Sissy and His Mom Pt. 07

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A closeted femboy is nourished with maternal love.
976 words
4.48
5.8k
11

Part 7 of the 11 part series

Updated 03/21/2024
Created 03/06/2024
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Dear Reader,

This story is about a sweet mother-daugbrhter relationship that unfolds after sissy comes out to her. There are no sissygasms but lots of feminization. It might read better after church on Sunday than on a hot Saturday night.

Sincerely,

Whippet_Darling

--

In the weeks that followed his tearful coming out, Mother encouraged Daisy and helped him to look and behave like a girl. She bought him lingerie and a makeup kit; allowed him to borrow her dresses, skirts, blouses and shoes; and taught him feminine manners. Daisy and Mother had spent many joyful evenings together in her bedroom, trying on pretty clothing and accessories in front of her full-length mirror, and experimenting with new makeup looks at her vanity.

However, Mother was concerned about Daisy's well-being. He spent too much time alone in the house and he had lost touch with all his buddies. She felt that Daisy needed to get out more and interact with people besides herself. That would be difficult for a boy in girls clothing but she had a plan.

Mother was removing her son's makeup before bed one evening when she asked, "Daisy, how would you like to go clothes shopping with me?"

"No way, Mommy," he replied. "I can't let people see me picking out bras and panties!"

"Suppose we went to a big city where no one knows us and suppose that you wore a woman's wig?"

Daisy weighed this idea in his mind. It would be fun to shop in the women's section of a department store right along with real women. Pleasant images of he and Mother sorting through sensuous lingerie and trying on colorful party dresses overcame Daisy's concerns and a smile appeared on his face.

--

A few days later Daisy and his mother were unpacking in a high rise hotel room in New York City. Daisy had worn boy clothes over his lingerie during the bus ride from New Jersey but his suitcase contained dresses and shoes that he had borrowed from Mother.

Daisy's most treasured possession, though, was the lovely wig that Mother had bought him for the trip. He had tried on the hairpiece the previous evening, and they both admired the lovely strawberry blonde tresses cascading in curls to Daisy's shoulders.

When their clothes were put away, Mother said, "Let's get ready to go out, Daisy. Shall I do your makeup?"

"I'll do it, Mommy," replied, "but do you think I should go for the natural look or something more dramatic?"

"Natural is better for daytime, Daisy," she said. "We can wear evening makeup later when we go out to dinner."

Daisy applied his makeup very skillfully and then put on the lovely polka-dot puff sleeve dress Mother had bought him for the trip along with the slingback pumps that he borrowed from her. Finally, Mother put a wig cap over her son's hair and then fitted the blonde hair piece on his head.

As they departed through the lobby, Daisy looked straight ahead. He feared disapproving glances from hotel staff who would remember him as the boy who checked in just a little while earlier.

Their hotel was only a short distance from Macy's on 5th Avenue, the largest department store in the United States. Daisy walked nervously at his mother's side. This was his first time out in public wearing a dress and carrying a handbag.

Mother had taught Daisy to walk like a girl, talk like a girl and to keep a pretty smile on his face. The lessons were paying off. No one seemed to know that he was a boy, and a few passersby even smiled back at him.

Macy's Department Store was a femboy's dream come true. There were aisle upon aisle of beautiful dresses, slacks, and blouses. The intimate apparel section, by itself, was larger than the entire women's apparel section of the Macy's in their home town.

Long racks of hangers held chic bras of every kind, while pretty panties in all styles and colors were arrayed on the endless counter spaces. There were also specialty items that most stores did not carry such as corsets and garter belts.

Mother and Daisy perused all manner of women's wear, happily chatting as they strolled down the aisles. When she asked what he'd like to buy, Daisy responded excitedly that he wanted a corset.

"That's wonderful, Daisy," she said. "I'd love to see you in a corset. Let me find a saleslady to help."

"What? No, Mommy!" he replied. "She'll know that I'm a boy!"

"I don't think she will, Daisy," said Mother calmly. "You're wearing a girdle and you can try on the corset over your slip if you're concerned."

When Daisy reluctantly agreed, Mother found someone to help.

The saleslady, named Eva, showed Daisy and his mother underburst and overbust corsets. Daisy was nervous that the lady would ask him to remove his bra, so he said that he wanted an underbust.

Eva asked Daisy for his waist size and he responded that it was 28 inches. She selected a pretty Orchard corset with a floral design in size 24 and led Mother and Daisy to the fitting room.

Daisy was nervous about removing his clothes in front of Eva, and he needed Mother's help while unzipping his dress. Eva waited calmly and patiently. Then she instructed Daisy to grab the lacing bar which hung from the ceiling as she wrapped the stiff corset around his waist and laced it in back.

"Let me know if it gets too tight," said Eva as she began pulling the laces.

Daisy's watched his reflection in the mirror while Eva whittled down his waistline. Thrilling feminine sensations washed over Daisy as his attractive hourglass figure took shape.

--

I invite your comments, whether on-line or by email.

All my characters are of legal age.

Please rate this story
The author would appreciate your feedback.
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Whippet_DarlingWhippet_Darling12 days agoAuthor

Dear SissyBoy,

Thanks for your appreciation of my writing.

Sincerely,

Whippet_Darling

SissyBoy1WarszawaSissyBoy1Warszawa12 days ago

Daisy's wonderful experience - going to New York, hotel and leaving the room as a girl. Experiencing this stress and being confident and knowing that there is a loving mother next to you, nothing bad can happen. A shopping mall, a women's underwear store means an increase in pressure, joy and also the constant fear that someone will discover that I am not a natural girl. The wonderful feeling of trying on a corset is what every person like Daisy wants to feel and experience.

Whippet_Darling, you describe it so naturally and beautifully that when I read Daisy's story, I feel her every move, nerve, breath and heartbeat as if you were Daisy yourself. 👧🏻🩱👗⚧️🧒🏻❤️👩🏻👩‍👧

ps. Sorry for any mistakes and linguistic inaccuracies, I don't speak English.

Best regards, SissyBoy from Warsaw, Poland. 👩🏻‍🦳⚧️❤️👧🏻🧒🏻

Whippet_DarlingWhippet_Darling27 days agoAuthor

Dear MeChelleCD66,

Thank you commenting. I intend to continue this story.

Sincerely,

Whippet_Darling

MeChelleCD66MeChelleCD6627 days ago

keep writing more

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