My sixteen year old son Carl had a lazy streak a mile wide and a mile deep. He was always forced to clean his room and many times spanked for not doing it. I had all I could take when his sixteenth birthday was about to come in two weeks. All I heard was I want this and I want that, everything from a car to some stupid games that cost tons of money.
I decided it was time he learned money does not grow on trees. His father left us well off when he past three years ago and silly me went over board trying to make him happy and looking back I don't think he grieved at all when Harry died. All of his life was I want. Well now I want. I want him to learn a lesson.
My sister Ann told me about a boy where she used to live in Ohio that was made to wear girls clothes and stand out on the street corner with a sign that said " I am a selfish little sissy" because he stole his six year old sister's money to buy drugs. So I began searching the Internet on his computer and I saw a thing that said "History". I almost fell off the chair when I saw the things he had been searching and reading online. One was your website. I called Ann and told her, she came right over. After reading some letters she suggested we buy him some sweet sissy stuff for his birthday. We did plan a party but at the first one he got a few trinkets compared to the second one that only I and a few of others attended. After whining about the things he got at the party his friends from school and others attended I knew he need his come upends.
I called him down after he had went off pouting to his room since his school mates had left. My sister and her daughters had helped me lay out some pretty pink rumba panties ( that choice was Dana's my sister's daughter) she had choose them because he was always peeking up her skirt and telling her she wore sissy pants. We had a very full petticoat and a little girl style party dress from the fifties. Dana had also got him a bonnet and a bunch of bows. I got him lacy socks and Mary Jane style shoes. There was so many pretty things.
When Carl came down and saw the clothes he asked whose they were, We all began to sing Happy Birthday to him and he turned fifty shades of red. I made him sit down and told him we had found out about his computer searches and he was going to get a sweet sixteen party. Before he could do anything WE had him striped and dressed so fast. He was fighting but to no avail. Naturally he tried to take off the clothes but I stopped him and pulled him over my knee, soon his panties were down to his ankles and his butt turning red as his face. I stopped and said are you going to be a good girl he whined "yes Mother yes". I told him to stand and told Dana to pull HER panties up for her. He stood there as she pulled up his badge on his dress that said "Pretty Caroline". He looked down at it and started to cry. That was the name he used on the web pages he read or chatted in rooms with.
Pretty Caroline has spent many hours dressed in many different outfits doing womanly chores for myself and his auntie and cousin Mistress Dana. He does hate washing out her panties and hanging them out on the line behind their house next to the baseball park where he plays ball with the boys. By the way we have picked a wife for him and I know he likes her a lot so it will be a great marriage since she is really into his being her sissy maid. She has lots of money and is seven years his senior. He will never work outside the home except for me and the ones who know about his womanly duties. One more thing he does have a CB6000 and there are only enough keys for me and the ones in the loop.
Mother of Caroline