In my experiences there are three catagories on this topic:
1. Feminisation as a way to humiliate the strong male, who gets a kick out of not having any control. This can be a simple as making you wear ladies panties and or stockings under your clothes, only we know about it. Or I could dress you fully in an outfit of my choosing from the womens clothes and shoes I have to mock how rediculose you look or objectifiy how good you look – depends on the guy, which is a step up from the embarassment to making you feel full on humiliated about the whole experience … of course this may well get mixed with other activities too.
2. Sissyfication or cross dressing, this is the other end of the scale. You want to be dressed in frilly lacy items as the experience of feeling feminine is freeing for you. The girlier the better, with make up, hair and perfume. Some like to be dollies, some slutty, others like to be classy. But you all become my plaything. And again could be mixed in with chastity or strap on play too.
3. Grender identity, and this one is very different. You may have to live day to day as male but secretly you long to become female permenantly, or family life may mean you can’t share your desire. This type of session means you can come hand out with me as the person you feel you really are. I can transform you and we can then go be social in public if that is what you crave.
However it works for you, I have 16+yrs of working with trans individuals and cross dressers – and 9+ of those have included my kink years. Which means I can offer very detailed insights now from pre surgery hair removal, to how to pass, to how to walk, to how to tuck, how to make a real clevage, to just being an ear to listen, or teaching you how to cum like a woman … and more besides.