BAD GIRL ON THE HUDSON
“Do you know why you’re here, Miss Wells?”
The girl in front of me sneers and crosses her arms over her chest. I linger appreciatively on the too-tight stretchy tee she must've purchased specially for this scene when I warned her to prepare herself last weekend. This time, I didn't offer her a choice of roles; it's high time for Wendy "Wildcat" Wells to receive her discipline, and I know just the right headmaster for the job.
“My parents made me an offer I couldn't refuse.”
“And what was that?" I ask, baiting her for more.
"Lotus or the Psych Ward."
"I see," I answer, leaning back in my chair. "What made you decide on Lotus?"
"Pfft," she practically spits, "this place has way better food."
I have to bite the inside of my cheek to keep from smiling. "My reputation precedes me, I see."
She looks brazenly into my eyes and smirks. "Something like that."
Fuck, yes, Isabella. Bring on the feisty. Slip into the role and be bad for once...and bring on the consequences.
"What do you think your parents hoped to achieve in sending you here?"
She rolls her eyes like any bratty teenager. "They're trying to cure me."
"Cure you...of what?"
She unfolds her arms to place a pair of dramatic air quotes around her words. "Oversexualized behavior."
"You don't think you're oversexualized?"
"I know I am," she answers easily. "I just don't think it's a problem. I like cock. A lot. What's the big deal?"
My own cock responds immediately, but I answer her dispassionately, "You've just earned yourself a stroke of my paddle. You've read the disciplinary manual, I hope?"
"Yeah. I read it," she answers, trying for boredom but betrayed by the glassy look in her eyes.
"Good, because you're responsible for upholding the rules, and when you fail to do so, you will be punished. Swiftly and decisively."
She looks at me for several seconds, pondering getting herself into further trouble, I think, but eventually deciding against it—for the moment at least.
"So you don't think it's a problem to have indiscriminate sex with multiple partners?"
She shrugs petulantly.
"Do you feel it detracts from your studies?"
"Pfft, probably, but I can guaran-dam-tee you I'm learning twice as much as any other girl in Honors English!"
"For what? That's bullshit!"
"Three." I smile and fold my hands on the desk between us. "Keep it up, Miss Wells. My arm doesn't begin to tire until twenty-five; after that, I'll just gag you and lock you in the stockade."
"You have a stockade?" she asks, her voice husky and rough.
"We have some very generous benefactors here, and we take our mission quite seriously, as you'll come to learn."
Isabella’s tongue swipes across her lower lip, and I lift my eyebrows in challenge.
“That mission, as you’ll come to appreciate, Miss Wells, is healing girls like you so that you might curb—or better yet, redirect—your lust so that you may go on to live a productive life.”
Isabella guffaws, then quickly covers her mouth with her hand. “How are you going to do that?” she dares. It’s borderline defiant, but I let it go this time.
“You are going to learn to sublimate your urges to me.” I can’t deny the tickle of glee in my gut as I make the pronouncement, and I can’t resist taking it one step further. “In other words, your ass is mine, Wendy Wells.”
My ass, my tits, my pussy...and not insignificantly, my heart. “Oh yes, I read about that. You’re my Higher Power, or some such sh—stuff.”
He laughs. “Good catch there, Miss Wells. I see you’re already improving. That didn’t take very long.”
“No, Mr. ...er...?”
“Headmaster. You may call me ‘headmaster.’”
GAWD. I’m sitting here in a puddle, anticipating that paddling and so many more punishments I’m eager to earn myself. I’m not sure how long I can sit here squirming, and I’m pretty sure Headmaster knows the state I’m in. He’s fucking torturing me with this interview.
I toss out a Hail Mary in an attempt to move us along. “So how long do I have to stay in this godforsaken hell hole?”
“Four, and as long as I say. Your parents have signed an open-ended contract with me, stating that our ‘relationship’ ends when you’re properly cured of your urges. So...” he claps his hands together, “I guess you better get ready to follow my rules. Speaking of which, let’s review the most important before you go and change into your uniform.”
The uniform. The slutty schoolgirl kilt and red patent leather Mary Jane platforms, the knee-high socks—
My folded hands drop into my lap.
“...you understand that if you touch your genitals, with any part of your body or foreign object, you will receive a spanking.”
Bad, bad Wendy Wells. You should not be thinking about touching yourself.
“Yes, Headmaster,” I answer obediently, while silently pressing my knuckles into the denim, so as not to arouse his attention.
“And you are aware,” he continues, seemingly oblivious to my mischief, “that if, by this manipulation...”
Ahhh, fuck!...my hips squirm...the pressure feels so divine...
“...should you experience a sexual climax, you will receive a …harsh …paddling?”
Wet. Slippery. Need. Harder. Furiously, I scrub over the heavy layers of clothing.
“MISS WELLS!” Headmaster jumps out of his seat and towers over me. I am in trouble—clearly—but I can’t stop now. My heart rate spikes as I defy him, my need intensifying as I taste the stolen, forbidden fruit.
“STAND!” he bellows with great authority, his eyes blazing into my lap with great disdain.
A terrified shudder pulls me to my feet before the idea of defying him further can become an option.
“Remove. Your. Clothing.” His voice is calm; he seems to have regained control. I’m not sure, but I think cool, composed Headmaster is even more chilling than the slightly off-balance version I met seconds earlier.
“Here?” The makeshift intake area feels entirely too public for this dressing down, and despite all the depravity that has previously occurred in this space, I’m feeling quite effectively exposed, which of course, is exactly his goal.
“Five,” he enunciates clearly, crossing his arms. “Care to try for six and having me cut your clothing off with a pair of sharp scissors?”
“No, Sir,” I answer, quickly correcting myself. “No, Headmaster.”
“I will let that one slide if your clothing is off in five seconds...four...”
I practically tear the tee-shirt off, and luckily, I’m not wearing a bra. Headmaster’s eyes pop for a second when he sees that, and his grin doesn’t go unnoticed.
My jeans are already unbuttoned, so I yank down the zipper and peel off my thong along with my pants. In one desperate motion, I shuck off my high platforms as I kick the bottoms across the room.
“Very good, Miss Wells,” he says, smiling lasciviously while glaring at my naked body. “I should’ve known you’d be quick to disrobe for me.” My nipples are practically throwing themselves in his face, while my pussy is weeping with need.
“Spread your feet apart—open those naughty thighs. And cross your wrists behind your back.”
I know this position well, and Headmaster knows it will not fail to add to my arousal. My near miss with my clit has left me wet and wanting. Somehow I feel he has me right where he wants me.
My character is starting to pulsate through me, the rich cloak of authority settling about my shoulders like a thick royal cape.
“Oh, Miss Wells,” I cluck disapprovingly, “that body of yours has gotten you into a world of trouble."
I step closer, leaving only a breath between her heaving chest and my own. I clasp my hands behind my back and hold on tight; my need will wait while I effectively whip her into a frenzy. And then, well...I close my eyes against the tidal wave of lust that drowns me as Miss Wells’ punishments play out before my kinky eyes.
“Tsk, tsk. You have been a very bad girl, and you’ve only just arrived,” I say, shaking my head at the unfortunate pronouncement. “You’re not fit to wear the Lotus uniform. Ask for your punishment.”
“Headmaster,” she starts, “may I please have my punishment?”
“Nice try, but let’s see if you can do better, hmm? Your request should encompass the exact punishment and the reason for it. Try again, Miss Wells.”
She takes a deep breath and tries again. “Please, Headmaster, may I have my f-five strokes of your paddle for using cheeky language and trying to touch my genitals?” She blushes a gorgeous shade of pink, and her nipples pucker, causing a further tightening of my cock.
“You may.” I hear the gravelly rasp of my voice when I answer. “Luckily, you didn’t actually touch your vaginal area, or you would also be receiving a spanking by my own hand.”
Lucky for both of us, because I’m not entirely sure I could administer said punishment without blowing my bundle inside my pants.
Since returning from St. Lucia, we’ve made some “home improvements,” including a series of hooks on the TV room wall to accommodate some of our most often-used play equipment. Except for the occasional visit from parents and friends, our wall is decorated by my ever-expanding collection of crops, paddles, and whips.
Contemporary American Kink—it works for us. What can I say?
I walk over to the wall and retrieve Isabella’s favorite of all of Master’s tools—my black leather paddle.
“Hands flat on the desk, ass in the air.”
She complies quickly, dropping her head into the space between the desk and her body. I run my hand gently down her back, a small reassurance in the midst of this role play that I’m here with her, and that she’s doing great. I won’t disrespect her by breaking out of character, but I know she understands my message when she sighs out a long, cleansing breath.
“Count and thank me.”
Centering the paddle on her left ass cheek, I pull back and land the first stroke with a loud thud.
“One. Thank you, Headmaster.”
I repeat the motion on the other side, paying close attention to the hitch in her breathing. “Two. Thank you, Headmaster.”
The third strike goes right in the middle, and she jumps forward before catching herself. Her skin is a lovely shade of pink, and I know it’s warm to the touch, but I won’t allow her that kind of contact right now. Blows four and five come quickly, one on either side, and she’s breathing heavily and bouncing on her toes by the time I finish. I drop the paddle on the desk and gruffly tell her, “At least you know how to take your punishments.”
“Yes, Headmaster. Thank you.”
“Your uniform is in the bathroom. Go change and meet me back here in ten minutes. Don’t be late. Tardiness will not be tolerated under any circumstances.”
What is this? This is not the uniform Miss Goody Two Shoes Mills was handed, nor is it the slutty Halloween version of a Catholic school girl gone awry. No; this is an actual conservative plaid skirt and an actual button-down shirt and a an actual men’s tie (pre-tied, thank the good headmaster).
I quickly pull on the white ruffle anklets, failing to hold in my chuckle—really, Master?—and the black and white saddle shoes with a creamy pink sole. Nothing kinky there.
Underneath it all, however...well, there’s nothing. No undergarments at all. And I have a funny feeling Miss Wells is going to catch a wee bit of hellfire for that.
He’s left me two pony tail holders, and I swiftly divide my hair into two pig tails and hope I wasn’t supposed to braid them. He could probably do it way faster, but there’s just no way I’m going to be late. My ass does not need another paddling right now, thank you. Disobedience is one thing, but this guy is not going to mess around in the discipline department.
I open the door, and Headmaster is right there, hands on his hips, a stern look in his eye. He glances at his watch and actually seems a bit disappointed that I made it within the allotted time.
“Your nipples are hard.”
I look down at the two sharp protrusions under my blouse. Yep, he’s right.
“What rule are you violating?”
Fuck...something about evidence of arousal...
“Go sit down,” he barks, pulling off his corduroy jacket and rolling up his sleeves to the elbow. The intake office has been converted to a plain old school desk, complete with paper and pen. “Write this down:
Evidence of physical arousal is distracting and detrimental to the therapeutic atmosphere and will be eliminated.”
I dutifully capture all his words on paper, though he rattles them off quicker than normal.
“Write that out ten times, and raise your hand when you’re finished.”
I have to forcefully restrain my jaw from dropping, and I know I am blushing a bright rosy pink to be chastised this way.
“Why is your pen not moving? That’s one,” he announces matter-of-factly, waiting for my hand to begin before he backs away into the kitchen.
I write, in a perfect cursive I haven’t had occasion to use more than a handful of times since graduating high school. I dot every “i” and cross every “t” and I pour my heart and soul into those words. When I’m done, I look up, and he’s standing there, waiting for me. I feel ridiculously eager to show him what I’ve done, which causes me to blush even harder. Unfortunately, I’m so off balance by this kinky version of playing school, I completely forget that I’m supposed to raise my hand.
Jesus. Even trying to be bad, I try to be good and end up being bad. I suck. Now I’m mad.
I fold my arms across my chest and stare him down—a dangerous move—but if I’m going to get myself in constant trouble, shouldn’t I at least be trying?
His eyes narrow. “Two and quickly approaching three.”
I stare some more.
“Three. Four. You’re on tenuous ground here, Miss Wells. I can promise you that,” he rumbles.
I’m a chicken shit at heart, and I flail my hand in the air.
“Sit up straight and show some respect. Five.”
Damn my idiotic posture. When will I learn? I shore up my back and raise my hand politely this time. A wide, toothy grin takes the place of his scowl. “Yes? Miss Wells?”
“I’m finished, Headmaster.”
“Turn your paper over and recite the rule.”
“Evidence of physical arousal is distracting and detrimental to the therapeutic atmosphere and will be eliminated.”
“Good girl; I knew you could do it. Now—before you so foolishly earned yourself five more strokes of my paddle, there was a violation to be addressed. Stand and step close to me.”
It’s then that I notice for the first time what he is holding in his hand, and a shiver ripples throughout my body.
I step in front of him, and he orders me closer and closer, until the rounded tips of my shoes are touching his loafers. It’s uncomfortable to be this close while he’s someone else; he’s just creepy enough to thrill me.
When he speaks, I can feel the warm flutter of air on my face. “Hands at your sides, Miss Wells.”
He sets down the glass of ice and spins my necktie around to my back. Painstakingly, he begins opening the buttons of my shirt one at a torturously slow time. His eyes never move from mine, even while his fingers slide each plastic disc through the corresponding hole. His fingertips work down my sternum, baring but not touching my skin. I know he sees the want in my eyes, the unbearable need burning inside me, but he doesn’t satisfy my itch.
He gasps almost comically when he reaches the third button, where my bra would’ve been, had he cared to provide me with said undergarment. “No wonder I’ve been accosted by those odious, puckered nubs,” he teases, using the exact language he knows I’ll recognize from my own writing. “You’re not wearing a bra! That’s fifteen demerits, Miss Wells. Your offenses are piling up, I’m afraid.” He tsk-tsks his way down to the next-to-last button, then surprises me by yanking the blouse down over my shoulders and leaving it to dangle from the waistband of my skirt.
“Hands on your head, elbows wide,” he orders suddenly, causing a fresh rush of fluid to pool under my skirt. When I pause to imagine the consequence for that—and for not wearing panties—everything just gets worse. I am so horny right now, he could get me off with a single touch, but as he retrieves two ice cubes, I realize that’s not at all what Headmaster has in mind.
Without warning, he presses the ice cubes to my nipples and holds them against me firmly, daring me to move with his eyes. I whimper and pinch my eyes closed tightly, but I don’t so much as rock or sway. Wendy Wells is one tough cookie.
“Arousal is bad, Wendy,” he says, leaning in and using the familiar name with a low, intimate voice. “We can’t allow it. Pointy nipples are distracting. Look at my pants, Wendy. Look what your nipples have done.”
My eyes drop to his zipper, and sure enough, I can see exactly what I’ve done to him. The knowledge gives me a warm rush of happiness and pride, not that bringing up Master’s erection is exactly challenging. Still...
“I’m going to remove the ice and still if your nipples are still hard.” He does as promised, and it surprises neither of us that my nipples are still rock hard and standing straight out.
“Oh, dear me; let’s give it another try.”
This time, I suck in a quick breath before he accosts me again with the freezing cold. It’s almost worse because of the momentary relief, and I groan out loud.
He moves the ice in small circles, and I feel a fresh flutter of need down below.
His lips move to my ear, his warm breath a sharp, soothing contrast to the cold indifference of the ice cubes. “Bad girl...bad, bad nipples.” His teeth nibble around my ears and my whole body shakes. I’m keening now, whining and ready to beg.
“You’re a slut, Wendy. You need to be stopped. Say it. Say it out loud.”
“Nnnh...I’m a s-s-slut,” I moan, numbness setting in. And yet, those lips, those teeth...on my ear, my neck, lower, lower, almost...”
He pulls away the ice cubes and blows on my breasts, creating a cool current that brings up goosebumps and ensures my nipples are as hard as ever.
“Oh, too bad, Miss Wells,” he says, shaking his head in apparent disdain. “Our aversion therapy hasn’t worked. I’m going to have to take drastic measures.”
If only he’d touch me, just one little brush of a finger...a finger tip...the heat under my skirt is getting to be too much, the moisture is sticky between my thighs. I’m mortified and anxious as hell for his reaction. I know he knows, and the fact that he’s saving it just makes me that much more apprehensive.
Poor Wendy. She is a hot and cold mess, and there’s no relief in sight. Not for her, anyway.
A product of her training, Isabella straightens her shoulders and blocks off her stance. She’s uncomfortable as hell, but she’s a gorgeous submissive, even if a bit subversive right now—delightfully so. I love that she’s flexing her naughty muscle tonight; after all, that was the whole reason for the role play.
It was actually Marcus who put the bug in my ear a few months after we got engaged. He reminded me to watch for a master who started overlooking “minor” infractions and inventing scenes where my submissive wasn’t being challenged to her full potential. As usual, his instincts were dead-on.
Soon after, I took Isabella out to a quiet dinner, and I shared my thoughts with her and listened to her concerns as well. We came to a very swift, very unanimous agreement that the Headmaster needed to make a reappearance, and this time, there was no hiding behind the familiar good girl. Hence, Wildcat Wells was summoned to Lotus on the Hudson.
I’ll have to send Marcus a bouquet of purple tulips after this weekend, I decide, reaching into the top drawer of my closet and retrieving a brand new set of nipple clamps I’d just bought. Their bark is worse than their bite, but I’m not about to tell Wendy that.
I hurry back to my wayward student, absently pinching and releasing the clamps between my fingertips as I stride.
Jesus Christ. How did I not notice how spectacular she looked when I left the room? My gorgeous submissive, innocently dressed from pigtails to saddle shoes, except, of course, for the bare top half and bright red nipples. She literally takes my breath away, and I accidentally clamp myself in the thigh before realizing I’ve slipped out of character. The unintentional pinch is a solid wake-up call, and I make sure I gather my wits before I reach her. She deserves that much and more.
Remembering not to treat her any less roughly than she needs, I tug at one of her nipples, gruffly explaining, “This is what we have to do when girls don’t respond to the standard treatment.” With that, I set the clamp around her nipple and watch the inevitable hiss cross Isabella’s lips. I swiftly clamp the opposite nipple, finding it difficult to resist leaning in to kiss her.
“You can drop your hands now. I believe there was some paddling in your future?”
Her eyes widen before she checks herself.
“Oh, Miss Wells, you did not think I’d forget your punishment, did you? What kind of Headmaster would I be if I didn’t paddle a girl when she earned it?”
She’s appropriately speechless, and I show her to the back side of the desk once more. I slide the paddle across the palm of my hand. “Five more strokes, Miss Wells. This poor bottom of yours is going to be a bit sore tomorrow.”
Gathering the hem of her skirt in my hand, I flip it up onto her back without touching her body. Her ass is a perfect shade of pink, and it kills me not to be able to touch the tender skin, not to work my fingers between her ...
“Oh, dear.” Headmaster is going to have his hands full with this one, I note, observing the coating of slick fluid covering her pussy. “I’m afraid you’ve violated the rules again, Miss Wells. Can you recite the rule governing production of vaginal fluids?”
A somewhat meek voice floats up from the opposite side of her back, where her head is dropped between her shoulders. “Evidence of physical arousal is distracting and detrimental to the therapeutic atmosphere and will be eliminated.”
“Well, you certainly learned that lesson well, Miss Wells. It’s a shame your genitalia isn’t as obedient as the rest of you.” I grab several ice cubes from the glass and hold them in my flattened palm. “Spread your legs, girl,” I demand, pressing my hand to her pussy and holding it there while I deliver the first blow.
Isabella squeaks and squirms and forgets completely to count and thank me.
“You’ve just added three more strokes to your troubles, dear girl. I suggest you concentrate.”
“Yes, Headmaster,” she forces out.
Even though I’m not making direct contact with her skin, I can feel the heat coming off her hot pussy. As the second blow lands on her bottom, she grinds into my hand and instantly pulls back from the cold. “Two, thank you, Headmaster.”
“Better,” I praise, giving her a brief respite from the ice with the next three strokes. On and off, cold and not, through the paddling we go, until finally, all the promised blows are delivered.
My cock is not going to wait much longer, and why the hell should he? Grasping both her pigtails in one hand, I turn Isabella away from the desk and into my body.
“Sit back on your heels,” I command her, still holding tightly to her hair. “You see my erection, Miss Wells?”
“Yes, of course, Headmaster. It’s enormous.”
Her unexpected comment threatens to bring me out of character, and we’re almost through here. I hollow out my cheeks and look over her shoulder for a second, until I can continue without laughing. I give her pigtails a slight tug so she gets the message.
“Damn right it’s enormous. Take it out. Hurry!”
Her fingers fumble quickly at my belt buckle, and I have to concentrate on football stats while she opens my pants and draws down my boxers. My cock pops out and practically begs to be swallowed.
“You want that?” I taunt.
“More than anything, Headmaster,” she answers, licking her lips and putting on a show.
“More than anything, Headmaster,” she answers, licking her lips and putting on a show.
“Tell me what a little slut you are and I might let you have a taste.”
Her eyes darken, and the game is done. “I am such a slut for you, only you. Please let me please have a taste of your beautiful cock.”
With a low groan, I push into her mouth, and she swallows around me.
“Make it good, girl,” I warn, rocking my hips gently but insistently.
Her hands wrap around the base, caressing whatever doesn’t fit in her mouth. I grip tighter around her hair, forcing myself in just enough that we both remember I’m in charge.
I drop my eyes to take in the glorious view—Isabella’s eyes fluttering closed, her eager mouth and hands working me, nipple clamps jangling against my parted legs, all her attention devoted to pleasing me...bringing me off. Just as it should be.
“You are such... a cock slut... little Wendy.” My breathing becomes labored, my hips thrust and retreat, again and again, movements that are less and less controlled with each plunge into her wet, enthusiastic mouth. She picks up speed, tightens her grip, and starts to moan around me.
“Bad girl!” My thighs tighten, and at the last second, I pull out of her very surprised mouth, taking my cock into my own hand and releasing violently. My vision blurs in that delirious lack-of-oxygen moment, and I’m vaguely aware of painting her tits with my cum. I reach back blindly for the desk and manage to steady myself while I ride the orgasm out. Though we’re long past those days when I worried about mentally leaving her, I’m aware on some level that this whole scene has been absent of our emotional connection, and I quickly find her eyes to make sure she’s all right with that.
Isabella/Wendy is sitting back on her heels, covered from neck to belly button with my cum, a look of utter bliss on her face. I’m quite sure mine looks the same way right now. I give one of her pigtails a playful tug.
“I’ve got bad news for you, Miss Wells.”
“What’s that, Headmaster?”
“I have to train you not to like my cock before you can leave here.”
“Well, Headmaster,” she says, barely containing her smile, “I guess I won’t be leaving here for a very, very long time.”
A/N: So it turns out, I was having a bit of a hard time saying goodbye to these two as well. And we all knew we were going to see Headmaster again. (Yes, I know she didn't "get hers" but you heard the wildcat...she's not leaving for a very, very long time!)