Sissy and His Mom Pt. 08

Story Info
A femboy is nourished with maternal love.
1.2k words
4.61
6.7k
13

Part 8 of the 11 part series

Updated 03/21/2024
Created 03/06/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Dear Reader,

This story is about a sweet mother-daughter relationship that unfolds after sissy comes out to her. There is not much sex 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 she taught him feminine manners. Daisy and Mother had spent many joyous 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 he needed to get out more and interact with people besides herself. So, she planned a weekend shopping trip to New York City.

After unpacking in their hotel room, Daisy changed from his boy clothes into a lovely polka-dot puff sleeve dress Mother had bought him for the trip. Then he put on his curly blonde wig and applied his daytime makeup.

Mother and Daisy walked to the Macy's Department Store on Fifth Avenue where they happily browsed aisle upon aisle of lovely ladies apparel. Daisy's prize purchase was an steel boned corset with a pretty floral design. A saleslady had taken Daisy and his mother into a fitting room and tightly laced him into the corset. His shapely new figure pleased Mother so much that she bought him a little black dress to go with it.

--

Mother was encouraged by Daisy's first appearance in public dressed en femme. His interaction with the saleslady especially gladdened her. Now they were back in their hotel room getting dressed for dinner. Mother hoped that the evening would be another rewarding experience for her feminized son.

Daisy's little black dress was a fetching off-the-shoulder style with a stretch bodice and a taffeta tiered skirt. Mother lent him a bandeau bra stuffed with tissue to enhance his bosom. The dress fit snuggly at Daisy's corseted waist and a short petticoat under the skirt accentuated his hourglass figure.

Mother helped Daisy with his evening makeup. She gave him the full treatment with darkly dramatic eyes and seductive red lips. Then she painted his fingernails to match. While his polish dried, Mother asked Daisy to stand in front of the mirror.

Then she surprised him with a gorgeous pearl necklace. Mother stood behind Daisy, pulled aside his hair and fastened the lovely strand at the nape of his neck while they both looked in the mirror. Daisy gasped.

"Thank you, Mommy!" he squealed with delight.

"These were your grandmother's pearls until she gave them to me, Daisy, and now I'm passing them on to you."

"I love them, Mommy!"

"You're a proper young lady now, Sweetie. I'm so proud of you!"

Then Mother wrapped her arms around Daisy's narrow waist and drew him to her bosom in a tender embrace.

--

When Mother and Daisy departed through the hotel lobby, she noticed several ladies and gentlemen glancing at her glamorous son. For his part, Daisy smiled demurely, walked with small steps and wiggled his hips, just as Mother had taught him.

There were several taxis waiting outside. A driver opened the curbside door of his cab and waited courteously while Daisy and his mother seated themselves. Mother had been teaching Daisy to speak in a songlike female voice, so he gave the cabby their destination. The driver didn't seem to notice anything unusual. Mother and Daisy exchanged private smiles.

The hostess at the Meduza Mediterranea restaurant showed the pair to their table. Then she held Mother's chair for her while their waiter held Daisy's chair for him. The waiter took their beverage orders and departed.

While Mother browsed her menu, Daisy retrieved the compact mirror from his purse and gazed at his reflection. He was mesmerized by his own pretty face, his stunning pearls and his off-the-shoulder dress. Daisy had never felt so wonderfully feminine before and the excitement became overwhelming. Then something unexpected happened and Daisy blushed deeply.

Daisy leaned over to his mother and whispered, "Can you come with me to the restroom, Mommy, please?!"

--

"What's wrong, Daisy?" Mother asked when they were alone.

"Mommy, I think I've wet myself a little bit," said Daisy with embarrassment.

"Do you mean with pee or the other thing, Daisy?"

"The other thing, Mommy. I'm so sorry!" he whimpered.

"It's alright, Dear," said his mother. "Girls sometimes get wet down there when they're excited."

"I know, Mommy," said Daisy, "but I'm afraid this will show."

"Let's go in a stall and see," suggested Mother.

Fortunately Daisy's skirt and petticoats had remained dry. His pretty nylon hipsters were soaked though, so Mother had to remove them. Then she dried the crotch of Daisy's pantyhose with a feminine pad from her purse.

"You'll be fine for tonight, Daisy, but I think you should wear a liner in your panties from now on."

"I will, Mommy, thank you," replied a much relieved Daisy.

Mother and Daisy touched up their lipstick and primped their hair before returning to the dining room. She deposited her son's panties in the trash on the way out.

--

Dinner at the Meduza turned out splendidly for both Daisy and his mother. Afterward they walked back to their hotel while browsing store windows along the way. At a home furnishing store, Mother asked Daisy whether he might like to redo his bedroom in a more feminine style. She suggested adding a vanity of his own and replacing his bed with a canopy model. Daisy relished the idea and added that he would love a full length mirror, too.

Back in their hotel room, Daisy and his mother prepared for bed. He unzipped Mother's dress and helped her remove it over her head. Daisy had become quite accustomed to seeing his beautiful mother in her lovely intimates. Tonight Mother was wearing a Glamorise Magic Lift bra with lace overlay on the cups and a pretty little bow in the center. Daisy loved his mother's voluptuous bosom and longed to have breasts of his own one day.

Mother and Daisy slipped into their matching satin peignoir sets. Then they laid on the king size bed and chatted about the delightful evening.

"You're getting a lot of attention, Daisy," she said with a smile. "How does that make you feel?"

"I love when people look at me, Mommy!" said Daisy. "It makes me feel warm inside!"

"I'm delighted to hear that, Daisy. It's much better than hiding out in your bedroom, isn't it?"

"Yes, Mommy. Thank you for showing me how lovely it is being noticed."

Mother and Daisy happily talked about girlish things until past midnight. Then they removed their peignoir robes and snuggled under the sheets in their baby doll gowns. The two continued their feminine banter, giggled and gossiped until they drifted off to dreamland.

--

I invite your comments on this story.

I enjoy corresponding about feminine apparel, too.

All my characters are of legal age.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
SissyBoy1WarszawaSissyBoy1Warszawa23 days ago

You describe beautifully how, step by step, Daisy becomes a real woman, both emotionally, mentally and even physically (although she still has a little treasure called a clitoris). In many places I feel like Daisy and I would love to have a mother like her.

Whippet_Darling I am enchanted by your story and I read each subsequent part with great interest, warm feelings and emotions.

Please continue writing the story of Daisy and her mother. 👧🏻🩱👗⚧️🧒🏻❤️👩🏻👩‍👧

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

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

Whippet_DarlingWhippet_Darlingabout 1 month agoAuthor

I am glad you like it sissymicki!

sissymickisissymickiabout 1 month ago

Thank you so much its wonderful

Whippet_DarlingWhippet_Darlingabout 1 month agoAuthor

Dear 300bowler300 and anonymous,

Thank you for your comments and I'm glad that you like the story. I hope you won't be too disappointed that it doesn't go as far as you seem to hope.

Sincerely,

Whippet_Darling

AnonymousAnonymousabout 1 month ago

Very much like following this saga. Hope that as Daisy's progression into femininity evolves, that his mother will prepare him and introduce him into sissy sex and help him towards becoming gay.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
9 to 5 After losing his job, a friend suggests a radical plan.in Transgender & Crossdressers
Wife's Trained Sissy Wife trains sub sissy.in Transgender & Crossdressers
Social Media Star Boy becomes an unwilling lingerie model for online viewers.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
More Stories