First and foremost, there's Kyoko Matsushita. She mostly wears swimsuits and pantyhose, and she is absolutely gorgeous. She manages to look like a real woman every time. Her body is slim and curvaceous, and her pictures tickle my swimsuit fetish. She also wears all kinds of form-fitting dresses and lingerie.
Amazingly, she does this in secret. She lives as a man the vast majority of the time.
This makes me fantasize about how practice makes perfect: she's worn girl stuff so many times, and so many different outfits (surely hundreds!) that she practically looks like a woman now. I love the idea that wearing women's clothes will gradually turn a man into a woman. He may think it's harmless at first, that it's OK to get a thrill from it now and then, but that every time he does it, it makes him that much more feminine, until he starts looking like Kyoko Matsushita, and can no longer hide how feminine he's become.