Sissy's Smile

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A femboy discovers the joy of womanhood.
991 words
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Maurice's mother gave him enough money to move where he wouldn't be recognized. The femboy tearfully kissed her goodbye and departed with two suitcases of pretty dresses, lingerie and beauty products. Maurice was sad about leaving his home, but the pantywaist was optimistic about his future. He was finally free to reveal the girl who lived inside him.

After Maurice settled into a one-room apartment he connected with the local LGBT community. The feminine boy wanted to study under a sissy training matron and asked for a referral.

Maurice was nervous about meeting his trainer. He imagined a severe dominatrix clad in leather with a whip in her hand. His mistress actually turned out to be a kindly white haired lady named Faith. She favored floral print dresses, like Maurice, and her most severe form of punishment was chair time.

Faith felt sympathy for the insecure nancy boy. He reminded Faith of the timid little sparrows in her garden. So, she began calling him Birdie.

Faith easily feminized Birdie. He was naturally submissive so there were no unpleasant masculine traits to excise. Birdie also had good fashion sense and he knew how to apply makeup and style his own hair.

Birdie could not afford the fee that Faith charged for training. So he worked at her home three days a week, performing household chores and preparing her meals.

In return, Mistress provided Birdie with a charming sissy maid uniform in pink satin fabric. The outfit included wonderfully soft chiffon petticoats and a sweet little server cap. Birdie offered to work seven days a week so that he could wear the scrumptious outfit every day.

After her initial evaluation, Faith identified a few areas where Birdie needed more feminization. The first was walking. Mistress taught Birdie to wiggle his hips like a girl and to take shorter steps. Birdie also needed voice training. So, Faith taught him how to speak in a pleasant melodious tone. After a little practice, Birdie's learned to walk with a frisky mincing step and to speak in a soft dovelike voice.

Finally Mistress worked with Birdie on his smile. She wanted to see a sweeter and more joyful expression his face. Unfortunately, the sissy was still insecure about his femininity and it showed on his visage.

Neither positive encouragement nor chair time punishment improved Birdie smile. So, Faith tried a new tactic. One afternoon when his sissy chores were finished Faith surprised Birdie with a darling little A-line party dress. The short skirted confection featured a pink and metallic floral design on a satiny ivory fabric. The scoop neckline and spaghetti straps were adorable!

Birdie was delighted with the gorgeous frock and thanked his mentor profusely.

"Change in my boudoir and wait for me there in front of the full length mirror," Faith told the exuberant Birdie.

Birdie usually changed in the guest bedroom and he had only glimpsed Faith's private dressing room. The chamber reminded Birdie of his mother's room with its sheer curtains and patterned wallpaper. There was also a lighted vanity with makeup, bobby pins and perfume. Birdie was thrilled to be in his mentor's lovely boudoir and it lent an extra-special ambiance to his wardrobe change.

After he finished looking around Birdie removed his sissy maid outfit and petticoats. Underneath he was wearing nylon brief panties, stay up hose and a Maidenform Natural Boost Shaping Bra with breast forms.

The excited Birdie lowered the girly A-line dress from this mentor over his head and then gazed at his reflection in her full-length mirror. He had never looked prettier!

Birdie was anxious for Faith to see him in the dainty frock. First though he primped his hair and touched up his lipstick. Then Birdie took a deep breath to calm himself and called Mistress in his songlike voice.

"I'm ready, Mistress", he cooed.

Faith walked up behind Birdie and they both gazed at his lovely reflection in the looking glass. Birdie was in sissy heaven!

"Is that a little smile on your face, Birdie?" asked Mistress knowingly.

"I guess it is Mistress," answered Birdie with a faint giggle.

"Let's see if we can make your little smile into a big wide grin," said Mistress.

Then she put her arms around Birdie's narrow waist, caressed him and whispered in his ear.

"You're the prettiest and the sweetest young lady I've ever known, Birdie," she said.

Faith's honied words and her soft embrace sent delightful girly feelings cascading from the curly tresses on Birdie's head right down to his painted toe nails.

"Oh, Mistress," exclaimed Birdie, "You've made me so happy!"

"Yes, Birdie," she replied, "and it shows on your radiant face."

Birdie realized that Mistress was right, he was beaming a warm and joyful smile. There was also a twinkle in his eye which made him more attractive than ever before.

"Birdie, a pretty girl with a smile like yours can light up a room. I want you to remember that always."

"I will, Mistress! I will!" squealed Birdie.

Mistress spent extra time with Birdie over the next few days to be certain that his smile would last. Then she took him to public places where he was usually nervous but he continued beaming.

Birdie's delightful visage along with his fetching clothing and the wiggle in his walk drew admiring glances from passersby. The sissy boy loved this attention which made him feel marvelously confident about his femininity. Birdie's smile became even more lovely and natural, and it was there for all the world to see!

Birdie's feminization under Mistress Faith had now come to a fruitful conclusion. She had transformed him into the lovely young lady that he was always meant to be. Faith was thoroughly satisfied with her work. So, she set her precious little Birdie free to delight the world with his femininity and glorious smile.

--

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Whippet_DarlingWhippet_Darling14 days agoAuthor

Dear Anonymous,

Thanks for your appreciation of my story. I like the gentle approach, too.

Sincerely,

Whippet_Darling

AnonymousAnonymous14 days ago

This is the kind of sissy/sissification story I like; no coercion, no humiliation, just natural, gentle progress to self-realization and fulfillment.

Of course, we come into the story with Maurice/Birdie already a confirmed femboy, so we don’t know what happened to him before the story begins, but that’s neither here nor there at this point.

Well done, please continue!

Whippet_DarlingWhippet_Darling16 days agoAuthor

Dear Anonymous.

Thank you. That is the essence I was trying to capture.

Sincerely,

Whippet_Darling

AnonymousAnonymous17 days ago

Very sweet!

Whippet_DarlingWhippet_Darling18 days agoAuthor

Dear MasterMarcoPhillips,

Thanks for your appreciation of my story.

If not Birdie, others like him for sure!

Sincerely,

Whippet_Darling

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