Hero Undercover: 25 Breathtaking Bad Boys

by Annabel Joseph

  But if he knew Nanny Tillie, this had been done purposefully, keeping Miss Henrietta uncomfortable, forcing a modicum of humiliation, aiding in her submission.

  "Come, Henrietta, stand before me." He unfolded his legs, spreading them wide and setting his drink down on the nearby table.

  Miss Henrietta shuffled slowly toward him, wringing her hands in the crisp white flannel gown, her peach areola and nipples faintly visible.

  His cock stirred behind his pants; he cleared his throat, doing his best to dispel his sexual fantasies, focusing on the exquisite woman standing before him. Lightly grasping her hand, he gently tucked her between his knees, not letting go of her. He stared up, her azure eyes sparkling in deep contrast to the bright white of her nightie.

  Who would have guessed a bath could transform the little urchin he'd spanked today into this magnificent woman? It made him wonder exactly how long it had been since she'd dipped into some water.

  "Was she a good girl, Miss Matilda?" He tore his attention away from Ettie, fixing his eyes upon the stern nanny he grew up with.

  "Well, she had a moment of sassiness, sir, but it was nothing for you to worry about or I would've called you to handle it. I put a bit of suds on her tongue and spanked her wee wet backside, and she's been without incident since. She's a good girl, Master William." Tillie winked at him, obviously enjoying the alias and deception more than he could have thought.

  Charles narrowed his gaze at Ettie; her breathing shallow and fast.

  Fear.

  He'd keep her on edge, wary and concerned, with more than a little trepidation. "The spanking in the jail wasn't enough to curb your brazen tongue, girl?"

  "I-I guess n-not, Sir." She averted her eyes from his, staring at her feet.

  Tilting her chin up, he stared at her intently. "Is your throat and tongue still burning with your punishment?"

  "Yes, Sir."

  He nodded slowly at her. "It must be so because you haven't called me Sir twice in a row since I've met you. Good." He reached around, running his hand over her bottom through the soft flannel and then asked Matilda, "Is she wearing no drawers or pantaloons, Nanny?"

  Ettie's cheeks turned pink with her blush.

  "No, she isn't, sir. I thought she'd mind better without them, and it will make the process of spanking her easier for you, if you don't have to fiddle with all that frippery."

  "Indeed. I think I shall keep Miss Henrietta in this attire until her initial training has been completed. Nighties and a bare bottom it shall be until you receive further direction, Matilda."

  "As you wish, sir." Matilda nodded her head toward him.

  "B-but, it isn't proper, Master William. I mean. If you're intent on training me to be a lady of society, how do you propose that will happen, wearing nothing but my nightclothes?" Her chin tilted up, the corner of her mouth quirking up with a smidgen of smugness.

  She thinks she has me bested.

  "Ah, my naughty moppet. You see, that's where you're wrong. Dead wrong." To add insult to injury, he patted her bottom with a familiarity he had no doubt rankled her. "My goal, first and foremost, for your training is total and complete obedience and submission. And what better way to do this than to keep your ass and quim bare and available for punishment…or other delectable things, as I deem necessary." He leaned back, his elbow resting on the chair, cupping the side of his face with his thumb and forefinger, returning the smug smirk.

  "But can't that happen with my pantaloons on?"

  "It could. But I don't wish it." Resting his hand on her hip again, his finger pressing into the tender, plump buttocks, he grinned fiendishly. "And you'll find, my dear, what I wish is all that matters at Carlton Towers. And obviously, Nanny thinks you'll behave better with less attire, also. So, the matter is solved. It is a bare bottom and nighties until I direct otherwise. No more discussion."

  She pulled her lip between her teeth, biting it nervously.

  Charles leaned forward, and the little thing jumped back. "Oh, Ettie. There's no need to worry. If you're a good girl, we'll get along fabulously. Is it hard for you to imagine being well behaved?"

  "I-I didn't say that, S-Sir. I'm just…unsure."

  "I think it's time to get this whipping ordered by the magistrate over with so you may settle here and eat your dinner."

  "May I eat first and then have my whipping, Sir?"

  He hedged only for a moment, wanting to give her a bit of hope—and wishing he could forgive the thrashing. If only. But she wouldn't eat well with a punishment hanging over her head.

  "No, it's best to get it out of the way." He abruptly stood, seizing the wide strap from the table, and he pointed it toward the far side of the room. "We'll commence with you over my desk."

  Her hands tightly clasped in front of her, she shook her head vigorously.

  "That's not the response, girl. Is it that you need some incentive, thus making your batty fang much worse?" Charles couldn't believe she had the pluck to refuse but was impressed she courageously stood up for herself.

  Walking slowly up to her, as one would a fractious animal, he tucked a lengthy curl behind her ear. "Tell me, sweetling, when was the last time you were spanked? Has it been so long, you've forgotten it's only a few minutes of pain and then it's all over?"

  Ettie's eyes welled and blinked quickly; the tears slowly tracked down her cheeks. "It's been since I was sixteen, Sir. My father spanked me for my sassiness and I've never been spanked with something…like that." Her eyes focused intently on the evil strip of leather in his hand.

  Charles knew the feeling. Nothing seemed more dreaded than a belt when faced with correction, but the suppleness was more forgiving than wood, in his mind. But he knew he'd also stood on trembling knees many times, just as Ettie stood now, frightened by the same implement.

  "I'm not an easy headmaster, Ettie, and you'll find obedience to be in your best interest, but there is one thing you'll never have to fear, my dear. I'll never harm you. Will I cause you discomfort and tears? Yes. But to truly injure you or cause detriment? No. It's best to comply with my demands, take your punishment, and find comfort in my arms, once your atonement has come to completion. And Matilda is here to observe, and I assure you, she'd never let me go too far."

  "Aye, you can count on it, Miss Henrietta. You'll be safe with Master William; he's a good man." His nanny beamed toward the little thief, and once again, Charles wondered how different his life would have been if it hadn't been for the faithfulness of Randall and Matilda.

  Charles watched the emotions clearly displayed on Ettie's face. Her eyebrows furrowed, staring at the belt, her hands wringing with anxiety. With probably more than a bit of trepidation, she looked over at the desk, blinking quietly. How he wished he could be in her head, to hear the thoughts running madly through her mind. Her gaze returned to him, searching his eyes, her eyelids fluttering before returning her focus to the desk again.

  Then with a small nod, she looked up at him, and with a tilt of her chin, which he'd grown to admire in this short time with her, she quietly said, "Sir, I'm ready for my…spanking."

  "That's a good girl." With a hand on the small of her back, he walked her to the desk, gently pushing her over the edge until her upper body lay flat, resting her face against the hard surface. "Keep your hands gripping the edge. You're not to bring your hands back, understand?"

  "Yes, Sir."

  He swore his hands trembled when they took hold of the hem of her nightgown, her lush thighs coming into view.

  Ettie pushed herself up. "Oh no! You're not baring me, are you?"

  "Down!" He waited for her to rest her face against the desk again before continuing. "You were informed more than once, my dear, I will only spank you on the bare. It is senseless and, well…unsafe, in my estimation. First, there is no need to expend the energy required to discipline, only to have your clothes take the brunt of what is meant to correct a naughty girl and her backside. Second, it is imperative the disciplinarian see where every
mark is placed and watch for any signs of bruising or damage. If the offending area is covered, it is possible to strike in the same spot too often, thus causing injury. I refuse to take such a chance. Therefore, a bare bottom is how all spankings will be dealt with in this school. Period. The discussion is over."

  A choked sob was her answer, and he continued by grasping the hem of her gown, once again. This little slip of a woman wouldn't dictate how a correction would be meted, that was his job and one he aimed to do thoroughly.

  Dragging the flannel up her legs, he continued its upward march, her quim peeping from between her thighs. Her pert, round buttocks had his heart hammering in his chest and his cock pulsing behind his pants. He bunched the material onto her back.

  "In the future, you'll be required to pull your gown up before taking position, exposing the lower half of your body for my view while you recite your sins. Then, your hands will firmly grip the hem of your gown for the duration of your thrashing, keeping them occupied and out of the way. Today, I extended a bit of grace to you. You've had a lot to take in, and I'll do my best to help you along, when necessary. You may thank me, girl."

  "Th-thank you, Sir."

  "Hold onto the furthest edge of the desk."

  He waited for her trembling hands to grip the hard wood, her knuckles white. "What is this slating for, Henrietta?"

  "F-for stealing an apple, Sir."

  "Indeed. And the magistrate was kind in giving you a reprieve, and I won't betray him by going easy on you. Stealing is grave, requiring a harsh correction." Taking a deep breath, he steeled himself for the task ahead, centering his attention on what was required, doing his best to avoid caving into any sympathies toward her.

  Swinging his arm wide, he laid a wide pink stripe on her backside—hitting harsher with the first smack, wanting to gauge her limits by the cry that followed.

  She stiffened, shouting loudly. "Ow! Oh, God!" Her fingers milked the edge of the desk.

  "Stealing is wrong and a sin!" He lashed the strip of leather along the crest of her ass, the flesh wobbling with each swipe.

  Charles' cock swelled, throbbing with his arousal. He'd always imagined whipping a naughty bottom, but in his wildest fantasies, it had never been as erotic as this. And although he felt guilty for it, he loved her cries and tears, the power…control…dominance. His heart ached at the misery lacing her pleas for mercy, the choked, indecipherable words spilling forth as a result of her pain. The suffering incurred by his hand and this strap.

  Charles wasn't sure he could imagine anything more intense or glorious as this experience, but he sure as hell hoped he could surpass it within the next few weeks.

  His arm had been rhythmically slapping her rump with the belt, her skin now welted with spider veins appearing. Stopping, he ran his hand over her hot, inflamed flesh, the skin quivering.

  Henrietta waggled her bottom, struggling to avoid his touch, but he wouldn't let her movements deter him. His fingers brushed against her sex, her labia moist with her juices.

  Is she aroused by this? Are we both feeling the excitement?

  Cupping the plump pouch of her sex, he eased his middle finger between her lips, the tip of his finger easily finding her clit and lightly brushing around the hard nub.

  "It appears you're enjoying this, even though the rest of you is in distress. Your hot cunt is dripping, my dear. I'm going to slip my finger into your crinkum-crankum, giving you a bit of relief before we continue."

  "Oh…M-Master William…I…should we—"

  "I'm stroking your quim, girl, not taking your innocence. Relax." Dipping into her channel, he brushed along the slick tissue, pressing against her secret spot, persistently rubbing the spongy surface.

  He wondered if he'd survive bringing her to completion without spilling his seed, making a mess of himself in the process, but currently, it seemed the least of his concerns.

  "Oh! Master…Oh…I'm—"

  "That's it, moppet. Let it go; you'll feel so much better." He poked his pinkie into her bottomhole simultaneously brushing her clit and her body immediately stiffened with her low growl, her sex clenching and milking his fingers, her hips bucking and pounding the hardwood.

  "That's a good girl, Ettie." Charles continued to prod his fingers into her depth, extracting every last spasm from her dripping cunt. Removing his fingers, he wiped the excess fluid on her hips before pulled her to stand before him, letting her gown drape over her body again. Tucking her to his chest, he turned, addressing Matilda, "Nanny, we'll be fine now. Can you tell Cook we'll be ready for dinner in a half hour's time?"

  "Of course, Master Ch—William." Her hand covered her mouth, shocked she almost gave his name away.

  "Thank you, as always, Tillie."

  Ettie hiccupped the remnants of her sobbing and chastisement. Charles walked with her to the settee, curling her onto his lap and resting her head under his chin. She fit easily and securely in his arms, her petite stature an added benefit to both of them. He tilted her so the brunt of her weight rested on her left hip, avoiding her no doubt very sore hind end. His cock pressed into her thigh, but there wasn't much he could do about that—not yet, at least. He just hoped it wouldn't frighten her. There'd be time enough…very soon he hoped…for her to relieve his erection, giving him release as well.

  Turning his attention back to her, he crooned, "All is forgiven, Ettie. We'll start our day fresh and new. It's been an adventure, has it not?"

  "Yes, Sir." She mumbled into his chest, her fingers playing with the buttons on his shirt, the rhythmic hitching of her chest tearing his heart apart with guilt.

  He shifted in the chair, doing his best to keep her warm, decadent body from resting on his throbbing member, resembling a steel rod at this point. His tallywags were no doubt blue, the ache overpowering.

  It was daunting to know someone's sorrow was directly tied to a whipping carried out by your hand. The feeling was foreign to Charles, and yet one that he hoped would occur again because the thrill that ran through him was unlike anything he'd ever done before, including hunting.

  The power of dominating someone with your authority was not foreign to him as a duke, but wielding an implement, making one atone for their sins and beg for mercy was unfamiliar territory, but one he wished to make commonplace in his life.

  "Don't tell Cook or Nanny I'm doing this." He fished into his pocket, pulling out a hard cinnamon candy. "Would my good girl like a treat before dinner?"

  "Oh…yes, Sir." Her big blue eyes widened, a smile spreading across her face, and he swore he'd never seen anything more wondrous, and he vowed, right then and there, he'd find ways to make her do that at least once daily. She tentatively reached out, attempting to take the candy from his hand.

  Quickly closing his hand before she could snatch it, he looked at her solemnly. "I mean what I say. When you're a good girl, you'll be rewarded, Ettie. But, for today, you must promise not to tell Cook I did this, or she'll tan my hide or, even worse, don't tell Nanny." He shivered dramatically, opening his hand, offering to her.

  Ettie popped the little red candy into her mouth, giggling delightfully. "I promise, Sir."

  Enveloping her in his arms, he rubbed her bottom through the flannel, the heat so substantial it was easily felt through the material.

  I could grow used to this.

  Chapter 7

  Charles' shoes were wet with dew from his gardens. He loved nothing more than strolling among the flowers and roses early in the morning, just after the sun had risen. The quiet, only broken by the singing of the birds, helped him plan, organizing his thoughts and agenda for the day. Extracting his pocket watch, he checked the time and decided to head on back to the house before his cook, Agnes, had his neck.

  The smell of bacon and syrup wafted on the air as he climbed the stairs up to the house. Inhaling deeply, his stomach growled with hunger. Time for breakfast and to see what his naughty moppet was up to, this fine day. It had taken her a week to settle in, adjusting to their
schedule and catching up on her sleep. Today would be their first day of school.

  Charles swung the screen door open, stopping dead in his tracks at the sight before him. He blinked several times, making eye contact with his cook and nanny. He had no doubt they saw the question on his face, negating the need for him to voice it out loud.

  The cook, Agnes, glared at the girl, returning her gaze to Charles. "She decided to throw her oatmeal across the room—bowl and all. This is her punishment, Master William." Pulling a large wooden spoon out of a large pot on the stove, she waved it in the direction of his girl's bare, freshly spanked ass.

  "This position is…ingenious. I admire your handiwork, Agnes. It'll be a position I may replicate in my classroom. It is quite diabolical." With his arms crossed on his chest, he braced his face with his hand, studying every aspect. Every sadistic detail.

  Ettie was jackknifed, folded in half with her ass spread taut, yawning wide open and her anus peeping from between her cheeks. She braced herself with her hands on the floor, but what made this particular position fiendish was that she'd been forced to spread her legs wide, with a switch placed between her feet. And by the looks of her backside, she'd been switched several times by the branch before Agnes placed it with the ends poking into each arch of her foot.

  Ettie's lush breasts dangled pleasingly in front of her, the pebbled areola and steel tipped nipples begging to be cupped and plucked. Her broad hips, definitely needing more weight to bring them to the plump state he'd enjoy best but, still, the view enticing enough to make his cock twitch, wanting nothing more than to rut within her, sliding his member along the seam of her buttocks.