Honestly, for men, having to pull out is no fun at all. He may tell you that he's OK with it, but I promise you that he would rather not. Have you considered another method of birth control? All most all methods are more reliable than pulling out. I would suggest condoms....
I would start off by talking to him about it. Ask him to be honest about how he feels about pulling out....It sounds like he wants to make you happy.
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