"Trolling the Babysitter" (A Sweet Femboy Himbo Babysitter Gets in Trouble)
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00:00Trolling the babysitter? By you may, with contributions by Conkerfan420.
00:04Note, this fictional story depicts corporal punishment for narrative purposes.
00:08This is not an endorsement of the actions depicted.
00:12Tommy Goodluck ignored the quizzical looks from bypassers as he made his way to Mrs.
00:16Goltrode's home for his next babysitting gig. His facial features were graceful,
00:20and his figure slender, with the exception of his hips. Whenever he looked in the mirror,
00:24Tommy thought he looked like an exclamation point, narrow shoulders, narrow chest.
00:28Tommy never wore anything to look effeminate on purpose, quite the opposite. For a while,
00:32Tommy had tried wearing baggy shirts and sweaters, in a vain attempt to hide his proportions.
00:37But after Tommy had been whistled at by a man on more than one occasion,
00:40only for him to turn around and catch their annoyed befuddled look as they took a closer
00:44look at him, Tommy had concluded that no amount of modesty could hide the truth.
00:48Today Tommy was wearing a red and white striped collared shirt with blue jeans,
00:52and from behind, he was the spitting image of a young Anne Hathaway with a short boy cut.
00:56He was also wearing his lucky underpants from childhood, as was his custom whenever
01:00he took a job for a brand new client. Although no one would ever see them,
01:04having them as a good luck charm always helped Tommy start off his day off right.
01:08High school had been rough for Tommy, but it was there he'd discovered his calling,
01:11childcare. Most parents were biased against male babysitters, preferring young women,
01:16but Tommy's reputation for respecting the rules of every family he worked for,
01:20and the popularity of his famous bag of activities amongst the kids he babysat,
01:24had traveled by word of mouth. After 10 years, 24-year-old Tommy Goodluck had established
01:29himself as the top-rated babysitter in the city, and was highly sought after by yuppie parents.
01:34It was his first time in this neighborhood, an older part of town that had historically
01:37been settled by Danish immigrants. Tommy checked the pin on his smartphone map,
01:41and approached the Goltrode family home, which could have been a postcard with its red tile
01:45roof and cozy collection of wooden figurines in the garden. Mrs. Anna Goltrode was dressed
01:50in a glittering evening gown, complete with feather boa, ready for a charity lunch,
01:55followed by an afternoon at the theater. Her daughter was dressed in a simple red skirt
02:04with a black and white checkered blouse, in the tradition of their Danish immigrant forebears.
02:08Celia Goltrode pouted, it just wasn't fair, she was 10 years old, so why did she still need a
02:13babysitter? Mrs. Goltrode flicked her finger against the poster hanging on the wall of the
02:18kitchen as she stared down at her daughter. I'm giving your babysitter full permission to
02:22spank you if you misbehave. Do you understand, Celia? Yes, mother.
02:28Celia answered dutifully as she examined the dreaded poster for the millionth time.
02:32The top was labeled Duty and Discipline in large pink letters, and the chart contained
02:36quite a bit of complex information, neatly organized in columns and rows. There was a
02:40row for the five Ds which included Disobedience, Disrespect, Defiance, Dishonesty, and Danger.
02:46Under each word was a definition, followed by a list of examples and neat bullet points.
02:50Below this was a calendar for the days of the week, with smiley faces and frowny faces to
02:55chart whether Celia was meeting her mother's expectations for the week. Celia had nothing
02:59but smiley faces for the row labeled Grades and Homework, but she also had three frowny faces for
03:04Remembering to Remove Shoes Indoors. The rest of the chart was a more random mix of happy stickers
03:09with only a few frowny faces. Following the calendar was tightly written fine print and
03:14neat script defining the consequences for each offense. But thanks to the pink, plastic hairbrush
03:19hanging on the wall right by the chart, guests usually didn't have to read the chart to guess
03:23what the penalty was for getting too many frowny faces. The doorbell rang.
03:27Ah! Here is Mr. Goodluck, sang Mrs. Goldtrote in a cheerful falsetto. Celia was still feeling
03:33sorry for herself, so she didn't pay much attention as her mother explained the house
03:37rules to the new babysitter. Tommy took notes, before gesturing to the poster on the wall.
03:42Got it! Celia gets to play outside while I prepare supper. After supper, I'll clean up and will read
03:49and do indoor activities. But what about this chart? Oh! These are the house rules for what
03:55kinds of misbehavior merits are spanking. Before she could walk Tommy through every detail of the
04:00chart, Mrs. Goodluck heard the grandfather clock chime. Goodness! Look at the time! I must be off
04:07to the theater. Look this chart over when you have the time, Tommy, it's self-explanatory. So
04:13long as Celia doesn't track mud in the house again, I doubt you'll even need it. Celia's
04:19generally a very good girl. Well, I must be off. Mrs. Goldtrote patted her daughter on the head
04:25lovingly, and Celia accepted the gesture of affection. She loved her mother and knew she
04:30was loved, but Celia couldn't help but wish that just once, maybe for a day, she could be free
04:34from the dread of being one step away from a spanking. As Mrs. Goldtrote hurried to her car,
04:39Tommy called after her. Is Celia allowed any screen time? Oh, only half an hour. Thank you
04:46for asking. None of the other babysitters ever cared. Remember to be good Celia or someone is
04:53getting a spanking. Cooed Mrs. Goldtrote, rolling up the window as she pulled out the driveway.
04:58Tommy sighed. He wished he could have discussed the chart of spanking offenses with Mrs. Goldtrote
05:03in more detail, but he was confident he could figure it out. The modern suburban parents he
05:07usually babysat for generally disapproved of corporal punishment, but Tommy's motto was
05:12always to respect the rules of every family he babysat for, no questions asked. To her pleasant
05:17surprise, Celia found Tommy to be a great listener, even showing interest as she talked his
05:22ear off about her favorite doll, Poppy the Troll. Later, while Tommy read the chart carefully,
05:27he let her watch a few mini-episodes of her favorite show, Trolls, the beat goes on.
05:31When the egg timer rang to indicate that 30 minutes were up, Celia tensed, waiting for Tommy
05:36to turn off her show in the middle like other babysitters had done, but Tommy instead put the
05:40chart and timer away. I'll finish this one with you, he added as he sat down to finish the last
05:45minute of the show with her. Celia wondered if Tommy would let her get away with watching one
05:49more. These cartoons are so short. Don't you want to watch one more with me, Mr. Goodluck?
05:55They're really funny. No, Celia, your mother said your screen time is limited.
06:00Go play outside while I make lunch. Celia didn't make a fuss and played outside. Sure,
06:06her little trick hadn't worked, but maybe today wouldn't be so bad after all. Celia,
06:11lunch is ready. I've made mac and cheese with green beans. Take your shoes off and come in.
06:17Celia was so wrapped up in her own imaginary world that she didn't hear the last part.
06:21She zipped through the door and straight to the table before spotting the trail of
06:25dirty tracks she'd left across the beige carpet. Celia was horrified.
06:29I'm sorry, Mr. Goodluck. She whimpered, imagining the spanking that was surely coming.
06:34Tommy sighed, glanced at the sticker-covered chart on the wall, then fetched stain remover and towels
06:39from the kitchen cabinet. It's okay, Celia, eat your lunch while I clean this up. We'll discuss
06:44your mother's chart after you've finished eating. Celia felt like a convict on death row as she
06:49chewed her mac and cheese. One moment of forgetfulness was all it took to earn a free
06:53trip to spanking town, Lapland. And of all the days to forget, why did it have to be when she
06:58had a babysitter? And of all the babysitters, why did it have to be the only one who actually
07:02seemed cool? All the high school girl babysitters had just ignored her and fiddled with their
07:06phones. Tommy ate in silence then cleared away the dishes. Hoping he had forgotten, Celia tried
07:12to creep away to her room. Tommy spotted his charge slinking away as he untacked the poster
07:16and brought it to the kitchen table. No, Celia. We have to discuss your mother's rules.
07:22Celia hunched her shoulders as she reached the steps and turned back to the kitchen table,
07:26hanging her head. She knew there was no escape. It was spanking time. Tommy ran his finger along
07:31the calendar at the bottom of the chart. Now, Celia, as I understand this chart,
07:36you've gotten three frowny faces for tracking mud in the house this week already. According to this
07:41chart, the first frowny face is a warning. So that means someone has gotten two spankings this week
07:46already. Celia winced at the mention of someone getting a spanking, which was always her mother's
07:51favorite phrase. Why was someone always her? Why couldn't someone ever be someone else?
07:56Tommy's attention turned to the neatly written letters at the bottom, describing the appropriate
08:00punishment for each offense. And according to these rules, after getting a fourth frowny face,
08:05someone is getting a spanking with the hairbrush. Celia nodded, too ashamed to look her babysitter
08:10in the eye. Tommy scratched his scalp. Well, that part I understand, but your mother was in
08:15such a rush, I didn't have a chance to ask her any questions about the specifics of this chart.
08:20What I don't get is who this someone is supposed to be. Are you the someone this chart is referring
08:25to? Celia snapped her head up. If she wasn't so confused, she'd be in tears already. Was Tommy
08:30teasing her, dragging this out like a cat playing with a terrified mouse? He seemed so nice before.
08:35But as she examined his face, Celia thought Tommy seemed genuinely nonplussed. Uh, no? Celia shrugged
08:42as she said it, hoping Tommy would take it as a joke. Tommy activated his brain cells as he poured
08:47over the chart again, as if hoping it would come alive and speak the answer he sought. Then who is
08:51the person who's supposed to get spanked? Well, who do you think it's referring to? Tommy shrugged.
08:58That's the problem. I assumed it was supposed to be you at first, but when I read the chart,
09:02I got confused. No matter how many times I read it, it's still the same. On the one hand, Tommy
09:09rifled through his trusty babysitter backpack and whipped out an antique copy of Correction
09:13that Corrects by Miriam Frederick. I'm aware that corporal punishment has historically been favored
09:18as a method of child discipline for centuries. But, on the other hand, Tommy produced a 21st
09:23century child psychology textbook, decorated by a Norman Rockwell illustration of a mother taking
09:29a slipper to her child while examining a book on child psychology. It seems that there is also a
09:34significant body of evidence linking corporal punishment of children to various negative side
09:38effects. I don't know what to think. I've never babysat for a family that had rules for spanking
09:44before, let alone rules this complicated. Celia was stunned. For her part, Celia was so used to
09:50spanking as an inescapable aspect of her daily life, it never occurred to her she might not get
09:54spanked for tracking mud in the house. On the other hand, she felt genuinely sorry for Tommy's
09:59dilemma, but not sorry enough to tell him the answer to this riddle. Well, suppose you ask my
10:04mom when she gets home? Of course, Celia knew that her spanking would come sooner or later,
10:08but at least it could wait until bedtime. In Celia's opinion, whoever said there was no
10:13point in delaying the inevitable had never faced the prospect of being spanked. Tommy buried his
10:17face in his hands. But the rules are very clear that a spanking is to be administered immediately.
10:23Oh, if only Mrs. Goldtrode had been a bit more specific. Celia remembered every Bugs Bunny
10:29cartoon she had ever been allowed to watch, and for the first time in her life, she dared to hope
10:33for a path of escape. Well, do you think mom could have meant you? Tommy stared at the chart in horror.
10:39Me? But I've never been spanked before. And I've never met your mother before. Why would I be the
10:45someone referred to here? Well, you are responsible for me, after all. Tommy nodded. The responsibilities
10:52of babysitting were not just a job, but a sacred duty. Correct. I am responsible for you. And doesn't
10:58being responsible mean you're the one who gets in trouble if something goes wrong? Two of Tommy's
11:03brain cells had a furious argument. One brain cell had a sneaking suspicion that being spanked would
11:08be highly unpleasant, and that something was strange about this whole situation. The other
11:12brain cell was dedicated to upholding the rule of law and the code of honor for babysitters everywhere.
11:17Tommy's nobler side won the day. You're right, Celia. I'm the one responsible for upholding
11:23these rules, which means Tommy stared at the pink plastic hairbrush, which still hung from the wall
11:28menacingly. I'm the one who has to pay the penalty. But then who is supposed to administer this
11:34spanking? It's got to be done right away. Celia had a small shoulder angel sitting on her right
11:39shoulder, pleading with her to face the music. But then her shoulder devil started playing a
11:43golden banjo, and Celia decided to go for it. I suppose I could spank you, Mr. Goodluck. I know a
11:49lot about it. Mr. Goodluck froze before wiping a bead of sweat from his brow in relief. Would you?
11:56Oh, thank goodness. I was afraid I wouldn't be able to follow your mother's rules to the letter.
12:01But I don't know how this works, Celia. Don't worry, Mr. Goodluck. I'll walk you through it
12:07step by step. First, would you please help me reach the hairbrush? As Tommy took the pink plastic
12:13hairbrush from the hook, he realized it was decorated with an engraved image of Princess
12:17Poppy from the original Trolls film. The paint slightly faded after years of loving use. In that
12:22time, Mrs. Goldtrode had practically worn out the hairbrush on her daughter by wearing out her
12:27daughter with the hairbrush. Celia dragged her mother's high-backed chair into the center of the
12:31kitchen, hopped up to seat herself on it, and held out her hand to accept the hairbrush. Now, Mr.
12:36Goodluck, you want this spanking to be exactly like my mother's rules for the house, correct?
12:41Tommy nervously handed over the implement. Ever since he was a kid, people had called him a wimp
12:46and much meaner names. What if he couldn't take a spanking? Of course, Celia. In that case,
12:51lie carefully across my lap. It may sting a bit, but if you're brave and hold still,
12:57we can get this over quickly. As Tommy settled into place across Celia's lap, she was struck by
13:02how lightweight he was. In a few years, Celia thought she might be stronger than him. She
13:07patted him experimentally across the seat of his denim jeans with her hand. Aren't you going to
13:11use the hairbrush, Celia? asked Tommy quizzically. Yes, Mr. Goodluck, but Mommy believes it's
13:17important to always start a spanking with a warm-up before using the hairbrush. It's in the
13:22fine print at the bottom of the chart. Tommy nodded enthusiastically. Oh, of course. I remember
13:29reading that part. Celia clapped the seat of Tommy's jeans with more force, producing a steady
13:34pat-pat-pat rhythm. The sound was dense and rich, and her palm seemed to bounce off the material.
13:40Celia couldn't help but notice that Tommy's booty was chubby compared to his otherwise lithe frame,
13:44and it seemed to bounce like rubber at each impact. Mr. Goodluck held himself in place
13:49stoically, easily supporting his weight on his hands and feet, which reached all the way to the
13:53floor. Excuse me, Celia, but are you sure your mother will be happy with that? The fine print
13:59makes it quite clear that a proper spanking is supposed to hurt. Don't worry, Mr. Goodluck.
14:04This is still only the warm-up, said Celia as she switched the hairbrush to her dominant hand
14:09and raised it high. She'd been attached to this hairbrush ever since she was a child,
14:13even though it had many painful memories attached to it. Celia was eager to make a new memory with
14:18it today, her first hairbrush spanking, where she wasn't on the receiving end. As Celia clapped the
14:23hairbrush across his denim jeans, Tommy started to feel a prickling sensation, even through the
14:27protective layers. This wasn't so bad. Tommy didn't know why he had been so worried earlier.
14:32He was determined to take his licks like a man, with dignity. Alright, Mr. Goodluck. I need you
14:38to stand up and drop your jeans, Tommy's face flushed. He thought he'd read something about
14:43that in the fine print, but it had slipped his mind. What? Remembering what her mother would do
14:47in this situation, Celia delivered a firm whack. No, butts, young man. Off my lap, and off with
14:54them. Tommy flew to his feet. As he fumbled with his belt, he took a furtive glance at the discipline
14:59chart on the table, making sure it did indeed call for this. It did? Tommy trembled. Not only did the
15:05chart call for a spanking over the underpants, it also stipulated clearly that the final 20
15:09whacks of the hairbrush would be delivered on the bare bottom. But Mrs. Goldtrode's rules had to be
15:14followed to the letter. Tommy slowly yanked down his jeans, struggling to get them past his wide
15:19hips, and quickly returned to his place across Celia's lap, assuming the position for his second
15:23spanking. Celia paused as she examined her target. What are these? I recognize them. They look like
15:30my troll dolls. Tommy's face burned red with embarrassment. They are trolls. They're my
15:36lucky briefs from when I was a kid. Celia giggled. Oh, they had trolls way back then? Still supporting
15:43his own weight to keep in position, Tommy hunched his shoulders. He was sure Celia was going to tease
15:47him for this, like those bullies in middle school who'd pantsed him. I'm not that old, and they've
15:52had troll dolls since the 1950s. They used to call them good luck trolls. Well, I think it's charming.
16:00I wear trolls undies too, but mine have characters from the movies. Celia patted Tommy across the
16:05bottom with her hand again, the hairbrush lying in wait in her free hand. It was lucky Tommy was
16:10being so compliant, or she'd never have been able to hold him in place. All right, Tommy, the warm-up
16:16is over. Are you ready for the main event? Yes, Miss Goldtrode, answered Tommy, accidentally slipping
16:22back into his polite manner. He'd quite forgotten that Celia wasn't supposed to refer to him by his
16:26first name without permission, according to her mother's rules. Celia began the spanking again,
16:31the sound sharper without the protective layer provided by the jeans. Just for fun,
16:35Celia aimed a few spanks at every single troll she could see on the pattern of Tommy's underpants,
16:40before remembering to concentrate on the lower center of his bottom, just like her mom did
16:44whenever Celia was spanked. Tommy let out a few small grunts, finding it harder to stay still
16:49now that he could feel each sting more sharply. When Celia paused, Tommy exhaled with relief,
16:54only to feel an oval shape pressing against his rear end. Looking back over his shoulder,
16:58Tommy caught sight of the pink, plastic hairbrush, the back of the brush was not
17:02perfectly smooth. In fact, the picture of Princess Poppy's face on the back of the
17:07hairbrush was embossed, meaning he could actually make out the texture of it. Celia knew from
17:11personal experience that when her mother spanked extra hard, every swat would leave a mark in the
17:16distinctive almond shape of Princess Poppy's troll haircut. Furthermore, the edges of the brush were
17:21lined with plastic diamonds that pricked with each impact. Although not as heavy as an antique
17:25wooden hairbrush, the pink troll's hairbrush was more than enough to encourage Celia to be on her
17:29best behavior for a few days anytime she felt it. Pop pop pop, went the Princess Poppy hairbrush.
17:35Tommy bit his lip, and accidentally let out a few
17:38Uggs
17:38and
17:39Oofs
17:40in his discomfort, determined to make an impression that would make her mother proud.
17:44Celia wasn't holding back an ounce of her strength. Celia repeated her process from before,
17:48landing a swat on each troll in the pattern on Tommy's briefs, before concentrating on his
17:52lower cheeks. As the tight childish briefs rode up his crack, Tommy's lower cheeks poked out below,
17:58already blushing bright pink to match the hairbrush. Celia appraised her work. No wonder
18:03mommy spanked her so much, this was like a game. Celia always loved to carefully work on her troll's
18:08coloring book pages until every inch of Princess Poppy's skin was a consistent, rich shade of pink.
18:13Those skills were certainly coming in handy now.
18:16Alright, Tommy, you're behaving yourself so far, but we're not quite finished.
18:21Now, stand up and march over to the sofa, right now, mister.
18:25Sniffling, Tommy obeyed. Celia gestured emphatically, just like she had seen her
18:29mother do when ordering her around. Now, bare your bottom and lie down
18:33across the arm of the sofa. Bottoms up, little mister.
18:37Tommy's courage almost failed him, he'd never been spanked before, and already every square
18:42inch of his bottom was stinging. Although he didn't realize it consciously, Tommy had always
18:46carried a lot of guilt and self-doubt ever since he was mama's little boy. The fact that his own
18:51mother had never spanked him only made everything worse, but Tommy's father had always told him to
18:55be brave and face adversity. So Tommy meekly lowered his briefs below his bottom and lowered
19:00himself across the sofa arm, raising his plump, feminine behind up high. Celia sat herself primly
19:06next to Tommy on the sofa arm, and found she could aim the hairbrush blows with a wider swing of her
19:10arm from this angle, leaving fresh, rose-red marks over the consistent rose-pink flesh.
19:15After ten strokes, Celia rubbed the stiff muscles of her arm, before switching the
19:19hairbrush to her non-dominant hand. We're almost done, Tommy. Go to the other side of the sofa
19:25and bend over the other arm rest. I'm going to switch hands, to let my arm rest. Tee hee.
19:32Covering his front to preserve his modesty, Tommy obeyed, wincing with each step, but still refusing
19:38to cry. Celia was impressed, she knew she would have been bawling after only a hand spanking over
19:43her panties. Tommy and Celia settled themselves back into place, the final round with the
19:47hairbrush a mirror image of the previous session. But this time, Tommy finally shed two tears,
19:52burying his face in the velvety sofa cushions to suppress his cries. Celia paused, satisfied
19:58that she had done as good a job for Tommy as her mother had ever done for her. Tommy's backside was
20:03bright red, contrasting sharply with the pale, sensitive skin of his legs. Sure, Tommy hadn't
20:08broken down crying like she always did, but it wouldn't be fair to punish him any further, just
20:12because a little mud got tracked into the house. Good job, Tommy. You were very brave. Now, stand in
20:19the corner for timeout. Tommy hissed and rubbed his bottom instinctively. Celia slapped him across
20:24the behind with her open hand. Nah-ah. The rule in this house is no rubbing during timeout. Tommy
20:31folded his hands behind his back to keep them away from his bottom. I'm sorry, Miss Goldtrode. Celia
20:36couldn't help but feel sorry for Tommy. Sure, she'd have earned a second spanking for rubbing,
20:41but since Tommy didn't know all the rules of the house yet, Celia mercifully decided to give him
20:45a second chance. You're forgiven, Tommy. Since this is your first time, I can let you off with
20:51a warning. I'll be back to speak with you after 20 minutes. Tommy suddenly remembered something
20:56important. Okay, Celia, but no screen time. Celia froze? To be honest, she'd been tempted to take
21:03advantage of this situation to play video games, watch cartoons, and maybe even try watching a
21:07grown-up show on TV. She didn't know any, but the fact that she wasn't allowed to touch the remote
21:12only made her more curious. Celia decided not to test her luck. Yes, sir, Mr. Goodluck. Celia sat
21:19and read one of her chapter books. When the clock rang one o'clock, she heard a voice pipe up from
21:23the corner. Excuse me, Celia, but I think the 20 minutes are up. Celia had lost track of time. Oh,
21:30sorry, Mr. Goodluck, I forgot. Did you learn your lesson? Tommy nodded, feeling a deep sense of
21:36satisfaction. I most certainly did. I'm going to take my responsibilities much more seriously from
21:42now on. I think I finally see why your mother is such a firm believer in spanking as a method of
21:48discipline. It works wonders. Celia felt her stomach tense at the mention of her mother.
21:53Now that the spanking was over, it suddenly occurred to her how very easy it would be for
21:57this whole plan to backfire on her. Even if Tommy didn't tattle on her, one casual question from mom
22:02about the new frowny face sticker could expose all. But Celia decided to keep playing pretend,
22:07at least until mom got home. After all, if Celia didn't think about bad things that could happen,
22:12maybe they'd never happen. Tell me, Tommy, how do you feel right now? Asked Celia, examining the
22:18mottled red marks left by her paint job. Tommy glanced at his bottom and resisted the temptation
22:23to rub the sting away. To be honest, I feel a little silly standing here. This will take some
22:28getting used to. Your mother's rules are certainly strange. Celia giggled. Well, I don't think you
22:35look a bit silly, Mr. Goodluck. As a matter of fact, I think you look rather cute standing in
22:40your corner. You may get dressed and come out now. Oh, and you may rub your bottom if you think it
22:47will help. With a whistle of pain, Tommy quickly rubbed both cheeks, only to find them still hot
22:52to the touch. He winced as he felt the elastic of his tight boyhood undies snap into place across
22:57his red rump and finally sighed with relief as he pulled up his jeans. Then he turned around and
23:02faced Celia with stern paternal authority. Well, Celia, I hope this experience has taught you a
23:07lesson about responsibility you won't forget. Celia held up one hand as she crossed her heart.
23:12I've learned my lesson, Mr. Goodluck. I'll never track mud in the house again.
23:18The end. Spanks for watching. If you'd like to commission a short story, contact me on
23:24X or DeviantArt. You may spank it once.