The Best Babysitter in Town Ch. 9 (reposted with photos)

“Let’s get you into a fresh diaper,” I told Gordy as the twenty-year-old stood awkwardly wrapped in a towel. “Which one do you wanna wear?”

“Those are for bedtime,” he said and pointed sheepishly to the thickest diaper under his changing table. I never thought about daytime diapers versus nighttime ones before. The ones for babies and toddlers don’t really come in different thicknesses, at least not that I’ve seen in all the babysitting I’ve done. I’ve double-diapered one particularly leaky tyke, but all the parents I sit for just have one go-to diaper for their little ones. There were four kinds under Gordy’s changing table, three if you don’t count the kind that, apparently, are just for when his stepmom puts him over her lap for a spanking.

“Lemme lay your diaper down first.” I unfolded it and spread it on the table. So much easier than having him lift his hips. “There. Up you go.”

He looked at me awkwardly, as though I’d forgotten something. He really needed to learn to use his words. I mean, I get that having your diaper changed by a babysitter at twenty must be mortifying, but it would be a lot less so if he would just talk through the awkward parts rather than let silence make them even more awkward. I decided to just tell him as much.

“Gordy, do you have something to say?”

“Um, my, uh … towel.” Shouts the ‘C’ word across campus but can’t ask me to take his towel off or, ya know, just do it himself. Silly boy. Maybe he’d finally discovered his modesty or something … one hour of nudity and a handjob later.

“O! Of course. Here.” I took his towel off, which left him head-to-toe naked in his bedroom. I tried inconspicuously to look at it, and I think I succeeded as I draped his towel over the back of his desk chair. Not really sure why I looked, other than wondering if he was hard again … and maybe thinking his is cute. “You can just say ‘I’m still wearing a towel,’ Gordy. You don’t need to get all shy and quiet again. Up up.” Didn’t really mean to say that last part; I say up up when talking to my dog or tiny tots, and it just slipped out.

Gordy got onto his changing table and laid back, and I looked at the tray under it and found what I was looking for: nursery cream. “Do you use this at night?”

“I, um … every change, at least at home.”

“Good. You should. I didn’t know they made special brands for adults,” I mused as I read the label. “‘Change wet and soiled diapers promptly. Apply liberally at bedtime and anytime exposure to wet diapers may be prolonged.’ Huh; says the same thing on Desitin.”

Gordy being the biggest boy I’ve ever diapered, I figured it would take more than two fingertips to get his diaper area covered and used a nitrile glove again. “I know this is awkward,” I told him, “Sorry.” Though in what way it was awkward considering I’d just rubbed him all over down there with a bar of soap, I don’t have words to explain.

I probably should’ve put on two gloves, not to keep the cream off my hands, but because it was somehow weird to be handling him down there so much without one. I’d just washed his diaper area and given him a handjob, short as it was, but there was water and soap and … it just hit different. Not that he seemed to be hating it.

“You’re a squirmy little thing,” I chuckled at him. He furrowed his blushing brow and settled down. “It’s okay,” I tried to reassure him, “I know that probably feels really good. Lift and turn a little for me.”

The redness I’d put into his butt for him was already fading just a little, but there was the unmistakable outline of the rounded end of the hairbrush on one cheek. I felt guilty. I didn’t mean to bruise him, if that was a bruise.

“Maybe this will feel good,” I said and tried as gently as I could to rub the cream into his butt. He flinched. “Sorry. Does that hurt?”

“A little. Just cold.”

“Poor thing. I’m sorry I had to spank you.”

“I know.”

“But I’m not sorry I got to spend the evening with you. Believe me?”

“Yeah.”

“Is that a smile? Are you smiling at me? You’re cute when you blush.” Boy did that make him blush even harder.

I took the glove off and dropped it into the diaper pail, still legit impressed with the changing table he’d built. When I looked up again, he was peeing into his diaper. More than a dribble, but his diaper was getting all of it. It reminded me of a drinking fountain with low water pressure. I looked up at his face to see if he was registering that he was wetting at all.

His eyes were squinched shut, and he opened them to see me trying to read his face. “S-s-sorry,” he stammered.

“Don’t be sorry. So you can feel that?”

“I c-can feel it getting w-warm.”

“All the time?”

“N-not always, but with my diaper open.”

“O. Let’s fix that and get you all taped up.” I folded the diaper over him and taped it. “We’ll change you again before bedtime.”

“S-sorry.”

“Gordon Rooney, if you apologize to me one more time, I’m going to put you in timeout,” I said in a very lighthearted way … that once again went right over his head. I don’t think he saw me rolling my eyes – reflex, couldn’t help it. “You silly boy. Sit up.” I held out my hands and helped him up.

“Look at me. Are you listening? You don’t have to be sorry for things you can’t help, okay? I’m here to help you with these things. You’re not in any trouble with me. you don’t need to be shy about your diapers or anything else. Okay?”

He nodded.

“Now, hop down, and let’s get you in your jam-jams, and we can go downstairs and find a movie.”

“I can get my pajamas on myself,” he said in a tone that was almost condescending. In fact, it was. Like he was patting me on the head and reminding me he’s capable of doing everything I’d done for him (except his spanking, presumably) by himself.

“Sorry. I didn’t mean …”

“I know.” He got down off the changing table and picked up the pajamas he’d taken off earlier. Or rather the shirt he’d taken off. I’d taken his pants down for him.

“Diaper on well? Not too loose or too tight,” I asked when he bent over to put his pants on.

“Um, no. You did a good job.”

“You don’t get to be the best babysitter in town without changing a lot of diapers. Not that you’re a baby.”

“I know what you, um, mean.”

“Come here,” I told him.

“W-why?”

“O, just come here, you silly boy.” He shuffled over, and I just put my arms around him. “You need a hug.”

“I do?”

“Of course. One when you’re not crying and rubbing your butt. You’ve been very brave tonight. Thank you for being my helper and making things easy.” His stepmonster, unfortunately, has him well trained.