Trolling the Babysitter
By Yu May, With Contributions by Anonymous

Tommy Goodluck ignored the quizzical looks from bypassers as he made his way to Mrs. Goltrode’s home for his next babysitting gig.

His facial features were graceful, and his figure slender, with the exception of his hips. Whenever he looked in the mirror, Tommy thought he looked like an exclamation point: narrow shoulders, narrow chest. Tommy never wore anything to look effeminate on purpose. Quite the opposite.

For a while, Tommy had tried wearing baggy shirts and sweaters, in a vain attempt to hide his proportions. But after Tommy had been whistled at by a man on more than one occasion, only for him to turn around and catch their annoyed, befuddled look as they took a closer look at him, Tommy had concluded that no amount of modesty could hide the truth. Today, Tommy was wearing a red and white striped collared shirt with blue jeans, and from behind, he was the spitting image of a young Anne Hathaway with a short boy cut.

He was also wearing his lucky underpants from childhood, as was his custom whenever he took a job for a brand new client. Although no one would ever see them, having them as a good luck charm always helped Tommy start off his day off right.

High school had been rough for Tommy, but it was there he’d discovered his calling: child-care. Most parents were biased against male babysitters, preferring young women, but Tommy’s reputation for respecting the rules of every family he worked for, and the popularity of his famous “bag of activities” amongst the kids he babysat, had traveled by word of mouth. After 10 years, 24-year-old Tommy Goodluck had established himself as the top-rated babysitter in the city, and was highly sought after by yuppie parents.

It was his first time in this neighborhood, an older part of town that had historically been settled by Danish immigrants. Tommy checked the pin on his smartphone map, and approached the Goltrode family home, which could have been a postcard with its red tile roof and cozy collection of wooden figurines in the garden.

…

Mrs. Anna Goltrode was dressed in a glittering evening gown, complete with feather boa, ready for a charity lunch, followed by an afternoon at the theater. “Remember, young lady, you’re to be on your best behavior for Mr. Goodluck!”
 
Her daughter was dressed in a simple red skirt with a black and white checkered blouse, in the tradition of their Danish-immigrant forebears. 

Celia Goltrode pouted. It just wasn’t fair! She was 10-years-old, so why did she still need a babysitter?

Mrs. Goldtrode flicked her finger against the poster hanging on the wall of the kitchen as she stared down at her daughter. “I’m giving your babysitter full permission to spank you if you misbehave. Do you understand, Celia?”

“Yes, Mother,” Celia answered dutifully as she examined the dreaded poster for the millionth time.

The top was labeled “Duty and Discipline,” in large pink letters, and the chart contained quite a bit of complex information, neatly organized in columns and rows. There was a row for “The 5 D’s” which included “Disobedience,” “Disrespect,” “Defiance,” “Dishonesty,” and “Danger.” Under each word was a definition, followed by a list of examples in neat bullet points. Below this was a calendar for the days of the week, with smiley faces and frowny faces to chart whether Celia was meeting her mother’s expectations for the week. 

Celia had nothing but smiley faces for the row labeled “Grades and Homework,” but she also had three frowny faces for “Remembering to Remove Shoes Indoors.” The rest of the chart was a more random mix of happy stickers, with only a few frowny faces.

Following the calendar was tightly written fine print in neat script defining the consequences for each offense. But thanks to the pink, plastic hairbrush hanging on the wall right by the chart, guests usually didn’t have to read the chart to guess what the penalty was for getting too many frowny faces.

The doorbell rang. “Ah! Here is Mr. Goodluck,” sang Mrs. Goltrode in a cheerful falsetto.

Celia was still feeling sorry for herself, so she didn’t pay much attention as her mother explained the house rules to the new babysitter. 

Tommy took notes, before gesturing to the poster on the wall. “Got it! Celia gets to play outside while I prepare supper. After supper, I’ll clean up, and we’ll read and do indoor activities! But what about this chart?”

“Oh! These are the house rules for what kinds of misbehavior merits a spanking!” Before she could walk Tommy through every detail of the chart, Mrs. Goodluck heard the grandfather clock chime. “Goodness! Look at the time! I must be off to the theater. Look this chart over when you have the time, Tommy, it’s self-explanatory. So long as Celia doesn’t track mud in the house again, I doubt you’ll even need it. Celia’s generally a very good girl! Well, I must be off!”

Mrs. Goltrode patted her daughter on the head lovingly, and Celia accepted the gesture of affection. She loved her mother and knew she was loved, but Celia couldn’t help but wish that just once, maybe for a day, she could be free from the dread of being one step away from a spanking. 

As Mrs. Goltrode hurried to her car, Tommy called after her, “Is Celia allowed any screen time?”

“Oh! Only half an hour! Thank you for asking! None of the other babysitters ever cared! Remember to be good, Celia, or someone is getting a spanking!” cooed Mrs. Goltrode, rolling up the window as she pulled out the driveway.

Tommy sighed. He wished he could have discussed the chart of spanking offenses with Mrs. Goltrode in more detail, but he was confident he could figure it out. The modern, suburban parents he usually babysat for generally disapproved of corporal punishment, but Tommy’s motto was always to respect the rules of every family he babysat for, no questions asked.

…

To her pleasant surprise, Celia found Tommy to be a great listener, even showing interest as she talked his ear off about her favorite doll, Poppy the troll. 

Later, while Tommy read the chart carefully, he let her watch a few mini-episodes of her favorite show, Trolls: The Beat Goes On. When the egg timer rang to indicate that 30 minutes were up. Celia tensed, waiting for Tommy to turn off her show in the middle like other babysitters had done, but Tommy instead put the chart and timer away. “I’ll finish this one with you,” he added as he sat down to finish the last minute of the show with her.

Celia wondered if Tommy would let her get away with watching one more. “These cartoons are so short! Don’t you want to watch one more with me, Mr. Goodluck? They’re really funny!”

“No, Celia, your mother said your screen time is limited. Go play outside while I make lunch.”

Celia didn’t make a fuss, and played outside. Sure, her little trick hadn’t worked, but maybe today wouldn’t be so bad after all. 

“Celia? Lunch is ready! I’ve made mac and cheese, with green beans. Take your shoes off and come in.”

Celia was so wrapped up in her own imaginary world, that she didn’t hear the last part. She zipped through the door and straight to the table, before spotting the trail of dirty tracks she’d left across the beige carpet. Celia was horrified. “I’m sorry, Mr. Goodluck!” she whimpered, imagining the spanking that was surely coming.

Tommy sighed, glanced at the sticker-covered chart on the wall, then fetched stain remover and towels from the kitchen cabinet. “It’s okay, Celia, eat your lunch while I clean this up. We’ll discuss your mother’s chart after you’ve finished eating.”

Celia felt like a convict on death row as she chewed her mac and cheese. One moment of forgetfulness was all it took to earn a free trip to Spanking Town, Lapland. And of all the days to forget, why did it have to be when she had a babysitter? And of all the babysitters, why did it have to be the only one who actually seemed cool? All the high-school girl babysitters had just ignored her and fiddled with their phones.

Tommy ate in silence, then cleared away the dishes. Hoping he had forgotten, Celia tried to creep away to her room. 

Tommy spotted his charge slinking away as he untacked the poster and brought it to the kitchen table. “No, Celia. We have to discuss your mother’s rules.”

Celia hunched her shoulders as she reached the steps, and turned back to the kitchen table, hanging her head. She knew there was no escape. It was spanking time. 

Tommy ran his finger along the calendar at the bottom of the chart. “Now, Celia, as I understand this chart, you’ve gotten three frowny faces for tracking mud in the house this week already? According to this chart, the first frowny face is a warning, so that means someone has gotten two spankings this week, already…”

Celia winced at the mention of “someone” getting a spanking, which was always her mother’s favorite phrase. Why was “someone” always her? Why couldn’t “someone” ever be “someone else”?

Tommy’s attention turned to the neatly written letters at the bottom describing the appropriate punishment for each offense. “And according to these rules, after getting a fourth frowny face, someone is getting a spanking with the hairbrush.”

Celia nodded, too ashamed to look her babysitter in the eye.

Tommy scratched his scalp. “Well, that part I understand, but your mother was in such a rush, I didn't have a chance to ask her any questions about the specifics of this chart. What I don’t get is who this someone is supposed to be. Are you the someone this chart is referring to?”

Celia snapped her head up. If she wasn’t so confused she’d be in tears already. Was Tommy teasing her? Dragging this out like a cat playing with a terrified mouse? He seemed so nice before. But as she examined his face, Celia thought Tommy seemed genuinely nonplussed.

“Uh…No?” Celia shrugged as she said it, hoping Tommy would take it as a joke.

Tommy activated his brain cells as he poured over the chart again, as if hoping it would come alive and speak the answer he sought. “Then who is the person who’s supposed to get spanked?

“Well, who do you think it’s referring to?”

Tommy shrugged. “That’s the problem! I assumed it was supposed to be you at first, but when I read the chart, I got confused. No matter how many times I read it, it’s still the same! On the one hand…”

Tommy rifled through his trusty babysitter backpack, and whipped out an antique copy of Correction that Corrects by Miriam Frederick, “I’m aware that corporal punishment has historically been favored as a method of child-discipline for centuries! But, on the other hand…”

Tommy produced a 21st century child-psychology textbook, decorated by a Norman Rockwell illustration of a mother taking a slipper to her child while examining a book on child psychology, “It seems that there is also a significant body of evidence linking corporal punishment of children to various negative side-effects! I don’t know what to think! I’ve never babysat for a family that had rules for spanking before, let alone rules this complicated!”

Celia was stunned. For her part, Celia was so used to spanking as an inescapable aspect of her daily life, it never occurred to her she might not get spanked for tracking mud in the house. On the other hand, she felt genuinely sorry for Tommy’s dilemma, but not sorry enough to tell him the answer to this riddle. “Well, suppose you ask my mom when she gets home?”

Of course, Celia knew that her spanking would come sooner or later, but at least it could wait until bedtime. In Celia’s opinion, whoever said there was no point in delaying the inevitable had never faced the prospect of being spanked.

Tommy buried his face in his hands. “But the rules are very clear that a spanking is to be administered immediately! Oh! If only Mrs. Goldtrode had been a bit more specific!”

Celia remembered every Bugs Bunny cartoon she had ever been allowed to watch, and for the first time in her life, she dared to hope for a path of escape. “Well, do you think Mom could have meant you?”

Tommy stared at the chart in horror. “Me? But I’ve never been spanked before! And I’ve never met your mother before! Why would I be the someone referred to here?”

“Well, you are responsible for me, after all.”

Tommy nodded. The responsibilities of babysitting were not just a job, but a sacred duty. “Correct. I am responsible for you.”

“And doesn’t being responsible mean you’re the one who gets in trouble if something goes wrong?”

Two of Tommy’s brain cells had a furious argument. One brain cell had a sneaking suspicion that being spanked would be highly unpleasant, and that something was strange about this whole situation. The other brain cell was dedicated to upholding the rule of law and the code of honor for babysitters everywhere. Tommy’s nobler side won the day. “You’re right, Celia! I’m the one responsible for upholding these rules, which means…” 

Tommy stared at the pink, plastic hairbrush, which still hung from the wall, menacingly. “I’m the one who has to pay the penalty! But then, who is supposed to administer this spanking? It’s got to be done right away!”

Celia had a small shoulder angel sitting on her right shoulder, pleading with her to face the music. But then her shoulder devil started playing a golden banjo, and Celia decided to go for it. “I suppose I could spank you, Mr. Goodluck! I know a lot about it!”

Mr. Goodluck froze, before wiping a bead of sweat from his brow in relief. “Would you? Oh, thank goodness, I was afraid I wouldn’t be able to follow your mother’s rules to the letter. But I don’t know how this works, Celia!”

 “Don’t worry, Mr. Goodluck, I’ll walk you through it, step by step. First, would you please help me reach the hairbrush?”

As Tommy took the pink plastic hairbrush from the hook, he realized it was decorated with an engraved image of Princess Poppy from the original Trolls film, the paint slightly faded, after years of loving use. In that time, Mrs. Goltrode had practically worn out the hairbrush on her daughter, by wearing out her daughter with the hairbrush.

Celia dragged her mother’s high-backed chair into the center of the kitchen, hopped up to seat herself on it, and held out her hand to accept the hairbrush. “Now, Mr. Goodluck, you want this spanking to be exactly like my mother’s rules for the house, correct?”

Tommy nervously handed over the implement. Ever since he was a kid, people had called him a wimp, and much meaner names. What if he couldn’t take a spanking? “Of course, Celia!”

“In that case, lie carefully across my lap. It may sting a bit, but if you’re brave and hold still, we can get this over quickly.”

As Tommy settled into place across Celia’s lap, she was struck by how light-weight he was. In a $few years, Celia thought she might be stronger than him! She patted him experimentally across the seat of his denim jeans with her hand. 

“Aren’t you going to use the hairbrush, Celia?” asked Tommy, quizzically.

“Yes, Mr. Goodluck, but Mommy believes it’s important to always start a spanking with a warm up, before using the hairbrush. It’s in the fine print at the bottom of the chart.”

Tommy nodded enthusiastically. “Oh! Of course! I remember reading that part.”

Celia clapped the seat of Tommy’s jeans with more force, producing a steady pat-pat-pat rhythm. The sound was dense and rich, and her palm seemed to bounce off the material. Celia couldn’t help but notice that Tommy’s booty was chubby compared to his otherwise lithe frame, and it seemed to bounce like rubber at each impact.

Mr. Goodluck held himself in place stoically, easily supporting his weight on his hands and feet, which reached all the way to the floor. “Excuse me, Celia, but are you sure your mother will be happy with that? The fine print makes it quite clear that a proper spanking is supposed to hurt.”

“Don’t worry, Mr. Goodluck. This is still only the warm up,” said Celia as she switched the hairbrush to her dominant hand and raised it high. She’d been attached to this hairbrush ever since she was a child, even though it had many painful memories attached to it. Celia was eager to make a new memory with it today, her first hairbrush spanking…where she wasn’t on the receiving end!

As Celia clapped the hairbrush across his denim jeans, Tommy started to feel a prickling sensation, even through the protective layers. This wasn’t so bad. Tommy didn’t know why he had been so worried earlier. He was determined to take his licks like a man, with dignity!

“All right, Mr. Goodluck. I need you to stand up and drop your jeans!”

Tommy’s face flushed. He thought he’d read something about that in the fine print, but it had slipped his mind. “But…”

Remembering what her mother would do in this situation, Celia delivered a firm whack. “No, ‘buts,’ young man. Off my lap, and off with them!”

Tommy flew to his feet. As he fumbled with his belt, he took a furtive glance at the discipline chart on the table, making sure it did indeed call for this. It did. 

Tommy trembled. Not only did the chart call for a spanking over the underpants, it also stipulated clearly that the final twenty whacks of the hairbrush would be delivered on the bare bottom. But Mrs. Goltrode’s rules had to be followed to the letter!

Tommy slowly yanked down his jeans, struggling to get them past his wide hips, and quickly returned to his place across Celia’s lap, assuming the position for his second spanking.

Celia paused as she examined her target. “What are these? I recognize them. They look like my troll dolls!”

Tommy’s face burned red with embarrassment. “They are Trolls. They’re my lucky briefs from when I was a kid.”

Celia giggled. “Oh? They had Trolls way back then?”

Still supporting his own weight to keep in position, Tommy hunched his shoulders. He was sure Celia was going to tease him for this, like those bullies in middle school who’d pantsed him. “I’m not that old. And they’ve had troll dolls since the 1950’s. They used to call them ‘Good Luck Trolls.’”

“Well, I think it’s charming. I wear Trolls undies too, but mine have characters from the movies!”

Celia patted Tommy across the bottom with her hand again, the hairbrush lying in wait in her free hand. It was lucky Tommy was being so compliant, or she’d never have been able to hold him in place. “All right, Tommy, the warm up is over. Are you ready for the main event?”

“Yes, Miss Goltrode,” answered Tommy, accidentally slipping back into his polite manner. He’d quite forgotten that Celia wasn’t supposed to refer to him by his first name without permission, according to her mother’s rules.

Celia began the spanking again, the sounds sharper without the protective layer provided by the jeans. Just for fun, Celia aimed a few spanks at every single troll she could see on the pattern of Tommy’s underpants, before remembering to concentrate on the lower-center of his bottom, just like her mom did whenever Celia was spanked.

Tommy let out a few small grunts, finding it harder to stay still now that he could feel each sting more sharply. When Celia paused, Tommy exhaled with relief, only to feel an oval shape pressing against his rear end. Looking back over his shoulder, Tommy caught sight of the pink, plastic hairbrush. The back of the brush was not perfectly smooth. In fact, the picture of Princess Poppy’s face on the back of the hairbrush was embossed, meaning he could actually make out the texture of it. 

Celia knew from personal experience that when her mother spanked extra hard, every swat would leave a mark in the distinctive almond-shape of Princess’ Poppy’s troll haircut. Furthermore, the edges of the brush were lined with plastic diamonds that pricked with each impact. Although not as heavy as an antique wooden hairbrush, the pink Trolls hairbrush was more than enough to encourage Celia to be on her best behavior for a few days any time she felt it.

“Pop! Pop! Pop!” went the Princess Poppy hairbrush.

Tommy bit his lip, and accidentally let out a few “Ughs!” and “Oofs!” in his discomfort. Determined to make an impression that would make her mother proud, Celia wasn’t holding back an ounce of her strength. Celia repeated her process from before, landing a swat on each troll in the pattern on Tommy’s briefs, before concentrating on his lower cheeks. As the tight, childish briefs rode up his crack, Tommy’s lower cheeks poked out below, already blushing bright pink to match the hairbrush.

Celia appraised her work. No wonder Mommy spanked her so much! This was like a game. Celia always loved to carefully work on her Trolls coloring book pages until every inch of Princess Poppy’s skin was a consistent, rich shade of pink. Those skills were certainly coming in handy now! “All right, Tommy, you’re behaving yourself so far, but we’re not quite finished. Now, stand up and march over to the sofa, right now, Mister!”

Sniffling, Tommy obeyed. 

Celia gestured emphatically, just like she had seen her mother do when ordering her around. “Now, bare your bottom and lie down across the arm of the sofa. Bottoms up, little mister!”

Tommy’s courage almost failed him. He’d never been spanked before, and already every square inch of his bottom was stinging. Although he didn’t realize it consciously, Tommy had always carried a lot of guilt and self-doubt ever since he was “mamma’s little boy.” The fact that his own mother had never spanked him only made everything worse. But Tommy’s father had always told him to be brave and face adversity, so Tommy meekly lowered his briefs below his bottom and lowered himself across the sofa arm, raising his plump, feminine behind up high.

Celia sat herself primly next to Tommy on the sofa arm, and found she could aim the hairbrush blows with a wider swing of her arm from this angle, leaving fresh, rose red marks over the consistent rose pink flesh. After ten strokes, Celia rubbed the stiff muscles of her arm, before switching the hair brush to her non dominant hand. “We’re almost done, Tommy. Go to the other side of the sofa and bend over the other arm rest. I’m going to switch hands…to let my arm rest. Tee-hee!” 

Covering his front to preserve his modesty, Tommy obeyed, wincing with each step, but still refusing to cry. Celia was impressed. She knew she would have been balling after only a hand spanking over her panties.

Tommy and Celia settled themselves back into place, the final round with the hairbrush a mirror image of the previous session. But this time, Tommy finally shed two tears, burying his face in the velvety sofa cushions to suppress his cries. Celia paused, satisfied that she had done as good a job for Tommy as her mother had ever done for her. Tommy’s backside was bright red, contrasting sharply with the pale, sensitive skin of his legs. 

Sure, Tommy hadn’t broken down crying like she always did, but it wouldn’t be fair to punish him any further, just because a little mud got tracked into the house. “Good job, Tommy. You were very brave. Now, stand in the corner for timeout.” 

Tommy hissed and rubbed his bottom instinctively. 

Celia slapped him across the behind with her open hand. “Nah-ah! The rule in this house is no rubbing during timeout!”

Tommy folded his hands behind his back to keep them away from his bottom. “I’m sorry, Miss Goltrode.”

Celia couldn’t help but feel sorry for Tommy. Sure, she’d have earned a second spanking for rubbing, but since Tommy didn’t know all the rules of the house yet, Celia mercifully decided to give him a second chance. “You’re forgiven, Tommy. Since this is your first time, I can let you off with a warning! I’ll be back to speak with you after 20 minutes.”

Tommy suddenly remembered something important. “Okay, Celia, but no screen time!”

Celia froze. To be honest, she’d been tempted to take advantage of this situation to play video games, watch cartoons, and maybe even try watching a grown-up show on TV. (She didn’t know any, but the fact that she wasn’t allowed to touch the remote only made her more curious.) Celia decided not to test her luck. “Yes, sir, Mr. Goodluck!”

Celia sat and read one of her chapter books. When the clock rang 1:00, she heard a voice pipe up from the corner. “Excuse me, Celia, but I think the 20 minutes are up.”

Celia had lost track of time! “Oh! Sorry, Mr. Goodluck, I forgot. Did you learn your lesson?”

Tommy nodded, feeling a deep sense of satisfaction. “I most certainly did! I’m going to take my responsibilities much more seriously from now on! I think I finally see why your mother is such a firm believer in spanking as a method of discipline. It works wonders!”

Celia felt her stomach tense at the mention of her mother. Now that the spanking was over, it suddenly occurred to her how very easy it would be for this whole plan to backfire on her. Even if Tommy didn’t tattle on her, one casual question from Mom about the new frowny face sticker could expose all. 

But Celia decided to keep playing pretend, at least until Mom got home. After all, if Celia didn’t think about bad things that could happen, maybe they’d never happen! “Tell me, Tommy, how do you feel right now?” asked Celia, examining the mottled, red marks left by her paint job.

Tommy glanced at his bottom, and resisted the temptation to rub the sting away. “To be honest, I feel a little silly standing here. This will take some getting used to. Your mother’s rules are certainly strange.”
 
Celia giggled. “Well, I don’t think you look a bit silly, Mr. Goodluck. As a matter of fact, I think you look rather cute standing in your corner! You may get dressed and come out now! …Oh! And you may rub your bottom, if you think it will help.”

With a whistle of pain, Tommy quickly rubbed both cheeks, only to find them still hot to the touch. He winced as he felt the elastic of his tight, boyhood undies snap into place across his red rump, and finally sighed with relief as he pulled up his jeans.

Then he turned around and faced Celia, with stern, paternal authority. “Well, Celia, I hope this experience has taught you a lesson about responsibility you won’t forget!”

Celia held up one hand as she crossed her heart. “I’ve learned my lesson, Mr. Goodluck. I’ll never track mud in the house again!”

The End