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Date Posted: 14:27:03 02/05/12 Sun
Author: Natalie
Subject: My son's first day in a skirt!

I am a friend of Elena who had posted here earlier. Elena strongly beliefs in dressing her son in girl's clothes quite often. She suggested that I try the same with my son (10). However, I didn't know how to start and handle possible resistance, so I never did. Until today!!
This morning, my son spilled his milk all over him and I had to get him changed. I still don't know what drove me, but I put him in dark purple tights and a purple sweater from his sister. He wanted to put on jeans but I told him that he was wearing tights and didn't need trousers over them.
He blushed but stayed dressed like this. My daughter (12) had chosen to wear a white sweater, white tights and black shorts over them. She enjoyed seeing her brother in her outgrown clothes and my son didn't feel comfortable but decided not to upset me more after the milk spill earlier. At noon we wanted to go out to have lunch and my daughter came down with one of her older jeans skirts and gave it to my son. He blushed and threw the skirt on the floor. I told him to pick it up and put it on. Again, I don't what drove me to tell him that. I was mad about the way he threw the skirt on the floor. He looked at me surprised and speechless. My daughter helped him into the skirt and zipped it in the back. The skirt hem was well above his knees and he tried to pull it down as it was so short. He looked so helpless and confused. My daughter and I had to fight not to start laughing. My daughter then got him some of her older boots and a winter jacket to put on. After a few minutes, my son was fully dressed as a girl. I called Elena and told her what we had done to my son. She laughed and said "He'll soon like it". Me and my daughter put our coats and we all went out to lunch. My son went behind us and tried to hide. My daughter was wearing her shorts, I was wearing pants - and my son in a skirt. I the restaurant he hurried up to sit down in a booth, so no one could see him but I decided to change tables and had him sit on a chair in open view.
The waitress addressed him with "young lady" and he blushed. Only then the waitress looked again and said "oh, are you.. you are a boy!". A few people looked our way but no one showed too much interest, except the waitress who asked my son if he likes girl's clothes. Before he could say a word, my daughter said that it was his first time in a girl's clothes. The waitress complimented him and I could see that my son was getting more and more embarrassed. So I ordered our food to get rid of the waitress. My son asked if he could wear pants later and told him that we would visit Elena and her kids and that we would not go home first. He asked if he had to play with Elena's kids in the skirt and we told him "yes, what else?"...
We had a great afternoon and since Elena's son was also in a dress it was okay for my son after a while. He didn't like that both girls were in pants (Elena's daughter was wearing red corduroy pants).
I could tell how relieved he was when he could finally undress tonight to go to bed. My daughter went and searched for more of her older clothes for her brother. I put them in his wardrobe and he looked but didn't say anything. I told him that he would be wearing girl's clothes from now on on certain occasions just like Elena's son. Again he did not say anything.
Well, we'll see how he takes it next weekend. I have planned for him to wear a skirt outfit on Saturday and a beautiful red dress and white tights on Sunday...

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