Have you contemplated the idea of forced feminization via hypnosis? If not then let me tell you a little about what you can do. You can use hypnotic transsexualizing to make your man feel like a girl and want to be a girl more that anything else. This can be done easily if the man being hypnotized is heterosexual. Once hypnotized these men quickly become extremely desperate to have breasts and a vagina.
In order for this process to be successful you will need to find out everything that turns your man on and have him describe to you re his dream girl. During hypnosis his desire to be this dream woman is increased to the point of obsession. He will become jealous of women who have these attributes and to believe that it is unfair that women have them. He will begin to believe how wonderful it would be to have a body like this and he will begin to hallucinate about what it is like to become this dream girl.