Apple Butt 8: The Babysitter Spankings


by Skyler

The following epic is inspired by two favorite MMSA Stories archived stories. Don't forget about the other APPLE BUTT stories located under "SAWYER," "APPLE BUTT," and the ill-spelled "UNLCE ROD."

Bon apetite!

***

Time moved pretty quickly for Tom and his mother. Before they knew it, he was starting the eighth grade. School had just begun and Tommy was feeling good about himself. Everything seemed to be falling into place; he was going to be 14 soon; his Mom was finally happy; it had been a long time since he was last spanked; there was no more lamenting about the life that would have been had Tom's father had not died. Finally, the two of them were at a great place in their life.

With things improving, Tommy realized he needed some extra money. He had grown out of swimming, and was now planning on taking rowing in the spring, but crew was much more expensive than any other sport he could have picked.

"Figures!" his mother laughed. He rationalized that it would be worth it because if he could get a scholorship with crew, he could get into almost any ivy league school. Mrs. White liked that.

So, he looked around to find additional money any place he could. The most obvious choice was mowing the yards of the neighbors, but the town pariah, Chris, had the lawn-work market cornered.

"What about babysitting?" his friend, Skyler, suggested. "You get along pretty well with the little ankle-biters," he added, referring to the younger kids that were in their scout troup.

"That's an excellent idea!" his mother added, when she heard about that. "In fact, I bet you could watch Leo and Judy's children, Suzanne and Benny!"

Tommy grimaced at that thought, because he hated those hyper little brats, but he said, "Sure. I'll give them a call."

It didn't come as a surprise to Tommy when he learned that the Cleaverlys were thrilled with the idea of Tommy becoming their regular babysitter; "It's getting harder and harder for us to find good help!" Mrs. Cleaverly said.

Yeah, because you have two incredible creeps! Tom thought.

The first big test came and went with flying colors; the kids loved Tommy (they were all close enough in age that it was more like a buddy come over than some obnoxious older teen), and the Cleaverlys liked the way they behaved with him.

The next test came one dreadful Saturday night. Tommy's mother, Norma, was going out on a date with some dude named Markley. Markley was a much younger guy (not even old enough to be Tom's father), but he seemed to make Norma happy, which made her son happy.

One reason the Cleaverys trusted Tommy so much was because they always knew that his mother was always just across the street in case there was anything too big for Tom to handle on his own. Because Tom needed the money so bad, he decided not to tell them that his mom wasn't around this one night - he was afraid they would go with another babysitter, so he lied when he said that his Mom would be at home all evening.

When he got over there, he had two surprises waiting for him - the first was that little Suzy was spending the night over at a girlfriend's house; that was pretty good news, Tom thought, until he found out that the other surprise was that Ben had invited his friend, Chris, to come spend the night!

CHRIS?!! Tommy's heart got stuck in his throat. Chris, as in the same little kid that mowed everyone's yard and was also known as "HORSE" because he had such a huge _d_i_c_k_?! THAT Chris!!!???!!!

"He won't be coming by until about eight in the evening," Mrs. Cleaverly explained. "I hope that's not a problem."

"Yeah," Mr. Cleaverly said. "We should be home by ten. I told Chris' parents not to worry about you, because your Mom was just across the street."

"Ah, yeah," Tommy said, lying through his teeth. He was so afraid that another sitter would be called. In the year since he had first seen Chris at the rec center, and then later in his scout troup, he had becoming quite infatuated with the little hellion. Everyone else hated "Horse," but not Tommy.

Well, not yet at least.

Once Tommy and Ben were alone, the eleven year old turned into a royal terror. He was running, he was bouncing, he was jumping all over the place. Tommy was getting so sick of it, he told Benny to calm down, "or else!" He couldn't even imagine having to deal with TWO hyper eleven year olds!!

"Or else what!?" Ben taunted. "You gonna spank my butt like your Mommy spanked your butt that day?" the brat added, really pissing off Tommy - he hated it when Ben and his sister reminded him of that horrible welcome to the neighborhood. Especially since it happend years earlier!!

"Maybe!" Tommy said. "Just don't push me."

"Ah, _f_u_c_k_ you!" Ben said, to both of their surprise; he had been hanging around Chris too much!

"What did you say?!" Tommy yelled.

"Ah, nothing," Benny said, now slightly concerned that he was going to tell his folks that he cussed.

"No, you said something, Ben!"

"I just said, 'Ah, FORGET you!" the kid lied.

"Did you just lie to me, on top of cussing?" Tommy said. "Do you know what happens to kids who lie?"

"Ahhhhh..." Ben said, stalling for time. "They get ice cream?"

"Very funny! Come here," Tommy said, yanking the younger child towards him. "I've had enough!"

"Nooooooooo!" the little boy yelled, as Tommy took hold of him.

"Be quiet!" Tommy said. "You're getting a spanking whether you like it or not. You can't use words like that."

Tommy sat down on the edge of the couch, and began fumbling with the snaps on the front of Ben's jean shorts

"What are you doing!?" the kid screamed.

"This is going to be bare bottomed for you, mister," Tommy stated, putting both of his hands on the kids sholders and set him over Tommy's legs.

"I'm sorry, I'm sorry," Benny pleaded as Tommy gently slid his unnbuttoned jeans down to his ankles.

"Be quiet or you'll get extra," Tom said as he slid his thin cotton underwear down next to his knees.

Little Benny started crying a little, but the babysitter ignored him. Tommy then raised his hand a foot over the little boy's cute little rear end and slapped his upper bottom hard.

Ben cried louder. Tommy slapped his butt again, harder this time, making the kid cry even more. Again his hand smacked Ben's perfect ass.

"Nooooooooo!!!!"

Tom smacked him again, his bottom began to pinken up a little. The older boy waited five seconds then smacked his butt with all by strength - Benny was crying hard now, but that didn't stop Tom from slapping him a sixth time.

Then the seventh, his little bottom was becoming bright red.

SMACK, the eighth slap was delivered vertically, stinging his little puckered asshole, making Ben sqiurm a little. The ninth hard spanking was placed on his lower bottom, making him cry harder still.

The tenth slap lander on his lower back. He arched up and looked at Tom as if to say, "How dare you!?"

Next Tommy slapped the child right on the middle of his red bottom twice. The thirteenth made him yelp and kick the side of Tom's right leg as he cried. That resulted in the babysitter pulling both his legs under Tom's thigh, making Benny's anus clearly visible, as Tom smacked and smacked and smacked him hard on his inner bottom three times.

Then, still holding his legs, Tommy smacked his asshole as hard as he could. Tommy thought about how great this felt - he hadn't spanked anyone since that time with Alex, on the day he left. There was so much tension built up inside. Poor Ben had to take it.

That last smack really must've stung because Benny screamed as soon as the impact was delivered. Tommy let his legs go and smacked him the eighteenth time. The last two landed on his rosy colored bottom, then Tom helped Ben back on his feet.

Ben stood in front of Tom, tears running down his face as Tommy pulled his underwear and jeans back up. Tommy could tell that he hadn't been spanked much (if ever), because the little creep didn't take it well.

"Ben, since you lied," Tommy said, "You are going to get a second spanking..."

"W-w-w-what...?" Benny blubber, still clutching his inferno of an ass.

"And if you ever say that word again," Tommy threatened. "I'm gonna use your Mom's big hairbrush."

"That's not fair!" he cried.

"Life isn't fair, sport," Tom replied, looking at his watch. "Now, before Horsey gets over here, you should take your bath."

Benny didn't put up much of a fight, as he decided that by switching to a cheerful mood would make me forget Spanking Number 2 of the evening. It didn't work, as Tommy reminded him of the SECOND spanking: "Just so you know," the babysitter said, "The moment you get out of the tub, you're going back across my knee."

"Then I'm staying in the tub!" the cherub announced.

"We'll see about that!" Tom laughed.

Sure enough, for the next hour, every time Tommy came in to check on Ben, Ben said he was staying in the tub. That was until "eight" struck on the clock, and Horse arrived at the door.

"Where's Benny?" Chris asked Tom, in a voice that had already changed.

"Upstairs, soaking in the tub," Tommy answered, waving to Chris' parents in their car. "He won't come out, because he's going to be getting a spanking when he does."

"Really!" Chris laughed. "Cool!"

The two of them went up to the bathroom, and there was Benny - still soaking in the tub. "HEY!" Ben yelled, covering his privates, "GET HIM OUT OF HERE!"

Chris came over and sat by the tub. "Howdy, Ben," Horsey said, splashing the water a bit. "I hear you gonna get a spanking soon!" There is nothing more evil than one eleven year old tormenting another eleven year old on the subject of spanking. Naturally, Tom was loving it.

"Tommy!" Ben whined. "Make Chris go away! I'll let you spank me as long as he goes away!"

"Really?" Tommy asked, as Ben nodded. Tommy then made Chris leave the bathroom, as Tommy pulled Ben out of the tub and put the naked, pruned child over his lap.

"Can you close the door, please!" Ben said, as Tom ignored him.

"Hey Chris!" Tom yelled.

"Yeah, dude," Chris said with a smile, poking his head in the bathroom.

"Can you go in the other bathroom and grab the large hairbrush," Tom said, as Ben's body suddenly tensed. He really wanted out of there.

"Sure thing, boss!" Horse laughed, as he left and returned moments later, handing the brush to Tommy. "Here's your mighty Bottom Brush, sir!" he said.

"Thank you," Tommy said, still holding Ben tight, as he cried and wiggled. "You really should have come out of the tub when I asked the first time, Benny Boy!"

"Can I stay?" Chris asked.

"Sure, as long as you stay out of the actual bathroom," Tommy said, smacking Ben's butt hard with the brush. "Because I promised Benny..." SMACK! "...that you would have to leave the room..." SMACK! "...and since that is an open doorway..." SMACK! SMACK!! "...you can stay and watch..." SMACK! "...your friend get his butt smacked from there." SMACK! SMACK! "Isn't that right, Benny?" SMACK! SMACK!

Ten whacks with the brush, and Tommy let Ben up. The kid then went running into his bedroom and slammed the door crying up a storm. The little guy had never been so embarrassed in his entire eleven years. In the meantime, Tom and Chris watched television together, as Tommy began thinking of how he could find an excuse to get HORSE across his knee.

"Tommy!" Ben called out from up the stairs, interupting his plotting.

"Yes, Ben," Tom sighed.

"Can you come here for a minute?" he said. Tom moaned, and excused himself as he went to see what was up with Ben; he probabbly wants to apologize, and didn't want to have to do it in front of his buddy, Tom thought.

When Tommy got to Ben's room, he was surprised to find that Ben had just called over to Tommy's house.

"You what...?!" Tommy said, furious, and slightly afraid.

"I wanted to tell your Mommy that you spanked me, but she's not there," Ben said, through a tear-stained grin. "Where is she?"

"She must have stepped out for a minute," Tom said, trying to think on his feet.

"Yeah, right," Ben said, moving across the bedroom. "I also called Skyler, and he told me that his dad's helper, Markley, was going on a date with your Mom. Tonight!"

"Well, maybe she is, I don't know..." Tommy said, looking nervous, and suddenly becoming very uncomfortable being given the third degree by someone not even taller than five _f_u_c_k_ing feet!!

"You lied!" Ben accused. "You lied to my Mommy and Daddy, and Chris' folks and everyone and I'm telling on your sorry _f_u_c_k_ING ass!!"

AAHHHHHHHHH! _s_h_i_t_!

"Listen, you don't have to do that," Tommy said, reassuring. while ignoring the cussing. "I'll do whatever you want, just don't tell."

"You'll do anything...?!" Ben said with a glimmer in his eye. "Really?"

"Sure," Tom sighed. "Anything." Tommy really didn't want Mr. and Mrs. Cleaverly finding out that he had out and out lied about the fact his Mom was out that evening.

"Fine, first thing," Ben said, "You give the money Mom and Dad are giving you to me and Chris. Deal?!" Tommy thought about it for a moment and then nodded that that was fine. "Then, as payback for lying on top of lying, I should give YOU a spanking."

"What?"

"I should give you the kind of punishment I just got when I lied," he said. "Or I could just tell my folks."

That got Tom's attention again. If his folks believed him, Tommy knew he would get it worse from his Mom, and he would certainly be out of a job. And he really needed the money for crew!

"Okay, sport," Tom sighed. "You're the boss of me. I'll do whatever you think is neccesary."

"You mean it?" Ben was shocked.

"If that's what will keep you quiet, I guess."

"You know what to do, then," he said sitting on the edge of the bed, testing Tom's seriousness.

Tommy slowly walked over to Ben and stopped right in front of the kid. Once he was stannding in front of the little kid, Benny unbuttoned the buttons on Tom's pants, and the unzipped them.

"Does it have to be bare?" Tom whined.

"You bet!" Ben said, as he gave the jeans a couple of tugs until they came loose and slid down to his knees. "Step out of them, please," Ben said, as Tom did what he was told. Tommy then glanced over to the open door, and realied that Horsey was still in the _f_u_c_k_ing house!

_s_h_i_t_!

Moments later, Ben tugged the teen's undershorts down too, and he was ordered to step out of them as well, before spreading out over the boy's knee.

"Now," Ben said, running his small (but firm!) hand over Tom's ass, "This will hurt you a lot more than it will hurt me!"

_d_a_m_n_! Where had he heard THAT before!! Tom thought, as images of Alex danced in his head.

SMACK!

Since it had been a long while since he was spanked, Tommy had forgotten what to expect. The first lick actually stung.

SMACK! SMACK! SMACK!

Yow! Tommy wiggled a bit, as he noticed that little Ben was certainly developing his upper body strength!

SMACK! SMACK! SMACK!

Yikes!!! Tommy breathed deep but held back from groaning.

SMACK! SMACK! SMACK!

Benny laid into the older boy without mercy.

SMACK! SMACK! SMACK!

Tommy's eyes soon watered. He was pretty _d_a_m_n_ embarrassed to be crying from a firm slapping administered by an eleven year-old.

SMACK! SMACK! SMACK!

But boy did his buns hurt!!

SMACK! SMACK! SMACK!

In all, Benny gave Tom a wonderful gift of about twenty whacks (not forgetting to smack his hole!), just as he'd been given a couple hours earlier.

"This isn't over yet," he informed Tom.

"What do you mean?!" Tom asked, sniffeling.

"Go stand in the corner," Ben yelled, as Tom got off his lap, looking rather confused. "You spanked me TWICE, and that second time was in front of someone, so you still owe me. Got it?"

"I got it," Tommy said with a heavy sigh, glancing at the clock - it was almost ten! Ben's folks were going to be by soon!!

"Good," Ben said with a smile, as he left the room to go bring Horsey up to watch the fun.

About ten minutes passed before both boys came in. Tom was feeling rather sheepish about being left alone and totally naked up in Benny's bedroom.

"We're back!" Ben said with a cheer. "Didja miss us?"

"Just get it over with," Tom said, not wanting to look directly at Horse; this was just the pits!

"My, my, my," Ben said, looking at his little friend. "Our naked babysitter seems to be in a bit of hurry to get the spanking over with."

"Imagine that!" Horse laughed. That was when Tommy noticed the little kid with the supposedly big _d_i_c_k_ had THE HAIRBRUSH with him. _s_h_i_t_! _s_h_i_t_! _s_h_i_t_!!!

"Listen, just get on with it!" Tom was really getting nervous.

"Oh, we will," Ben said with a yawn. "At our own pace."

"I'll do whatever you want," Tommy stupidly promised again. "Just do it!"

"Anything!?" Ben squeeled at hearing the magic word. "I was hoping you would say that, Tommy!"

He then informed the babysitter that, in exchange for NOT taking forever to deliver the second spanking, that Tommy would have to submit to two additional spankings given right away...

ONE BY EACH BOY!!

Tommy sighed and looked at Chris, who was wide eyed and loving every minute of this babysitting encounter.

"Fine!" Tom said through his clinched teeth, as he was shoved instantly into postion back over Ben's lap. Horsey then handed his friend the "bottom brush," then stood back and waited his turn!

Ben winked at Horse as he took about two minutes to give Tom ten hard, sharp spanks with the brush.

SPANK! SPANK! SMACK!!

Tom tried to be as stoic as possible in front of his audience, but his butt couldn't help but squirm as his brush struck.

SMACK!! SMACK!! SMACK!!

They laughed hysterically, as it involuntarily moved and wiggled to try and avoid the next ...

SMACK!!!

Tommy grasped the side of the bed tightly and squinted his eyes, determined to hold back the tears.

SMACK!! SMACK!

He sniffled and wiggled under ten strokes of his brush.

SMACK!

"Stand up."

Tommy stood up, knowing that ten more were waiting me at Chris' hand were waiting.

"Hey, Benny! Check this out," Chris said. He pulled the front of his pants down slightly to finally reveal his lanky, thick _d_i_c_k_ a good four inches bigger than Tom's.

"His is WAAAY bigger than yours," Ben laughed, pointing at Tom's still hairless crotch. "And he's not even twelve, yet" Ben pointed out to complete Tom's humiliation. "Lean across his lap."

Chris tucked his massive one back into his pants, sat down, and leaned Tom across his lap. Tom couldn't help but think about the fact that he had always wanted to be in a spanking sitution with Chris...he just thought it would be the other way around.

"Here," Chris said, taking the brush. "Lemme show you how to paddle a naughty butt!"

And then, off he went! Twenty five, searing, blistering and very fast smacks fell across Tom's bare ass.

"You know, Ben," Chris said. "This is one of my favorite passtimes!"

The whacks continued to rain down.

"You are really good, Horsey!" Ben said, in awe. "Think you can teach me?"

Tommy tried to block out their conversation, but it wasn't working.

"Sure," Chris said. "I'd love to, Ben!"

Meanwhile, the teenager was crying and screaming, but never once getting up off ths kid's lap.

"Cool!"

Tommy took it as best he could.

"Are you having fun yet, Tom?" Chris asked in the middle of it. "Good," he said, answering one of Tommy's plaintive moans. "I am too!"

"WOW!" Ben said, in shock, when Horsey was all done. "That was really impressive."

"Like all things in life, you need practice," Chris said with a PHEW, now running his small hand over Tom's ass. "Just ask Skyler!" he added with a laugh.

Tom was then allowed to get up and slowly get dressed. Pulling up his undershorts actually hurt, as the two little elementary school kids watched in amusement. Tommy didn't know which hurt more, though; his ass or his pride.

"Well, now I guess we're even," Benny said.

"I guess so," Tommy mumbled.

About that time, Mr. and Mrs. Cleaverly arrived home. The three boys scurried downstairs as if nothing had just happened. When they got downstairs, that's when they noticed that Mr. and Mrs. Cleaverly were not alone:

Markley and Norma were also with them.

"Tommy," Mrs. Cleaverly said. "Did you know that your Mom was going out tonight with her friend, Markley?"

"Ah," Tommy said, still stinging from his beatings. "Yeah. I think so."

"So, you lied to us?" Mr. Cleaverly said, in disgust.

"I'm sorry, sir," Tommy began, as he was cut off by his mother, telling him to march his butt right home right that second.

"I'm so sorry about this Judy," Mrs. White said. "He's been a pretty good boy. I don't know what got into him."

"Yeah, he is a good kid, most of the time," Mrs. Cleaverly said. "We just need to know that we can trust him."

"I guess what he really needs is a good man around the house," Leo Cleaverly added.

"Exactly," Markley said, looking at Norma for some back up. She was hesitent, but she too agreed - at his age, he does need a strong man around.

About ten minutes later, Tommy got a fourth spanking of the night, this time at the strong hand of Markley, that made the three earlier ones seem like "love-taps." It wouldn't be his last, however.


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