The Best Babysitter in Town Vol. 2 Ch. 6 (Patreon)

The placebo effect of kissing a booboo? I am an expert. Making up after that kiddo one took this kiddo’s toy? I am a veritable relationship counselor. Treating phobias? Nobody tackles fear of the dark and monsters under the bed as good as I do. Identity crisis management? Not so much.

Unless you’re talking about being a DC versus Marvel person, the kids I sit for don’t have identity crises. Some have issues, some have special needs, and kids can have those sorts of crises very young, but none of the kids I sit for do, even the older ones. And suddenly I have a 20-year-old mentally battling with what it means to be young, lonely, and incontinent? In a clinical setting, maybe the attending physician would say ‘hold my beer,’ but a intern like me would probably be quietly asking one of the experienced nurses what to do.

This is what I was thinking as I changing out of the clothes Gordy piddled on. That poor boy. That poor, legally adult, actually-a-couple-months-older-than-me boy. It was enough to make me forget for a moment that my hand hurt. Spanking bottoms is not without its tradeoffs. Kinda fun and sexy, but my hand hurt, and I just really, really, REALLY did not like Gordy being upset, and I absolutely hate making Gordy cry. He knocked on my door.

“Just a minute,” I called back, then thought better of it. “Is everything okay?”

“… Yeah.”

“I’m changing my clothes. I’ll meet you downstairs, okay?”

“ … Okay … Sorry.”

O my god, what is he sorry for now?!? If there’s a word I ever wanted to wash out of his mouth … It wasn’t early evening, but we weren’t going anywhere. I put on my lounge clothes, which makes me seem somehow less slovenly than putting on pajamas before dinner.

Tossing my clothes into the laundry basket, I suddenly remembered this was not my first time being peed on by a peer. This one time at band camp (yes, literally at band camp, and no, I’m not a nerd), I ended up with a bottom bunk. And ya know what? I was super nice to that girl about it too. I didn’t want to let scents or stains set in in my clothes, so I grabbed the basket to take downstairs with me.

Washing three things doesn’t make much sense, so I stopped in Gordy’s room to get his laundry. I know I should’ve asked, but I didn’t because I just … didn’t. I’d ask, say, a roommate. Or a thirteen-year-old. But I just opened Gordy’s closet and didn’t even think that would be invading his privacy.

I didn’t go peeking through it. I did a glance, but mostly zeroed in on the laundry basket on the floor of the closet, not hard to miss because that’s where the slight scent of ammonia was coming from. A very faint smell, perhaps one only the best babysitter in town (or a mom with an accident prone kiddo) would catch, a power first developed when I worked as a junior camp counselor and got assigned to a cabin of six-year-olds, two of whom had accidents but only one of whom owned up to them. Follow the scent, and you’d find wet shorts and undies under her bunk. And I was so super nice to her too! Poor thing was just embarrassed. We worked out a whole system to smuggle her wet things out of the cabin without any of the other campers noticing.

I don’t know if Gordy is embarrassed by his condition so much as now he manages it, hence the whole pull-up charade. Maybe he was embarrassed about the leaks, but it was really just not wanting his step monster to find out about them that had him leaving wet clothes in his basket until he had the chance to wash them. I don’t think that was ever very long, or I’d have had a stinkier basket of clothes to do. You could look at his laundry and think, ‘geez, how gross, boys are dirty,’ or you could think, ‘aww, poor little fella was really desperate to make the switch to pull-ups work.’ Well, I’d gotten intimate with his personal area, and Gordy is not dirty.

“I grabbed your laundry,” I called out when I got downstairs. I figured he’d hear me wherever he was down there. The Rooneys have main-floor laundry, which seems like not a big deal until you’re the one who does the laundry.

Gordy appeared. “I’ll do that.”

“I got it.”

“But it’s … you know.” How I can do all the things I’ve done to him, for him and yet he won’t just say some of the words that goes along with it … Good thing he’s cute when he’s bashful, which is pretty much all the time. Me, in my quest to make it less embarrassing for both of us and maybe more normal, just said it. “I’ve washed peed pants before. It’s not a big deal and nothing to get embarrassed over.”

“Okay … I’m sorry again, for getting it on you.”

“Don’t be. It’s not your fault. I should’ve made sure the diaper was between us. You know why I forgot? Because I’m much more worried about making you feel better than I am about my jeans getting a little wet. It all washed out.”

He looked … I don’t know, to hear me say that. I don’t know what he makes of someone his own age caring about him like that or how it makes him feel. Watching his face, I realized I needed to be more careful about accidentally leading him on. I care for him; I have feelings for him; but I didn’t want him to mistake those feelings in a way that would leave him feeling rejected again.

So what did Gordy say? “Uh, thank you … Still, though, sorry.”

“Gordy,” I said to him, “if you say sorry again when you didn’t do anything wrong, I’ll wash your mouth out again. Do you understand me?” I was semi-serious too.

“Yes.” I could see the poor boy straining to not apologize for apologizing, and as well trained (cowed? Is that the right word?) as the stepmonster has him, I think he got the semi-serious part and none of the semi-unserious part at all. But if it got him to stop apologizing all the time, maybe better not to say it.

“Things happen, and they’re not your fault. Now, what are we doing tonight?”

The answer was ordering Chinese and watching a movie. Funny how Chinese takeout can be light in theory, but in practice I felt like I was being weighed down on the couch. Consequence behind him, he loosened up considerably.

“You get enough to eat,” I asked.

“Yes,” he said with a chuckle. “You don’t need to worry about stuff like that. I am twenty, ya know.”

Like I’d ever forgotten. “I’d ask the same question if you were 30, whether I was babysitting or not.”

“Why?”

“Because I just do. Someday I’ll probably be just like my mom, rushing around at Christmas parties so busy making sure everyone else is fed that I forget to eat.” Though not a problem that evening. I practically had a food baby. “C’mere. Let’s check your diaper.”

“It’s okay for a bit,” he said as he walked over to where I was sitting anyway. “And you don’t need to change me. I’m not grounded from changing myself like last time.”

“I know,” I said a teensy bit defensive. I did know. And yet I decided to check him anyway without thinking. Huh. I was babysitting; the boy I was babysitting wears diapers; my instinct was the check his diaper. I didn’t even think about it. I reached over and pulled his pants down to just below his diaper anyway.

“Then why are you checking me?”

“Why’d you walk over here?” Touché. Everything needed for a nice evening: leftover takeout and two awkward people, both acting on instinct. Me because taking care of people is what I do; him because following directions is what he does.

“You’re pretty wet. Turn around for me.” And he did that too. I’ll admit it had me wondering what else I could get him to do just by asking.

“Hey,” he grumped when I pulled out the back of his diaper and peered inside. A red but clean boy bottom.

“What? What did you think I was gonna do?”

“I don’t do that in the evening.”

“Never?” He blushed (again) and looked away and mumbled something. The note from his stepmom said it happens, and I learned last time he gets rashes because he has a hard time cleaning up back there on his own, which he wouldn’t have if he exclusively did that on the potty. “I thought so,” I (tried to) lightheartedly respond to his blush, but doesn’t have a very light heart. If I could only fix that for him. “Wanna take that off and go take your bath?”

“Not yet.”

“You should probably change anyway.” In theory, that was a suggestion. That evening in the Rooney home, not so much. I’m so good at changing diapers that I’d learned to do it perfectly on twenty-year-old boys after fewer than five times, and if I hadn’t put him in that wet diaper he was wearing just then, it would’ve been sagging down his thighs.

He legit rolled his eyes at me, reached back, and felt his own butt. “It’ll last a little longer.”

“I dunno,” I tried again in my skeptical persuasion voice, the one I use when I want a kiddo I’m babysitting to come around to my point of view but think it was their idea.

“Trust me,” he said and plopped his soggy bottom on the couch next to me.

“I’ve changed a lot of diapers, kiddo.”

“As many as me?”

Huh. “Well, I guess you got me there.” Of all the things for him to be arrogant and cavalier about … I guess we all have something we’re good at. I’d still bet money that I get them on tighter than he does though.

“Twenty minutes, then it’s either bath time or new diaper time.”

“Yes, mother.” I heard the playful sarcasm and decided to play along.

“For this weekend, darn right, and you’d better watch that sass mouth if you don’t wanna another trip across my lap.”

I knew that was way too playful the moment it was out of my mouth. Fuck, before it was even all the way out of my mouth. And Gordy not laughing but definitely looking away confirmed just how stupid it was to say

“Sorry,” I rushed to add. “I didn’t mean that. Bad joke. Step too far.”

“It’s okay.”

“No, it’s really not. That’s not something to joke about.”

“It’s okay, really.”

“Hug?” Was I overcompensating? Yes. Was I probably making it more awkward? Yes. Is a hug the main tool in the babysitters let’s-make-up toolkit? Also yes.

We could’ve resumed movie watching while I mentally counted down the twenty minutes, but nope. Maybe it was the MSG or my innate caregiver instincts, but the pause in our banter (that I cause) seemed an opportunity to raise a question that had been bothering me, and I raised it without thinking whether it was a good time for it or not.

“Gordy, how are you feeling about earlier?”

“My butt hurts. I’m not mad at you if that’s what you’re asking.”

“No. I mean I’m glad you’re not mad at me, but what you said on my lap, that just don’t wanna be a, you know? Are you okay?”

“Yeah,” he said, clearly uncomfortable talking about. But sometimes, when it comes to my charge, I see those kinds of signals and ignore them if I think it’s important. See above about me sometimes going too far.

“Really? You don’t have to talk about it. You were just really upset.”

“That was just, uh, my spanking.”

O nice try. “I’ve only spanked your butt and only twice so far, but I can tell the difference between tears from an ouchie and tears from hurt feelings.” Did I just say ouchie? Stop that! But I really can tell the difference because, as I’ve said, I’m the best babysitter in town. Not that you’d need to be if you heard what Gordy said and the way he said it. That was some inner turmoil he was giving voice to.

He responded by taking a drink. It would’ve been a great time, if he wanted to avoid the subject, to head upstairs for the tub. He didn’t. I know I should’ve let it go, but I pressed anyway.

“You’re worried that you’ll never have a girlfriend because you wear diapers.”

“… Yeah,” he super grudgingly muttered.

“I don’t think that’s true. I think you just haven’t found the right one yet.”

“How can I find the right one when I can’t even tell be upfront about it? It’ll just scare them away. It’s not exactly something you put in your dating profile so you can skip past all the rejections. It’s hard just asking someone out, even online. And then if I tell them later, it’s like I was hiding something and they’ll be mad about it. I’ll either get rejected or dumped … And what if they don’t keep it private? … Like that girl on campus.”

“She’s a cunt.” Which he knew since he’s the one who called her that first. “Most people are not.”

“Still,” he said and just looked unhappy the way only Gordy and 8-week-old labradoodles can. I am such a soft touch sometimes.

“Alright, c’mere.” I leaned back into the corner of the couch and opened my arms. He scoffed. “I’m serious.” It’s easier to talk about some things when you don’t have to look at the other person. Plus it’s a lot easier to deliver a pep talk/lecture if the person can’t get away. Gordy rolled his eyes, but obedient as he is, leaned backed against me and let me put my arms around him. Pretty sure he didn’t dislike it as much as that eye roll suggested.

“Some people,” I told him, “will turn you down for a date for no reason, or break it off for some other reason, or yeah, maybe because they can’t handle your condition. That’s just dating. Would it be easier without your condition, yeah. But it’s not impossible because you have it.”

“I’ve never even been on a date.” I knew that; the subject came up the last time I sat for him, leading to a sympathy HJ that was my idea, his first, and that last about four seconds. I did it because I wanted to and he wanted to, but I still had no idea if that was a very bad decision on my part.

“Some people are late bloomers,” I reminded him.

“Well, I’m still waiting then,” he chuckled but not the funny kind of chuckling. “Even without my problem … Almost no one knows about it, and it’s not like I have girls flirting with me or swiping right all the time.”

“People have different types, Gordy. Just because you’re not a football start doesn’t mean there aren’t women out there who find you attractive. You are attractive, and besides, you offer more.” Don’t get me wrong, I like a hard body frat boy as much as the next straight co-ed, but they tend to be so full of themselves. Like God personally gave them a six pack. To say nothing of irresponsible, immature, and generally not ready for a relationship. I do the very occasional one-night stand, one time I had a friends-with-benefits thing, and I do relationships. That on/off, when-it’s-convenient, are-we-dating-or-what-even-is-this thing, I don’t do. I hadn’t been a relationship in a while; too busy going to school and paying for school. Maybe I’m not giving the larger college boy community enough credit, but from my own limited experience, the hotter they are, the worse they are as boyfriend material. And I meant what I said to Gordy; he is attractive in a more boyish-good-looks kinda way than a full-time-athlete-part-time-fireman kinda way.

“Like what,” he asked me.

“Are you fishing for compliments now, or do you need me to remind you you’re smart, handsome, sweet, kind, and funny? I could be spending my weekend with a lot of other people, but I wanted to spend it with you, and not just cuz your stepmom is paying for three whole credit hours.”

“Why then,” he said as he twisted his head around to look up at me. “I know you don’t like … following her directions.” If only that we’re 100% true instead of a soft 95%, I’d have so much less guilt … which is maybe why I was so determined to help Gordy. It wasn’t my only motive though. He’s my friend.

“Because we’re friends. How long have we know each other? I’m sorry we weren’t close friends a long time ago.” As I said that, I was reminded that I don’t sit like I was sitting with my other friends like I was with Gordy, him leaning against me with my arms over him, except maybe my best friend. Last time I sat like that was with a boy was my last boyfriend, and I was the one leaning into him.

“Weird friendship,” he chuckled. That time it was a funny chuckle.

“It is what it is. I can be your friend and your babysitter at the same time. Even your stepmom can’t stop me from being your friend when I’m babysitting.”

“Do you really have to call yourself that?”

“What, your babysitter? Is it any better to call it something else like I’m not the person your stepmom pays to stay with you sometimes?” It’s more normal - or at least less weird - if we treat like it’s normal. I’m just the woman his stepmom hires when she needs someone else to spank and diaper her twenty-year-old stepson. Yep, so totally normal …

When he first sat back against, he didn’t put all his weight on me. I don’t think it’s because he’s worried he’ll hurt me; after all, I held his weight over and in my lap just fine. I think it just awkwardness, and now he was relaxed all the way against me, not snuggled in but plenty comfy. I just wished he were happier just then (and all the time).

“Can I ask you something else? Getting spanked is cathartic for you, isn’t it?”

“What?”

“I get that it’s not sexual. I believe you. But it’s not just that you think you need consequences. You needed to get some feelings out and have a good cry, and you did. It’s cathartic for you.”

“Why are you asking me these questions?”

“I like helping people. I just … can’t help it sometimes, being a caregiver.” I’m the mom friend, the one who holds the hair back, makes sure everyone is reapplying sunscreen, making sure no one forgot anything. It’s who I am.

“What do I need help with?” I detected the thinnest thread of resentment in that question. Fair enough, but I think that resentment was directed more at everything (and everyone) that led him to where he was in life, not at me.

“Someone you can share everything with. Someone you can be yourself with and have fun and not ever worry I’m judging you. Someone to remind you how great you are, just the way you are.”

“Makes me sound kinda pathetic.” I swear to god, if only I could spank the bad self-esteem and self-pity out of this boy …  Jesus! He’s not like that on campus, and maybe he’s not like it when he’s home and in trouble or just got out of trouble, but I hadn’t spent time with him at home when he wasn’t in trouble. I also understood, though, that his problems aren’t just about home. So maybe he was hiding his feelings all those times he wasn’t alone with me. Or not; or something in between; or some days some problems bother him more than others, like feeling he won’t ever find someone who won’t mind that he needs diapers (and won’t scared off if they ever find out about the arrangement with the stepmonster - how’d you like her as your mother-in-law).

“I don’t pity you, if that’s what you think,” I said in my this-babysitter-is-not-kidding tone. “You’re not pathetic. I think you’re just feeling sorry for yourself because of what happened today, but it’s over.“

“I’m still a diaper boy,” he said kinda bitterly. I understand where he was coming from, but being bitter about it would accomplish absolutely nothing.

“So be a diaper boy. Own it, but you’re still Gordy, which is way more important than what you wear. I know it’s easy for me to say, but please don’t let your condition hold you back from sharing yourself. You had a super bad experience. I get that you’re scared of putting yourself out there again, but I promise it’s not always going to be that way.”

Wow. Getting heavy, right? Always a sign I should’ve shut up and stop playing amateur psychologist. I tried to lighten the mood a bit with a another bad joke (ya know, cuz the first one went over so well). “I’ll bully you into getting over it if I have to … Does your silence mean ‘Gee, you’re right, Sally’? … I thought so.”

“Big bully.”

“So you can push back after all.” I poked him in his side. “And I am the very worst kind of bully.”

“What kind of bully is that?”

“The girl-next-door babysitter; we can really be just the worst tyrants. Fortunately for you, I got a soft spot for twenty-year-olds in need of looking after.”

“I don’t need looking after.”

“Just teasing, but I do have a soft spot for you. And twenty minutes is up. What’ll it be? Bath time or fresh underpants?” Also, yeah, sure, he doesn’t need any looking after. Why would anyone come to that conclusion ever in a million years? Just because he was delaying his bath and sitting in a very soggy diaper with no apparent intent of doing anything about it?

“You’re really gonna change me even though I’m allowed to?”

“If you don’t do it often enough, yeah. I’m not letting your stepmom come home to find you with a diaper rash. I have my reputation as the best babysitter in town to protect. But I’ll also do it if you just want me to. Or not, if you don’t want me to … Actually, no, I will anyway if you don’t do it enough.” I’d never say this to him, but wasn’t the 20-year-old leaning into me the same one who got his bottom spanked for letting his pull-ups leak and lying about it? I get that pull-ups aren’t diapers, and I get his motivation for trying to make them work and lying about it, but also … I wasn’t 100% sold he was the best at changing himself often enough. Heck, the last time I sat for him, he was grounded from changing himself because he got a diaper rash. I was torn between consent on the one hand and being a good babysitter on the other. If he didn’t want me to change him, I wouldn’t, but I’d sure as heck nag him into doing it himself if he wasn’t going to be responsible about it.

So what did Gordy say? “It really doesn’t gross you out?”

“No, sweetie. It doesn’t. So what’ll be?”

“Guess I’ll take a bath first.”

I opened my arms, and he sat up, turned slight toward me, turned away again, and he just sat there.

“What?” I had an inkling.

“Nothing. Never mind.” He started toward the stairs.

“Hey, that bathtub in the guest room is huge. Wanna use that instead?”

“Uh, yeah. Thanks.”

“Kay. I’m going to go switch over the laundry, and then I’ll be up to check on you.”

“Check on what?”

“Just go,” I answered and added a swat to his butt. Boy’s diaper was soaked. Five more minutes and I’d have had more laundry to do.

And did anyone else notice he neither asked me to change him nor asked me not to change him? Glad we had more clarity on that.

As for what I was going to check on, I was planning on checking to make sure he wasn’t dawdling. If he was going to get another HJ like last time, well, I hadn’t decided yet (but I’m pretty sure that’s what he wanted to ask when he didn’t get off the couch).. Guess it depends on if he needs help washing like last time, poor boy getting lost in his many, many, complex, existential thoughts. I mean, the one led to the other last time. Not like I offered out of nowhere. He was sitting there in a funk, I didn’t wanna spend the evening waiting on him to finish his bath (or clean up an accident in the bath, if ever does that and god I hope not), so I took the soap and was washing him all over, and I got to that part and … This is me retroactively justifying myself, which I don’t need to do. He consented, I consented, and it was fun for both of us. If I decided to again, same. Why was I inventing a quandary? Or maybe that’s not what he was going to ask and I was the only one thinking about it.

As to getting lost in those thoughts, I understood he had his whole world on his mind. I doubt it was just that bitchy girl outing him on TikTok either. I think he had the same anxieties before that, which makes him even more awesome for working up the courage to ask her out, and lord knows the stepmonster couldn’t possibly be doing anything but making those anxieties worse. Though he really did get some bad feelings out with all the crying. Doubt she understood that, or I’m not sure Gordy even understood that motivation, if it was one of his motivations, but his meltdown helped me make a lot more sense of their weird ass arrangement.