The Best Babysitter in Town Ch. 2 (reposted with photos) (Patreon)

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 going to be the least invasive physical contact we’d be having that evening.

“I am so, so sorry. Are you okay?” I mean, this was Gordy! Don’t be mean to Gordy is just a rule and has been since we were both five years old. Like he doesn’t have enough crap to deal with never getting out of diapers without his peers giving him a hard time about it or anything else. 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.

But he didn’t need a babysitter, he should be allowed to change his own diapers, and he’s way too old for spankings! And mouth soapings (blech!)! And even if his stepmom disagreed, 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 sit for and be the one to give him his spanking. I knew she was strict, but until that night, I didn’t think she was, well, a ‘C’ word herself. 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 silenced his protest with a spank on his bottom.

“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 wanna 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 was I feeling more awkward than ever in my life, was it 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 it 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; he wouldn’t wake up dry; this wasn’t something he was trying to outgrow. It’s just his life, and really not a big deal. He was diapered when I met him; it’s just part of his life. I wasn’t fixated on it or even that worried about changing him. I was much more worried about spanking him.

I found him on the couch wearing the saddest puppy dog face I’ve ever seen on someone over the age of ten 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 have been 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 a couple 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 was 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. Even without all that other stuff, just living with her put his shoes in a whole other country. “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?” If he said she’d just turned him down, I wouldn’t suspect that. But he said she made fun of him, and what’s the most obvious thing a cruel excuse for a human could make fun of him for? 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.” All the sounds a person with trauma makes. Poor guy.

“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. Not so much him.

“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 she did.” 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, which he wasn’t and also, of yeah, is twenty flippin’ years old!

“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 off 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 he didn’t get spanked probably before breakfast.

“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, go put clothes on and we can go to a copy place 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 the entreaties of pretty girls 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 put my hand in his pants, maybe a reflex for him by then.

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. It’s his normal, so why not at least try to treat it like normal? That’s what I was trying to do. Just babysitting for someone in diapers; been doing it once or twice a week since I was thirteen; awfully different circumstances, but what else could I do but at least try to make it less awkward besides treating it like it was ordinary?

“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. “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. Cowboy up and accept the consequences, unjust or not.

“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 of a person).

“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 all evening. 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 have 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.