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Probably we should start with the introduction of the two to the Guild,when Wiggly sees the human turned Jigglypuff,Rodrigo,and starts seeing the Jigglypuff as a little brother.
Then,we think on a way to get in trouble with Wiggly,so that he sadly decides discipline is needed(for added fun,your char could even think only I was in trouble,as Wiggly's new adoptive brother,only for Wiggly to say(after my spanking and conforting) that since you are my friend,he feels responsable for your behavior too...and as a result,you get spanked too! ^_^
Next we could do that Wiggly on machine thing,and then after this we find a way to get Wiggly in trouble with Rodrigo,accepting that it's only fair same rules applied to them both and ending up crying over his "little brother"'s lap. ^_^ How about it?
Yeah,role reversal is when someone who is usually the spankee becomes the spanker.
So,I figure I could be a Jigglypuff.And maybe,considering how friendly Wiggly usually is,the fact Rodrigo is a Jigglypuff is why he cares about our team enough to spank us,like,he could see the Jigglypuff as a sort of younger brother,and as Shinx is Rodrigo's partner,Wiggly decides to take care of him,too,lol.
This also is a good way to lead to the role reversal I mentioned-if Wiggly sees the Jigglypuff as a sort of little brother,he'd eventually go over Rodrigo's lap himself at somepoint on the rp- I believe Wigglytuff would be fair enough to accept the same punishment if he is naughty,after all. ^_^