Grace Breaks Caitlin Ch. 05

Caitlin was being bounced up and down like a maniac. She felt like her brain and whole skeleton were rattling around inside her. She went up and felt a brief moment of calm, like someone at the top of a roller coaster, before she came crashing down and had her brain fried by the monster dick forcing its way into her at an equally fast speed. For the second time in the past three minutes, she orgasmed, squirting across the room.

Everyone else in the room seemed to be enjoying the show. Many even pulled out their phones to record a girl getting the ass fucking of a lifetime. Caitlin was being absolutely anally demolished and on the verge of losing any brain function she had left.

Not soon enough for her, he came a whole lot inside her. Once he was done, he just let go and Caitlin dropped to the floor, so that she was kneeling with her head touching the ground.

The guy knelt down and spanked her hard enough to shake her whole body before walking away. Caitlin did not feel a thing. She had lost consciousness right after he orgasmed.

When she came to, she noticed that nobody was fucking her. She could tell from the amount of cum on her body having increased that she definitely had been but felt lucky to be out of action at that moment. She soon realized Matt was standing over her, it looked like he had been the one to wake her up.

"C'mon, you've got your big match coming up soon! I'd hate for you to miss it," he said with a smile. He seemed so genuine, so how could he be so cruel? Caitlin wondered this question as she followed him, walking wobbly from the ass fucking and the remains of her drunken state.

"Match?" she asked. Matt ignored her and handed her a skimpy swimsuit that she put on, having lost her shorts and bra at some point in the night. On the bottom was written the same thing that was on her booty shorts. Matt finally led her outside where they had a large inflatable pool with a crowd gathered around it. It looked like a spotlight had been mounted on one of the windows and was shining down on it. Caitlin was worried. She saw Sophia in it and Brenna on the outside. Having some people close to friends nearby helped her calm down a little bit. They were wearing similar swimsuits to hers.

"So, we have a special surprise job for one of you three girls. We won't tell you what it is, but we'll say that the loser is the one who has to do it. You girls are going to oil wrestle to decide. Caitlin, as the one who woke up most recently and our personal favorite," he squeezed her ass at this comment, "you will be the one who fights twice. If you can beat one girl and not the other, the one you beat will be the loser, if you beat both of them, they'll duke it out in a third match and if you lose to both of them, you'll be the loser. Everything's allowed, and the loser is whoever says they give up first, unless we decide otherwise. Making things hot enough could get us more likely to decide to end the match in your favor. On that note, get your sweet ass in there!" he said, shoving Caitlin into the pool.

Caitlin managed to barely stay on her feet as she entered. "We're not actually going to fight for them, right?" Caitlin asked Sophia. "It's pretty degrading."

"It'll be more degrading if I let them do whatever it is they want to me instead of you," Sophia responded. With that, she charged at Caitlin, tackling her and bringing her to the ground. Caitlin was still a bit tipsy and in no condition to fight.

Caitlin pushed Sophia off her. Sophia landed on her hands and knees and quickly picked herself back up before moving over to Caitlin's head. Caitlin was still lying flat on her back, reeling from her fall to the ground. Sophia sat down on Caitlin's face, with Caitlin's whole body sprawled out in front of her. Sophia brought Caitlin's ass up so that she was in a piledriver position. Caitlin tried screaming at her, but it came out muffled between Sophia's buttocks.

"If you want me to get off, you can tap out and surrender the fight at any time," Sophia said. Caitlin instead slaps Sophia's back as much as she can but Sophia powers through it. She moved Caitlin's bikini bottom to the side and jammed her fist into Caitlin's asshole, barely managing to fit it in. Sophia pushed in, inch by inch, letting the blonde savor every second of every painful sensation as she plunged her arm deeper and deeper all the way in until she was wrist deep. Caitlin hadn't been fisted since her first night here and it was almost as unpleasant as she remembered it. Sophia hadn't cut her nails in a while and Caitlin was really feeling it. Sophia scratched at the inside walls of Caitlin's anus. Caitlin tried to move her hips away from Sophia, but she was held in place by Sophia's other arm. Caitlin reached up and managed to grab Sophia's hair. She pulled on it as hard as she could, causing Sophia to panic a little and her whole hand spread out inside of Caitlin. The scratching from that caused Caitlin to immediately let go of Sophia's hair and let out another muffled yell into Sophia's ass.

"Just. Give. Up," Sophia said, flexing her fingers between words. Caitlin tapped out. She couldn't handle anymore of Sophia digging inside her. At the end of the day, she only had to beat one person. She could still beat Brenna, so she was okay with giving up the first fight to Sophia. Sophia carefully pulled her hand out of Caitlin with a pop. Caitlin's waist fell with a splash into the oil and then got up and left.

"Hey, I hope there's no hard feelings between us. I just really did NOT want to lose. I've seen what these guys do to you and just didn't want to be on the receiving end of anything like that," Sophia said, offering her hand to help Caitlin up. Caitlin took it and was brought up. Even though she was upset with the outcome, Caitlin could not blame Sophia.

"Yeah, it's fine," Caitlin said, taking Sophia's hand and getting up. She was sore in more ways than one about losing this match. Caitlin noticed that Sophia was barely covered in oil. Compared to her, Caitlin's back half was completely covered in oil, her ass was shining, and her hair was clearly drenched. It was not until now that she realized how one sided this match actually was. She would have to try a lot harder against Brenna. Brenna was smaller and probably weaker than her but not by enough for Caitlin to be able to win effortlessly. She swore that she wouldn't make the mistake of compassion twice.

"And with that Sophia is cleared of the special task! The loser of the next match will decide who gets to take on the surprise job!" Matt yelled in his best announcer voice. "We will reconvene in half an hour to watch the Brenna vs. Caitlin match!"

Caitlin was fully sober now and dreading the next match. She pulled her bikini bottom back over her butthole and dried herself off as best as she could and considered what her best options would be, but at the end of the day, she didn't know enough about wrestling to actually know what a good option was.

Before long, she heard Matt announcing again, "NOW IT IS TIME FOR THE FINAL SHOWDOWN! CAITLIN VS. BRENNA!" The audience had definitely gotten larger, Caitlin realized as she approached the pool again, Brenna standing on the opposite side. Sophia was watching while getting fucked on the sidelines.

They both stepped into the "ring". Brenna seemed as intent on winning as Caitlin was. As soon as Matt yelled "Begin!" Caitlin charged at Brenna, hoping to make the first move. She knew from her experience with Sophia that it was tough coming back from a disadvantaged state. Luckily, she managed to do exactly what Sophia had done to her and tackled Brenna, sending both girls falling to the ground. Oil covered Brenna's back. Caitlin got on her knees and pinned Brenna down at the shoulders, trying to quickly figure out her next move.

Brenna used her hands to slather herself and Caitlin in as much oil as possible. Once she did that, Caitlin's hands slipped right off of her and, with her support gone, Caitlin fell on top of Brenna. Brenna took advantage of the oil on her body and Caitlin's momentary loss of balance and confusion to slip out from under her.

Brenna and Caitlin both manage to get up at around the same time, Caitlin just a few seconds earlier. Caitlin moves to Brenna and punches her in the gut, knocking the wind out of her. Brenna doubles over but uses that position to grab Caitlin's leg with both hands and pull it up as fast as she can, causing the blonde to lose balance and fall flat on her ass. Brenna pushes herself onto Caitlin and leans in for a kiss. Caitlin is taken aback as their lips lock and her mouth is invaded by Brenna's tongue. She tries to push Brenna off, but her hands keep sliding off her. Eventually, she uses her legs to push her off. Caitlin turns herself around and gets on all fours to pick herself back up.

Brenna stepped on Caitlin, causing her arms to give way and land on her belly again. Brenna's foot slid off. She decided to go with a more stable position and sat down on Caitlin's back. Caitlin tried to wriggle and buck Brenna off. Brenna slid all over Caitlin's back but never actually fell off. Caitlin was slowly realizing that she was not going to win this match either.

Brenna undid the knots on Caitlin's bikini bottom. She slapped the blonde's booty and held the thin cloth in the air as a prize. The crowd went wild, this had been everything they had wanted in a show. However, Caitlin had not surrendered yet. Technically the match was still going, and Brenna knew this. Caitlin came to the conclusion that there was no way whatever she was going to do would be more humiliating than letting this go on.

"I giv-HMFFFFFFF!" she shouted over the cheers. Brenna stuffed Caitlin's bikini bottom into her mouth, cutting Caitlin off at the end. "AH KFFFFFP!" Caitlin yelled out, trying to get her message of surrender out. When she moved to take the cloth out of her mouth, Brenna pushed her face into the shallow oil, not letting her get anything out. Caitlin moved both her hands back as if to say, "OK I won't take the gag out," and Brenna let her come up.

"I don't want to hear you surrender just yet," Brenna said in equal parts to Caitlin and to the audience. Brenna took her own top off, letting her large breasts bounce freely, and wrapped it around Caitlin's neck once like a scarf before taking the two loose ends in her hands like reigns. Luckily, there was enough string on it that she could. "Now, get on all fours and do a lap around this pool. If you do three, we can say this is my win and this will be over for you," Brenna ordered.

Caitlin picked herself up with Brenna still on top of her, like a cowgirl riding a horse. Brenna had to keep her legs locked around Caitlin's belly in order to not slip off, completing the cowgirl image. Caitlin hobbled around the small pool once. Men slapped her butt and some even fired a load onto her and Brenna. Her progress was slow with Brenna on top of her.

Partway through the second lap, someone held something out. It was a paddle with the words "Butt Burner" written on them. Brenna greedily reached out and grabbed it. Without a second thought, she put her arm behind her and brought the paddle down on Caitlin's right cheek, getting a high pitched, muffle yell out of her human horse. Caitlin's butt flared from the strike. The paddle certainly lived up to its name. She stopped for a second, needing to process the pain. Brenna must not have liked that because she used her feet to lightly kick her stomach, while pulling on the bra strings around her throat and yelled, "Hiya Caitlin!"

Caitlin got to moving again. She was slow, but she was moving. Getting one hand forward, then her knee, then the next hand and the second knee. Luckily, she was almost at two laps. All she needed now was a third.

"Alright, Caitlin! We're in the home stretch now! Get going faster, it's the last lap!" Brenna shouted. She brought the paddle down on Caitlin, causing the meaty smack of wood on flesh to be heard over the cheering of the crowd. Brenna was not going to stop until Caitlin finished the lap. Caitlin went as fast as she could on all fours. The faster she was, the sooner it would be over.

However, only a few feet from the end, Caitlin's arms gave out and her front half collapsed. Caitlin was so covered in oil that she slid forward for a few seconds after. Brenna slid down Caitlin's back and ended up just above her neck. Brenna got up and gripped the paddle with two hands before swinging it like a bat at Caitlin's nicely propped up tush, sending a crisp thwack into the night that was probably heard across the whole town followed immediately by an almost as lowed, yet muffled, scream from Caitlin. The force caused Caitlin to slide forward more and drop her now incredibly reddened ass. Brenna dropped the paddle and ignored Caitlin as she basked in the cheers of the crowd.

Caitlin struggled to get up. It took her a long time and she could barely stand once she had. Her legs were shaking horribly, and she stumbled as she approached Brenna. She took the cloth out of her mouth. She knew she should just surrender but after all that Brenna had just put her through, she had to get back at her with something. The fight was lost, she may as well go out swinging, literally. She grabbed the paddle off the ground and tried to put all her remaining strength into one swing on Brenna's shiny little butt.

As soon as it made contact, Brenna let out a yell. Caitlin spanked her again before immediately dropping the paddle. Caitlin got her hits in, now was the time for surrender. "I give up!" she yelled as quickly as possible. Caitlin dropped to her knees, breathing heavily. With that, the match was finally over. There were no immediate cheers since Caitlin landing a hit and giving up immediately was a really strange way to end everything that they had just seen.

"And with that, I guess Caitlin is our loser making her tonight's cum dumpster!" Matt announced to the whole crowd. This got a huge cheer from them. Despite losing, Caitlin was satisfied with the fact that she'd gotten the last hit in.

Brenna, on the other hand, was furious about it. She snapped back to look at Caitlin. Caitlin was incredibly terrified of the look she saw in Brenna's eyes. Brenna quickly approached her. Caitlin could not tell if she was out of strength or paralyzed with fear, but she could not move as she saw Brenna coming toward her.

Brenna put her foot on Caitlin's forehead and pushed her onto her back. She stepped on Caitlin's belly, the pressure forcing itself onto her, keeping her in place. All the satisfaction Caitlin had from spanking Brenna was gone now. Brenna applied some weight to it and all the air in Caitlin left her as her belly was pressed down.

After making her point clear, Brenna removed her foot. She was the only winner of that fight. She extended her arm to help Caitlin up. Caitlin ignored it and Brenna walked away. Sophia came in after her and helped Catlin up.

Three guys came over and took Caitlin away from Sophia. Matt was with them. "We've got to get her all nice and ready for her big job tonight."

"What is it this time?" Caitlin asked, already exhausted.

"I told you, you're a cum dumpster. There are not many other ways to say it," he responded. Caitlin feared the idea that spawned in her.

They took her to the bathroom and had her use it before bending herself over the edge of the bathtub so that her ass was inside the tub and her upper body was outside.

One of the guys took the showerhead down and stuck it in her ass. They had to really push to get it in there but once the first part went in, the whole thing was basically sucked into Caitlin's bottom. Caitlin winced and groaned. With its incredibly wide head, it was clearly not designed to be inside someone, she thought. Caitlin squeaked as cold water immediately flooded Caitlin's intestines. "SHUT IT OFF! SHUT IT OFF!" she yelled. They took it out of her, and a waterfall poured out of her anus.

"Sorry about this, but Matt said we had to do it at least three times," one of them said. Caitlin didn't even have time to say anything before she felt it pressing against her backdoor again, eventually letting itself in all at once. She screamed this time because the water had warmed up and was now hot inside her. She jolted up and moved to take it out of herself, but a different guy held her and her arms down. They let more water flow into her bowels this time to the point that they could see her gut swelling a bit. Caitlin felt bloated, on the verge of bursting as she viewed her continuously expanding tummy. Water once again poured out of Caitlin's butthole when they removed it and her face mirrored this as tears streamed down her face.

They adjusted the temperature before putting it in one last time. Luckily, the temperature was fine this time, but it still hurt like there was no tomorrow. Caitlin wriggled but was kept in place. After only a few seconds, they took it out again and Caitlin forced all the water out of herself.

After that ordeal was over, Caitlin was brought to another room. They had her lay on her back. One guy brought Caitlin's legs down so that her feet were behind her head and then cuffed her ankles together so that she was now stuck in a piledriver position. As if that was not bad enough, they spread her arms out and tied them to two small poles so that she could no longer move them. Another guy got a Sharpie and started writing the word "FEED ME SPERM" on one ass cheek and "CUM DUMPSTER" on the other. Lastly, they put a three-inch-wide, hollow cylinder plug with a funnel on top in her ass.

Matt came in with a horde of people along with Sophia and Brenna. "So, here's how this works," he started in his announcer voice again. Gesturing to Sophia and Brenna, he continued, "these two lovely ladies next to me are going to be your fun for the night! Use them however you like but when you need to blow your load, you have to do it into the funnel leading into our cum dumpster's sweet ass. It's so big, you can't miss it." That got laughter from the room. "Well, that's all I have to say, now get fucking!"

Brenna and Sophia were picked up immediately and guys all around went to town on them. Caitlin could do nothing as she watched the two of them fucked nonstop. She knew the feeling all too well. She watched Sophia getting her hair pulled as she was fucked doggystyle and Brenna getting double penetrated. Caitlin couldn't help but feel that maybe she got off easy after losing the fight. It was not long before the first batch of men were done, and an absurd amount of sperm was deposited into Caitlin's ass. Caitlin felt the warm ooze inside her. It was unpleasant.

This went on all night. Hundreds of guys must have blown their load into the funnel, where it crept down into Caitlin's rectum. A lot of them would spank and thank her after making their generous donation. Many took pictures of Caitlin in her embarrassing position. Caitlin felt like she might just die of embarrassment every time someone she used to know came up. She'd sometimes plead with them to let her go but nobody cared. Omega Nu had made sure to only allow people with a low enough moral bar to attend events like this. They were fully aware Caitlin was not there by choice and would not help her in any way.

Once the last guy had fucked Sophia and then ejaculated into Caitlin, the sex had finally ended. Matt removed the plug from Caitlin's butthole, her asshole still gaped. It seemed like he still had one more idea for the night. "And now, ladies and gentlemen! The final act of the night! The melting snowball! It's our last game and it works a lot like hot potato, but instead of tossing something around, you will be passing some of the cum in Caitlin's ass around. You really didn't think we stored it up for nothing, did you?"