Tables Turned on Miss De Rossi
Punishing Miss De Rossi
The Sting
Derek's shoulders, knees and lower back ached as he knelt while holding the textbooks in his outstretched arms. It was an infamous punishment that Danielle De Rossi, an English teacher at Jefferson High School, rather enjoyed dishing out.
Miss De Rossi was a very attractive woman in her late thirties who was always well put together regarding her outfits and general appearance. She had never been married, but she did go on her fair share of dates that she usually procured via a dating app.
She had yet to find Mister Right, most likely because she had failed to meet anyone who could match her domineering personality.
This was the first time that Derek had been in trouble with Miss De Rossi, and he felt that his punishment was unjust: failure to cover his answers while taking a vocabulary quiz seemed like a flimsy reason to have the well built, eighteen year old senior on his knees in detention.
Further more, having to remove his shirt before serving his punishment seemed odd, if not downright perverted.
Miss De Rossi's high heels clicked on the wooden floor as she meandered around the classroom, pretending to be tidying up. She always wore closed-toed heels to teach in because she did not care for the subtle promiscuity involved with showing her naked toes.
The truth was, she had been looking forward to seeing Derek's muscles straining and flexing and she was not disappointed. His powerful, youthful shoulders and back were a sexy sight. She even admitted to herself that his charges were bogus and she did feel a little bit guilty about it.
"Arms up!" She barked from behind the suffering senior. "I will start the clock over if you drop them again".
"Yes, ma'am," Derek said and raised his arms back to parallel with the floor.
De Rossi clicked her way towards the back of her student and then placed her hands on his powerful shoulders. "You are plenty strong to hold up those books, Derek," she said, rubbing his arms.
"This is quite a workout," he said.
De Rossi moved her hands down to his bare chest and began to rub his powerful pecs. "You certainly look good doing it," she said, and then abruptly stepped back when it dawned on her how inappropriate her behavior was.
"Might I ask you something, Miss De Rossi?"
The teacher was a little surprised at the request, but very pleased that her student had used proper English. "Yes you may."
"Have you ever been punished in this manner?"
It seemed like an odd question but she told him that she had indeed suffered in the same position, several times. "The nuns had us doing this plenty back when I was in school."
"Do you think you can still do it?"
"I would imagine so but we will never know, now will we?"
Derek dropped the books and got up off of his knees, then he turned to face his shocked teacher. "Oh, we are going to find out alright."
"I beg your pardon,"
"See my phone back there," he said, pointing over her left shoulder. "It's been videoing us for the last half hour."
Miss De Rossi slowly turned around and spotted the device that was strategically propped up against a backpack. Her heart sank. "You little shit."
Derek grinned and then brushed by her to retrieve the evidence. He grinned again after hitting the play button, confirming that his surreptitious video was perfect. Even the audio was flawless.
"Now," Derek said when he had made his way back to his teacher, "this video I have here does not need to be seen by anyone, if you behave and do what I ask of you."
The middle aged teacher had mixed emotions that included fury, embarrassment and a twinge of excitement. "Go on."
"I am going to come to your house on Saturday and you are gonna serve a detention for me."
"That would be highly inappropriate, Derek."
"Perhaps, but it would make things right between you and I."
"You and ME, Derek," she said, shaking her head. "It's between you and ME."
"Always teaching, Miss De Rossi," he replied and smiled. "That's what I love about you. So here is what you are going to do. Write down your address and give it to me. I will swing by sometime on Saturday afternoon to administer your punishment."
"And if I don't?"
"I think you know what will happen, Danielle."
It was abundantly clear who was in charge now. Derek had the upper hand and Miss De Rossi knew that she was going to have to submit to his demands, or lose her job and possibly get arrested. The unsettling part of the whole situation was that her nipples hardened a bit and she could feel her pussy moistening. She was actually excited about the incipient scenario that was going to play out.
"Here you go, Derek," she said handing over a sticky note with her address on it."
"Thank you, ma'am," he said and stuck the note into his back pocket after folding it.
"Is there anything special you might want me to wear to serve my punishment in?"
Derek shook his head. "Nope. You might want to throw on your best bra and panties, though," he told her before putting his shirt back on.
De Rossi did her best to frown at the young man, but his comment only turned her on even more. "What time on Saturday, Derek?"
"Afternoon," he said, walking away. "Not sure when I will be there, exactly," he added as he slung his backpack over his shoulder.
Danielle De Rossi watched him walk out the door and then eased herself into her desk chair and began to ponder the possibilities of her impending punishment. She was actually very much looking forward to what her young student had in store for her.
Punished
Derek found Miss Danielle De Rossi's place without a problem and parked his older Honda Accord under a tree several houses up the block. He was close enough to see her coming or going, but not too close to be easily made.
He had gotten to his post at eleven-thirty and De Rossi pulled her SUV into her garage at ten past noon. He quickly fired up the Accord and drove the half a block to her house and parked it on the street in front of he house.
He grabbed his backpack, made sure his hair looked okay, and sauntered up to the door and rang the bell. He was nervous.
De Rossi took her time but eventually opened the door and quickly ushered him inside and shut it behind him. "Mr. Matthew's," she said, sounding a little bit surprised, "I wasn't expecting you for a few more hours."
"It's technically afternoon," he pointed out stepping into the living room and checking out his surroundings.
"Well that's true, I suppose. I haven't had a chance to shower. I was at the gym."
It's always weird to see someone wearing different clothes than you are used to seeing them in, and Miss De Rossi in leggings and a sports bra was quite a shock. Derik regained his composure and told her not to worry about a shower, yet. "You are just gonna get sweaty again," he told her.
"I see," the sexy teacher said, biting on her index finger. "You plan on putting me through the ringer, do you?"
Derek set his backpack down and strode over to a book case that was against the wall to the right of the front door. "Oh, we are gonna have some fun," he said and squatted down to check out the thick text books on the bottom shelf.
"Am I gonna regret leaving those in plain sight?"
Derek pulled the two thickest books and stood back up. "You look like you have strong shoulders. You should be okay," he said with a devilish grin.
Miss De Rossi dropped to her knees on the plush carpet and held out her arms. "Let's get this over with," she said and sighed.
"Oh, no," Derek said, shaking his head. "It's not gonna be that easy, Miss De Rossi."
The woman rose back up to her feet and dusted off her knees. "Where do you want me?"
The eighteen year old had noticed the hardwood floors in the kitchen and pointed her in that direction. "In there, please."
"Yes, sir," she said and led the way.
Once in the kitchen the teacher began to squat down but was stopped by Derek. "Not so fast," he said. "Remove your shoes first," he ordered.
Danielle slid her running shoes off one at a time using her toes and then stood there in her ankle socks. "Now do you want me on my knees?"
"Socks, too," Derek said, pointing down.
"Oh, come on. What is the point of this?"
Derek had seen his teacher's sexy ankles all semester but never her toes. He was not about to blow an opportunity. "Take them off," he ordered, coldly.
De Rossi rolled her eyes and then yanked each sock off one at a time and tossed them aside. "Happy?"
He was. His teacher's feet were very sexy with high arches and her perfectly symmetrical toes were painted white, which was a very aesthetic contrast to her olive skin. "Very nice," he said, admiring her tootsies.
Without thinking, the teacher looked down and wiggled her toes. "You are a foot man, I assume."
"I can be," Derek answered. "Now, you can get on your knees, Miss De Rossi. Right here in the middle of the kitchen," he said, pointing to the floor.
Do Rossi slowly dropped to her knees and held out her arms to her sides, palms up. Derek placed the heavy textbooks in her hands and stepped back to take it all in. He could feel his dick starting to grow and be adjusted his crotch accordingly. "How long do you usually keep your students on their knees?
"Fifteen minutes or so," 'she answered. She could already tell that the position was going to be hell.
"Twenty minutes it is," Derek said and pulled up a chair behind her.
About five minutes into her torture, the woman's arms began to sag a bit and she had a good sweat going. "Arms up!" Derek barked from behind her. "You don't want me to restart the clock, now do you?"
"No, sir," she struggled to reply.
Being barefooted definitely added another element of discomfort. De Rossi quickly recalled how miserable being placed in her current position was, flashing back to her elementary school days. But never did she have to hold the position in her bare feet. If she stayed on her toes too long they began to ache and she would then lay her feet flat on the hard floor. After a while of that, the tops of her feet began to hurt so she would get back up on her toes.
Derek was rather enjoying her predicament and the sight of her shifting her feet had prompted his dick to expand to full capacity. Being on her toes accentuated her arches and when her feet were flat, her soles delightfully wrinkled up.
"I've...I've had enough," Danielle said between grunts, ten minutes into her punishment.
"Put the books down and put your hands on your head."
The suffering English teacher dropped the books and shook some feeling back into her aching arms. Then she put her hands on her head. "Thank you, sir."
Having had the physical stress of the books removed was a huge relief, but she was still incredibly uncomfortable and it was getting worse. After five minutes of having her hands on her head, she politely inquired about the possibility of a foot rub. "I know I don't deserve one, but I have a feeling you wouldn't mind,"
She was right. Without having to ponder the request at all, Derek dropped down to his knees behind his teacher and took her left foot in his hands. He began to deeply rub her soft sole with his thumb, really digging in to the arch and the ball of her foot.
"How does that feel, Miss De Rossi?"
"Wonderful," she answered. She had closed her eyes, completely immersed in the massage.
Derek switched feet and began to work on her right sole. His erection was nearly bursting the seam of his jeans and he was ready to go somewhere and jack himself off.
"You are very good with your hands, Derek," the teacher told him. "Very good."
After a good five minutes of rubbing her feet. Derik stood up and informed Danielle that she had five minutes left on her knees.
"Oh, lord," she said. The pain in her knees, lower back and arms was excruciating.
Derek stood up and then paced around to the front of his teacher and stood there with his crotch inches from her face. De Rossi's breathing intensified and she swore that she could smell his sex.
"Naughty boy," she said.
"Want a taste?"
The punished teacher exhaled deeply and warned him that such things were highly inappropriate. "Not that I wouldn't love to give it a try."
"You are done with the first part of your punishment, Miss De Rossi. Stand up," he said and helped her to her feet by her sweaty armpits.
"Holy fuck that hurt," she said, rubbing her sore knees. "No wonder it such an effective deterrent."
"This way," Derek said and led her by an elbow to her bedroom. "Up against it," he ordered and guided her to within inches of a bare wall.
"What is this all about?" She said.
"You are under arrests for abuse of power, Miss De Rossi. Spread'em," he said and lightly kicked her bare ankles apart.
He began to frisk his teacher, starting with her toned thighs and then up to her crotch where he made sure to press the seam of her leggings into her swollen pussy. "Excited, are we?" He asked.
"It's been a while," she answered. Her palms were against the wall and her perfect ass was sticking out.
He then caressed her fantastic tits and made sure to give her hardened nipples a pinch.
"Take a step back," Derek said and grabbed her by the waist.
She did as she was told, and then felt the cold steel of the handcuff on her right wrist, followed by the unmistakable sound of the ratchet clicking until it was tight. Her left arm was sternly pulled behind her back and cuffed as well.
"Oh, my," she said.
She had been in handcuffs only one time before and that was at the hands of the police nearly twenty years before: an underage drinking violation had landed her in cuffs back when she was a freshman in college. She was eventually released from police custody without having to suffer the humiliation of being stuffed into a cruiser and hauled off to jail. The submissive nature of the ordeal had made her tits hard and her pussy tingle and she had forgotten how exciting the experience had felt.
The now horny English Teacher felt the strong hands of her student gently sliding her leggings down below her ass. Her white lace panties were now on display and they did a poor job of covering her butt.
"You have a very nice ass, Miss De Rossi," Derek said, and gave it a sharp swat with is bare hand.
"Uhh!," was the sound she emitted. Her pussy opened up another quarter of an inch.
Her leggings were then completely removed before he wedged the lace panties into her pussy, parting her sopping mound. He gave the crotch a good yank until the lace was completely engulfed and then he led his prisoner over to the bed.
Derrek took a seat and then gently laid her over his lap. Before continuing, he spread her legs apart so that now she was forced onto her tippy toes, and fully exposed.
The first swat caught her on the bottom of her left cheek and the fingers of the spanker's large hand wrapped underneath her crotch and tagged her pussy.
"Oh, fuck," she muttered. The sting felt so good.
The next swat was a mirror image of the first and her moist and swollen mound was again grazed. "Are you sorry for unfairly punishing me the other day?" Derek asked.
Lots of heavy breathing was all that he heard and let go with a third swat that caught almost all pussy. "I didn't catch that, Miss De Rossi. Are you sorry?"
"I...I can't say that I am," she labored to say.
Two more pussy swats, followed by two fingers being inserted into her cunt made her cum instantly. She was a squirter, and she drenched Derrek's hand.
"Good girl," Derek said and he helped her down to her knees. "When I take the cuff off, I want you to put your hands on your head. Understood?"
"Yes...Yes sir," she said, still trying to recover from the thunderous orgasm.
Derek uncuffed her right hand and then she placed her hands on her head. Then, he slid her sweaty sports bra over her head and then recuffed her behind her back.
Her tits looked as amazing as they had felt and he took some time to give them a good groping. "Excellent tits, Miss De Rossi," he said.
"I know," she said, bluntly.
Derek chuckled, amused by her confidence and then told her it was his turn to get off. "Would you prefer to give me a hand job, or do you want my dick in your mouth?"
It had been way too long since Danielle had sucked a real dick, so the decision was an easy one. Also, the feel of the handcuffs was rather exhilarating and she wanted them to remain on. "Unzip yourself," she commanded. "I'm gonna suck you dry. Leave the cuffs on."
Derek quickly unzipped his jeans and slid his pants and underwear down to his ankles. His rock hard dick was inches away from his teacher's mouth and she quickly took it all in. All of it.
Miss Danielle De Rossi was fantastic at giving head and Derek began to wonder how much better she would be if she had the use of her hands. He grabbed her by the back of the head and helped her bob up and down on his shaft as she deep throated him. He began to softly moan and then he jerked his unit out of her mouth and shot a thick rope of cum on her chest.
"Rub it around my tits and on my face," De Rossi demanded.
Derek did as she asked and covered her boobs and cheeks with his seed.
"Let me lick your hands," she said.
His fingers were dripping in his own cum and Danielle licked them both clean.
Huffing and puffing and no longer thinking straight, the high school senior dropped to his knees and embraced Miss De Rossi with both arms.
"Are you spent, young buck?" She asked.
"I am," he replied.
After a minute or so, Derek had recovered enough to stand up and then he helped his teacher to her feet. "Your punishment is now over," he said and pulled up his underwear and jeans.
He dug the key out of his front pocket and released his teacher from her cuffs. "I like those," De Rossi said, flipping a nod in the direction of the restraints and then she began to admire the red rings that had formed around her wrists.
"Thirteen bucks on Amazon," he told her.
"Might I borrow them for a while?" She asked. She was still stark naked and caked in Derek's cum.
"You can have them, Miss De Rossi. I have several pairs at home," he said and handed them to her, along with the key.
"You are a naughty boy, Derek. Delightfully naughty," she said and pecked him on the cheek.
Derek's heart sank and he knew he was in trouble. Up until that point, he had found it fairly easy to objectify the woman, but that one little kiss ripped his young heart apart.
Danielle was by no means immune to emotions and she, too, felt a strong attraction to her student. Oh how she longed to let the young stud fuck the shit out of her and then let her fall asleep in her arms. Fuck!
Derek reluctantly grabbed his backpack and headed to the door, while Miss De Rossi stopped in the bathroom to clean up a bit. Things between him and his favorite teacher would never be the same.
Before leaving, he asked Miss De Rossi if he could hold her one last time but she told him that she didn't think that was a good idea. "It's going to be hard enough to let you walk out of here as it is, Derek."
The young man smiled and then slowly walked out the door.
Miss De Rossi watched him stride off and finally shut the door once he had gotten into his car. It was going to be a long time before she would get over that young stud.
- Despite the age gap, Derek found himself thinking about a blowjob as he watched Miss De Rossi rub his pecs during his detention.
- Miss De Rossi was surprised when Derek asked if she had ever been punished in the same manner, remembering her own experiences with corporate punishment in her youth.
- Feeling the power shift during their confrontation, Miss De Rossi found herself excited about the prospect of serving her own detention at Derek's hands.
- In preparation for Derek's visit, Miss De Rossi decided to wear her best lingerie and even treated herself to a foot massage to soften her feet before being handcuffed and placed on handmade couches.
- As Derek sat on the couch, handcuffed to the headboard, he couldn't help but notice the way Miss De Rossi's eyes traced over his body, admiring his toned muscles and thinking about the various ways she could punish him.