This morning, Anna had realized that… she seemed to have rather childish taste in underwear. Of course before now, she had never thought anyone besides herself would get the chance to see them. She had just picked out what she thought was cute. But now that she knew there was a chance Jack would be… disciplining her, she was suddenly a lot more conscious about what she put on.

Most of her panties had little cats or other cute little animals on them, or were just very, very frilly. Today she had managed to find a pair of pink satin ones that she very much hoped she wouldn't have to reveal to him at some point. But going by the way he was skimming over the letter she'd typed up, it didn't look good.

"Not bad," Jack said looking up at her with a smirk. Anna tensed up as he set down the paper and then got up. "It was structured nicely, but there were about three typos."

Anna tensed. "Right, okay."

She stepped forward as Jack went to her side, and then bent forward slightly and put her hands on the desk. Three, it was only three. That wasn't so bad. She had gotten a dozen smacks earlier over her skirt, and Jack had told her next time it would be over her panties, and then on the bare. A pretty simple three strike rule. It was embarrassing to have to pull her skirt up again so soon after her first spanking, but at least it was only three.

Jack grabbed the back of her skirt, and Anna's face turned red as he slowly peeled it up, revealing her panties. Jack soaked in her expression. "No cute animals today?" he asked, amused.

Anna's cheeks flushed even deeper. "N-no sir. Yesterday was just… I mean I don't-"

Jack cut her off again. "Well, these are cute too," he said as he hand caressed her backside. Anna squeaked as he gave it a little squeeze. "I think cute suits you. Of course that's just my opinion. If you like them and they're your taste, why change them for me?" he asked, his breath tickling her ear.

She felt like she was going to melt. "I'll keep that in mind sir…" Maybe she didn't need to buy new underwear after all. It wasn't like she wanted to show them off regularly, but… if it was going to be a thing and Jack liked them, what was the harm in it?

SMACK!

"Oh!"

Anna jumped when Jack's hand came down and smacked her right cheek. One of her feet kicked up, and her hands nearly left the desk, but she quickly resumed her position. Dang it, she had lost her focus again. "Oh, sir! That's not fair, I wasn't ready," she said pouting at him.

Jack chuckled. "Sorry Anna, but you have to keep on your toes. Now eyes front, two more." Anna gulped and looked forward again, bracing herself. She didn't know if it was because of her spanking a bit earlier, or if he was swinging a bit harder, but it seemed like that last smack stung a bit more.

SMACK!

"Uh!"

SMACK!

"Ouch!"

Anna hopped from foot to foot, biting her lip at the two stinging smacks that had landed on each cheek. She kept her hands down, and Jack nodded in approval. Last time she had jumped up before he'd said so, earning herself another smack. She was a quick learner. Both in her actual work, and when taking punishment. "You can stand up and rub now," he said.

She rose up, quickly reaching back and rubbing her butt. "Oh, I'm sorry sir. I promise the next one will be flawless." At least she hoped it was. She didn't want to show off her bare butt to him, and she certainly didn't want anymore spanking. She had no idea someone's hand could sting so much. Something like the paddle or cane must have been hellish in comparison.

"I'm sure you will. I believe in you. You're a bright girl Anna. Just remember, punishments might sting, but you'll be better for them."

Anna nodded shyly. Her backside certainly didn't feel better, but… well, she was motivated to make sure she didn't screw up in the future, so she supposed he had a point. "Thank you sir… is there anything else I can do for you?" she asked. Another task risked another punishment, but she didn't want to become a slacker. She wanted to show him she really was trying to do her best and improve.

Jack hummed. "Well, it's almost lunch time. Tell you what, why don't you grab us a little something from that Japanese place across the street," he said, pulling out wallet and handing her his card. "Go ahead and pick for me. I trust your taste."

Anna nodded excitedly. Getting lunch was something so simple there was no chance of making any mistakes. "Yes sir! I'll be right back!"

Jack watched as she scurried out, feeling happy about how his progress with Anna was coming along. She was a quick learner, both as an actual secretary, and when it came to punishment. She didn't put up very much of a fuss when it came to discipline, and it would only take steadily working her up to more strict implements like the paddle. For now though, he was content just smacking that cute little bottom of hers with his hand.

And as for her sister? Well, he was sure that the others would do their part to humble Elsa. Once they did, he would take over and start really training her properly alongside her sister. After all, with Anna under his thumb reigning Elsa in would be that much easier, and sweeter.

Plus he was growing genuinely fond of the girl. Perhaps he really would keep her around when this was over. By then she would probably have the actual skill set required for the job, and he was sure if it was under him Mr. Arendelle would let her continue on just to placate her.

And Elsa… well, he would have to wait and see.

Elsa had been surprised that her bottom seemed to be in fairly good condition. While she still felt tender, the balm she'd been given had worked wonders. To her surprise, Gogo had told her that it had been supplied to them by Jack and the other men in the office. Though Elsa suspected that it was hardly an act of kindness. Probably just them wanting to ensure their bottoms were in well enough condition for the next punishment.

She had considered not using it the next time she was punished. She knew as much as they liked spanking bottoms, they could only risk doing so much damage at one given time. But she had a feeling that she wouldn't be able to resist rubbing it across her cheeks the next time she found herself with a smoking hot bottom. And at this point she had accepted that there would indeed be a next time.

That didn't mean she wasn't going to do her damndest to avoid it though. She made sure to take every precaution she could during the coffee run this morning. Triple checking each order. The men seemed amused by the act, and she did her best to try and hide how much it irked her.

Nobody raised any complaints when she got back, but she was soon sent out yet again to pick up dry cleaning. On one hand, she was out of the dreaded office. On the other, she was annoyed to yet again be sent on another pointless task. When she got back, she was greeted with the sight of a familiar face.

"Please don't tell me Eugene wants to see me," she said, frowning as she looked towards Rapunzel.

The blonde quickly shushed her, looking around to make sure nobody else had heard her. "Be a bit more careful about using his real name. He told me that in confidence. If he hears you guys saying it he'll fry my butt," she said.

"He'll fry your butt either way from what I've seen," Elsa commented. Hiro might have been the most eager of Jack's little clique, but Flynn was hardly better.

She handled Rapunzel the dry cleaning, and the bubbly blonde smiled and nodded in appreciation. "Good timing. You were about a couple of minutes away from a butt blistering for being late," she said.

"Again, I can't see that not happening either way. Every one of the men in this office is trigger happy," she said matter-of-factly.

Rapunzel glanced around again, worried that someone might hear her. "Yeah, I know. But you have to play along. And maybe lower your voice a little when you're talking about them. Otherwise things go from bad to worse." Elsa honestly had no idea how things could possibly get worse around here, but she didn't want to find out. "Anyway, you don't have to worry about Flynn right now. It's Hiccup that wants to see you."

Elsa looked curious. "Did he say why?" she asked. Hiccup usually didn't bother her all that much. She didn't by any means like him. But off all of the men in the office he was rather tame. He wasn't above giving her a smack on the rear, and he certainly hadn't hid that he enjoyed her punishment. But he'd never called her to his office or gone out of his way to stifle her.

"He didn't, but be careful. He might not be the enthusiastic guy in the office, but he can be pretty nasty when it comes to punishments," Rapunzel warned, her hand making its way to her backside. As if she could feel the sting from her previous encounters with him flaring up again.

Elsa nodded. "Thanks for the head's up. I appreciate it. Try and stay out of trouble with Eugene," she joked, making sure to keep her voice down at the last part.

Rapunzel giggled. "Can't make any promises. Good luck."

The blonde left, and then Elsa began making her way to Hiccup's office. She stopped in front of his door, straightening her blouse and skirt out and trying to make sure not a single hair was out of place. She wasn't sure if he could actually punish her for an unkept uniform, and she didn't want to find out.

After making sure she was presentable, she reached up to knock on the door. Right before she could however, she heard a loud THWACK from the other side of the door, followed by a yelp. Elsa flinched, her eyes going wide. Was he punishing someone right now? Should… should she still go in? Should she come back?

She heard another THWACK and a girlish sequel, and she bit her lip. No, there was no leaving or waiting. She was sure this was some kind of test or something. He had called for her and then started punishing someone else to see if she would scare easily. Well, she wouldn't. She reached back up and knocked on the door. "Mr. Haddock, it's Elsa. you called for me?" she said.

THWACK!

Elsa flinched again, and for a moment she wondered if he heard her. But then his voice called out. "Come in." She hesitated for a moment, but then let out a breath and opened the door. When she entered, she saw Hiccup standing in front of his desk, smiling and holding a cane in his hand.

In front of him was a woman with long raven hair, who was bent over the desk with her skirt rolled up and her panties lowered down below her thighs. Elsa recognized her as Heather, someone who she hadn't really conversed with all that much, but sympathized with quite a bit at this moment.

This had been the first time Elsa had seen someone punished on their bare bottom, and even though she knew. There were three rather angry looking red lines across her cheeks, which already looked like they had a bit of color to them. Hiccup tapped her bottom with the cane. "You mind staying right there while I finish up with Heather?" he asked, not even turning to look at her.

She grit her teeth. Was he seriously going to make her stand here and watch this? Had this been the reason he had called her here? "Of course sir…" she muttered bitterly.

Hiccup brought his arm back, raising the cane in the air, and then swung. Elsa had wanted to look away. To deny him the satisfaction of knowing she was taking this horrible scene in. But she couldn't quite seem to bring herself to. She watched as the cane cut down across Heather's cheeks, landing right between where two strokes had already landed.

THWACK!

"OW!"

Heather gripped the desk tightly, her whole body locking up as the cane bounded off of her backside. Elsa couldn't keep herself from locking up either. Seeing Gogo get paddled had also been rattling, and experiencing it herself had only proven worst than she had imagined.

Seeing the cane brought a whole new terrible train of thought to her mind. It didn't cover as much surface area as the paddle, but it looked like it bit the spot it landed with a far sharper sting. She felt her stomach twist at the thought of having to bend over and be spanked with the whippy piece of wood.

THWACK!

The can landed again, this time lower than where the other strokes had.

"OH! OUCH!" One of Heather's legs kicked out, but she quickly got back into position, her heels clicking as she placed her feet apart and stuck her rear out. "I'm sorry sir!"

Hiccup tapped her bottoms with the cane again, lining up his next stroke. "You know better Heather. And with Elsa watching too. You're going to make a bad impression. Don't break position again," he warned.

"Yes sir! Sorry again sir!"

THWACK!

"OOOHHHH!"

The response to her apology came in the form of another crisp stroke of the cane, this time landing right between the curve of her bottom and the top of her thighs. She howled, bouncing up and down on her toes, but managed to stay over the desk. Hiccup smiled as she watched Heather struggle to maintain position.

Her legs were trembling slightly, and there were not six very red lines down across both of her cheeks. Hiccup reached out, grabbing her rear and causing her to wince. Elsa watched as he squeezed and rubbed his hand across her backside. "Yep, I think these will weal up nicely," he said before giving her a pat. "Up."

Heather groaned before pushing herself up to her feet. She stood straight, keeping her hands at her side. Elsa knew she must have wanted desperately to rub, but she didn't dare to do so without being given permission first.

Hiccup stepped forward, placing his hands on her waist and then leaning down to whisper something in her ear. Elsa couldn't make out what he was saying, but whatever it was seemed to be getting quite the reaction from Heather, as she squirmed nervously where she stood.

"Go on now."

Hiccup gave her a pat on the rear, and Heather began making her way off, not bothering to roll down her skirt or pull up her panties. Was she going to have to present herself to the rest of the office? Once she had left and closed the door behind her, Hiccup turned his attention to Elsa.

He smiled as he held the cane up in front of her. "What did you think of what you just saw Elsa?" he asked suddenly. "What do you think of this?"

Elsa looked down at the cane and then back up at him. What exactly was he asking her this for? Was this another trick? "I don't have an opinion on it one way or another, sir," she said, crossing her arms.

"Elsa, c'mon. Be honest. What did you think? Speak freely."

"With all due respect sir, if I spoke freely right now I'd likely get a much deeper impression of that cane than I would like," she said. She realized it was rather snarky of her, and that wasn't exactly the best route to go in this situation, but it had technically also answered his question.

He chuckled, looking amused. "Smart girl. But I would turn down the snark if I was you. It's going to land you in a lot of trouble," he said as he set the cane down on the desk. He walked over in front of her, and she stared back at him with a stern expression on her face. She knew he was plotting something right now, but she wasn't about to just timidly lower her head and back down in front of him. "Know why I called you here?"

Finally, it seemed like she was going to get some answers. "No sir…"

"Astrid likes you," Hiccup explained. Elsa looked confused. She supposed it was nice to know Astrid felt positively towards her. She had seemed a bit reluctant to even speak with her at first. But what exactly did that have to do with anything? "Apparently your reputation as the spoiled little boss's daughter was shattered when Flynn punished you."

Elsa hummed. "I suppose I should thank him then," she said, sarcasm very apparent.

Hiccup reached behind her and then suddenly gave her a sharp smack to the rear. She jumped, and then looked at him annoyed. "I like your wit, but you really do need to learn to keep it in check. I wasn't being coy when I said it would land you in trouble," he warned, sounding a bit more serious this time.

She looked down, a slight blush coming across her cheek. "Of course sir. I wasn't trying to be rude. I apologize." She couldn't let her annoyance at this whole situation make her slip up. She had to keep it together.

"Good girl. Now as for the reason I called you here, I wanted to offer you a deal that I think might make your stay here easier. Astrid would be disappointed if you ended up giving in too early, and I figured this could be a little gift to her."

Elsa raised an eyebrow. Why exactly would he have wanted to do something for Astrid? Were they… involved? Or was this just another sort of tric? Hiccup was far harder to read than Flynn or Hiro were. They were very forward in what they wanted and how they went about getting it. But Hiccup was obviously a bit more clever, and she found herself questioning every little thing he did.

Still, she didn't see how hearing him out could do her any harm. "May I ask what type of deal it is you're offering exactly?" she asked. She really hoped he wasn't so bold as to ask for some sort of sexual favor. Even for this place that was crossing a line.

"Jack is testing you right now. Leaving you to me, Flynn, and Hiro to break in. You're a very capable and organized worker. But you're going to slip up eventually. And when you do you better believe that every man in the office will jump on the chance to take a swing at you. And I'm certainly not going to pass up on any chances myself."

Elsa hummed, remembering what Gogo had told her before about what happened when her grace period ended. Having her workload increased and then having to run from office to office to get punished by all of them when she couldn't keep up. So far she hadn't tried anything like that with her, but the day was still young.

"So, my offer to you is that you request to become one of my personal secretaries. That way instead of having to scramble all about the office trying and failing not to step on the toes of every guy here, you'd just have to worry about answering to me. And Jack on occasion of course," he explained.

Elsa narrowed her eyes. "And you'd also have me pretty much all to yourself," she pointed out. The implication of what he was suggesting wasn't lost on her, even if he did try to make it sound more favorable to her than to him.

Hiccup chuckled. "Well of course. And I don't think I should have to tell you that I'm not going to make things easy for you. But it's still better than the alternative I think."

That was… debatable. She couldn't deny it might have some merit. With every man in the office pretty much watching, waiting, and plotting for her to screw up, she felt like she could never have a break. But if she was just under him, then it might take some of the pressure off. But she had absolutely no doubt that he could, and eventually would, execute some scheme to have her over his desk and bare bottoms of that cane.

Punishment was inevitable, she had accepted that on some level. But now she was in a situation where she could choose the lesser of two evils. She just wasn't sure which one that was. "May I have time to think about it sir?" she asked, doing her best not to sound as conflicted as she felt. If his plan was to make her overthink the position he was putting her in… it was unfortunately working.

"Of course," he said, nodding. "If you come to a decision, then let me know. We can talk to Jack about it. Now you're dismissed. I'm sure you have a lot of work to do. And remember to watch that wit."

He emphasized the point with another sharp slap to the rear. Elsa once again looked annoyed, but bit back another smart comment. "I'll keep that in mind sir. Thank you," she said before turning and walking out.

Hiccup watched as she left, feeling content in the little seeds he had planted. Whether he accepted his offer or not, things would work out for him either way. And it would effectively rattle Elsa too. If she did accept Flynn and Hiro might complain, but he doubted Jack would. Of the three of the Hiccup was the best suited for dealing with strong willed girls like Elsa.

Now, he had to call in a certain blonde to deal out some more strokes of the cane.

A/N: Little less spanking, and a little more setup! Anna is practically wrapped around Jack's thumb, and her big sister in one the wiser since she's got her own problems to deal with. And is Elsa going to take Hiccup up on his offer? Will her choice work out for better or worse? Either way the chances of her getting through it with her bottom unscathed are slim to none!