The Best Babysitter in Town Vol. 2 Ch. 5

I wondered if maybe by the end of the long weekend I’d stop being caught off guard by Jordy’s bare skin. He was dressed when he came back to his room, thank goodness, and I don’t know why I even worried for a moment he wouldn’t be, but he hadn’t put his shirt back on. Despite being the babysitter and having quite a bit of latitude with him, I didn’t feel comfortable giving him orders, nor did I feel comfortable saying anything that would make it obvious I was looking at his body. So I didn’t say ‘put your shirt on’ and I didn’t say ‘please put your shirt on?’

In the time I’ve have had to think about it since, I’ve decided the reason it bothered me is because there wasn’t anything clinical about it. He needs diapers, so seeing his diaper area is clinical. That time I sat next to him while he was in the tub, and helped him with it and then some, it was a bath (at least at first), well within the norm for a caregiver to help with and therefore, in a way, clinical. Having his bare butt over my lap isn’t clinical, but it’s … something.

Gordy being half clothed, no matter which half, outside those things is just a 20-year-old boy with no clothes on. I get why it doesn’t faze him, but to me it’s like … Know who else doesn’t think anything of being half or totally naked in front of people? Little kids, which Gordy definitely is not. It would be different if he were shirtless at the beach or even at home if we were dating or something, but he was just shirtless in front of a friend, a female friend, inside in October. He’s had a lifetime of his body being exposed to his stepmom, aunt, school nurses, and babysitters. I get why he doesn’t put value into bodily modesty. I didn’t have that history with him yet, and I was too bashful to say anything about it. So what did I do? Not comment on it; treat it like it was totally normal. Honestly, not the first person I’ve babysat who just gets undressed sometimes without a reason to. There was no reason for him not to put his shirt back on. Anyway, long digression.

“Sorry I took a while,” Gordy said. Of course he said that. The boy apologizes for things he doesn’t need to apologize for way too much. I’d only been waiting about 3 minutes.

“Don’t be sorry.”

“I, um, got this from my stepmom’s room.” He moved his shirt to his other hand and unveiled her wooden hairbrush. It’s not like he put his shirt on after, so he probably wasn’t trying to hide it (hide it from whom? we were alone, and he was giving it to me). That brush is bigger than a brush needs to be; it’s heavier too. It’s an antique, I think, and maybe a lot of brushes were made like that back whenever. Only the bristles made it a brush and not a paddle. An otk paddle, I’d learned while exploring the new and exciting feelings spanking Gordy last time had unveiled to me.

“Set it on the desk,” I said, trying to sound like everything was normal, this was nothing to be scared or upset about, and everything was normal (did I say that already?). He did, and then I said, “C’mere, tiger.”

What. The. Fuck. Is wrong with me sometimes. I swear.

Gordy shuffled over, and I motioned for him to lay down on the bed. He nodded toward the changing table. “This’ll be real quick. Let’s just use the bed.” He laid back, and I grabbed two wipes from the warmer under Gordy’s changing table.

I tend to baby talk a lot when I’m changing diapers. Obviously not gonna do that when changing Gordy, but in the spirit of normality, I made small talk. “Lift,” and he did and I took his sweatpants down. “Are you scared?”

“No.”

“Nervous?”

“Yeah. I get nervous every time.” One of these days I’m going to ask him how often those times are.

“I’m sure you are,” I said as I untaped his diaper. I opened it a little but left him covered. Later on it occurred to me I didn’t need to be doing this. Unlike last time, he was allowed to change his own diaper. I just … had a boy to get ready for a spanking, and I didn’t even think about it. Just like taking his pants down and underpants down, except I had pants and a diaper to take down, which I guess are his underpants. Yep, a boy to spank, and therefore pants to be taken down, a diaper to be taken off, and a boy to wipe clean, who is twenty … so normal that I had to remind myself to treat it all like it was normal … yep.

“But,” I said in a cheerfully normal way, “and I don’t mean to embarrass you by bringing it up, you’re not crying this time. Last time, you were crying before I even got you over my knee.” I figured that was enough time keeping his diaper open but covering him. If he was gonna pee on me, he’d have done it already. “Not that anyone should ever be ashamed of needing to cry. You’re being very brave, and I’m proud of you.”

“Heh,” was all he said in response. I took that to mean he didn’t see what I’d said as a compliment in the same way I did. I doubled down as I cleaned his diaper area.

“And you know what else? It makes me happy you’re not crying. And you know why?” I waited for him to answer that time.

“Cuz … everyone is always happier when someone isn’t crying?”

“That and because I think last time you were crying because it was the first time I spanked you, and you were nervous and maybe even a little scared because of that, and maybe thinking I’d tell people. But now you’re not crying because you know I won’t do that or hurt you. I think you’re starting to feel safe with me.”

And I wanted him to feel safe with me, and I also wanted to distract him from me cleaning his diaper area, especially when I tapped his knee and he instinctively pulled his legs and up and back so I could get to his boy button with a wipe. He was too busy listening to me to blush; as cute as he is when he blushes, I do wanna help the boy save a little face. And his stepmom was right; he could do a better job on cleanup back there. I’d give him an A- on it, just to make it clear he’s not a C student or worse in that area, but he could for sure get a few extra points. Can’t exactly blame him though; I’m sure the mechanics of it are hard, that big a mess … anyhoo.

I put the wipes into the diaper and rolled it up part way before leaning over him. “You’re being very brave.”

“You keep saying that like you expected me to …” He finished that with a sigh.

“I keep saying it because you keep being brave, and I know you’re going to be brave for your spanking. We’ll get you spanked, you’ll have a little time to compose yourself, and then we’ll have a good rest of our evening, just like last time. Okay? Just like it’s one of those things.”

“What things?”

“Anything. Some people need help with math or brushing their teeth, and some people need help making good choices. That’s the point of this, right? That’s why you do this? So we’re going to treat this like it’s normal. We’ll talk about what you did wrong, I’ll put you over my knee for your spanking, I’ll spank your bottom for you, and then we’ll talk about making better choices in the future. Are you ready?”

Maybe I shouldn’t have said that, because instead of looking reassured that all this was normal, he was making an uwu face. More accurately, he was trying to hide an uwu face. His eyes got watery.

“Lift your butt, sweetie.” He did, and I rolled the used diaper the rest of the way up and taped it into a ball. I set it aside and held out my hands to help him sit up. When he was on his feet, I turned around and walked to his desk, turning the chair around and telling him, “Please throw that away and bring me one of your spanking diapers.” I sat down.

“My … what?”

“Those ones,” I said and pointed, “the ones your stepmom puts under you when she spanks.” I guess there was a more artful term. The whole point is the spanking diapers are bigger to protect her lap, but all his diapers are big, at least compared to the ones I usually change. Big boys have big diapers; who woulda figured, right? I kept my eyes front as he did as he was told, and then he was right in front of me, diaper in hand and diaper area right at eye level. A fleeting thought went through my head: how many diapers do I have to change his diapers and spank his bottom before his weewee just being right there in front of me doesn’t make me blink in o-yeah-he's-naked-again surprise.

I looked up, and he was looking not happy about what was about to happen. I wouldn’t be either, but I have a better poker face. I was set on not letting him know, or at least not making it obvious since he already knew, that I hated doing this. I think we both knew it was abnormal (at least 50% of us did), but I didn’t want my expression to betray that. I didn’t want to make him feel worse.

The last time I’d scolded him before a spanking, it was with me seated and him on his feet. I learned that night that Gordy both dribbles (overflow incontinence) and other times lets loose all at once (urge incontinence, and since he has both, that’s called mixed incontinence – I did my homework). I had an incontinent boy who’d been undiapered for a couple minutes, and so I made the executive decision to spread the oversized diaper across my lap and have him get into position before his scolding, just to be safe.

The spanking diapers are so crinkly. They feel cheap compared to the ones he actually wears. I spread it out and told him as normally, but firmly, as I could, “Okay, get across my lap.” I tried and maybe succeeded in sounding like this was serious business but also not you-are-in-so-much-trouble-young-man super serious. Gordy takes things hard; I could tell. I hope the stepmonster never raises her voice at him. That would be somehow worse than everything else she does.

“Here,” I said and took his wrist to guide him across. “You can put your hand on my knee. You won’t hurt me, remember? Are you comfortable?” He was basically two sides of a triangle with the floor making up the third side. “Gordy, relax. Put your weight on me. It’s okay. You’re not too heavy for me.”

“Sorry.”

“Don’t be sorry.” I rubbed his lower back and the top of his butt cheeks. I hoped it would help him relax, and it did, but not before he startled a little. That’s a sensitive area for a lot of people (it’s an erogenous zone, actually), but I think it was more that Gordy isn’t used to being touched there in that way that made him jump, not that he was jumpy about the spanking he was getting. Twenty-year-old boys, like everyone else, need gentle touch.

“Shhh. You’re okay. Comfy now?”

“Mhmm.”

“Open your legs for me a little.” He did, and I pulled the diaper up between his thighs, making it easy to pull over him if he started having an accident; I knew for sure he would piddle. I tucked the diaper back out of the way so I had a clear … flight path, we’ll call it, to his butt.

I didn’t want to belabor the scolding since he’d already gotten one before his mouth soaping, but I had to and maybe even wanted to say at least something. “Do you know why you’re getting this spanking from me?” I mean, other than that his stepmom told me to.

“Because I lied.”

“Because you lied. You have every right to privacy,” I said to the grown adult whose diaper I’d just removed so I could spank his bare bottom. My philosophy prof could probably write a whole book on those two sentences, not that I’d ever tell her, of course. “But you also made an agreement with your stepmom, and it’s not okay to break agreements. And you know she’s just trying to help you. I understand why you did it, but it’s still not okay. Understand?” I actually do believe it’s not okay to break your agreements, so from that very narrow lens, I could agree that a consequence was warranted. But not the consequence he was getting, and not for the reason his stepmom wanted him to have it.

“I understand,” he said in a feeling-sorry-for-himself huff.

“Until you consistently make good choices, you’re going to keep getting your bottom spanked. You decide when you’re too old to be spanked, and you show it through your behavior.” I had no idea where that came from (was I channeling my ancestors or something), but I said it, and it had the very odd quality of being true, unlike my insistence that everything about that whole mess was normal.

“I know.” There was a pause, and he mumbled something.

“What was that?”

“She always says I listen better over a knee.” If I thought back twelve years ago to when I’d last been in his position, yeah, I imagine my ears worked better in that position too.

“I’m sorry I lied. I’m sorry I broke our agreement. I just …” He sniffed, and I could hear that his sinuses were getting full, and I knew that meant that he was probably trying very hard not to cry, and that once he started, he was probably going to blubber. Not about the spanking, but about the reason he lied and the way it hadn’t worked out.

“Shhh,” I cooed. “We’ll talk about that after. Are you ready?”

He nodded, I raised my hand, and just like that I was once again spanking a twenty-year-old boy. This time he was completely naked, and this time he started crying pretty much right away. Last time, he’d cried before I started spanking, stopped and managed to be pretty stoic until I put the hairbrush to work, and then he started to sob with real tears and a runny now, the works. I knew how to spank this time, and I knew to start it harder than I had last time, but that wasn’t why he was crying. He was crying because something hurt on the inside. Poor boy.

I spank-spank-spanked hard with my hand. I spanked at random. I spanked the same spot five times in a row and moved to the other cheek. I spanked his sit spots (I learned the term, and I tell ya, that research did not feel like homework). I spanked his thighs a couple times. I spanked when I felt the diaper between us grow a little warm. I spanked until he kicked his foot, just once. And he cried through it all, from the very first spank, and he cried hard.

“Gordy. Gordy! Catch your breath. Listen,” I said and punctuated with an attention-getting smack. “Take a deep breath.”

“I’m sor-orr-y,” he sobbed. And I mean sobbed. I looked from him to the hairbrush and didn’t know what to do. Should I have stopped? Was he well spanked enough? His butt wasn’t the shade of red I knew his stepmom would’ve made it, but he was genuinely sorry.

I could’ve asked Gordy. I could’ve asked him if he needed more spanking, and I think he would’ve have answered and not even found the question odd since he had, in effect, been the one to decide his spanking days weren’t over. Not when he told his stepmom he needed to be held accountable again, but when he didn’t back out when she made it clear that meant the same kind of accountability he’d gotten before.

I picked up the brush, tightened my hold on his hip, and brought the brush down on his butt with a thwack! The diaper grew warm again over a much bigger area than before, and I pulled the diaper up between his legs. There was enough butt to spank even with the diaper pulled up, so I kept spanking. I spanked hard. I spanked harder than I did last time. I wanted his butt to get to that shade of red quickly, so we could be done, and I could do one of the things I do best as a babysitter: make my charge feel better. I probably needed to be done more than he did.

Satisfied with the shade and not satisfied at all to have a sobbing, crying, groaning boy over my lap, I set the brush down and started rubbing Gordy’s back, shushing him and cooing and letting him have his cry to get all the feelings out. He’d had a good cry last time, and I’d been surprised an adult would cry because of a spanking, but I realized it wasn’t just the pain. It was the emotion. The spanking just helped get the emotions out. So I expected him to cry this time.

What I did not expect was for him to catch his breath enough to say, “I get more for lying.”

“What?”

“She sp-spanks l-longer for ly-lying.”

“No,” I said softly. “Sit up. C’mon.” I helped him sit up. I didn’t think I’d ever have a freshly spanked, crying 20-year-old boy sitting on my lap on a freshly spanked bottom sobbing into my shoulder, but there he was, and there was me, and o yeah, a diaper. Last time, I’d comforted him on the bed. I asked if he wanted me to leave him alone for a while like his stepmom does, ya know, give him some time to compose himself? He said no. He wanted me to stay, and I’d taped the oversized diaper closed, and he laid face down on this bed while I stroked his hair.

This time, he sat in my lap, and I rubbed his back and bottom and ran my fingers through his hair, and I told him, quietly as he sobbed into my tee shirt, “I won’t ever spank you that hard or that long. I don’t care how she does it. That’s not how I’m gonna do it.”

I caught myself rocking just a little, just barely, and totally weirded myself out by it. I stopped right away. “Shh,” I shushed. “You’re okay. Your spanking is over, and everything is forgiven.” I had nothing to forgive him for, but I thought hearing it would make him feel better. But that wasn’t what had him having such a hard cry on my shoulder.

“I-I j-just did-didn’t wanna be a a diaper b-boy anymore!”

That’s what he said to me, and my heart broke a little for him. Now my eyes were watering, but my feelings, other than that I understood and wasn’t upset with him, stayed out of my voice. “I understand,” I cooed. “I know. You’re not a diaper boy.”

“Yes (hhh!) I (hhh!) a-a-am!”

“You’re someone who has a medical condition and wears diapers to manage it. That doesn’t make you a diaper boy.”

“I don’t wanna hafta to w-wear them anym-more.” He was calming down, still sobbing, his diaphragm still cramping, but the tears were down to a trickle.

“I know. I’m sorry you have to, and I’m sorry you have this problem, but it doesn’t define you. You’re so many wonderful things, and what you wear and your condition don’t change that.”

He didn’t respond to that. He sniffled. “C’mon,” I said gently. “Let’s get you into a dry diaper and redressed, and we can talk about this more, okay?”

He stood up, and the diaper on my lap fell to the floor when I did the same, and with my arm around him, we walked the few steps to his changing table, and he climbed up. His face was so red, his eyes so puffy. I pulled a wipe from the warmer and stepped around the table so I was standing at his side and wiped the tears from his cheeks. He told me last time he could that, but he held still this time. “Here,” I said, “blow your nose.”

The left shoulder of my shirt and most of my chest was wet, and not a little bit of snot got on me. I was expecting tears, not a breakdown. With his feet in the stirrups and Gordy still sniffling with the occasional hiccup, I diapered him. I could’ve let him do it himself, but it seemed like the nice thing to do, a helpful thing, and I like helping Gordy. He didn’t protest.

When he was padded and I gave the front of his diaper two pats to let him know I was done, he sat up, and I grabbed his sweatpants. I forgot myself for a moment and was about to hold them out for him to step into before remembering could he do it on his own.

“Are you okay,” I asked him.

He nodded, more of a quick series of jerks, and said hoarsely, “Yeah. Sor …”

“Nope,” I said and put a finger on his lips. “Do not be sorry for needing to cry. I think you had a lot to get out, and that’s okay.” Whether five or fifty, that’s okay; I believe that, and I’ve sat for more than a few kiddos, mostly boys, who need to be told it’s okay to cry because someone in their life or just society told them different. He sniffled back a full nose and nodded his head again.

“I’ll take that,” I said and took the snotty wipe from his hand, stuffing it into the chute in the table that goes to his diaper pail. “Go the bathroom and wash your face and finish blowing while I change, and I’ll come find you.”

That’s when he noticed and when I noticed and when I noticed he’d noticed. My shirt was wet from my shoulder to my breast, then dry, then wet again, along with the top of pants. When he sat up and I was holding him, the diaper hadn’t come with up with him, and he’d piddled on me. More than a little, less than a lot. I’ve been peed on by my charges before. It’s nothing for either of us to get upset over. He looked mortified and turned his face away.

“Gordy … Gordy. Look at me.” I stepped to over where he was facing and put my hand on his cheek so he couldn’t look away again. “Gordy. Gordy, look at me. It’s okay. It’s fine. Deep breath, and then go blow your nose and wash your face. Okay?” He nodded again, a smoother motion that time, and I watched him shuffle to the hallway. “And please put your shirt back on when you’re done.”