The Best Babysitter in Town Vol. 2 Ch. 14

“I could’ve done this myself,” Gordy said to me for the millionth time from flat on his back on his changing table. “You don’t have to change me every time.”

Let’s see … What are some plausible reasons for why I change him when he can do it himself? It’s not because I’m faster at it; he’s had enough practice to win races. It’s not because he doesn’t do a good (enough job). It’s because … I like to. And why do I like to? Because at that moment standing over him, with him on his back and his feet in the stirrups all vulnerable and needing fresh pants, is as dominant as I feel with him any time except for when he’s over my knee. But I couldn’t tell him that, so I changed the subject by distracting him … by wiping his peepee with a baby wipe. Not in a sexual way; just in a diaper changing way. But I did say, “Who would you rather be doing this now – me or you?” And I might have given his boypart a gentle squeeze. I’m not a tease, but apparently I’m not above being a tease when it suits my purpose, like not telling Gordy I like changing him because I like the power dynamic it creates.

And not that my teasing him was doing anything to him that wasn’t already happening. I’m pretty sure he’d been hard since the moment I said I’d teach him how to kiss. He had a semi when I opened his diaper that threatened to become a fully when I was wiping him down. Good thing Gordy is small down there or I wouldn’t have been able to get his diaper taped up until he calmed down. I wanted to put him in one of his cartoon diapers, but I resisted the temptation; it would just be a waste putting him in such a thick diaper when his bath time was only a couple hours away.

“Just a sec,” I said when he started to sit up. “You sure you wanna do this?”

“Kiss?” World’s most adorable doofus; that’s my Gordy.

“Yeah. Cuz we don’t have to. If you aren’t ready or don’t want to, I need you to tell me.”

“I’m ready … And I want to …Not that I mean I … Sorry.” I would chalk up his nervousness to first-time jitters, but Gordy trips over his tongue and apologizes at least fourteen times a day. As for his eagerness, he’s gone twenty years without kissing a girl! Of course he was raring to go! I let him sit up.

“So, uh, here or your room,” he asked me.

“How about the couch? We don’t wanna get carried away with your very first make out session.” I added a condescending blink-plus-shallow-head-nod to that. Not sure why. I just didn’t want him thinking making out would lead to sex; as though sex is impossible on a couch or something? He started to put his pants back on. “You can leave those off.”

“Um, you sure? Just, making out with me in my shirt and diaper?”

“They’re just like undies, right?”

They’re not like undies. They cover the same things, but their function is entirely different. I just think Gordy looks cute in his diapers, and if him wearing no pants makes it easier get to second base, should we do that, then, well … I told myself after I put him to bed I’d have a serious think about whether I was fetishizing his disability and when and why I became such a slut. Pretty sure the answer to the why is dominance turns me on way more than the hottest vanilla guy ever did. That seems like the only reasonable explanation for why Gordy’s been getting happy endings with his baths … also why I’m bathing him at all.

“C’mon,” I said, taking his hand and leading him downstairs.

“Have you, uh, kissed a lot of boys before,” the derpy derp (but in a good way) asked me.

“You cheeky boy! First lesson, never ask a girl that again.”

“Sorry.”

“It’s okay.” We sat down.

“So … Did someone teach you how to do this?”

“Nope. Most people figure it out by trial and error … I did practice with a friend once.” And he went a little wide-eyed at that. What is it with boys’ fascination with women kissing?

“So, how do …”

Know what’s easier than talking Gordy through this? Kissing him before he can ask more questions. Lips closed.

“Did you like that,” I asked.

“Uh, yeah.”

“Wanna try it with our lips open?”

Imagine a very well-trained dog. The kind of dog that will sit perfectly still waiting you to throw a ball. Except you’ve gone full baby voice asking, Do you want the ball? Does the good boy want his ball? Huh? Does you want it? Is you my good boy who’s gonna play with hims ball? That very well-trained dog won’t be bouncing up and down like Tigger, but his tail will be wagging and he'll be struggling to keep his butt on the floor as the excitement builds. I give you Gordy’s reaction to being asked if he wanted to kiss with our lips open.

I leaned toward him. I didn’t want him to feel bashful about … well, he’s bashful about most things. I decided to initiate everything. He was tentative with his lips at first. Open mouth but no tongue.

I gave him a little tongue, and he almost moaned. I gave him a little more, backed off a little, and then … so much tongue, specifically his filling my mouth. I pulled away.

“Gordy, Gordy,” I repeated to get his attention. “Less tongue. Less can be more sometimes.” A girl’s gotta breathe and, ya know, not get slobbered on. And back we went to making out before he could feel like he did something wrong and apologize to me.

Gordy is so slender, in some ways he’s pretty. Not handsome; pretty. I was thinking of this while giving his neck some attention, slender like a girl’s. I thought about it again when my hand found his thigh. “Is it okay if I put my hand here,” I asked him.

"Mhmm." I mean, we’re talking the top of his thigh just above his knee, not the inside of his thigh, but better safe than sorry, especially since it was his first.

Pretty soon he discovered myneck, which attaches to my shoulder, over which was a bra strap, doing what bra straps do. He started going a little too far south, like he wanted very badly inside my shirt. Not that I blame him; just not on a first date and on his very first time getting physical with a girl. I redirected him.

Now, my hand was heading further north up his thigh. I didn’t ask him. I just moved it up a little and waited. Move it up a little more and waited. My fingers brushed the thin layer of plastic covering the outside of his hip. The whole experience had already been a lot more crinkly than any make out session I’d ever been a part of.

My hand found its way to his butt. Of course I patted it. Butts in diapers need to be patted; I don’t know why; I just give in to the urge. The butts of the people you’re making out with also need to squeezed, so he got one of those too. All the while, he’d kept his hands to himself. If he’d put his hand on my side or back or in my hair, that would’ve been okay with it. But if he put its anywhere else, I would’ve moved his hands. I wasn’t ready for it, and I think it would go better, Gordy being Gordy, if I talked him through it the first time he got past first base. I wasn’t surprised even a little that he kept his hands to himself completely. A boy who says he’s sorry as much as Gordy does probably isn’t going to anything for which he’s actually owe an apology, like putting his hands anywhere without consent.

“Ya know,” I said in his ear while he was buried in my neck again, “we don’t have to wait for bath time.”

And returning to our previous comparison of Gordy to a dog, his head popped up like he heard the clink of a leash around walk time.

“Really?”

“Wadduya mean ‘really’? Of course we can. You want me to?”

“Uh-huh.”

My hand went between his thighs. I had no trouble finding him through his diaper. It was so warm I thought he’d bad a big flood of an accident after all that soda he drank at dinner, but a glance down as his wetness indicator told me was just that hot-and-bothered.

“Does that feel good?’

Big Gordy sigh. “Yeah … Can we … Um, not in my, uh …?”

“You want me to get it out of your diaper?”

“Yeah, please.”

I’d given him an HJ in the tub only. Self-cleaning. Not that I expected a very big load (I was guessing Gordy isn’t stingy with the attention he lavished on himself), but I didn’t wanna clean it up, wherever it got. Pretty sure his stepmonster has an unspoken rule about no cumming on the couch. Which is when I had a vision of Gordy over my knee for cumming outside his diaper and discovered yet another scenario to log away in my increasingly kinky spank bank.

“Let’s keep it in your diaper this time. You can do that, right? Cum in your diaper this time, for me?”

He answered with an unspoken yes before I even finished that sentence. Even if I had wanted to take it out, clearly (if you were there, and I was) he’d have cum in his diaper before I could get it out. He bucked his hips a time or two; he moaned; and when I thought he was done, he said in mid-orgasm voice, “Keep going; it’s not all out.” Because it turns out with his diaper keeping his erection pointed down, it’s not, shall we say, a clear shot. Takes longer … Like, we should all be so lucky to have orgasms that last that long.

I felt him going soft through his diaper and stopped. I moved to the corner of the couch, put a pillow behind me, and patted the cushion in front of me. “C’mere.” My obedient adult babysitting charge scooched over and reclined against me; I folded my arms over him and gave him a kiss on his hair. “Did you have fun?”

“Yeah.”

“Are you sleepy now?”

“A little.”

“You’re a fast learner.”

“Really?”

“Yeah. And you didn’t give me a hickey, so bonus points cuz I don’t like turtlenecks.”

“Heh.”

Half a minute passed in silence. “Are you so quiet cuz you’re sleepy or cuz you’re thinking?”

“Not thinking … More like, wondering something.”

“What?”

“You know how, when you touch me down there, I, uh, it’s over kinda fast?”

“Everyone’s different. Fast compared to what?”

“Compared to when I do it myself.”

“It’s cuz you’re more aroused when I do it. You’ll last longer the more we do it.” New one for the spank bank: punishing Gordy for premature ejaculation. And another: punishing Gordy for cumming in his diaper. That’s right: I’m turned on by the idea of punishing Gordy for cumming in his diaper and the idea of punishing him for cumming outside his diaper. I … might not be a very fair dominant, at least some of the time?

“Did you …” I asked him and stopped. Hoo buddy, how to phrase this? “How did it feel through your diaper?”

“Different.”

“Good different or bad different?”

“Um, kinda both.”

“How’s that,” I asked in a perfectly nonchalant tone like we were discussing the sensory experience of cornflakes. That’s a babysitter best practice: asking a question you really, really want the answer to in a calm way.

“It felt good; not as good as without a … diaper. But when I came it took so long; that felt great.” He actually chuckled at that, as though the culmination of his first make out session was already a warmly lit, distant memory. I was unexpectedly proud of myself. I chuckled right along with him.

“And what was the not good part,” I asked.

“Um, it seems kinda silly.”

“That’s okay. You should tell me anyway, so I know if there’s something I shouldn’t do.”

“Well, I kinda … I was … disappointed? I think is the right word, when you told me to cum in my, um, diaper. Like it’s … not exactly … manly.”

“I think of you as a man no matter …” I decided that sentence didn’t need an ending. Adding where you cumwould’ve added way too much weirdness for too little benefit.

“That’s not all.”

“O; sorry; keep going.”

“When you told me to cum in my, um, diaper, I also kinda like it.”

Okay. Far and away the most interesting thing Gordy has ever said to me.

“Is that weird?”

“No, sweetie. It’s not weird … Why do you think you liked it?” Um, just asking to make conversation.

“I don’t know.”

“That’s still okay,” I rushed to reassure him. “Nothing silly about that. People like all sorts of things.” As a random for instance, I like submissive boys laying their pretty heads against my chest and telling me how the HJ I gave them made them feel. “When you said it’s not manly, do you mean it’s feminine, or like it’s not, like, macho?”

“Like, a real man doesn’t cum in his underwear.”

“And you liked and didn’t like that at the same time?”

“Yeah, for some reason.”

“Did you maybe like it because you didn’t like it? Does that make sense?”

“ … I think that makes sense. Maybe that’s why I liked it; I dunno.”

I had an evil genius thought. I have a lot of those around Gordy; I usually keep them to myself. I wanted to tell him he’d be in big trouble if I caught him masturbating outside his diaper and see if he smiled or blushed or both. Way too much way too soon; I kept it to myself.

“If you think about it some more later and want to talk about it, that’s okay. … I really like that you’re so open and honest about your feelings. Takes a little bit of prying sometimes, but I like that you share with me. I hope you like it too. You can always tell me anything.”

“I do; it’s not always easy, but it’s easier to talk to you then anyone else.”

Never felt so special in my life.

I would’ve been content to keep cuddling, but for some random reason I remembered right then something I learned in health class: when a boy gets an erection, his prostate moves to block his bladder so he doesn’t pee when he cums. That’s why boys can’t pee when they’re hard. And after they cum, the prostate moves back to its normal position, and they can pee again. Just a thing I remembered while the diapered boy who drank his volume in soda at dinner laid against me coming down from an orgasm.

I could feel warmth against my thigh. I reached for his diaper and gave it a pat. “You are getting more and more soaked by the second.”

“I had to pee the whole time we were, ya know.”

“You could feel it?”

“When it’s that full, yeah, I can feel it. I can’t do anything about it, but I can feel it.”

“Your diaper isn’t going to last much longer. You want me to double diaper you for a bit, or go get in the tub?”

“Tub. I’m gonna have to shower after my bath.” I took that to mean he’d be peeing quite a bit in the tub and would need to rinse offer. Maybe one day I’ll get in the tub with him, but not when he’s a fountain.

“Up,” I told him. He got up, and I did a quick check of my pants and the couch. He hadn’t leaked.

“Can I ask you something,” he asked me on our way up the stairs.

“Sure.”

“This weekend, do you think you could teach me about, um, girls? I mean, um, how to, uh …” Gordy, ever bashful but a lot less so mere minutes after his first make out session.

“Are you asking me for an anatomy lesson?”

“And to, um, do for you what you did for, uh, me; show me how, I mean.”

Plus 1 for the spank bank: training Gordy how to pleasure me. His diaper may have been soaked, but my underpants weren’t exactly dry. I really did mean it when I said I liked how he was so open and honest with me (albeit with plenty of prompting). It told me he was trusting me more and more, that he understood better and better what I meant when I told him he’s safe with me. It meant he needed me, or at least that he got something important from me beyond the physical and might one day need me. I don’t think there’s a better feeling than being needed.

But it also worried me. I couldn’t expect him to always be open and honest and never be open or honest with him. I knew eventually, and probably not very far away (like, maybe that weekend), I’d have to tell him how certain things about him made me feel.