I don't know why i didn't do it but i know wished i would have. About five year ago we were waiting for our house to be built and we were living with my in laws. They are really down to earth people and love to have fun. It was halloween and we all dressed up, and you know what i dressed as. My wife and mother in law were throwing me cloths to try on and mother in law decided that i should be a hooker. When i was trying on the cloths my wife told me you must be loving this and got my heels and told me to put them on and she would tell her mother that i had the heels because i dressed as a girl a few years ago for another halloween party. My mother in law could not believe the amazing legs i had and gave me a skirt that was long down to my ankle's. I put in on and came out of the room she told me to walk over to her, she cut a slit from my ankle all the way up to my waist. She then gave me a new pair of stockings and a garter belt and both of them did my make up and finish dressing me. We then went around to our friends house's and having a laugh as we were all dressed up. We went to my sister in laws house and she had all her family there and we had a lot of fun there, everyone couldn't believe how good i looked and it felt great to be dressed. Well last weekend we went to my sister in law's houses for a BBQ and all her family were there, and after dinner her mother turned to me and said do you remember that halloween you came here all dressed up you looked great and she turned to her daughter and said you two are almost the same size get some cloth so he could dress for us again. Well my heart started rushing and everyone started encouraging her to get some cloths. I said no i can't and my sister in law went in and came out with some cloths and said go try them on. When i looked at the cloth i seen she put a pair of lacy black panties, black pantyhose a purple padded bra and a short skirt and a lacy top and she told me she has a pair of open back shoe,s that would fit, she was one size smaller then me. Everyone was pushing me to try them on and all i was doing was looking at the cloth and wanting so bad to put them on but i kept saying no. The hole time she didn't move those cloth and she kept asking me are you sure you don't want to try on my cloth's, i would love to see you wearing my cloths. It drove me crazy just thinking about it, i almost shot in my pant's. Well i didn't and now i regret it and that i may never be able to try on her cloth again. Even my wife told me that i should have did it, that i would have enjoyed it. Everyone was disappointed.