I have been married for about 22 years and my Mother-in-law has known that I loved dressing as a woman for about as long. She has always been very supportive and has even given me tips on how to be the perfect lady. She is one of those older generation women who are very feminine, very womanly. What I would call a very classy woman. A few years back I had an occassion to go and visit her while on a business trip. As we sat and chatted, our conversation turned to my dressing up. She asked me how I was getting on with it. I said fine, but was tried of dressing up alone. It was quiet for a long minute before she said, would you like to dress up with me? I was dumb founded. She just continuede and said, I think we are about the same size. What size bra do you normal wear? I told her that I was a 38C. When I told her this a smile came over her face and she said, the same as me! She took me into her bedroom and asked what would I like to wear of her's. All I could say was everything. She laughed and said, you get undressed while I pick a few things out. As I got undressed I could hear her going through her drawers picking things out. She finally called for me to come in to her dressing area. She looked me up and down and said, I'm glad you shave your body especially your legs. She had laid out her things for me to wear and started by handing me a pair of her panties. As I slipped them on I started to feel so feminine. It was a feeling I have never forgotten. Next she handed me her bra. It did fit perfect and I loved the fact that we wore the same size. She helped me to stuff my bra as I normally did and I soon had a perfect set of C's. She laughed and said, "We could be sisters!" Her wonderful sence of humor helped to ease the tension that I was feeling and helped me to really enjoy the experience. She had chosen a pair of slacks and a turtle neck sweater that I had seen her wear many time which made it even more special. After I was dressed I stepped into a pair of flats she had chosen for me. She said there, now that's better. She had me model for her walking back and forth a few times. Then she said, shall we do your make up? She spent a lot of time explaining to me what she was doing as she made me up. When she had finished we stood looking in the mirrow together and she asked me what I would like to do. I said go for a walk together around the neighborhood. This was something she wasn't expecting. I figured it was pretty safe as it was now night and there are very few street lights where she lives. She finally gave in and we put on our coats and walked out. I slipped my arm through hers like I had seen other women do and we walked out into the night. It was the most incredable feeling I had ever experienced. And I was amazed to think that it was my Mother-in-law who had made my dream of being out as one of the girls come true. When we got back to her house I gave her a big hug and a kiss and couldn't thank her enough. Now when ever we are able to get together she lets me go into her bedroom and get all dressed up in her things so we can have a girls night together.