The Best Babysitter in Town Ch. 1 (reposted with photos) (Patreon)

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 caregiving 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 their fridge. I didn’t get where I am as a sitter by abusing fridge privileges, but I don’t pass up the benefit either. Mrs. Rooney 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-upper-middle-class thing down pat. Literally the only people I know whose entryway is 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 fifteen 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 figured, quite reasonably, that was because he was the same age as me. By the time I was old enough to babysit, he of course didn’t need a babysitter. Come to think of it, he was never even home when I sat for the younger kids because if he was, then why would the Rooneys 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 sometimes I prefer not to leave him alone.”

“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 very nice too. We just hang in different crowds.

“Not exactly,” Mrs. Rooney told me with that same please-I-really-need-this-and-I’m-sorry look on her face. “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, but what did she mean about his getting in trouble? I have a hard time imagining Gordon ever getting in trouble. “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 was 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 both way too old for a babysitter by about eight years, let alone a timeout. And unless he just likes standing in corners, he was in timeout. So … what strangeness did I walk into?

“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 developmentally 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 gym 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 ten 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 at home for a month.”

Not surprised exactly. She’s one of the stricter parents I sit for. So yeah, she’s his stepmom, but she’s not really an evil stepmom … that I knew of right then. 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 already being so embarrassed, 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?

“Fine.”

“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, but 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 a 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 and finally picked his head up. 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 and most of the girls we graduated with 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 in his eyes, 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 when we go out. Why don’t you tell the story, Gordy, since you think you can 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 considerate and, ya know, normal) 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, no matter how obviously valid, changing her mind.

Mrs. Rooney is a fit woman; I’ve seen her play a heckuva game of tennis at their country club (where sometimes parents have me take their kids for the day; my family isn’t so much the country club class), 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 for 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 three 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 to listen from.

“Are we ready, honey,” Mr. Rooney asked as he appeared from somewhere. Not that I wanna be thatbabysitter, 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 literally tapped a tantruming toddler on the bottom once before, but even close to 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 and giving a potentially fatal Parental Look, I think I’d have kept my mouth shut. I think he realized that too, a second too late, 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 critical to my job to not let ‘you’re just the babysitter, you can’t XYZ’ slide. On one hand, pick your battles. On the other, some battles you gotta fight.

So I got up and connected that hard with Gordy’s butt twice. “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 I’d never felt the way I did right then without a D or a D-cell battery to help out.

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 hatedthat I made him feel that way, even if I was just his stepmom’s instrument. But also, and I feel guilty for saying this, it kinda added to my arousal hearing him sniffle. I spanked a man to sniffles, and … it was gratifying. 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’ want me there? Try resented the hell out of me being there, understandably so. And I resented the hell out of her asking me to sit and springing this on me. I don’t care how badly she and her husband needed a night out, she was deceptive.

“We’ll be home very late.”

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

I stood against the doorframe to the kitchen and watched Mr. Rooney count out three hundred dollars and put it next to the pizza money. Who even has three hundred dollars cash on them? 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.