If you have direct market access you can match particular orders in the order book, even if they are out of the money. Your friend would fill your $0.01 order at $0.01 and move the last trade price.
Also, except in the case of certain rare events which cause high latency (e.g., yesterday), it is also illegal to play games like this. For instance, if the bid is 99 on BATS and only 50 on ARCA, and I want to sell, I can't sell on ARCA. (I'm grossly oversimplifying, of course, but my simplifications don't exclude the case of selling at $0.01 to fool the markets.)
If the market is 99.99-100.00 you cannot trade even at 99.98