I think you might be confused on the drain and fill plugs. Drain plug is obviously the lower one and the fill plug is on the side. After draining fluid, dropping pan, cleaning pan, then you install new filter and pan. You fill the tranny through the fill hole (on the side of pan), till fluid comes out. install plug, start car and warm up till the pan is warm (as per 632 Regals instructions). At this point you remove the fill plug and start filling again till fluid starts seeping out, then install fill plug and you're ready to go. Hope this helps out. There's a very detailed write-up on www.pelicanparts.com. Even though it's a different tranny it's got some good tips.
EDIT I might have misled you on the locations of the fill and drain plugs. I have the 4L30e tranny and the pan is alot different. Maybe 632 Regal can give you better specifics on the location of the plugs. I just went to www.realoem.com and looked up your tranny. It's definately alot different than mine.