Placing orders for delivery on multiple days

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Im am currently trying to set up a webshop for my Bakery.

Right now orders are placed by telephone, written down manually and then typed into a cash register.

I'm now trying to set up a shop, where customers can order whatever they want to have delivered online, an then select when they want to have it delivered. 

This in itself isn't very hard to do. I have however not yet found a way to enable customers to have the same order delivered on multiple days.

Most of my customers have the same order for a whole week, or the same every Monday and Friday etc. 

Is there any way to enable buyers to select - ideally in a calendar window - the days they want to have their baked goods delivered, or maybe even keep getting them delivered until cancelled?

And how would Payment for something like this work, considering the order basically goes on indefinitly? 

Any help at all will be greatly appreciated!