It was a bright and cloudless morning and the sun was beaming its light upon your face. You reveled in the calm as you began your two weeks vacation. Initially reluctant, you accepted it as your mind and body needed some relaxation. Since it was mid morning, it was the perfect time for a walk. It was a good way to start your morning, but hunger began to make itself known well into your exercise. Preferring something light and something with caffeine, you walked into a nearby coffee shop. It was atmospheric and somewhat pricey, but your income didn’t make you worry.

“One medium iced green tea and an egg & cheese bagel, please.”

“Okay, that’ll be $7.34.”

As you grabbed your breakfast and took your seat, scanning through the newspaper in front of you. You didn’t find any story that caught your interest except for one about the new community center being opened next week. As you flipped through the pages, your ears caught the sound of someone taking a seat.

“Was it two years or four? I wonder how long it’s been, Mr. Crunch.”

Lowering the paper, you were greeted by a familiar face. Sitting in front of you was Principal Cinch. You were a bit surprised to see her since high school, in a coffee shop of all places. You remembered her dragging you into her office and doing the horizontal hokey-pokey, all of that due to you banging Cadence. Still, you were amazed by how word spreads like fire.

“Woah,” You said. “I never expected to see you here. How are things going for you, Cinch?” As you examined her more, you could tell that she looked like she barely aged a day. Aside from that, you noticed that she didn’t have her glasses, which struck you as odd. “Did something happen to your glasses?”

“Oh, I actually had laser eye surgery last year.” She responds. “It feels so liberating to finally see without having to worry about them.”

It was odd at first to see her eyes not behind any kind of lens. However, those beautiful fuschia eyes look absolutely captivating to look at. She still has the look of a woman gifted with experience.

“I can tell. So what brings you out here?”

“Well, Cadence and her husband are helping me do some renovations to my house today. I actually was on my to the home improvement store.”

“Alright. Would you like some help with that? I'm on some ‘state-mandated’ time off.”

“Well, only if you want to.” She said with a smirk.

“Eh, I'm just looking for something to do.”

After a few more moments of chatting and shooting the breeze, you went with Cinch to House Like New, a home improvement store that opened several months ago. She mentioned to you that she was redoing her back patio and that it would require a bit of extensive work. You walked down the aisles with her, grabbing lumber of varying sizes and purposes while grabbing paint and other stuff.

All the while you were helping with her errand, you could've sworn she was giving some sway to her hips, making her nice badonkadonk jiggle slightly. Looking at such a strangely hypnotic sight, words from years ago echoed through your mind:

“Well now, run along. And remember, we might run into each other again.”

It took you a few to process the situation and its inevitable conclusion. Still, you couldn’t believe that she’s presumably keeping her word after all that time. There in the aisle, it all came back to you how she caught you by surprise and copped a feel of your junk, all because you screwed Dean Cadence. Knowing her, she probably would try to do the same thing again. For now, you decided to play her game but on your own terms.

After you helped her gather all the materials she needed, you took a ride with Cinch to her house, making standard small talk along the way. She asked you how life was going for you and all that stuff. She seemed amused by your answers, noting how hard she worked to get to where she is. But there, you noticed a subtle seductive twang in her voice. It was as if she was metaphorically shaking her ass at you. As much as you want to mount her the second you enter house, you knew that she would be expecting something like that. You had your own plans and won’t be giving her any hints.

After about ten minutes of driving, the two of you arrived at her house which was rather big for an average fix around town. It had a rustic yet modern theme to it. You had to admit she has good taste. As soon as the vehicle parked, the front doors opened from which another familiar sight came out. You recognized as one of the girls you were friends with at CPA: Sunny Flare. Your head buzzed with a swarm of questions and a desire for answers.

“Ms. Cinch,” you asked. “What on earth is Sunny Flare doing here?” With your question came a small chuckle from your former principal, making you cock a brow.

“Well Mr. Crunch, she happens to be my daughter.” You were taken slightly aback by the revelation. In all the years you hung out with Sunny Flare, rarely did you ever suspect her of being the principal's daughter. There were a couple reasons you thought of as to why they've never acknowledged their relationship at school, but the reasonable conclusion is the avoidance of perceived favoritism.

“Calculus,” Sunny said, noticing you. “What are you doing here?”

“Well, it's a bit of a long story,” you replied. She took a bit to examine your confused expression with an amused smirk.

“Hmph, I bet you're surprised that Cinch is my mom.”

“Well, I sorta suspected it since, well, you do look a bit like her.”

“Well, like mother, like daughter as the saying goes,” She remarked as she motioned to her car. “Anyways, I hate to cut this conversation short but I have to get going. Ignacio is taking me out on a special date. See ya later, Calculus!”

As she sped off, you looked back on the times you, her, and Ignacio hung out after Crystal Prep. Though as awkward it was to see the two getting all lovey-dovey in front of you, you had to respect the amount of affection they shared. In fact, last week while you and Ignacio were having some bro time, he flat out told you he was going to propose to Sunny one day. Today might be that day.

“Every now and then, I have to take a moment to process how my dear Sunny growing up so fast.” Cinch started offloading her SUV. “Can you please handle the lumber for me?”

You nodded and hauled the lumber to the back patio. From your perspective, it looked rather nice with a few areas need for improvement. The amount of supplies you helped her procure told you that she wanted a complete redesign. After setting the lumber down, you walk into the living room where Cinch was waiting for you.

“I do appreciate the help, Mr. Crunch.” Cinch smiles. “I guess this would be the part where you leave, no?”

“No, I was actually looking for stuff to keep my mind busy.” You remarked. “I was originally going to watch bad movies at home until you surprised me.”

“Why thank you, Mr. Crunch.” She said, walking towards a hall. “Since Cadence won’t be here until around 1-ish, I’m going to go take a shower. Feel free to make yourself at home and grab something to drink if you want.”

As she walked away, you kicked back on the couch, cozy as the room it resides in. As soon as you heard the shower turn on, the heralds of lust returned bearing the most lecherous of thoughts.

You visualized your former principal standing naked in the shower, scrubbing herself down as her hands move all around her body. The very thought of seeing soap flowing from her perky yet sizable chest then down to her hips and flower and her long flowing hair dripping down onto and between her buns was enough to make you fully erect.

Wanting to satisfy that itch, you reached down into your jeans and began stroking your cock. The visualization of her bathing was further enhanced by the sound of her singing voice, smooth and sensual as velvet and seductive as the sirens of myth.

Then, a thought dawned on you as the word ‘seductive’ crossed your mind. You, in a vulnerable position on her couch while jacking off, would be an easy target for her if she snuck up on you. Knowing how she did it the first time around, you felt that it was time for some payback and you were gonna give it to her good.

You stripped naked and quietly approached the bathroom with your erection standing still and proud. Peeking through the keyhole and the semi-transparent shower curtain, you saw Cinch bathing herself. She had on hand on a soapy scrubber and another focused entirely on her crotch. It didn’t even take you two synapses to figure that she was pleasuring her cunt. Another thing you noticed was her hair was long and wet, nearly touching her sweet ass. All that before you made you subconsciously stroke away at your pecker. To see such MILF material before you was almost maddening to the eyes.

Having enough of just the visual, You did your best to sneak into the room. You worried that she might’ve noticed you approaching but you saw nothing to that claim. Seeing an opening in the curtains, you slipped into the shower to see pure mature beauty before you. Her hair, her figure, it was intoxicating. Being slow and silent, you wrapped your arms around her midsection and took hold of her hand with the scrubber. Cinch shook with surprise at first but eventually welcomed it.

“Hmmm, so you finally got the message.” She said as you began groping her tits and beaver to which she moaned. “I wonder when you first got the hint.”

“Well, I would have to say back at the store where you clearly shook that ass of yours.” Mentioning said part of her anatomy, you took that as cue to wedge the length of your cock between her asscheeks. You were still amazed at how good her ass felt. As Cinch moaned, you began grinding your erect cock against her ass, holding her tightly as you began kissing up her neck before meeting her lips with yours. She turned around to embrace you, squishing her D-cup breasts against your chest.

“My word,” Cinch gasped. “You have some nice pecs. It looks like you’ve never lost your build since you were my student.” As she resumed the kiss, you felt her embrace getting tighter. If it were any situation, you would have welcomed it. However, you knew what she intends and you were going to get some payback.

Without warning, you turned Cinch around with one swift movement and resumed your original position. The look on her face at the surprise turn of events was one of shock and arousal. You connected your lips with hers, dominating her tongue with yours with passion and determination. You didn’t let up, not one single bit, even as you began groping her tits and pussy. Though you couldn’t hear it, you could feel her moan.

The second you slid two fingers into her wet vagina, her head jerked back, breaking the kiss with some gasps for air. Now you could hear her lustful moans and they were as sensual as you last remembered them. Soon though, you found yourself grunting as your balls began to tighten as they prepare to unleash the timeless tide of cum.

You strengthen your embrace as your cock throbbed and pulsed as it opened the floodgates for your seed to shoot freely. Even as you came, you couldn’t stop grinding against the luscious ass of your ex-principal as both her ass and your crotch were covered in your thick white cum. Even your hand got drenched with her juices as her climax exploded. The volume and magnitude of her orgasm suggested that she was holding back since you last saw her. Letting your orgasms die down, you lessened you grip on Cinch, content that she’s exhausted, right where you want her.

“Jesus… fucking… christ!” Cinch panted. “How the living hell did you find the energy for that?” You found amusement in her using such vulgar language. To you, Cinch comes off as one of those people that never usually swear. However, from her lack of resistance, underneath all that commanding and intimidating aura is a woman with a rather unusual submissive streak.

“Well,” you said, aligning your cock with her glistening vulva. “Since you caught me off guard all those years ago, I think I should repay the favor.” You slammed your cock so deep inside her that it hit her cervical entrance. The sensation of the sudden impact caused Cinch to shudder and moan as her legs felt weak from such sudden pleasure. She was in the spider’s web… and you were the spider. “Interesting. Didn’t know some prim and proper woman like yourself could be a glutton for submission.”

“T-Touché, Mr. C-C-Crunch.” You brought your mouth close to her ear, your nose bellowing air that sent shivers down her neck.

“It’s Dr. MILFlove now.” You whispered as you began the assault upon her pussy, pumping and pumping your member in and out of her sex. With each thrust, you can feel her inner walls progressively constricting around your spear like a snake. As it grew tighter, the more effort you had to expend, but the pleasure heightened as well.

As you were giving Cinch the banging of a lifetime, she was able to swivel her her head enough to plant a kiss on your lips. With that, it was the catalyst to put you on the fast track to cum. But you weren’t done yet, far from it. You were going to make her your bitch like she nearly made you hers.

With several more good slams against her cervical entrance, your cock throbbed and pulsed with excitement as it expelled another load from your balls, flooding her womb with your seed. You continued to hump and hump her as you came inside her until the load was gone. Looking at her, you found that you load has caused her stomach to bloat slightly. By appearance, it looked like she was two months pregnant.

“Ohhhhh yeeeeaaaahhhh!” Cinch moaned, legs still weak but able to stand. “You’ve certainly improved since last time. How many women did you have, Dr. MILFlove?”

“More than I can count.” You nonchalantly replied as your cock slipped out of her pussy, still just as hard. You had the energy and it looked she was half-way exhausted. You weren’t finished and you were going to fuck her until she can’t walk. “So, I’m no slouch... ma’am.”

With those words, you align the tip of you spear to her anus and thrust forward with all your might. She screamed, gasped and moaned as her ass was invaded by your cock. As Cinch began to process the sensation, pain was soon replaced by a sense of pleasure. Never in all her time of having sex did she once consider anal, but she started to enjoy it.

“Oh god, DO IT!” Cinch groaned in a hoarse tone. “FUCK MY ASS AND MAKE ME YOUR BITCH!”

That was it, any and all restraints were gone. Nothing stopped as you started pounding her in the ass with the fervor of a tiger. Goddamn, her ass felt tight yet pleasurable, like the other times you tapped those holes. In the cacophony of her moans, screams, swears, and yelps, you sped up your ministrations to ensure you held up your promise.

The longer you thrusted, the more your grunts became pronounced. You were close to unleashing yet another load but you wanted to make the pleasure last longer. Using the sheer force of your will, you mustered up your reserve stamina and doubled your efforts as you balls tightened once more.

With one final thrust, your balls emptied themselves once more in a tide of hot white goo. You let out a primal roar as the last of your sexual stamina was ran dry, pulling yourself out of her ass as collapsed to the bathtub floor, dragging the exhausted Cinch with you. As much as you wanted to make small talk and do the occasional post-coital relaxation, you gaze drifted towards the clock in the room.

“Oh shit.” You muttered, snapping Cinch out of her daze. “It’s 10 til 1! We need to hurry up and get ready!”

With a nod, Cinch got up with your support and began cleaning each other spotless. Not a single hint of musk and sex emanated from your bodies. After all that, you got your respective clothes back on and relaxed in the living room, almost as if what happened earlier never did. However, the memory was still fresh in your mind and you savored every moment of it.

It was 1:22 pm and you and Cinch were relaxing in the living room watching the news while you drank some iced peach tea. The quiet calm was interrupted a pair of loud raps on the door that heralded the entrance of Shining Armor. Shining took a quick glance at you as if he remembered you from when he was coach of the swim team.

“Hey, I remember you,.” He said. “You were on CPA’s swim team. What brings you here?”

“Well, I’m mandatory vacation and was looking for something to occupy my time.” You explained. “It’s nice to meet you again, coach.”

As the two of you shook hands, the corner of your vision noticed the approach of Cadence, still as beautiful and radiant as ever. The moment your gazes locked, she gave you a subtle sly smile, like she was remembering what you and her did all those years ago.

“Nice to see you, Calculus.”

Author's Note

I would like to start this off by saying I'm sorry for not releasing the next chapter for this (for better or worse) fine and wonderful series. I would write a paragraph but I won't because I don't want to bore any of you peeps. But the tl;dr of my explanation is work, school, writing ideas for new stories and other IRL shit that would be too much to list.

However, over the course of my semi-stealth hiatus, I've managed to come up with a few more creative ideas for some future chapters. In fact, I would like to share a sample of the next chapter starring Posey Shy, 's mom:

You saw Posey digging through her knapsack and pull out a plastic bag containing something you couldn't identify. She leans over to you and holds one the contents of the bag in hand. It looked like some sort of cookie but it clearly wasn't. It looked like some charred round slice of orange with some sort of stem that some funky scent.

"Here," She said. "Take it."

"What is it?" You asked, suspicion grips you.

"Oh, It's just a little snack. Quite nutritious as well."

You looked at the object with uncertainty. You don't know what that thing could be. But with dinner about two hours away, your hunger overrode your sensibilities as you took the snack and put it in your mouth. As you chewed, the thing had a hint of a stale taste to it yet it was offset by some strangely asian seasoning. You enjoyed the flavor and the semi-crunchy texture.

"Wow, This is good." You thanked. "Where did you get this?"

"My darling Flutter's friend Treehugger gave me these." She giggled. "It was from her personal stash."

As you swallowed the food, your head began to feel light as your senses dulled, almost as if you overexerted yourself during a workout. Soon, you began to hear things that had no visible source, seeing things that weren't really there. There, you realized what you ate wasn't a snack at all.

"What the fuck?" As your vision began to be more distorted, Posey knelt in front of you with an innocent smile. A wave of confusion washed over You as You began freaking out. "What the fuck was that?"

"Shrooms." Right off the bat, you knew what she was talking about. She drugged you with some hallucinogenic mushroom. Your first reaction was to get angry at being tricked into taking an illicit substance. As you were about to raise objections, Posey put a finger to your lips, silencing before you said even a whisper.

"Shhh, just relax and enjoy the experience." Just all of a sudden, as if you've let your phone on, a familiar tune began playing in your mind as Posey sashayed her hips seductively. As your surroundings turned into an undulating void of tie-dye colors, you were uncertain about many things but one...

You were in for one wild trip.