my boyfriend wants me to deep throat and gag??

So like my boyfriend enjoys bj's, just as much as I enjoy giving them, however lately I've been self conscious about giving them because my bf always asks to go deeper and I JUST CANT. he always says "take the whole thing.. all the way" and I can't, it won't go that far unless I gag. And I tell him "no it's going to make me gag" and he says "that's okay" WTF does that mean?? I'm not going to gag and seem weak (mind you, my face while gagging isn't like a porn star, motherfucker better watch out for that vomit on his d 😂) So I don't understand why he wants me to go all the way? And why he wants to make me gag and watch me? 
Any tips on how I can go all the way and deep throat without gagging?