fiction by Pretty Sissy Dani
“Hello, Darlings!”
The three little girls heard the voice from the doorway and responded, “It’s Nanny Katy!” Becky, the boldest of them, immediately asked, “Did you bring Sissy Annie?”
Stepping aside to reveal her companion, Nanny Katy said, “Of course, I did!” Sissy Annie came forward and made a dainty curtsey. Annie is a physically and chronologically adult male, but one who dresses and behaves like a four-year-old girl…to the point that she is legally a minor, under the control of her “mother” Michelle, Nanny Katy, her babysitter Jenny, and her psychologist, Dr. Dotson. Annie is happy to be a pretty sissy, with all that comes with that role.
The three members of the playgroup, Becky, Amy, and Liz, jumped to their feet and surrounded their playmate, hugging and kissing her. But Nanny Katy interrupted their greeting. “Girls, I’m afraid Annie was somewhat naughty on our way here,” she explained. “Annie fought against being put in her car seat…and she deserves a punishment!”
“Oh,” Amy gasped. “Is she going to get a paddling?”
“Yes, indeed,” Katy replied. “And one of you will get to do it!” Immediately, the girls began clamoring to be the chosen one. Katy reached into her carry-all and took out the “Prissy Pansy Paddlewhack” and handed it to Liz. “I believe it’s your turn, dear.” Then she turned her attention to Annie and spoke harshly. “Assume the position, Sissy Annie!”
With a whimper, Annie replied, “Y—yes, Nanny,” and bent over with her bottom high in the air and her hands grasping her ankles. Liz flipped Annie’s skirt and petticoats up to expose her bottom, covered in the pink satin of her panties. She smoothed the fabric with her hand as Nanny Katy said, “Remember, Sissy Annie, you must count every whack on your bottom!” Liz drew back her arm and swatted Annie’s rear.
“One,” Annie gasped through tears.
“Not bad, Liz,” Katy commented. “But I think she could handle it a bit harder.” Liz tried again, with more force.
“Two.”
Katy observed Annie’s face, streaked with tears and red with embarrassment. “Hold still, little sissy,” she advised, “or I’ll give Liz permission for more than the required five swats!” Liz hit her again.
“Three,” as Annie stumbled a bit from the force of the blow. Liz was getting into a rhythm now.
“Four.” Annie’s voice was weak from the anguish (and, secretly, from her arousal). Liz steadied herself for the final swat.
“Five,” Annie wailed.
“Very good, Liz, “ Katy said. She took out some ointment. “Go into the other room and rub this into Annie’s sore bottom, dear.”
While they were gone, Nanny Katy took out some paper and crayons and arranged them on a table. When Liz and Sissy Annie returned, she said, “Why don’t you all sit down and make some pretty drawings to show your mommies?” The three little girls joined their sissy friend at the table and began work on the drawings. Katy walked around, commenting on the work, offering suggestions, and praising how nicely they all drew. After a short time, she had each of them display their finished artwork.
Amy had done a lovely scene of all four friends in a circle with their dollies. But Becky and Liz had done pretty portraits of Sissy Annie—Liz’s showed Annie doing a curtsey, as she had when she arrived; Becky, though, drew Annie lifting her skirt and petticoats, to show off her pretty sissy panties! Katy applauded their work, noting that Annie blushed furiously at being so exposed.
“What about your drawing, Annie?” Katy asked. Annie shyly held up her paper, which depicted Annie surrounded by her plushies, with a big pink paci in her mouth. The girls giggled and smiled. “It’s Baby Annie,” Amy said.
“Yes,” Katy agreed. “That’s how she often looks when she takes her sissy nap in the afternoon.” Just at that moment, a chime sounded from Nanny Katy’s phone. “Oh dear, it’s time for Annie’s afternoon wanking! Would you girls like to watch?”
The trio of girls laughed. “We’d love to,” Becky spoke up.
“Wonderful!” Katy said. “Annie, you know what to do.” Annie climbed up on the little bed, raised her skirt and pettis, and spread her legs wide. Katy produced a tiny key from her purse. “First we have to take our sissy out of her chastity,” she explained. She lowered Annie’s panties, revealing her tiny nubbin locked in a pink plastic container. She used the key and Annie’s nubbin grew stiff.
“Ooooh,” Becky exclaimed, “she must be excited already!”
“Of course, she is,” Katy replied. “Annie knows how delightful her wanking feels, especially when it happens with people observing. It makes her feel so sissy-ish and humiliated—and that always makes her feel really submissive and girly!”
With that, Katy began lightly stroking and rubbing Annie’s nubbin. As she did, Annie lay back and closed her eyes, sighing in pleasure. Katy could feel the arousal reaching a peak. “Becky, go in my carry-all and get me Annie’s sippy-cup, please.” Becky handed her the cup, already partly filled with warm milk. Katy snapped off the top and positioned it near te tip of Annie’s nubbin, just as the first spurt of her cream happened. Katy continued the stimulation until Annie had spurted four times, catching all the cream in her cup.
She took a towel and cleaned up the nubbin, then locked the pink chastity device back in place. She covered the cup again and shook it to mix the sissy cream with the milk. “Sit up, Annie,” she said, “and drink up.” Annie took the cup and sipped from it. “Mmmmm, that’s delicious,” Annie sighed.
“She likes the taste?” Amy asked.
“Of course.” Katy answered. “To her it tastes just like melted vanilla ice cream…sweet and sticky!”
As she fed the sweet mixture to Annie, Nanny Katy noticed someone watching from the doorway. “Who is that?” she asked.
“Oh, gosh,” Amy said. “That’s my big brother, Paul!” She shouted at the intruder. “Paulie, you know Mumsy said not to disturb us!”
“It’s all right, Amy,” Katy said. “I’m sure Paulie is simply intrigued by Sissy Annie.”
“I bet he is,” Amy replied, in a whisper. “He probably is wearing panties right now—Mumsy’s panties!”
Kary laughed. “Really? Is your brother a sissy?”
“Not like Annie,” Amy said. “But I know he steals panties and other frillies!”
Katy beckoned to the teen-aged boy. “Come here, Paulie.” He tentatively approached Nanny Katy…and when he was close enough, she reached up and pulled down his trousers—revealing a pretty pair of lace-trimmed silk panties.
The girls, including Annie, exploded in laughter. “Oh, Paulie, your secret is out,” Amy said. “Nanny Katy, can we make him more like Annie?”
“We certainly can, dear,” Katy answered. “Bring me my carry-all.” She went into the bag and pulled out a make-up kit. “Here’s an idea—why don’t we let Annie do his face?”
“Oh, goodie!” Annie exclaimed. “I’ll make him look sweet and pretty!” Paul shuddered and cowered at those words, but inwardly, he reveled at the idea of being closer to the pretty sissy and becoming more girlish.
“Now, sit still, Paulie,” Katy advised, “or you’ll mess everything up!” Annie picked up the foundation and carefully smoothed it all over Paul’s face, evening out his complexion. Then she turned to Katy and asked, “Nanny, shall I use the same colors you and Mommy use on me?”
“Yes, I think so, darling,” the nanny responded. “Those soft pinks are perfect for a sissy!” Annie took the pink eyeshadow and applied it to his lids. Then she got the eyelash curler and pressed it to his already long lashes. That was followed with eyeliner and mascara. “Look up, Paulie,” she directed, as she brushed the dark color on his lower lashes, making his eyes seem bigger and better defined.
Next she took the blush in hand and dusted it on his cheeks, giving them a soft glow of embarrassment, suited to a feminized boy. The last step was a dark pink lipstick that made his mouth look pouty, especially after she added the gloss that gave his lips a delicate sheen. She stepped back to let the others see her work. “Did I do a good job, Nanny?” she asked.
“Yes, Indeed, Annie,” Katy replied. “Oh, yes,” Amy gushed. “You’ve turned my horrid big brother into a beautiful dolly!” And the other girls applauded their agreement.
“What can we dress him in?” asked Liz. “He can’t go around in just panties!”
“Of course not,” Katy agreed. “Hmmm…there’s an outfit in my carry-all. I had brought it for Annie to change into later, but it should fit Paulie.” She took it out and displayed it for them. The three girls oohed and aahed. It was a pink sissy dress, covered in lace and ruffles, with a skirt that ended inches above Paul’s knees once she placed it on him. “What about shoes? “ Becky inquired.
“I have a pretty pair of pink patent-leather pumps with kitten heels,” Amy suggested. “Let me go get them.” She returned in moments and buckled them onto his feet. Katy produced a pair of tiny padlocks to secure them.
The finishing touches were glittering earrings, a collar with a heart pendant, and—last but not least—an enormous bow attached to his still short and boyish hair. “Now, that is truly a sissy,” Katy declared. Then they heard a voice from downstairs:
“Amy, I’m home!”
“It’s Mumsy,” Amy gasped. “What will she think when she sees what we’ve done to Paulie?”
The answer came when Amy and Paul’s mother entered. “Mrs. Robinson,” Nanny Katy proclaimed, “may I introduce your femboy, ‘Polly’?”
Mrs. Robinson sighed, “Oh, my, I’ve been waiting and hoping you would take him under your care and sissify him completely, Nanny Katy!” Then she took her new sissy boy in her arms and kissed him.
THE END
