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Chapter 29 by MistressOfTheNightWinds
What kind of plan?
Friends from college
A few buddies from college were going to be in town and they wanted to get together and catch up. The plan was to meet at my place Friday evening then figure out what to do from there. Unbeknownst to them, I already had a pretty good idea of what was going to happen. I’d already filled Vic in about my plan, but not Caitlin, it would be a surprise for her. Before things got started, I needed some prep work. I pulled out the Rulebook and made a new header for my address.
234 Edgewood Pl.
New Rule: Any men at this address cannot impregnate anyone or catch/transmit any STDs.
New Rule: Men at this address completely recover from an orgasm within one minute and produce twice as much sperm as normal.
The guys arrived early in the evening at my place, Vic had Caitlin next door, waiting for my text. The first to arrive was Mike, life-long bachelor and connoisseur of women. Next Brad and Phil showed up at the same time, having driven together. Brad had been married for almost ten years now, but hadn’t gotten any sex for the last four. Phil was recently divorced and a bit depressed. Last to arrive was Jake, an up-beat stoner who couldn’t hold onto a girl for more than a few weeks.
We sipped on some beer and munched on the snacks I had laid out while talking and joking. After a bit, they started to get antsy and wanted to go out.
“I thought we could stay in tonight. Actually, I have a bit of a surprise for you.” I told them. Their curiosity was peaked. I texted Vic and a moment later, she and Caitlin walked in to find four hungry men staring at them. “This is my neighbor Vic, and one of my students, Caitlin.” They looked at Vic for a moment before switching their gazes to Caitlin, wearing a short sundress and clearly braless. “Caitlin, come over here.” Caitlin hesitated for a brief moment, not sure what was going on and afraid to get her hopes up, but quickly walked closer to let the guys get a better look at her.
I gestured to Caitlin, “So here’s the deal, Caitlin is going to strip naked, then you all are going to fuck every one of her holes until she can’t take anymore, then you’re going to fuck her again.” Caitlin’s head snapped over to look at me, her eyes lit up in excitement, she smiled wide and quickly pulled her dress up over her head, revealing her perky tits and perfect pussy.

The guys looks at each other, then to Caitlin, then back to me. “Dude, are you fucking serious?” Asked Mike. They all looked taken aback at this naked high school student standing in front of them. Brad, the only one that was married, turned red and only looked for a brief second before trying to avert his eyes. The others continued to stare in disbelief. Before I could respond, Caitlan picked the hungriest-looking of the bunch, Mike. She wrapped her arms around his neck, pressed her naked body against his and shoved her tongue down his throat.
“Well, does that answer your question about me being serious?” Mike didn’t need any more invitation, his hands were instantly all over Caitlin’s body, feeling up her ass and tits. A moment later, Caitlin was tearing Mike’s shirt off then grabbing wildly for his pants, drunk with lust. After Mike’s pants were off, he dropped to the floor with Caitlin on top and she took his cock and guided into her greedy pussy. She moaned as it penetrated her tight wet hole. “Well, what are you waiting for?” I told the other guys. “She’s got two more holes to fill, get to it!” Phil and Jake looked at each other, then started stripping. Phil stood in front of her and Caitlin readily took his cock in her mouth, eyes rolling in the back of her head as she did so. Jake got on his knees behind her, pulled out her but plug, then put his cock in her ass.
Brad was looking away, only glanced at the show for barely a second before walking over to me. “Dude, I can’t be part of this, I’m married!”
“When’s the last time you got laid? Three years? Four? You’re always complaining about it. Here’s your chance to get some pussy.”
“Dude, I’m married, what about Maria?”
“She’ll never know!”
“I’d know, I can’t do that to her, I’m out.” He headed towards the door.
“Ok Brad, you don’t have to do anything, you can still stay and watch. Brad!” It was no use, he was out the door and gone. I looked back at a nude Caitlin getting railed by three cocks at once. The guys were finally starting to get a good rhythm going, Mike and Jake’s cocks pumping inside her, pushing her mouth forward onto Phil’s with every thrust. I sat down on the couch with Vic, put my arm around her and fondled her breast as I watched my cock-hungry student get pummeled by three men. Another few minutes and Mike said “I’m close, I need to pull out.”
“No, cum inside her.” I told him.
“Dude, what the fuck!”
Caitlin pulled off the cock in her mouth long enough to say “Do it! Cum inside my tight little cunt! ARGHHH!” A second later, Mike exploded inside the girl’s pussy, shooting more jizz than what he was used to. “OH GOD YES! I love the feeling of thick cum in my pussy!” I chuckled and thought back to the shy, reserved girl from just a few weeks ago. I’d had the Rulebook for less than two weeks, and in that time, so much had changed. Not least of which was the naked redhead in my living room getting fucked by three of my friends. And she only wanted more. “More! I want more! I need another cock in my pussy!”
“Mike and Phil, why don’t you switch?” I told the guys. They all took a break and pulled out of the girl while Mike stood up and let Phil take his place on bottom, putting his cock in Caitlin’s pussy. Jake went back to her ass and after a minute of rest, Mike was getting hard again and decided to try out the girl’s mouth. “Well Mike, which is better, pussy or mouth?”
“Her pussy is the tightest I’ve ever had, but she certainly has some skills with her mouth. I suppose that’s your doing?”
“I am a teacher after all.” I said as I chuckled. The fucking went on for a while. Jake came in her ass, Phil came in her pussy, Mike came again but shot all over her mouth and neck. They switched a few more times, making sure each one of them fucked every hole at least once. Her pussy and ass were full so they took to pulling out and cumming on her naked body. I lost count of how many times each of them came. By the end, she was drenched in cum from head to toe. Vic and I were still on the couch and the fuck-show in front of us had us both randy. We fucked each other on the couch while Caitlin was getting railed on the floor.
After the guys finally started getting tired, Caitlin rolled back on the floor spread eagle, covered in cum, eyes closed and exhausted. “Caitlin, are you finally satisfied?”
I got a very weak “Uh-huh” in reply.
“And you guys, did you all get enough?” The three of them, breathing heavy and barely able to stand looked at each other, then to cum-drenched Caitlin, then back to me.
“If you ever need us again for something like this, don’t hesitate to ask.” They cleaned themselves up before leaving. Caitlin was completely out of it. Vic and I carried her to the shower and got her clean before putting her to bed. All in all, it was a good night. I certainly enjoyed seeing Caitlin take three men at once, and I had Vic to get me off. But it was too bad about Brad. Hmmm, a thought occurred to me about how I could help. Maybe a little rule to help his sex-life. I pulled out the Rulebook and made a new header.
Brad Miller household:
New Rule: Brad is guaranteed sexual intercourse at least once a week. If his wife is not able to or does not want to, Brad may have sex with someone else. However, both Brad and Maria must agree on who it is and Maria must be present during.
There, that should do it. I’ll have to remember to check up on him later.
What happens next week?
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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
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