From Supervillain To Damsel

*This is a story I wrote a while back and posted on DeviantArt. Contains bondage, humiliation, and lots of half-remembered D&D stuff from my teenage nerd days. Reader discretion is advised.*

*

"She'll never fall for it," said the officer of the watch. "I guarantee it."

The officer, a tall brunette with rippling biceps and a two-handed sword, was as tall as most men, but she towered over Woody. This was because Woody was a halfling, barely three feet tall. He felt distinctly intimidated.

"I am a bard," he said, in a voice projecting considerably more confidence than he felt, "and you underestimate the persuasive powers of bards at your peril. This trick is going to work just fine. You park the prison wagon outside the castle at midnight. I'll supply the prisoner."

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The trick, as he called it, was more like a suicide mission. He was going to try to collect the bounty on the most dangerous warrior in the kingdom, and he was going to do it single-handed.

The name of his target was Irina the Invincible, and to call her a warrior was an understatement. She was a 20th-level fighter, but she was at least 10th level as a mage and had higher thief skills than most thieves Woody had met. There used to be two dragons in the realm, but she had killed both of them - which might make her sound like a good guy, but she had killed a bunch of good guys too. The king had placed a bounty of 50,000 gold crowns on her head, or 250,000 if she was taken alive. Nobody thought the second one was even remotely possible.

But Woody had other ideas. His plan was to visit Irina's castle in the guise of a beggar (this wasn't exactly a 'guise', he felt, since he had precisely zero gold crowns with which to buy his next meal) and trick her into giving herself up.

Yep, that was the plan.

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"I really think we should postpone until Mark and David can be here," said the DM.

"It's not my fault they cancelled," complained Woody.

(Yes, he was the kind of player who names their character after themselves.)

"Honestly, this is the worst plan I've ever heard," said the DM, whose name was Emily. "Irina is way out of your league even with a full party. Please can we do something else?"

Woody could think of a few something elses he'd like to do with Emily, who was looking startlingly pretty tonight; in a decision for which he was still thanking God, she had decided to run their group's D&D sessions in a sort of fantasy cosplay, which tonight meant a shiny, tight-fitting blue dress with a lace-up corset. But he was pretty sure she was still hung up on Mark.

"I still think Woody can pull this off," he insisted, not entirely displeased with Emily's smile when she heard the innuendo, "and I'd like to give it a go. Please?"

"Fine. But if I were you I'd start thinking about what character class you'll want to roll up after little Woody dies."

"That's easy. Halfling bard."

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The door creaked open, and a servant peered out and looked down ostentatiously, before asking Woody what he was about, and should he like to fucking well walk himself back to town while he still had feet to walk with? He spat on the ground while talking, and muttered several oaths under his breath about the trustworthiness of halflings.

"Ah, my good man! Your mistress asked to see me. She will be most displeased by the slightest delay. Lead on!"

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"You remember that you're appearing in the guise of a beggar?"

"Oh bloody hell. Dammit!"

"I'll apply a -5 penalty for the wrong costume, and a further -2 for the servant's INT bonus... Roll your Persuasion check, then."

Woody took out his lucky D20, and rolled.

Natural 20.

"Hooray!"

"Oh for goodness' sake. Fine."

========

The servant was not phased by the tiny stranger's peculiar garb; he presumed that wherever he came from, soiled rags were the costume of the nobility.

"Profuse apologies for my tardiness, noble sir," he said. "Do step this way with the utmost alacrity, and I shall supply a cup of wine presently. Should sir like to borrow a fresh tunic, the mistress being so particular in her sartorial tastes?"

"If you have the correct size, certainly."

Suitably attired - or more suitably, since the garments supplied were all either too large or designed for children - Woody was ushered into Irina's presence. She gave him a look of the most utter contempt.

"I shall have my servant horsewhipped," she said. "How anyone could imagine that you fall under the category of foreign nobility - let alone rush to furnish you with wine and borrowed clothes! You are a common halfling, here to steal the candlesticks! Do you dare deny it?"

Woody reflected that being accused of theft was actually shading things on the generous side. One of the advantages of insanely optimistic plans is that nobody ever guesses what you're up to. Steal the candlesticks? No - I'm here to steal you.

"My lady, apologies for the lateness of the call and the undoubted shabbiness of these poor humble clothes, which your ill-mannered servant was so stupid as to supply in exchange for my own items, which he ruined with spilled wine. He should certainly be horsewhipped, although may I say that being horsewhipped by you would be a privilege that any man would be fortunate to experience."

"It is a privilege you will enjoy very shortly, if you do not quickly explain yourself."

"I should envy the handle of the whip, to be caressed by those alabaster hands, just as I envy the material of your bodice, which is permitted in turn to caress those alabaster breasts. But I digress, madam, since I am here on a dual duty, the one sadly displacing the other on account of its very much greater urgency. I am here to sing your praises with my lute; and to warn you of impending danger."

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"You need to pass a Charm check just for her to hear you out, Woody. And you've provided no reason for her to trust you, other than some embarrassingly clumsy flattery. I'm setting a -8 penalty on this. Plus her INT bonus, which I won't disclose at this point."

"So you're saying there's a chance."

He rolled the lucky D20. Natural 20.

"Woody, you are one lucky son of a bitch."

========

Irina suddenly seemed to defrost. She seemed very self-conscious about Woody's flattery; he wondered if she had ever been complimented before.

This seemed unlikely. She was a goddess: almost six feet tall, with perfect skin and shimmering blonde hair. Woody knew she was amazingly strong, but she didn't look like a fighter: her build was slim and feminine. He had chosen her breasts for comment with good reason. They were stunning, and her garb - a shiny, tight-fitting blue dress with a lace-up corset - showed them off to great advantage.

"I should very much like to listen to your lute, sir, but beg you to waste no time in telling of the impending danger of which you speak."

"Trolls. There are trolls coming to the castle. We need to smuggle you out."

========

Emily rolled her eyes.

"That's all you can come up with?"

"Everybody hates trolls."

"Yes, but the best place to deal with a troll invasion is from inside a stout castle, surrounded by trusted servants and mercenaries. Aside from the fact that Irina kills the things that kill trolls for fun, for fun."

"So you're saying there's a chance?"

"There's always a chance. But I'm not even going to tell you what penalty I'm applying."

He rolled the lucky D20. Natural 20.

"Woody, is there something you're not telling me? Did you sell your soul to the Devil?"

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"Trolls, sir? I am most exceeding affrighted of trolls. Can you assist me in eluding these dread creatures of the night?"

Irina was behaving very eccentrically tonight. It was as if her character kept changing.

"Sweet lady, mayhap I can. By kindly fortune, I happen to have conceived a ploy. A trick that should confound and confuse the trolls, and allow you to leave the castle in safety."

"And what is the nature of the ploy, pray tell?"

"You shall pretend to be my prisoner."

========

"Your prisoner? This is the plan you've been leading up to?"

"Yes! I still have the Cords of Binding that I got from the first quest you sent us on-"

Emily looked extremely shifty at the mention of this item.

"-and I simply have to persuade Irina to let me tie her up with them."

"Woody, I will say only this. You need a natural 20."

He rolled the dice...

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"Blessed sir, I am grateful for your offer of assistance, but must beg leave to enquire as to why this stratagem should be necessary?"

"The trolls wish to capture you and take you back to their lair. I will do my best to spirit you past the trolls, but if any see us it is vital that we are able to claim that you are already a helpless prisoner, bound and gagged and being transported to a life of bondage. I will tell them that I am a humble mercenary, paid by other trolls to assist in the capture of their enemy. They will allow us to pass unmolested, and very likely wish us - or rather me - good cheer."

"You say I must be bound and gagged? If you deem this necessary I shall of course submit, but must observe that I am possessed of very great strength and feel sure that no ordinary rope can hold me. Shall this cause difficulties?"

"It shall not. I am come equipped with especially stout rope that will do admirably. Now please cross your wrists behind your back, and I shall bind them tightly. It must be extremely, painfully tight, for trolls are perceptive creatures and we must ensure that you are truly and utterly helpless and entirely unable to escape, lest the deception be spotted."

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"Trolls are not perceptive creatures, Woody."

"Another Persuasion check?"

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"Oh I am persuaded that you are entirely right, my dear sir! I truly believe that I should trust implicitly anything you should tell me, no matter how unlikely! Shall I take off my dress before I am bound?"

"I think that would be wise. We must think, how and in what manner would a troll bind you? And the answer is, in your underwear. And with an almost implausible quantity of rope."

Irina stepped out of her dress, exposing lacy undergarments that offered little protection from the elements or Woody's eager gaze. She was astoundingly beautiful. Goosebumps already showing on her pale, flawless skin, she crossed her wrists behind her back, and stood obediently to be bound.

But there was a problem: Irina was twice Woody's height, and he didn't think he could reach.

"Hold still for a moment," he said, then went and fetched a chair that he could stand on. Once he was up at her level he looped the magic cord tightly about her wrists, and tied it off, using his entire body weight to cinch the cord. It was obviously uncomfortable: her back was arched and her breasts thrust forward. But she remained meekly in position, waiting for the next instructions.

"Please could you help me get your elbows together?" he said. "I find I do not quite have the strength."

He wondered if he was the first kidnapper in history to be so much weaker than his prisoner that he had to ask for assistance in applying the ropes.

Between the two of them, they got Irina's elbows touching, and Woody bound them tightly in place. Sweat was running down her face now, but she had clearly resolved not to speak unless spoken to.

Woody moved on to Irina's powerful and well upholstered chest, wrapping it with loop after loop of tight cord, before jumping down from the chair and binding her legs together, at ankle, knee and thigh.

"If I may be so bold as to speak up," she whispered, "how shall I walk with you to safety, with my legs so comprehensively bound?"

"You will hop with your feet together. It will be extremely humiliating for you, and that is good, because the trolls would never suspect that a proud warrior would put herself through such a humbling ordeal."

She nodded, sagely.

"We are almost done. I believe you are helpless, but would you please struggle as much as you possibly can, so I can see if any loose cords remain?"

She writhed and strained her utmost, her powerful muscles showing beneath the bonds, but the knots - and the cords themselves - held. She was caught. She was helpless.

"Very good, although I believe I detected a trifle of slack here, here and here."

He adjusted and tied off a few of the cords, making them - if such a thing were possible - even tighter and more secure than before.

"Which just leaves the gag."

"The gag, sir. Of course. Although, could you remind me why it is necessary that I be silenced as well as physically helpless? Seeing as how the trolls have me in their power and there be no living thing with the power to rescue me from them?"

"Think of it as a favour to me. It's funny and pleasing for me to look at you with a nice tight gag in your mouth, shutting you up completely. It is vital that you not be able to say anything at any time, unless I allow it, which I shall not. Is that quite understood? Now open wide, please."

"I am not sure I quite-"

========

"You passed your Rope Use and Strength checks with a pair of natural 20s, so she really is helpless, Woody. At this point you can just shove the gag in her mouth whenever you find it convenient."

"I'd really like it if she submitted, even now."

"Well, then you'd better take one more Persuasion check, and let me tell you your explanation was rather lacking..."

========

"Of course I understand, it is clear now. Gag me as tight as ever you can!"

She opened her mouth. Woody jumped back up on the chair, but it was not enough.

"You had better kneel," he said. She dropped to her knees; no easy matter with her body so strictly constrained.

The most powerful warrior in the realm was kneeling before him in her underwear, tightly bound and allowing him to apply a gag; it was surreal. He knotted a length of fabric that he had torn off her dress, put the knot in her mouth and yanked back on the ends, tying it off tightly at the nape of her neck.

"There we are. What a sight you are. What a prize!"

"Mmmmphhh?"

He helped her back up on to her feet. Irina stood before him, struggling and straining to keep her balance, with every limb, every fibre of her being held immovably precisely where Woody wanted it. She couldn't move a muscle. She could barely make a sound.

Her wrists were bound tightly behind her back, and her elbows were tied together with knots far out of her reach. He had looped cord around her neck, shoulders and stomach, and above and below her breasts: her upper body was entirely framed in rope, like a painted masterpiece. Her legs were bound, a single useless limb. Her lips were trembling around the stout gag, which silenced her so effectively. The powerful warrior and mage of half an hour since had been transformed into a helpless damsel in distress. Yet even now she was looking at him with total trust, as if he was working for her benefit.

"We are ready to depart. I do not think it necessary to hide you with a cloak as we discussed before because... ah, because I want people to see you so debased, so humiliated. I want to show you off as my humbled prisoner."

She nodded. That seemed reasonable.

"We don't want the trolls to get their hands on your treasure now do we? You had better tell me where it is hidden."

"Mmmphh mmph mmmmmph." She did her best to signal with her head, although the cruel cords around her throat made this difficult.

"Behind the tapestry? Excellent. Would there be any magical traps, by any chance?"

She mewled eagerly, then hopped on the spot until her bound hands were facing him. She had worked a large sapphire ring off her finger and was holding it out.

"This will protect me? How fortunate."

Woody put on the ring, and disappeared behind the tapestry. Half an hour later he reappeared clutching a bulging sack, from which the jewelled hilts of several magical swords poked. Irina was exactly where he had left her, exhausted, tottering on her high heels and covered with sweat.

"I've got the weapons, the armour, the jewels and gold coin, plus this handy Bag of Holding to carry it all," he said cheerfully. "And I'll hold on to your ring, too."

She nodded, as best she could. Of course. That all made sense! How lucky he was here to save her from being robbed and kidnapped.

"Now hop that way, prisoner." He opened the door and pointed outside.

Hop, hop, hop, down the corridor, hop, hop, hop, her breasts bouncing up and down, hop, hop, hop, sweat covering her face and chest, hop, hop, hop, finally to the main door of the castle.

The servant was staring, open-mouthed, at his haughty, all-powerful mistress, standing before him half-naked and utterly helpless.

"Mistress? What happened?"

"Don't worry, my good man, this is merely a jolly jape to amuse the locals. Isn't that right, prisoner?"

Irina nodded, gave a soft mmphhh and drooled on her chest.

"Well, I'll be... I take my hat off to you sir, I really do. The mistress tamed at last, and by a halfling of all things! I never thought I'd see the day."

"Thank you. Now open the gate, would you? We have guests to entertain."

The gate creaked and clattered down. Woody peered out, then turned back and beckoned to Irina.

"They're all here. Come on."

She looked confused for a moment, but then relaxed - as far as her bonds allowed. The trolls. The trolls were here. What a good thing this clever man came along just in time to save her!

She gathered her strength and started to hop, focusing on her bound feet and doing her best not to fall over. Wouldn't that be humiliating, she thought!

It was only when she was almost across the bridge that she looked up and realised that Woody hadn't followed, and was still on the inside of the castle. And there was a huge crowd outside. The watch were there, with their prison wagon. And it looked like most of the town had turned out too. They were all staring at her, many open-mouthed, some starting to laugh... and then it spread. They were all laughing. They were laughing at her! What had happened?

The officer of the watch stepped forward and took hold of her arm.

"You just come with me, ma'am. We'll find you a nice bed for the night. And Woody, my goodness. I didn't think you had it in you."

It was at this exact moment that Irina understood. How she had been tricked: how she had fallen for the weakest story imaginable. How she had willingly stripped, and allowed herself to be bound and gagged, rendered helpless by a creature half her size and a hundredth of her power. And how - Woody was waving the sack at her - she had even helped him to steal her priceless possessions.

*Now* she fought back. *Now* she struggled. *Now* she called out to her mercenaries to rescue her. But it was too late, far too late. The ropes were too tight, and too strong, and too well tied. The gag was too secure: nobody could tell what she was trying to say. She was a helpless captive, and her obvious fury and humiliation only made the crowd happier than ever. They had all lived in fear of the mistress of this forbidding castle, and seeing her dragged from it a defeated and humbled captive, wrapped in ropes, stripped to her underwear and gagged - that was the best part, the gratuitous humiliation of the gag - was more than they could wish for.

All of a sudden the struggle stopped, and she began to cry softly. The officer of the watch lifted her into the wagon and bound her into a strict hogtie. The crowd cheered as the wagon moved off, before heading en masse into the castle to see what they could grab.

========

Emily was sitting quietly, looking at Woody - the real-life Woody - with an expression that mixed amazement and newfound respect. And perhaps a frisson of excitement.

"I can't believe you did that. Irina was far too powerful for you, far too smart and capable, and yet somehow you tricked her, bound her, gagged her, and walked her out of her own castle as your helpless prisoner. You're some kind of genius, I think."