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Chapter 14
by
MistressOfTheNightWinds
What consequences come about from the latest rule?
Clothing optional means exactly that
I woke up groggy but my alarm wasn’t going off, that was weird. Then I felt a sensation between my legs and remembered. Vic was in my bed, nude, her big soft titties wrapped around my morning wood. She used her hands to press her boobs around my shaft and worked them up and down. They were big, but not quite big enough to engulf the entire length. So everytime she went down, my tip would be high enough so she could wrap her mouth around it. She was concentrating on her job and didn’t even notice I had awakened. I tried to not move or make a sound but the sensation of a pair of huge tits around my manhood was too much. I groaned and lifted my but up a bit to give her a better angle. She glanced up and smiled “Good morning master.” Then went right back to work, increasing her pace. Both hands were holding her breasts in place, but she was in a good enough position so my balls were rubbing against her navel, the combination felt amazing. I only lasted another minute before starting to cum. The first rope of cum shot up and landed on my belly before Vic could seal her lips around me. The rest of my load was dumped in her mouth. With her lips still around my tip, sucking up every last drop, she continued to move her boobs up and down the best she could, milking me.
Once I was finally empty, she licked the cum from my body that hadn’t made it to her mouth. All done licking me clean, she moved up, and cuddled against me. Her breasts on my chest, one leg over my waist and her pussy pressed up to my leg. She wrapped a hand around me and absentmindedly stroked by naked body. I usually sleep in only boxers, so she must have taken them off before beginning the tantalizing titty fuck. With a soft, sultry voice she whispered in my ear. “Is there anything else I can do for master?” I responded with a deep kiss, then “Go make us some breakfast.” She was having trouble breaking away from my lips, her hips now gyrating, rubbing her pussy against my leg. She was humping my leg! If there was ever another woman who was more **** for a fuck, even after last night.
A few more kisses and she finally stood and walked out, glancing back with a mischievous grin and working her ass, making sure she gave me a good show. I watched her swaying, perfect ass disappear from view and a moment later heard the sound of a refrigerator door open and pans clanking. I laid in bed for a few more minutes before heading into the kitchen myself. I watched Vic, naked, hips swaying side to side as she fried up some eggs and bacon. We sat and ate, sitting at my kitchen table, both of us in the buff. After we finished, she looked at me expectantly, waiting for her next orders. “Come clean me off in the shower.”
We got into the shower together. Vic soaped up her naked body as I watched, making sure to get her breasts extra soapy. Then she pressed herself against me and, using her tits a loofah, began to clean me. For my part, I just stood there and enjoyed it, not having to do a thing. She rubbed her boobs all over my front first, then did the same with my back. She even shampooed my hair for me. By the time she was done, I had never been so clean in my life. With my upgrades, I was good and ready for round two, my dick hard and pointing straight up. Vic soaped up her hands and started to work my shaft, staring at it, licking her lips. “Is there some you want whore?” I asked her. She looked up at my face “OH Master, forgive me! Its not my place to ask anything of you.”
After a moment I responded, “Which hole do you want it in whore?” Her eyes wide, “My ass! Please master! Fuck me in my ass!” I turned her around and, without being asked, she put one foot up on the lip of the shower stall, bent over and place her hands on the wall for support. I put the tip of my cock at the entrance to her asshole. As I pushed slowly in, Vic pushed back, willing me to go deeper. When I was all the way inside her, I said “Is this what whore wants?” “YESS!” With my thick cock stretching her tight asshole, I began to fuck her relentlessly while Vic screamed “HARDER!”
I kept going, hot water streaming over us both. Eventually, I came and shot my load into her ass. After the orgasm subsided, we had to clean up, again. We got out and something caught Vic’s eye, she was glancing at it nervously as she dried off. She was looking at the clock, she must have somewhere to be. Well, so did I. “You can go ahead and leave whore, I have to get to work.” She smiled and kissed me, then got dressed quickly and left.
After using Vic twice as my own personal cumdump, I should have been drained. But with my recovery time decreased with a rule, I was horny again in no time. I got to school much earlier than I normally do. There weren’t many students there yet, but the few that were were fully dressed. No matter, I still had plenty to look forward to. I headed to the teacher’s lounge and walked into another argument, this was around the clothing optional rule. I chuckled to myself but remained silent. Just as it was starting to get really heated with voices raised, in walks Ms. Clark fully nude. “Oh, good morning everyone!” Everyone arguing fell into a sudden silence at the site of a fellow teacher walking around naked.
Ms. Clark was an artist, and always a bit of a free spirit. But this was something else. I was expecting to see some naked women today, but not a teacher and, at first, I couldn’t understand why. Then it dawned on me, the way I wrote the rule, I didn’t specify any specific group of people, just the organization of Evergreen Academy. Which means that it applies to anyone who happens to be on campus. Wait, does that mean…? Could I? Noooo… Ms. Clark didn’t pay anyone any mind and went about her business, humming to herself. She got her coffee and continued humming as she walked out the door.
The rest of the teachers were dumbfounded and didn’t know what to say. Even the ones vehemently arguing against this new rule were at a loss for words. I kept thinking about, I could do it, no one would be able to stop me. Fuck it, I thought to myself. I took my clothes off right then and there, with at least a dozen other teachers watching dumbstruck. I stowed my lunch in the fridge and went back into the hallway. First period would start soon, so students were arriving in droves. I strolled through the hall, naked as a jaybird looking around. I was getting a lot of looks from the students, some lustful, some embarrassed, some angry. A few girls were just topless with skirts, the rule about optional clothing could easily be interrupted as partial. But I did see a couple that were completely nude.
My dick was sticking up, hard and swinging back and forth as I walked. I got to my classroom and waited for the bell, doing breast inspections as students filed in one or two at a time. Adriana was completely nude, which wasn’t surprising. She stared at my hard cock during the entire inspection then started fingering herself when she sat down. Himari walked in, bypassed the line and sat down. After I finished and the start of class bell rang, I confronted her. “Himari, are we forgetting something?”
“I’m not forgetting anything! I’m not subjecting myself to your filthy paws ever again! Especially when you’re naked with a hard-on!”
“Himari, to the office. Principal White can deal with you.” She stormed out and I began my lessons. Not more than ten minutes later, the door opened and in walks Himari, topless with her hands over her small breasts. Principal White was in the doorway and motioned me out. Once in the hall with the door closed, she told me. “I’ve decided Himari’s punishment for violating the breast inspection policy will be to go the rest of the day without a shirt on. She’ll be able to get her clothes back at the end of the school day. If that doesn’t teach her to follow rules, I don’t know what will.” That will have certainly have an effect on her, you could be sure about that. “Alright, that seems a little harsh, but its your prerogative.” She lingered for a moment longer. “Was there anything else?” Her gaze went down to my hard dick. “No, nothing else.” She stared for another moment before turning and walking away.
I went back in class and continued teaching. Himari was doing her best to cover herself while taking notes, but eventually gave up, letting her brown nipples fly free. Adriana had finished herself off and was half asleep. Later in class, I was pondering about what to do with Himari. I had put an exercise up on the board which my students were diligently working on, giving me a few minutes to think. The beginnings of an idea started to take shape in my mind. After some more thinking, I pulled out the Rulebook and grabbed a pencil.
Evergreen Academy
New Rule: I am the head and sole member of the Human Sexuality department. I am responsible for making sure all students in the senior area campus are well-versed in all aspects of sexuality. Lessons may come in any form at my discretion, including but not limited to: touching, groping, licking or penetration. One-on-one tutoring is also acceptable and can be performed anywhere and anytime on campus or in a student’s home.
I had a very specific idea in mind for Himari, but that would have to come later. Adriana had her hand up. “Yes Adriana?”
“Mr. Doe, I can’t concentrate without an orgasm and I can’t finish this assignment if I can’t concentrate. Can you help me?”
“Adriana, you just had one.”
“Yeah, but it wasn’t that good, I really need your dick.”
“Alright, I’ll be right there.” The other girls stared at Adriana in astonishment. I walked back and Adriana sat on top her desk and spread her legs. I got right to work and fucked her brains out (not sure how that’s going to help the concentration), then gave her a nice creampie. The rest of my students watched, except for Hiimari who had her head over her work and tried her best not to look back. But the moans and screams got to her, she finally gave in and glanced back at me fucking Adriana. I don’t know what she was thinking, maybe she hated me, maybe she enjoyed the show or maybe she was jealous.

After I finished inside Adriana, she thanked me and got back to work, dripping my cum all over the floor. I was still naked, my cock wet with cum and pussy juice and I’d just fucked a student in the middle of class with ten other girls watching. That was my first exhibitionist showing and it was incredibly exciting. Yesterday with Caitlin, the door was open, but only one person saw, and then, only for a brief moment. I just came inside someone’s pussy as a bunch of other people watched, it was unbelievable.
First period finished up and then I did my breast inspections to a class of fully clothed students. Second period went by fast, then girls lined up for third period. It was all routine by now, groping and sucking nipples as I pleased. With one exception, Caitlin was 4th in line and she was naked. I wasn’t expecting that with how conservative she and her family was. But, when I thought about it, it made a kind of sense, she was now able to explore all her repressed urges and desires.
Caitlin was at home in her room the day before. She was working on her skirt, trying to get it shorter when she heard about the new rule. She stopped what she was doing and thought about it. Could she really do that herself? Walk around school partially or fully nude for everyone to see? Just the thought of it was turning her on. She got even more turned on at the thought of sitting in Mr. Doe’s class, him staring at her bare breasts and vagina. She suddenly got hot and knew that she was horny. The earlier studying in the library provided a fountain of new information. Her door didn’t have a lock and her parents had a habit of walking in without knocking. She’d have to be more discreet. She was still in her school uniform, but dressed for home, long skirt that fell below the knee, panties and bra underneath. She headed to the bathroom, locked the door, took off her panties, pulled up her skirt, sat on the edge of the bathtub and began to touch herself. She had never done this before but read a little about it earlier during her research. Even then, she still didn’t know exactly what to do, so she just started exploring, rubbing and touching in different directions and pressure to see what felt good.
After a few minutes of exploration, she finally found a good spot, her finger going around in a circle, rubbing the same spot Mr. Doe had earlier. Pretty sure she was now working her clitoris, she kept at it. Her breathing began to get more rapid, yep, that was the right spot. She kept going, closed her eyes and thought back to the memory of Mr. Doe being inside her, her naked body pressed up against his, breasts brushing against his bare chest. At the recollection, she put two of her own fingers inside her and felt her own wetness. She got faster and faster, going back and worth between rubbing her clit and pounding her fingers inside her pussy. Her fingers were well lubed with her own juices. She climaxed a moment later, clamping her free hand over her mouth to stifle her scream of ecstasy.
The orgasm washed over her, and she wanted more, but there was a knock on the door, her mother. “Caitlin, are you ok in there? I thought I heard screaming.” Caitlin quickly stood up and got her panties back on. “Um, yeah, almost finished.” She flushed and turned to the sink to wash her juices off her fingers. She could still feel the wetness of her vagina and her panties were probably getting soaked. She checked herself in the mirror and made sure her clothes were straightened out before leaving the bathroom to face her mother. “Was that you I heard in there? What were you doing?” Caitlin replied with a saying her mother was constantly feeding to her. “Ladies don’t discuss such things. And I didn’t hear any screaming.” Her mother straightened her back and tilted her head up at hearing her own words shot back at her. “Humf. Well, now that your finished in there, your father and I need to speak to you, so join us in the living room.”
“Yes mother.” Caitlin didn’t know what they wanted to talk to her about, there was no way they could have known what she just did, could they? They passed by her bedroom and her mother glanced inside. Caitlin was used to the lack of privacy, so she had stowed the shortened skirt under her pillow, nothing looked amiss when they walked by. Now in the living room, standing before her parents seated on the couch, hands clasped behind her back, head tilted toward the floor, she was scared to ****. What did they want to talk to her about? Did they know what happened at school? No way, if they had, they would have punished her severely the second she got home.
After a tense few minutes, her father spoke. “We know about this dress-code change at school.” WHAT!? How could they know about that? They thought the previous uniforms were too revealing, if they knew I wasn’t allow to wear underwear anymore with a shortened skirt...Oh, this was bad, real bad! Her father continued “Don’t worry, we talked to the principal and filled out a form to get you exempt for religious reasons. You’ll go to school in your normal uniform, you won’t be wearing any of those whore-clothes, is that clear?” “Yes father.” Wait, if they knew about that, did they know about the new clothing optional rule? Apparently they did. “And this ‘clothing optional’ malarkey I just heard about, well, if you ever see anyone like that, you are to keep your eyes glued to the floor, then you let us know straight-away. I’m already talking to a darn attorney about it.” Caitlin had never seen her father so worked up before. He took a moment before continuing. “I apologize for the language, this whole situation has me in a tizzy. Now get back to your studies.” “Yes father.”
She went back up to her room and thought about what just transpired. One minute she was touching her privates and the next minute she was standing in front of her strict parents getting lectured about school clothing. Could she keep up this double life with constant hiding and lying to her family? She couldn’t exactly tell them she had sex with a teacher today. Yeah, that wouldn't go over well. She drummed her fingers on her desk and pondered. She would just have to do her best to keep her new-found sexuality a secret. She thought back again to Mr. Doe penetrating her and felt the wetness again. She wasn’t going to get much studying done tonight.
The following day she arrived to school and walked through the hallway to her locker. She still had her underwear on and the longer skirt, with the shortened skirt in her back-pack. She was still conflicted about what to wear today. Mr. Doe and most of her 3rd period class would see her exposed breasts anyway, so wouldn’t it make sense to just go topless? And if she went topless, did it make any sense to keep the short skirt on? As she was pondering these things, another girl she didn’t know walked by, fully nude. As she stared at the girl’s ass walking away, she saw another even more bizarre sight. It was Mr. Doe, but he was naked too! She couldn’t believe it! He just walked out of the teacher’s lounge, nude, showing off his big dick. She had seen him naked the day before, but this? This was different.
She quickly turned her face away and stuck her head in her locker hoping Mr. Doe wouldn’t notice her. He didn’t even glance in her direction as he walked by. She could feel the heat in her pussy again. She now desperately wanted Mr. Doe to turn around and fuck her brain outs right there. And the thought of him lusting over her naked tits and pussy...Fuck it, she thought to herself. If other students can do it and Mr. Doe can do it, so can I. She starting heading to the restroom, then realized how dumb that was. Everyone was going to see her anyway, there was no reason she couldn’t do it right there in the hallway. So she did. She stripped of her clothes and shoved them in her locker, then, with head held high, made her way to her first class of the day, fully nude.

Caitlin, normally the most conservative, demur and shy of any student, stood before me naked, awaiting her breast inspection. I was still seated, myself also without any clothes and all the boob touching had me hard. Before I could begin on Caitlin, she said. “Here, let me get you a better angle.” She then sat down on my lap, straddling my legs, just like yesterday. She probably didn’t know any other way to do it. As my hands felt her up, she made herself as tall as possible to get her boobs closer to my face. As I kept squeezing and groping, she said “Mmmm, milk me. Milk my titties! Please Mr. Doe, I need my tits milked!” Always one to try fulfill a student’s request, I happily began sucking her nipples. The second my lips attached to a tit, she starting grinding her pussy against my hard cock. She was moaning now, head titled back and chest thrust forward. She wanted it bad. Without even asking, she stopped grinding her clit against me, grabbed my cock and impaled herself with it. Her pussy was still as tight as the last time. I took a firm grasp of her ass, stood up, pinned her against the wall and starting pounding her wet needy pussy. She wrapped her arms and legs around me to help support her weight as I drilled her. She screamed “YESS! FUCK ME! FUCK MY WET PUSSY!!” Normally, I would have never been able to do this, it wasn’t exactly easy to hold a human being in the air for any extended period of time. But with the muscle and fitness upgrades I had given myself and the fact Caitlin wasn’t as heavy as I thought she would be, I managed to keep her up in that position.
The other girls were now standing around us, watching. I heard some whispers and a few “Oh my god! I can’t believe this!” Having another fuck-session in full view of my students only made my crazier. Caitlin wasn’t much better, her nails digging into the back of my neck and her ass slapping against the wall with my deep thrusts. I wasn’t sure how many times she had cum, but judging from the shrieks, it was more than a few. I looked at her as I got closer and asked “Where do you want my load?” “Inside me! Cum inside me! I wanna feel your seed inside my pussy!” I heard a “What the fuck?” from one of the other girls watching. A moment later I was shooting my thick sperm inside Caitlin’s tight cunt. She grabbed the back of my head and drew me into a deep kiss, probably her first ever which only intensified my orgasm.
After I finished, she kept kissing me. I would have kept going, but Principal White had come in “Mr. Doe, I know you’re still adjusting to this new position you have, but you still have other responsibilities. So please finish up with Ms. Caitlin and get class started.” I pulled away from Caitlin and let her down. “Yes, of course Principal White. My analogies.” Caitlin almost fell over as her feet hit the floor, but I helped steady her. She walked to her desk and collapsed, exhausted and, hopefully, satisfied. There was a small pool of cum beneath where we were just fucking, another below Caitlin’s desk as it leaked out of her and another where I fucked Adriana earlier. The cleaning staff was going to **** me. I finished the remaining breast inspections under the watchful eye of Principal White as quickly as I could, then began lessons for the day. Principal White hung around for a few more minutes, glaring hungrily at my dripping cock, then turned and left.
Caitlin sat down in her chair in Mr. Doe’s room, feeling his cum still inside her, some of it dripping out onto the floor. She really loved the feeling of his seed inside her. She wondered if she would get pregnant from all that sperm drilled into her womb. But Mr. Doe said he couldn’t get her pregnant. Her pussy was quite sore now after that pounding and her ass sore as well from getting it banged against the wall. But was worth it, she lost count how many times she orgasmed, that thick long cock was so much better than her fingers. She watched as Mr. Doe finished the breast inspections for the other girls. She saw how he enjoyed sucking nipples and she liked it when hers got sucked on too. She wondered what it would be like to suck on another girl’s breast.
What to do with Himari?
The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 15, 2026
by ErnestDuke
Created on Jul 27, 2017
by ashes2ashes
You can customize this story. Simply enter the following details about the main characters.
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