I need encouragement

Hiii I'm Jo, bisexual transmasc. One year ago I met a boy in my drama class, very gay. He and I grew close together and he was kinda flirty for a little bit I dismissed it. The day he gave me his sweater and said it looks better on me,  I realized I liked I'm. Since then, our friendship's boundaries have been pushed. We've gone from small touches and hands around shoulder to sittinng in each others lap. I specifically remember one dayy on the way back from a field trip late at night, we fell asleep cuddling eachother.  It's happened more, we've gotten more touchy and cuddly, he lays on my chest and lets me rub his, and recently we had an intimate moment backstage. The lights were low and we were close, there was a pull, he felt it too, but we were interrupted. Since then, its been more of "I love Jo" and "I see Jo everywhere I go" and I want to officially ask him out (despite the fact that we kinda already went on one unestablished date). My issue comes in that I've never asked anyone out before and the one time I did, I got rejected. I'm afraid of sayingg something wrong and ruining our friendship, which I still deeply value. I need some encouragement and advice