There is an old gag that runs, if you toss a frog into boiling water it will get out, but if you put the frog into the water and slowly turn up the heat, it will not notice and let itself be cooked. (I in no way endorse trying this with frogs. Use real people, much harder to get attached to than frogs.) The point being you gradually move it rather than deluge it.
I would have gone shopping, but only bought one thing, and I sure would not have laid out the entire wardrobe (in the beginning, before you start going out and really thinking about it in that context of being public the 'entire wardrobe' deal has stuff in it that screams 'FETISH") for her to see either.
Once I'm telling someone about it, talking to them about it, my next step is to dress up and meet them someplace casual in very casual clothes, like going out for coffee or something like that. Little by little, bit by bit.
And what kind of group session? That one seems real weird.