Grace Breaks Caitlin Ch. 04

"Hey, I'll take you up on your offer here," he told her as he grabbed her ass. She felt utterly repulsed by him and the "CUM HERE" message on her behind.

Caitlin had thought about all her options. She couldn't deny any requests but she didn't want to just get used over and over again. Her ass was still in way too much pain for anybody to get funny ideas about using it again anytime soon. She had to change her tactics if she was going to make it through the night. It would have to be something bold.

She'd have to do her best to lead in this situation to prevent him from getting too rough with her. I mean, she had plenty of sexual experience (although most of it was just being forced to lay there take it from someone else) how hard could it be?

She didn't know what she should do so she just had to wing it. She grabbed his crotch, it wasn't fully hard yet but it was already a little bigger than she'd wanted. She felt it twitch when she grabbed it and hid her disgust. In her best seductive voice, she whispered, "You wanna get up in me that bad? We can go somewhere private and I'll give you your chance. But I better be impressed, or else I'll have to punish you." She had no idea what she should do from here and was hoping he wouldn't see through her bluff. He was tough to read.

"Let's go, big guy," she whispered before squeezing him and letting go before leading the way into a bedroom. He shrugged and followed her, clearly not really minding her lead. He watched her ass bounce as she walked. She hoped he was mesmerized by it so he wouldn't notice she was still struggling a little with walking properly after the fisting she took.

The room was dirty. Things were scattered all over the floor and there was a queen size bed in the middle, covered in unknown stains. As soon as they entered, she knew she had to set the tone so she grabbed him by his shirt and pushed him against the wall. She quickly undid his belt and jeans and pulled his dick out, holding it in one hand, still semi-erect.

"Aw, what happened? Did I not excite you enough?" she asked, "Did you maybe spend too much energy on another girl today?" With this, she knelt down and put his dick in her mouth briefly before popping it back out.

"Oh yeah, that definitely tastes like another girl," she said, looking up at him. "I can't have you pleasing other girls and leaving me unsatisfied," she said in a bit of a condescending tone. She was relieved, so far, he didn't seem to mind her act. Caitlin got back on her feet and pushed him on his back onto the bed.

She started stroking him lightly, then a bit faster. She was gentle but moved fast. She felt him start to grow in her hand. Seeing him eventually reach his full length, struck a little fear into her heart. He was pretty big and she was hoping for something that she could just handle for a bit, without worry. When she finally ripped her gaze from his member and looked back at his face, she saw that he was starting to look like he might be annoyed. She couldn't tell really well, but didn't want to blow her chances at being the one in control so she figured she'd cut to the chase and put a condom on him.

She crawled over him and gave him a quick kiss before pulling the front of her shorts to the side and positioning herself above his penis. She inserted it slowly and felt it grow one more time inside her. "There we go, big guy. Now you're really excited, I can tell. Time for our fun to begin," she moaned. As quickly as she could, she let herself fall onto him, twitching a bit as she did, hoping he didn't notice that. "I hope that wasn't too much for you," she moaned as she rose up again. "Look at all that was in me. You're gonna do great."

Caitlin rode him as best as she could. It was a little awkward when she tried picking up the pace, but she soon found her rhythm. She was bouncing on top of him while looking at him passionately with her best cute smile. It hurt her but she knew it'd hurt a hell of a lot more if she relinquished control. At least she could control the pace here.

He was watching her pelvis as she moved up and down like a boat on the ocean, gradually getting faster. His penis repeatedly being pulled out to the head and then the feeling of the 2 of them combining at the waist. This continued until she felt his dick pulsing inside her, followed by his ejaculation, at which point she brought herself up and out of him and leaned over so she was right over him with her hands on either side of his head, propping her up. He looked up at her with a smirk, his eyes clearly still hungry for more.

"So, did you enjoy that?" she asked, biting her lower lip. She hated what she'd become.

He kissed her before responding. "Y'know what? I did, but I won't lie, I've had better. Don't worry though, I know how to get you to reach your full potential," he said. She got really scared for a second before he pulled her down on top of him in an embrace.

"You really think I'm going to buy your whole teasing dom routine? Please, you're wearing shorts that have 'Fuck me like you own me' written in all caps on the front," he whispered sharply in her ear, pulling her tighter to him. Her heart was racing and she knew he could definitely feel it. "Plus, you're clearly an amateur at taking the lead. Don't get me wrong, you're a SMOKING hot babe, but you have no idea what you're doing so just know your place and take it like the bitch you are instead of... whatever it is you just tried. An ass like yours just needs to lay there and you'll be great," he said. She felt his dick rising once more under her and her panic fully set in. "Let me show you what it means for me to fuck you like I own you. I'm gonna ruin you and give you what you deserve: The cum in your ass that you're begging for," he finished, rolling over so that he was now on top of her and flipped her onto her stomach.

She was a bit petrified, reeling from the failure of her plan, as he flipped her over and jerked her shorts down so they were now around her ankles. He pulled her ass up into the air and pulled his pants down and flung them across the room, but not before taking his belt out of them and laying it on the bed. He took the condom off and squeezed its contents out onto her back.

He gripped her behind, getting a feel for it. "You've got a lot of MEAT back here," he told her. He whistled as he spread her buttocks and saw her back door. It had recovered some in the time since her fisting but was still already clearly used. "With a nice bum like yours, it's no surprise you're a buttslut. I don't care if you've seen some use, I'll still enjoy you."

He plunged into her and fit in fairly easily. This got a grunt from her. "I don't even need lube or anything!" he exclaimed with joy.

"See, I think I know your angle," he continued as he kept thrusting. Curious, she looked back at him. "You probably like being fucked real rough, and you know that condescending act will get people all fed up with you and that way, they handle you more roughly, but you still wear those little shorts of yours so that they see through you, know you don't actually want to be in the lead and eventually take over for you. It's kinda smart, honestly. It worked on me, I definitely want to fuck you WAY harder than I did before. So let me give you what you've REALLY wanted all this time. I know I'm right, but I want to hear it from you. I mean, you could stay silent and I'll punish you more, but something tells me you won't see it as punishment."

He grabbed his belt after pulling out, folded it in half and took a step back. She couldn't explain her real situation without saying she was forced, which was against their deal with Mark, so she stayed quiet. "Oh well, time to do what your dad should've done to a degenerate girl like you," he muttered.

He belted her across the right side of her rear, getting a shriek from Caitlin. Her butt rippled and her ass fell back on the bed. She yelled out, "OKAY! OKAY! You're right! I really just wanted to be fucked REALLY hard! My whole act was fake and I just wanted you to treat me like a dumb slutty bitch, the whole time!" She couldn't believe what she'd just said, but she had to go along with him, otherwise who knows what he'd do?

"Okay then, time to give you the treatment you wanted," he said, chuckling as he rained his belt down in a flurry upon her poor behind. She yelled out in pain. Caitlin immediately regretted her decision, she'd spared herself neither the humiliation of her lie nor the pain inflicted by the sadist behind her. Once her ass had turned a bright red, he stopped.

Her butt was on FIRE. The stinging of his belt lingered on her soft flesh as she looked back, worried about what else he might do to her next.

He put the belt through the buckle so that it formed a small loop and put that loop around her neck like a leash. She moved her hands to take it off but all he had to do was pull tightly until she stopped. He entered her asshole again as deep as he could and pulled back on her "leash", just enough to let her know he still had it around her neck and wasn't going to let go anytime soon.

Caitlin was getting completely RAILED by him. It felt as if he was trying to leave a permanent imprint on the bed. Her ass still felt so raw that contact with anything hurt so every time he buried himself in her, she'd wince from him pressing into her, both inside and on the outside.

"Tell me I own you and how much you want me to fuck you hard and then BEG me to cum deep in your ass," he commanded.

Caitlin had learned from last time and opted to stay silent. After a few seconds, she realized that she made the wrong choice. He spanked her with his full force as he pulled tight on the leash with his other hand. "Y-You o-own me..." she muttered. It was hard getting words out with her body being repeatedly slammed into the bed and choked at the same time. Another spank.

"Louder! Clearer too! And let those moans out too! I know I'm doing great back here, and I wanna hear it! BE shameless. And y'know what? Just for fun, add a 'daddy' or two in there, 'cause why not?" he said with a grin, revelling in her humiliation.

Caitlin stored up all the energy she could muster in this situation and let out a breathy yell, "I am daddy's little fucktoy bitch! Please fuck me harder! I want daddy to absolutely DESTROY my pretty little asshole!"

She had to stop for a minute because he did start fucking her faster and harder. Despite her sheer embarrassment, she had to sell the lie, so she exaggerated it to hell.

"All I want is for you to fill my cute booty with your precious CUM and treat me like a cheap wh-!" She got cut off by the pull of her leash, choking her once again. Her vision got blurry, but she came hard, spraying all over the bed. The pull of the leash also caused her back to arch for a few seconds before it gave slack when he came. She felt rope after rope of warm, gooey semen being shot inside her butt. After that, he lay down on top of her, with his arms around her and his hands under her belly. His shaft was still inside her ass, like a cork, keeping his wasted seed inside her. He seemed to be enjoying the peace and she was just glad for there to be a minute to rest.

They were both breathing heavily. Caitlin lay under him, hoping it was over. Maybe when he leaves, she could hide here for the rest of the party. A feeling in her gut (the one that wasn't a warm and sticky ooze) told her it seemed unlikely to work.

After a few minutes, she saw the door open and tried to get out from under him but he didn't budge. Much to Caitlin's surprise, it was Sophia who entered the room and, naturally, she was with another man. Caitlin went back to laying limp but the man on top of her got up.

"Hey Matt," he said to the guy who just walked in.

"Hey Chris," he responded. Caitlin could see him staring at her, now noticing her abused, red ass and the belt around her neck. He smiled, imagining what must have just occurred.

"I just finished up with this slut," Matt said, spanking Caitlin. "She likes being treated like a little piggy, ain't that right?" he said, pulling a little on the leash to bring her head back.

"Yes," she said without thinking, just to get him to stop. He let go again and this time, took the belt off her neck.

Turning to Chris, Matt continued, "Anyway, I was just leaving, so you can use this room if you want. C'mon, blondie. Scram so they can screw here."

Caitlin slowly dragged herself off the bed and put her booty shorts on once again before walking out. Walking was putting it generously, the night was taking its toll on her already as she stumbled out of the room. It didn't take too long before she could hear Sophia moaning loudly in the same room she'd just left.

She hadn't even made it downstairs when she found Mark who seemed really excited to see her.

"Hey! Just the girl I was looking for. I was afraid that I'd have to use Brenna or something for this if I didn't find you. We've got your new job all set up now and I think it'll really make all our guests happy."

"What is it?" she asked, clearly already tired and reluctant.

"Just follow me. Trust me, they're gonna love you."

Caitlin followed him down the stairs and outside into the backyard. There, she saw a small stage and a crowd of people in front of it, drinking and talking, but clearly waiting for something. Due to the fence around the back yard, they looked a little cramped but didn't seem to mind it.

"Now, they're expecting a show and, as I'm sure you guessed, that's where you come in. Here's a song and dance that I want you to learn, then you're just gonna go up there and perform it. Don't worry, it's all pretty simple. Then, when they shout for an encore, I want you to perform it again, OK? Perfect," he said, handing her a sheet of paper. "Now go back inside for about 15 minutes to memorize that and come back out, we'll keep 'em warm for you."

15 minutes later, Caitlin came out onto the stage. She was a bit of a wreck but tried to hide it, with limited success. She made it to centerstage and the crowd went silent for a second before erupting into catcalls and hollers. What got to her though, was when someone yelled, "Hey look, it's Caitlin! I always thought she was hot, glad to know she's a SLUT!" Multiple others seemed to recognize her as well but the crowd's yells turned to murmurs before dying down so the show could start.

"I'm a little cumslut, short and plump," she sang to the tune of "I'm a Little Teapot" while grabbing her ass and showing it off to the crowd. Her voice was shaking but they didn't seem to mind. She faced the audience and moved her hands up in order to push her boobs together. "Here are my titties, here is my rump," she slapped her ass while once again showing it off to the audience. She noticed a few people in the audience had even started masturbating. "When you're feeling horny, plow my butt!" she sang, trying to be cheery while doing a thrusting motion with her arms and hips. Finally, she leaned over and sang, "Just bend me over and knock me up!" before coming back up and rubbing her belly.

The audience loved it and, as Mark had predicted, wanted an encore. This time there was a tall, nude, well hung man approaching her on stage. He stopped when he was directly behind her. He undid her top and just ripped off her shorts. She moved to cover herself and looked at Mark and he yelled, "Don't get stage fright now! Just do it again!"

She swallowed and began again, "I'm a little cumslut, short and plump." Her voice was shaking more than ever. "Here are my titties," she continued, smushing her breasts together before moving them down to her butt, "here is my rump."

"When you're feeling horny, come plOW-" she stopped because the guy who was behind her had moved towards her and rammed his cock in her vagina. This wasn't part of what Mark had told her. Her whole brain shut down for a second as this happened and she couldn't find the will to continue but a second thrust brought her back to her senses. She took a deep breath and started from the top of the line, "When you're feeling horny, PLOW. MY. BUTT," she had trouble getting it out because he thrusted with his full weight on each of the last 3 words.

"Just bend me ov-YA," she yelped as his hand moved to her head and pushed so she was bent over and then started fucking her wildly, "and KNOoooOoCK MmmEeeEE uuUUP," she managed to finish, her voice bouncing as if she were sitting on a washer machine.

As if on command, he creampied her within seconds of the last line before dropping her and letting her fall to the ground. The crowd erupted in cheers. She felt like she was in a daze as she got back up. The whole show was a lot on her mind, especially after everything before, and it seemed like there was still more to come.

Mark came out on stage next to Caitlin. The other man had backed up and left. "Ladies and gentlemen, the best part of Caitlin's performance hasn't even happened yet. Watch as she tries to crawl back into the house, headfirst, through this hole." Caitlin looked at the house and, sure enough, there was a circular hole in the wall. It looked like it had some kind of cushion around it.

The hole wasn't tremendously big and she thought that her hips would be a tight squeeze but could probably get through. She knew there was something else to this, but there was only one way to find out what.

Slowly, she put her arms through and stuck her head in. She couldn't see anything strange on the other side. Deciding to continue through before something new came up, she moved forward but found that her hips were too wide to fit, as she'd predicted. She made it to her waist and tried to get her hips through but couldn't. She was about to pull herself out when the hole started closing.

She couldn't believe it, the cushions were inflating until eventually, they pinched her slim waist, trapping her in the wall...with her ass sticking outside...and a whole crowd of people. Great. Now it seemed REALLY obvious where this was headed. Another frat boy came up to her, "sorry about this, but you're our fundraiser".

She could still hear outside though. Mark was announcing to the whole crowd again.

"Come on up and cum in her! This is the interactive part of the show where, for the low price of $1 each, all of YOU get to try out sweet ol' Caitlin here. You have your choice of using her bottom half out here or going inside and using her pretty little face! And remember everyone, be as rough as you want! Get in line soon, because she is now open for business!" he said, slapping her ass and walking away.

Within a minute of the announcement's end, someone she couldn't even see was already balls deep in her vagina. She pushed on the walls with her hands in a futile effort to get farther but she was pretty darn stuck.

She did have some mobility, though, but as soon as the whole hit either her hips or shoulders was where that limited freedom ended. Even moving that much took a little effort. Not that it mattered in this case, the guy behind her was pressing her back half as much into the wall as he could. She almost thought it was going to break, not that luck would ever shine on her like that. Not that it would matter either, they'd probably fuck her brainless even if the house were burning down around them.

When he finished, the guy pulled her as far out as he could and came on her back. It didn't take long for the next guy to come in and take his place. After a few more guys, people started showing up at the front.

The first one that did was hard as a rock and she had forgotten the horrible smell of an unwashed penis right below her nose...until now. She'd only ever taken dick on the day that Grace broke her in, aside from that it had all been toys. The real thing was a lot worse than she'd remembered.