Reformed in Dresses
A short story by Dennis

Mrs. Blake was the county’s last ditch effort for bad boys, before they were sent to reform school until they were twenty-one. Ask anyone in the foster care program, and they would describe how she made judicious use of petticoat training to make her boys better citizens.

The year was 1960, and one such young man by the name of Master Jason Billings would find himself entering her very feminine, but very strict, world. In her mid thirties Mrs. Blake sent chills down any young boy’s back. Yet, strangely, when boys thought of her, it was always with the curiosity, and the wonder, of what would it be like to have to really dress in girls’ clothes from the skin out.

Ann and Mary were new girls – real girls who were members of the staff – and had seen anything of Mrs Blake’s methods as yet.

“Ann and Mary, we have a young man of thirteen coming to join our happy little family. He will be here in about forty-five minutes; I want the spare room ready when he gets here. Mary, in the attic you will find suitable clothes. I want all the clothes up there brought down here and put away, including the underwear.”

Mary giggled never imagining anyone dressing a young boy in girls’ clothes, and especially girls’ panties and petticoats! Hesitantly she asked, “Mrs. Blake? You really don’t mean the girls’ clothing, do you? ”

Mrs. Blake laughed, “It is either girls’ clothes or reform school…I my self would much rather prefer the feminine clothing over the reform school, wouldn’t you?”

Mary, laughing, turned and went to the attic to fetch the clothes she was asked to. Mary could not wait to see how they expected a young boy to dress in girls’ underwear and dresses and yet not make a big fuss over it. She thought to herself, “It will be fun - that is one thing for sure.”

She remembered a time when she had wanted to dress her younger brother in her hand-me-downs, but had not dared to...

Ann was from Britain - she was here in the States for school and work, and she was going to work for Mrs. Blake for her room and board, and some spending money. She usually lived in England with her mum and dad, and two younger brothers, when not attending school. Mrs. Blake noticed the smirk on Ann’s face:

“What’s tickling your funny bone this afternoon?”

Ann turned,” Oh, I was thinking when mother petticoated my two younger brothers. Don’t take me wrong; petticoating does a troublesome lad wonders, and I help my mother dress my brothers. They were all the time fighting with other boys in the neighborhood, coming home with their clothes all torn and dirty, giving our mother fits. I still can see Mother pulling panties on them and training bras,” she said, laughing. “Sorry but I just can’t help myself.”

Ann went on, telling Mrs. Blake about her mother petticoating her brothers, and before long the two of them where laughing so hard that they had to sit down.

“Well Ann, you just became my number one helper in petticoat training our naughty boys, and I will give you a three dollar a week raise.”

Ann’s eyes widened. “Oh, thank you, Mrs. Blake! I didn’t expect that.”

Later that very day, two women arrived with Jason. The older woman introduced herself:

My name is Mrs. Stillmen, and I am the head of child protection and foster care in Two River County. This is Ruth Johnson, who advises me on the discipline of the children in our care.”

“And this - this is Jason Billings, thirteen, and a big pain in you-know-where. Jason likes to run away and give his mother all sorts of headaches. Jason, this is Mrs. Blake, and this pretty girl to her right is Mary, and the one on her left is Ann, and she comes from England. Won’t that be interesting? Would you say hello to them please?”

“Hello, Hello, hello”, turning towards each one of them. “Now may we go? I did as you asked me too.” He looked towards the door.

Ruth stopped him, “Not so fast there young man. Jason you have to stay here until you’re eighteen. If you run away or cause any problems it is off to reform school for you, do you understand, Jason?”

Shaking his head, Jason replied, “Yea, I understand. But why can’t I live with my Uncle Pete?”

“Your uncle has been in trouble himself, Jason. He really is not a suitable person to bring up any teenager.”

The two women left, leaving Jason Billings with Mrs. Blake and her two attractive assistants.

Mrs. Blake pulled Jason to her, “Jason, do you know what is going to be happen to you?”

Jason glared back at her, “You’re going to spank me?”

Mrs. Blake laughing, “Oh my dear boy…as far as you are concerned, a spanking would be a piece of cake. Would you care to venture another guess?”

Jason shook his head. Susan Blake then led him by the arm to his new bedroom. She ssked him if he had had a bath today or not.

“Yes. Do I have to take another one now?”

Susan shook her head. “No…to start with, I want you to give me all the clothes you are wearing now. Then put them in this box – oh, and your underclothes to.” She began to unbutton his shirt, as if he were a small child.

Jason felt very self-conscious with no clothes on, and Mrs. Blake, holding the box of his clothes, called out.

“Ann, I believe Mary wants to help us, if for no other reason than to watch and learn.”

Ann calmly locked the door. Jason wondered…how come they locked the door? I’m not about to run away with no clothes on. His answer was soon coming.

Ann smiled in Mary’s direction, and requested, “Now - would you like to choose the underwear that Jason will be wearing?”

Catching a glimpse of the pile of pastel nylon panties frothing with lacy trim, Jason gave a gasp, and tried to open the locked door.

“Yes Jason, is something wrong?” asked Mrs. Blake, smiling.

Running to her, Jason cried, “They’re going to put girls’ under panties on me; but I’m a boy! Please tell them to stop and give back my own clothes.”

Jason stood behind Mrs. Blake, putting her between him Ann and Mary. But Mrs. Blake stood him in front of her and said with an icy smile, “They are your clothes, honey.”

Mrs. Blake was adamant.  “Put them on yourself, or we will put them on you.” One foot at a time, he gingerly stepped in to the distressingly pretty panties, and then Mrs. Blake pulled them up slowly over his thighs.

“I hate you Mary!”

Ann pulled a petticoat down over his head, and adjusting it so the petticoat fluffed out and hung straight. “Jason, no one here is going to hurt you,” she said soothingly. “Believe me, you’re not the only boy to have to dress in girls’ clothing, my two younger brothers had to too.” Ann then helped put the dress in place, and tie the sash in a perky bow.

Mary could hardly contain herself. To her, Jason made a splendid little girl to be fussed with and pampered.

“Mrs. Blake, can we call him, or her, ‘Janet’ - that way I’ll have the little sister I’ve always wanted!” she cried, folding her hands in delight.

The three looked at each other, and nodded.

“Then it is agreed. Janet is Jason’s new name until he leaves here at the age of eightteen.”

Mrs. Blake told Jason to lie on the bed, and started pulling his stockings on to his feet. He was beyond shock, and felt like crying.

 “Mrs. Blake? Can I please wear my own underclothes to bed?”

Ann handed him a hanky, and Mrs. Blake replied, “That depends on you. For right now: No. But maybe sometime in the future.” By this time Jason had on white stockings with a lace patterning, and black Mary Jane shoes.

Jason remembered what Mrs. Bake said, “Oh, my dear boy…as far as you are concerned, a spanking would be a piece of cake.” Right now, reform school was starting to sound like a holiday in Disneyland.

Ann spoke to him sweetly, “Janet, honey, would you like to have some ice cream with me?”

Jason looked up, crestfallen. “Yes. Did your mother make your brothers wear girls’ panties and dresses for real?”

Laughing, Ann replied, “Yes! And I had to help her too. That was part of their punishment.” She led him in to the kitchen.

“Are they sissies now or real guys?”

“Oh, they’re real men now, they just learned to behave themselves properly, and to respect our mother, as well as other girls.”

The dress made Jason uneasy, having never had to wear one before. The next day was even worse, and filled with all sorts of girlish delights for Jason. In the morning after his bath he was put in to a beribboned girls’ vest, and a pair of pink rhumba panties, with a matching top, and a white little girls’ half-slip flared out under a blue pleated skirt.

He got dressed with little or no fighting at all, and made sure that his knee high white socks were nice and straight. However, it was after breakfast that frightening things began to happen. Mrs. Blake informed him, “Janet, today you and Ann and I are going shopping for clothes that will fit you properly.”

Jason’s eyes widened. “I get to dress like a boy again? Where are my clothes? So I can change, and I’ll be ready in a flash.”

Ann looked steadily at him. “You are wearing them Janet, it is a nice day so you will not need a coat.”

“No, I can’t go out dressed like this!” His shoulders began to heave.

“That is why you are going dressed in girls’ clothes, because you sob just like a cute little girl. But you can wear a nice curly wig that we have for you. You’ll look just like Shirley Temple. Won’t that be fun?”

Mrs. Blake took his hand as if he were a small child, and he was dragged out to the car. Inside the car Ann said, “Just pretend you’re a girl, or people will know you’re really a boy in girls’ clothes. Here - dry your eyes and wipe your nose, and before you know it we’ll be back home.” To test his docile obedience, she leaned over and began fussily smoothing and straightening out his skirt.

In J.C. Penny’s Mrs. Blake and Ann firmly led Janet in to the girls’ section. A smiling lady clerk in her 30s met them.

“Hello Mrs. Blake, hello Ann. Is this another new girl saved from the reform school?” She smiled indulgently.

“Yes, her name is Janet. Don’t be shy; say hello, Janet. Miss Thomas knows all about our sweet little girls you know.”

Feeling the blood rushing to his face, “Hello, Miss Thomas.”

The clerk had them follow her to the girls’ dressing rooms, where Ann and Mrs. Blake led him in to one of them. “Janet, let’s remove your outer clothes for now. Than after we’re finished having you trying on your new clothes, you can get dressed again.”

Jason could feel the pretty clerk’s eyes looking him up and down. There was no place to hide or run. His dress and slip were quickly removed, and Miss Thomas came back with a pastel pile of panties and tops.

“Let’s take off your panties, Janet.” Ann pulled off his panties. Whilst he stood, numb with embarrassment. When they had finished he had a rainbow of colors in panties and tops, and some party frocks that would have made some of the girls that he knew blush.

Thinking about going home, Ann asked, “Mrs. Blake, let’s stop at Denny’s for a bite to eat?”

Mrs. Blake smiled. “Oh, that would be grand! And a good lesson for our little Janet too.”

That was it; tears started streaming down his face. When he had been hurriedly taken out of the shop, and sat in the back of the car, he pleaded, “Please! I know I‘ve been really bad…but can’t I just stay in the car, Mrs. Blake?”

Ann turned around to face Jason. “You have been a real little demon in trousers, running away like that...just doing everything to cause trouble for every one who has tried to help you. Yes, right now you will do or say anything, just so you will not have to go into Denny’s dressed like a girl. But the answer is no. You will have to face your punishment like a young lady, or, in your case, a young boy wearing girls’ clothes. Here - wipe your face and let’s have something to eat.”

Inside the restaurant, Jason felt like ever eye was watching him.

Because of his embarrassment, no one realized he was a boy dressed as a girl. As they sat there eating their lunch, a lady with two kids entered the restaurant. As they passed, Jason realized with a sudden shock that the little girl was a boy. All doubt was removed when the older lady spoke. “Martin, quit your crying, and I don’t care if you don’t like wearing girls’ clothes! As long as you live with me you will dress and act like a girl.”

A table of wide-eyed girls started laughing, and teasing the boy. The rather overpowering lady spotted Mrs. Blake, and turned to Martin again.

“Would you like me to send you to live with Mrs. Blake? She likes boys dressed as girls. Hello Mrs. Blake, is that little girl your daughter?” she asked with a knowing smile.

“No it is my ‘niece’, and she has come to live with us on account of a court order. Say hello, Janet.”

“Hello, it is nice to meet you.” Jason’s eyes were shyly downcast, and he was sliding behind Ann.

The ladies were talking, and something that they said sent a jolt of fear through Jason.

“Could Janet come over to our place to play with Martin? It would so help him to know how to act like a girl.”

Nudging Ann, Jason whispered urgently, “No, no…please no!”

Ann laughed. She turned to Martin's formidable mother: “Maybe later in the summer; were quite busy at this time.”

Finally they where in the car heading for home, “Thank you Mrs. Blake, for not telling them I was a boy!” Ann kissed Jason on the cheek. “You are a nicer boy already! Now admit it; it’s fun being an obedient little girl, isn’t it?’

Jason had a hard lesson to learn, but in time he did, and today he is a lawyer. With his wife April and two daughters they run a home for boys who need a loving dose of petticoat discipline. Oh, and Mrs. Blake? She is now living with Jason and his family, and helping with the wayward boys.

I know, because I am Jason Billings, and this is my story.

The End

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