Babysitter

Note: James is a developmentally stunted 18 year old that needs adult supervision because he’s tarded, yeah. That’s why he has a babysitter, just roll with it.

“Wow, what happened to you tough guy?” Claire said, tussling James’ hair as he opened the door to greet her.

He batted her hand away playfully. “Nothing. Just some school stuff.”

Claire bent down to eye level with James to look over the black eye he had. “Looks painful. Does it hurt?” she asked, prodding his eye.

“Ow! Yes! It does, so don’t poke me,” James yelped.

“Ethan again?”

James nodded.

“Well, at least tell me you put up a fight.”

“Course I did. But he’s like twice my size. I don’t even know if that troll felt it or if he’s too stupid to know what pain is.”

Claire nodded sympathetically. “Well, I know what’ll cheer you up. Let’s go inside and you can dump one in my butt.” Claire led James into the living room where she pulled down her denim shorts and bent over the arm of the couch.

“Thanks Claire, you’re the best,” James said.

“Don’t mention it champ.”

James quickly took off his shorts and shoved himself inside his babysitter where he began happily pumping away. As he settled into her asshole, he hugged himself into her, reaching around and grabbing handfuls of her tits fondly. The two chatted and talked about their day as James sodomized his babysitter.

“Claire? Can I gape you today?”

“That depends. What’d you get on your English test today?”

“A-“

“Good job champ. Well in that case, sure, let’s say 15 minutes of gaping.”

“Just 15?”

Claire tutted. “Since when’d you get so greedy. Yes just 15. Listen champ, if you want more, you better show me an A or A+.”

James nodded solemnly. “I will Claire, next time I will.”

“OK then, I’m holding you to that. I’ll even prepare for some serious ass wreckage next time. But you better not make me get ready for nothing or I’ll be upset mister.”

“I won’t Claire, I won’t let you down.”

“Good. Well, for now, just 15 then.”

“Just 15,” James repeated.

Claire took her customary position and reached her hands back to spread her cheeks wide open so James could more easily slide into her and open her up.

With Claire spreading her asshole like that, James could easily drive into her without sliding off. He pulled all the way out so he could keep dipping the tip of his cock into her ass repeatedly, enjoying the way his head slipped inside.

The constant entry and exit quickly started loosening Claire up as her asshole was stretched open for an instant before it was emptied. The feeling of cock filling her for just a second before it was pulled had never been satisfying or pleasant for Claire but she’d long gotten used to it.

“How’s it look champ?” Claire eventually asked after a while.

“It’s so pretty. You’re so pretty.”

“Save it Romeo, your times almost up.”

James immediately started giving her full length strokes while pulling entirely out every time. He loved the feeling of just sinking everything he had into her asshole. He liked how it felt like owning her, like it was making her his. But unfortunately, he still wasn’t all grown so he couldn’t get her asshole to look like the stuff he’d seen on porn, her gape was barely a couple inches across. So James reached into her ass with both hands and hooked four fingers into the sides before he started prying her open. He managed to pull her open wide enough he could almost make out the pink walls of her rectum if the light was right.

“Huh, that’s new. Who taught you to do that?” Claire asked casually.

“N-No one? I just wanted to see you open wider.”

“Alright, well, you could’ve just asked.”

Claire reached further back and her fingers joined James’. She reached in from the top and bottom while James pulled her open from the sides. Together, they pulled her so open so wide James could easily see everything inside her.

“Claire, can you stay like that?” James said in a distant voice.

While Claire held herself open, James started fucking into her again, his cock sliding down into her ass, past her fingers.

Eventually with a groan, James started shooting his load into Claire, giving her erratic pumps with every spurt.

“All done?” Claire asked brightly when she felt him jittering.

“Yup,” James said, breathing heavily and slumping over her ass.

Claire pulled off him, got to her knees and spun around. She bent down and brought her mouth down on his cock, sucking the mixture of his leftover cum and her ass juices off him, then giving him another once over just to make sure she got it all. Leaning back to look at the spotless cock, she gave a nod of satisfaction.

“You’re so cool Claire, none of the girls at school do ass to mouth.”

“Please, that’s because their tweens. We all had trouble doing that stuff back in high school. They’ll grow out of it, we all do.”

“I still think you’re cool.”

Claire shook her head. “You’re such a dork.”

As Claire went to clean up and dress, James stopped her. “Hey Claire?”

“Yeah?”

James looked off to the side nervously. “Can you… Can you drink it again?” he asked, pointing at her crotch.

Claire tilted her head to the side. “Well look at you, all grown up and getting girls to eat your cum out of their assholes already.”

“Please?”

“Maybe later. Do your homework first and help me with a few chores. And if you don’t whine-“

“I never whine.”

“And if you don’t whine, I’ll drink it. And if you’re extra, extra good, I’ll let you feed me it.”

James smiled from ear to ear at first before his expression turned suspicious. “Wait, if you wait that long won’t it all leak out?”

Claire gave him a look of fake hurt, bringing her hand up to her heart. “Ow, that stings. You need to learn how to talk to girls champ. Calling us loose is not gonna make you popular with the ladies.”

James looked mortified. “I’m sorry, that’s not what I meant.”

Claire gave him a serious look for a few seconds before she broke with laughter. “I’m just kidding. Kinda. You get a pass for being little but you better not say that stuff around girls later. It’s not gonna be cute for long.”

James nodded feverishly.

“But anyway. It’s not going anywhere okay? I’m all puckered up and I’ve got a buttplug somewhere. So don’t worry, that cums not going anywhere except in my mouth. But later, alright?”

“OK Claire.”

~

Later, as the two were hanging out, Claire brought up the school stuff again as she stared at James’ black eye.

“You know, you should tell the guys at school you’ve got yourself an adult that’s consented. I bet that’d make you real popular.”

James seemed to consider it for a moment before frowning. “And a bigger target. Ethan and his minions will just have another reason to mess with me if I do that. Probably get so jealous they get even worse.”

Claire didn’t seem convinced. “Maybe, maybe not. I think I know guys a bit better than you do champ. I think they really might leave you alone if they find out about me.”

“Well… If you say so, I guess it’s worth a try. So, do I just tell them at school next time I see them?”

“No dummy, they’ll just think you’re lying to seem cool. I’ll talk to your parents and ask if I can pick you up one day. But first, we’re gonna need to do some shopping to prepare.”

James’ shoulders slumped and he groaned immediately. Claire threw a pillow at him. “Trust me. This shopping is the kind you’ll like.”

James gave her a suspicious look but eventually relented. “Fine, if you say so.”

~

After helping Claire with some chores around the house and an hour of working on his homework in his room, James eventually went downstairs to collect his reward.

He found Claire half bingeing a show and half playing on her phone downstairs.

“Hey Claire?”

Claire looked up from her phone. “Yeah? What’s up champ?”

“I finished my homework. So can we do that stuff now?”

“Slow down there, I have to check your work first.”

As Claire went over his homework, James entertained himself by sitting at her side and gently playing with her tits. He thought they were so soft and squishy he couldn’t get enough of them.

After a quarter hour, Claire eventually delivered her verdict. “Everything looks good except your titration equations. I thought we went over that enough last time?”

“We did… But then I kept getting them mixed up afterwards. Sorry Claire.”

She tussled his hair again. “It’s fine, I’ll just help you study them more later. But right now, time to have some fun,” she said clapping her hands together and rubbing them comically.

James immediately brightened up.

“Grab that glass will you?”

James looked over at the coffee table and spotted a little shot glass. “This one?” he asked holding it up.

“Yeah. Make sure you catch it all, I’m not eating it off the floor since you haven’t vacuumed yet.”

James nodded.

Claire stood up and turned around so her ass was in James’ face, then pulled her shorts down. The buttplug was there, just like she’d said.

“Are you ready?” Claire asked.

James positioned the glass under her asshole. “Yeah, I’m ready,” he said, heart thudding with excitement.

Claire grabbed the plug by the base and pulled it out with a wet plop. Worrying it would leak out had been a completely unfounded fear though because nothing came out even as James watched Claire try pushing. Only after quite a bit of effort did his load finally squirt out of Claire’s asshole suddenly and flood the glass.

The white fluid kept flowing out of Claire until it had filled half the glass. When Claire felt like she had pushed everything out, she turned around and got on her knees. Giving James a thumbs up and a wink, she opened her mouth, stuck her tongue out and tilted her head back, obediently waiting for James to feed her.

James held the glass above Claire’s face and slowly upended it, pouring the fluid onto her waiting tongue. As it slid down the back of Claire’s throat, she sputtered once, almost coughing up her creamy drink. Eventually when she felt no more being poured into her mouth, she gulped loudly once and drank everything down.

Claire shook her head and stuck out her tongue with a sour expression. “So, how was that champ? You enjoy that?”

James nodded dumbly, happy in the afterglow of having Claire drink his cum from her ass.

“Well you better have. You’ve gotta enjoy it enough for the both of us.”

~ Shopping Trip

The next day when Claire came over to sit for James, she decided it was time for their shopping trip.

“Alright champ, you all set to go?”

“Yeah,” James replied unenthusiastically.

“Hey, remember what I said, this is the kind of shopping you’ll like.”

“I believe you, it’s just, hard to get excited for shopping, you know.”

Claire smirked. “Maybe this’ll change your mind,” she said, tossing him a little gift wrapped box.

“What’s this?” James asked.

“Why don’t you open it and find out genius?”

James shook the small box. It sounded light but metallic. He tore open the gift with building excitement. “A collar?” he asked, confusion clear in his voice.

“Yup. I thought you might have fun leading me around on it. My last boyfriend really liked that sorta thing and I thought maybe you might too.”

The thought hadn’t occurred to him before, but thinking about it then, James thought he would like it.

“Thanks Claire! Can I put it on you now?”

“Don’t mention it, and sure, why not.”

Claire got down onto her knees and let James clasp the collar around her neck. It was a simple, thick black leather one, but James instantly loved seeing Claire in it.

“Go on,” she said. “Lead me around a little.”

James was so excited he fumbled at the clasp a little as he attached the chain that came with it to the collar. He walked Claire around the house on her hands and knees for just a little while, but found he loved every moment of it because it felt like owning her, like she was just his property to have fun with.

“So whatdya think?” Claire eventually asked.

“This is so cool Claire!”

Claire chuckled. “If you think this is cool, you should try it when I’m not wearing anything but a few toys.”

James grew giddy at the thought. “I can’t wait until I’m older and I can do this all the time,” he said longingly.

“Woah, slow down there, you’ll need to find yourself a lady friend first.”

“Why? If there’s Free Use, can’t I just do this with anyone?”

Claire shook her head. “Sorry champ, Free Use just covers sex and the immediate ancillary acts. Gotta find yourself a girlfriend if you wanna do kinky stuff.”

“Oh… Okay,” James said dejectedly. “Well, thanks a lot for letting me do this with you Claire, I’ll know what I want now.” James sighed wistfully as he stared at Claire on her knees, wearing the collar. “I really hope my girlfriend is half as cool as you when I get one.”

“Aww, that’s sweet, thanks champ.” She reached up and tussled his hair again. “So what do you the collar to say?”

“What?”

“The name on the collar, I haven’t gotten one engraved yet, I thought we could do that today at the mall.”

James hugged Claire. “You’re the best,” he repeated

Claire laughed and brushed him off her. “Cut it out dork. So, name, any ideas?”

James thought for a moment before answering. “Uhm, how about, anal whore?”

Claire gave him an unamused look. “I’m gonna let that slide because your young and most importantly, lame. But that one’s been used like a billion times. I figured you could come up with something more original.”

James frowned. “Well maybe it’s been used a billion times because it’s a good name.”

“Yawn.”

“Ugh, fine. How about… Best Babysitter?”

Claire started laughing. “That’s one way to advertise, hahaha. I kinda like it, as lame as it is. You sure that’s what you want?”

James shrugged. “Maybe. I don’t know. Do you have any ideas?”

Claire hummed. “I could just put your name on it?”

James was gonna brush her off since it seemed lame as well at first, but the more he thought about it the more he liked it. It was almost like Claire was saying she was his property and that made him feel fuzzy in a new way.

“I like that,” James said quietly.

“Really?”

James nodded.

“Alright it’s settled,” Claire said, climbing to her feet. “Now go put on your shoes so we can go shopping.”

James practically ran to get his shoes on. “Now look who’s excited to go shopping,” Claire mused.

~

When they got to the mall, Claire led the way and brought James to the far end of the mall, away from all the clothing boutiques and food courts. Back there, the shops grew more and more adult oriented. Eventually, they stopped outside a shop called Toys in Us.

“We’re going in there?” James asked.

“Yup, sure are. I thought you might enjoy picking out a toy for me to wear when I pick you up from school to show off, and maybe one just to wear around the house when I’m over babysitting.”

James hugged Claire again hard, burying his face in her tits. “I love you Claire.”

Claire smiled down at him. “I like you too champ. Come on, let’s go in.”

The store attendant came over to greet them when they came in.

“Hi there, how can I help you?”

“Oh hi, we’re just looking for a toy to wear; buttplugs, tails, that sorta thing.”

The clerk nodded in understanding. “Of course, if you’ll follow me.”

As the clerk brought them deeper into the shop, she made some small talk. “So who are you shopping for? A girlfriend, partner or just frequent fuck buddy?”

Claire blushed. “Oh well, I’m not actually the one doing the shopping. He is, for me.”

The clerk turned to look at Claire and then at James with surprise. “Him? Really?”

Claire smiled and shrugged. “What can I say, I like the little guy.”

The clerk turned to face James. “You’re very lucky young man, most guys your age don’t get to plug a girl until their much older.”

“I know. Knowing Claire’s the best thing to ever happen to me.”

With her looking ahead, James didn’t notice the corners of Claire’s lips curl up in a smile at his words.

The clerk brought them to the plugs section of the store. Inside tall glass cases were shelves upon shelves of all sorts of toys that you could plug a girl with.

“So, did you have anything in mind?” the clerk asked James.

“Sorry, no, I don’t really know much about this stuff.”

“That’s alright, just have a wander and look around then.”

As James walked down the aisle, his eyes scanned across the shelves and he imagined putting each of the toys into Claire. He was like a kid in a candy shop had a hard time choosing a favorite; he just liked the idea of putting every one of them inside her. But he found the further down the aisle he went the more he liked what he saw on display. The toys got longer, thicker and more intense looking the further he walked.

Eventually, his eyes settled on a very tall cardboard box. “Wow… I like that one,” James said.

The clerk nodded. “Oh that’s a good choice.”

Claire followed their gaze and whistled when she saw it. “Wow is right. Jumping right into the deep end champ.” She turned to address the clerk. “Is it really that long?” she asked, pointing at the picture on the box.

The clerk nodded. “Yeah, the picture’s to scale. That one’s called the Gut Buster and it’s one of our more popular ones,” she said. “I’m actually wearing one of them now so I could give you a product demonstration if you wanted.”

James eyed widened and he leapt to say yes.

The clerk turned around so her ass faced the pair. James only then noticed a strange, blocky outline underneath her pants. The clerk then pulled her work pants down slightly to show the thick, heavy, black base of the toy. She gripped the base and began hauling out the toy. It wasn’t easy. The toy was so long that the clerk couldn’t even pull it out in one motion, she had to let go and grab the shaft to pull the rest out, and it was so heavily studded that the girl had trouble keeping still. Every bump that slid past her ring seemed to make her twitch a little. James was in awe as he watched the store employee remove the enormously long toy from her asshole. The toy was so long, it was practically swimming in her guts that whole time.

When she’d finally gotten the whole thing out, she turned back around to face them and held the toy in both hand. To her credit, she quickly managed to recover and remain professional, immediately launching into the sales pitch.

“So here she is. She’s 14 inches long with an eight inch circumference so it’s a real struggle and accomplishment to get it all in.” She pointed at the thick, tall nubs that studded the whole length of the toy on all sides. “It’s also heavily studded to provide maximum stimulation during insertion and movement. And I can say from personal experience, it’s an absolute nightmare walking around in it all day, you feel every bump moving and rubbing around inside you. It’s made of semi rigid silicon so it’ll follow the bend of your ass and colon, but only a little. It’s rigid enough that it bulges through your stomach at the right angles.”

“Can we give it a test drive?” Claire asked.

“Of course,” the clerk said. She handed the toy to Claire and went over to a nearby chair made just for product testing. The chair was angled back and didn’t have much of a seat, so if you sat in it, your ass would mostly be hanging out in the air, but that was the point. It had stirrups for resting your legs and feet in and they looked like they could be maneuvered into whatever position you could want. Finally, there were these heavy straps that looked like they went across the legs, thighs and stomach.

The clerk pulled her pants a bit further down then sat in it and put her feet up before strapping herself in, though with her pants still on, she couldn’t spread her legs apart.

Claire looked impressed by the seating arrangement. “That look’s handy, but what are the straps for?” she asked.

The clerk chuckled. “Yeah, it makes it a lot easier to test out most of our products. As for the straps, they’re just for keeping us in place. Sometimes employees have a hard time keeping still with particularly intense toys.”

“I’ll bet.” She turned to James and handed him the toy. “Go on, try it out.”

James happily took it and went over to the clerk’s side. He quickly planted the tip of the toy against her asshole and started pressing in. With inexperienced motions, he just kept feeding the toy in without giving the clerk any time to adjust like someone older would know to do. The clerk stiffened and sucked in a breath through her teeth as James carelessly shoved the toy inside. “Wai-“

The store employee’s body arched and a high pitched groan escaped her lips when the toy hit her sigmoid colon and **** the bend straight after being pushed past.

James liked the sound so he pulled the toy back a few inches before pushing it in. He felt the toy hit that familiar obstacle he’d carelessly pushed past just seconds ago and did it again. The clerk squealed that time and writhed in her seat.

Claire just laughed as she looked on. “Oh shit, I’m in for a rough one. I should ask your parents for extra.”

James didn’t understand what she meant by that so just kept feeding the toy into the clerk. Within moments he had shoved the whole thing back in down to the base. With the toy finally resting in her, the clerk relaxed and went limp in the seat at the reprieve. But before a moment had gone by, James started pulling the toy out again, making her strain against the straps.

Despite the torturous experience, the employee managed to stay professional and pulled her uniform up to just underneath her tits, exposing her flat stomach. James suddenly saw that every time he pushed the toy in, it would cause a small bulge to travel up her stomach. Staring at the mesmerizing sight, James experimentally angled the toy up and pushed, making a small mound raise up in the clerk’s smooth skin.

“As you can see,” the employee groaned, twitching futilely all the while. “The toy’s deep in my guts and very visible.” The bulge marred her otherwise flat stomach, just under the ribs.

“Oh wow, that’s so cool.” James turned to Claire. “Claire, can we get this one? I want you to wear this one,” he said pleadingly.

She eyed the bulge in the employee’s stomach. “Are you sure you want that one champ? It’s gonna really turn my guts inside out.”

“Pleeeeeease?”

Claire shook her head in bemusement. “OK, it’s your choice. But I don’t wanna hear any complaints that I don’t feel tight after you use that on me.”

“I won’t, I promise.”

“OK, so, that’s the one for the pickup sorted, what about one for around the house?”

“You won’t wear this one around the house?” James asked disappointedly.

“Sorry champ, no way I’m wearing that thing all the time.”

“Oh.”

“But, that’s not saying I’ll never wear it. Might happen, once in a while. But only if you’re being good.”

James brightened up at that.

“Come on, go find another.”

The two went back to browsing the aisle, leaving the employee still strapped in her seat and telling her to stay there. Eventually, something else caught James’ eye; a box with a girl wearing a tail. It wasn’t just a tail though; the tail was just the end of another very long toy. This one was a string of anal beads, though it would’ve been more appropriate to call them balls. They looked bigger than golf balls and there were eight of them in total. What caught James’ eye the most was each of them looked torturously spiked. Every inch of the balls were covered in long, thick semi-rigid spikes that spun. Not only that, but the box advertised the toys each had vibrate functions. Luckily for this product, it had a display model out in the open. James quickly grabbed them and rushed back to the employee.

He quickly tore out the Gut Buster, eliciting a groan from the clerk and started shoving the new balls inside her one after the other until just the cute tail was visible.

Impressively, she managed to talk through it all, only struggling against her restraints a little. “T-these feel like the Heavy Tail. T-this… Oh God… This one’s a good choice for private use. The spikes are… ugh… really intense.”

Each ball that James **** in drew more groans and struggling from the employee, but he thought that was a good thing so didn’t stop stuffing in the balls. He struggled to fit the last two in, but with a bit of shoving, he managed to just barely squeeze them in. The last ball that popped inside made the employee gasp and strain against her straps, but they were all in.

“Si-fuck-since these are balls instead of the semi-rigid toy like the Gut Buster; the sl-slightest movement shifts all of them inside you. They make it hard to concentrate or even think. I-I can feel every one of the nubs pressing against the walls of my ass.”

James turned to Claire. “What do you think Claire? That all sounds really good to me.”

Claire chuckled. “I’ll bet. It just sounds like one rough night to me. But if these are you two you want, these are the two you want.”

James faced the employee again. “The box says these have vibrate functions, how do I turn them on?”

The clerks eyes widened a little and she gulped. “These? Uh, there’s a remote that comes with them, but these are display models and they might not have batteries. You’re best going home and testing them on your friend Claire there if you want to see them in action,” she said hurriedly.

Claire held up the remote she’d taken after James ran off with just the beads. “You mean this one? Well, it couldn’t hurt to try right?”

She flipped the switch and the clerk immediately tensed up and strained hard against her straps.

“Oh that’s good, they do work,” Claire said.

A long groan escaped the clerk’s throat and didn’t stop. The two watched her bite her lips hard as her eyes rolled up into her head. Claire and James watched for a minute in interest before flipping off the toys. The employee seemed to collapse into herself and suck in heaving breathes. She didn’t look like she’d be able to talk for a while.

Claire whistled at the display and turned to give James a serious look. “You better not ‘forget’ to turn them off if you use those on me, little man.”

“I won’t,” James promised.

“Good, because I can’t take care of you if I’m a drooling mess. Alright then, so you’re sure these are the two you want?”

He nodded eagerly, he couldn’t wait to get home and try them out on Claire.

“OK, let’s get them rung up.”

The employee sighed in relief and began unstrapping herself.

“Oh, I almost forgot to give you this back,” James said, grabbing the Gut Buster.

The clerk wasn’t prepared at all when James grabbed the tail and tugged the long string of anal beads out. As each ball popped free of her she writhed and convulsed at the sudden gnawing emptiness inside her. As the toy finally came completely free, she wasn’t even given a moment of rest before James started feeding the Gut Buster back into her. She yelped as it abruptly entered her then squealed louder when it was **** past her sigmoid colon and into her large intestines. In moments, James had shoved it to the base, burying it deep back inside the employee’s guts.

She turned to Claire languidly. “You really need to teach him how to put these toys in properly,” she said exasperatedly.

James looked back and forth between the two. “Why? What did I do wrong?”

Claire tussled his hair again. “Nothing, you’re just a bit too… enthusiastic. Not everyone likes that.”

“That’s one way to put it,” the clerk said testily.

“You’ll get the hang of it eventually,” Claire encouraged.

~

“So, which of these bad boys do you want to give a test run first?” Claire asked when they got home.

“The Gut Buster! I wanna put the Gut Buster in!”

Claire laughed lightly. “Okay okay, let’s do that one.”

Claire pulled off her shorts and went up to the table. She placed her hands flat on it and planted her feet to the sides then bent over slightly, inviting James to put the toy in.

James eagerly took out the toy and squeezed a dollop of lube onto the tip like Claire had taught him and rubbed it around. He then placed the tip against her asshole and began to push it in. “I won’t be so enthusiastic Claire, don’t worry,” he said, remembering what she told him back at the store.

“Hmmm? Oh that clerk. Honestly? I think she was just being a little whiny. You weren’t even going that hard or fast. Don’t worry about that stuff with me little man.”

James smiled and hugged her from behind, making Claire laugh. “Go on, have some fun,” she said, shaking her ass back and forth a little.

James gripped the toy by the base and began feeding it into Claire’s ass. James watched in awe as the inches quickly disappeared inside her. The part he liked best was the way the big bumps on the toy would make her ass stretch this way and that as her skin slid over each one. Eventually James hit that familiar resistance that had made the clerk squeal when he shoved past it. But when James jerked the dildo in and **** Claire’s sigmoid colon straight, she just grunted once before relaxing again. In seconds, James had **** the whole 14 inch toy up Claire’s ass to the base.

When Claire felt the base pressed against her skin, she let out a held breath. “Damn, I think I can feel that thing in my lungs.” She turned to look at James. “You’re lucky I like you so much champ.”

“Thanks again Claire. How’s it feel?”

Claire grabbed James’ hand and guided it to the bulge in her stomach. He pressed down on the toy, shifting it inside Claire and making her groan, but she didn’t retreat from his testing touches though her knees did bend a touch. James pressed the bulge, shifting it across Claire’s stomach, rearranging her insides all the while. Claire buckled at the treatment but stayed put.

“I feel like it’s kicking my ass. Let me tell ya, those studs really are something else. Felt like you were shoving hundreds of anal beads into me.”

“Cool,” James said in a quiet, drawn out way.

Claire rolled her eyes. “Course you’d say that. Well look, I’m not wearing this thing again until I pick you up from school so you can show me off to your friends, but since it’s already in, you might as well do a few laps with it.”

James immediately brightened up at that. “You’re the best Claire!”

“I know,” she said smugly.

James grabbed the base and quickly began pulling the toy out, making Claire shiver as it slithered out of her. When nothing but the tip was left inside her, James palmed the base and shoved it all back inside.

As practiced and good as Claire was at taking it up the ass, even she couldn’t handle the anal onslaught James was giving her. He continually pulled practically the whole toy out of her only to shove it all back in moments later. The massive toy was pulverizing her insides and despite her best efforts, she could hardly stand straight after less than a few minute. She had to call it quits another minute in and pulled over a nearby stool to sit down on. She immediately collapsed down on it and scooted her ass over the back so James still had access to her asshole. She could still feel the massively long toy demolishing it’s way through her rectum and colon, but at least that way she could sit.

She waited James out as he abused her asshole, throwing the 14 inch toy into her ass and tearing it out. After a few minutes, she looked back and saw that he didn’t seem like he was close to finishing any time soon. She shook her head in amusement. Guys are all the same. Well, he’ll get tired of destroying my asshole sooner or later.

It took close to half an hour but Claire was right. James eventually had his fill of ruining his babysitter’s asshole with the 14 inch toy and stopped.

“That was so fun Claire! Your asshole looks so pretty when it’s swallowing that thing, but I think I wanna cum now,” James said as he spun her around on the stool.

Claire sighed with relief that he’d finally had enough and was grateful when she felt him spinning her around and lowering the stool. Knowing what that meant, she bent down on the stool so she could get low enough to get his cock into her mouth. She thought James must have been more excited playing with her ass than she realized because it only took a few minutes before she felt him spurt his load into her mouth without warning. She gulped down in time with each spurt so her mouth wouldn’t fill. After swallowing what felt like a shot glass of the stuff, she felt him finally simmer down.

Claire took the time to pull out the ridiculous toy from her asshole. The good news was she finally got to remember what not being stuffed to the gills felt like. The bad news was she realized her ass just wouldn’t close. She stuck several fingers in there before she felt her fingers brush the sides of her asshole. Great, it’ll be days before I feel tight again.

Claire got off the stool and tried to stand but her legs were weaker than she realized and immediately collapsed.

That snapped James out of his post blowjob haze. “Claire are you okay?”

She nodded. “Yeah, just a little more worn out than I realized.”

“Did I do that?” James asked guiltily.

Claire chuckled. “Yup, you sure did.”

“Sorry Claire,” James said, sounding even guiltier.

Claire brushed him off. “Don’t sweat it champ, it happens to all of us every now and then. Just help me up over to the couch.”

James did his best and managed to eventually get Claire to the couch, but struggled under her weight the whole time. By the time they collapsed on it, they were both out of breath. James tiredly snuggled up to Claire and laid his head across her stomach.

“You sleepy champ?”

James nodded.

“I’ll bet you are, all that work ruining my butt. I’m pretty tired too, I think it’s a good time for a nap.”

James nodded again, though more weakly. He rolled onto his side and quickly drifted off to sleep. His hand moved up, searching for the cold side of the pillow like he usually did, but instead of a pillow, he found Claire’s ass. And instead of finding the cold side of the pillow, he found something warm and soft, his hand unconsciously trying to get inside it.

Claire startled as she felt James’ fingers explore her ass lightly at first before they tried working their way inside her. She thought he was pushing his luck but when she looked down and realized he was sound asleep, she just chuckled to herself and tried to doze off herself. It wasn’t hard, it wasn’t like it would be the first time she had to go to sleep with someone’s hand in her asshole after all.

Later, James woke up to a very pleasant surprise as he found his hand buried in something wet, soft and warm. It took him a few moments before he realized his hand was inside Claire’s asshole. When he did, he started flexing his fingers and twisting his fist while still inside her, enjoying how soft she felt inside.

Claire woke up with a moan to the familiar sensation of something stirring in her ass. James didn’t seem to realize she had woken up so she coughed to get his attention. He immediately stopped fisting her.

“Morning sleepy head. Whatcha doing there?” she said, accusingly.

“Uh, well, I just woke up and my hand was there and I thought if it was already there, then I could play with it a little.”

“Uh huh, well, you can’t. Take your hand out of my asshole James.”

He reluctantly pulled his hand free with a wet plop and trailing viscous ropes. “You’re supposed to ask me first before you do things like that. You’re not old enough for Free Use yet, so you still need my consent okay?”

James nodded guiltily.

“So? Are you going to ask?”

James looked at Claire in confusion. “Ask what?”

“If you can play with my ass.”

“Claire, can I play with your ass?” James asked uncertainly.

“Yes you can.”

James smiled and plunged his hand back into Claire’s warm asshole.

“You’re the best Claire.”

“I know.”

~ Pickup

James was rutting away at Claire’s ass with nervous excitement. Partly because tomorrow was the day Claire would come pick him up after school, giving him the chance to show her off to all his classmates, hopefully getting Ethan off his back and partly because Claire always wore her collar whenever she was babysitting him those days. Seeing her with his name engraved on her collar sent a shiver of excitement through him every time and it only got better when they went out with it on.

Just thinking about showing her off in her collar and toys made James almost dizzy with excitement. He couldn’t wait to impress his friends with her. Feeling pretty good, James took a chance and asked Claire for a rare treat she sometimes gave him.

“Claire?” James asked as he slowed to a stop, though Claire continued to squeeze his cock in her ass.

“Mmm?” Claire replied, not looking away from her book.

“Do you think I could break your asshole a little today? Just a little?”

Claire didn’t look back as she answered. “You know the rules champ, no wrecking my ass except for A+’s or for special occasions and today there’s been neither.”

James’ shoulders slumped but he’d been half expecting the answer. Not everything could go his way.

Claire hummed and put down her book. “But I suppose it’d make a good impression for tomorrow. OK how about this; a little ass breaking tomorrow, but just a little prolapsing so your friends see.”

James nodded vigorously. “Just a little, got it Claire, thank you thank you thank you.”

“You better not go overboard trying to impress them,” Claire warned.

“I won’t, I promise,” James said.

Claire chuffed and went back to her book while James got back to pumping her.

~

James could barely keep himself in check as he went to the front gate with his friends. Scanning the cars parked out there, he quickly spotted Claire leaning against her top down’s passenger door wearing a short top that stopped just below her nipples and tiny booty shorts that showed off most of her ass. Claire didn’t usually go out showing so much skin but since James was showing her off she made an exception.

Claire shifted constantly as James approached with his friends in tow, trying to get comfortable impossibly with the Gut Buster fully lodged deep inside her. Driving with that thing inside had been a nightmare; every little bump in the road made itself felt in the most intense way.

She waved at James as he got near.

“Hey Claire,” James said.

“That’s your babysitter?” one of James’ friends asked incredulously. “I take back everything I said.”

Claire raised a brow at the new arrival. “And what have you been saying?”

“Uh, nothing, nothing at all,” the boy quickly replied.

“What’s that?” one of the others asked, pointing at the bulge in Claire’s stomach.

Claire looked down at her stomach unhappily but kept it from showing on her face. She wasn’t one to be vain but she was quite proud of her smooth, flat stomach and didn’t like the thick bulge running across her skin the Gut Buster raised. Claire couldn’t understand why some guys seemed to love the sight so much.

“Oh that? That’s just the toy James likes to have me wear,” Claire said, pressing her hand against the bulge and making it shift torturously across her stomach.

“I keep telling you guys Claire’s the best,” James said smugly as he moved forward and pulled down her shorts, revealing she wasn’t wearing any underwear.

Claire didn’t even move as he did, letting her shorts fall around her ankles. “Oh did you want a quickie before we go?” Claire asked lightly.

James nodded as he took out his slowly hardening cock.

“Alright but we gotta go soon, you know I have to get you to that appointment,” Claire said as she gripped the Gut Buster’s base and slowly dragged it out of her colon.

The boys’ eyes widened more and more in shock as they realized the sheer size of the toy Claire was sporting. By the time Claire had hauled the whole thing out, almost every student nearby was looking her way wide eyed. Backing her ass up on James, she slipped him inside her well used hole with trivial ease before she started the slow job of cleaning the Gut Buster, eliciting even more shock from the gathered crowd of students. Holding it in her hands sideways, Claire dragged her tongue across the toy, making sure to clean it thoroughly of her ass juices.

James did his best to sound casual as he started talking with his friends, trying to carry on a normal conversation while they all stared slack jawed at his babysitter servicing him and making a whore of herself in front of hundreds.

“Dude… I didn’t realize this is what you meant,” one of the boys said to James enviously.

“I tried telling you guys Claire was the best,” James said as he slapped her ass, making her startle at the sudden sting.

Recovering, Claire pulled off James and spun down to her knees before swallowing him whole, sucking on him loudly for effect.

As James casually made Claire do ass to mouth for him in front of much of his school, James scanned the crowd and saw Ethan. Catching the other boy’s envious look, he knew the show Claire was putting on was definitely going to make life easier for him.

“She’s really cool. She lets me do whatever, like ass to mouth, creampie swallowing or gaping whenever I want,” James said, talking about Claire like she was a thing.

“Like check this out,” James said as he pulled Claire up and bent her over her car door. Shoving eight fingers inside, James pulled his babysitter open as wide as he could, showing off her hole to his friends. Claire took that as her cue and pushed out at the same time, so James’ friends could see her pink, wet meat. It wasn’t much of a prolapse but it did the job of giving everyone a view of her guts.

As James’ friends and schoolmates stared speechlessly, he grabbed himself by the base and shoved himself inside, before flicking his cock out sideways and repeating. “Cool, right?” James said as he toyed with his babysitters asshole.

“I want a babysitter,” one of his friends said enviously.