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Chapter 25 by MistressOfTheNightWinds
Is it possible there’s someone more repressed than Caitlin?
Apparently
The next morning, I added a rule
Evergeen Academy
Old Rule: Caitlin does not have to pay tuition to attend classes.
Then, I took Caitlin to school with me. She opted to go bra and panty-less, that way she wouldn’t have to worry about it once she got to school. Vic and I told her she could wear whatever she wants when she was in either of our homes, or nothing at all. Outside home or school, she would have to dress normally and Vic promised to take her out shopping that evening. She also had her new butt-plug in.
We got to school and Principal White pulled me aside the second I got through the door. “Mr. Doe, Farah’s mother has scheduled a meeting with me for this afternoon and she would like you to attend as well.”
“Oh? What about?”
“Her daughter wants to get exempt from the dress code and inspections.”
“I see. I didn’t know we even did that kind of thing.”
“We do, but I don’t really think its in the best interest of the students. With the way things are, girls and teachers running around naked, I just don’t think it would be good for a student here to be completely covered. It opens up too many possibilities for bullying and other things. So, how has Farah been doing?”
“Well, I’ve only had her for one class so far, and she was very shy.”
“Yes, I noticed that yesterday when I observed her breast inspection. In any case, this is just something she is going to have to get used to. Any suggestions?”
“Well, Caitlin had a similar issue, but she got over that quickly once I started fucking her regularly. Maybe something like that would work here?”
“Hmmm, maybe. Alright, I won’t keep you any longer, and don’t be late for the meeting.”
“Of course.” I proceeded to strip right in front of Principal White, then headed to class. I had Farah for first period and she was last in line, just like the day before. She was already in the appropriate dress code this time, short skirt, no bra and no panties. She clenched her eyes shut while I completed my inspection, groping, squeezing and sucking her breasts. Once she took a seat, I rolled my chair out from behind my desk so everyone could see me.
“Himari, come here and sit on my cock.” As usual, Himari looked disgusted, called my a perv but did as she was told. She came over and began to straddle me. “Not like that, turn around and take it in your ass.” A few gasps from the other girls, but Himari complied. She turned her back to me and lowered herself down, using her hand to guide my cock in her ass. I made sure to angle myself and my chair so that Himari would be staring directly at Farah as she started to bounce up and down my hard cock. Farah was looking away, eyes closed and hands over her ears. I finished inside of Himari, she took her seat, then I started the day’s lessons. Farah was the first to bolt out the door the second the bell rang.
Later, I played with Caitlin. I used and creamed her pussy from behind while playing with her plug. The rest of the class watched. I made it through the rest of the day and went to the principal’s office after the final bell. I walked in to find an astonished and appalled woman in a full abaya, the same woman I fucked the other day in the cafe. She wasn’t expecting to see me, especially not naked. Principal White kicked things off while we waited for Farah. “Mrs. Hadi was just telling me about her religious beliefs and how women must be covered at all times.” It took her a few minutes to overcome the shock of seeing a naked man walk in and sit down.
“Um, yes. In my culture, women must be modest and their bodies covered at all times. I want my daughter, Farah, to be exempt from the normal dress code.”
“You work down at the coffee shop, right?” I asked but was met with silence. “And there’s a new dress code there, right? I believe you have to be topless while at work.” She blushed at that, remembering what happened to her a few days prior.
“Yes, but that’s different. I have rules I have to follow at work.”
“Its no different than here. Farah has rules to follow at school.” Farah walked in while I was saying this. She kept her eyes on the floor, trying to avoid looking at her naked teacher.
“Yes, I realize that, but school and workplace are different. I voluntary took that job knowing the rules. Farah doesn’t have a choice.”
“We don’t always have a choice. I think this is a teachable moment for Farah. She needs to learn that, sometimes, there’s things she has to do that she doesn’t like. Are you aware of the other rules here at Evergreen Academy?” She stared at me, but didn’t say anything. “You’re aware that I have to give Farah a breast inspection before she enters my class?” She turned even redder and looked away. “I’ve seen and touched your daughter’s breasts already. As well as yours. There’s nothing to be embarrassed about.” Farah snapped her head up and looked at me, stunned by that revelation. Even Principal White was surprised. “I understand your culture is different, and I appreciate that. But you have to understand, not every culture is like yours. Here in this school, we aim to give our girls a full educational experience on a broad array of subjects. Including sexuality. I’m actually the head of the Human Sexuality department. I tell you what, why don’t I do some one-on-one tutoring with Farah this afternoon?”
“You mean you’re going to…defile her?” Mrs. Hadi asked.
“I wouldn’t put it quite like that, but I think it would be good for Farah to expand her boundaries, get out of her comfort zone. Learn that sex is a natural part of life.”
So far, Principal White had been quite, but she took the opportunity to speak up. “I think that’s a wonderful idea. Farah and Mr. Doe can go back to his room for some extended lessons and I’ll stay here with Mrs. Hadi until you’re finished. I can show you around the school grounds a bit. You probably already had a tour when you enrolled Farah, but those are always limited, I can show you a lot more of what we have to offer.”
The mom thought for a moment, looking at her only daughter. She came from a very strict home. She had only had relations with two men. Her husband, who had left her when she got pregnant, and this naked man sitting in front of her. She remembered the first time with her husband, it was quick, over in just under a minute. But with Mr. Doe, she had never felt like that before. She didn’t even know what happened to her. As she was riding him, his dick inside her, her whole body and her privates clenched and a euphoric feeling washed over her. It was the single most pleasurable experience of her life. She wanted Farah to feel the same thing. Farah had always been shy, never connecting with people, never having many friends. It actually made the move here easier. But maybe Mr. Doe was right. Maybe now, on the brink of graduating high school and heading off into the world, her daughter needed to expand her horizons. It wouldn’t get any easier as she got older. This was an all-girls school, but in college or when she got a job, she would have to be around men. Maybe this was for the best.
Mrs. Hadi pondered for another minute before sighing. “Alright.” Farah was dumbstruck. She thought there was no way her mother would go along with this. She had always kept her body covered, even when around female members of her family. And now she was **** to wear a very short skirt and not allowed any underwear. It was humiliating. And there were other girls walking around naked all day. And on top of that, she had to expose her breasts to a male teacher and let him touch her. And now, her mom was was going to send her off with this man to do…what exactly? She had tried not to watch when he sullied the other girls in class. This morning was worse though, the way he had one of the girls turn around and sit on him, putting his erect penis in her but, not even her womanly privates, and she was right in front of her, staring at her the whole time. She looked like she enjoyed it. “Farah, you’ll go with Mr. Doe and I’ll go with Principal White for an extended tour of campus.”
Farah obeyed her mother. I led her back to my classroom. “Ok Farah, do you know what’s going to happen?” Silence. “I know you try not to watch what I do to the other girls in class, but surely you know.” More silence. “I know this might be awkward for you at first, but I promise, once you try it, you’ll love it.” Not a sound. “Well, why don’t you come to the back with me.” I led her to the bed in the back of my room and sat down. She stood in front of me, still with her uniform on. I reached up and began to unbutton her vest, then started on her blouse. She started to fidget nervously when I got far enough that she showed some skin. When the bottom few buttons were undone, I leaned forward and kissed her belly. She wasn’t expecting that and gasped. I kept working on her blouse until it was fully unbuttoned. “Go ahead and take that off.” As slowly as she could, she let the shirt fall down her arms and onto the floor. I kept up with my mouth, licking and kissing her bare abdomen and underboob, groping and exploring with my hands. My hands ran around the back and unzipped her skirt, letting it fall, revealing her perfect pussy. There was some hair, but unlike her mother’s, it was neatly trimmed.

“Well, you’re certainly not as innocent as you claim to be.” I said as I playfully pulled a tuft of pubic hair. I kissed down her body reaching her vulva, and ran my tongue over her clit. She bent her knees and closed her legs. I ran my hands up the back of her thighs, took hold of her ass and threw her down on her back on the bed. She yelped in surprise and terror. I grabbed her knees and had to pry them apart, finally getting a good look at her puffy brown pussy lips. I dove right in and began eating her out. Running my tongue in a circle around her clit, then up and down, then side to side. She let out a few moans. I had to keep a good grip on her knees to keep her legs open, but after a while, she relented and I was able to move my hands up and grope her tits.
A few minutes of eating her pussy, her legs raised, toes curled and she screeched. I kept licking her pussy until the came down from the orgasm. Then I moved up, put the tip of my cock on her lips and slowly worked it inside her. She was soaking wet from climaxing, but still very tight. I had to work it in and out a few times before she loosened up enough to get all the way in. Once all the way in, I asked, “Farah, how you doing so far?”
“Wha…I…I don’t…AHHH” Her eyes rolled back in her head and she clenched again, thighs and pussy walls tightening around me. She was laying on her back, hands up against the bed, not moving or doing anything. “Farah, put your arms around me. Good, now wrap your legs around me as well, don’t be afraid use your hands.” She followed my directions without hesitation. She was getting into it, her body rocking in rhythm to my deep thrusts. I kissed her lips, she tried to pull back but couldn’t. After a few moments, she closed her eyes and kissed back, enjoying the feeling of my tongue in her mouth.
Her pussy was so tight, it didn’t take long for me to cum. I didn’t warn her, I just thrusted deep, held in place and filled her pussy up with my thick cum. When I finished flooding her insides, I pulled out and lay back. “Alright Farah, now its your turn. Get on top of me and take my cock inside your pussy.” She paused and looked at my like I was deranged. “Oh, uh, ok.” She got on her knees, swung one leg over, spilling gobs of cum out in the process. Then she lowered herself down and tried to grab my tip with her pussy instead of using her hands. She actually succeeded.
Once I was at her entrance, she dropped down slowly, taking my long shaft inside once again. Once all the way down, she stopped, not knowing what to do next. “Ok, now you’re going to grind against me and use your legs to bounce up and down. Just listen to your body, try different things until you find what feels good.” She placed her hands on my chest for support, then starting to grind and work my dick. It took her some time to figure out what felt good, but when she did, she went at it like a drunk monkey. She howled in pleasure as she hit just the right spot with my thick cock and came again. And then again a few moments later.
This went on for a while, I lost count how many times she came. She had me so deep inside her, working her hips so my tip would rub her g-spot. It almost seemed like one long continuous orgasm. I eventually came again, filling her pussy with a second load. Not much of it remained in her pussy, it all ran out and down over my cock. When she felt my second load, she stopped and collapsed on top of me, completely spent. I could feel her pussy still twitching. “So, Farah, that wasn’t so bad, was it?”
“Uhhh…” She laid on top me for a bit, not moving, trying to catch her breath. When she finally sat up, she asked, “Is this what its normally like?”
“That’s what its supposed to feel like, yes.”
“Oh.” She looked down at her own naked body, still impaled on my cock. “I…I didn’t know.”
“Well, that’s why I teach. You can go ahead and stand up now.” She stood on shaky legs, cum and pussy juice running down her thigh.
“Can um…Can I get dressed now?”
“Yeah, of course.” I watched her put her clothes back on. She was cognizant of me watching her and got dressed as quickly as possible.
“What about this…stuff?” She motioned to the cum on her thighs.
“Leave it. You can clean up when you get home.” She didn’t seem too happy about that. We left to find her mother and Principal White. We walked down the hall, me naked along with a girl whose gaping pussy-hole was still leaking. We found Principal White and Mrs. Hadi a few minutes later in the gym, they were watching the basketball team run drills. Mrs. Hadi took one look at her daughter and almost fainted. “Farah, what…what happened?”
“Its nothing, I’m fine mom. Can we go?”
“Yes, yes, of course.”
Before she left, Farah glanced back at me, “I’ll see you tomorrow Mr. Doe.”
Principal White turned and asked me, “Well, how’d it go?”
“Oh, I think she’s going to fit in just fine here. Just fine indeed.” My eyes were on the basketball team and Principal White followed my gaze.
“Can you at least let them finish practice first?”
“I guess.” She shook her head and left.
What does John do with the basketball team?
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 17, 2026
by Ggnt
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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