The Best Babysitter in Town Ch. 5 (reposted) (Patreon)

“So,” I said, glad but also not to have the diaper change over and still trying to sound more confident than I felt. Gordy was naked from the waist down, flat on his back on his changing table with his feet in stirrups, leaving everything o so gloriously wide open. Awkward …

Bu also, somehow, it felt less awkward to go from diaper change to spanking than it would’ve been to go from ‘regular twenty-year-old in regular underwear’ to ‘naked and over my knee.’ Like, I hate to say it and I’ll never say it to Gordy, but as not normal as his being subject to his stepmom’s super strict discipline was, it seemed ever so slightly more normal for a 20-year-old boy still in diapers to be subject to his stepmom’s super strict discipline. Unfair as hell, and didn’t really make any sense, unless you think wearing diapers means you’re never really an adult, and I don’t think that. Anybody who does is just an ableist asshole.

“Need help sitting up,” I asked.

“No,” he said quietly. He followed it with a sigh. Poor guy. I really felt for him. Maybe I should’ve been as morose about the whole thing as he was, but I still thought if I treated it like no big deal, it would be over sooner, be easier, and not make the rest of the night so weird.

“Well,” I said with so much forced cheer it would make Martha Stewart in her salad days seem like a grinch, “hop down, and let’s get this over with.” I gotta say I was surprised Gordy didn’t try to cover himself. Maybe it was because he’s had his diaper changed by so many sitters and school nurses before that he just had no shyness left when it came to his nudity. I could understand that; after having a wet diaper changed, or worse, how big a deal was just being naked? Still, even though I’d just touched it and even though it would be pressed against my thigh in a moment, I would’ve appreciated it if he’d covered himself for my sake, if not for his, but of course I didn’t say anything about it. Poor little guy was having a seriously rough couple days; I wasn’t going to embarrass him anymore than was already inevitable in getting his butt spanked and into a clean diaper. And yet on the other than hand …

Yeah, I did find myself sneaking some furtive glances at it. I am a woman, and just because his was small didn’t mean I wasn’t at least interested enough to look. What it lacked in size, it made up for in personality (is my excuse and I don’t even know what that means). And I had no idea how Gordy’s problem worked. I didn’t know if I should’ve been worried he was about to pee on the floor, or for that matter if he just dripped constantly. And as for the little fella itself, I didn’t even know if Gordy’s problem meant he could even … ya know, feel that way.

I defaulted to babysitter mode and focused on two things. First, I had a job to do. Second, my charge was one unhappy kiddo. “Are you scared,” I asked him gently. He shook his head. “It’s okay to be scared. You can be brave and scared at the same time, right?” Not sure what point I was trying to make with that.

“It’ll all be over quick,” I said next, “and then we can go back to having fun together.” I think I’ve said that to kids who don’t like brushing their teeth too.

I eyed the hairbrush on the desk. I had never spanked anyone before. “Will you tell me how your stepmom spanks you?” I saw him wince like he just swallowed his tongue. Poor little guy! Ugh! I didn’t want to spank him. I wanted to hug the stuffing out of him. Sad boys, no matter their age, have a special place in my heart.

Gordy answered my question by stammering, “Um, ahem, um … she … uh …”

“Hey, it’s okay,” I said. I didn’t want to force the words out of him, and I didn’t want him to choke on words to the point of passing out, which he looked for a second like he might. “Let’s talk through it together. Okay?” He nodded without looking at me. “Hey,” I said again and put my fingers under his chin, lifting his eyes to mine, “this is just like your diaper change. You don’t need to feel embarrassed with me at all. It’s just one of those things, right? I’m still your friend, and I’m just here to help.” Of course, I’ve helped a lot of friends without once wiping down their genitals or smacking them on the bare bottom.

“Take a deep breath,” I told him. “Like this.” We took a couple deep breaths together. I needed them almost as much as he did, but I think I was better at hiding it. “Alright. That feels a little better already. Can you answer my questions?”

“Y-yes.”

“When you get spankings from your stepmom, does she have you bend over the bed or the desk?”

“She … p-puts me over her kn-knee.” And he stutters when he’s embarrassed or scared? He is so darling, poor little dear.

“O, that’s right. She said that. I forgot.” Odd as anyone his age being spanked is, the idea of being laid across a woman’s lap to have their bottom spanked just seemed so much more childish. But a spanking is a childish, and not that Gordy’s condition or what he wears is childish, but not being allowed to change his own diapers is childish too.

“Where does she sit when she puts you over her knee?” He pointed at his desk chair. Straight back, no arms. It actually looked like it would be uncomfortable to sit and study on, but I could see how an office chair on wheels would not exactly work for giving a spanking on, certainly not to an adult. We’d be rolling all over the place, at least until we tipped over and hit the floor.

I pulled the chair out, took a look at how much room that gave me, and turned it around so it was facing away from the desk. “I guess you need to be on this side of me,” I said. He was on my left, next to the changing table he’d just gotten off of. I’m right-handed.

“Um …” was his response. We were both saying a lot of that, but he was in the lead.

I waited patiently for him to say whatever he had to say before prompting him with, “Mhmm?” He turned away to reach for something under the changing table, and then turned back, red faced and looking at the floor as he handed me a diaper. “So not bare? Cuz she said to spank your bare bottom. You’re not trying to get out of …” I trailed off as I had the epiphany. “O! For my lap … okay. Do you, um, always wet when you’re getting your bottom spanked?” I took his silence for a yes. “Like, a lot? I don’t mean to … It’s just that you had a lot of coke, and your diaper was really full … so maybe it’s all out of you … or maybe not.” Hindsight being 20/20, I knew later I shouldn’t have done my thinking out loud.

“It’s … enough.”

“What is? … O! The diaper. Sorry. I promise I’m not really this ditsy. Just first-time jitters. Probably disappear as soon as we get started.” Which is when a little voice in my head said, yeah, that’ll make him feel better. Apparently voices in your head also have eyes they can roll. “Okay, so I’ll sit, and you come stand over here.”

I unfolded the diaper, and it was a lot bigger than the one I’d just taken off him. Quite a lot bigger, in fact. “This one is so much bigger. No way would this fit you.”

“I don’t, uh … th-those ones aren’t for w-wearing.”

“O.” That made sense. The bigger the diaper, the more coverage for my lap (and the floor). But exactly how often was she spanking him? So often she kept diapers on hand just to cover her lap, apparently. I glanced at the changing table, and there were a few of the big ones on the shelf with the other diapers. That didn’t tell me how often, but apparently she was spanking him often enough to keep at least a few of the big diapers in easy reach. Or maybe she liked having them out so Gordy would see them and remember to make good choices, sorta like hanging a paddle on the wall. Anyway, not important in the moment. I reached behind me and took the hairbrush off the desk.

Gordy blanched and rushed out, “That’s not …”

“Gordy, I already told you I’m going to spank you with the hairbrush like your stepmom told me to. Do you want to go to bed straight after your spanking?” Ah – there’s my confident babysitter voice. I guess I was right; once I got situated, I’d be just fine.

“That’s not … (sniff). I … (sniff).”

I put the hairbrush back down and stood up. “You poor dear. I bet you’re just a bundle of nerves inside, aren’t you? C’mere.” He needed a hug. You don’t get to be the best babysitter in town without learning to recognize when someone needs a hug. I see total strangers going about their business sometimes and can tell they need a hug. “Is this your first time getting spanked by someone other than your stepmom?”

He shook his head. “Mmm-mmm.” That’s interesting. I wonder who else has had him over their knee.

“So you’re just nervous? That’s okay. It’s okay to cry before your spanking.”

“It’s …”

He was having a hard time saying it, so I cooed, “Whatever it is, you can tell me.”

“She … starts with her hand first. Then the hairbrush.”

“O, you poor thing. And I was just about to … I’m sorry. You were just trying to tell me. I didn’t mean to scold you. Forgive me?” A poorly timed question. I may be the best babysitter in town, but cut me some slack. It was my first time babysitting a twenty-year-old peer, my first time changing a twenty-year-old’s diaper, and my first time spanking anyone at all. If I ever scold one of my normal charges for something they didn’t do wrong, I always apologize and ask the little tykes to forgive me. Guess we’d see in a few minutes just how forgiving Gordy is.

“Mhmm,” he vocalized. In all the years I’ve known Gordy, he’s never been tongue-tied, but I would certainly have had trouble answering my friend-cum-babysitter-cum-diaper changer-cum-disciplinarian too.

“What else do I need to know,” I asked. He didn’t say anything. “Does you stepmom scold you before she spanks?” He nodded. “Okay. I’ll do that too then. How many spanks do you get? Five? Ten?”

He actually let out a laugh at that as he shook his head, but not a ‘haha’ laugh, and then his brief smile disappeared. “M-more.”

“How many more?” I’d never given a spanking, hadn’t been on the receiving end since I was eight, and hadn’t even seen one since then unless you count paddling at sorority rush. As an underclassman, I hadn’t even wielded a paddle then, and as a good rush bunny, I never earned a paddling either. Two swats from one of those looks like it friggin hurts, but I had no idea how two swats from the paddle translates into hand and hairbrush spanks.

“Until she thinks I’ve learned my lesson,” is what Gordy said instead of giving me a number.

“Well, how will I know when you’ve learned your lesson?” I didn’t want to give him so few spanks he got in trouble with his stepmom later, but I certainly didn’t want to give him a beating.

“Until … until I cry.” I was wondering about that. I didn’t know if he’d cry or not. I mean, crying is what’s supposed to happen when you get spanked, but you’re not supposed to get spanked at all as an adult. Would a spanking at his age hurt enough for him to cry? Can adults even cry from pain alone? I guess I had my answer.

On the other hand, and I knew it was just nerves and a lot of bad feelings, he was already weepy, so tears wouldn’t be a helpful guide for me. “Sweetie, you’re already crying a little bit.”

“Harder.”

“Until you cry harder? Okay. You know I don’t want to, right?”

“Mhmm.” He seemed on the verge of crying pretty damn hard right then.

“What color is your bottom after a spanking? Pink?” He shook his head. “Dark pink? No? Red?” He nodded. “Really red?”

“N-no. Not r-really red, not for s-something like th-this.”

“Okay. I’ll do my best, and I’ll tell your stepmom you were very brave and cooperative and that if I didn’t do a good enough job spanking your bare bottom that it’s my fault and she shouldn’t spank you again. Okay?” He made a noise that I took to mean okay, or if not okay (cuz he really didn’t seem okay) at least assent.

I felt for him; I really did. He started out the week hoping to go on a date with a pretty twenty-year-old, and instead he was about to go across another pretty twenty-year-old’s lap to have his recently diapered and now bare bottom spanked til he cried. If he’d told me he enjoyed that very thing, it all would’ve made sense to me. I didn’t fully believe him when he said he didn’t, because it just wouldn’t make sense any other way.

I looked him over again. The poor little dear, so embarrassed by the whole thing that he couldn’t even answer my questions about how his stepmom spanks him and getting weepy before we even started.