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I'm on Wind pay before so I can answer this for you. You have an account with Wind. At any time you can add funds to your account. Each month Wind deducts the cost of your plan from your account balance, and you need to make sure you have enough or your service will be cut off. I believe certain pay-per-use features like roaming are charged at the time of use.

With post-paid you are given a bill at the end of each month which you must pay, which will include any pay-per-use costs. There is no difference in cost to you.

When you sign up for your pre-paid service you will be immediately charged a pro-rated amount for the remainder of your month. From then on it is up to you to keep enough balance in your account to keep your service active. The top-up cards from Shoppers Drug Mart and others are one way of adding to your account balance; I usually add directly via credit card from their website.
 
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