Katie Ann - Chapter 9: Raggedy Ann and The Guard

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Katie Ann

Nineteen year old submissive Kathleen was sick of men that only wanted to be her master for sexual reasons, but when she responded to message from a gentleman on a matching site, she didn't realize how life-changing their relationship would be, and how right it would feel.

Becky Reus
Proofread By Jamie M


Chapter Nine: Raggedy Ann and The Guard

Kathleen rolled over and tried to figure out where she was, why she couldn’t extend her hands, and what was weird feeling on her chest and bum hole. As the sleep butterflies slowly disappeared, she remembered that she was Buttercup, with her Owner for the first time, wearing a kitten outfit at a BDSM resort. Her chest felt weird because it was flat, her small breasts were binded. As for her bum hole, that was because of the evil wretched tail. She really didn’t mind this outfit, truthfully she thought she looked cute in it when she caught glimpses of herself in brass work in the room yesterday. Yep, she didn’t mind this outfit … EXCEPT… that bloody tail, that she hated with a passion.

Last thing she remember was being petted by Owner in the suite proper, not being in this room which looked like a bedroom. She must of fallen fast asleep, so asleep that she couldn’t be woken up. She had a bad habit of doing that. He must of carried her to bed last night, when he went to bed himself.

Looking at the clock across the room, she noticed that it was barely after four in the morning. She tried to fall back asleep after curling back in a ball in her cat bed on top of the same bed that apparently Owner was also sleeping in, listening to his soft breathing.

Buttercup was trying to chase a butterfly in the midst of flowers in her dreams when she felt her ears being scratched. She looked around for the person distracting her from her flying target, so she could stick her claws in them, but it was just her and her butterfly. She felt her ears being scratched again as she batted for the butterfly. She puzzled over the scratching sensation, when it was just her and the butterfly. “Poof” went the butterfly when she realized the scratching was Owner trying to wake her up. Stretching, she made a purring sound as she rubbed the sleep out of her eyes.

“Good morning my kitty,” she was told as he petted her. Picking her up, he carried her to the bathroom. Sitting her down on the floor, she saw the collars being removed, and sound of the zip tie being cut.

After her wrists were untied, she was helped out of the the cat outfit. Then he finally took her wretched tail out. Breathing a sigh of relief, that didn’t last long, “MEOW MEOW MEOW,” she went as she put her hands on the throne.

Allowing her to do her business, he pointed out that she isn’t a cat anymore. Owner said that she is allowed to use words, but finished with these suspicious words, “at least ‘til I get you dressed again.” Stepping out of the room to give her privacy, he returned when she said she was done. Picking her up, she was laid down on a white pad on the bed. He then proceeded to give her a damp sponge bath, after stopping to remove the masks from her face.

Staring at the ceiling while he was doing her legs, she felt him stop, and get something that sounded like it was wrapped in plastic. Her legs were than grabbed, and something thicker was put under her bum.

“It is a snow storm,” he said in a silly tone.

Looking to him, she noticed he was putting powder on her bottom. POWDER?!?! “He isn’t diapering me, is he?” she thought. Straining to see what that thick pad was, she confirmed exactly what she thought it was. She was going to be diapered.

Before she could react, that diaper was closed and around her bottom. Patting it, he told her to stay put while he got her clothes for today.

After helping her put her feet in to what looked to be another one piece outfit, he fed her fisted hands in the arms. Her left arm was exactly like the kitty outfit, the hand was only attached on the bottom, so her resort ID band was out in the open. After making sure her hands were in fists in the onesie hands, he tied the hidden ribbons locking her fists in. Pulling the head piece up from her still flat chest, she noticed the top of the outfit was a mesh like material so her hair was clearly visible.

As he was zipping her up she took stock of the outfit. Other than her legs, which were striped red and white, the rest of it was just a nude fabric color. It hugged her skin, and it really showed off her padding. Though the outfit had thick hands, most of them was just stuffing, her real hands were in the palms in fists. She was a bit confused what she was, she needed more details.

Helping her to stand next to the bed, he dropped a blue long sleeve dress over her head before buttoning her up the back. While he placed a white apron on the front of her, she thought she might be Alice or Raggedy Ann, though probably the latter with her legs.

She was helped in to a pair of black shiny Mary Janes. She felt they were tighter than normal, but not too tight, then she remembered that Tiffany took accurate measurements of her, and didn’t write what Buttercup normally wore down.

As he was setting a red yarn wig on her head, they heard the room door bell ring. After he left to deal with it, she took the chance to look at herself in a reflective room decoration. She was definitely Raggedy Ann, she thought it looked good. though her wig was crooked, and she currently had no face, though she was sure neither of those would stay like that long.

“Let’s finish getting my doll dressed so we can eat before our breakfast gets cold.”

Fixing the wig, he started to attach it to yesterday’s braid with bobby pins.

Leading her out in the main room, she was sat by the table, which had some covered plates on it. He then started to slowly paint her face. He started to slowly paint her nose with a red triangle before painting muted red circles on her cheeks. Still staying with the red face paint, he painted her lips just in the center. Watching him switch to brown makeup pencil, she felt him tapping above her upper lip, as if she was getting freckles. Finally she saw him picking up a black pencil and he gave her lashes, before extending her lips.

After cleaning up his mess, he uncovered the breakfast. Apparently her breakfast today was two pancakes and a sippy cup of unknown liquid. He had bacon, sausage. eggs, hash browns, biscuits, and what looked like sausage gravy, with a cup of coffee. She couldn’t even dream of eating that much food.

Putting syrup on her pancakes, he began to feed her, between bites of his own, while giving her instructions on her character.

In his presence, or in this hotel room, she was a doll, she didn’t move a muscle herself, he would move her where he wanted her, unless he was holding her hand then she was to walk alongside of him. At no time was she supposed to talk as a doll, unless it was an emergency, or it was an hotel staff demanding information.

Both breakfasts gone, and the cups empty, he softly cleaned her face so the repairs were minimal. Repairs done, he carried her to the couch, and cuddle up to her while he watched television.


Buttercup the doll was kind of watching the television from the corner of her eye, she wasn’t supposed to turn her head towards it. She was instructed to keep whatever position Owner set her in when she was in this outfit. Right now it was sideways in the couch, leaning against him, with her arms crossed. There was nothing interesting on the telly anyways, he was watching some sports game. She would make a gagging motion and/or a sound, but both of those probably would get her in trouble. It had to be almost over, she heard the announcer say something about seconds on the clock in the fourth quarter. She thought he started watching it in the pre game, so she must of been sitting here in this same position for hours.

She heard what sounded like his PDA going off, and in order to get to the pocket it was in, he folded her up, placing her head near her feet. She hoped she didn’t stay in this position for long. It wasn’t painful right now, but she could see it getting more uncomfortable as time went along.

She felt him getting up, before noticing him coming towards her in the corner of her eye. He set about helping her up on her feet, before grabbing her hand, and walking towards the door. Walking along sided him as he instructed earlier, she was told, “I have a couple hours meeting today, we will get lunch first then I will leave you in the VIP Lounge while I have the meeting, You are free to walk around while I am gone.”

Going in the hall, she could see that decoration for this part of the hotel reminded her of a daycare, one designed with adult sized people in mind. Going through a set of doors, at the end of the hall, the difference was huge. One side of the doors was a daycare, the other side was an expensive five star resort. Looking through the balcony bars at the lobby below, she appeared to be on the third floor.

After a short ride down to main floor, he lead her into a small restaurant off from it. He helped her in a chair before sitting down himself.

They had been barely sat down long when Buttercup heard behind her, “What can I get you two?”

“She will have a grilled cheese and Iced Tea from your Littles menu, and I will have a french dip with a coke to drink. Please place it on my tab.”

The mysterious voice, acknowledged the order, and then disappeared. Buttercup noticed that couple at the next table were dressed as Tinkerbell and Peter Pan. Owner must of noticed her eye movement, because he addressed her, “This resort has an huge wardrobe available for guests use, unfortunately, none of them are Buttercup’s size, being an actual children’s size. This outfit and the kitten one were custom made for you.”

It couldn’t have been five minutes before a grilled cheese sandwich with apple slices, and a sippy cup was set in front of her. Owner promptly set to making sure she was well fed, and bringing the sippy cup to her lips.

Grabbing her hands, he had her place them on each side of the sippy cup on the edge of the table, before moving them to her mouth, so she was holding her own sippy cup in her mouth. Taking that as a hint, she drank her own iced tea.

She could see that he didn’t touch his sandwich until her food was all fed to her, then he started eating himself. After he was done, he helped her up, and grabbing her hand again, she was led out of the restaurant, briefly stopping to grab a refill of her sippy cup. Going through more corridors, he paused briefly to enter a code at a door, before leading both of them through it. Buttercup thought this wing looked even more expensive.

“Sir Adam, welcome to the VIP lounge.”

“Thank you, I will be leaving my submissive here for a few hours while I deal with resort business,” Owner replied to the lady wearing a french maid outfit.

“She over 18? Let’s check her in.”

After letting the lady know that she was indeed over eighteen, he gently moved Buttercup’s left arm towards the lady. After the ID band was scanned, he led the rag doll in the room, after letting them know he wasn’t staying, she was drinking Ice Tea, and she is not allowed to drink alcohol.

Raggedy Kath just dropped her mouth, after she was led into a combination library, bar, comfortable lounge, and computer lab. Owner told her she was free to move around, before leaving her.

First thing the rag doll did was go to the book shelves to see if any books caught her eye. One that caught her eye was ‘Gone with the Wind’. Which promptly reminded her she didn’t actually have hands when she tried to take it off the shelve.

Going to a stack of magazines she found one labeled Reminisce, she somehow managed to get it to where she left her sippy cup.

She was on her third Reminisce, and was, by now, becoming quite good at turning the pages with her covered fists. The lady who checked her in made sure her sippy cup was never near empty either.

She heard raised voices over her, she looked up and it was a security guard and the lady in the french maid outfit. They appear to be discussing her, specifically her age.

“Young girl, how old are you?” the guard demanded as he noticed she looking.

“19, born in March of 87,” she replied holding her ID band up for view.

The guard seeing the ID band, scanned it, and started to quiz her stuff off her driver’s license. Satisfied with the answers, he left the room to continue his rounds.

The lady just meekly apologize for her distraction, offering treats and complimentary items for her to excuse the experience.

She knew she wasn’t really supposed to talk, but the lady demanded an answer. The rag doll answered, “I don’t have the freedom to accept those, please offer them to my Owner when he picks me up.”

Realizing that was the best the lady was going to get, she left the little girl.

Next time Buttercup looked up from her magazine, she found not only was her sippy cup refilled, but she had two chocolate chip cookies next to it. Shaking her head, she just ate them, no need to upset the lady anymore.


Feeling a tap on her shoulder, Buttercup jumped, looking up from her tenth magazine, she really enjoyed these. It was Owner, there to pick her up from the lounge.

“I understand you had a little incident. I am happy how you handled it. You just saved me some money for tomorrow, not that is a problem, but it is always nice to have comps,” Owner praised her for earlier.

Nodding, and blushing as red as her painted cheeks, she handed owner her sippy cup, before going to put the magazine away. She heard, “Katie Ann, I will put that away.” When she turned toward the voice, she found it was the french maid lady.

After handing the maid the Reminisce, she offered Owner her hand.

He led her back to the lobby, and what looked like a seafood restaurant. She heard him check in for a reservation. Soon after they were being led to a booth, where she was made to go in first, then he got in after her on the same side.

“Can I have your Littles Menu? She will have an Ice Tea in this sippy cup, and I will have an Chardonnay.”

After the other menu was dropped off, she noticed that he was looking at both, and scratching his chin.

“How big are your Littles portions?” He asked the waitress when she came to the table.

After being informed that Littles menu was designed for adult appetites, he ordered, “In that case, I will have your surf and turf with a baked potato and your green beans, and she will have your lobster tail on a bed of rice with carrots.”

Soon after the waitress left, a basket of crab cakes was placed on the table. He looked at the little rag doll and said, “I give you permission to move and talk now, Kathleen,” after setting a crab cake and her drink within her reach.

Realizing her full first name basically him ordering her to be an adult, and come out of any character she was, she went meekly, “Yes, Owner? Sir?”

She was then quizzed on her weekend so far, if she was enjoying the relationship, the outfits, if it was what she thought it was going to be.

She was enjoying most everything, to the surprise of herself,, and loved the outfits. “Except for that bloody wretched tail,” she pointed out. She didn’t have a realistic vision of what a real life sub was, she admitted that.

He just chuckled at her about the tail, before informing her that she was being tested these last two days. He had another plan for her, something other than a cat or a doll. “Don’t get me wrong, this weekend isn’t the last time you are going to see either of them, including that tail, but I have another lifestyle planned for you. How about your chest?”

Kath expresses clueless about what Owner meant by her chest.

“Your binder?”

“Oh, I haven’t even felt it for most of today, true to your word. I didn’t notice it once I got used to it. It felt different and uncomfortable yesterday, not painful. Once I got used to it, I stopped noticing it,” she answered.

Happy with her answers she was told, “Buttercup, you free to move, but no more talking.”

The waitress used that cue to place their meals down, almost like she was waiting off stage for a cue. Owner set to work feeding both her and himself their meals. She enjoyed the lobster, something she hadn’t really had before.

After their meals were done -or in the rag doll’s case, was full- the two of them went back to the room. She had a doggy bag with her leftovers and sippy cup around her wrist on the side that isn’t holding Owner’s hand.

After taking care of her food, and changing her bottom, she was led back to the couch. She watched him put a DVD in the player. When it came up she could only silently giggle at the fact it was a Raggedy Ann disk. Cuddling in to Owner, she sat to watch herself on the telly


Author's Note: I am going to be on vacation the next two Saturdays with another couple, which includes my proofreader. Depending on available time, posting schedule maybe interrupted. Comments and questions are always welcomed -- Thanks Becky

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