It was a quiet monday after you got done with lunch. You typically don’t eat much and would spend the rest of the lunch period outside drinking a water, minding your own business while listening to your Black Sabbath playlist. While doing your routine of post-lunch relaxation, you began to reflect on what happened last friday. Losing your virginity and with the hot-as-hell dean of the school, you smile with a smug sense of accomplishment that you finally became a real man. Sadly, you couldn’t brag about it because shagging with staff is a taboo, despite you being 18 and the one who initiated the whole thing. It’ll have to be a secret between you and Cadence… or so you hope.

As you were jamming to Paranoid, you saw your friend Ignacio approaching, trying to speak to you but you couldn’t hear a single word because of how loud you had the volume. After a bit of seeing him gesturing you to remove your earbuds, you do so and finally heard what he was saying.

“Yo Calc, what happened yesterday?” Ignacio asked with a puzzled look. “I tried calling you after I got home but you never answered.” You trust Ignacio like a brother, but he has a tendency to be a bit of a blabbermouth. One hint of your affair with Dean Cadence last week and he’ll possibly blab about it, getting you and Cadence into trouble. So, you had to play it cool and tell your half-true cover story.

“I… was busy getting my stuff packed to go when Dean Cadence caught me just as I was about to leave.” You saw Ignacio giving a look of surprise. “I explained my case and she decided to give me a detention rather than suspending me. Also, my phone was outta juice and I couldn’t find an outlet anywhere. I do apologize.” Then and there, Ignacio gave you a neutral look, leaving you uncertain at first whether or not he bought your story. Then, his face switched to that of one that says “Eh, Alright.”, relieving you of your worries... for now.

“So, what was it you wanted to tell me about last week?”

“Well Calc, we have that thing today at the football field. They already brought the water balloons and whatnot. We're just waiting on you now.” Since the seniors were set to graduate in a month, Dean Cadence has authorized them to have a day where they can engage in whatever activity that's school appropriate. Since a good ol’ fashioned water balloon fight was harmless, they were given permission to do so as long as it doesn't get out of hand.

“Ok let's go. We better hope the wicked witch of the school doesn't kill us over this.” You remarked.

“Eh, who gives a shit.” Words like that would do little against Principal Cinch’s wrath, should it ever be invoked. Many of the students of the school liken her to a drill sergeant, only more calculating and cold hearted. She cares more for her reputation and that of the school's than the personal happiness of the students, running it like a tight ship. Students would do well to not piss her off lest they suffer a horrid punishment only she could devise.

After a few minutes walking, you and Ignacio reached the green football field where two groups of senior students were ready for one hell of a moment in their senior year. Once you were with your group, you grab an armful of water grenades and stood with your teammates, ready for battle. As you eagerly waited of the cue, Ignacio walked to the front, pointing his open hand at the opposing team before yelling:

“Attaaaaaaccckk!” Then, as if it were from a play rehearsal, both sides threw their water balloons toward each other, drenching each other in a hailstorm of water and rubber. Splat after splat, the area around the football field became filled with a symphony of water splashing, laughing and swearing. You threw balloon after balloon, managing to hit a few as they threw a several in your direction, only managing to get your legs as you evaded their assault. Then, you locked eyes with the leader of the enemy team, an opportunity to get them where it hurts. You take your last big water bomb and took aim before throwing with glee unbound.

“Stick this up your pipe and smoke it.” You muttered as you turned to your comrades, jumping and cheering with glee as you heard a loud splat.

“HELL YEAH! WHO'S YOUR DADDY?! HUH? WHO'S YOUR DADDY?!” Your cheers were stopped by the progressive shocked expression being directed towards you. You looked at them with a confused expression as you wondered what has them scared. “What? Do I have something on my face?”

They nodded no, still keeping their fearful expressions.

“Is there someone behind me?”

They nodded yes.

“Does that person look angry?”

They nodded yes once again. However, one of your teammates managed to break the silence and said “Turn around.”.

Obliging his request, you slowly turned your body around and come face to face with something you hoped never to see. Standing before you was Principal Cinch herself, hands on her hips, drenched in water, and angry with the fury of 100 wound up pitbull terriers, held back only by her sheer willpower. This was the last thing you wanted to do, especially to her. You could run but knowing how angry she was, she would grab your shirt collar before you could move a single leg muscle. The pure experience of fear kept you in place and even your facial expression didn’t change at all, even as you try to say something.

“Well… fuck.” That was all you could mutter before Cinch grabbed you by your wrist and looked at you with the meanest expression imaginable.

“You... are in a lot of trouble, mister.” She snarled as she dragged you with her back towards the main building while Ignacio and the rest of the seniors looked on with worry.

“Well… there he goes, the end of the road.” Ignacio whispered as he saw you getting dragged off by Principal Cinch. As you were being dragged through the halls of CPA, you were momentarily distracted from your fear by a sight that you didn’t expect but nonetheless mesmerizing. As Cinch was leading you to your office, you couldn’t help but notice her giving her hips some noticeable sway as she walked, making her firm yet thick rear hypnotizing with every bounce. You didn’t expect this from someone who was noticeably older than Dean Cadence. It was amazing to you that someone at the age of 40 kept her form so perky yet graceful. Just the mere thought and sight of her jiggling made one thought dance in your mind:

“Dat Ass!”

… complete with a developing boner. Staring briefly down in horror, you had focus all your energy towards stopping your half-chub from developing into a full-on hard-on, fearing what Cinch would do if she were to find out. You were able to stop it... for now. After a few more minutes of walking, you arrived at her office and she gets you to sit on the chair in front of her desk, briefly walking behind you to shut the blinds on the door, locking it, and flipping the sign to say “Busy”. After shutting the window blinds and dimming the lights, she walks in front of you with a slightly less angry frown.

“Now Mr. Calculus,” Cinch started with her usual authoritative tone. “ I’m very disappointed in you. The behavior you exhibited was completely unbecoming of what is expected of all students and the reputation that this school is known for.”

“I’m sorry, ma’am.” You said softly. “We were given permission to do this. We’re going to clean up afterwards.”

“NO EXCUSES!” Cinch snapped at you, stopping your train of thought. “Now, because of your stunt, I have to change my soaking attire. When I get back, I’ll have your punishment decided.” Just like that, she left for the other room, leaving you to ponder in fear of what will become of you. As you did, you got up and stared out through the window, fearing the worst case scenario of suspension. Being suspended meant you had to answer to your parent to which they’ll chew you out so hard that your ears would be ringing for months. Standing and sighing, you failed to notice the door to the other room creaking open.

“I thought I told you to stay put, you naughty deviant.” You had little time to process what you just heard before you felt a soft, squishy presence against your back while a pair of hands slowly rub all over your chest. “You should know by now that rebellious students turn me on and when I get turned on, I can get uncontrollably... horny.” The sound of the voice was unmistakable. Principal Cinch was fondling your chest as she took a whiff of your musky scent, moaning in ecstasy. Looking in the mirror next to you, you saw that she was in nothing but her bra and panties. You were caught completely off guard, never expecting this to happen, save for a phone call to your parents. However, you managed to get the courage to jump out of your speechless state and ask her why.

“W-w-what are you d-doing?” You stuttered

“I've heard that you have quite the body for sensual pleasure.” Cinch moaned as she sunk one hand down towards your crotch, cupping your erection in her hand. “I just had to try it for myself.” The sensation was overwhelming, slow yet arousing, like she had the most sexual experience out of all the staff in CPA.

“What?! H-h-how?!” You wondered how she knew of your performance with Cadence since she made such a statement. You began to ponder if somehow Ignacio might've caught wind of it or something else you didn't count on. Then, she brought her mouth close to your ear and whispered:

“Just because Cadence and I are co-workers doesn't mean we never talk outside of school. Why, me and her are good friends and she talked to me Sunday night about how you ravaged her senseless. Just thinking about every detail she told me is enough to make me feel wet down there.” Just as she kissed the nape of your neck, she undid your belt and zipper, pulling down your jeans and underwear, allowing your member to stand free and uncovered.

“Hmmm, quite the tool you have there.” Cinch purred as she rubbed her sizeable breasts against your back, gripping your bare cock in her hand. You were speechless as to how she was so good as she slowly yet sensually stroked the length of your penis. But, you were more speechless to the fact that Cadence was the one who told Cinch about your experience with her and now she wanted a piece of what’s between your legs. While the handjob was not as fast paced as your masturbation sessions, you still felt the same rate of pressure buildup. The kissing of your neck, the rubbing of her breasts on your back, and the handjob she was giving you is indicative of her having been with someone in the past and she knew how to please him in this way. As you feel the pressure build up in your crotch, it took all of your willpower not to cum early. You wanted to impress her since you were getting laid with her. Sadly, your capacity to withstand those urges eventually wore out when she bit your neck, sending shivers down your spine and to your crotch.

“Oh god, holy shit!” You grunted as you orgasmed, sending rope upon rope of your hot seed at the wall in front of you. You’ve never felt this good when you usually jack off but that… that was heaven. As you became lost in your post orgasmic bliss, you were turned around by Principal Cinch to see that her lacy bra and panties were on the floor behind her revealing her mature yet perky naked form to you. You were amazed that some woman at the age of forty was able to keep a body that luscious. She had mostly shaven pussy, her breast size is more than the average bust size of the female students but not as big as Cadence’s, and her ass… HER ASS was a sight to behold. It was pretty big but not too big, the right size for a booty.

“I honestly don’t think it’s fair if I’m the only one who’s nude.” You were too quick to notice when she, with one careful maneuver, quickly removed your shirt. “And your shoes and pants too, student.” Complying with her orders, you kicked of the aforementioned clothing leaving nothing on and letting your erection develop once more as Cinch embraced you with your respective nether parts touching, filling you with so much pleasure.

“Cadence told me how good of a kisser you are. Please, do prove it.” Just as you about to let a word out, you principal plants her lips on yours, invading your mouth with her tongue. Just like with Cadence, as Cinch opened her mouth, you invaded her's with your own tongue, pressing your body further against her as your shaft came into contact with her moist, wet nether lips. You enjoyed every moment of the kiss as she walked the both of you to her chair and seating you on it. For a time, you became lost in the kiss’s rapturous feeling before Cinch broke it to get some air.

“Hmmm, I wonder how it tastes.” Cinch breathly moaned as she stared hungrily at your raging boner, licking her lips. “How about I have a little taste.” Just then, she snaked her moist tongue along the length of your member, slowly and methodically. You were paralyzed at the sensation of receiving quit a blowjob, especially from the principal of all people. Normally in a normal fantasy such as this, one would imagine ploughing some hot language teacher but this takes it a level beyond. Here you were, sitting naked on the principal's chair, receiving a blowjob from the head of state of this school. Still reeling from the handy that she gave you, you've built up an improved endurance, ready for what she has in store for you. Just as she gave your tip a playful flick with her tongue, she began to take the entirety of your length into her mouth. For a moment, you could’ve sworn that your eyes rolled into the back of your head as she began bobbing her head up and down your shaft.

“Oh fuck, this is amazing.” You grunted as Principal Cinch kept on giving you head. As you tried to lean up, you were met with a quick palm to your face, sending you back into the chair. Taking time to process what she did, you came to a realization: she likes to be the one in charge during sex. You immediately realize that she’s a person that respects strength and authority. To get the upper hand and be the assertive one would bring her pleasure unbound.

However, your presser was soon built pass the threshold that you could tolerate and you soon climaxed in your principal’s mouth. Spurt after spurt of your cum went down Cinch’s throat as she took the whole of your cock into her mouth, desiring to enjoy every last drop of your seed. After a minute of shooting your load, you began to reel from your orgasm as Principal Cinch brought you to the floor, straddling your waist.

“Relax, just enjoy it. That’s an order, student.” As she purred her command, her lower lips made contact with the tip of your spear, almost sending you unto bliss. “Just for that balloon, I’ll be the one on top. If you aimed it somewhere else, things would’ve been different.” Then, you felt her inner walls swallow your pride as she impaled herself on it. Just like with last friday, your dick went deeper and deeper into her tunnel until it poked at the cervical wall, eliciting a pleasured scream from the domineering principal. After catching her breath from the shock, Cinch began hop up and down your shaft. You enjoyed every minute of her ministrations as she continued to bounce and bounce as her tits and ass jiggled with every movement. It was hypnotic for sure but one thought still lingered on your mind. You wanted to take charge... to impress her. You just had to wait for an opportunity to present itself.

Then, it came as Cinch lowered herself onto you where both your chests were touching. She was still gyrating her hips, holding your face in her hands and leaving your arms free. There it was, the opportunity that you’ve waited for. You brought your mouth to her ears and whispered seductively:

“Hey, you wanna hear something naughty?”

“Oh yes, student. What is it?” She moaned. Thinking really quick, you thought of a cool sounding quote from a video game you enjoyed playing.

“Well… Power shifts more quickly than some people think.” Without an extra whisper, you quickly wrapped your arms around her back and roll over, making you the one on top. Cinch was quite surprised to say the least. “Now, you’ve had your fun. It’s my turn now.”

“My word, I’ve never expected this to happen.” Cinch gasped in reply.

“Well, you could’ve never anticipated what I’m about to do to you… Dear.” There, you began plunging and thrusting into her puffy wet caverns. Anticipating that she’ll try to regain her dominance, you hold her arms down by the wrists as you thrust roughly with all the might you could muster while trying to endure as long as possible. Surprisingly, Cinch wrapped her legs around your waist and made no moves to regain her dominance. Come to think of it, the look on her face tells you that she enjoys being rutted that way.

“OH YES!” Cinch yelled with a lustful, hoarse sounding voice. “KEEP FUCKING ME LIKE THIS! PAINT MY WALLS WHITE WITH YOUR CUM!” You kept thrusting and thrusting your cock into her moist love tunnel as much and as long as your stamina permitted, reveling in every moment her inner walls tighten around your member as her orgasm draws near. With a few more pumps, Principal Cinch let out a pleasured yelp as she coats your crotch with her juices, further clamping your dick with in her walls. With a few more thrusts, combined with the wet tightness around your shaft, you blew your entire load into her womb.

“HOLY JESUS, OH FUCK!” You grunted as you blew load after load of your cum into her pussy as her walls milked you for every drop of your seed in your balls. Over the course a minute, you completely emptied every ounce of your cum into her and your orgasm died down, collapsing on to the floor next to the principal you just banged with puddles of ladycum and seed around you both.

“My word,” Cinch said as she cuddles up to you, tracing a finger around your chest. “ It’s been quite a long time since I was satisfied that much. I suppose I have to thank you for this, Calculus.” Still exhausted and in your post-orgasmic bliss, you could only let out a soft and breathy:

“You’re welcome.” As you began to recover, you began to put your clothes back on as Cinch did the same. Her backup attire was a pair of some denim shorts with a Jimi Hendrix t-shirt. You were honestly surprised she had a thing for rock and roll, thinking that a usually uptight person like her would prefer orchestral music. Just as you got your shoes back on, Principal Cinch hands you a slip for a week of detention for every lunch period you had, taking you by surprise.

“What?!” You gasped in shock.

“Don’t worry, it’s only for a week. We’ve got to have a cover so no one finds out about this.” After hearing her explanation, you began to shake your head in agreement. It was a solid cover, so hopefully nobody would suspect anything, save for your friend Ignacio.

“Well now, run along. And remember, we might run into each other again.” With a sultry look, Principal Cinch excused you from her office. Walking towards your locker, you put the detention slip in your pocket and did the combination lock, opening your locker.

“So, how bad was she?” Nearly bumping your head, you turn around to see Ignacio behind you.

“Not really, I told her that I was the one that organized it. Apparently, she appreciates honesty.” You cautiously explained.

“What did she give ya?”

“A weeks detention for my lunch periods.” You calmly stated, hoping your explanation would hold water to him.

“Rrrriiiiggghht.” Ignacio sarcastically quipped. You knew then he suspected something but you hoped he didn’t know of your exploits. As far as you know, you had ‘reasonable’ conversations that narrowly avoided a suspension. There was one upside to it: you never have to tell your parents about your detentions, knowing how they can get. “Anyways, I’ll be off. I’ll see ya next week.”

“Alright. See you then.” As you walked to your car, thoughts of the two MILFs you banged recently made your pride and ego soar through the roof. But, another thought got you as well. Are all these MILFs somehow connected in some way where every MILF talks to one another? You thought about it but immediately cast all those aside and focused on the fact that you got laid for the second week in a row.

“Damn, that’s one hell of an accomplishment.”

Author's Note

Well, here's the 2nd chapter with more to come. I'm really amazed at how well this story blew up from just the 1st chapter alone. That's what keeps me going. Thank you all for the good reception.

P.S.: Try to find a hidden reference in the dialogue.