I have a couple so times with my husband while we were still dating, usually had on either a dress or skirt that fell below the knees. The fun of it for me was telling him about it, drove him nuts. I wouldn't do it under a short skirt, I only do it for him to see or better yet drive him nuts when he finds out about it. I think the longer skirt works better, he can't get a hand up it like he could a short one so its all in his mind! = }
Once while wearing a skirt I excused myself to the ladies room, then discretely slipped my thong into his back pocket when he stood to push in my chair. He knew what I slipped in his pocket, he wanted to hurry home for desert! I think that had a bigger effect on him than just telling him I had no panties on under my skirt. He loves a surprise!!!
Never. Not that I ever really wear skirts, but in the summer I'm a huge fan of really short dresses. I always make a point of wearing not only some thongs, but also some spandies/booty shorts just in case the wind picks up. :P
No never gone commando. If you have to keep pulling it down, then its two short also bend over as far as you can in a mirror. If anything that shouldn't be showing is showing, then it's too short. No, I have never intentionally flashed anything.