I had my first legal dressing session when i and my girl friend moved in.... Rather that came as a punishment as i had not done a work which she had asked me to do.... She asked me if i was ready for the punishment.... I just nodded (but hell yes) as it was first legal dressup..... To my surprise she asked me to wear the clothes that she had worn as she was changing to nighties.... I was ok with it and we njoyed the session.... later she told me she liked me dressing up so she bought some dresses for me as well.... It went to a next level when she started doin my make up keeping me dressed.... Now its like wen we at home i dress 4 days a week as a girl and she dresses 4 days a week as a boy..... Just luving it and My sweet GF