Tinkerbell - Hi! You experiment with wearing female clothing. It feels good. You experiment some more. It feels better. Probably to a great extent it is just normal human behavior.
People behave the way they do because their behavior brings a reward. The reward can be almost anything - getting away with being 'naughty', feeling physically or mentally good, enjoying looking feminine - endless possibilities. The tendency is of course to repeat behavior than brings a reward -and that behavior will persist until either the reward disappears, or the disadvantages outweigh the perceived benefits.