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Two things about a CD are constant :- domination and sensation.
There are many other variables such as acceptance or humiliation, but domination and sensation are always the main focuses
Domination
When a CD is dressing, his mind state changes from a dominant to a submissive role. It doesn't matter how aggressive he is in normal life, he becomes submissive. This means that the dominatrix in the roleplay has to take the lead. She must constantly move into his personal body space in order to touch/caress/hold/look, etc.
Sensation
A CD is trying to experience sensations which are denied to him as a man :-
Fabrics :- Soft, silky, light/airy fabrics are a totally new experience. He will want to feel these against his body and of course against his genitals. He will also want to feel the constriction of underwear and/or the freedom of a skirt rather than the constriction of pants. Everything a woman takes for granted is a foreign and exciting sensation.
Combining domination and sensation
This is where the skill of the Dom comes into play. She needs to read the CD's responses and lead him down the path until his senses are overwhelmed. Some CDs are ashamed of their fetish and want to be humiliated. Others are wanting to experience a positive roleplay and need the Dom to be accepting and playful. Many CDs want to be encouraged or even "forced" to dress up. This removes the sense of responsibility from them and enforces their submissiveness. She should make suggestions and help with the process -- remember, the CD doesn't want to admit their fetish. Suggestions of clothing choices, holding clothes up to their body for decisions, etc will start the CDs mind game; and remember; it is all a mind game.
Once dressed, the Dom needs to determine the direction of the role play. Does the CD want make-up? Do they want to be humiliated? Do they want to do girl stuff (and remember that here we are talking fantasy girl stuff not real life)? Girl stuff would include walking in heels, modelling outfits, watching girl movies, etc -- think of the clichs and you'll be on track. Make suggestions and see what their mind wants to play.
Whatever activity is chosen, the Dom needs to always dominate (subtly or forcefully depending on the CD). She needs to always be in and out of the CD's personal body space. Touching, caressing and making the CD aware of the fabrics against their skin. Lifting their skirt to look at their cock and then touching, etc will drive the CD nuts.
Some play may involve pain and/or humiliation rather than soft touches and giggles, but it will always come back to Domination (keeping the CD submissive) and Sensations (fabrics/touching