Evening gown, lowcut v with a high cut slit up the side. You would be able move the v so that the breasts would pop out, and the slit down the side would gain you entrance to DATY.
On the conservative side, English professor with glasses. On the timid yet curious side, and Japanese school girl outfit...short skirt of course. Cleavage no matter what the outcome fit. Damn...now you have erected the force fully, young jedi in training!