Private Tutoring

Written by , on 2022-03-13, genre S&M

Part 1

“This is because transcendental art was itself steeped in Neoplatonic symbolis-'' Ms. Olsen’s lecture was cut short by the bell, announcing the long awaited end of the school day.

When the students were finally gone Tiffany took off her heels and put her tired feet up on the desk to do some much needed grading. Her 12th grade history class that year was the most boring class she had ever taught, and it pained her almost as much as them to watch the minutes tick by, edging endlessly towards the great freedom of 3 o’clock. Only one student was ever engaged, Timmy Coen, or Tiny-Tim as his classmates called him. On top of being the last of his class to turn 18 he also hit his growth spurt embarrassingly late. In fact he had barely any friends his age, choosing instead to spend most of time with the teachers, which only worsened his reputation. He was a doodler, which Tiffany didn’t like at first, but his constant engagement and good grades quickly changed her mind.

“Oh Timmy, what have you done this time?” She said, smiling to herself as she graded an essay of his, decorated with an armored knight and a few dragons. “Hallo, what’s this?” She said turning the paper over.

There was no writing on the back but Timmy sometimes used the space for more elaborate doodles which she liked to see. Only this time there was a more exotic piece of artwork: a woman, remarkably like herself, with curly, brown hair and round glasses with bright blue eyes was sitting at a desk, naked but for a necktie, with her bare feet up on the desk, teaching with a long reed like teachers used in the old days. He had evidently forgotten about the drawing and accidentally wrote his essay on the black side. There was such incredible detail in the face, the breasts, the feet, she was genuinely impressed.

Tiffany put down the essay in shock, “does he really see me like that?” She wondered, not knowing whether to be disturbed or flattered.

She knew she would have to return it next class, what would she say? How should she respond? In the end she decided to simply watch what happened in class, “if it was just a fit of teenage horniness I won’t bring it up,” she decided, “but I don’t want him being distracted in class.” The school teacher sighed and continued grading, setting aside the explicit work to be dealt with at some later time.

The next day Tiffany wore an oxford shirt with a black and white striped tie, just like the one in the doodle, with a black skirt and heels with white stockings. She also found a long, bamboo reed and brought it to class in place of a laser pointer to use on her PowerPoints. Poor Timmy saw what she was wearing and immediately knew she must have found his misplaced drawing. He tried to hide his fair, blushing face but Ms. Olsen noticed and smiled to herself. The boy didn’t speak the entire class, and as the high heeled teacher passed back his essay he read the red words at the top of the page: “see me after class”, then carefully turned it over to see that he had in fact turned in his doodle, but to his surprise Ms. Olsen had written beside it: “+5, great detail!”

When the bell rang Timmy sheepishly went to the front of the class and took a seat by Tiffany’s desk.

“I think you know why I asked you to stay,” she said, Timmy nodded in reply, “I want you to know you aren’t in trouble, I only want to help.” The boy relaxed a little and Tiffany put her feet up. “You seem to be distracted by how you imagine I look under my clothes, would it help if you saw what I really look like?”

“Y-yes ma’am!” Timmy said excitedly as she left to lock the door. Tiffany began to unbutton her shirt, then took it off completely. She then slipped out of her skirt, and one by one the clothes came off until she stood in nothing but her tie. The instructor had a pear shaped body with soft, light skin, she had pointy tits with little brown nipples, a deep navel and a large, smooth ass. The boy could hardly contain his excitement and began sporting a slight bulge in his trousers.

Ms. Olsen smiled at her student, “now Timmy, what should we do about your distraction? You are such a good student and I would hate to see your grades drop on account of this,” she said, indicating to her naked body.

“I’m s-sorry Miss Olsen, it’s just… you’re so g-gorgeous…”

“Oh Timmy,” she blushed, “maybe you just need to release… it’s only natural for a boy your age to feel like this… but you’ve got to get it out of your system. You have a sixth period study hall, don’t you?” Timmy nodded, “good, I want you to see me every day before class and we’ll just get your mind off of my body, ok?”

“Yes ma’am!” He squeaked, “b-but… do you think we could maybe do some n-“

“Tomorrow Timmy, not till tomorrow,” Tiffany cut him short as she began putting her clothes back on. Soon she was fully dressed but for her stocking feet which she put up and a few buttons which exposed her cleavage. Timmy left the room and she smiled to herself, proud of her ingenuity.

Timmy came nervously into Ms. Olsen’s class the next day, she was sitting alone at her desk,

“Come in dear and lock the door behind you,” she said without looking up.

He took off his backpack and went up to the desk.

“Take a seat, Timmy,” Ms. Olsen said as she looked up at him through the tops of her glasses. “Now you seem to be distracted by… that…” she pointed to the twitching bulge in his pants, Timmy blushed and tried to hide it, “oh don’t worry sweetie, that’s why you came didn’t you?”

Timmy found his beautiful, well dressed teacher get up and walk around the desk to his chair, “may I?” she asked, kneeling down.

“Y-yes Miss Olsen…” he hesitantly said.

Tiffany unzipped his pants and pulled out the twitching cock. It was a good size and clean shaven.

“Now I want you to tell me just what you like, I want you to get it all out of your system before class,” she explained slowly, kissing his cock between words.

“A-aahhh… t-thank you M-Miss Olsen… oooh… that feels so g-good…”

The teacher smiled and began to suck on his tip, wiggling her tongue around all the best places, then in one quick motion she thrust her head down to the base of her student’s cock, letting her mature throat squeeze against the sensitive shaft. Timmy felt his cock slip suddenly into her tight, warm throat and started to moan out loud. He tried to stay quiet but the sensation of her throat sliding on and off his dick, her tongue tickling the entire length as it moved made that nearly impossible.

“Quiet baby… we can’t have anyone hearing us,” she whispered as she came up in between strokes.

“I-I’m so sorry, ooaaaah! I-it’s so good…” he moaned.

“If you can’t stop that baby I’m going to have to gag you,” Tiffany said at last, licking tantalizingly around his dripping tip and stroking with her hand.

“Gag me mommy! Stuff my mouth!” He cried.

Tiffany was taken aback, evidently she was helping her poor student release a lot of pent up sexual fantasies. She looked around for something to gag him with, slowly stroking with her off hand. At last she settled on her panties. She took off her skirt and then the lavender panties were wadded up and stuffed into the moaning boy’s mouth. His muffled moaning and little squeaks of pleasure made her wet as she went down hard. Deepthroating the hot and bothered Timmy until at last in a muffled clamor of shouts and moans and please, heh finally flooded her mouth with his virgin cum. Hot, sticky semen dripped slowly down her throat as she pulled his slick penis out of her and swallowed the salty mix.

“There, now I expect your full attention today Timmy, do you understand?”

“Yes ma’am!” Was his cheerful reply as she drew the soaking panties from his mouth and put them on. The wet fabric rubbed horribly against her clit and made her drip, her sweet girl-cum mixing with his saliva to make it even wetter and even worse as she tried to give her lecture. Timmy sat in class with an entranced smile on his face, barely speaking but watching every curve of her sexy body as she taught.

Part 2

After a few days of blowjobs, handjobs and even footjobs, poor Tiffany was at a loss. One day as she was stroking her student’s slippery cock with her oily feet her white socks stuffed into Timmy’s ecstatic mouth, Ms. Olsen began to troubleshoot with him.

“I’ve noticed that these little sessions of ours aren’t having much effect,” she said, running her purple toes slowly over his tip, “I mean… sure you’re getting good grades, but you just aren’t engaging like you used to,”

“Mmphh mph phmphmm,” he mumbled into her saturated socks.

“Accordingly I want to start trying a new strategy: starting tomorrow you will meet me after class and I will reward or punish you based on your engagement, the reward being an orgasm and the punishment being 45 minutes of edge play. At the end of the semester if you get above 90% on your oral participation then we can have full on sex, deal?”

“Mphh mh dlphmm,” Timmy agreed as he felt his body begin to orgasm and squirted his load all over her soft feet.

“Oh Timmy… look at the mess you’ve made! Come here, we have 10 minutes till class, be a dear and clean this up,” Ms. Olsen ordered as she spread her cummy toes.

When Timmy stayed after class the next day, Tiffany took from her desk a silk-rope and a gag.

“Come here Timmy, I told you we would begin a reward system today, well you haven’t really impressed me. Come here and take off your clothes.” She said sternly.

Ms. Olsen was wearing a tight, black dress with high heels and nylons. Her nails were painted scarlet and her lips were a dark, cherry color. She wore contacts instead of her usual glasses and was holding the pink silk in her hands. Timmy obeyed and allowed his teacher to tie him to the chair with his arms behind and his feet resting on the arms so that his entire, smooth torso was exposed. A chord of silk wrapped tightly around his virgin cock and balls, making his penis throb with excitement. A large gag was fitted into his mouth and Tiffany at last began his punishment. She struck his bare feet and thighs a few times with the bamboo stick and watched as his light, boyish skin turned a gentle rose. Timmy trembled with excitement as the painful pleasure began to course through him.

Tiffany smirked and after some time she softly kissed all the pink, stinging flesh until she made it to his cock, but she didn’t suck it, rather she gently caressed and kissed it, slowly licking up and down the throbbing shaft while pope Timmy sat and watched.

“You want me to take off my clothes don’t you?” She said tickling his balls, “but I won’t, so you’ll just have to use your imagination.”

She then took a finger, sucked it a little and gently stroked around the outside of his anus. Timmy quivered with strange, horny feelings as her long finger slid inside of her and slowly began to stroke his prostate as she planted slow, soft kisses and little licks all over his cock. She slowly brought the writhing boy to the edge of orgasm and then with a grin she stopped. Tickling all over his inner thighs, belly and feet with her scarlet nails. She repeated this process over and over again until her 45 minute timer went off. She then gave his aching balls a gentle pat and began to untie him. Timmy protested into his gag,

“Mmphmmhph!” He moaned at her.

“Oh don’t start, you agreed, come back with better participation tomorrow and we’ll see how things go.”

After the poor boy had dressed and left her room, Tiffany spread her feet apart on her desk and began to play with herself. Torturing her favorite student had filled her with such intense sexual energy that she had to release. After a few minutes of fingering herself she softly moaned Tommy’s name as orgasmic pleasures flushed through her body, concentrating in her erect clitoris.

The following class Timmy was extremely attentive. Taking notes and asking questions about nearly everything. Tiffany smiled as she thought about what they would do when class was over. And soon enough the bell rang and the two began their private tutoring session. Tiffany wore a red dress with flats, a choker over her neck and glasses.

Timmy and her smiled as they met in the front of the class.

“You’ve been a very good boy Timmy, and be assured I’m going to reward you!”

The two of them stripped and Tiffany tied her smiling student to his chair. She then slipped the red gag into his mouth and began to tickle his penis and inner thighs, planting light kisses all over him. His anus tingled and contracted as she slipped a finger in to pleasure him from behind, stroking the sensitive spot softly. Then the familiar lips wrapped around his tip as she slid his cock down into her throat. Powerful, electric sensations bounced from his prostate to his tip and back between the tight, wet strokes of her mouth and the vulnerable but gentle strokes of her finger. She edged him over and over again, each time building up more and more throbbing pleasure until with five minutes to spare she let the squirming boy cum in her warm throat. His ass clenched down and contracted with powerful, orgasmic pleasure around her finger as she pulled it out. Timmy and Tiffany were both loving the new system.

When midterms finally came around Timmy was called for a “special meeting” into Ms. Olsen’s office. He slowly opened the door to find her waiting for him in a purple dress, her hair and French nails recently done with heels and fishnets on her feet.

“Hello Timmy,” she seductively said, “you’ve been really good this semester… and I want to reward you with something very special.”

She slowly approached the trembling boy and kissed him on the lips. Timmy nervously reached his hand between her legs,

“It’s ok to touch me, Timmy,” she reassured him.

He felt around and quickly identified a spot that made his teacher gasp and breath heavily when he stroked it, and it wasn't long before she was dripping wet.

“I want to repay you for all the wonderful orgasms you gave me…” he nervously but proudly announced as he knelt down in front of the desk and pulled off her panties, then putting his head between Ms. Olsen’s thighs began to lick and kiss until he found her special spot again. It was a little, sensitive knob that made her moan and squeeze his head when he touched it, like a little pleasure button that soon became the object of every kiss, lick, nibble and hickie he could give. Tiffany bit her lip and tried not to moan, but at last she couldn't.

“What’s that? Ms. Olsen if you can’t keep quiet I’m going to have to gag you!” Timmy said teasingly.

“Hehe, gag me then!” she playfully replied.

Timmy was not unprepared, he soon produced from his backpack a gag with a long phallic extension. Tiffany gulped, but graciously opened her mouth to receive the long, rubbery shaft deep in her throat. They stripped each other and Timmy prudently allowed his teacher to gag him as well. He lay on his back along her desk while Tiffany straddled him and slowly lowered onto his cock. The two moaned loudly into their gags as she began to ride him. His cock slid along the length of her warm, tight pussy, stimulating all her most sensitive places in a rhythmic, heavenly motion. Timmy tickled his teacher’s erect nipples while she bounced up and down, bringing them both closer to orgasm. The sound of each other’s gagged moaning filled the scene with kinky, sexual energy until at last they broke. Tiffany screamed into her gag as heavy throbs rippled from her g-spot into the rest of her body as Timmy felt the tight, erotic contractions around his dick and came helplessly inside her. They removed their gags and kissed lovingly for a while, staying connected as long as possible while their bodies still echoed with the light, post-orgasm contractions and the lingering sexy feelings.


Ms. Olsen and her student passed the year in a similar manner, with lots of edging and orgasms. Tiffany would also sometimes make Timmy pleasure her by sitting on his face or simply bending over and letting him tickle her pussy and clit with his probing, boyish tongue. But at last the sad time came for Timmy's graduation. Tiffany cried as she watched her student process down the aisle in his black cap and gown, with the red salutatorian cords that she helped him to achieve. That evening she drove home to her little studio apartment, dressed in her master’s regalia and decided to treat her tears with a bottle of wine. But just as she was about to pour herself a glass, the doorbell rang.

“Who is it now?” she angrily said.

But to her surprise she opened the door to a long, passionate kiss from none other than Timmy Coen, still wearing his graduation regalia.

“T-Timmy?!” she said in joy and confusion.

“My parents think I’m at a party with my class, but I decided I couldn’t graduate without being with you one last time!” he said as the two collapsed into each other’s arms.

An empty wine bottle later and they were cuddling in Tiffany’s bed together, softly kissing each other’s drunk faces.

“Can I tell you a secret Miss Olsen?” Timmy whispered in her ear.

“Please… I’m Tiff to you now… and yes…”

“Well… Tiff… I don’t have any clothes under this gown,” Timmy said, smirking.

“If I’m being completely honest… neither am I…” she replied playfully.

Tiff’s nipples stood erect as they shed their gowns and entered into a deep, skin to skin embrace. Then Timmy climbed on top of her and began to tease her erect clitoris with his lips and tongue, shoving his shaved cock and balls into Tiffany’s face. She had no option but to take them gladly in her mouth and gently suck on them. They sixty-nined until Tiff could hardly breathe, her clit was a burning, highly sensitive button of sex by the time she found herself putting her bare feet and legs behind her ears. Timmy teased her clit a few minutes with his own burning tip until the couple could stand it no longer and Timmy thrust deep inside his old teacher. It didn’t take long for Tiffany to realize that no one was there, and no one would stop them from moaning their hearts out if they liked.

“Moan… moan baby! Moan with me!” she said ecstatically as her pussy began to pulse with deep, sexual pleasures.

So they began, shyly at first, but soon it grew until the two of them were crying and moaning each other’s names for the first time out loud. Tears welled in Tiffany’s eyes as she heard the sweet, innocent: “T-Tiff… Tiff!” from Timmy’s mouth, all the while she felt the warm, squishy thrusting along all her electrified nerves.

Suddenly he stopped and began slowly tickling her clitoris, “w-what are you doing Timmy?” Tiff said nervously, “I was really close.”

“I know,” she replied with an evil smile, “remember all those times you edged me and edged me and wouldn’t let me cum?” Timmy’s fingers stroked so lightly and quickly over her blazing nerves she could barely stand it.

“Oh FUCK! Why is this so hot? I-I’m sorry Timmy… Please let me cum… oh GOSH plehehese!”

“Hmmm… beg me,” he ordered, staring deep into her eyes as he pinched her clit.

Tiff was so close, all sorts of hormones flushed through her drunk brain as she stammered for the words. At last she laid her head back and erupted into a flurry of pitiful, sexually charged please and exclamations. Then without warning Timmy began thrusting fast and deep inside her and a shock wave of intense pleasure rippled from her throbbing brain to her spreading toes. Tiff lost her mind, screaming and moaning as her whole body shook with a consuming orgasm which gripped tight around Timmy’s thrusting cock. At last he collapsed on top of her, moaning her name and cumming his mind out onto her throbbing pussy and heavy-breathing belly. Timmy reached for the nearby light and they drifted into sweet, dreamy sleep on her bed. In the morning Timmy was nowhere to be found, but a little note on her nightstand informed Tiff that he had gone home so as to not rouse suspicion, he begged her not to be unhappy and promised that it would not be their last meeting. Tiffany walked into her kitchen naked and poured herself a large glass of water and sat down to lovingly recall the wonderful year she had.

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