walks through the room, the sight of the pump dangling from your ass is just too good an opportunity to pass up.
You will clean until your Master's house is clean. If you reach your limit you will keep track of all the pumps that you would have done but didn't, the next time you clean you will start by adding those pumps back in. If you cannot train yourself to either keep better attention or, more likely, to take more pumps, you will accumulate a backlog of pumps. This will result in you spending the entirety of your cleaning task at maximum inflation which will surely speed up training.
Let me know if any modifications need to be made. I hope you enjoy the dare and that it serves it's purpose. As a side note, if you would like a task that involves cleaning out your ass with an enema, let me know. Enema's are a kink of mine, but you said you hate them, but then also don't list them in your dislikes or limits so I have no idea if they are fair game. I assume that you only use them for cleaning yourself before anal but you do include it in your toy list so I don't know. Maybe you do them frequently regardless and would like to find a way to make them at least a little more fun? Let me know.
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