Obviously this gets a little tiresome because he always wants to take me to the edge. Do I have to keep doing this or should I just ignore him back and await a response?
If I'm honest I kind of don't my asking again but I am cautious about it incase he's just pushing boundaries and then it will escalate further!
Is this a boundary that you have established for yourself? If so, I would not re-text him. He will learn quickly that he needs to respond the first time if not, he's going to miss out hanging out with awesome you.
However, you state that you don't mind doing it. If this is the case and it really doesn't bother you at all, then save the boundary battle for something that is more important to you. You have to determine how important this issue is to you. Whatever your decision is, be consistent and stick to it.
Boy, I hope I don't get my account deactivated for giving terrible advice

Good luck.