Waking up in Schoolgirl Heaven Chapter Sixteen: Teasing the Naughty Headmistress

 

Waking up in Schoolgirl Heaven

Chapter Sixteen: Teasing the Naughty Headmistress

by mypenname3000

© Copyright 2020


Story Codes: Teen male/Female, Teen male/Female/Teen female, Teen female Mastubation, Oral Sex, BDSM, Domination/submission, Bondage, Voyeurism, Exhibitionism, School

For a list of all parts, click here

Comments are very welcome. I would like all criticism, positive and negative, so long as it’s
constructive, and feedback is very appreciated.



Click here for Chapter 15.



Note: Thanks to Alex for beta reading this!

You have the entire night to play with the Devas, but you have this window to get some answers from the headmistress. She’s already proven herself to be pliable. Bending her over the desk and spanking her in her office had been a thing of beauty.

A delight that you want to experience again.

“That was delicious,” you groan as you push up from the table.”

“So, you up for some dessert?” Thi asks. The Vietnamese beauty arches an eyebrow at you.

“I am,” you say. “Some MILF dessert.”

“What?” gasps Kornelia. The German girl’s mane of brown hair tosses as she whips her head over to stare at you. “Not with us, mein Mausebär?”

“I’ll be coming back to the dorm,” you say. “I just have to speak with the headmistress.” You gaze out at the girls of the dorm. “You are all gorgeous, beautiful. Young and tight and sexy, but there’s one thing you can’t be.”

“A MILF,” groans Darcie. The limberest cheerleader sighs. “That’s true. We’re all way too young.”

“And on the pill, cariño,” says Alondra. “So no worrying about making us into MILFs any time soon.”

“I’ll be back,” you tell them. “I want you ten wet and ready and primed for me. We’re going to have an orgy.”

The girls all grin at you and squirm in their chairs. This impossible school truly is heaven. It couldn’t be true heaven, could it? Was that why your memories were so fuzzy? Did this all feel similar because this was like an amplified version of high school?

“Well, have fun with the headmistress,” says Krystal. The tall girl winks a hazel eye at you. “She doesn’t get frisky with the girls too often, but I hear she is mean with a dildo. Watch that ass.”

“Oh, it’s her ass that’s going to need to watch out.”

The ten Devas burst into wicked laughter.

You pull away from them, whistling as you head to the teachers’ tables. They’re breaking apart, their plates being cleared away by some of the freshman girls. One of them, that Black girl that you’d seen grinning at you, squeals in delight.

Then she picks up her skirt and flashes a trimmed, black bush at you. “Wanna be my first. I broke my cherry doing…” Her expression grows puzzled for a second. “I mean… It had to be while doing gymnastics. I’m sure that’s it. But no cock’s been in me. Only in my dreams.”

“Maybe,” you say. “But I got to talk to the headmistress. We can have some fun later.”

She beams at you and skedaddles.

“You need to talk to me?” the headmistress says, moving up to you. She looks amazing in that tight skirt and her thigh-high stockings. “Mmm, what are you up to, bad boy?”

“Let’s go to your cottage and find out,” you say. “I still have some questions, and I need some guidance.”

“Well, that should be the guidance counselor’s job, but I don’t mind giving you such attention.”

“Good,” you say.

“Yep.” Bree pops up beside you. “We need some counseling.”

“We?” you ask.

She winks at you, her dyed-green hair fluttering around her face. You almost tell her no, but your heart beats faster. She’s such a cute girl. Intoxicating. She stands out from the others. If this is heaven, you must have had a big crush on her in your last life.

“Yeah, we need some counseling,” you say. “Let’s go, Headmistress. Now.”

“Yes, bad boy,” the older woman purrs in a surprising amount of submissiveness. You felt that trait in her earlier. She feels your domination and responds.

“Bad boy, huh?” Bree says as you put your hand on the small of your headmistress’s back and guide her towards the door, Bree pacing you. “I wouldn’t guess.”

“He’s such a bad boy,” the headmistress moans. “The things he did to me in my office.”

“Is your ass still sore?” you ask.

“Wonderfully,” she breathes.

“Oh, my, boyo,” Bree says. “I knew you would make school so interesting.”

“Glad you approve.”

By the door, the girl with the half-red and half-black hair spots you. She shudders and licks her lips. The faint memory, almost a tickle, of pissing on her face races through your mind. She watches you pass with that same submissive heat.

“Sup, Terra,” Bree says nonchalantly.

“H-hi,” Terra says, her body trembling.

You don’t know why you do this, but you bark, “Terra, go to the girl’s bathroom and beg every girl to piss in your mouth. Tomorrow, I want to know how many girls took you up on the offer.”

“Yes… Master,” she breathes.

“Damn, boyo,” Bree whispers as Terra scurries off. “Golden showers? I didn’t know she was down for that.”

“Interesting,” the headmistress says. “Terra does have that sort of… proclivity. Any reason you told her to do that?”

You shrug as you step outside. The sun is starting to set, the air growing cooler. Girls are fanning out as they spend some time outdoors. You pass a pair making out, and then a group of freshmen girls playing a variation of Duck, Duck, Goose. The girl declared Goose caught the other girl and started kissing her.

You keep your hand on the small of the headmistress’s back, guiding her to the cottage she had pointed out on the tour. They are all small and well-maintained with open shudders that are painted white to accent the mauve siding. There are flowers planted before hers.

Your cock is throbbing as you get closer and closer. Ideas are throbbing through your mind.

“I hear you’re not one for playing with the students,” you say.

“Some of them remind me…” She swallows. “Well, it seems best to be aloof. I’m the school’s head administrator, not their lover. I can’t play favorites.”

“I got it,” you say, filing that way. What is she hiding? “But I’m different?”

“Well, I haven’t been with a man in a while,” she says, squirming. “Vibrators can only do so much for a woman.”

“Amen,” breathes Bree. She grabs your left arm, holding you tight. “It was wonderful getting to try the real thing, boyo.”

“And why is Bree here?” the headmistress asks. “Are you bonding with her?”

“She’s definitely stirring,” you say. “I don’t know. Just something about her.”

Bree beams.

“Well, you’ll get to see a lot of her. I checked the schedules, and you have Bree in all your classes.”

“I do?” you ask. “What are my classes?”

“PE, Communications, Art, Civics, Advanced Biology, and then English to round the day out,” Bree says. “Mmm, if I’m in all your classes, so is Juliana.” Bree shivers.

“Oh,” you say. “What’s her deal.”

The headmistress stiffens. “She’s… trusted. Head of the inquisition squad. Just took over. She’s very dedicated to making sure that none of the school rules are violated. Like being out after curfew or trying to leave the school grounds.”

“Yeah,” Bree whispers. She swallows and then glances at the wall and the forest beyond wistfully.

In that moment, you realize Bree has tried to get out of the school grounds. What went wrong with her? Why did she want to go?

“Juliana gives me the creeps,” you mutter, not happy to spend all day sharing classes with her.

“Mmm, yes, the last head was a more balanced girl, but, you know, she had to be moved on from the post.”

“Graduated.”

“Demoted.”

“Really?” Bree asks. “She didn’t graduate?”

“It’s complicated. And talking about the Inquisition Squad is rarely advisable. They’re very bright and eager girls who want to make sure that the school is harmonious and that all the students get their education and have fun.” The headmistress smiles at you, her brown eyes sparkling. “So enjoy yourself, bad boy. There are a hundred and sixty girls at this school, and all of them will be more than happy to let you ravish them.”

“Plus, the teachers,” Bree adds. “You’re going to get laid, boyo.”

“I bet,” you say. “This mountain air sure is invigorating. I can’t believe how many times I came during dinner.”

“Yes, your performance has been rather amazing,” the headmistress purrs. “Everyone notices your stamina. You definitely will have the girls lining up.”

“It was almost impossible,” you casually say. “Cumming that many times. Usually, I need twenty minutes to an hour to recover.”

“I guess it’s the mountain air,” the headmistress says lightly. Was that too lightly. Too glibly?

“Mmm, or it’s all us fine, fine cuties that are keeping you hard, boyo,” Bree coos.

“Maybe,” you say, glancing at her. She is sexy.

“What’s going on, Headmistress?” the cold voice of Juliana asks.

“Just having a little threesome with our newest student and Bree,” the headmistress says, giving her a cool look. “Nothing wrong with that?”

“Of course not, Headmistress,” Juliana says. A smile spreads on her lips that doesn’t touch her eyes. “He’s just a wild one. I can tell. He’s going to be trouble.”

“Mmm, the best men are,” the headmistress says. “You’d know that if you were older and ever been with one.”

Juliana’s eyes flick to you. “Well, I’m sure our celebrity will be able to fix that for me, won’t he?”

You wink at her though the idea of sticking your dick in her is like plunging into a cold lake. You could do it, but you’re not going to be able to perform. Just shrivel up.

“Come on,” you say. “I don’t want to be out after curfew. Got to get back to the Devas before then.”

“Lucky them,” Juliana says. “Good night, Headmistress. I’ll see you all tomorrow.”

“She really has the same schedule as us?” you ask after Juliana’s out of earshot.

“Afraid so,” Bree answers.

“Fuck,” you mutter.

“Yeah, it’s not ideal.” Bree shrugs. “Now, shall we?”

You grin and give the headmistress that last push. She rushes up the two stairs of her cottage’s porch. She grabs the door handle and opens it. Not locked. Why lock doors here? She opens it up and ushers you inside.

It’s furnished in an almost familiar way. Not like your home but in the same sort of vein. Dollies on the back of the couch and the coffee table. Vases with fresh-cut flowers. Bowls of potpourri. There are little statues of angels on all the shelves. The cabinet doors to an entertainment system are probably hiding her TV.

Is there cable here?

But there’s something off. Something missing. What?

“Strip, Headmistress,” you command, here for other things. “Down to those thigh-high stockings. Show Bree what I did to your ass.”

“Did you fuck her?” Bree asks.

You wink at her.

The headmistress pushes up her glasses before she unbuttons her low-cut blouse with its ruffled collar. She works with care, sliding each button through an eyelet. It’s a delicious sight to watch. You grin as she exposes more and more of those large and lush breasts and that lacy bra she’s wearing beneath.

She opens her blouse, Bree watching on. Then the Irish girl does the same. She starts unbuttoning her blouse, working her fingers fast. As the headmistress reaches behind her to unhook her bra, Bree opens her blouse and her round and perky tits spill out.

The headmistress glances at them then jerks her gaze away, color spotting her cheeks.

Your brow furrows.

“Mmm, don’t you like my tits, Headmistress?” Bree asks, squeezing them and kneading them.

“They’re fine,” the headmistress says and undoes her bra. She pulls her bra off her shoulders and exposes her large tits. They are big and heavy, swaying with her movement as she drops the bra to the floor.

“Bree’s tits are fine?” you growl and seize one of her fat nipples. You pinch her nub.

She gasps and shoots her gaze up to your eyes. You smile as you twist her nub. You savor the way she shudders. It’s such a fantastic delight to see her eyes twinkling. There’s a sparkle in them that’s so arresting.

“Mmm, I think they’re more than fine,” you say. “Look at them and tell Bree what you really think.”

The headmistress whimpers as you twist her nipple hard. She quivers and then shoots her gaze to her left. She stares at the ripe and firm perfection of Bree’s seventeen-year-old tits. Bree grins and jiggles her tits. They bounce up and down for a moment, the ripples so enticing to see.

“Wow,” you groan, staring at them. Your mouth salivates at the sight of them. “Don’t tell me those are not perfect breasts.”

“Your big boobies are amazing, Headmistress,” Bree moans. “Aren’t mine?”

“Th-they are,” stammers the teacher. “Beautiful. Just so perfect.”

“Mmm, now that wasn’t so hard, was it?” you ask, twerking her fat nub.

“No, bad boy.”

You smile. That title Terra called you… That makes you throb and ache. You can’t wait for the headmistress to call you that. But not yet. “Skirt off, Headmistress. Bree needs to see what I did to your ass.”

“Mmm, I do,” Bree moans, still massaging her teenage titties.

You love both of them. The MILF softness of the headmistress’s and the youthful firmness of Bree’s. You cup both their tits, massaging them, savoring the difference. Both of them groan as you do, their hands unzipping their skirts.

Bree’s falls off in a flare of tartan delight, exposing that pussy you’ve already fucked today. Bare mons gleaming with pussy juices and not a spec of your cum to be seen. Alesha has been thorough. The headmistress’s skirt slides down thigh-high-clad legs and ends up around her feet. Her thick, brown bush drips with her cream.

She turns around, slipping her tit regretfully from your grasp, and bends over without being told. Her ass still has a cherry blush from your hand. Bree gasps. She shoots you a glance, arching a thin, black eyebrow.

“Boyo, you didn’t.”

“He did,” breathes the headmistress.

“Damn,” says Bree. Then she gives the headmistress’s rump a playful smack.

“Mmm, you can do better than that,” you tell her. “Really draw back and let loose.”

She grins at you and does just that. Her hand rises up and then hurtles down.

SMACK!

A brighter red spot blossoms on the headmistress’s rump. Bree bursts into giggles and bounces on the balls of her feet, her teenage titties jiggling. The headmistress moans, her back arching. You love it. This is going to be a fun night of getting questions answered.

But can you trust Bree with them?

Yes. Yes, you can. You can feel it in your guts. She’s a girl that will be with you through thick and thin. You wish you understood this connection. It has your dick throbbing and aching to just bend her over and plow into her.

“Headmistress,” you say, “strip me.”

“Okay,” she groans.

“Mmm, you need to address me as something more respectful.” Master felt too strong to use. It wasn’t time, but… “Call me, Sir.”

She glances at you, her eyes shocked. You give her a level look back. You need to be strong with this one. Bree’s watching. It won’t be good to show any weakness. Headmistress Warren feels like the sort of woman who’s used to bending to the will of those stronger than her.

Be stronger.

She wilts under your gaze. “Yes, Sir, I’ll strip you.”

A smile spreads on your lips.

Bree goggles at you. Then she grins and nods in approval.

The headmistress begins undoing the tie. It whisks through your collar. She drops it to the floor, her eyes looking so stunned behind her glasses. And so liquid. Her hair pinned up in a bun makes her so motherly and matronly.

While that naked, busty body wearing only those thigh-highs makes her appear as such a delicious whore. A woman you’re going to enjoy ravishing.

Your dick throbs and aches and your heart pounds as she works the button of your shirt. She exposes your muscular chest, her breath washing over your hairs. Then she is peeling off the shirt and letting it fall. Her hands reach for your pants.

“On your knees,” you command. “When you take off my pants, you kneel, Headmistress.”

“Yes, Sir,” she says, more passion in her voice. She shudders and sinks to her knees. “This is the best way, Sir.”

“Mmm, it is,” Bree moans, her hands kneading her tits as she watches. That awe is still in the gleam in her eyes.

You love it.

The headmistress undoes your belt and then opens your slacks. She pulls them down your legs, your cock popping out hard before her face. She gasps at the sight of you, her eyes crossing behind her glasses. She groans at the sight of you, her lips smacking together.

She takes a lick right across the tip of your cock. You shudder at the sensation. Your balls tighten as she gathers up the precum beading on your slit. She holds it on her tongue before she pulls it back into her mouth.

“Did I say you could do that, Headmistress?”

“No, Sir,” she breathes.

“You’re lucky it felt amazing. I can’t punish you for that, can I?” you ask.

“No, Sir,” she moans and then licks your cock again, an impish gleam in her mature eyes.

“Why you saucy bitch,” you say. “Mmm, I think I’m going to have to punish you.”

“Oh, yes, yes, let’s punish her, boyo,” Bree says, bouncing up and down. “I don’t know why, but that sounds soooooo hot.”

“Aren’t you a kinky one?” you say.

She winks at you.

“Well, if I’m getting punished,” the headmistress says and opens her mouth wide. She sucks your cock past her lips and nurses with hunger.

She peers up at you, those glasses giving her that naughty librarian look. Her cheeks hollow while the suction reaches down to your balls. It’s such a delicious treat to enjoy. You can’t help but smile at how it radiates bliss through your body.

You let her bob her head for a few moments, working those lips up and down your cock. You have ideas. You want to get information out of her, but that doesn’t mean you can’t have fun with her first. There’s something you’ve heard about, things you’ve seen on the internet. It’s all hazy, you can’t even remember the word for it, but you want to try it out.

“Tell me, Headmistress, do you have rope in your home?”

She stops sucking and blinks up at you. Then she slides her mouth off your cock and says, “I might.”

“Fetch it.”

“Yes, Sir.”

She bounds to her feet and looks around like she’s trying to orient herself. Then she darts towards a door. It opens onto a small closet. She digs around in there, her big boobs swaying as she does. Bree comes up behind you and hugs you, pressing her round tits into your back. She must be on her tiptoes because she manages to get her chin just on your shoulder.

“What you up to, boyo?” she asks. “Gonna tie up the headmistress.”

“She’s been bad,” you say. “There are things I want to know from her.”

Bree stiffens. “You best be careful about those things, boyo. Just enjoy the school. It’s amazing.”
“Then why did you try to get over the wall?”

“How do you know that?” she whispers. “That happened years ago.”

“I saw the way you were looking at it and… it just made sense to me.” You really couldn’t explain your hunch.

“And I got in a lot of trouble, boyo. You better be sure of what you’re doing. You don’t want to get on the bad side of the Inquisition Squad.”

Juliana’s cold eyes flash through your mind. You definitely don’t want that happening.

“Here we are!” says the headmistress. “I have some twine.” She pulls out a spool. “I think I used these to make a banner for the Valentine’s Day Dance two years ago. The Lily Blossoms Dance, I believe we called it.”

“Oh, that was a fun one,” Bree says. “I went with Feliciana Saluccia. I was a sophomore and she was a freshman. Boy, did she have a tongue on her.”

“Bet you wanted to go with Ji-Young,” You say.

“We hadn’t reconciled. Boyo, you sure do know a lot for someone who just started today.”

That’s one of the things you want to know.

“Well, will this work?” the headmistress asks as she pads over. It’s a spool of beige twine as thick as a strand of yarn but looks far, far stouter. You nod and take it.

“Bedroom. Lay spread eagle on the bed.”

“Yes, Sir.”

The headmistress’s red rump leads the way down a short hallway to her bedroom. She has a neatly made bed, two nightstands covered in doilies and with reading lamps on them. One has an alarm clock. Her closet doors are closed and she has a dark-stained dresser with an oval mirror on the wall above it. There’s something off.

No pictures. You’ve never been in an adult’s bedroom that didn’t have pictures. All your friends’ parents or mothers had their bedrooms with them. And the rest of the house, too. But not the headmistress.

She lies on the bed spread eagle, her big boobs piling into mounds. You start unwinding the twine. The headmistress tells Bree where she can find a pair of scissors. She returns with them and you snip up the twine into the lengths you need.

You start with her right wrist. She doesn’t fight as you wrap the rough twine twice around her and then knot it. You pull it to the post of her bed and tie it around it, keeping her arm stretched out. She licks her lips, her breasts rising and falling.

“You’re actually letting me do this, huh?” you ask as you grab her leg and start binding her ankle.

“Well, yes, Sir,” she says, her cheeks on fire.

“That desperate for cock, huh?” you ask. “How long has it been.”

“Too long.” She shudders, her toes flexing and curling.

“With a body that fine, you should be having the guys lined up to bang you,” you say as the twine rasps around the post. You pull it tight, her leg stretching out.

She squirms, her brown pubic hairs gleaming with dewdrops. “I work here. You’re the first boy to ever be here.”

“You don’t leave?” you ask. “I know the students don’t, but surely the staff can drive into town on Friday night to pick up a guy.”

“There’s no town that’s close,” she says. “We’re very isolated. None of the staff leaves. It’s a closed campus.”

A shiver runs down your spine. “Not even you? What does your family think of that?”

She looks away. “I don’t have a family.”

Your brow furrows. This hazy memory of looking in her desk drawer and finding a picture of a young girl floods your mind. A girl who looks like the headmistress’s daughter. Why would you have that memory? You never looked in her drawer.

You tie up her left leg, her body quivering. You have so many questions, but it’s hard to focus on them with her almost all bound. You grab her left wrist and pull her fingers up. She has no wedding ring on, but there’s a faint indentation, like she had worn one for so many years that it had left a permanent mark on her body.

Divorced? you ask yourself.

You pull her arm to the headboard. She gasps, her big boobs jiggling. You wrap the twine about her wrist and run it to the post. As you do, you ask, “Why would you agree to work at a place where you can’t leave?”

“It seemed like a good idea at the time,” she says. “I mean, it’s worth it. To help mold all these girls. It’s not like I have anything left. I’m all alone. Never had a family.”

“I see,” you say and finish tying her up. “Mmm, there, you’re all bound. You’re not going away. I can do whatever I want to you.”

“Ooh, and what are we gonna do to her, boyo?” Bree asks. She jumps on the bed, landing on her knees.

“Well, we’re going to tease her,” you say, grabbing her nipple and twisting it. “Play with her. Drive her so wild, she’ll beg to do anything to cum.”

“Fun,” purrs Bree. “I like the idea. Mmm, let’s do this.” She ducks her head down and suckles on the MILF’s nipple.

The headmistress gasps. You lean down and nip her other nipple. She groans at the feel of your teeth biting, lightly, into her nub. The twine creaks as she shudders. She arches her back. Bree’s dragging her tongue in slow circles around the headmistress’s fat nipple, massaging the areola.

Then the girl gasps, “Be right back,” and darts from the room. “This will be perfect!”

You smile at her enthusiasm. You slide your hand down the headmistress’s stomach. You stroke your fingers in a slow circle around her navel. She groans and bites her lower lip at your teasing touch. You smile at her, so eager to make her explode.

Then your fingers shove further down. You slide through the dark curls of her bush. You brush into her silky hairs and find the lips of her pussy. You trace up and down her folds, her juices soaking your digits. She whimpers.

You bring your wet fingers to her lips and smear her pussy cream on them. She opens wide and suckles on them, making your dick ache and throb. You’re enjoying this a lot, hearing something clattering in the other part of the house. You can’t wait to see what Bree has in plan.

Her footsteps rush down the hallway then Bree darts in holding a red, plastic bowl, something rattling in it. “This will tease her!” she says and pulls out an ice cube. “Trust me, boyo!”

“Nice,” you say.

“Oh, my,” the headmistress says, her body twitching, making her big boobs jiggle.

You want her driven wild. You ache to have the woman on the verge of cumming but never quite there. She has answers you need to learn, namely why you feel like you’ve been here and why she took a job that made her prisoner while lying about her family.

This place itches at you. It’s just too perfect. Your mind doesn’t want to accept that this was truly happening to you. Even though you had a great dinner with the Devas and now you have the headmistress of the school bound and at your mercy, you just feel like it could all be taken away unless you understand what is going on.

You snag an ice cube from the bowl, your fingers going numb. Water drips from it, splashing on her belly. You bring it to her fat, left nipple and press it right against the tip for a moment, enough for a bead of water to trickle down her nub.

She gasps, her boobs jiggling. Her toes curl and the twine groans. You smile, loving the reaction she gives. Bree winks at you and takes her own cube. She begins rubbing it over the headmistress’s right boob. Water gleams in the wake as Bree works the cube around that quivering tit.

“Oh, my,” gasps the headmistress. “This is… This is quite teasing.”

“I bet it is,” you say, rubbing your cube around her areola, just grazing her nipple. Water runs over her breast from the melting ice. Your fingers are starting to numb, but it’s worth it to watch her squirm.

“Boyo, look at her,” says Bree. She presses the ice cube right on the headmistress’s nipple.

“Oh, god!” moans the older woman.

“Mmm, you like that?” you ask, pushing yours against her other tit.

She quivers, her boobs jiggling. Her face scrunches up as you two toy with her nipples. Her legs flex, the twine rasping around the post of the bed. More water spills over her tits, a puddle forming in the valley between her breasts.

She whimpers, her scent of spicy pussy grows. You glance at her dark-brown bush. Her dew gleams on the curls. She’s getting soaked from your naughty teasing. That makes you smile while your ice cube dwindles.

You toss the half-melted one in the bowl and get a fresh one. It’s cool in your grasp. “Mmm, I bet there are other sensitive spots on your body.”

“Oh, boyo, there are,” says Bree, her cube melting fast. She pops hers in her mouth and crunches down on the ice.

You place your new cube right on the headmistress’s bellybutton. She squeals as you press the corner into the divot. Her thighs really flex as you do that, pulling on the twine. She moans, her face scrunching up.

“Sir, Sir!” she moans.

“Mmm,” Bree coos and then darts her head down and sucks the headmistress’s wet nipple into her mouth. She nurses on it as you grin.

Smiling, you slid the ice cube from her bellybutton, a little pool of water left behind. You leave gleaming beads behind as you slide the cube towards her pubic hair. You press the ice into her silky curls, matting them down as you reach lower and lower.

“Sir!” she gasps. “That’s… That’s…”

“I know,” you say, rubbing up and down her folds. You find the entrance to her cunt and shove that cube of ice into her.

She gasps as her cunt swallows it up. You push it deeper. Goosebumps break out across her legs. She quivers, her wet boobs jiggling. Bree keeps sucking as you pull your fingers out, coated in warm juices.

You suck on them as the teacher endures the ice in her pussy. She’ll have that cube melting in her the entire time. Her moans echo through the room. Her face contorts. You smile and grab another ice cube from the bowl.

“What to do with this one?” you ask her. “Also put it in your pussy?”

“Oh, please, no, Sir,” she moans. “It’s cool enough.”

“Is it?” you ask and shove this one into her bush. You rub up and down her slit. “Are you positive?”

“Sir!” she gasps, her body bucking. Her big boobs jiggle as you work the cube up and down, her silky curls brushing your fingers. “That’s… Oh, god, that’s so intense.”

“I bet,” you say, watching the way her mouth opens and closes. That makes your dick throb and ache.

You have to do something with that. You pull the ice cube from her pussy lips and then lick at the cold block. Her pussy juices adorn it, a spicy flavor that’s been diluted by the welting water. You shudder, your dick throbbing.

You grin and move on the bed until you’re kneeling while straddling her left arm. Your cock thrusts right to her mouth. “You like sucking on it,” you say, hearing something clattering in the other part of the house. “Open wide.”

“Yes, Sir,” she moans as you grab her nipple and twist it.

She moans and opens her mouth. She slides her lips over the crown of your dick and suckles. You groan at that, your finger twerking her hard nub. She shudders, her limbs spasming against the ropes. It’s incredible.

With her mouth happy sucking on your dick, you press the ice cube to her tit. You rub it up and down on her nub. She groans, her face twisting in delight. She shudders, her mouth nursing with such passion on your dick as you do.

Bree pops her mouth off the other nipple and grins. “Mmm, how’s the sucking?”

“Wonderful,” you say.

Bree slides down the bed, snagging another ice cube. She kneels between the headmistress’s thighs. “I’ll make it even better.

She presses the ice cube into the headmistress’s cunt. The MILF sucks with passion on your dick. She nurses on you. It’s incredible. You groan, loving every second of it. This is a passion that makes your cock throb and ache.

“Fuck,” you mutter. “That’s it.”

Bree winks at you as she works the ice cube up and down the headmistress’s pussy. The woman is sucking on you with such passion. She’s nursing on you with all this hunger that’s a pleasure to enjoy. You shudder. Groan.

The headmistress’s tongue flicks around your crown. She shudders, her wet boobs jiggling. Goosebumps dot her flesh. She whimpers as she suckles on your cock, the ache in your balls growing and growing.

“Damn,” you say. “You are just hungry for that cum, aren’t you? Will that warm-up that cunt?”

“Maybe, boyo,” Bree says. “She’s hungry for it. I can hear the passion. Especially when I do this!”

She rubbed her ice cube into the MILF’s pussy, pressing near the top. It must be the headmistress’s clit because the MILF squeals around your cock. She bucks, her limbs pulling at the twine. Her moans hum around your cock.

“Yeah, that’s wonderful,” you groan, the pressure in your balls swelling.

“Good,” says Bree, pulling the ice cube away.

The moans stop humming from the headmistress, but she keeps suckling. Her eye squeeze shut as she nurses. You grin and press the ice cube melting in your hands on her nipple. She groans. Your dick throbs in her mouth.

Your precum is leaking out. you’re going to give her a big mouthful of cum. She’s going to love it. Just gulp down all the spunk that you have brewing in your balls. It’s going to be an incredible delight. You smile in anticipation.

“Damn, just like that,” you say. “Just keep sucking like that. I’m going to warm you up with my cum in your mouth, and if that’s not enough, well…”

“Your pussy!” Bree squeals and dives her head down.

She presses into the headmistress’s brown bush. The MILF shudders, clearly getting her twat eaten out. It’s a lovely sight to witness and sensation to feel. You revel in that wonderful tongue bathing over the crown of your dick. Your balls tighten more and more.

Bree’s head moves, feasting on the headmistress’s pussy. You rub your melting ice cube over the headmistress’s nipple, water running over her breast. She whimpers, sucking with such an intensity on your dick.

“Stop licking her, Bree,” you growl. “She’s not allowed to cum.”

“Right, boyo,” says Bree.

She rips her head up, pussy cream dripping down her chin. It looks more watery than usual. The cube in her cunt must be melting fast now, making her brimming with diluted cream. The naughty Irish girl holds up her cube. It’s half its original size.

She winks a green eye and then shoves that into the headmistress’s pussy.

The woman bucks again, squealing around your sensitive crown. Her mouth sucks with such hunger on your dick. She nurses with passion. Her cheeks hollow. She groans with such wicked delight. You shudder, the ache building at the tip of your cock.

“Fuck,” you growl.

Cum.

You fire your jizz into her mouth. Spurt after spurt of your cum fires out of your cock and bathes her throat. She squeals, her body bucking as you flood her mouth with all that jizz. Her cheeks hollow. Then she gulps it down with hunger. She swallows all that cream with such delight, her eyes squeezing shut.

“Fuck!” you groan. “That warming you up, slut? I bet it is. Goddamn, I bet it’s warming up that cold cunt right now.”

She squeals around your cock, her body twisting and bucking. She whimpers and moans as she gulps down your cum. She swallows every drop you have, draining your balls. You suck in a deep breath, savoring this moment.

This rush.

You hit the peak and pant. You slide your cock out of her mouth and smile down at her. “Now, Headmistress, does your pussy need my dick to warm you up? My hot cum to heat up that naughty snatch shivering around the ice cubes?”

She nods. “I do, Sir.”

“Sir?” you ask. “No, no, Master. If you want me to warm up that cunt, I need something more from you. I need to own you.”

“Oh, my god, boyo, do you know how wet I am right now?”

You glance at Bree and wink at her.

“So, Headmistress? Do we shove more ice cubes in your cunt or do I slide my big, throbbing cock in you.”

“Lord, you are such a bad boy,” groans the MILF. Her big breasts jiggle, still gleaming wet. “Yes, yes, Master, fuck me. Warm me up.”

“But only so long as you don’t cum.” You grin at her, a plan forming in your mind. “I don’t want you to explode. I want to cum in you, dump you with my cum, and then pull out of you all while you fight off your orgasm. If you do that, then I’ll know you truly mean it when you call me Master.”

“And if I do cum?”

“I finish up in Bree, we untie you, and you never get to enjoy my cock again. I’ll fuck every schoolgirl tart and hot-ass teacher in front of you.” You grin at her. “You don’t want that.”

“I don’t, Master,” she moans. “I’ll do it. I can endure your cock. I promise.”

You wink at her. “Of course you can.”

“Shite, boyo,” Bree groans. “You’re amazing.”

“I know.” You glance at her. “Sadly, you’re going to have to watch, but I’ll make it up to you.” A grin spreads on your lips. “Feel free to masturbate, though.”

“Vibrator in the nightstand drawer,” groans the headmistress. “Has fresh batteries in it.”

“Why, thank you, Headmistress,” Bree says and opens the drawer. Her eyes light up as she pulls out a pink shaft with a purple base. “Nice.”

As the toy hums to life and Bree moans her delight, you move between the headmistress’s thighs. Your cock is so hard. So ready for this delight. You know if she holds off cumming, you’ll have her so horny, she’ll have to answer your questions.

You’ll break her with pleasure and find out some answers while having a great orgasm in the process. You know this will be grand. A mighty burst of ecstasy that will explode through your body and leave you grunting and groaning.

You guide your cock to her pussy, watery cream running out of her cunt’s depths and washing down to her asshole. A large wet spot is forming on her comforter. You press your cock into her bush, her silky curls rubbing against you.

Then you thrust into her.

She’s cool. Her pussy’s not as warm as others you’ve enjoyed. She gasps, her cunt clenching down on your dick. Her body shudders and her face contorts. Her head tosses and her wet tits heave. You love it, pushing deeper and deeper into her. You feel something cold on your tip.

The last of the ice cube.

“Oh, my god,” she moans. “I have to cum!”

“Don’t!” you growl.

“No, no, you’re not allowed!” pants Bree. The vibrator’s hum muffles. Out of the corner of your eye, you see her leaning against the dresser and sliding the buzzing shaft into her twat. “But I am.”

“Yes, you are,” you pant, not wanting Bree to be a sex slave. You want more from her.

You draw back your cock, the headmistress squeezing her twat around your dick. Her face contorts with passion. She gasps and moans as you slam back into her. The pleasure ripples around your cock. You shudder, savoring the feel of her cunt.

After just a few strokes, her pussy is heating up. The friction is warming her cunt and your dick. The pleasure flows down your shaft as you enjoy burying into her again and again. You savor every hard plunge and powerful stroke into her snatch. She feels incredible. This is the delight that you need to enjoy.

A pleasure that you need to treasure.

You groan, pumping away at her. You fuck her hard and fast. You plunge into her snatch again and again. Her pussy squeezes about your cock. The massaging friction is wonderful. You groan at it, shuddering at how amazing this feels.

“Oh, my god,” she moans. Her mature face twists. She groans through clenched teeth.

“That’s right,” You growl. “I own your pussy, Headmistress. You cum when I let you.”

“Yes, Master!” she howls, her back arching and tits bouncing.

You grin and thrust hard into her. You fuck her without mercy, your balls smacking into her taint. Her juicy pussy squeezes about your cock. It’s the wettest cunt you’ve ever fucked. You love the way her snatch clenches you as she fights her orgasm.

It swells that ache at the tip of your cock. Your climax builds as much from the friction as the look of passion on her face. Her head tosses back and forth. Her moans and whimpers echo through her bedroom.

Bree’s join them. The vibrator’s buzzing hum swells and dims as the naughty schoolgirl works it in and out of her cunt. She fucks herself with it, moaning, groaning, and gasping. Her passion echoes through the air.

“That’s so good,” she whimpers.

“I know,” you growl, fucking the headmistress’s cunt. You’re so close to cumming while she fights against her own orgasm.

The headmistress’s body trembles, her boobs jiggling as that amazing cunt massages you. You bury hard into her, balls smacking into her. You don’t hold back. No waiting for her to cum first. This is all about your pleasure.

And her submissive frustration.

You slam to the hilt in her. “Fuck!”

Your cum erupts in her.

“Master!” she moans, her pussy clenching down on you. Her face contorts. “Please, please, please, can I cum?”

“No!” you roar, pleasure slamming into your mind.

Every spurt of your cum into her pussy slams delight into your mind. Her hot quim clenches and relaxes on you, almost like she’s cumming, but it lacks that intensity. Still, it feels delicious as you baste her cunt with your seed.

Stars burst across your eyes. You shake your head, breathing heavily. Your hands grab her tits. You squeeze them hard as you shudder through your pleasure. Ecstasy wreathes your mind as you fire the last blast of your cum into her twat.

“Damn, you have an amazing pussy,” you tell her. “Fucking perfection.”

“Thank you, Master,” she whimpers. “I need to cum. Please, please, let me cum.”

You open your mouth when Bree gasps. “Shite, yes!”

Her round tits heave as she bucks, the vibrator buried deep in her cunt. She shudders against the dresser, the knickknacks on it rattling. Her moans sing through the room. Her face contorts with passion.

“Oh, god!” she groans, pussy cream spilling down her thighs. “Oh, that’s good.”

“Please, Master,” begs the headmistress.

You turn your attention to her. “No, I have a few questions.”

She blinks at you, her eyes glossy with her passion. Which to ask her? Do you find out about why she’s lying about having a family? Or do you ask her why you feel like you’ve been to this school before?

What do you choose?

What question do you ask the Headmistress first?

  • Do you find out about why she's lying about having a family? (56%, 74 Votes)
  • Do you ask her why you feel like you've been to this school before? (44%, 57 Votes)

Total Voters: 131

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To be continued…

Click here for Chapter 17.

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2 thoughts on “Waking up in Schoolgirl Heaven Chapter Sixteen: Teasing the Naughty Headmistress

    1. mypenname3000 Post author

      It’s what happens when you set the experation on the same day as you open the poll. It’s fixed now.

      Reply

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