[Geo T]

Hum... I hope I get this right: you want creative dares losely based on your keywords right?
If so, here you go.

Since you want to train your rear slut hole, here is what I demand from you:
1 -ENEMA: you'll need to be clean for the rest: take it at your current quantity. Get on all four and rock back on forth for as long as you can before release. Take your smallest plug in your mouth and don't hesitate to drool,
2 -PLUGs: line them up, smallest to biggest. You will lube them with your mouth which you started in 1. Then, fuck your ass 15 times at the rythm of 1 stroke, in and out, per second. Then take the second biggest one that you'd place into your mouth or licked, drooled over as I doubt you can place the biggest one between your slutty jaws.
3 -STUFF: once done, try to stuff your ass with as many panties as you can. Let's see if you make some progress with this training session. >xD