Bringing him out of his comfort zone is part of finding himself take him to find himself but learn a skill that is useful to you as a female dominant aswell +++
(51) I have made many mistakes with my sub but one of my successes was sending him to beauty school to learn how to do my nails. I love this service that he now provides. When I told him about beauty school, he argued that he wanted to learn from me but I suspected correctly that he felt embarrassment about being the only middle aged male at the school. He rarely tried to deny me anything so I didn’t often have a reason to be displeased with him. However, I knew I shouldn’t miss the chance to put him in his place. I was secretly amused but I pretended to be offended by his reluctance and allowed myself to wind up into a tempest of a snit. I told him that he would attend and as punishment I would dress him for his first day! I have never been interested in feminizing Butler but the morning of his class I put him in black stretch skinny jeans and a lacy blouse I purchased especially for that moment. He looked about as gay as a man can look. He’s not homophobic but I will never forget his stunned and slightly mortified look as he put on his new clothes. No one would suspect him of being heterosexual in this outfit. After he left, I felt completely empowered. I also had a good long laugh at his pride and promised myself that I would continue to be on the lookout for future opportunities to embarrass him. That afternoon, I informed him of my decision to dress him each day in a similar outfit until he had a certificate from the school that certified him as a nail technician. He had to learn that his sense of manhood and even his outward orientation was something for me to decide. He was a very good student.