Chapter 4: So the next morning, as instructed, Oliver went to a local charity shop. His sister happened to know some of the volunteers at the shop. It was a Saturday and it was quite busy. Oliver handed the lady who seemed to be in charge a note, that he had hand written but Ann had dictated. It read:
“My wife insists I do house work. I said it is girl’s work. Please find some suitable clothes for me and make sure that they fit.”
Oliver also handed over a pound note and a ten shilling note, quite a lot of money in those days.
Five or six volunteers popped into the changing room in the next half an hour as they checked that the various skirts, blouses and dresses fitted this particular customer. He left with a bag containing 2 bras, 8 pairs of panties, five slips or petticoats and 4 very flowery dresses.
Ann sat down and did her studying for the rest of that Saturday. Every so often she got up and watched, and took a few photographs of her husband hovering, scrubbing the kitchen floor and scrubbing in the bathroom as well as washing the dishes and doing the ironing.
Ann did not feel like cooking. Her husband did that. She did, however, feel quite proud of what she had achieved. She invited Molly and Jane
The meal that Oliver cooked was adequate. However Jane was very upset:
“Ollie, you bought women’s clothes.”
He was defeated and vulnerable:
“Yes, that’s what you said.”
His tall sister smiled and said:
“Oh no, you did not talk about women’s work. You talked about GIRL’s work. I think you should wear GIRL’s clothes, as childish as possible. I think you need a spanking, have you anything to say.”
Ollieattempted a curtsey and said:
“Please Miss Jane would you give me a hard spanking.”
Jane sat on the sofa. Oliver placed himself in the appropriate position. Very carefully and slowly firstly Jane pulled the skirt of his dress out of the way. Next the very frilly slip went up. Finally his pink panties were pulled down to his knees.
For about a minute Jane spanked her brother with her hand. It stung. Next she took a very heavy hairbrush. Olliewas crying after less than a minute with the hairbrush. However the spanking carried on for five minutes. Ann opened the kitchen window. The sound of his crying, as planned, went to their next-door neighbor, Mrs Bloom.
They sat down, to eat. Olliestood in the corner with panties around his ankles and holding up his slip and dress.
Just before they ate Ann dialed the number of her next-door neighbor. She said, in a loud voice:
“I was a bit worried that you might have heard someone crying and wondered. You have no need to worry. It is just that my husband and he had to be spanked.”
The response surprised Ann.
“I would have loved to watch.”
Lucy Bloom’s father had often spanked her, more often than her rather less well-behaved brother. She had married, Ben, a lovely man who, sadly, was knocked over by a car and killed.
Ann had a question for her neighbor:
“Have you cooked your dinner yet?”
“No, why?”
“Oh, it is just that we happen to have spare supper.”
Two minutes later Mrs Bloom arrived. She pushed a big old-fashioned pram with her 6-month-old twins Nancy and Robert. They were asleep.
As they ate Jane explained what had happened. She told Nancy about Oliver’s problems with treating women with respect.
“You made a pass at me, didn’t you?”
Ollie stood in his corner, holding up his skirts and showing his very red behind. He did not know whether to reply. Ann had the answer.
“I think that Ollie should SHOW Mrs Bloom why he won’t try to impose himself on ladies. Turn around.”
Lucy saw the chastity device. Jane added.
“Well it does seem appropriate that he should be sitting down to go pee.”
They had a lovely dinner. They talked. Molly said:
“I agree that it would be good for Ollie to dress as a little girl rather than a grown up. He does talk about ‘girls’ rather than ladies. He is also very immature. But unless we specially make something, which would cost a lot of money how can we find the right frocks.”
Ann had an idea:
“Mrs Bloom, you know your Maternity dresses looked a little childish, and with some adjustments could be made very childish. Have you still got some?”
Lucy laughed:
“Oh, I would love to. By the way my American cousin Sam, that’s Samantha left her training bras here after her visit, she was so proud to wear a proper bra. And I can make the adjustments.”
Jane had one more thought:
“Shouldn’t Mrs Bloom be compensated?”
Lucy was less sure:
“Well, I don’t know. I know that paying for Jessica’s school and Ann’s college books cost a lot of money. And well Ben had a good pension scheme and life insurance. So although I’m a widow I am NOT poor.”
Jane explained her brainwave.
“Perhaps not money. How would it be if Ollie paid for his new dresses and the work you are doing by, say, washing Nancy and Bob’s nappies for the next three months.”
Jane then talked to her brother:
“Isn’t it nice of Mrs Bloom to let you have pretty dresses. And I’m sure you’ll be very glad to help her out with the nappy washing won’t you?”
He nodded. This was not enough. He ended up having to write, and then read out loud a contract:
“I Oliver Hill, also known as Ollie, promise to wash all the wet and dirty nappies belonging to Robert and Nancy Bloom.
“In return Mrs Lucy Bloom promises to adapt her old maternity dresses so as to resemble those of young girl children and to give me the training bras and panties once worn by her cousin Samantha.”
They both signed and Jane, as a lawyer, witnessed the legally binding contract.
So whilst Jessica was away at school Ollie spent all his time at home wearing rather childish dresses. He did all the housework for his wife and also for his sister. He did other work for his neighbor. On a number of occasions he suffered spankings, usually with other ladies watching.
They did not feel that it was right for Jessica to see him in his frocks or across his wife or sister’s knees. Still Jessica could not help noticing that her Daddy now did ALL the housework. He even tidied Jessica’s room for her. Also the trousers he wore were often in pastel colors, and had once belonged to ladies.
Jessica did not see the training bra and childish panties her father wore underneath. Neither did she know that when her aunt invited her father to her home it was usually for a spanking.