Just kiss him at the end of your next date! You don't even need to wait for a date though, just kiss him whenever you next feel that insane sexual tension and rather than waiting, just go for it. I assure you he'll find that super hot, plus why shouldn't the girl initiate? Boys usually make it quite obvious when they're no longer interested, so you most likely don't need to worry about that.
I'd say just go for it. You really don't have much to lose in trying, and I'd rather have tried and it not worked out the way I wished than chickening out and always regretting it/wondering 'what if'.
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You clearly like him. I think he doesn't dare to kiss you cause you tend to get nervous. Loosen up! Do not chicken out! Just kiss him, he will kiss back. And there is no reason to be afraid of sex either. He seems like a nice caring and patient guy. If you feel like fucking, just fuck. He won't complain, although he might if you don't give him anything for much longer (giving is not really the right word as it's for the both of you to enjoy). Anyhow, I think you are the one that needs to make the next move.
End of senior year, only been kissed twice.
Be patient or make a move yourself! Honestly what's the worst that could happen.
Talk to him about it. I know i have very low self esteem. When i was young and starting to date I assumed a woman does not want any physical contact unless she initiates it. I didn't go on many dates before i got married. Now after 25 years i went through an unwanted divorce and i will be back in the much hated dating pool eventually. I dread the thought and just want to get past it and to the relationship stage as quickly as possible.
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