“Michael, you understand my position, right?” Principal Daniels said, coming around her desk.
“Conversations like the one you had between you and Mrs. Cherry are highly inappropriate.”
Michael kept his head down in his lap along with his hands. It was pathetic, he knew, that despite him being an 18 year old man and a senior in high school, as he sat now in the principal’s office he felt like a child. He could only imagine the awkward conversations he’d have to have with his parents when they inevitably found out.
“Well, I—I understand,” he stuttered. “But I just want to make sure you’re clear that nothing happened between myself and Mrs. Cherry… other than a few texts which you seem to have already…” Michael released a long sigh. “But Mrs. Cherry never—I initiated it all. It’s not her fault.”
Principal Daniels smiled sheepishly and pursed her lips as she scooted between Michael’s knees and the desk, leaning her butt against the edge of her desk. Michael knew this was the last place his head should be but he couldn’t help but steal looks at the black fishnets his Principal wore. How they choked her thighs and disappeared beneath her black pencil skirt. The dark gray jacket she wore over her red blouse was like waving a red flag for bull to Michael. He was doing all that he could do to think about anything else other than her thick breasts that formed a perfect line of cleavage. Her dark auburn hair flowed over her shoulder and pouty lips smirked down at me from her position of authority.
God, what I would give to watch Principal Daniels eat an ice pop… it’s hot out… perfect temperature for an ice—for the love of mike, Michael. Stop thinking about sex for five seconds!
“…Well, what do you think about that?” Principal Daniels asked.
Fuck.
“I’m sorry, Principal Daniels. What did you say?” Michael asked, feeling the heat flood his cheeks like she could read his mind. It was Friday after school and he had just been caught sexting his teacher, Michael really needed to focus.
The corners of Principal Daniels’ dark red lipsticked lips curved upward slightly. “I said, we’re going to have to have a group sit down meeting with you and your parents. And… I’m likely going to have to fire Mrs. Cherry. Maybe even submit the text screen shots to the police…”
“But we didn’t do anything… and I’m 18—I…” Panic seeped into Michael. He really didn’t want to tell his parents about his sexting… not to mention the dick pic he sent his teacher. But more than that he didn’t want to ruin his Science teacher’s career. Mrs. Cherry was a nice lady and she was just starting off in her job.
I mean, she’s 27 years old. Just graduated with a masters in teaching. If she got fired her life would be ruined. And Principal Daniels doesn’t even know about Mrs. Rodriguez’s involvement, yet.
“Is there… Look I can do extra assignments, or community service, or anything really, just don’t punish Mrs. Cherry. Please,” Michael begged.
“You’re a sweet kid,” Principal Daniels admitted, uncrossing her legs. She reached behind her, picking up Michael’s cellphone on her desk and began swiping through the screen. It was the same phone that had screen shots of Michael’s sexting. As well as containing several dick pics and half nude images of his abs and chest. A playful grin came over her face as she looked at something she liked.
“You’re pretty horny, too.”
Principal Daniels’ eyes flicked to mine before returning to the screen they must’ve seen the utter panic in my expression.
How the fuck am I supposed to respond to that?
“Um… yeah… Sorry?” He said but it sounded more like a question.
“The problem, Michael, is if I don’t respond to this appropriately, 1. I could get in trouble. And 2. How do I know that you won’t just keep doing this with Mrs. Cherry? Or another one of our teachers in this school?”
Michael was thinking fast on his feet, which he was terrible at. What is she looking for?
“Well, for one thing I have not told anyone nor would I because I don’t want Mrs. Cherry in trouble… or or… you. Also, I’ll-i’ll just-I won’t date or talk to anyone in this school. I mean, this is my senior year. I am graduating soonish.”
“I suppose, I could trust you… that is if I knew you had an appropriate way to stay honest, lets say… keep your mind out of the gutter…”
“Sure, sure,” Michael nodded, having no idea what she meant. He also tried to ignore the fact that he was not being totally honest with his principal, either.
“A schedule… maintenance of your needs, perhaps,” she said, setting the phone down.
“Of course, if that’s what it takes, I’ll do it,” Michael nodded.
Principal Daniels smiled as she stood straight, looking down on her pupil. “Excellent, dear. Then take off your pants.”
…One Week Earlier…
Michael didn’t mean to snoop. It wasn’t in his nature. He thought of himself as a typical horny teenager—but a good hearted, horny teenager… if that was a thing. Instead, he walked to Mrs. Cherry’s door out of concern for her, or at least that is what he will forever try to convince himself of from then on. The lights were turned off to the short hall that led to a half a dozen classrooms before coming to a set of doors that exited to a back courtyard.
None of the classrooms were used for last period so it was common for this hall light to be off, but it was strange to hear any noise that way. And stranger yet to hear ‘that’ noise. It was something between a yelp of pain like a dog would make and… Michael wasn’t sure… perhaps, a loud TV or singing?
Rustling noises led Michael straight to Mrs. Cherry’s door. He crept quietly there and when he heard giggling near the closed door, he knew he should turn away but he didn’t peeking inside the corner window. Michael saw a dark classroom with the lights off and the shades drawn but there was movement inside. Michael cupped his hands around his eyes to the glass and instantly knew what he saw.
Mrs. Cherry, the blond curvy bombshell she was, was lying on her back on her desk at the front of the room. Her legs spread wide as her thick pale thighs were open for the person between them. Her white blouse she wore that day was still on but barely. Unbuttoned and dangling off the back of her shoulders, Mrs. Cherry’s breasts were completely exposed as she rolled her own nipples between her fingers. It was then that Michael saw the person with their face buried between Mrs. Cherry’s thighs was not only a woman, but another teacher.
Mrs. Rodriguez?
The moment was more stunning than anything at first. Michael was literally frozen in place at the sight. He knew he shouldn’t be watching this but he also thought they shouldn’t be doing this in the school and in a classroom. It was a weak rationalization but one that was enough to keep him watching. Seconds turned to minutes and his eyes adjusted to the darkness. He watched Mrs. Rodriguez’s head bob with her black hair tied back in a bun as her tongue made long laps on her co-worker’s pussy.
“Oh… Oh… Oh yes… don’t stop…” Mrs. Cherry’s words were barely audible through the glass but Michael could see his anatomy teacher throwing her head back in pleasure. Michael felt his cock swelling in his jeans. If it wasn’t for—well, a lot of reasons—Michael probably would have been jerking himself at that moment.
Michael leaned back and looked left to right in the hallway to make sure no one was there and no one was. The last of the buses had left by now so the few students left would be in the gym, outside, or in one of the rec. classrooms on the other side of the school.
When Michael’s eyes turned back to the window his heart dropped to the bottom of his stomach. His movement must have changed the lighting in the classroom from the window and caught the attention of his teachers. The two women were both turned around staring at Michael. There was no doubt. Michael stepped back a step and considered running, hiding, anything to avoid whatever punishment was coming his way.
Too late…
The door snapped open and while Mrs. Cherry scrambled to button her blouse up, Mrs. Rodriguez snatched Michael by his shoulder harder than any teacher had ever grabbed him and pulled him into the classroom, shutting the door.
…One Week Later…
“You heard me—that is if you want to continue down this second option that avoids the punishment—but it’s up to you. You are an adult now, after all,” Principal Daniels said.
Did the principal really mean for him to take off his pants right here in her office? Is this a trick?
Michael sat frozen in place. This was like the ultimate test of being put on the spot and having no clue what the right answer was. In the span of a few seconds his mind moved at warp speed. Playing out the consequences for saying ‘no,’ or what would happen if he went to the bathroom and took off his pants vs if he took his pants off there in her office.
Michael glanced behind him and confirmed her office still had no windows that were viewed out in the offices. There were a few windows that overlooked the grassy field and woods behind the school, but Principal Daniels’ office was on the third floor so no one could see in.
Principal Daniels continued to stare down on Michael like a scornful woman full of punishment just waiting to be disobeyed. Her gaze was hard and unwavering like Michael had never seen before.
Slowly, Michael unbuckled his belt, unzipped his jeans, and unbuttoned them, leaving enough time between each task for Principal Daniels to stop or protest or say that she was joking only for none of those things to happen. With one last exhale, Michael pushed down his jeans to his ankles leaving only his gray boxers on. Feeling more exposed than Michael had his entire life, he sat there uncomfortably.
“Boxers, too…” she said with an innocent curiosity in her eyes.
Not wanting to back out, he did as he was told and realized his cock was standing half hard already from the strange moment.
“Hm. You’re pretty large for an 18 year old man,” the Principal said, with a playful smirk in her voice.
Principal Daniels reached between Michael’s legs and let her fingernails gently drag up the base of his shaft to the tip. She did this twice and on the third pull she wrapped her fingers around his throbbing young cock and stroked him slowly up and down. Almost immediately his cock oozed pre-cum in anticipation of what would come next. Up and down her fingers stroked his shaft continuously until he was relaxed in his seat. His gaze finding her bouncing breasts that jiggled beneath her blouse.
“Stand up,” Principal Daniels commanded with such authority that Michael no longer ran through an internal monologue questioning his response. He just acted and stood. “Good boy, now lay down on your back.”
When Michael did this he felt even more exposed. His throbbing erection bounced about, pointing in the air as drips fell from his tip. Carefully, Principal Daniels walked around the outline of his body. Her black high heels clacking with every step as she walked. When she stopped over his head, Michael’s cheeks flushed as he could see up inside her near pencil skirt. Though dark, there was enough light for him to tell that she wasn’t wearing any underwear.
“Hmm… you like that view? Judging by the stream of cum dripping from your shaft you like it quite a bit.”
“Y-Yes,” Michael managed.
Lowering herself into a feminine squat with her thighs together aim to the side, Principal Daniels hiked up her skirt as she slid them up over her waist. There was a playful smile as she looked down on the boy. Strands of loose hair brushed across her face as she hung her face over Michael’s face.
Principal Daniels opened her legs once the bottom of her skirt was above her waist. The warm energy radiating from between her thighs touched his face and the arousing aroma of her sex touched his lips and nose. Michael found his cock throbbing and his mouth watering. He had never gone down on a woman before. He’d watched videos on it before—plenty of porn that he thought he understood like every teenager, but he never had been this close.
Michael saw the glistening slit of his principal’s vagina near his face until she took a knee beside his face.
“Open your mouth, stick out your tongue,” Principal Daniels commanded. There was no caring left in her voice. There was no teacherly, parental watchfulness in her words. There was only command and dominance, and Michael obeyed.
Principal Daniels put her other knee down on the opposite side of Michael’s face and with his tongue sticking out, Michael tasted the warm wet slit of his principal. Slipping his tongue inside her vagina he felt the walls of her pussy around his tongue as he pressed deeper. Making long laps from the top to bottom of her pussy.
“Ooohhhh… dear….” Principal Daniels hummed and a shudder went through her body. “Mmm… yes, just like that.”
With encouraging words, Michael lapped at her pussy again and again. Each lick pressed harder on her lips and pushed deeper inside her pussy. The warm, electrifying taste that he found peculiar at first soon became intoxicating as he tasted more of her juices flowing from her lips.
“Ohhhh, yes… Michael… just like that…” Principal Daniels growled as she began to force her hips down on her student’s face. “Good boy… just… like… that…ahhhmmm…”
Suddenly, Michael found himself ravenous for her pussy. Satisfying his principal wasn’t enough, he wanted her to be pleased. He wanted her to cum. Raising his palms to Principal Daniels’ upper thighs, Michael gripped the older woman’s body in an attempt to pull her further down on his tongue. His move was greeted quickly by Principal Daniels’ hands shoving him away, a swift smack to his sternum, and Principal Daniels raising her pussy out of reach of his tongue.
Michael froze not knowing what to do or what happened.
“Did I tell you you can touch me?” She asked, again, it sounded more like an order.
“Um, no… sorry…” Michael muttered staring up at Principal Daniels’ wet pussy and curvy, plump ass cheeks hovering above his face.
“Sorry what?” She asked. There was a long pause where Michael found himself struggling for the word Principal Daniels was wanting. In the end she gave him the answer. “Mistress.”
“Sorry, Mistress,” Michael said, still unsure of himself. The tension in the moment continued for several moments as the two held frozen in place until in an instant Principal Daniels loosened and lowered herself down on to him again. Her hand that had struck his chest now rubbed warm circles down his center to his naval
“That’s my good boy,” Principal Daniels said with a smile in her voice. “Move your arms to your side and keep them there. Now lick your Mistress’ pussy, baby… ooooo…”
Michael complied, snapping his hands to the outside of his thighs as he felt both her hands gently navigating his chest and belly. Exploring him like she was an alien and he was a new species. This time when he shoved his tongue into her tight pussy he felt her sit back on his mouth. His nose flirted with the mouth of her butt crack as she rode him, rocking her hips forward and back.
“Oh, yes, darling, just like that. Mmm… do you like that feel?” Principal Daniels asked. “My thighs locked around your face… my-ahh ahhhmm… my pussy sitting on your face?”
Michael’s tongue was buried so far inside the woman’s pussy that he couldn’t talk. He couldn’t make much of a noise other than groan. In return Principal Daniels rewarded her pupil by squatting lower on his face.
It was then Michael felt a hand brush down the side of his leg. Principal Daniels’ now familiar fingers coiled around his shaft and stroked the member begging for attention. Michael felt his pre-cum being spread across the face of his skin with every stroke. Pumping his shaft, Michael flexed back into Principal Daniels’ palm.
“Ohhh… your poor cock… so desperate for attention… you’re probably abusing this thing every night imagining the women you’ll never have…” Principal Daniels groaned, and suddenly stroked his cock hard and thoroughly for several seconds. It made his heart race and his mouth groan into the woman’s sex. His shaft flexed as hard as it could and suddenly Principal Daniels stopped her touch of his shaft.
Michael’s hips wiggled about as his new mistress alternated between moans of pleasure and giggles at his torture. It took a moment to realize but Michael noticed his mistress humping her face with every rock of her hips. Every once in a while on those humps, Michael’s chin would catch on the skin above her pussy and Principal Daniels would gasp or her moan would be a sudden yelp of pleasure.
When he realized this, Michael started lapping his tongue out and over this spot over and over. Principal Daniels’ moans became erratic and uncontrollable.
“Oh, shit… you fucking… your… yes…. right there…” She moaned exasperated cries.
Michael’s tongue was growing tired but he couldn’t stop, not when he just found this spot. His tongue flicked over it faster and despite her clearly having dominance over him, in that moment, as she heaved and trembled with every wet lick he did on his principal’s pussy, he felt in control of her.
“Shhh sh shit… yes… don’t stop… don’t stop fucking…” Principal Daniels moaned as she rode his face.
It was then that Michael realized he had found his Mistress’ g-spot. Licking it in rapid succession over and over again he felt Principal Daniels’ legs quiver and her pussy pulse.
“Oh gahhhh!” Her screams crescendod and for a brief moment Michael felt Principal Daniels sit completely on his face smothering him. Dragging his tongue back and forth repeatedly drove her even more wild and the whole moment was strangely erotic.
The moment her orgasm had passed it was as if she realized she had an 18 year old student locked beneath her and Principal Daniels sprang from her position. Feeling his face doused in moisture, he sucked in air immediately. Principal Daniels turned around on him with a light sweat on her brow and a giggling smile on her lips.
“Good boy… good boy…” she said, taking his cheek in her palm and going to work cleaning him up. She planted long deep kisses on his lower and upper lip, while shoving her tongue inside his mouth to suck on.
The hot and wet moment continued for several seconds as Principal Daniels moved his face about as she kissed, licked, and even bit various parts of his lip, tongue, and cheeks like a cat cleaning her toy. When she stood and ordered Michael to his feet, he felt a dizzying spin as he stood before in the principal’s office before the principal’s desk just as he had when he entered but yet everything seemed so different. So confusing, and yet, simpler.
With a delicate finger tapping the edge of her desk that just moments before she had been leaning upon. “Put you hands here,” Principal Daniels said.
Michael complied. He had to lean over to put both of his hands flat on the desk.
“Spread your legs and don’t move your hands. Do you understand?” She asked.
“Yes…uh, yes, mistress,” Michael said and did. He felt like a criminal about to be searched by a police officer with his body half hunched over her desk, his hard tortured cock still dangling between his legs.
Principal Daniels ran her fingers over his back and around his waist as she circled him. “You’re a good boy, Michael. You listen well. You do as you’re told. Have a good heart, I think. That’s why I don’t understand why you got wrapped up in such a dirty business of spying on your teachers? Sexting with them?” Ducking beneath his right arm, she knelt in front of him, her neat hair brushed off to one side and a seductive look in her eyes. “Life’s full of consequences. Rewards and punishments. It’s time you learn that.”
Principal Daniels held his gaze as she leaned forward and took the head of his cock in her mouth. The large, swollen head looked massive in her tiny mouth and delicate fingers. She hummed a note of approval as she tongued the urethra before forcing the shaft deep down her throat. A look of concentration came over her brow as she grabbed the base of my cock and she forced the shaft up and down her throat in sudden, wet, sloppy motion. The feeling was amazing and panic inducing simultaneously. The forcefulness and aggression of the movements.
It was like Principal Daniels was choking herself on his cock. But as she gagged she also moaned. As her eyes watered they also held his gaze and begged for more.
She was aroused by this.
Just when the feeling became too much, Michael found himself pinching his eyes shut and putting his mouth to his arm. Principal Daniels suddenly stopped her assault on her throat with his cock. Leaving his dick dangling and engorged between his legs, the middle aged woman stood, swiping the tears from the corners of her eyes and the excess saliva from around her lips with the back of her hand.
Michael panted as the roller coaster of arousal continued as the stress of the moment was beginning to peak for him. Standing behind Michael, Principal Daniels kissed the back of his shoulder. Her right hand slipped around his waist and grasped his heavy shaft and began to gently stroke his shaft. Up and down, up and down her hand went.
“Do you like that?” She asked with a hoarse voice.
“Yes, mistress,” he said.
Her grip grew firm around his cock as did the pace at which she stroked him. From the base to just before the tip of his shaft, she stroked him making him begin to pant.
“Do you like being sucked, and milked? Do you enjoy eating your mistress’ pussy?”
“Yes, mistress.”
Her hand pumped vigorously now. He could feel his ball sack bouncing from front to back with the fast and hard pumps. It was close to hurting but not fast enough for it to be. He found his cock tensing and flexing. He was close.
“Mmmmm that’s it, baby. Fuck that hand. You like that? Yeah?” Principal Daniels purred in pleasure. “You want to cum for your mistress? You want your mistress to milk your fucking cock? This could be your new habit. Your new naughty fucking ritual.”
Principal Daniels stepped around to Michael’s side still stroking his cock. With her left hand she had undone her blouse exposing her breasts from the neck. She groped them as she bit her lip and stared into Michael’s narrowing eyes.
“These tits, this hand, this fucking pussy… it could all be yours. You could have it all to yourself every week. Every day, if you like.” Principal Daniels panted herself as she pumped faster on his cock. “You just can’t sext Mrs. Cherry again, you understand? You see her during class and that’s it okay?”
“Yes… mistress…” he groaned.
“Good boy… mmmmm…. Now cum for your mistress. Come on, fucking cum for your mistress,” Principal Daniels demanded.
Michael’s eyes rolled back and his knees gave way for a moment as he felt the first spurt of semen spurt from his cock onto the side of the principal’s desk.
“Ohhh, yes, good boy, mmmm yes…” Principal Daniels moaned. “Empty those big fucking balls for your mistress.”
Principal Daniels continued to pump his shaft long after Michael went soft in her hand. When she finally did stop stroking him, Michael’s cock felt like an abused piece of rope. She ordered him to dress and she closed up her blouse and fixed her skirt.
“Now Michael, remember what you agreed to,” Principal Daniels said, wagging her finger at him.
“Yes, mistress,” Michael replied, realizing how natural it felt to say.
“Today’s consequence was a reward. You don’t want to experience a punishment.” She warned. “Now. Have a good weekend. I’ll expect to see you after school on Monday in my office, understood?”
“Yes, mistress,” Michael smiled. He went to leave but was stopped.
“Oh, don’t forget this,” Principal Daniels smiled, holding up his cell phone that was on her desk.
Michael took the phone and saw the seductive look in Principal Daniels’ eyes that had a hint of danger in them as well. He left her office feeling as though he had just walked through a hurricane and was trying to decide if he was still in real life. Everything felt so surreal as he walked down the stairs.
Pushing outside to the front parking lot he saw an empty lot except for a few dozen cars belonging to the athletes.
Then his phone buzzed to life. He looked half hoping it was his mistress.
Then he saw the name on the received text… Mrs. Cherry
Mrs. Cherry
‘Just saw you leave Principal Daniels’ office. Come to my car. I’m parked around back between the school buses. NOW.’
Source: reddit.com/r/Erotica/comments/txo4is/inappropriate_principal_part_1_of