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The Headmistress's Crop



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Arrington diverted from Cutter’s path back to the Administration building and headed towards Albertson’s office.  When she arrived she found his door open and heard his rapid keystrokes before she was even ten feet from the entry.

“I take it you heard about Mr. Brantley,” Arrington said.

“Yes, I was just typing up my report.”

“Good.  I look forward to seeing it.  I’m here, however, to inform you that you are being suspended.”

“Suspended?” the typing stopped.

“Yes.  We allowed a rapist to freely wander campus for years.  Everyone involved must be investigated and, if necessary, held accountable.  The other Safe Practices Officers that oversaw Mr. Brantley and his submissives will be suspended as well pending an investigation by Campus Safety and the Charenton Police.”

“I…I can’t disagree,” Ryan said.  “I just don’t see what I could have done.”

“There is always something that could have been done,” Arrington responded.  “There are always manners in which to improve ourselves.”  She let the words hang in the air for several seconds until she was confident they had their desired impact.  “However, individuals like Mr. Brantley are as adept at camouflaging themselves as they are at brutality.  Those involved will only be punished for their lack of diligence, not for the heinous acts Mr. Brantley committed.  I am going to recommend to the other governors that you be retrained if cleared.  Do you understand?”

“Yes Headmistress.”

“You may continue use of this office in the meantime.”

The typing resumed before Arrington even turned around and she allowed herself a slim smile at that.  Good.  Albertson was still focused on helping to produce improvements, not wallowing in pity.  She hoped he would be cleared.  He had many good qualities as an SPO.

Unfortunately the others involved were off campus.  She would have to resign herself to e-mailing them, if the Submaster hadn’t done so already.  While his initiative and willingness to step on others’ toes to get something done was often regarded with contempt, she appreciated when he made for less work for her by doing one of her jobs.  She called up her e-mail on her phone and found that was indeed the case.  Her work for the day finished, she switched over to the school’s directory.  It was time to play.




Three short knocks roused Arrington from her position on the couch.  She’d replaced her formal outfit with something more alluring, a black thong, thigh high socks, and a black leather harness that cut a striking X across her pale skin and left nothing else on her upper body covered.

It was a body that barely showed its forty-two years of age, if it did at all.  Time had treated her well.  Her medium sized beasts remained perky, her stomach and legs taught.  Her hair had gained a bit of gray and her face had certainly acquired a certain maturity, but the former was still mostly black, and the latter unwrinkled.  Only her voice gave any indication that she’d seen over four decades, seeming to grow an octave deeper and a touch more powerful with each passing year.  It was not masculine by any means, nor was Arrington for that matter, her command came strictly and exclusively from her femininity.

Her late night suitor blinked as he came face to face with her exposed breasts, his short stature putting them right at eye level.  Arrington leaned against the door and let him fumble about awkwardly for a moment before speaking.

“They’re out for your benefit, so you may as well stare,” Arrington chided.  His eyes nevertheless moved around her, as though magnets were repelling them, at first focusing on her midsection and then dropping to the floor.  She reached a hand out under his chin and raised his head to the appropriate height.  “I do love the shy ones,” she said.  “Are you dressed as requested?”

He nodded, still having trouble figuring out where to look.  “Show me?”  The young man unbuttoned the knee length coat and opened it, revealing nothing beneath.  He hunched forward a little, trying to remain hidden in its confines as it billowed around him.  “Drop it,” Arrington commanded.  “I didn’t say look around, I said drop it,” she repeated as he started to glance down the empty hall.  The coat fell to the ground.  He was not an athlete, or a gym rat, having spent more days in front of computers and sheet music stands, but he certainly wasn’t in bad shape either.

“Come inside and remove your shoes,” she said, turning and giving him a look at her ass that raised his cock several inches.

“Dylan McGuire,” she said, turning to face him once more when she heard the door latch shut.  He stood just inside, his cock standing at half mast, his face and chest flush with embarrassment.  His journey to the university hadn’t been all that different from Ellie’s, though where she had fled an abusive family, he had merely left one that didn’t understand him.

They had been delighted when he’d announced his early acceptance to “one of the Midwest’s premier Christian Universities,” seeing him off at the bus stop with a ten thousand dollar check for his bank account.  Little did they know he’d come to the University de Sade in search of his rightful place at a woman’s feet.

Arrington had been on his mind since the second he’d arrived on campus.  She radiated power, and age, and experience.  He didn’t even need porn to masturbate to, he just got on his knees and jerked off to thoughts of her.  And somehow he felt that she knew it.

Arrington was unlike any woman he’d ever met, certainly unlike the bandmate he’d dated through his senior year of high school, the plump young girl who’d fumbled beneath his boxers to give him the first orgasm that hadn’t come from his own hand but had been too afraid to take his virginity otherwise.  She was a perfectly nice girl, but she was no Domme.

“I believe we’ve found a suitable companion for you,” Arrington said.  It was amazing how she seemed so in control, even in her undress.  Of course it helped that he was even less dressed, and that he’d clasped his hands respectfully behind his back, affording her a full view.  “Hopefully you’ll become quite taken with her when she’s on campus, but until then…” she licked her lips and he felt a pang of fear race through him.  “Until then, you’re too delicious to leave alone.”

“Don’t worry, I will not be taking…certain virginities,” Arrington reassured him.  “It wouldn’t be fair of me to deprive someone of those opportunities.  But I think there is nonetheless quite a bit you can do for me.  Do you understand?”

He nodded.


“Yes Headmistress.”  His cock stiffened.

“Have you masturbated since you’ve arrived?”

He swallowed hard.  Fuck, she knew.  “Yes Headmistress.”

“And have you thought of me while doing so?”

Fuck.  “Yes Headmistress,” he cast his eyes downward.

“Tsk tsk,” she chastised him.  “This must be a real treat for you,” she said.

“Yes Headmistress.”

“Come over here,” she said.  “Closer,” she beckoned when he stopped a few feet away.  “Closer.”  His breathing grew heavy, his eyes were less than an inch away from her chest.  He thought about leaning over to lick her nipples, but he restrained himself.  His cock was so hard it felt like it would burst.  Arrington noticed, dropping her eyes.

“Mmm,” she murmured.  “I do love that I can still get men half my age rock hard in a matter of seconds.”

“Oh fuck!” he gasped.  She’d reached a hand out and taken hold of his balls, kneading and squeezing, and massaging softly.  He felt his orgasm rising, but through sheer force of will he managed to hold back.

“Cute, just like the rest of you,” she said, running her hand up his five and a half inches.  “Kneel for me.”

Dylan complied, and had to fight back another urge to cum as that put his face directly beneath Arrington’s pussy, her scent filling him with the urges he’d felt countless times alone in his own room.  “Remove them,” she said, jutting her hips out ever so slightly.  “Without using your hands,” she added.

Dylan gulped and moved forward, having to strain against his height to reach the thin cord encircling her waist with his teeth.  He nearly moaned and lost his balance when his nose touched her flesh.  She smelled like royalty.  As he brought the thong lower down Arrington’s long slender legs, he felt like a worthless peasant paying tribute to his queen.  When he reached the bottom, Arrington refused to move for a moment, leaving him clinging to the panties, his head hovering an inch above the floor.  He strained his eyes upward, but to his dismay he was too low to catch a glimpse of her now bare pussy.

He felt Arrington shift above him and realized that she was bending over.  His curiosity was brief as the cool metal of handcuffs touched his wrists.  Only then did she allow him to remove the thong completely.  “You are almost properly attired,” she informed him.  She grabbed a black leather collar with a single D-ring off the kitchen table and fastened it around his neck, facing the ring frontward and padlocking it in the rear.

Dylan’s cock dripped precum as he waited in anticipation of Arrington’s next order.  She took note of it, crouching and running a finger up his shaft to catch the drops.  “Open.”  He complied, knowing what was coming next and dreading it.  Arrington rubbed her wet finger on his tongue, producing a grimace, though to his surprise he tasted only the slight saltiness of her skin.

“Not so bad, was it?” Arrington smiled.

“No Headmistress.”

“There is a black yoga mat in front of the couch.  I would like you to kneel there while I tend to some things.”

“Yes Headmistress.”  Dylan shuffled across the hardwood, ignoring the hard knocks against his knees and taking care to not lean too far forward, lest he fall with no means to stop himself.

His wait was brief, though that did little to slow his racing heart or to weaken the strength of his throbbing cock.  When Arrington returned, she sat before him on the couch and spread her legs.  For the umpteenth time Dylan felt his breath leave his chest.

There it was, all that he’d dreamt about, all that he’d stroked himself to, staring him in the face, bare and glistening, exactly as he hoped it would be if he ever got a chance to see it.  “You understand what a gift this is?”

“Yes Headmistress,” Dylan nodded, unable to take his eyes from where he so desperately wanted his tongue.

“Are you going to treat it well?”

“Oh god yes,” he moaned, begging inwardly for his wait to be over.  Before he could react, she extended her leg and wrapped it around his neck, giving him a shove from behind.  With no hands to catch himself he fell forward, panic racing through his chest for a split second before he landed with a soft thwomp on the couch cushion and stuck there at a forty-five degree angle to the floor.

Arrington grabbed his head with both of her hand and took a moment to run her fingers through his curly brown hair.  His cock began to spurt below, but he didn’t care and neither did she.  Before he could even have a chance to apologize, she brought his lips to hers.  He stayed frozen for a moment, trapped in the throes of his orgasm, wishing that there had been a hand to usher it along.  And then he snapped back to life; his tongue found her clit and he began to lick.

“Flat tongue, less aggressive,” she barked out orders and moved his head as necessary, which only served to make his cock attempt to rise again.  “Mm, that’s a good boy,” she suddenly moaned as he found the right spot, and despite his recent indiscretion, that put him right back at full attention.

Arrington loved the younger men.  What they lacked in skill and experience they more than made up for in eagerness, and that was far more important in her opinion.  Dylan had been eying her like an awestruck fan from the moment he’d set foot on campus and eying her like an obedient lapdog from the moment he’d arrived at her door.  His soft full lips were the highlight of his babyish face and she had been looking forward to putting them to use.  As she held his head in place she was glad she had not been disappointed.

She shifted back into more of a laying position so he could look into her eyes while he pleasured her.  Large and blue they conveyed a teenage adulation of the female form.  It was clear the young man was in heaven right then, and as she pressed him firmer up against her cunt, so was she.

She could have cum right then and there, she had long since mastered control of her sexuality, but she didn’t want to.  More specifically she didn’t want to give Dylan the satisfaction of having gotten her off so easily.  Make him work for it.  Make him lick and suck and keep his face buried in her until it became hard to breathe.

She pressed his head down harder, enjoying the increase in sensation as Dylan interpreted the motion as a command to work harder.  Only when he finally started to strain against her grasp, and his chest heaved, and his cuffed hands started to fidget did she allow herself to sink into the pleasures his tongue wrought.

“Right there, up and down, don’t go slower, don’t go faster,” she commanded as she shut her eyes.  Her grip weakened, but Dylan didn’t move, determined to give her what had earlier been ripped from him.

“Mmmmm,” Arrington let out a long low moan as she came, long and slow and hard to match his licks, just the way she liked it.  In truth it was more than a little moan, but she hardly wanted to give him the satisfaction.  Let him think his performance was merely adequate so that he continued to strive for perfection.  His future Mistress would appreciate that.

“My dear boy,” Arrington said, grabbing him by his shaggy hair and helping him to his feet.  “I think you’ve earned a reward, don’t you?”

“I…uh…yes Headmistress?”  He shuffled beneath her grasp, afraid that to say yes would be to assume too much.

Arrington laughed, leading him by the hair through her bedroom and into the walk-in closet she’d turned into a small dungeon.  There was a St. Andrews cross leaning on its stand in one corner that was to become his destination, his wrists and ankles held fast by leather restraints.  She noted with some satisfaction that his short frame forced him to spread wider than a man of average height would have.  She liked him spread wide.  Judging by the way his cock oozed pre-cum, he liked it too.

“Normally I like my submissives plugged for this,” Arrington said, pulling something that Dylan couldn’t see from a tall cabinet along one of the walls.  “But I will not be the one to take your virginity in that regard, so I will have to be satisfied with your cock and balls alone.”

She ran her hands over him, spreading the lube over the length of his shaft until she was satisfied with the coverage.  “How close are you?”

“Pretty close,” Dylan gasped as she began moving her hand up and down.

“How close?”

“I don’t know, uh…oh god…”  Arrington smiled and sped up for a few seconds before stopping.

“How much longer could you have handled that?”

“I don’t know..ungh!”  She’d squeezed his balls.

“How.  Much.  Longer?”

“Ten, fifteen seconds maybe,” he said, breathing a sigh of release and she released him and resumed her slow stroking.

“I don’t expect you’ll keep me entertained for very long,” Arrington said.  “But if you cum too early, know that right next to the bottle of lubricant is a jar of pepper jelly.  Do you understand?”  Dylan nodded.  She squeezed again.

“Yes Headmistress!”

“Good boy.  You’re going to make some lucky upperclasswoman very happy.”  She watched him intently as she stroked.  He averted his gaze at first, and then eventually his eyes clamped shut.  She loved it when they were so under her spell that they couldn’t bear to look at her.  Doubly so when she had their rock hard cock in her hands and there was nothing they could do about it.  She squeezed Dylan’s head on the upstrokes, producing a series of moans from him.  The boy was starting to fidget in his bonds.  It was becoming more difficult to hold back.

“What are you willing to do to be allowed to cum?”

“Huh?” Dylan snapped out of his trance.

“Your orgasm is by no means guaranteed.  I can just as easily ice you into softness and lock you in chastity.  Perhaps I should, given what you did to my floor earlier.”  She slowed her pace.  “So what are you going to do to earn your pleasure?”

“I…I don’t know Headmistress,” Dylan gasped, finding it difficult to speak as Arrington inexorably stroked his cock.  She didn’t even need to stroke fast or hard.  He would get there soon.

“Well you better come up with something,” she said, continuing to stroke.

“Ungh, anything Headmistress, I’ll do anything to cum.”

“How did I know you were going to say that?” the Headmistress purred.  “You’re going to make a mess all over my hand you know…”

“Yes Headmistress.”

“How do you think that should be cleaned up?”  Dylan’s eyes shot open and his face went flush.  He’d never tasted a full load of his own cum before.  He’d pressed his messy fingers to his lips a few times, and had certainly thought about doing more.  But after he’d finished and cooled down, and had the translucent liquid staring him in the face, he’d been unable to pull the trigger.  Too gross, or too humiliating, he could never tell, but too something for him to do it alone.

“I see you know what I’m insinuating,” Arrington said.  “Don’t you?”

“Yes Headmistress.”

“So then how are you going to earn your orgasm?” She sped up.  “Talk fast.”

“I’ll lick it off your hand Headmistress,” he blurted.  “May I cum now please?  Oh god I can’t hold back, may I cum for you Headmistress?  Please?”

“You may,” she said, even though his cock had already started to spurt.

“Ungh, god, thank you Headmistress, thank you Headmistress…” he repeated the words over and over again, even after he’d dropped his large load on her hand and wrist and his cock had begun to grow soft.

“Thank you Headmistress,” he moaned even as she raised her fingers to his lips.

“Open,” she commanded.  He complied, though he didn’t look particularly happy about it.  She loved that.  He winced as she brought her hand closer, and even flinched as she touched his tongue, but as the liquid dripped off her and onto him he relaxed, finding the taste and the texture not nearly as intolerable as he’d been dreading.  “There’s more,” she said, withdrawing her fingers and holding her wrist up so that he could clean it as well, which he did without hesitation.

“How does that taste?” she asked him as she stood.

“Okay…not as bad as I expected,” he said, leaning back against the cross and allowing his limbs to relax.

“It rarely is,” she said, leaving him in his bonds to recover as she went and dressed herself.  When she returned, his cock had shrunk to its flaccid state.  He looked surprised to see her fully clothed once again, but not entirely uncomfortable.  She gave his balls one last squeeze before undoing his restraints.

“I will have your clothes sent to you in the morning,” Arrington said.

“You mean…”

“Yes, you will be walking home naked.  And I will be escorting you.  I can’t very well allow you to traverse the campus alone in your vulnerable state, can I?”

“No headmistress.”

“Your shoes are by the door.  You may put them on and walk ahead of me.”

“Yes Headmistress.”