Sissy and His Mom Pt. 11

Dear Reader,

This story began with the sweet mother-daughter relationship that unfolded after sissy came out to her. Mother supported her son's femininity and encouraged him to open up with other people. Recently he has met a girl whom he fancies. The friendship has enriched his life but also complicated it. Daisy faces his biggest challenge as the story reaches its conclusion.

Sincerely,

Whippet_Darling

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In part 10, Daisy and Mother were visiting his new friend, Caitlin, and her mother. The moms decided that they should all go for a walk in the park. Daisy, who was wearing a miniskirt and heels, borrowed capri pants, a crop top and flats from Caitlin for the outing. Afterwards Daisy wore his friend's clothing home and left his miniskirt with her.

Caitlin texted Daisy the next day, "How did you like wearing my outfit?"

"I loved it! Can I keep it a while longer?"

"Of course! I hope you don't mind but I tried on your mini and I adore it."

"I'm glad you like it, Caitlin. By the way, when can I see you again?"

"How about now? I'll borrow mom's car."

"Great! Here's my address..."

--

Daisy excitedly informed his mother that Caitlin was coming to visit.

"That's wonderful, Daisy!" she enthused. "I'm so glad that you're becoming better acquainted, Sweetie. You need friends your own age. By the way, have you thought about revealing your secret to her?"

"No way, Mommy! She'll hate me and I'll never see her again," whimpered Daisy.

"Caitlin seems like a nice girl, Daisy. So she might understand. Anyway, you and I need to talk this over soon because Caitlin is sure to find out eventually."

That thought sobered Daisy while he waited for Caitlin. When she arrived and threw her arms around him, though, his world turned rosy again.

Daisy couldn't wait to show Caitlin his bedroom which had just been redecorated. He now had a queen sized bed with a ruffled canopy, his own vanity for beauty products and a full length mirror. After Caitlin said hello to Daisy's mother, the two friends hurried upstairs and closed the door behind them.

Daisy looked over Caitlin who was wearing the faux leather miniskirt that Daisy had left at her house. She had completed her outfit with a pink satin blouse borrowed from her mother, glossy nylons and stiletto heels. Caitlin was smoking hot and Daisy felt a stirring in his panties.

"I'd love see what's in your closet, Daisy" said Caitlin.

"Okay," answered Daisy, "but it's mostly frilly stuff and I know you don't wear that style."

"Actually, Daisy, girly clothing looks so good on you that I might like to add some to my own wardrobe."

Daisy happily showed Caitlin his dresses, skirts and blouses. His friend especially liked a cherry red polka-dot puff sleeve dress that Mother had given him.

"Would you like to try it on?" offered Daisy.

Caitlin eagerly accepted Daisy's offer and removed her top and miniskirt. The feminized boy gaped at his friend's marvelous body adorned with gorgeous lingerie. Caitlin's delectable breasts were supported by a Wacoal Lace Embrace Underwire bra with decorative straps. She wore pink nylon panties over her pantyhose just like he did.

Daisy helped Caitlin into his polka-dot dress and then zipped her up. Caitlin admired herself in the mirror and then twirled like a ballerina to see the dress fly out.

"This is so much fun!" exclaimed Caitlin as she reveled in Daisy's pretty frock.

"What's gotten into you, Caitlin?" asked Daisy merrily.

"You've gotten into me, Daisy," replied his friend with a broad grin. "I'm so happy that you turned me on to my softer side."

"I love your bedroom too, Daisy," Caitlin added. "I wish I had a canopy bed!"

Then Caitlin sprawled out on the pink duvet of Daisy's bed and smiled invitingly at him. When Daisy laid down next to his friend, Caitlin kissed him.

The kiss sent shivers of delight through the feminized boy. Daisy wanted more but feared that the stiffy in his panties would give away his secret. So he drew back.

Caitlin was highly aroused, too, and the emotional girl mistook Daisy's pulling back as rejection.

"I shouldn't have done that, Daisy," said Caitlin shamefully. "You must think I'm a pervert. I'd better be leaving."

Tears welled up in Caitlin's eyes as she hurried down the stairs and through the house. Daisy was crying too as he tried to catch his friend before she could get away. Fortunately, Caitlin's escape was foiled by the front door which was locked.

By his time Daisy's mother had come to see what all the fuss was about. Caitlin had her back braced against the door like a trapped animal and she was sobbing openly.

"What's wrong, girls?!" implored Mother.

Daisy began to answer but Caitlin interrupted.

"I'm so sorry! You've both been incredibly nice to me and I spoiled everything. I'm bad and I don't deserve a friend like Daisy."

Mother was baffled by Caitlin's incoherent explanation.

"Why are you bad, Caitlin? What did you do, Dear?" she asked.

"I'm all mixed up about boys and girls," said Caitlin nervously, "and I kissed Daisy."

Mother recognized this as the turning point, and she looked expectantly at her son.

Daisy summoned up his courage and spoke softly to his friend.

"Caitlin, there's something I need to tell you."

--

Thank you for reading my story.

I hope you enjoyed it.