Backstory:
[Alright, so last year around this time I got to be crushing on this amazing guy I'd known for a while- quiet, sweet, witty, tall, thin, pale, Cute, glasses, coder, artist, gamer, perfect for me.
We got to be better friends over the summer (as close as can be expected for two very introverted individuals really).
Come the beginning of the school-year, he trusted to me that which hurts him the most on a daily basis..
He helped me with calculus at the beginning of the year; I visited his house once a week and he came to mine once a week.
Then one day, after studying.. he pushed me back slowly and hugged me laying on the bed. I was stunned but said nothing and hugged back.
This slowly turned into hours-long hugging sessions (JUST hugging) and a neglect of calculus almost all together.
Then around october, he got a facebook; I learned of his other best friend (another girl who lives in california), and by december he was nearly completely avoiding me. In december too, a huge fight between him and his father went down which resulted in his leaving home to live with his grandmother. We didn't tutor most weeks, his depression over the events he trusted in me were crushing him, and his other best friend was about to enter basic training (when he vehemently opposes the military)
Since December he's been Substantially worse off emotionally..

(I should mention before I go any further that both I and his other friend confessed to liking him and asked him out at separate times and were both turned down because he didn't want to create conflict (among other reasons))

I slowly got him back into the habit of doing tutoring once a week unless it was impossible.. but tutoring no longer involved any calculus and it was never at my house. We just spent hours hugging.

And then one day.. he asked all blushing and shy and quiet and nervous if he could just poke my breast (through my shirt, not exposed).. he quickly interjected that of course I could refuse and he didn't really expect me to say yes.
I blushed beet red; I'd never been in a situation like this before (at 18, I know >.> shut up) and was quiet for some time before nodding.
poking slowly turned into pushing softly, pushing into grabbing, grabbing into squeezing and pushing together and resting his face in and rubbing his face against... into what happened most recently which is what has me so befuddled...]

/End Backstory

Problem:
He's stated more than once that he's uncomfortable with he idea of a relationship, mainly because he's uncomfortable with his own gender identity and has major self-confidence issues.. but a few days ago with the fondling of my breasts I'd grown to expect.. his thumb rubber over that more sensitive area at the front of the breasts, and I jumped slightly. he did it a few more times while doing his normal thing and eventually caught onto what he was doing.. when that happened, he started tugging at and squeezing those areas (again still through my shirt) and all the while I sat there blushing and thinking to myself "is this happening? why is this happening? if we can't be in a relationship.. if he can't kiss me then why is this ok?" interspersed of course with much blushing and squirming on my part.

He went quiet after a while because the whole thing actually wound up depressing him with his gender identity problems.. he got off me and I went over and hugged him tight and we were both very quiet for a long time.. then he wrote something that literally had me sobbing.. (what he wrote was meant to make me feel better but it kind of set something off) he held me tight and kissed my cheek (twice; the first times he's ever done this) and afterwards we talked..

He Thought he had induced Multiple orgasms from me.. (because of how I'd squirmed when he touched that area I guess, and it did feel good but.. not That good.. you know?)

what this shows me is that one of 2 things happened there and the first really leads to the second anyway:

• He was just playing, then thought I orgasmed 'the first time' and Kept going.
  or
• he was Deliberately trying to make me orgasm..

and that's not something just friends do. no matter how close they are.

Then I noticed his other friend was deleted from his facebook, and for the first time in MONTHS he switched his message settings to where I could see that he was online...

I'm beyond confused- (and embarrassed to have even posted this but I don't know where else to turn for some kind of advice) especially because part of me.. Really wants this to keep going.. part of me's willing to take whatever I could get regardless of if he thinks of me romantically or not.. another other part is pissed as all hell off.. because I haven't so much as had my first kiss yet and he knows this and he was trying to do that and somehow thinks that that is less embarrassing than a lips-to-lips kiss.. another part is hopeful.. because this seems like it Could be such a huge step towards a relationship with him (and this in fact is more relationship-like than any Actual relationship I've been in previously) and the last part is nervous.. because I'm sure he'll try to do this the next time I come over and I'm not sure I want him to if he can't say we're in a relationship or at the very least just kiss me.