Chapter 25
by
psanko
Does Josh accept the bet?
Of course he does!
Josh was still fucking Tiana up her ass while he held her, so speaking was hard for her to do but still she tried.
“You’re not gonnnnaahhh… say yesssss… are you Joooshhhh?” Tiana asked naively.
“I thought you said you were just as good as her, Tiana? If that is true this, you should be okay with proving yourself? Or are you taking that back?” Josh said, trying to turn Tiana’s own words against her.
“I… oh… uh… okay fine! But Mike can’t fuck me up my ass. It belongs to Josh and that’s final!” Tiana was very stern in her voice.
“Sure, whatever... Mike, you and Tiana can start off together, since Josh and Tiana have already fucked each other. I’ll fuck Josh meanwhile” Caitlyn said. Josh dismounted Tiana from his cock, while Mike and Caitlyn took off their clothes. Josh looked at his new partner’s body. Finally, he could see her body more closely, looking at her giants breasts through her shirt would make any man want more.
Caitlyn, to Josh’s surprise, had pierced nipples and a tattoo made of flowers across her stomach, which only excited him more. Despite having had sex with Tiana for about an hour, cumming multiple times, his dick was still rock hard and ready to go again as if he hadn’t just ass-fucked Tiana. Josh also made a quick glance at Mike. Josh was happy when he noticed that Mike’s dick was about an inch shorter than his own.
Caitlyn took Josh hand, said “Come with me” and lead him to her room.
Josh was now in Caitlyn’s room with her. His hormones were raging. One of the sexiest women he had ever seen stood right in front of him completely naked and he had a raging erection he just couldn’t kill. He was just about to reach out and grab her head like he had done to Tiana after she had led him to her room, but Caitlyn immediately went to her knees and grabbed Josh’s cock by its base with both hands and started rubbing it. It immediately felt good.
“Let me show you how a real woman pleases a man.” She said and placed how lips on the head of his cock and swallowed it whole. Immediately Josh mind began to flash with images. “A bit later than usual?” he thought. Normally the images would start immediately after he made skin contact but apparently this time that didn’t happen.
The images showed him all kinds of things about Caitlyn. Most of them were pretty standard, like bathing in a bathtub full of cum, having incestuous sex with her own mother and such. Two, however, stood out to Josh.
In the first Caitlyn was in a scissoring position with Tiana with long and thick dildos going from Caitlyn’s ass, pussy and mouth to Tiana’s own holes. Despite deep-throating dildo’s longer than Josh’s dick Caitlyn’s and Tiana’s lips still managed to meet in the middle.
And in the second one he saw Caitlyn bound and locked up by her extremities so that she couldn’t move any of them. Her legs were wide apart and thanks to the locks she couldn’t close them. Behind her were a long line of men all different from each other. The line seemed to be never ending, reaching onwards forever. Each man would have his turn at her body and could use her in whichever way they wanted to, and Caitlyn would take it all like the slut she was.
“Caitlyn has a thing for Tiana? And she wants to have sex with every man in the world? How could she ever fulfil that one?” he wondered inside his head.
Caitlyn took his cockhead out of her mouth and asked, “Done flashing?”
“Um… excuse me?” Josh said, confused by her question.
“You know the thing you guys do when you touch a woman?”
“Um yeah… I am” Josh was kind of surprised. He didn’t realize that of course women would know about men’s ability to know their fetishes by touching their skin.
“Don’t fucking tell Tiana or I’ll make your life more miserable than you can imagine.” Caitlyn said with a stern and serious voice.
“Okay, I won’t” replied Josh. To some degree he thought of her threat as empty. “What was she gonna do? Withhold sex from me? As if any woman in this world could… HAH!” he thought.
“Good, now it’s time for you to see what I can do” Caitlyn said and put her hands behind Josh’s butt and then proceeded to push his cock inside her mouth and down her throat and didn’t stop until her nose touched his stomach. Josh was cumming all the way down her throat with a continuous stream of cum.
“Arrgh! that feels sooo good...!” Josh moaned loudly.
Caitlyn then proceeded to move her backwards and forwards while placing her tongue in strategic places so as to increase the stimuli Josh was feeling. It felt so much better than the rough skull fucking Josh had done in Tiana he thought. His cockhead went up and down her throat and was thoroughly lubricated by the mix juices of his cum and Caitlyn’s spit.
All the cum was steadily flowing down through her throat and into her stomach. She had done this so many times before she could practically do it in her sleep.
In Caitlyn’s head she cycled through the most important parts of deepthroating her mother had told her, when she reached puberty.
“Make sure your teeth don’t touch the skin.”
“Suppress your gag reflex by relaxing your throat and concentrating on the delicious taste of his cum, cock and balls.”
“Only use your head to stimulate his cock, don’t have him move it himself. It makes it easier for you to plan your breathing and caress his cock with your tongue.”
“Listen for his moans, the higher they are the more pleasure he feels.”
Josh was in heaven. Caitlyn was amazing, and she was only using her mouth to please him! He had fucked 3 women today after Heather’s changes and every time even when he was having sex, he could only think of having more sex, but not with Caitlyn. He could only concentrate on how good this felt and nothing else.
10 minutes passed, and Caitlyn withdrew Josh’s cock from her throat. Josh already felt really good and to some degree satisfied but he sure as hell wasn’t gonna stop here.
Caitlyn stood up and said, “Lay down on the bed with your back against it.”
Josh did as she said and laid down. His dick stood straight up into the air with cum still oozing from the head. Caitlyn placed her hand on the shaft of his dick, grabed it tightly and then moved along his dick ensuring her hand was covered in as much of Josh’s cum as possible.
“I have to lube it up first.” Caitlyn said and lubed up her asshole with Josh’s cum. Josh was spectating her from the bed, eyeing her gorgeous ass in particular. He couldn’t believe his luck. First, he had fucked Tiana who was on her own already a good catch and then he got to fuck her roommate? What are the chances? Even in this sex-manic world?
Caitlyn finished lubing up her asshole, went onto the bed, placed her ass on Josh crotch with her back against him, grabbed his dick placed it against her entrance and plumbed down her ass in one swift motion. The feeling it created made Josh yell out in pleasure “Argh! So, goddam tight!” Despite Josh’s cock’s enormous size and it being hard as rock, he could feel it shrink in size inside her by just a little. “How could any woman be this goddam tight?” He wondered.
“That’s what you all say. Now don’t you move babe! Let me do the work.” Caitlyn said and the proceeded to ride Josh’s cock reverse cowgirl style. Her butt went up and down as she bounced on his cock, she moaned and screamed loudly, as Josh simply laid with his back on the bed and he watched it all. If the throat-job felt like heaven, then this was the step above that if such a place was even possible.
Caitlyn was simply amazing.
Despite the ecstasy Caitlyn was causing to Josh's mind, Josh could help but go through other mindblowing sex-positions they could do later that night.
“Taking her from behind is the most obvious next move! But I could grab her and pound into her with her back against the wall! Just smashing away at her pussy! So many possibilities… good thing that I have all the time in the world.”
While Josh is enjoying himself how is Heather doing?
Changing the Rules
A phone that can change the world
The world is run on rules and taboos. What happens if you change a few of them?
Updated on Mar 22, 2026
by street0
Created on Sep 24, 2010
by street0
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