This can probably be done and it’s easier to think of building blocks versus baking. I’m not sure if you want a tower, as in, it will get smaller as it gets to the top, like a pyramid; or a straight-vertical edged stacked experience, but I’d lean you toward the first option, as it will be far more stable. (Cupcakes in paper liners are wobbly at best. Silicon liners or the kind of dessert cup liners that Chockylit uses might give you more stability.)

The pyramid option would also allow the most chocolate to hit each cupcake. (The first thing that came to my mind when I read this was that if you were to stack un-iced cupcakes and drizzle something over the top, the bottom layers and inner layers would get hit with little-to-no topping.) It would be fairly easy to assemble on a cake plate and just build a pyramid, making sure each cupcake rests centered over the crack between two below, for the most stability.

If you really, really don’t want a pyramid (and, oh, what a cute cupcake you could put on top for bride and groom!) you might want to look into some stands, such as a couple of these or one of these or these.