Karen explained how things would follow.
“The naughty boys’ room is also a fitting room I think that Ollie should stay standing as he is.”
Mom nodded. My brother was standing with his trousers around his ankles and his underpants around his knees. His very red ass was visible.
As we had discussed earlier I went out and I offered my brother some possible clothes. They were a jumper, a blouse and a pair of definitely girlish but rather plain panties. I guess they looked a lot like I wore and say 8 or 9.
“How would you like to wear this dress and these panties?”
I asked in a friendly manner. He said nothing, I think that he did not dare say he did not like what was on offer but, after his spanking, he would not directly say "no."
Mom said:
“It’s alright Ollie; I can see you don’t like the clothes Rosemary chose. That’s fine. I think you should have something prettier and more in keeping with your emotional age.”
Mom then picked up a more childish dress. It was very fussy. It had a sewn in petticoat. I remember a photo of me in such a frock; I must have been 3 or at most 4 at the time. The new frock also buttoned up at the back. There were a lot of very small buttons there. It would be impossible for him to unbutton the garment himself.
My brother did not resist as Mom unbuttoned and removed his shirt.
“I think you should step out of your pants.”
Mom said, and he complied. He did not resist as Mom pushed his arms into the arms of the dress. Then she talked to me:
“Rosemary, would you button up your brother’s pretty new dress?”
I did so. Actually given the smallness of the button and button holes it might have taken a while for anyone. I made sure to do this as slowly as possible. I pointed to a mirror. He just let me do what I wanted.
When I was nearly finished Mom came back. She offered a pair of panties. They had a cartoon figure, Minnie Mouse. Mom then reached and pulled down his boyish, now inappropriate, underpants to his ankles.
“Lift this foot.”
He obeyed and the underpants were removed from his left foot,
“Lift this foot.”
Not only did Mom take off his boy undies but also slipped on the little girl panties.
“Now the other foot.”
The childish panties were slipped on and pulled up under the new dress. A further instruction followed:
“Sit down child.”
He obeyed. Then Mom gave me some socks.
“Would you put the child’s socks on him?”
I did so. The socks were very bright white. They just went to his ankles. They had cartoon pink rabbits on them. Next came very black, t-bar sandals, which I slipped onto his feet and fastened them for him. You can imagine that he looked quite a sight when he walked out of the room into the main part of the shop.
As he did so I saw an interesting thing. Another young man, in a skirt and blouse, was curtseying
“Thank your for my skirt.”
He curtsied
“Thank you for my pantyhose.”
He curtsied.
“Thank you for my blouse,”
He again showed girlish respect. An 8 year old girl was sitting down. He looked about 16. His Mom was watching. I had a question for my brother.
“Do you know how to curtsey?”
He shook his head. I then asked the 8 year old
“Could your brother teach my brother to curtsey?”
“Tammy, teach the boy to curtsey.”
The next half an hour was very comical. My brother’s efforts, even at the end, were not that good. At the end he repeatedly curtsied thanking me for his sandals, his Minnie mouse panties, his socks with pink rabbits, and finally for the pretty dress.
Finally Ms Watson came out.
“Ollie, although it would probably do you good we feel you cannot wear you pretty dress outside. You can wear this skirt.”
She showed him the tartan garment. There was a surprising amount of pink in the tartan pattern.
“Lots of people will think this is a kilt. But it is not, it is a tartan elasticized skirt.”
I held my brother’s hand on our walk home. I knew, and so did 80% of those looking at him, that under the skirt disguised as a kilt he wore a petticoat and childish panties.