So about three months ago one of my friends asked me to text her crush because she wouldn't respond. He responded to me almost immediately and said that he didn't really want to talk to her at that moment, because he was still getting over a relationship and she was being quite pushy. I apologized for her behavior(and later talked to her about it) and he thanked me. On most phones you have the option to have a signature, and on mine I have the new marching band theme for our high-school, and he commented on it. This was the start of our friendship. Apparently he too is in marching band, as a saxophone while I play vibes in the pit. I can't recall a single day since that night that we haven't talked. Sometimes, our conversations reach 100 - 200 texts a night. Usually he tells me goodnight, but instead of "Goodnight", he says "Goodnight, *insert my name here*", or "Goodnight, my little *insert my name here*". In the mornings I am usually greeted in a similar manner. One morning we were talking, and he brought up the subject of this freshman girl he likes, and I told him that I knew someone that was a freshman that liked him(me), so after a few hints I just told him. He dropped the subject and moved on, not saying that he liked me back or that he didn't like me. Now, lately(since I told him I liked him) he's been insisting that we have real conversations, since we usually just text(and if there was no such thing as unlimited texting, we'd both be screwed ^.^), and he's been making me feel really special, whether he means to or not. The other day he was upset because his grandmother was supposed to come with him to get his braces off(he only has a permit), but she made him late and the dentist refused to see him until next week. He's the kind of guy that just sulks for five minutes and shakes it off, but when he was upset he sent me a text along the lines of "You know, I'm ignoring everyone else. Everyone but you." I may just be hopeful, but I'm thinking this is a hint. And then the other day he told me that I owe him three hugs and a conversation, so I gave him a hug, and then the conversation was impossible seeing as we were at marching band. His response to this was "Well, then I may just have to sit with you on the band bus (;"(these bus rides are usually over an hour, and he knows I never fail to fall asleep on them). Which again, made me hopeful. Late last night he called me up and said that I needed to talk to him on the phone, right then, right there, because he was walking his dog and there was "less of a chance of him being raped if I'm talking to someone on the phone." Which I'm hoping is just a sad excuse to call me ^.^ We talked and joked for a while and then I ended up having to hang up due to babysitting. Anyways, earlier today I was texting him and he mentioned how much easier it was to talk face-to-face verses texting, so I brought up the fact that I love his voice, and his response was "No one's ever said that about my voice before but you. I don't understand...? But thank you

". And just now I asked him if my texting annoys him and he responded with: "No. If you didn't text me this much I would be far too bored. Usually by now I'd be annoyed, if it was anyone else. I don't normally like it when people text me non-stop like you, and I usually can't stand it when people ramble, but when you do it, it's cute." So I'm really hoping he likes me. People who don't know either of us very well have said he does, but of course I'm uncertain. Part of me wants to ask him, but the rest of me doesn't, in fear of that "No". I'm wanting opinions, should I ask him if he likes me? If so, when should I ask him? Should I let the relationship continue for longer before I ask? If so, how much longer should I wait?
Just wanted to add that my friend is 100% over him and knows I like him, and he is going to be a sophomore, I am going to be a freshman, and he is 727 days(three days short of two years) older than me.
Sorry it wasn't exactly... Short xD