The Best Babysitter in Town (Chapter 3 posted 6/3/22)

Hello everyone,

This is the first chapter of my latest story. This is currently being published chapter by chapter on my Patreon and will be available in its entirety later this year. You can find the latest chapters at patreon.com/alex_bridges.

All characters are 18+


Chapter 1

It’s not like I did it on purpose. I’m not sorry, but it’s not like I did it on purpose. I babysit three times a week on average, more like five times in the summer. I want to pay for as much of college as I can in cash, and childcare pays better than retail or waiting tables. Especially now that schools keep opening and closing, parents are desperate for a night away. For me, an opportunity to make more money, which I need. I’m not going to risk my reputation as the best sitter in town just because of a little mix up.

“Hi, Mrs. Rooney,” I said when she opened the door.

“Hi, Sally. Come on in. Thanks for coming over on short notice.” I followed her into her kitchen; the Rooneys always have good stuff in the fridge. I didn’t get where I am as a sitter by abusing fridge privileges, but I don’t pass up the benefit either. She was dressed to the nines. I never asked, but it always seemed like she and Mr. Rooney must be going someplace expensive. Just based on their house alone, they must be one of the richer families I sit for. They’re not wealthy, but they got the upper-middle-class thing down pat. Literally the only people I know whose entryway it an actual room.

“Always happy to when I can,” I replied, “I like Jamie and Jackie.” Well behaved kids, easy to get along with.

“O, they’re both at friends’ houses tonight. It’ll just be you and Gordy tonight. Is that okay?” Like I couldn’t tell this ‘misunderstanding’ was totally on purpose. She had this guilty, pleading look on her face, but that was so beside the point.

“Gordon? Really?” I knew Gordon. More specifically, I’ve known him since kindergarten, which would make fourteen years we’ve known each other. We graduated a little over year ago in the same class; we were even in the same twelfth grade homeroom, and now we’re both sophomores townies at the same college. I’ve sat for the Rooneys more than a few times, and Gordon was, obviously, never one of my charges. I just figured that was because he was the same age as me. Come to think of it, he was never even home when I sat for the kids because if he was, why would they need me to watch the kids?

“I wouldn’t ask. Normally he spends the night at my sister’s or a friend’s house when you’re over, but he can’t tonight.”

Like, but he’s … “But why does he need a sitter? He’s twenty. He’s, like, a month older than me, right?” And I’m also twenty.

“Yes, but I don’t like leaving him alone if it can be helped.”

“O … kay. So we’ll just watch a movie, I guess.” Get paid a hundred bucks to watch a movie with one of my peers? Weird, but fine by me. We’re not friends exactly, but we’re friendly. We were sorta friends when we were younger, but less so once we got to middle school. Gordon’s not exactly Mister Popular. Everyone’s nice to him, though, and he seems nice enough too. Just … different crowds.

“Not exactly. I can explain fast, but we’re running late.”

“That’s fine. I’ll stay.”

“O, thank you. We just really need a night out, and since he got in trouble on campus today, he’s not allowed to go to his friend’s house and my sister already had plans and …”

Didn’t really need her life story. “Whatever. It’s fine. Just tell me what’s up,” I said with a dab of false cheer to cover my WTF. She’s running late; I’m getting paid whether she tells me all this other stuff or not, so hey, let’s skip to the part I need to know, right?

“Gordy,” Mrs. Rooney said, “come sit at the table with us. I want you to hear all of this so you can’t say you didn’t know later.” I followed her eyes, and color me surprised to see Gordon – Gordy at home, apparently; he always hated being called that in school – standing in the corner in his pajamas at six o’clock. I know the difference between lazy around-the-house-clothes and jammies, and those were definitely jammies. He shuffled over blushing all the way to his ears as he kept his eyes pointed at the floor.

We all took a seat at the table. I couldn’t tell if he as about to cry, tantrum, or both, and I wouldn’t blame him if he did. If I were him, I’d probably have broken something and peeled out of the driveway while flipping the bird. I mean, we’re not kids. We’re not even teenagers. We’re way too old for a babysitter by about eight years.

“First off,” Mrs. Rooney said, “do you know about Gordy’s issue?”

“His diapers? Yeah.” Like he could keep that a secret for since literally the entire time I’d known him. No one made fun of him for it, not in a long time. Kindergarten and maybe first grade a little, but even in kindergarten it quickly became normal: our class had a kid in diapers. An adult in diapers now. And he’s not on the spectrum or delayed or anything. I don’t know what the issue is cuz it’s none of my business, but he’s always been in diapers, at least so far as I know. You’d have to be dense to have not figured it out within the first week of kindergarten. And if even if you were dense, when we got to middle school and had to change for gym, I think they let him change in a private stall or something, but you could totally hear him crinkling through those shorts. And no one teased him. Gordon wears diapers, always has; he went to the nurse a couple times a day, and we all knew why. If anything, people in school were kind of protective of him even though he didn’t need it. I even heard a rumor that when a new kid asked about it in tenth grade, the biggest bully in our class hauled off and punched him just to make it perfectly clear no one bullies Gordon.

“You’ll need to check and change him tonight.” Just when I thought Gordon – well, when in Rome – Gordy couldn’t bow his head any lower.

“Uh, he doesn’t do that himself? Or can’t he?” You don’t get to be the most sought-after babysitter in town by being squeamish about changing diapers, but one fact I do know: toddlers make bigger messes than newborns, and twenty-year-old Gordy has about a hundred and five pounds on the average two-year-old. Though come to think of it, I didn’t know if Gordy needed diapers for that or just for wetting accidents. In the brief second I had to consider that, it occurred to me even a toddler who still has wetting accidents is usually in a pull-up, not a full blown diaper. Our school’s gym shorts covered everything, but there was no mistaking Gordy’s underpants for a pull-up. He wears diapers.

“Gordy got a diaper rash last week. If he wants the privilege of changing his own diapers, he needs to be responsible about it, which means no rashes. I’m sorry to even ask you to change him, but I like to be very consistent with the rules, and the rule is if he gets a diaper rash, no changing his own diapers for a month.”

Not surprised exactly. She’s one of the stricter parents I sat for. So yeah, she’s his stepmom, but she’s not really an evil stepmom. She’s just a stickler for rules. I was afraid to ask this and very sorry to have to ask it in front of Gordy, poor little guy, but I had to. “Um, does he … both ways?” I guess I could’ve asked him, but he seemed like he’d rather have a hole swallow him than answer any questions.

“He doesn’t usually have a dirty diaper in the evening.”

“Still …”

“Two hundred for the night,” Mrs. Rooney said before I could finish the sentence we both knew I was in the middle of saying.

“Two-fifty.” Hey, I’m not one to miss an opportunity. Do you know what books cost for just one semester?

“Done.”

“Sorry,” I said under my breath to Gordy. I felt bad enough for him that she was making him have a sitter, but how much worse for him to hear what it costs to get someone to look after him, which he doesn’t want anyway, and pretty obvious why anyone would want extra to sit for him. So yes, I felt bad for him, but it’s just … the ‘usually’ in ‘doesn’t usually have a dirty diaper in the evening’ sorta stands out like sore thumb in that sentence, right? It would if you were me, and I am me.

“And another thing,” Mrs. Rooney said.

“Mommmm,” he whined. A little spark of rebellion flashed in his eyes. I didn’t know about what, but that’s what you expect from someone his age. I guess I understand if life’s circumstances made him a little more likely to give in than lash out even when any of the boys we graduated with most of the girls would’ve told their stepmom where to go by now.

“Gordon, last warning.” I looked from her to him, and that little spark turned into a little water, and he looked back down at the table. “As I was saying, Gordon got in trouble on campus today and is grounded, so he’s not spending the night at a friend’s like he normally does. Why don’t you tell the story, Gordy, since you think you’re old enough to say anything you want?” Did I say ‘stepmom’, cuz I meant ‘bitch.’ And Mrs. Rooney is not normally a bitch, so that got me more than a little curious what exactly he’d done to piss her off so mightily. On top of which, it’s not exactly easy to get in trouble on campus. I mean, we’re adults. You can do some seriously stupid stuff on campus without getting in trouble.

He sighed and answered, “I called called someone … a name.”

“The ‘C’ word,” his stepmom clarified. Or should I say his very reasonable, no more pissed off than she had a right to be (but could still be a whole lot more chill and even more thoughtful) stepmom clarified. “Gordy actually called a woman the ‘C’ word.”

“But she …” Gordy tried to defend his actions.

“I know what she said, and you had every right to be angry with her, but that is not how you talk to or about women. You know that, and losing your temper is not an excuse for using a slur.” She turned back to me. “I already washed his mouth out, but that language also earned him a bedtime spanking.”

“A sp … O … kay.” Of all the ways my day could’ve gone, didn’t see this one coming. Like, at all. I personally never got why some parents get so bent out of shape about bad words (how bad can they be when you can turn on network TV and hear most of them?), and I didn’t really get why she cared given that – did I mention it six times already? – Gordy is twenty years old.

On the other hand … now I understood why Mrs. Rooney was taking it so seriously. It’s not that big a deal if you think of the ‘C’ word as a swear, but if you think of it as a slur, yeah, much bigger deal. I guess it depends on how you use it, cuz I could see how it could be a slur, but I’ve always thought of it more as a swear. Not that my opinion meant anything in the circumstances. I’m the babysitter – I literally just work here.

“I’m too old,” Gordy interjected probably (more like definitely) more loudly than someone in his position should’ve. I mean, I agree with him, but he still should’ve just kept quiet. There’s standing up for yourself, and then there’s digging the hole deeper. If she had already washed his mouth out (ick!), not let him go out with friends, and hired a sitter for him, I couldn’t imagine any argument, not matter how obviously valid, changing her mind.

Mrs. Rooney is a fit woman; I’ve seen her play a heckuva game of tennis at the club, so not a surprise she could be on her feet and have her stepson by the ear so damn fast. Gordy’s not the first kid I’ve gone to babysit and found standing in a timeout; or the first kid I’ve gone to sit and seen spank-marched to the nearest corner for corner time; or even the first kid I’ve sat for who earned a spanking on my watch. But he was the first kid I’ve sat for who wasn’t, ya know, an actual kid. He may have crinkled all the way to the corner; he may have eeped a little when she tugged his ear; he may have tried to get out of the way of her hand as she delivered those underhand spanks; and he may even be kinda cute in a boyish kind of way, but definitely an adult. One whose birthday actually comes before mine. Diapered or not, adult.

“Not another word,” Mrs. Rooney warned him, “or I’ll take your pants down right here. You just stand there and listen.” And damn did she mean it, even in evening wear. That tone? Enough to make me almost jump out of my chair to find my own corner and listen.

“Are we ready, honey,” Mr. Rooney asked as he appeared from somewhere. Not that I wanna be that babysitter, but Mr. Rooney can take me anywhere so long as he’s wearing his tux. Shawl collar? Makes him seem even taller. No mistaking him for your waiter. And who even goes places that are black tie?

“Just a minute,” Mrs. Rooney replied and picked up the pace; they probably had a reservation at one of those places you have to reserve six months ahead of time. Anyway, she continued quickly with, “He takes a bath on Fridays, not a shower. When he gets out of the bath, please give him his spanking. His diaper comes down, and he goes over your knee. He knows where to the hairbrush is. Then it’s straight to bed. Lights out at 9:30. That means no dawdling in the tub, Gordy. Out at 9:15. Understood?” He either understood or he didn’t want to risk saying anything he had every right to say but shouldn’t unless he wanted two spankings in one day. “Any questions,” she asked me.

“So … on his … bare?”

“Have you ever given a spanking before?”

“Yeah … Well, a swat on their reset button,” I said, oddly embarrassed. I mean, most parents don’t even spank anymore, let alone allow – let alone ask! – a sitter to do it. I’ve tapped a tantruming toddler on the bottom before, but that’s not even a spanking.

“Are you okay doing it? I wouldn’t ask, but the rule is a bedtime spanking. It’s best for them to get their consequence as soon as possible, and Gordy really needs the structure.”

I guess that was all Gordy could take. “But she can’t! She’s the same age as me!”

There was silence as Mrs. Rooney turned and looked at him like he was out of his mind. I thought he was in his exact right mind, but if I had to live with her, always strict like she is and and just then downright exuding this weird kind of determined, calm-but-pissed-off vibe she was giving off, I think I’d have kept my mouth shut. I think he realized that too cuz he didn’t say anything else or turn around. So that was two outbursts (justified if unwise) since I’d gotten there plus calling someone the ‘C’ word all in one day. Talk about your verbal incontinence.

I don’t feel very strongly about spanking one way or the other. It didn’t do me any harm – though the last one I got was in third or fourth grade, and it was pretty rare before then too – but I’m not one of those crazy people who thinks you can’t possibly raise godly tomatoes (or whatever asinine phrase the bible bunch uses) without it. Still, I was the babysitter. It’s kind of my critical to my job to not let “you’re just the babysitter so you can’t XYZ” slide. On the one hand, pick your battles. On yet another hand, some battles you gotta fight.

So I got up and connected that hand hard with Gordy’s butt. “I’m the babysitter. I’m in charge. And if your stepmom says you’re getting a spanking, you’re getting a spanking.”

Two bonuses to stepping up like I did. First, and this wasn’t the main thing but was intentional, Mrs. Rooney smiled thinly and stood up, not to follow up on her threat to spank Gordy but to leave. Good riddance. Who needs those vibes around?

Second, unintentional bonus: holy crap did I feel more powerful than I ever have in my life. And turned on. My promise ring didn’t make the journey from youth group to my mom’s car, but never I felt the way I did right then without a D or a D-cell battery before.

Downside? Gordy finally lost it and started sniffling. I know the two spanks I landed didn’t actually hurt through his diaper, but I’m sure he was feeling about two inches tall having his college classmate spank him on his diaper while telling him she could and would give him a real spanking later that same night. I hated that I made him feel that way, even if I was just his stepmom’s instrument in this case. But also, and I feel guilty for saying this, it kinda added to the whole arousal hearing him sniffle. So … there’s a thing I learned about myself that night.

Mrs. Rooney said to me, “I think you’ll do fine, but if you have any questions, Gordy will answer them. Not his first trip over a knee.”

“Another fifty.” Did I say that? Good for me!

“That’s fair. Edward,” she called out to wherever Mr. Rooney had gone, “ready when you are.” To me she said, “Thank you again and sorry for all the fuss. I didn’t want to call just anyone over. I trust you. He may not want you here, but I told him you’d keep everything between us, won’t you?”

“Of course.” Also, ‘may not?’ Try resented the hell out of it, understandably so. And I resented the hell out of her asking me to sit and springing this on me.

“We’ll be home very late.”

“I know. I’ll probably be asleep on the couch when you get home.”

I stood against the doorframe and watched Mr. Rooney count out three hundred dollars and put it next to the pizza money. I told them to have fun. She called me a godsend and barely avoided the door hitting her on the butt on the way out.

To my right, Gordy in the corner, no longer sniffling but still staring at the wall on his naughty spot.

To my left, three hundred dollars on the counter just for spanking and diapering a grown man. If I’d only known about this cottage industry sooner! Heck, I’d have paid off my car by now.


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Here is Chapter 2. You can find the complete story at patreon.com/alex_bridges


Chapter 2

I waited to hear the garage door close for probably a couple seconds longer than it should’ve taken to realize I didn’t hear the garage door open, and no surprise given the size of the Rooney McMansion. I just wanted to make sure Mr. and Mrs. Rooney were gone before I turned my attention back to Gordy.

“I am so sorry,” I said as I crossed the kitchen in three big steps. It was a very confused Gordy that I turned around and hugged. Didn’t even occur to me a hug was kind of invasive, but maybe I’d already internalized that it was doing to be the least invasive physical contact we’d be having that evening.

“I am so sorry. Are you okay?” I mean, this was Gordy! Don’t be mean to Gordy is just a rule. Like he doesn’t have enough crap to deal with never getting out of diapers without his peers giving him a hard time. I’d known him since kindergarten, and his stepmom was just out of line. He was twenty! We both were, but I was the babysitter … And he was the babysat. He didn’t need a babysitter, he should be allowed to change his own diapers, and he’s way too old for a spanking! But even if his stepmom disagrees, and clearly she did, her being royally pissed off for calling someone the ‘C’ word didn’t justify embarrassing him the way she did by having me over and asking me to do it. I knew she was strict, but I didn’t think she was, well, a ‘C’ word herself until that night. I mean, I didn’t know the whole story, and what a saga it must be, but that’s how she came off.

“What,” the clever boy said and who can blame him for having a little whiplash considering a minute and a half had passed since I’m silenced his protest with a spank on the butt.

“For you having to sit through that …” My turn to blush. “And the spanks. I didn’t want to, but … Are you okay?”

“Um, yeah.”

I took one look in his eyes. “No, you’re not. You poor thing. Go sit down in the family room. I’ll order the pizza and be there in a sec. What do you want to drink?”

“A coke. I can get it.”

“Shoo. I’ll be right there.” Was I being sort of ridiculously nice because I felt bad for him? Yes. Because I felt guilty for swatting him on the butt, even though it couldn’t have hurt through his diaper? Yes. Because I felt extra super guilty for how it turned me on? Hell yes.

And maybe also because of how awkward I felt, which was only getting worse as the reality of the situation set in? Super goddam yes. I watched him in his jammies walking toward the living room, and thinking that I’d be diapering and spanking that butt in the next few hours was definitely weird, to understate if dramatically.

I ordered dinner and made two cokes, and my normal babysitter brain reminded me kids who wear diapers to bed don’t get caffeine in the evening before correcting itself. Not normal babysitting. I found him on the couch wearing the saddest puppy dog face I’ve ever seen on someone over the age of twelve and felt like I owed it to him as a friend, and babysitter, to cheer him up or at least try to. His stepmom may be pissed at him, but I wasn’t. No good reason why we couldn’t at least try to have a good time despite, well, we could at least try. What’s the point of being twenty if you can’t ignore consequences as far away as three hours?

“Hey,” I said as I sat down next to him and handed him his coke, “Cheer up. I won’t tell anyone.” Though like that even half the point. He took his glass without looking at me. Commiserating sometimes works to cheer up my usual babysitting charges, so why not give it a shot? “Your stepmom is kind of a bitch, huh?” Had the added benefit of being true.

That got some engagement. “Yeah, sometimes.”

“Just sometimes? Cuz if I were you …” Probably shouldn’t have said that. I’m not him. Doubt he wanted to hear what a twenty-year-old classmate who got out of diapers at age two and hasn’t been spanked since age eight would do in his shoes. Our shoes don’t come from remotely the same place. “Anyway, you wanna tell me what happened?”

“Not really.” He took a drink.

“Might make you feel better.”

He took another drink. “I … This girl I asked out, she … She made fun of me.” He asked someone out? Brave. Respect.

“What did she say?”

“I …”

“Was it about your diapers?” He jerked his head in a nod and took another swallow. I’d have told him to go easy, but like it would make a difference. “How did she even know?”

“I don’t know. It’s just … Been a long time since anyone made fun of me for it. Didn’t think I’d have to deal with that now that I’m an adult.”

“Is it true Kyle Berman punched Billy Kosterson in tenth grade just for asking if you wear diapers?”

“Yes.” He rolled his eyes. “Like it did me any favors.”

Probably shouldn’t have said this, but, “As cruel as kids can be, I think you were kind of lucky. I mean, I always thought people didn’t really make fun of you. It was kind of a rule that no one made fun of you. Better than the opposite, right?”

“I just want to be treated normal.”

“You’d rather people had made your life miserable all through school? Much better to have Kyle sticking up for you than be on his receiving end.”

“Yeah, but … no. Kinda.”

“So what did this girl do exactly?” Back to the present.

“I … It’s embarrassing.”

“You and I aren’t going to have a lot of secrets left by the time you go to bed.” Well, I will.

“I asked her out. After class. I just asked if she wanted to get Starbucks sometime and she just … she laughed at me.”

“What a bitch!”

“Huge bitch! And then she posted about it on TikTok and called me … diaper boy. So god knows how many people I know found out … And then on campus today I saw her and she and friends started laughing at me and I tried to ignore them but … I lost my temper and called her …”

“A cunt? Cuz that’s a seriously cunt thing to do.” I’d have called her a cunt. I’d have called her friends cunts. I mean, yeah, that’s a fucking ugly word but what she did was even uglier. If ever that word applied to someone … I was hoping my saying it would at least make him smile, but nope. “So how did that get you in trouble on campus?”

“She fucking … I can’t even believe this. One of her friend’s moms knows my stepmom.”

“Seriously?” He got tattled on? Like, fucking seriously? “Did you get to tell your side of it?” Like he should even have to justify himself, even if he were in the wrong.

“Yeah, and she still … She said it’s a slur and what if someone filmed it? It would always be out there. I said she was being totally unreasonable and unfair but she … Anyway.” He started out with a rush of indignant words and trailed in resignation.

Talk about having one of the worst days of your life. “Sorry. If it makes you feel any better, I think you’re right, those girls are horrible, and your stepmom is wrong.” I swear I saw a little light bulb go off over his head.

“So,” he tentatively asked, “since you don’t think I did anything wrong and that my stepmom is being ridiculous, does that mean …”

“Nope. Sorry.”

“Come on,” he whined more than demanded.

“Sorry.”

“But why!?!” Okay, that was a demand. And not that I didn’t see his point, but I had to think of myself too. A spanked butt and wounded pride will heal, but student loans are forever (no matter what the loan agreement says). True story.

“Hey,” I said firmly but didn’t raise my voice, “Don’t cop an attitude with me. We can still have a fun evening.” Which is when he looked at me like I was crazy; can’t blame him.

“Not really,” he said like it was pretty obvious that no, it would definitely not be a nice evening, at least not for both of us. “Just tell her you did everything she said. Please? How is she gonna know?”

“Is your stepmom going to change your diaper in the morning? Is she going to see your butt?”

“O … yeah.”

“So you’ll probably get an even worse spanking when she finds out you wiggled your way out of your consequence, and she’ll probably blab to everyone that I’m not trustworthy.” I would’ve expected a twenty-year-old, heedless as we are about the future sometimes, to see ahead twelve hours to how that would play out, at least for him. I mean, I don’t expect him to care about what it meant for me, but in his very unique circumstances within his other very unique circumstances, she’d find out.

“Yeah …”

“But we can still have a nice time. Does it seem like I care that you still get spanked and that she hires a babysitter for you?”

“You’re getting paid for it.” Little bit of acid in that remark. Also fair. I’m nothing if not a fair babysitter.

“Okay, fine. Half of it’s yours.”

“Really?”

“Yeah. Spend it on whatever you want. You want to have a two hundred copies made with her picture and the ‘C’ word on it, goo put clothes on and we can go to Kinko’s right now.”

“Heh. Thanks.”

“There’s a smile.” I reached over and nudged his shoulder. “Dinner is going to be here in a couple minutes. Need a diaper change?”

“Um … no.”

“That ‘um’ is a little suspicious,” I tried to say in a way that lightened the mood for what I was about to ask. “Mind if I check?” And it wasn’t really a question. I sat up and leaned toward him, and he reared back like he’d been bit by something. In my experience, it’s not that hard to get boys to do what you want, at least at our age. They’re actually better able to resist our entreaties at about half our age. I made my best disarming smile and tried in as charming a tone as I could without resorting to my come-hither voice to say, “Don’t be silly. You don’t wanna sit in a wet diaper, do you?”

I’ve checked a lot of diapers, and I tried to tell myself this was no different as I put my hand on the outside of his jammies while he blushed fire engine red. “Hold still,” I said as gently as I could and with my left hand pulled back the waistband of his pajama pants and with my right, reached down to put two fingers inside the leg gather between his thighs. That’s how you check a diaper, and he was wearing a diaper so … I know it was more awkward for him than me, but hey, maybe not. He certainly opened his legs when I out my hand in his pants, probably a reflex by now. It was my first time checking an adult in a diaper, but it for sure wasn’t his first time. It wasn’t even his first time getting checked by someone other than his stepmom. I felt for him, but he could also lighten up a bit.

“You’re wet, but it can wait until after dinner. Unless you’re uncomfortable; I can change you now if you want.”

“I’m … fine. And I can do it myself. You don’t have to.”

“Gordy,” I said and saw him grimace a little at my firm-but-patient tone. “Sorry, Gordon. I’m not trying to be mean, but let’s just get this out of the way. I’m the most popular babysitter in a town for a reason. It’s my job. I’m going to do what I told your stepmom I’d do.” O my goodness, what a sad face he made. “But,” I said because every experienced babysitter knows about carrots and sticks, “if you cooperate and be a big boy about it, you can stay up til 11:30.”

“Did you just call me a …”

“Sorry. Figure of speech.” Really. But now that I’d said it, also not uncalled for. He got in trouble; he knows what consequences he gets; and the most mature thing he could do, short of calling his stepmom the same thing he called that girl and telling her what she could do with her rules, was not try to get out of it.

“But why can I stay up late but not … you know.”

“Because I wanna hang out with you. Don’t you wanna hang out with me?” I meant it too. I’d rather hang out with him than put him to bed at 9:30 and watch Netflix on my phone for the rest of the evening. And if I said it in my you-don’t-wanna-hurt-my-feelings-do-you voice, well, so what? Like I said, not that hard to get boys our age to do stuff, and that trick works on charges of all ages. Do you know how many boys have puppy love crushes on me? Professional hazard that just so happens to make my job easier.

“Yeah,” he said. I think I detected a bit of shyness there beyond the utter embarrassment he’d been feeling since I walked in the door (actually, probably ever since he asked that girl out and got her response, the huge ‘C’ word).

“Good. I’m glad. If you behave yourself, you can stay up.”

“Okay.” Did I detect some conflicted feelings? Couldn’t blame him if they were. From having a babysitter, even a super fun one like me, to what his stepmom had told me to do, I wouldn’t have been upset with him if he said he just wanted to be alone his room. I was wondering why he wasn’t doing exactly that. I wouldn’t even have been upset with him if he threw me out of his house, or at least tried to. I could overpower him (he’s kinda little), but who wants to do that? I figured if his stepmom could get him to go along with her ridiculousness, so could I, and I intended to do it without being a bitch like her.

But so far it hadn’t even been an issue. He just … did everything I said. Maybe he didn’t go upstairs, slam his door, and pout in his room because I told him to go to the family room. Or maybe it was because I’d apologized for swatting his butt in the kitchen. Either way, he’d been a pretty cooperative, almost meek, kiddo since I’d arrived.


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really enjoying this story

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Wow! I was so neglectful in posting additional chapters! I’m such a space cadet this … year :sweat_smile:

Here’s the next chapter, and the full book is available on Kindle.

Chapter 3

Anyway, pizza is itself a great tool in the babysitter toolbox. Just about everyone likes pizza. In my experience, it’s a great way to get sad kids, mad kids, and bad kids to cheer up, and it worked on Gordy like a charm without my even trying. And I like pizza too. I did say we could still have a good time; I’m a babysitter – we know these things.

“You want another coke,” I asked him as he got some plates out.

“I’m not supposed to.”

Wow, yet another rule from the stepmonster. “Seriously? As if you might wake up dry if you don’t?”

“No,” he replied with some well-earned indignant irritation, “because it keeps me up.”

“Oops. Sorry.” My turn to blush. “Well, you’re going to stay up anyway, so up to you. I won’t tell.” Also, show me another adult who still gets affected by a coke that way. Weird. Sounded like another example of stepmom not updating a rule since he was eight.

“It’s okay. Yeah, I’d like another please.” He’s polite.

The Rooneys have a thing about eating in the family room, so we ate in the kitchen, and with a little pepperoni, Gordy plucked up the courage to initiate some small talk. “So, do you wanna find something to watch after dinner?”

I’ve always thought as a babysitter that it helps if you seem confident about everything. When you hesitate or sound unsure, some kids see that as a chance to get away with stuff they can’t get away with around their parents. Then the kid gets in trouble, the babysitter comes off gullible and less-than-competent to the parents, and nobody has a good time. I like having a good time; I like the kids having a good time; and when kids tell their parents they had a good time (without any booboos or property damage), the parents hire you again. Sometimes they even give tips. And they don’t negotiate as you steadily raise your rates. It may ‘just’ be babysitting, but it’s a business, and I’m a business major. My brand is competent, confident, fun, and safe.

But try as might, I could only come off as about 90% confident when I answered his question with, “Actually, I think it would be better if we got your spanking over with early. Like, right after we do the dishes. That way it’s over and done with, and we can go back to having fun. Sound good?”

Yeah, really wish I hadn’t tacked that on to the end. Force of habit, phrasing a here’s-what’s-gonna-happen statement as a question. Effective, but yeah, obviously didn’t sound good to him. He went right back into his shell with a morose, “Okay,” and added, “I’m full.”

What else could I do but try once more to downplay the whole thing, even if it did come off as half-assed justification for my suggestion to get him spanked ASAP, which wasn’t a suggestion at all. “No you’re not. You didn’t even finish one piece.” At least I didn’t say it in my you-silly-goose voice or tack on ‘three more bites.’

“Can’t I even decide if I’m full on my own?”

I don’t appreciate the kids I sit for raising their voice with me, but I made an exception. “Sure you can. Hey, be my guest. But you’re not full. You’re just feeling sorry for yourself.”

“And I have every right to be!”

Alright, the first one was a freebie, but not twice. “Do not raise your voice to me, young man. I can move your bedtime up too.” I waited for an apology, and when I didn’t get one, I asked, “You wanna go to bed right after your spanking?”

“Sorry.”

“Thank you. And cheer up already. We’ll get your spanking out of the way, we’ll get you in a fresh diaper, and we can sit on the couch and watch a movie together. Your choice. Isn’t that better than having your spanking hanging over you all night?” Maybe that’s specifically why she made it a bedtime spanking instead of giving it to him as soon as she heard. She did say it’s best to give consequences right away, so the delay didn’t make a ton of sense. I’d have really (like, reallllyyyy) appreciated it if she’d gotten it over with before I arrived instead of laying it off on me.

“I guess.”

I gently scoffed at him. He’s cute when he’s guessing. “I think you know it’s better, don’t you? Don’t you,” I asked again with a wink.

He took a deep breath through his nose and let it out before responding, “Yes.”

I slid his plate just a quarter-inch in his direction, and he started eating his dinner again. Not often that I have to work to get a kid I sit for to eat pizza. But he’s not a kid, and none of the others I sit for ever had a spanking coming after dinner. I know I probably shouldn’t have, but I was just too curious not to, so in the hopes of hearing wtf, I remarked, “Besides, it’s not your first spanking, right?”

Cute how he his tummy went from being too full to eat another bite to his mouth being too full to answer. But I was really curious (who wouldn’t be!), so I just said it. “I’m just curious. You don’t have to tell me, but obviously this isn’t normal.” I mean, I assumed it was obvious to him. It had to be, right? “Maybe it will make it less awkward to just talk about it. How does a twenty-year-old still get punished by his stepmom? I’m not judging,” I hastened to add, a white lie. I was judging. I was judging the stepmonster a lot more harshly; I was just sorry for Gordy, but if I’m being more honest than I was with him, I was judging him a little for going along with it. Just seemed like a self-respect thing. He should’ve shut her down hard.

“I don’t know,” he said and took a very long drink. Either he’s a thirsty boy or was trying to not answer and didn’t have the guts to just tell me to stop asking. Or both. Both would fit just fine.

“But you do know why you go along with it, right?”

“I don’t have anywhere else to go. Their house, their rules.”

“You really think they’d kick you out if you refused?”

“I guess not.”

“So why don’t you just refuse? They can’t physically make you at twenty.” I mean, they could, but not legally.

And that thought is when I had a horrifying revelation that I’m ashamed to say I didn’t have an hour earlier. “Gordy,” I said softly and put my hand on his wrist, “are they abusing you?” Cuz the whole thing wasn’t legal! There’s no such thing as implied consent for an adult to get hit. Just because he went along with it didn’t mean he was okay with it, which just left that he wasn’t okay with it, and they were doing it anyway! And I was a half hour away from being complicit in it just because … she told me to? I felt sick to my stomach.

“What? No.”

“Gordy, look at me. We can pack some of your things right now and you can come stay at my house until we call the police. Are they?”

“No, they’re not.”

“They’re treating you like a little kid. She spanks you! You’re an adult. That’s … It has to be abuse. I’m not trying to upset you, I just … C’mon. Let’s go get some of your things.”

“Stop it.”

“Gordy …”

“I asked for it, okay? Geez.”

Well … that shut me up. You coulda heard a pepperoni drop in the awkward silence that followed. So many twists and turns, and I’d only been there seventy-five minutes. I ran through a number of very appropriate responses in my head, such as ‘what’ and ‘huh’ and ‘whuh?’

I settled on, “You … asked for it.” And to compound the awkwardness, that’s when I realized I was still holding his wrist. I really had been about to drag him upstairs and start throwing stuff in a bag. I take my job seriously, and I take protecting people who can’t protect themselves even more seriously. I know it should’ve occurred to me to just reject all of it out of hand the moment the stepmonster pretended like this was all a mix up, but … I dunno. It seemed so natural to the two of them that it just felt natural to me, like a weird but normal-for-them stepparent-child relationship more than an emergency in the moment. Now that it wasn’t an emergency again, it was back to be a weird stepparent-child relationship … times about a million.

“You asked for it.” I really thought that bore repeating. “Are you telling me the truth?”

“Yeah.”

“If you want me to believe you, you need to explain.” I was still curious, but also suspicious. I needed him to explain. I wasn’t fully over my instinct to get him out of the house.

“I didn’t do so well my freshman year. I told my stepmom that I, um … thought I needed more … structure. Okay?”

“This … is a lot of structure. Sorry, not making fun, but … did you tell her specifically …”

“I just told her I thought it would help if I was accountable to someone again.”

“Did you say how?”

“Just that I did better with the rules I had before college.”

“So you got spanked all the way through high school.” Good thing he was already changing for gym in private. “Can I ask you something personal?” Like I hadn’t already about fifty times. “Do you like it?”

“What? Of course not!”

“Cuz most … well, just about everyone our age wouldn’t even let their parents ground them, let alone …”

“Grounding didn’t work before. She tried that for a while but … It’s like I have a super active social life. I never really cared if I got grounded so … She said grounding didn’t work with me so she went back to …”

“Spanking you? Just recently?”

“… No. She, um, told me when I, uh, brought up needing accountability that … she’d use the same consequences I got before college.”

“And what did you say?” Legit just fascinated now. Like, woah. IRL talk show.

“I said I didn’t want that.”

“And?”

“And she said I didn’t get a choice about how. That we either did it her way or not at all.”

“And you said yes.”

“Yeah.” He’s so cute when he blushes, though he’d been red-faced for so much of the time I’d been there it would’ve been fair to assume that’s just what color he always is.”

“And … you really don’t like it? Really?”

“No! I hate it. It hurts, and it’s embarrassing. But that’s what makes it a consequence”

“And not being allowed to go to your friend’s, having a sitter, the mouth soaping. That’s all part of it too?” He nodded. “And not being allowed to change your own diapers?”

Just above a whisper, turning an even deeper shade of red, he answered, “That’s only when I get a rash … I never get one when she does it, but … Not like I do it on purpose. It hurts.”

Learning a lot about Gordy and a lot about myself, from the eureka discovery that smacking him on the butt turned me on to finding, to my complete confusion, that learning he had a hard time doing a good job changing himself seemed a little adorable. I got a soft spot for adorable, but boys my age … well, Gordy was the first boy my age I ever thought of as adorable.

“Well,” I said, trying to get back to lightening the mood and salvaging our evening, “Hey, to each their own. I think it’s actually pretty cool that you were brave enough to ask for help and are doing what you need to for your own good. Not many people our age are mature enough to do that.” Especially the boys. Most of them, in my experience. The whole thing was lots of other things besides cool (and it wasn’t very cool at all, but I was trying to be positive). I just wanted him to feel better. He was having such a hard day.

“Um, thanks, I guess.”

“Yeah, and you know what? That just makes it a good thing,” I rambled and had to think fast to justify that bizarre point of view. “I’ll give you your consequence, and you know you need your consequence, and … yeah.” And he looked at me like I was nuts again. If I could have looked at me, that’s how I would’ve looked at me too. But at least I was polite enough to not look at him like he was even nuttier. Everything he said made a bizarre, if screwed up, kind of sense right up until the ‘and then I agreed to get treated like a little kid whenever stepmom thinks I’ve been naughty, up to and including pulled my diaper down and spanking my bottom.’ Just paraphrasing.

“Can I ask you a couple more things?”

“I guess,” he said like it made no difference by this point. Fair enough.

“What about like today? When you didn’t do anything wrong and you’re getting punished anyway? That’s not what you meant when you said you needed accountability. ”

“Part of what I agreed to. She said it couldn’t just be when I thought I needed it or just for some things. She said that’s not real accountability.” He finished off his soda. “And that just like she would decide the consequence, she would decide what I’d get consequences for. I didn’t think … I was just worried about grades and getting lazy with certain … things. I didn’t think she’d take it so seriously … or so often.” I wondered just how often but kept that question to myself. If I knew anybody who got spanked growing up, I wasn’t aware of it. How often was ‘often?’ I guess it didn’t matter.

“You could change your mind,” I suggested. Sort of an obvious suggestion. They can’t legally make him, and it would be a hundred percent illegal if they tried to force him. And now that I think on it, he hadn’t mentioned a word about his dad in all this. Maybe this was just between him and his stempmom.

“Yeah, but … my grades are better. I’m doing better in other ways. I just wish it weren’t so embarrassing. Kinda used to being changed cuz … But … And it hurts.” Couldn’t help but think of him as a little wimpy. He’s an adult. How much could it hurt?

“Ever tell her how it makes you feel?”

“She says embarrassment isn’t on purpose; it’s just a side effect. If I don’t wanna be embarrassed, I should behave, is what she says.”

“So if you’re, ya know, generally okay with this, why were you so upset when I got here? Just because I’m not your stepmom?” He nodded. “And because we’re the same age?” He nodded again. “Well, I won’t do it unless you say it’s okay. I’ll explain it to your stepmom so you don’t get in more trouble. I really owe her a talking to anyway. But it’s up to you.”

“It’s not like I want you to.”

“I know. You already tried to get out of it … I was kinda wondering why you didn’t try harder …”

“I … It helps most because I don’t get to decide.” Ah; so that’s why he didn’t try harder. Still thought it was weird, but I guess I understood.

“So you want me to give you your spanking?”

“No! … I mean, I don’t want a spanking at all, but since I’m getting one anyway … yeah.”

“And you’re not just saying that cuz you’re afraid you’ll get in more trouble?” I needed consent. Truly free consent. Then he could get what he (supposedly) needed, I’d continue to be known as the best babysitter in town, and I wouldn’t have to feel guilty. And maybe, fringe benefit, I’d get a chance to get hired by Mrs. Rooney again at three times my normal rate. Just sayin’. Lady owed me an apology and then some cuz in all my focus on consent, no one had asked me for mine until I’d already been sucked into her vortex of weirdness.

“No.”

“Well, okay then.”

“You don’t have to seem happy about it.” Finally he shows a little spunk!

“I’m not happy about having to give you a spanking, but since I do, I’m going to choose to treat it like it’s perfectly normal. I’ve had to give consequences to kids I’ve babysat before. Same thing: they get the consequence, it’s over, and we can have fun with the rest of our evening, but that only works when the kid doesn’t pout about it.”

“I’m not pouting!” I just looked at him. “Well, I’ll stop,” he said with a chuckle.

“Good. Not your first spanking. We’ll just do it, and then it will be over.” I think I was giving myself a pep talk as much I was giving him one. It wasn’t his first spanking, but it was my first time giving one, and it was going to be on the other side of my first big boy diaper change. But I could hardly ask him to be brave about it if I wasn’t going to be. Besides, like I said, babysitting always goes best when the sitter pretends to be calm and confident, whether they feel that way or not.

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Looks Like your latest chapter has a formatting issue. You’ve got some spaces or tabs a thr start of some lines that snuck in. If you remove those it should be fine.

If you need us to, one of the mods can fix it. :slight_smile:

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