Create a Snakes and Ladders Game for Me!
 

Was looking at some snakes and ladders games and thought it'd be fun to make a snakes and ladders game with the help of getdare! My primary goal is to train my asshole to more comfortably use my 2.25'' and 2.36'' buttplugs, but I'm happy with some tasks with my nipple clamps or panties as well.

I am able to work them (the 2.25'' and 2.36'' ones) in me, with some difficulty in a few minutes, and I usually cannot endure pushing them in and out of me more than 15 or so times in a row. I can wear them for a few hours but it is rather uncomfortable as they are so big and filling. I can wear my 2'' plug for much longer and can push it in/out much more easily.

Here are the toys I own: Buttplugs of sizes: 1.75'', 2'', 2.25'', 2.36'', 2.6'' (I cannot fit the 2.6'' one :( so please don't use this one)
Clover clamps with 2 attachable 220g weights (I have a hard time wearing the weights for longer than a few minutes so please don't be mean).
And I can fit up to 3 panties up my butt (1 is uncomfortable, 2 is very uncomfortable, 3 takes a lottt of effort and leaves my butt hurt and roughed up enough I won't do anything for the rest of the day)
I will use lube to make things possible, and toothpaste if specified.

How this will work is I will start at the very first post/task/square - complete the task written on the post, then roll a 6 sided dice and move that many squares (tasks) forward and repeat until I complete the task on the 100th square! Please write your tasks with spoilers.

For example, if the person before posted something like

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You would start your post as 8: followed by a spoiler and the task!

It's entirely up to you how hard you want to make this for me! Some devious things you can add are the usual snakes and ladders "go back X spaces," "go to space X" things, but also many other ideas like "reduce your next X rolls by Y," or rules that last for the remainder of the game like "add weights whenever you wear nipple clamps for the first 5 minutes!"

The great part is you can also be nice to me and let me do things like pick my next few rolls or skip forwards or pick a rule to ignore! Or you can be as mean as making me go back to the very first square! I should have a very different experience each time through depending on whose tasks I land on and in what order! I will play through until I reach square 100 3 times, and add the oppurtunity for you to make me play it again through PM dares (maybe if I have 3 votes for it in a week or some other condition as I expect it to be quite time consuming!).

Some rules:
If there are any tasks I cannot do because they break a limit of mine or are simply unfeasible/ridiculous/uninteresting I will do my best to discuss for an alternative! If I still cannot I will treat it as "move back 1d6 squares." If I "go past" square 100 I will simply go to square 100 and complete the game. To prevent infinite loops and to make things a bit easier on me, I have the option of wearing nipple clamps for a minimum of 15 minutes on any non-nipple clamp square and I will be allowed to skip it during future repeat encounters. I won't know if that is likely or not though, so it'll be fun to try and decide if I should just be wearing clamps for everything! For tasks where I already must be wearing nipple clamps, I can add additional weights for 5 minutes to achieve the same future immunity.

Please no repeat posts.

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This sounds like a great game my little slut!

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As an idea inspired by Leland, when 25 squares have been filled out, I will play this game once with 25 being the end square. I will do the same once at 50, and once at 75! I'll write a detailed report so that you all have a better idea of how the game might play out.

I've been a bit busy with moving for the new school year and might also be travelling to meet up with friends at a different uni before classes start in this next week, so might not be able to play right away, but I will ASAP after 25 squares have been filled out!

Also as suggested by Leland, so that every post has a square attached,

13:

I also think with these changes it could be fun for squares 25, 50, 75, and 100 to be a little special as the final task I complete before finishing the game. Not quite sure on what to do for them, but I welcome any suggestions! I do want to do something fun with "unlucky 13" or other "special" numbers.

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