When You Are Both Getting Ready To Go Out For The Night, Tell Her That You Would Find It Really Sexy

When you are both getting ready to go out for the night, tell her that you would find it really sexy if she went without underwear this time. When you get back home, continue to tell her how hot it was that she wasn’t wearing anything under her dress the whole night. The positive reinforcement will, over time, teach her to never wear underwear with a dress or skirt again.