I have the same problem with my keepall 50....it doesnt fit in the dust bag unless i fold it but I dont want creases. What Im currently doing (not permanent solution - I hope) is I stuff it with a pillow (standard queen bed pillow but for a speedy you'd want a throw pillow size) and then I put it in the dust bag as far as it will go with the flap on the top, so the bag is mostly inside the dust bag and the part that sticks out is covered on top by the flap. then I have the whole thing sitting in the giant LV shopping bag that it came in. And that sits on my floor beside my armoire. Not the best solution but for now it works.
The collapsable box I got with the keepall doesnt fit the keepall at all. in order to get the keepall inside that box I need to first fold it how LV does at the store to store them, THEN I need to fold the bag in half roughly where the handles are so that the two ends touch each other then stuff the thing inside the box....this scares the SH*T out of me and I bet this is going to ruin my bag in the long run....hence my alternative storage solution above.
I am hoping to get a cabinet that is actually from my grandmother and is an old lawyers file cabinet, its made of wood and have 4 individual sections that all have glass doors that swing up and slide in (almost like the doors on some TV armoires how they hinge open then you push them back into the cabinet - hope this makes sense) anyways when I move out of my mums house I want to have this cabinet resprayed and use it to display my LV bags behind glass so I dont have to worry about the dust bags. Alternatively I will invest in built ins in my walk in closet to store my LV pieces (and future LV pieces *wink* *wink*)!
For the speedy though I think you could ask your SA for a larger dust bag....a dust bag meant for the keepall should fit your speedy when its fully stuffed!!!
PS sorry for the long winded reply