Of course your new Sissy might be apprehensive at first so you stroke his little clit as you push your toy into his sissy pussy! When he cums you must do two things, you must make him lick your hand clean and you absolutely must leave the vibrator in place!!!
Soon you'll use only the vibrator to make him cum...after a little training the stroking will become unnecessary!
Sissy will be happy and it will be another step down the road to becoming the sissy you want him to be!!!