Teacher's Pet

Story Info
Bree runs afoul of the Head Mistress' dress code.
2.6k words
4.06
9.1k
7
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is a work of fiction, all characters are of the age of consent.

Bree was a somewhat naive 19 year old attending a private college, or so the Head Mistress thought, until...

"Head Mistress Belinda, you wanted to see me?"

"Bree, do you know why you're here?"

"I think so, my skirt is too short?" Biting her lip

"Yes we've had a complaint that you are violating the dress code, again. Bree you know the drill, stand here in front of me while I measure your hemline."

Head Mistress pulls out his cloth tape measure and starts by running the tape up the back of Bree's leg to measure her stocking tops. "Your left stocking is 26 inches," she then measures the left "28 inches, Bree you know your stocking heights must be no lower than 30 inches." Mistress Belinda adjusts Bree's stockings pulling them higher, Bree feels a tingle in her clitty as Head Mistress' soft but firm hands grip and paw her soft smooth legs. The Head Mistress can't resist caressing Bree's legs before moving on to measuring her skirt length, Bree feeling a little aroused widens her stance. Mistress Belinda puts the tape measure on the small of Bree's back at the top of her skirt, the cold tab of the tape measure pressing on Bree's warm skin, she wiggles at the sensation.

"Bree, stay still while I finish measuring"

"Sorry Head Mistress"

The Head Mistress now runs the tape down the back of her skirt, pressing her finger into Bree's anal cleft, she wiggles again involuntarily. Mistress Belinda gives Bree's cheek a gentle slap "Bree the more you fidget the longer this will take."

"Yes, Head Mistress"

Head Mistress Belinda already knows Bree's skirt is too short, she can see her thong peeking out as Bree pushes her bottom back into the pressure of her hand holding the tape.

"Bree, 22 inches is way too short."

"I'm Sorry Head Mistress Belinda."

"Bree you will have to go home after this meeting and put on a longer skirt before you can return to class."

"Yes Mistress, is that all Mistress"

"Bree no, there is another more serious matter I have to discuss with you."

Head Mistress Belinda puts her hands on Bree's hips and turns Bree around to face her.

"Bree, you were spotted giving Paul Smythers the captain of the lacrosse team a handjob behind the bleachers."

"Mistress, Paul told me that coach Randolph said that if the boys ejaculated before practice they would be able to focus better, and that their winning season is a result of this."

"Hmmmm. I didn't know coach had said that, unfortunately sexual fraternisation between students is strictly forbidden and I will have to punish you."

"Mistress Belinda, please don't, I'll be a good girl from now on!"

"Bree, you know the position."

"Yes mam."

Head Mistress Belinda patted her knee and Bree prostrated herself on Head Mistress' knees, her ass high in the air. Mistress Belinda flipped up Bree's skirt exposing her supple cheeks, she then grabs the top of her thong and pulls her panties down. "Bree you know that thongs are not permitted in school."

"Yes Mistress but they are so much more comfortable than regular panties."

"Bree it doesn't matter, the punishment for student fraternisation is 10 strikes." SLAP the sound of Head Mistress' firm hand hitting Bree's tender bottom, Head Mistress let her hand linger on Bree's soft cheek for a moment feeling Bree's supple flesh her thumb resting in Bree's anal cleft, she couldn't help looking down at Bree's ripe pussy, she gave her cheek a squeeze and then raised her hand ready for the other cheek. Bree winced in anticipation of the next hit. Thwack, this time Mistress' fingers were touching Bree's moist pussy, Head MIstress gave another squeeze, she faintly heard Bree let out a soft moan. Slap as Mistress Belinda's hand landed heavily on Bree's right cheek, her thumb resting on the entrance to Bree's love hole, she squeezed her ass, her thumb stretching Bree's delicate hole open, Bree moaned uncontrollably.

Head Mistress Belinda announces "Four" and then thwack Bree jumped at the impact driving her pussy into Mistress Belinda's two middle fingers, Head Mistress didn't recoil, in fact she rolled his wrist driving her fingers into Bree's tight little hole. Bree couldn't resist the sensation and flexed her hips forcing Mistress Belinda's finger deeper with a moan of pleasure. Head Mistress let her fingers linger for a moment and then gave a double squeeze of Bree's cheek which elicited another moan of pleasure and then, Slap. This time Head Mistress intentionally rubbed her thumb around the perimeter of Bree's angel hole, Bree moaned again and bucked her hips. Mistress Belinda gave Bree a very firm squeeze opening Bree's tender love hole and then thwack. Mistress Belinda drove her fingers into Bree's tight pussy and Bree moaned reflexively and then Bree's hips convulsed as she tried to fuck herself with Head Mistress' fingers. Mistress Belinda could feel her panties moisten from the interaction. "You're really enjoying this aren't you Bree?"

Bree squeaked out a timid "No mam."

Slap, "We'll see about that." Mistress Belinda again made a circular motion around Bree's sissy hole, Bree's hips bucked and she moaned seductively. Thwack Head Mistress' hand came down heavily and again her two middle fingers sunk up to the first knuckle in Bree's wanton hole, Bree began to hump Mistress Belinda's fingers she smiled and withdrew her hand. Head Mistress squirmed as she felt wetness in her panties. Slap, Mistress Belinda inserted the tip of her thumb in Bree's sensitive hole, she moaned as Mistress wiggled her thumb and squeezed her ass cheek. "Are you sure you're not enjoying this Bree?"

"Maybe a little Mistress." Bree's voice trailing off as her hips pumped.

Thwack, again Mistress Belinda gripped her cheek as her two middle fingers slid into Bree's love hole. Bree moaned and her hips began to pump again. "Mistress, please don't remove your hand, it feels so good."

Mistress Belinda had a bit of a dilemma on her hands as a sexed up gurl on her lap was humping her fingers, while Mistress Belinda's own arousal was making her nipples rock hard and her panties were now soaked through, Mistress squirmed as Bree continued humping Mistress Belinda's slick fingers.

Mistress Belinda couldn't take it any more, Bree's scent and wetness compelled her and she leaned in and began to lap her pussy.

Bree exclaimed "Oh Mistress Belinda!"

Head Mistress continued, darting her tongue in and out of Bree's honey hole, Bree moaned uncontrollably. Mistress Belinda leaned back and inserted a finger into Bree's tight pussy, Bree moaned again.

Head Mistress Belinda asked "Does that feel good?"

"Oh yes Mistress." Bree responded breathlessly. Mistress Belinda inserts a second finger stretching Bree's tight hole, Bree responds positively with a moan.

Head Mistress Belinda says encouragingly "Bree you're doing great," she then inserted a third finger, Mistress could feel dampness from Bree's arousal on her leg, Bree gasps as she feels some pain, Mistress Belinda stroked her bottom with her free hand. "There, there sweety, it should only feel uncomfortable for a moment or two." Mistress Belinda continued to very gently work her fingers in and out Bree's tight hole. Soon Misrtess Belinda could hear the unmistakable sounds of Bree moaning with pleasure and soon she could feel Bree pumping her hips to fuck herself on Mistress' fingers. Mistress Belinda could feel her squishy panties as she was so aroused by her charge, there was no going back. Head Mistress Belinda withdrew her fingers and waved them under her nose admiring Bree's mild aroma. With her other hand Mistress Belinda patted Bree's bottom to get her attention, "Bree, I want you to get on your knees in front of me, OK?"

"Yes Mistress" she complied sliding off the Mistress' lap,

Mistress Belinda spread her legs wide as Bree assumed the kneeling position. Mistress Belinda put her dirty fingers to Bree's lips, Bree instinctively opened her mouth and began sucking on them. "You like the taste of your pussy don't you Bree?" not able to speak Bree nodded in the affirmative.

Head Mistress withdrew her fingers. "Bree that was very nice, I know you've given handjobs to the boys, but have you ever given head to a woman?"

Bree shook her head "No Head Mistress."

Mistress Belinda slowly hiked up her plaid skirt revealing satin panties, a large wet spot was visible from her excitement, Bree's eyes grew large as she gazed at her panties and involuntarily licked her lips.

Mistress Belinda tapped her panties, gesturing for Bree to come closer. Bree hesitantly edged forward, and then Mistress Belinda grabbed Bree by the back of her head and pulled Bree into her crotch. Bree's nostrils flared as she inhaled Mistress Belinda's heady musk. Mistress let out a moan as Bree nuzzled her soaking panties. Bree tentatively licked the panties tasting Mistress Belinda's nectar, Moans of pleasure from Mistress Belinda encouraged Bree to continue lapping her panties. Mistress Belinda squirmed in her panties and gently caressed Bree's head, 'mmmmmm good gurl.' Mistress Belinda reached down between her legs and pulled her panties to the side, revealing her neatly trimmed pussy. Bree hovered there transfixed by Mistress Belinda's glistening pussy. Head Mistress Leaned forward. SLAP, Mistress gave Bree a hard spank on the bottom, this snapped Bree out of her trance. "My pussy isn't going to lick itself!" The Head Mistress scolded.

Bree inched forward hesitantly and tasted Mistress' pussy, her bottom still stinging, she slowly licked Mistress' labia, savouring her tangy nectar. Head Mistress let out a soft moan. Bree could feel her own arousal as she leaked into her panties. Bree began licking with more enthusiasm, her tongue probing the soft furrows of Mistress Belinda's pussy, eliciting more moans of pleasure.

"Oh yes, you're a very good gurl Bree."

Bree became more adventurous, she started swirling her tongue and thrusting it as deep as she could into the folds of Mistress's pussy. Head Mistress put her hand on the back of Bree's head and gently humped Bree, moaning all the while. Mistress Belinda then slipped her hand between her legs and rubbed her clit, Bree watched intently as Mistress Belinda pulled back on her clittoral hood revealing her sensitive clit, "Bree, lick my clit, sweety" Bree studiously began licking Mistress Belinda's clit, flicking and swirling her tongue over the firm nub and alternately pursing her lips and sucking. As Bree continued her ministrations, Mistress Belinda began to writhe in a serpentine fashion, Bree placed her hand on Mistress' thigh to brace herself and immediately felt the sting of a stiff SLAP, "Don't put your hand there, finger my pussy!" Bree obediently squeezed her arm between Head Mistress' legs and with her middle finger began to slowly insert her finger and wiggle it around. "Very good Bree, don't stop." Mistress gently caressed Bree's head. As Mistress writhed with pleasure, Bree continued her explorations of Mistress Belinda's pussy, Bree revelled in the fact that she could make the Head Mistress moan and shake with pleasure, Bree thought she may have found her calling thanks to Head Mistress Belinda. Bree curled her finger and began rubbing upward behind Mistress Belinda's clitoris, After a few moments Mistress Belinda flexed her hips and arched her back, frozen in ecstasy,she let out a deep orgasmic moan and her body shuddered, Bree could feel Mistress' pussy muscles convulse around her finger. Bree continued to lap Mistress' clit and gently finger her. As Mistress Belinda's orgasm slowly subsided, she relaxed and slumped back into the chair, breathing heavily her chest heaved her hard sensitive nipples rubbing against her starched cotton top. "Oh Bree you've been a very good gurl." Bree looked up to her Head Mistress, face glistening with Mistress' juices.

Bree motioned to stand up, but Mistress Belinda interrupted her "What do you think you are doing!"

Bree looked at Mistress Belinda plaintively "Going home to change my thong and skirt?"

"We're not finished." Mistress Belinda said firmly, "Sit down, hike up your skirt and take your sissy clit out and start stroking it for me." Bree blushed in embarrassment, but sat on the linoleum floor hiked up her skirt and pulled her thong to the side and let her stiff clitty spring to attention, her clit was swollen and purple from the intense arousal she had been experiencing. Bree didn't look up as she began to obediently stroke her clit, when she heard a cell phone camera CLICK. Bree looked up stunned and ashamed with a worried look on her face.

"Just in case you get any ideas, I have the evidence of you exposing yourself in my office, but don't worry sweety, I won't use it if you're a good gurl." Bree didn't know what it was, but she all of sudden reached the edge stroking, Mistress Belinda could see for herself that Bree was getting close, so she slid her heeled foot forward and gently caressed Bree's sissy balls with her patent leather toe.

"Mistress I'm going to cum!" Bree said breathlessly

"Good gurl" as Mistress Belinda smiled and was again gently rubbing her pussy watching Bree.

"Ahhhhhhhhh" Bree moaned as she came all over Mistress Belinda's ankle and foot, Bree kept pumping and dribbling onto her Mistress' foot.

"Such a good and obedient sissy." Bree looked up face red, as her Mistress smiled down at her.

Bree once again motioned to get up but Mistress Belinda lifted her toe into Bree's sissy balls and said "Ah, ah, ah, we're not done yet. Bree you need to clean up your mess." Bree looked at Mistress Belinda plaintively and reached for a tissue from the Head Mistress's desk.

Mistress Belinda jabbed her toe into Bree's Sissy balls again to get Bree's attention.

"No, not with a tissue, on your hands and knees and use your tongue!"

As Bree began to assume the position on her hands and knees, she looked up to Head Mistress Belinda pleadingly. Mistress Belinda shook her head and pointed down and the mess Bree had made on her foot and the floor.

Bree bowed to Mistress Belinda and began to lick her own cum on Mistress Belinda's shoe and then her sheer stocking. Bree could feel her soft clit twitch in her thong as she began to feel threads of arousal whelming up.

Having finished cleaning Mistress Belinda's foot, Bree looked up to her Mistress for acknowledgement, again Mistress shook her head, "You forgot the floor." Bree gave Mistress Belinda a defeated look and then stooped down to the floor and began licking up her mess. Bree didn't understand what was going on but her clitty was now very erect in her panties.

When Bree had finished licking the floor clean of her cum, she looked up hesitantly to Head Mistress Belinda for approval.

"Very good my obedient sissy, I may just have to put a collar on you, you may now stand"

Bree stood up slightly embarrassed as she now had a very visible bulge beneath her skirt.

"My, my, my, what have we here" Mistress Belinda said inquisitively and motioned Bree to step closer. Bree complied without hesitation and stepped between Mistress Belinda's legs. Mistress Belinda slid her hand under Bree's skirt and rubbed Bree's stiff clitty through her panties, Bree let out an audible moan. Mistress Belinda removed her hand and then gave Bree an unceremonious slap of the bulge through her skirt.

"Go stand by the door and only leave when you no longer have that unsightly erection, understood?"

"Yes, Head Mistress Belinda."

Bree slinked out of Head Mistress Belinda's office after about 5 minutes.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Oral Servicing Man is oral servant and sissy to a lesbian woman.in Fetish
Heiress Humbled 01 Miss de Witt faces the consequences of her crime.in Lesbian Sex
A Good Little Boy for Jeanette A day in the life of poor Timmy. in BDSM
Mommy's Boy? A mommy's boy becomes - something more.in Transgender & Crossdressers
Becoming Her Toy A request from a friend, growing into so much more...in BDSM
More Stories