Sydney's request

Carson sat on the couch in the living room of his mansion in the mid-afternoon. He was looking over the report from Josslyn’s pony trainer, Stable Mistress Stephanie. As usual, the report praised Buttercup for her behavior and skill. He glanced down from the paper to where Kennedy lay with her head resting in his lap as she watched a true crime investigation show on TV. He reached down with his left hand and gently ran it through her long blonde hair. “Your sister did very well during her pony training again,” he said as he gently tossed the paper onto the low-sitting but large dark wood coffee table in front of the couch.

Kennedy smiled as she watched it slowly fall, almost perfectly into place atop the daily report from Monica’s puppy training. “That doesn’t surprise me,” she said as she shifted to look up at Carson. “She really likes her pony training.”

“I’ll say,” Carson said with a laugh as the sound of footsteps filled the air, along with the faint pop of a flip-flop gently slapping the feet of whoever wore them after each step. Sydney stepped into the room, dressed in a black string bikini that flaunted her body. Her skin looked to be gently sun-kissed, and her long red hair was still slightly damp from her recent swim. She made her way to the couch and knelt next to it.

“Master, may I ask you something?”

“Of course, Sydney.”

“Master, may I please have some little time?”

Carson turned his attention to the beautiful eighteen-year-old redhead had a hopeful look on her face. He smiled at her and then rubbed his chin in thought. “I suppose it has been a while since I’ve let you be your little self. So here’s what we’ll do: we’re going to the club tomorrow and we’ll be staying until Sunday. From now until we get back, you will be little Sydney, only breaking character and not wearing childish clothes when we are in public.”

“Thank you, Daddy! That would be wonderful!” Sydney said excitedly, quickly adopting her little voice.

“Go find Nanny Jessica and see if she’ll help you get dressed.”

“I know where she is, Daddy. She was reading by the pool when I was swimming,” Sydney said before quickly leaving the room. Carson couldn’t help but smile at the redhead’s eagerness. He then looked down at Kennedy, who still lay with her head in his lap.

“If you’re open to it, Kennedy, I’d like you to spend some time this weekend in the daycare at the club,” he said as he looked down at the beautiful blonde.

“Jessica has spoken to me about it several times since our last visit to the club,” Kennedy said as she sat up and then turned to face him. “I’m open to it, as Jessica has pointed out several times to me now, several alpha slaves go through at least a little bit of nanny training. Besides, you’ve already had me babysit her as her little self once,” she added with a slight shrug of her shoulders.

“And with you being a bit more knowledgeable of, I don’t know what to call it, Little Psychology? Little Space? Either way, it does give me more options for punishment for the other girls. I know you and Josslyn enjoyed it the one time I had you as littles, but something tells me Ellie won’t strictly enjoy it, and I don’t know how Monica feels about it.”

“She would have had a rotation as a little during her training at the club, but yeah, she’s never spoken to me about it, and I haven’t asked.”

As Carson and Kennedy discussed the training for the upcoming weekend, Sydney made her way back to the pool and saw the brunette sitting in a lounger, reading her book and sipping on a glass of green juice. Instead of the typical long light green dress and white apron, she was dressed in a white tank top, denim shorts, and a pair of dark brown strappy sandals.

“Excuse me, Nanny Jessica,” Sydney said as she came to a stop next to the lounger. Hearing Sydney use her “little” voice and refer to her as “Nanny Jessica” and not simply “Jessica” immediately caught her attention. She quickly marked her place in her book and turned her head to look at the beautiful eighteen-year-old submissive.

“Yes, my precious girl,” she replied, her tone taking on a sweet and soothing tone that carried an undertone of authority.

“I asked Daddy if I could have some little time, and he sent me to find you so you could help me get dressed.”

Nanny Jessica rose from the lounger with a smile on her face. She tucked her book under one arm and held out her hand to Sydney. “Come on, little one, let’s go get you dressed.”

“Thank you, Nanny Jessica!” Sydney said excitedly as she took the brunette’s hand. She followed the other woman into the mansion, still holding her hand, and up to the bedroom that had been decorated like a little girl’s bedroom.

“Okay, first, we have to lose this,” Nanny Jessica said as she untied the strings that held the flimsy bikini in place against Sydney’s body. The swimwear fell to the floor only to be quickly scooped up by the other woman, taken into the bathroom, and tossed into the hamper. When she returned, she made her way to the dresser and opened the top drawer. First, she pulled out a pink frilly bra, then a pair of pink panties. “Last time I stopped and got some little supplies, I got you a new pair of panties. I’m sure your daddy will love seeing you in them. What do you think?” she asked as she held them up in both hands for Sydney to see. The panties were small and on the front in white lettering with bold red edging were the words “I” and “Daddy” with a big red heart emoji between them. Nanny Jessica turned the panties over, allowing Sydney to see the back, and showing her that the panties were a thong.

“Daddy will love those! I know how much he likes panties that let him see a girl’s bare bottom.”

“Come here, sweetie, and Nanny Jessica will help you into them.”

“Yes, Nanny Jessica,” Sydney said as she made her way to her nanny. Nanny Jessica knelt and laughed.

“Your silly nanny forgot to get these off your feet,” she said as she easily slipped Sydney’s feet free of the flip-flops. She then held out the panties so Sydney could step into them. Not waiting to be told, Sydney stepped into the panties and allowed the other woman to pull them up. Without a word, Nanny Jessica stood and helped the teen into the frilly pink bra before moving her in front of the full-length mirror. “Look how cute you look.”

Sydney smiled as she looked at herself in the mirror before she spun around and looked over her shoulder, admiring how she looked from behind. “I love my new panties! Thank you so, so much, Nanny Jessica. Don’t they make my bottom look cute?”

“You’re welcome, sweet girl, and yes, you have a very cute bottom. Now let’s finish getting you dressed.

“Yes, please, Nanny Jessica.” It didn’t take long for Nanny Jessica to finish dressing Sydney in pink knee-high socks with white lace frills at the top, a pair of black Mary Jane shoes, and a white dress with pink lace frills at the bottom. The last step was to take Sydney into the bathroom, where she blow-dried the last of the dampness from her long red hair before meticulously brushing it.

“Ponytail?” Nanny Jessica asked as she held Sydney’s hair in a loose ponytail for her to see in the mirror. “Or pigtails?” she asked before holding the redhead’s hair in loose pigtails.

“Pigtails, please, Nanny Jessica.”

“Such a polite little girl you are,” Nanny Jessica said before softly kissing Sydney’s cheek. She then quickly put her long hair into pigtails, using small hair ties to hold them in place, then decorating each pigtail with a small white ribbon, tied near the base of each pigtail. “Alright, let’s go find your daddy and show him how you’re dressed.”

The pair walked hand in hand downstairs, looking for Carson. The first ones they found were Ellie and Monica. The two brunettes were in the well-equipped home gym, riding a pair of stationary bikes at full speed, their bodies covered in a sheen of sweat.

“Well, don’t you look cute?” Ellie asked with a smile, not slowing for a second.

“I love your little ribbons,” Monica said with a smile of her own.

“Thank you, Ellie, thank you, Monica. Have you seen my daddy?”

“No, sweetie, but I’m sure he’s around somewhere,” Ellie answered.

“He’s up in his office,” Kennedy said as she walked into the room. She was now dressed in a black sports bra, tight-fitting black yoga pants, and white sneakers. She set a machine that would allow her to do leg curls at 80 lbs to start, and lie on the bench with her legs under the cross bar. “I’m sure he’d love to see how cute you look,” she added as she curled her legs until her heels touched her ass, pulling the weight up as she did so.

“Thank you, Miss Kennedy,” Sydney said as she and Nanny Jessica left the room. They went back upstairs and stopped in front of Carson’s office door. Nanny Jessica softly knocked on it.

“Come in,” they heard him say from inside. With her free hand, Sydney reached for the knob, turned it, and pushed the door open before excitedly bursting into the room.

“Hi, Daddy! Do you like how Nanny Jessica dressed me for you?” she asked, doing a quick twirl.

“I do, you look very cute.”

“How about the new panties, Nanny Jessica gave me?” She asked as she lifted her dress, revealing her panties. Without lowering her childish dress, she turned so Carson could see her from behind. “Do you like how they let you see my bare bottom, Daddy?”

“Yes, Sydney, you have a beautiful bottom,” he said as he rolled his chair back from the desk. “Come sit on Daddy’s lap.”

“Yes, Daddy,” she said with a smile as she let her dress fall back into place, made her way to him, and sat on his lap. He couldn’t help but admire how quickly and easily she slid into her little personality. Especially since only recently embracing it as part of her submission to him, and not overly enjoying her rotation as a little at the club before being assigned to him.

He slid his hand under her childish dress and began to gently rub her pussy through her panties. “Are you excited to get to spend a whole weekend at the club as my little girl, and to see all your little friends at the club’s daycare?”

“Yes, Daddy,” she said, her pitch going even higher to a slight whine of pleasure as she moved her hips on his lap while he continued to tease her with his skilled fingers.

“Miss Kennedy will be spending some time at the daycare with you. She’s going to be learning a little bit about being a nanny, like Nanny Jessica. Would you like that?”

“Yes, Daddy. Miss Kennedy is a good alpha ****, a good babysitter, and she’ll be a good nanny too,” she replied through quiet mewls of need.

“And you’re going to be a good girl all weekend, right?” he asked as he applied more pressure and focused on her clit.

“Yes, Daddy. I’ll be a good little girl. Your good little girl, so you’ll let me sleep in your bed, Daddy.” She was now struggling to stay still as he continued to tease her clit expertly through her panties. She could feel the muscles in her stomach tighten like an overwound coil.

“Don’t have your special feeling without Daddy’s permission,” he said as he looked over at Jessica, who stood in the door watching things play out. “Otherwise, Daddy will bend you over his desk, spank your bare bottom, and then have Nanny Jessica put you in diapers until morning. I might even have you sent to the daycare nursery when we get to the club,” he said in a gentle yet stern tone as he applied slightly more pressure to her clit as he continued to rub it.

“I’ll be right back,” Jessica said, seeing the writing on the wall as Sydney’s mewls grew louder and her hips moved more forcefully.

She went the short distance to the guestroom she stayed in and changed into her light green nanny dress and white apron before returning to Carson’s office. When she returned, she saw Kennedy’s twin sister, Josslyn, standing in the office watching what was happening.

“Please, Daddy!? Please, can your little girl have her special feeling!? Please, Daddy!? Please!? Please!? Please!” she said, her desperation growing more and more evident with each word.

“Not, yet, Daddy’s not ready for you to have your special feeling just yet,” he said, adding speed to his skillful manipulations.

Sydney gasped as she pressed her feet against Carson’s desk, her every muscle tight with need. “Oh Fffuuck! I’m sorry, Daddy!” she cried out, losing her little tone. A split second later, she moaned loudly as her forbidden orgasm burst free light a runaway train. “I’m sorry, Daddy. I’m so sorry,” she panted, and went back to using her little tone.

“Bad girl,” Carson said sternly. He lifted Sydney from his lap and bent the teen over his desk. As he did, she reached across and grabbed the far edge. He then lifted her childish dress and pulled down her thong. “Not only did you disobey me, but you also used a very naughty word. So, now Daddy is going to spank you as promised,” he said before looking over at Jessica. “Nanny Jessica, before diapering my naughty girl, would you be kind enough to make sure and wash that naughty word out of her mouth?”

“Of course, Mister Henning,” she replied with a smile. Sydney whimpered at the thought of having her mouth washed out with soap just before she felt the sharp sting of Carson’s hand on her bare ass.

Smack after smack landed on Sydney’s ass, quickly turning it bright red. With each smack, she whimpered and whined as she shifted on her feet, but remained obediently bent over the desk for her punishment. He continued to spank the beautiful redhead with increasing **** until tears streamed down her face and she sobbed quietly with her face pressed against his desk.

After one last hard smack, he pulled up her thong and helped her stand. “Go with Nanny Jessica,” he said sternly.

“Yes, Daddy,” she said as she wiped tears from her eyes and shuffled to the other woman.

“Come on, young lady,” Nanny Jessica said as she grabbed Sydney’s arm. “You need your mouth washed out,” she added as she led her out of Carson’s office and back into the bedroom that had been decorated as a little girl’s room, and then into the attached bathroom. “Hands on the back of your head, mouth open, and tongue out,” she said as she stood Sydney in front of the mirror.

Sydney whimpered as she obeyed and watched as Nanny Jessica turned on the cold tap at full blast and grabbed the dark green bar of soap from its place on the countertop. Nanny Jessica moved the soap under the water and rolled it in her hand, working up a thick sudsy lather. When she was satisfied with the state of the soap, she moved it to Sydney’s waiting mouth and began to scrub.

Sydney began to gag, and her eyes watered with fresh tears as soon as the bitter-tasting suds coated her tongue, leaving a filmy residue as the suds began to fall messily into the sink. Nanny Jessica continued to scrub until the suds surrounded her mouth, and tears once again streamed down her cheeks.

“Bite down, hold the soap right there, young lady,” Nanny Jessica said. “Now you stay just like that, I’ll be right back,” she added before leaving the room. She returned a few minutes later with a chilish sippy cup. “Are you going to use that naughty word again, young lady?” she asked as she stood next to Sydney, not looking at her, but rather her reflection in the mirror.

“Uh-uh, Anny Eshica,” Sydney grunted through the bar of soap she still held in her mouth.

“I should hope not,” Nanny Jessica said, taking the soap from her mouth and setting it back in its place by the sink. “Rinse,” she said as she handed Sydney the sippy cup. Sydney eagerly took it and sucked in some of the cold water it held before swishing it in her mouth before spitting it out. After several times, she finally got most of the foul taste of the soap out of her mouth.

“I’m sorry, Nanny Jessica,” she said as she set the sippy cup down.

“I know, now come on,” she said, taking Syndy by the arm again. This time, she led her back into the little girl’s room and got her out of her childish dress, shoes, socks, bra, and panties before taking her over to the changing table, completely naked. Syney’s eyes darted to the pink frilly diaper that awaited her on the changing table.

When nanny Jessica pat the changing table, Sydney climbed onto it, hissing slightly as her still-sore bottom made contact the the plush tabletop. With a smile on her face, Nanny Jessica eased Sydney back into a lying position with her hips and bottom perfectly over the diaper. She then grabbed a large container of baby powder and sprinkled a generous amount onto her pussy and the fronts of her thighs before lifting her legs and doing the same to her reddened backside. She then gently set Sydney’s legs down and closed the diaper in place.

With Sydney properly diapered, she re-dressed the teen in a yellow adult onesie and white booties before helping her off the changing table and leading her over to the wide rocking chair. Nanny Jessica sat in the chair and had Sydney sit sideways on her lap. “Okay, Sydney, it’s been a while since lunch, so you're probably hungry,” she said as she undid the snap above her right breast, causing the flap to fall away and expose her breast. “So, I’m going to feed you and put you down for a nap.”

Without hesitation, Sydney took Nanny Jessica’s nipple in her mouth and began to greedily suck. She was eager to have the sweet taste of Nanny Jessica’s breast milk wash away the last of the lingering bitter taste of the soap. She closed he eyes as she continued to suck as she relaxed in Janny Jessica’s lap and arms.

When she had had her fill, Nanny Jessica closed the flap and held up a pacifier that was between two white silk ribbons, one of the ribbons having two D-rings at its other end. “Here’s your binki baby,” she said sweetly before Sydney took the rubber nipple of the pacifier in her mouth. Nanny Jessica then wrapped the white silk ribbons around Sydney’s head, feeding the working end of the ribbon with no D-rings through both D-rings before folding over the second, and pulling it back through the first, cinching it tightly into place. “Now it’s naptime,” she said as she helped Sydney into the crib before raising the lowered side and locking it in place. She then made her way to the curtains and pulled them over the windows before returning to Sydney and placing a pink weighted blanket over her. “Sweet dreams,” she said in a sing-song tone as she shut off the light and left the room.

“This is going to be a fun weekend,” Sydney thought, as she gently sucked on the pacifier and relaxed, letting the warmth and security the weighted blanket gave her lull her into a restful sleep.

How will the weekend at the club begin? Answer in comments.

A) Kennedy's nanny training. Normal daycare route, little Sydney.

B) Kennedy's nanny training, Daycare nursery route, baby Sydney.

C) Monica in the puppy kennels

D) Josslyn continues her pony training.

E) something else. What?