Honestly, there's nothing wrong with men wanting to dress like women. People say it's unnatural, but we're the ones who created the idea of men and women dressing separate. How is man-made natural? I HATE gender roles. People should be able to do whatever they want, regardless of genitalia.
Anyway, to look girly, one really easy step it to soften your facial features. Thin your eyebrows, and get hair that frames your face. Also, wear light makeup. Too much runs the risk of you looking like a drag queen. try a matte foundation, no eyeshadow. instead, take a contrasting eyeliner [purple for brown eyes, copper for green eyes, or brown for blue eyes], and smudge around the top and bottom of your eyelid, like this. http://www.naturalook.com/blog/wp-content/uploads/image/Single%20Eye%20Erica.JPG . It makes the eyes pop, without looking like too much.
For lips, a lip tint will do better than a lip stick. Again, its natural and pretty. For olive skin, try mauve, for fair skin, you can do almost anything, for peach skin, try a golden pink. http://bellabeauty.files.wordpress.com/2007/09/ambervalletta.jpg
For clothes, i'd need to know more about your body type to help you with what style to wear. You say you're skinny, so your options are almost limitless, but to get a really personal suggestion, i'd have to know more.