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The bottom line is for me basic assumptions get screwed up, I start looking for previous experiences to use as points of reference and boundaries, then I get scared of doing something wrong, and retreat. I don't know if that makes any sense.

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It does to me. It's *really* hard to start letting yourself feel dependent, and even harder to show it to someone else (like your T), when you're not used to acting that way and have all sorts of assumptions about it being a not good thing (and assumptions about what your T will think of you for acting that way). As my T always tells me, you're brave to try new things. Good luck!