Friday, May 3, 2024

Five Days to Sissy



FRIDAY

“There will be a surprise for you at school today, Alan,” his stepmother told him as ate breakfast.

“Haven’t I had enough surprises this week?” he asked, looking down at his burgeoning breasts, his shiny shoes with their bows and all the other changes he had gone through since Monday.

“I’m not responsible for this one,” she replied…well, not directly, she thought to herself.

Thirty minutes later, Alan sat with the other students in the sissy section as the principal explained some new rules. “The board has decided it would be best for all our students if the sissies are required to wear the same uniform as the…um…real young ladies in the student body. So, for those of you who have been wearing trousers or non-regulation skirts and dresses, you will find your new school clothes in your lockers. As I said, they are identical to the outfits all the girls wear—with a few modifications to make it clear you are decidedly not real girls. Go now and change.”

Apprehensive, Alan went to his locker and found the uniform. It consisted of a crisp white blouse with the school emblem and a pleated tartan skirt. The difference from the “standard” uniform? The skirt was incredibly short—ending a full nine inches above his knees and beneath it was a built-in petticoat that made it seem even shorter and girlier. The accessories were a bow at the collar in the same pattern as the skirt and white knee socks. A note was pinned to the blouse: “Shoes are the sissy student’s choice, so long as they are black patent leather.”

Resigned to his fate, Alan removed his male shirt and pants and put on the blouse and skirt. He removed his shoes, pulled on the knee socks, then stepped again into his mary-janes. He glanced around the locker room at the other sissies. Yes, this had made them all look very feminine, even the ones who didn’t wear makeup…and the ones who sported C-cup tits and high heels looked positively womanly.

He finished the school day and was met by Violet and his stepmother. “At last, my sissy stepson is complete! Come with me, we will celebrate by buying your first party dress!”

THE END

Thursday, May 2, 2024

Five Days to Sissy

THURSDAY

By now, Alan’s mornings had a regular routine. He awoke to find his lingerie on his dresser. He put them on, then reported to the dressing room where Violet did his makeup and supervised his dressing for the day. “Today, Master Alan, Ma’am and I will pick you up at school and we are going shopping. Won’t that be fun!” Knowing that any other response would be of no avail, he smiled and nodded.

School that day was much like the day before. He joined the other sissies in their activities. For the first time, he noticed that he was the only one wearing obviously male footwear. The other sissies were shod in a variety of ways, but all of them quite feminine and girly. A few wore sneakers in pink, some had on ballet flats. Patent leather, both black and pink, seemed to be popular. And one sissy minced about in a pair of pumps with four-inch heels. Oddly, Alan found himself envying his classmates with the most girlish shoes.

As he exited for the day, Violet met him and escorted him to his stapmother’s car. Without a word, they drove to the local mall. Upon arrival, his stepmother directed them to a shoe store. “My sissy stepson requires an appropriate pair of shoes,” she told the clerk, who rushed off and returned with a half-dozen choices, ranging from pink mary-janes to stunning high heels. Alan’s eyes were drawn to a pair of mary-janes in black patent, with low heels and a glittery bow on the instep.

“Yes, these are a very popular style among our sissy clientele,” the clerk commented. “We also have them in pink and red, of course.”

“We’ll take a pair in each color in Alan’s size,” his stepmother said. “Violet, assist him in getting into the black patent pair while I arrange payment.” Violet helped him slip into the shiny shoes and buckled them tight. When stepmother returned, she had another small item with her. “Use these locks to secure the shoes to his feet,” she told the maid. “Alan must get used to wearing them constantly.” Violet inserted the tiny silver locks into the buckles of each shoe, closed them and handed the key to his stepmother, who dropped it into her purse.

On rising, Alan discovered even these slight heels altered his posture and gait. He realized he now walked like a girl!

Wednesday, May 1, 2024

Five Days to Sissy

WEDNESDAY

So, it turned out school wasn’t nearly as bad as Alan imagined. Since his stepmother had advised the administration, he was transferred to a special section for sissies and other feminized boys. There were ten other students in the group, in various stages of transition. A few were nearly impossible to distinguish from true females and one was wearing just lipstick to acknowledge his emasculated status.

Still, Alan was alarmed when he awoke to find yet another step would be taken on Wednesday. In addition to a pair of lacy pink panties, a matching bra lay upon his dresser. “Bring this to the dressing room” said the accompanying note. Knowing by now that there was no use in resisting, he pulled on the panties, picked up the bra and followed instructions. Violet was waiting for him at the vanity. “That’s a good sissy,” she said, smiling. “Now, sit while I fix your face and then we’ll try on your bra.” Within minutes, she was done. “Stand up, dear.”

Alan obeyed and the maid wrapped the delicate pink device around his chest, hooking it in the back. She reached into a drawer of the vanity and produced a pair of false tits. Alan gasped, “Please, Violet, hasn’t this gone far enough?”

“Your stepmother has directed this, and it will be done,” she replied, as she slipped the two pieces of foam into pockets in the cups of the bra. She made sure they were arranged properly and stepped back. “Hmm, I’d say 32-B, just the right size and shape for a sissy your age. As you grow older, we may make them a bit bigger! Now, your school clothes…..” She handed Alan a tight-fitting t-shirt that clung to his bust, outlining the shape, and making the bra straps and back quite obvious. His trousers were a pair of stretch jeans with hems above his ankles, so that the sheer nylon socks he wore were evident. “Go to Ma’am’s room and let her see what a prissy little thing we have made you into.”

The tight jeans restricted Alan’s stride to a ladylike mince as he went to his stepmother’s boudoir. As usual, she was sitting in bed in her revealing negligee and she smiled as Alan entered. “How delightful you look, darling,” she cried. “Come closer.” Alan approached her bed. She reached out and gently stroked his faux breasts and then let her hand stray to the bulge at his crotch, feeling it twitch as she ran her hand over it. “Yes, all the expected reactions!”

She summoned Violet. “Master Alan is ready for school….and we have preparations to make for tomorrow!”

Tuesday, April 30, 2024

Five Days to Sissy

TUESDAY

The next morning, Alan woke up to find another pair of panties on his dresser, and another note: “Put these on and them come to Ma’am’s dressing room.” The new scanties were even frillier than Monday’s pair, with a big bow on the front and three rows of ruffles across the back. Shrugging in resignation, Alan pulled them into place and again felt his cock rise in response. He padded down the corridor in bare feet to his stepmother’s dressing room.

On entering, he found Violet standing by the vanity. She motioned to the delicate chair before it and said, “Have a seat,” as she turned the chair so that it faced away from the mirror. Apprehensive, Alan obeyed, wondering what was next in his stepmother’s plans. He looked over the array of jars and bottles and brushes on the vanity. “Yes, Master Alan, those are all for you!” Violet said.

She picked a bottle of liquid foundation. “This is the right shade for your complexion. Now close your eyes while I apply it.” With a small sponge, she wiped his entire face and blended it in carefully. When she was done, she lifted his chin with one hand and turned his face in both directions. “Yes! It’s a good choice.” She brushed his bangs back to observe his eyebrows. “Fortunately, your brows are in good shape—we won’t need to pluck them, for now.”

Violet searched among the cosmetics and found the eyeshadow, in a deep shade of pink. She applied some of the color to a small brush. “Close your eyes and keep them closed until I say to open them,” she directed. Alan felt the feathery touch of the brush on first one eyelid, then the other. It tickled and he struggled to keep them closed as ordered. “Open your eyes,” the maid said. “Very pretty…but we’re not done.” She picked up the eyeliner. “Close them again,” she said, and stroked an even line of black just above his lashes. “Now, open them and look up.” This time she drew a line just above his lower lashes. Looking closely, she nodded.

Next was the mascara. “Open your eyes wide,” she directed. Alan felt the curved brush on his upper lashes, darkening and lengthening them. When Violet finished his eyelids felt heavier. She then moved to lightly coat his lower lashes as well. “How wide and beautiful they make your eyes seem, sweetie!”

The next stage was lipstick. “Open your mouth in an ‘O’,” she said and coated his lips with the sweet pink color. “Now, purse your lips as though you were kissing,” she ordered, and then applied a second coat. “Oh, lovely, pink and wet and so girly!” Violet exclaimed. “Are you finally done?” Alan asked.

“Not quite,” the maid answered. She picked up a wide brush and applied a soft pink to his cheeks. “There! The perfect embarrassed look for a humiliated sissy!” she declared. “Now, go get dressed for school!”
“School?” Alan asked, shocked. “I can’t go to school with my face painted like this!”

“You can and you will,” his stepmother announced from the doorway. “I’ve already cleared it with the administration. It seems you’re not the first sissy they’ve had as a student!”

Monday, April 29, 2024

Five Days to Sissy

MONDAY

Alan woke up and found a note on his dresser, beside a small pink box. “Your journey has begun. By Friday, you will have a new life” the note read. He opened the box and discovered a pair of panties—girl’s panties, pink, with ruffles and bows…and another note: “Strip to the skin, put on these panties and then come see me in my boudoir—Stepmother.”

In the six months since his father had remarried, Alan had learned it was useless to argue with his stepmother. She thoroughly dominated his father and was determined to do the same to Alan. Blushing all over, he did as instructed, and found that the feel of the silky panties on his bottom and genitals was quite pleasant…and more than a little arousing. He struggled to hide his erect cock as he walked down the corridor to his stepmother’s room. He knocked and waited for her to reply. “Do come in, Alan, dear,” she called.

As he entered, she sat up in her luxurious bed, wearing a negligee that did little to conceal her voluptuous form, which only increased Alan’s arousal. He walked in cautiously, careful to keep his hands over the bulge at his crotch. “Oh, stop it, Alan,” his stepmother scoffed. “I know perfectly well how those panties affect you. After all, you’ve been stealing mine for the past month!” Alan gasped and started to protest, but she simply continued. “You thought I didn’t know? Darling, nothing happens in this house I don’t know about. The laundress reported finding my scanties in your hamper weeks ago!”

She stretched languorously, which merely made her superb breasts more obvious. Reaching for a bell, she summoned her maid. “Violet, you will find a selection of underwear in the bottom drawer of my dresser. Pack them up and move them to the drawer where Master Alan keeps his underwear. You may dispose of those masculine items, as Alan will no longer need them.”

“Yes, ma’am,” the maid replied, tittering with laughter. Violet glanced at the young man, clad only in the frilly pink knickers. “I hope you keep Master Alan dressed just like this from now on,” she said, smiling.

“This is how Alan will dress each morning, Violet,” his stepmother answered. “I will direct you each day on the clothes to lay out for him…but he will remain in only panties until I have decided on his attire. For today, find the lavender shirt and the very tight jeans in his wardrobe and lay them on his bed.”

“Yes, ma’am,” the maid said, and exited, snickering.

“Really, Stepmother, “ Alan pleaded, “what will Father say when he comes home from his trip and finds me like this?”
“Nothing, dear,” she replied. “He already knows all about my plans for you—and more. Now, go get dressed…you’ll be late for school.”

Oh, god—school! Alan thought. How will I explain all this?

Saturday, April 20, 2024

Knick Knack, Paddlewhack

A Sissy Annie Story

It was a busy Saturday afternoon at the mall and, as Holly and Annie passed Build-A-Bear, Annie tugged on her Mommy’s arm, saying, “Please let’s go in…just to look around…please!”

Holly smiled and agreed, adding, “Yes, of course, but you must follow all the rules!”

“Oh, yes, Mommy, I will,” Annie replied and skipped into the store. There was a birthday party in progress, but the manager immediately recognized two of her best customers and came over to greet them.

“Hello, Ms. Holly,” she said, “How nice to see you! And you, Annie—how is my favorite little girl?”

“Oh, no, Miss,” Annie protested, “I am not a little girl; I am an obedient little sissy wanker!” She curtseyed and blushed, feeling her little nubbin twitch.

“My, my, you certainly are,” the manager agreed. Just then, Annie’s presence caught the attention of the little girls at the party and they and their mothers came over to meet her. Annie smiled and curtseyed to each of them, handing one of her cards to each of the lovely mothers. The ladies gathered around Holly, full of questions about her unusual charge, such as “My son is such a brat, could be successfully sissified?” or “My little boy always wants to try on his sister’s dresses—should I let him?”

Holly gave them advice and then Annie tugged at her arm again. “Mommy, come see the new plushie they have!” Holly excused herself and followed Annie to the display. It featured a four-foot-tall teddy, dressed in an elaborate ball gown. “Can we buy one, please, Mommy?” Annie looked at the price tag and blanched.

“Oh, I’m afraid not, honey, it’s much too expensive!” she explained. Annie began to plead and whine, behaving like a spoiled child, denied what she thinks is her due. Holly was having none of it, not in front of all these ladies and their daughters. She brought Annie to a chair, reached into her bag and produced the paddle. She laid Annie over her knees, pulled up the hem of her skirt to reveal her frilly ruffled panties and began to paddle her, right there before the whole store! The mothers smiled at seeing the sissy punished for the ill behavior, and the little girls laughed and giggled and pointed at Annie’s childish panties.

It wasn’t long before Annie was crying, kicking her legs and saying she was sorry. But Annie could also feel her humiliation growing and her nubbin getting stiff; as usual, such humiliation was arousing to her and only made her long for more of it. When Holly felt it had gone on long enough, she let the little sissy stand and face the group. Annie curtseyed and apologized, saying, “I am so sorry for interrupting your party this way, but I am just an obedient little sissy wanker and I can’t help it!”

The girls and their mothers applauded and Annie felt her humiliation and arousal rise again. “Mommy, may I show them my prissy sissy panties?” she asked.

“Yes, you may, dear,” Holly answered, and Annie proudly pulled up the front of her dress, so that the evidence of her arousal was visible to all.

After a few more minutes, the manager said, “I’m afraid it’s time for the party to end,” and girls and their mothers drifted off. She turned to Holly. “Thank you so much for the delightful entertainment! Give me your address and I will see that one of the new Princess Bears is sent to you, free of charge.”

Annie curtseyed once more to the manager and said, “Thank you, Miss…I am an obedient little sissy wanker!”

THE END

For more about Annie, click here.