The Best Babysitter in Town Ch. 10 (reposted with photos)

“You’re handsome when you’re cleaned up,” I complimented him. It was sincere too. He’s not hot beach bod guy, but he’s got a definite boyish charm with the baby face and slender frame. The thick bedtime diaper bulge in his pajamas made him look even more slender and small. I could see his diaper bulge earlier when I first arrived and he was standing in the corner, but it was just a square shape where his butt should be. With his nighttime diapers on, he looked like he had an old throw pillow under his pants.

“You’re, um … thank you.”

“Awww, did I embarrass you? You are handsome. Kind of a cutie, actually.” He’s so dorkily adorable when he blushes and smiles and tries to hide it. “Shall we take our date downstairs,” I asked, and while most of what I’d said to make him turn red just came out naturally, that was on purpose. I thought it might make him feel better, and he did smile (and try to hide it again). So cute! I seriously wanted to pinch his cheek and I have no idea why.

We went to the kitchen, and he made us a snack while I fixed us a couple sodas. It was only a few minutes past eight o’clock. I don’t know if I’m just really efficient or maybe I’m not efficient at all, but I got my twenty-year-old spanked, bathed, diapered, and in his jammies in just over an hour. O, and he came. So … the very model of efficiency? I wanted to ask him how long it took his stepmom to do all that, minus the HJ, but that seemed a little too familiar. Odd, considering just how familiar I was with him after all that.

Instead, because I can be just as much of a doofus as Gordy, I handed him his glass and remarked, “So you must be a pretty heavy wetter at night.” At least he didn’t do a spit take.

“Um, uh …” I’ll give him credit: that seemed like an appropriate response to a question I shouldn’t have asked.

“Sorry. I’m just … kinda interested. I think the oldest kiddo I’ve ever diapered for bed was five. I wanna understand more about your condition, that’s all.”

“I … like what?”

“Can you feel when you’re going?”

“M-mostly … It depends. I can feel getting warm, and sometimes feel I’m going.”

“You just can’t stop it. Can you start it on purpose?”

“N-no.”

“And you … Number two, too?”

“I can f-feel that e-every time.”

“That must feel strange.”

“I wouldn’t have anything to compare it too,” he chuckled.

“There you go! At least you can laugh about it. You were born with this problem?”

“Mhmm.”

“You’ve always been so mature about it. I think that’s really cool.”

“Thanks.” He is seriously one monosyllabic twenty-year-old.

“And,” I said suggestively because, I admit, I wanted to stir the pot. “At least you can feel other stuff down there.” Crimson to the tops of his ears. “Did you enjoy that?”

“Mhmm. Uh, guess I’m not a virgin anymore,” he answered, looking extremely pleased with himself.

“Well …” I opted not to break the news to him that an HJ doesn’t count as losing his V Card. “What should we watch?”

We turned on Friends, always an easy choice. The nineties aesthetic is … so many sweater vests and high-waisted jeans. It kinda works, I guess. And a little someone was surreptitiously (or so he thought) inching closer to me on the couch. Wonder what bad movie he picked up that move from. He was mere moments away from faking a yawn and putting his arm around my shoulder, silly virgin boy.

“O for goodness sake, c’mere.” I rearranged myself to make room for him and patted the cushion right next to me. That same derpy smile he was wearing after I helped him cum in his bath reappeared, not unlike the way my dog looks at me when when I let him on the couch. I put my arm over his shoulder. “Comfy?”

“Mhmm.”

“You just needed another hug, is that it? Such a hard week.” A few minutes later, I found myself absentmindedly playing with his hair, and he was resting his head on my shoulder.

An hour in, I reached over to check his diaper through his pajamas. As I did, he turned his head toward me and buried his face in my shoulder, and if I’m not mistaken, he gave me the tiniest kiss on my neck. Not sure what he was expecting, but, “Easy there, little fella. Just checking your diaper.” He sat up straight and inched a little bit away from me, making a face like he was more humiliated than that at any point since I’d walked in the door, which was saying a metric fuck ton. “Don’t be like that. It’s okay.”

“I thought …”

“I know what you thought, Gordy. It’s okay. You just misread my signals.”

“You’re not mad?”

“It’s an understandable signal to misread; I was reaching down there.” The boy wears diapers! Kinda have to check if he’s wet. Just sitting next to me with my arm around his should was, not counting the tub, obviously the most intimate he’d ever been with a woman. “Just making sure you don’t have soggy britches.”

“O,” he said like a puppy who’s just been told he has to stay outside in the rain and with a look on his face to match.

“You’ve never made out with a woman before?”

“N-no. I … No.”

“A lot of firsts for both of us tonight, but why don’t we save that for next time.” Wow did I regret that. Not saying that there’d be a next time but implying their would be making out.

“Next time? You mean, um … sitting for me again?”

“Yeah. Don’t you want me to be your sitter again?” I’m kinda the best in town, and surely more fun than his step-aunt or whoever looks after him when he’s in trouble. And this was a lot more interesting than the normal Friday night job for me, plus even after splitting the proceeds with Gordy, I made a lot more money.

“I guess,” he said.

“You guess? You’re gonna hurt my feelings, Gordon Rooney. I’ve had a good time with you.”

“You … Really?”

“Yes. Other than having to spank your bottom for you, I’d say we had a very pleasant evening, wouldn’t you?”

“I … Yeah. I’ve had … You’ve been very nice about … everything.”

“And you’ve been very cooperative. I don’t know what kind of trouble you were getting in before this arrangement– is that the right word for it? – with your stepmom, but you’re a very good boy, Gordy.”

“Do you hafta say it like that?”

“Like what?”

“Calling me a good boy.”

“O. You don’t like that?”

“Kind of childish.”

“I thought … But don’t you wanna be my good boy?” Boys are so easy to manipulate; they all wanna be my good boy, and all I have to do to get them to cooperate is sound the slightest bit disappointed and bat my eyelashes at them. “I see that smile you’re trying to hide. It’s okay. But I won’t call you that if you don’t want me to. At least not all the time.” I winked at him, and he practically melted.

“May I please finish checking your diaper?” He made the smallest nod, and I scooched over to him. “Stand up for me.” He did as he was told, and I pulled his pajama pants down to his thighs. I knew he was wet cuz he did it before I even got him taped up, and I could see that he was wetter. I just couldn’t tell if he needed changed. I cupped the front of his diaper to feel just how wet. “Turn around for me.” He wasn’t wet at all in back. I leaned forward and give him the ol’ sniff test.

“Hey,” he said and jumped forward. “I told you I know when I do that.”

“Do you know every single time? Even when it’s just a little?” His blush answered the question.

I sat up and pulled out the seat of his diaper a little to peek inside. All I found was a spanked butt. I pulled his jammie pants up. “Nothing that can’t wait until bedtime.” I gave him two firm pats on his butt that made him flinch. I don’t know what it is about butts in diapers, but it’s like there’s a primordial need to pat them.

“What? I didn’t though.” That was definitely a plea.

“I just meant you’re wet, silly. No poopies.”

He went, “Hmmph!” as he sat down. Again with his being adorable without meaning to. Ugh!

“What?”

“You keep using toddler words.”

“I don’t mean to. What do you normally call it? A dirty diaper? Messy? Stinky? Mushy? I’ll call it whatever you want.” As if any of that was better.

“S-soiled.”

“Soiled? Okay,” I said skeptically.

“What?”

“It’s just … that sounds like what they’d call it in a nursing home. Is that really better?”

“Like any of them are good,” he shot back. Boy had a point. But I’d rather be cute about it and call it a mush tush or say he fudged his huggies or packed his pampers, or even lumped his luvs than say ‘soiled.’ It sounds so dirty and old and helpless. He’s not helpless, and between being talked about like a toddler or an invalid, toddler seemed better.

“Anyway, sorry. I’m just trying to treat it like it isn’t a big deal. Just like anyone I sit for who’s still in diapers. Isn’t that better than fussing about it? Just the words that come out naturally for me.”

“Well, I’m not a toddler.”

“Gordy, look at me.” He did, which is funny cuz when you do say that to a toddler, they usually refuse. “I don’t see you like a toddler.” I winked. He tried to hide a smile again. Boys really are so easy to manipulate, especially the virgins. “Anyway, what were we talking about?”

“You … coming over again.”

“Right, babysitting again. Of course I want to. Do you ever have a babysitter when you’re not in trouble?”

“Not really.” I wondered what that meant.

“Well, maybe ask. And we can just do stuff as friends. We can go out and do stuff, or we can stay in. I like you.”

“Do you … like like me?”

“Heehee. What? Do I like like you? You are too cute. How about we say I feel affectionate toward you. You’re a sweetie. Most of the boys I know are definitely not.”

“Which do you like better?”

“Between a sweetie and not? Something in the middle.”

I wasn’t writing off the possibility of one day having romantic feelings for Gordy. I definitely had friendly, big sister feelings, and this weird, new-to-me feeling of liking how submissive he was. I for sure enjoyed smacking his butt, except for the making him cry part, and I even liked giving him that HJ, even though his equipment wasn’t exactly goals for me.

And I understood that Gordy was probably dying for female attention. Twenty, never been on a date let along been with a woman intimately. I had a feeling he’d had more orgasms in his diaper than out of it. And maybe, actually a lot more than maybe, he just needed a friend who would treat him normally. I hadn’t exactly done that, but I was over there as his babysitter, not as his friend.

“Turn around and c’mere,” I said to him. It sure was easy, too easy, to order him around without meaning to.

“You just checked me.”

“I know what, silly. Just turn around.” I leaned back against the arm of the couch and opened my arms. Now he understood, and he did he was told, leaning back against me and letting me put my arms over him.

And why? Because Gordy needs more hugs, I like giving him hugs, and he’d had an awful week. A hug from the babysitter is a good way to end it. Plus, I often do this before bedtime when I babysit, especially if it wasn’t the smoothest evening. It helps calm the little tykes down and gets them ready for sleep.

“You have a lot of feelings to talk about,” I said to him. “We can do that, whenever you want to.”

“You don’t have to do that. I’m not a pity case.” Funny how he said that while making zero – zip, nada, zilch – attempt to sit up.

“I know that. I want to though, if you want to. That’s what we do for friends. Can’t I be your sitter and your friend?”

“Yeah.”

“My sweet boy.” I kissed his hair without thinking – babysitter instinct; I guess I do that to a lot of my little charges around bedtime – and I swear I felt him sink deeper into my lap. “I’m so mad at your stepmom, but also glad she called me.”

We both started to nod off, which was the cue for putting him to bed. I got him into dry pampers, found out he doesn’t wear jammie pants to bed, and even though he rolled his eyes at me, I gave him a pat on his padded rump and tucked him in. And I promised him he could text me tomorrow. Boy needs to learn to play a little hard to get.