I cannot recommend anything, cause I am too inexperienced in this matter. But I enjoy reading about your life and feelings and can for sure understand your feelings regarding being collared. Hope someone comes up with something.
Buy a mid ranged skirt and wear together with a tight top. No underwear. Go for a walk, visit cafés, normal stuff. Then buy a shorter one and do the same. See how short you can go. (I know you are a male ;))