There are as many types of sissies as there are women who keep them. And you don’t need to move him right into it. Many women ‘migrate’ their sissies from Tom Boys into Temptresses over a long period. Give lots of thought to the look you desire as reshaping at a later date will undoubtedly confuse the poor dear.
Tip: Let him participate in his transformation in little ways to give him a feeling that his opinions are important—sort of. If you decide you would like a ‘nice girl’ look, let him pick out the hair color and styling that would be appropriate.