The Best Babysitter in Town Ch. 6 (reposted with photos)

“Okay, let’s get this over with.” I kept a gentle hold on his wrist and led him the few feet to the right of the chair before sitting down and spreading the diaper he’d handed me across my lap to catch any piddle. I took just a moment to consider how I wanted to scold him.

It felt odd to do it with me sitting and him on his feet standing over me, even though he’s so short he was only a little taller than me seated. Having him sit on the floor or get on his knees just seemed silly, and anyway, that would just be degrading. And then there was the fact that this incontinent twenty-year-old boy had been undiapered for several minutes and counting. Not knowing how his condition worked, I’d feel a lot better knowing any accidents (are they accidents if you’re incontinent? Is ‘mishap’ a better word?) that might happen would end up in the diaper across my lap and not on the carpet (or me). So I opted to scold him with him across my lap.

“Okay, Gordy, get over my knee.” He started to bend down, and it seemed awkward for him. It was kind of obvious he was trying not to touch my leg, considerate but also ironic considering how much of him I’d already touched and how much and what parts of him were about to be pressed against those very same legs of mine. “You can put your hand on my thigh. You won’t hurt me,” I told him, but I think he wasn’t worried about whether I could support his weight; I think he just felt bashful about touching a woman’s thigh. I didn’t know if he ever even had a girlfriend.

I helped him across, and once he was over my lap, I tried to assess whether he was in the right spot, but I had nothing to judge it by. I glanced from my hand to his butt, which was pretty cute. Just sayin’. If he didn’t wear diapers all the time, I for sure would’ve noticed what a cute, round butt he has. Anyway, just going from what seemed comfortable for me, I told him, “Scoot forward a little more.” He did; at least he’d stopped sniffling. His weight across my thighs didn’t feel as heavy as I thought it would, but then he’s not a very big person. Maybe five-foot-six and thin-framed. He didn’t play sports in school. Maybe he wasn’t interested in them; maybe he didn’t want to play in his diapers; maybe whatever reason he was in diapers is why he couldn’t play. Anyway, he wasn’t muscular or heavy, and he was positioned for me to comfortably spank his bottom.

When I’d swatted him on his diaper in the kitchen, it had turned me on. Just the feel of it, the power. This boy – twenty-years-old, actually a couple months older than me, who I’d known since kindergarten and now went to the same college with – was under my control. And now, having him across my lap, I felt that same control times about ten. It wasn’t just that I was about to spank him for real. In fact, inflicting pain was a downside; I didn’t want to hurt him or cause him pain or even do this at all. But I was about to do it, and that sense of arousal came from his having submitted to me. In the kitchen, I’d taken him by surprise with those swats. In his bedroom, he’d laid across my lap when I told him to, and in a moment, I’d hold him down with my left arm and redden his butt with my right hand, and he'd just take it. He’d even believed it was good for him even though he hadn’t done anything wrong, and maybe he was right. Maybe it was good for him, which was the only reason I was doing it, my arousal being a surprise to me and not something I’d even thought of before. It was distracting, actually. I needed to focus on giving him his consequence and how he was feeling, not how I was feeling.

I reached between his legs and pulled the back of the oversized diaper up to see how much of him it would cover. I knew he was going to wet, or ‘leak’ might be a more appropriate word, during his spanking, and if he really let go (opened up?), it was good to know the diaper under him would at least keep him from getting me wet if I was quick enough to pull it up. I’ve been peed on by some of the tykes I’ve sat for before; I knew how wet a toddler could get me, and so I knew how much wetter Gordy could get me. Yikes.

There was nothing else to adjust, so I pushed the diaper back down out of my way but still ready if needed, and I got ready to give my very first pre-spanking scolding. I’ve scolded some of the kids I’ve babysat before, but aside from them being actual kids, that was never for something they’d done before I got there. I didn’t even think Gordy had really done anything wrong, but I opted to focus on the principle of the thing and scold him as though he needed to be scolded just like I was going to spank him as though he needed to be spanked.

I started out like I do every pre-consequence scolding, with, “Do you know why you’re getting this consequence?”

“Because I called someone the ‘C’ word,” the already sorry twenty-year-old boy across my lap replied.

“That’s right. What she did was inexcusable. She and her friends should be ashamed of themselves, and I can’t even imagine how you must’ve felt when she laughed at you and told everybody on TikTok you wear diapers. You have every right to be angry, furious. But you called her a very ugly word. Some people even consider it a slur. Your stepmom is right that if you ever got recorded saying it, it could haunt you for the rest of your life, and even if it didn’t, it’s not something you should say when you know your stepmom feels so strongly about it.”

I mean, it is an ugly word. That girl totally deserved to be called it, and I wasn’t about to say otherwise. If his stepmonster had any point at all, it was only that it really would haunt him if he got recorded saying it. As for the word itself, I wasn’t going to tell him not say it because I’d said it since I got there, a couple of times in fact, and meant it. And that was just out loud. I’d called his stepmom that word a few more times in my head, so if he made any mistake other than losing his temper (and he was pushed to it; shoved, really), it was saying it when he knew if his stepmom found out she’d give him a bare bottom spanking.

As was, since she was going out someplace all fancy, she’d misled me into coming over to babysit and was paying me to spank him for her. If Gordy hadn’t consented to this consequence from me specifically, it wouldn’t even be happening and the most awkward thing the two of us would’ve done all evening was change his diaper.

But he did consent to being spanked and spanked by me; he sort of even asked for it even though he didn’t think he’d done anything wrong to earn it, just submitting to it anyway on some weird principle that being accountable and disciplined was somehow helpful to him. It was somehow oddly cute of him, but I wasn’t thinking about that right then.

It was my very first time spanking anyone, and even though I’d literally just wiped his butt during his diaper change, I hesitated just putting my hand on his butt as I wrapped up his scolding. “Do you understand what not do in the future?”

“Yes.”

“Do you understand what’s about to happen because of the choice you made?” Choices, actually, of which using the ‘C’ word was only the most recent that led to him being over my knee. Not that I was spanking him because he chose to be spanked, but if making good choices was the universal lesson, maybe at some point he should consider whether choosing to give his stepmother the reins on discipline at his age was a good choice or a bad (very bad, stupid bad) choice. Hmmm.

“You’re going to spank me,” he answered.

I don’t know where the words came from. Maybe just instinct because, like I said, my first time giving a spanking, but I just let my response come out naturally. “That’s right. I’m going to give you a good, hard spanking on your bare bottom. I don’t want to, Gordy, but it’s for your own good. It’s okay for you to cry, and don’t worry if you have an accident on my lap. That’s what the diaper is for. You use this time over my knee to think about your actions and how you’ll make better choices in the future.”

And … damn. Too bad there wasn’t more to say. I was actually starting to feel confident with the scolding part. Now I just had a boy to spank. I put my left hand against his outside hip and help him firmly, raised my right hand, and hoped I’d have him red-bottomed and crying hard quickly just to get this over with.

Spank.

I looked at his butt and at him and tried to discern a reaction. I didn’t even get an ouchout of him. I got an adorable bottom wobble, but all I accomplished was teaching myself I’d have to spank harder (and that this would definitely hurt my hand). The very last thing I wanted was to spank Gordy and then have his stepmom decide I didn’t do a good enough job and give him get a second spanking after his morning diaper change the next day.

Spank.I guess spanking is a pain that builds up, at least for a twenty-year-old. The poor little guy had been sniffling in my arms a moment ago just from the embarrassment of what was about to happen, but two spanks in and he hadn’t reacted verbally or physically at all. But then, he’s a grown up. I know a little kid would probably already be sobbing, but Gordy, as weird as the whole concept is, is a grown up and, I realized, needed a grown-up spanking.

Spank. Spank. Spank. Spank. Spank. Spank.

I got a steady rhythm going, a regular pattern of spank after spank landing once a second or so, and I tried to vary where I was landing them. I kept one eye on where my hand was landing and another on how he reacted, and that’s how I figured out I could more bang for my buck (spank for my effort?) if I spanked a few times in the same spot before moving on instead of going from cheek to cheek.

I thought I’d count them out as I went, but I quickly lost count and paid more attention to how he was reacting, just like he said his stepmom does, to gauge whether the lesson was getting through, which I guess means if his spanking as hurting him enough. I don’t know about the lesson, but I could tell Gordy was getting uncomfortable as I heard first a few sharp intakes of breath, then barely audible grunts, then quiet ouches.

His bottom wobbled under my hand as I spank-spank-spanked away and turned his butt from pale, never-outside-a-diaper white to a lighter and then darker pink. That also helped me know where I was spanking him, and I kept my hand moving to make sure I was spreading the spanks out, giving four or five or six spanks in one place and then giving four or five or six in another, trying to mix it up so I got the whole spankable part of his bottom, from the top to the roundest part of his cute boy bottom to where it became his thighs. That spot, where his butt met the backs of his thighs, is where he reacted most to my spanks. I focused most of my attention there, thinking that was the quickest route to lesson learned since I, and I think he, just wanted this over with. Out of curiosity, I landed my hand on the back of his thighs, one each, and got a sharp hiss both times.

I was starting to think I had a knack for spanking twenty-year-old boys as his ouches and ows grew and then were accompanied by sniffles. I had started out thinking it would take a lot to make an adult cry, and I couldn’t know what he was feeling, but judging by the color of his bottom and how much my hand was hurting, I knew he must be hurting too. I nearly got lost in what I was doing, almost – but just almost – not noticing the oversized diaper protecting my lap had grown warm. Not a lot, but just a little in a spot against my thigh. He’d told me he wet during his spankings, often enough that his stepmom buys diapers too big to fit him just to protect her lap when she puts him over her knee for a bare bottom spanking. Sure enough, the diaper was needed.

“Almost done,” I reassured him, and funny thing was I’m the one who probably felt the most reassured. In half a spanking, I’d gone from nervous first-timer to knowing I could give a sound bottom warming even to a twenty-year-old classmate that would lead to sniffles in just a couple minutes. I knew he only piddled because of his problem, but even the thought that I’d made him wet himself made me feel powerful and confident, even if it wasn’t true and I would never, ever actually try to make him do that.

I reached behind me to his desk and picked up the hairbrush. He’d gone along with the spanking his stepmom had insisted on and hardly tried to get out of it … until I told him to go get the brush. That’s when he tried a little harder. But when I picked up that brush, about to put him over my knee, that’s when he really got upset. Funny – I would’ve thought he’d want to have it over with as quickly as possible, and I figured a brush is the quickest way to a lesson learned and a remorseful boy, but he’d rushed to tell me he always gets a hand spanking first. I’d never been spanked with anything except a hand, and that was just a few swats. I fact, I’d for certain already given him more spanks in a minute and a half than I’d gotten in all my twenty years.

He wanted to get it over him, but apparently not so much that he wanted to go straight the hairbrush, which told me a hand spanking plus a hairbrush spanking must somehow be better than getting spanked with only the brush, which made me wonder just how much the brush hurt. It wasn’t like he was pain free after the hand spanking I’d just given him. Confirming just how much he dreaded the thing, instead of a sigh of relief when I stopped spanking him with my hand, the sound of the wooden brush against the wooden desk as I picked it up provoked a sob from him that I both heard and felt.

I wondered just how powerful an item I was holding. It made me tentative, and I gave him what I thought was a light spank compared to how I’d been smacking his bottom with my hand, and I got a gasp. I’m a very nice person and even nicer babysitter, and I reflexively wanted to ask Gordy if he was okay, but even as a first-time spanker, I knew spankings are supposed to hurt. Doesn’t everybody?

The spot I’d spanked right away turned either the darkest shade of pink or the lightest shade of red. He said his bottom was supposed to be red, or at least it’s red when his stepmom spanks him, and trying to replicate that first hairbrush spank, I spanked him with it again. SPANK.

I got a sob. SPANK.I got another. SPANK. I got an “Ow,” the word wobbling just like his bottom. I recognized that verbal wobble, the voice of someone about to cry. That was the goal, as much as I never wanted to spank anyone and especially not Gordy, who was already having one of his worst weeks ever. But the sooner he had a red butt and tears running down his cheeks, the sooner his spanking would be over. I’d started out intending to get it over with quickly and so we could get on with our evening, but looking at the bottom over my lap and the boy it was part of, maybe I’d been naïve to think he’d be in anything like a mood to have fun after, or even be capable of it.

SPANK. “Hhh!” SPANK. “Ah.” SPANK. “A-heh!” SPANK! “A-heh … (sniff!) A-heh …” SPANK! “A-heh-heh-heh-hehhhh.”

It started as a low moan, a sound he did his best to hold in, I guess because of pride because he knew his spanking wouldn’t be over until he cried. He’d told me so himself, but I guess he learned long ago not to try to get away with crocodile tears.

But only one more SPANK! With the brush and I had a crying boy over my knee.

A lot of people think sobbing and crying are the same thing, but they’re not. Any good babysitter knows that. You can sob without crying and cry without sobbing. If one of my charges sobs, their little diaphragm cramping as they try to catch their breath, maybe a tear or two falls, but it’s over pretty quick. If a few tears roll down a kiddo’s cheek without any sobbing, I can patch up that hurt feeling or skinned knee pretty easy. But sobbing with great, big, fat, real tears rolling down those cheeks, with the heaving chest and (more often than not) the runny nose and snot? I may be the best babysitter in town, but that kiddo is going to be crying for a bit. That’s not a hurt feeling you can shush away with a soft word or a booboo that just needs a kiss. That’s a little one who needs a good cry, and across my knee was a twenty-year-old little one who needed himself a good cry.

And I made him do it. And his stepmom and that bitch on campus, but I was what tipped him over the edge. Again with that feeling of power, a rush that made me tingle, but also, I just felt so bad for him. I doubted very much his spanking hurt me more than it hurt him, but it was close.

But tears weren’t quite enough. How would I know when his spanking was over? Or how did his stepmom know, according to Gordy, so that I would know? A crying boy anda red bottom, and some of his bottom was still pink, a dark pink but not yet red. I wanted it to be over with. Heck, I didn’t want to do it in the first place, but when the stepmom says her twenty-year-old stepson needs a spanking, and even the stepson basically agrees, maybe he really does need a long, hard, bare bottom spanking, and I was the authority figure who had to give it, even if we grew up together. Some consolation that being an authority figure to a peer tickled a spot I didn’t even know I had.

I finished off Gordy’s spanking with ten SPANKS! hard enough to make Gordy kick his legs, arch his back, and emit a high-pitched noise I didn’t think boys his age are capable of making. For a moment, I thought I might lose hold of him, and if the tenth SPANK!!!didn't bring his consequence to a close, I probably would have needed to readjust him before he kicked and bucked his way right off my lap. We started with his toes just kissing the carpet, and we ended with them clear off the floor.

I set the brush on the desk and started rubbing his bottom. I would’ve let him up, but he didn’t try to get up; he seemed like he needed a moment to just lay there limply and have his cry. We’ve all been there; for me, it’s after a Lifetime movie or a bad breakup, but Gordy needed his good cry after his spanking from his babysitter, and I let him have it while gently shushing him and lightly rubbing his bottom for him. His pajama shirt had ridden up, and I rubbed his back for him too. Such soft skin, no big muscles. Looking at him, from his thin back to his red bottom down his slender legs, he seemed almost pretty in delicate sort of way.

I felt that warm spot on my thigh grow warmer and larger, and I remembered in the nick of time this boy wears diapers and reached over to fold the diaper over his bottom, keeping his accident off me and the floor.