Most Helpful Guy
It sounds like he is insecure. Ask him what need he haves to be asking something you truly feel for him.
Most Helpful Girl
Have you asked him why? He might just like hearing it so if his way of getting you to say it by asking is bothering you maybe just tell him to say, 'tell me you love me' when he needs to hear it.
Do you do things for him like lots of hugs, massages, cook stuff he likes? Some men need a lot of attention/ affection, a lot of men actually.
Now if he is still asking while you're sleeping with your nose buried in his armpit I don't know what to say. LOL