Grace Breaks Caitlin Ch. 05

A look of disgust passed across the faces of all three girls. Matt proceeded to explain the rules, "Now, it'll start with Brenna here taking a large sip out of Caitlin's fat ass. We estimate that there's about half a gallon in there, so don't be shy. I want to see you take in as much as you can. Then Sophia will take one as well and you will pass the two around. There will be a rotation, Brenna passes to Sophia, Sophia to Caitlin and Caitlin to Brenna. I will have a timer going and when that timer goes off, the bitch without cum in their mouth gets a prize, the other two will have to swallow! Swallowing or spitting before the timer goes off is against the rules, whoever does it is immediately disqualified. Now GO!"

Brenna hesitantly approached Caitlin. Caitlin's ass, despite the removal of the funnel was now just gaping from the hours it had been spread open. Brenna could see the cum inside, and decided it was best to just get it over with. She put her mouth to the hole and tipped Caitlin's butt back a little, getting it out little by little. Caitlin did not like the feeling of Brenna slurping cum out of her rectum. While it was nice to get some of it out, the feeling of suction at the rim of her butthole felt disgusting. When Brenna finally stopped and got up, Caitlin saw her cheeks were full, like a squirrel's.

Next came Sophia, her approach was way different from Brenna's. Unlike Brenna's slow and steady method, Sophia undid the knots at Caitlin's arms and asked Matt to undo the cuffs around her ankles. Curious to see what Sophia had planned, Matt did just that. Sophia knelt in front of Caitlin, put her arms around Caitlin's still upside-down waist and fell backward so that Caitlin landed on top of her. Cum spilled out of her like a kind of slow fountain and Sophia got as much as she could in her mouth, also getting a lot on her face but at the end of it, she rolled Caitlin off of her so that she was belly down on the ground. Caitlin hated being tossed around but she had to admit it was a lot better than Brenna's process.

While she was still lying belly down, Matt shoved a very wide butt plug into her again. "We just think it would be more fun if you do this full of cum. Timer starts now!" he said with a grin.

"Bastard," Caitlin muttered under her breath.

Before she could give Matt a good piece of her mind, Sophia rolled her over and kept her pinned to the ground. She leaned in, kissed Caitlin and let the sperm fall in. Caitlin's cheeks swelled up in order to contain the full load as the bitterness pierced her taste buds. She got back up and Brenna immediately approached Sophia, eager to get the warm semen out of her mouth. Caitlin picked herself up as the two of them had their exchange.

Now she noticed that it was her turn to pass it. She was pretty scared of approaching Brenna but knew that she had to. If there was one person she wanted to lose, it was her. Caitlin pulled the shorter girl close to her, grabbed the back of her head, leaned down and kissed her. Caitlin shoveled the sperm into Brenna's mouth using her tongue.

As soon as their lips let go of each other, Caitlin was spun around and met with Sophia behind her. Sophia took a page out of Caitlin's book and grabbed Caitlin by the waist and dipped her as if they were dancing. She parted Caitlin's lips as soon as they touched her own and spit the sperm into her mouth, filling it up again.

Caitlin accepted it fully and as soon as Sophia had deposited the full load, she lifted Caitlin back up and left her standing there, feeling really confused. She witnessed Sophia willingly accept Brenna like it was no big deal.

Then it was her turn again, so she approached Brenna. However, Caitlin was unaware of the fact that Brenna had a small tactic she wanted to try out. She was going to try to get Caitlin to swallow or spit out her own load. She put her arms around Caitlin and moved to spank her but was a little late. Caitlin was a lot faster with her kiss this time, so when Brenna's spank landed, Caitlin was caught off guard and spit the sperm directly into Brenna's mouth so suddenly that Brenna accidentally swallowed most of it. Brenna immediately pushed Caitlin off her and started coughing and spitting up whatever she could get out.

Brenna was angry that her plan backfired and wanted to take it out on Caitlin but was not given the time to. Sophia took her away before Brenna could do anything. Sophia pinned Caitlin to a wall and filled her mouth with spunk. Caitlin was just happy that Brenna was eliminated, but now she had a chance at victory and had to take it.

Once Sophia had finished, Caitlin put her arms around her and kicked off the wall, sending the two girls to the floor, with Caitlin landing on top of Sophia. Caitlin moved down and kissed Sophia while pinning her to the ground, like she had done earlier, this time grabbing the back of her head with her other hand. Like before, the sperm fell easily into Sophia's mouth.

Sophia did the same, causing worry in Caitlin. Sophia then rolled them both over so that she was on top and gave the cum right back to her without disconnecting their lips. Caitlin was not giving in yet.

She pushed off too and the girls were rolling around on the floor. The whole room watched, mesmerized by the two naked babes making out passionately and rolling around on the floor. Some placed bets while others just cheered on their favorite, the room seemed to be split pretty evenly. Their tongues were fighting a fierce and intense battle with each other as they continuously gave the other a healthy dose of several strangers' seed, never letting the other go to even take a breath.

The two were so invested in their one-on-one battle that they barely heard it when the alarm went off. When it did, the whole room was silent as the two girls stopped dead where they were.

Caitlin was on top of Sophia with no sperm in her mouth. Caitlin jumped up, cheering for herself at the top of her lungs. Sophia swallowed the snowball right there.

"Caitlin won the grand prize folks! She gets two free weeks off where no member of the frat or party guest can fuck her!" Matt announced. Caitlin's jaw dropped when she heard that. Her own cheering only grew louder at the news. It was a better prize than she ever thought Matt would give any of them, much less the girl who was apparently the fan favorite. After she was done with her short celebration, Caitlin helped Sophia up, who seemed to be frozen with shock on the floor after the insane night that had just happened to all of them.

Brenna was not at all happy with the outcome. Luckily for her, it seemed that some of the guys had noticed her frustrations and wanted to help her get them out, to put it lightly. That night, under her pillow she had found a strap on and the same paddle from earlier. There was a note that read "For breaking in the steed. Matt only said that guests and members couldn't use her. Go to town."

She did not know who placed them there but boy, oh boy was she grateful. That night, Caitlin slept in the dog bed. She no longer trusted Brenna to sleep next to her after the way she had treated her at the wrestling event.

Later, when Caitlin was fast asleep, Brenna took the strap on out from under her pillow and put it on. She moved over to the dog bed and gently pulled Caitlin's shorts to the side so as not to wake her. She was greeted with the sight of Caitlin's still somewhat gaping asshole. Brenna wondered if she'd ever recover.

Seeing it now that she did not have to worry about herself turned her on more than she thought. The slightly faded, degrading writing leftover on her left cheek also got her increasingly wet.

Brenna did not know how she would get away with this or deal with Caitlin afterwards but that was not important now. Now she just wanted to put Caitlin back in her place. She had humiliated her today and to Brenna, that was unforgivable.

Brenna pushed her hips forward, watching as the dildo disappeared into Caitlin's asshole. She heard it make a squelch as she reached the end and hit the cum from earlier in the night that was still buried deep in her. Caitlin stirred under her but was too out cold for this to fully wake her up. Brenna wanted her awake. She pulled out almost all the way and brought the paddle down on her ass. Caitlin's eyes shot open. She looked behind her and saw Brenna inside her.

"Get the fuck off me!" she yelled. Brenna brought the paddle down again.

"No! You may be safe from all of them, but for everything they do to me in these next weeks, I will repay it to you tenfold," Brenna responded.

Caitlin tried to move away but Brenna leaned in, reaching deeper and keeping her in place. The strap on's tip was glossy with the semen that it kept shoving deeper and deeper into the blonde's sorry and sore rectum. Brenna ramped up the pace, bouncing off of Caitlin's butt and watching it jiggle beautifully. Moans that sounded like music to Brenna's ears escaped Caitlin's mouth. Brenna could not explain it, she was straight but there was just something about Caitlin that made her feel the need to dominate her completely.

Caitlin had nearly forgotten about the world of strap ons after all this time in the frat. There was no warmth behind it, just cold plastic. It reminded her of her time with Grace, which after all that had happened to her here, seemed heavenly by comparison. Sure, there were the all night fuckings and borderline torture, but it's not like that was not something she experienced here. At the end of the day, Grace was rough, but she was only one person (except for when Zoe got involved) and all her humiliation was in private, and she was still able to have a normal life whenever it did not conflict with Grace's schedule for her.

Eventually, Caitlin came to an orgasm. Brenna noticed the blonde's relaxation and realized why but decided to continue wreaking havoc on the blonde's bruised bottom. It was not until Brenna's physical stamina was exhausted that she stopped her attack on the blonde's bruised bottom. Caitlin would certainly not be walking any time soon. Happy with what she had accomplished that night, she left the big bootied blonde alone so she could get some sleep.

For days later, Caitlin would be shitting out cum left over from her time as the cum dumpster. It didn't help that Brenna was pushing it in deeper almost every night. She spent her time during the day reading or watching TV in the basement when she was not cooking or cleaning. Luckily, they were kind enough to provide some entertainment for the girls. It seemed like they really did not care over all as long as they got to fuck them.

Night was much less peaceful. Caitlin did her best to sleep with one eye open and even started sleeping with Sophia in her bed whenever she was available just for extra protection. However, she noticed that Sophia was in high demand at night. Caitlin wondered if maybe that was on purpose because they knew Brenna violated her at night and they just wanted that to happen. Any night that Sophia was not around, Caitlin would wake up partway through the night with Brenna on top of her and a dildo deep in one of her holes.

One night, Caitlin thought she would plan a counterattack. She took the dildo to use on Brenna that night. However, when Brenna realized it, she immediately got into a fight with Caitlin. It was close but Brenna ended up winning. She was merciless in her violation of Caitlin that night.

Caitlin suffered as Brenna fucked her missionary style, ripping in and out of her pussy. She was overflowing with energy after their fight and there was no better way to spend it than hate sex. She had a lot of fun pounding and choking Caitlin for hours that night.

After that, Caitlin just hid the paddle and dildo and Brenna never found them. They had a fight, but it seemed like that was enough to get Brenna to stop fucking her. Brenna would still do her best to make Caitlin suffer by fisting, spanking or choking her.

At the end of her two

weeks, Caitlin was called up to meet with all the frat members. She walked into the room and was greeted with the image of all the frat boys waiting for her there.

At the center of the whole scene was Grace in a skirt and white button up with her breasts practically bulging out of them. Caitlin noticed the rope in her right hand.

"After five months, I'm finally here to buy you back, blondie," she said excitedly. Caitlin thought she would prefer Grace but now that she was face to face with her, she was not sure anymore. "But first, everyone wants to give you a proper send off!"

She moved up to Caitlin and pushed down on her shoulders so that Caitlin was forced down on her knees. The guys all crowded around her and started jerking off. Grace held Caitlin's face in her hand to keep her facing all the boys. One by one they all shot a warm load across her face and chest as their goodbye present to her. It got all in her hair, in her eyes and all over her front. After a while, the last one of them ejaculated.

"Now say thank you to all of them for being so kind to you during your stay," Grace said. Caitlin did not want to even try to resist here.

"Thank you for your great treatment," she mumbled.

"Now, let's just make you easy to carry," Grace said. She seemed really happy to be back as she pushed Caitlin onto her stomach and surprisingly quickly had her hogtied. Grace picked Caitlin up and put her over her shoulder before carrying her out to her truck, saying goodbye and giving small pecks on the cheek to some of the boys on her way out and letting them grope or spank Caitlin one more time. Isaac gave her a particularly heavy smack across the ass.

"I have something very special that I think you are going to love," she said as she put Caitlin down in the back seat, which was covered in plastic wrap so as not to get any semen anywhere.

Grace looked back at her after she got in the driver's seat. Caitlin was finally back in her clutches.

Author's Notes: THE NEXT CHAPTER IS GOING TO BE WHAT I ORIGINALLY INTENDED TO BE THE FINALE. (I have a few ideas for side stories, including a chapter dedicated to Grace's night at Omega Nu, an alternate timeline where Grace never regains control after chapter 3 and maybe just a few short, isolated Grace and Caitlin stories, if I come up with ideas down the line.) IF I DECIDE TO CONTINUE THEIR STORY AFTER THE FINALE, IT WILL BE VERY DIFFERENT. SO, EITHER COMMENT/SEND ME AN IDEA OR TWO FOR A NEW STORY WITH THEM OR LOOK FORWARD TO WHAT COULD BE THE FINALE! EITHER WAY, I HOPE YOU ENJOY IT!

ALSO, A VERY SPECIAL THANKS TO Psylent21 FOR EDITING AND HELPING ME BRAINSTORM IDEAS! (The cum dumpster/snowballing scene was completely their idea, and the story would not be complete without it, so I am super grateful.) I AM ALWAYS LOOKING TO INCLUDE READER IDEAS INTO MY STORIES SO SEND THEM IN IF YOU HAVE ANY!

THIS IS (once again) MY LONGEST STORY TO DATE, PASSING THE PREVIOUS CHAPTER BY A LOT! IT TOOK A VERY LONG TIME TO WRITE! I WOULD REALLY APPRECIATE ANY COMMENTS AND FEEDBACK FROM YOU ALL. IT'S A LARGE PART OF WHAT MOTIVATES ME TO WRITE AND I LOVE HEARING YOUR THOUGHTS!