The Best Babysitter in Town Vol. 2 Ch. 11

I'm back from vacation and excited to share this! I'll proof it later. I don't want you to wait any longer for it. Enjoy!

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Something is wrong with me I’ll just toss that out there before moving on. Had I turned around, I imagine I would have Gordy looking at me like I had two heads growing out of two heads. I still don’t know why I offered to help him. I still don’t know why I’m characterizing it as an offer when I pretty much said, ‘okay, I’ll give you an enema. Let’s go knock it out and go about our day.’ I guess I could parse my reasons on and on, but in my defense, having cleaned up his (no good, very bad) messy diaper, giving him an enema was friggin sanitary.

I got to the top of the stairs and asked, “Do we do this in the bathroom or on your changing table?”

“Bathroom,” Gordy replied. “Uh, this way.” You can tell when Gordy gets nervous because he starts saying obvious stuff to fill the awkward silences, though it wouldn’t have been awkward if, well, you know.

“Show me where everything is?”

“Y-yeah,” he said as I followed him into the bathroom. “Under the sink.” He bent down, and I resisted the urge to pat his diapered little butt. It’s awfully cute, and it was even cuter with that cartoon diaper peeking above his pants. He reached past the little box that held the soap he nommed the day before for telling a lie and retrieved two disposable enemas from the very back. Poor guy really should have the guest room with the en suite bathroom. Even if he didn’t have issues like he does, he’s too old to be sharing a bathroom with his much younger siblings.

He stood up, awkwardly holding the two boxes. I spared him the embarrassment (or what embarrassment that I could spare him, which probably wasn’t much), and took the boxes from him. “Both of them?”

“Uh, mhmm.” He had turned red again. If you blush too much, can there be, like, a negative consequence? Probably not or he’d have had it by then.

“Hey, Gordy,” I said in my reassuring-babysitter voice, “not a big deal. Or you can still do it yourself if you like. You always have that choice. I just thought this would be easier.” I’m not sure if, once I’ve said something, Gordy will ever tell me know or reverse course. He seems so smitten and shy it’s hard to imagine him telling me (or any pretty woman?) no. Can’t say it would’ve hurt my feelings if he had. I just figure this really was easier, I guess, and well, screw thinking about motives. It’s boring, right?

“I know,” he said. He started to get on the floor.

“Woah, buster! We can make this a little easier and cleaner than that. Here put this down.” I handed him a dry towel, and he laid it on the floor while I opened the boxes. “Are these pre-lubricated?” He nodded. “Want some more?”

O, did that create an entirely new shade of red. I call it Gordy. It’s like if something crimson turned crimson. He just sorta stared at his feet and nodded.

“Okay. Wanna go grab that?” I sat down in the edge of the tub and waited less than a minute for him to come back with a tube of A&D ointment, the kind that’s basically just petroleum jelly, and a pair of gloves for me. See how considerate he is? “Alright,” I said, “ya ready?”

“Uh, y-yeah. Mhmm.”

“Why don’t you take your shirt off,” I suggested, “while I get these down.” I pulled his sweats down and left his socks on. He was shaking a little. “Hey,” I said softly, “calm down. It’s okay. Really. You read to lie down?”

He looked about as relaxed as plywood lying on the towel. I got on my knees and asked him to spread his legs a little for me. “I’ve done this once before,” I narrated as I untaped his diaper. I stuck the tapes back on themselves to save the diaper. “Quick and easy, right? I’m gonna open your diaper now.” It was just slightly damp, and as per usual, I held it over him for a moment to make sure I wouldn’t get sprayed. “And I’m gonna leave that under you just in case. Is that how you usually do it?” Guess I should’ve asked him how he usually does it before getting started. On the other hand, how many ways can you give an enema? He nodded.

“Gordy,” I said in my I’m-nice-but I-mean-business babysitter tone, “it’s okay if you don’t want to use your words through parts of this, but I need you to tell me if something if something hurts or you think you’re gonna have an accident, okay?” He nodded, and I gave him the look.

“Okay. Sorry.”

“No need to be sorry. Just need to make sure you’re okay with what we’re doing and nothing hurts. Wanna grab your knees for me?” I’m gonna go out on a limb and say I doubt he wanted to in the purest sense of the term. “Let me know if your arms get tired and I’ll help. But I think we’ll get this done quickly,” I said as I put on the gloves, unscrewed the bottles, and added some of the lubricant to the tips. By the time I was done, there was Gordy legs up and bottom exposed. I could almost not tell I’d spanked that bottom just the day before, and spanked it pretty hard too. Gordy’s butt heals fast, I guess. And in all seriousness, giving an enema is not a big deal, not after changing a twenty-year-old out of a messy diaper. 

No, the serious and awkward and seriously awkward part comes when your finger brushes the tip of the enema nozzle and you notice it feels awfully firm, and because you’ve been absentmindedly narrating things anyway say out loud, “This would be a lot more comfortable if I put some on your button.”

I think we both blanched at the same time. “Um,” I said, embarrassed because it was my turn to be and I’d earned it. Honestly though, I don’t know why. I’d literally put rash cream on his button while changing his diaper. I guess the difference is I wasn’t following that up by putting anything in his bottom right after I did.

“Uh,” I tried again, “is it okay if I do that? Will it, uh, help?” He nodded. “You’ll tell me if you feel uncomfortable?” He nodded again. “Okay, just a sec.”

First time giving a twenty-year-old an enema … first time lubricating my own finger with petroleum jelly.

“Okay … One, two, and three.” And I was applying it to the outside, where it didn’t really need to be. I felt his button pushing back against my finger, not very hard, and then with no fanfare and only the slightest pressure, I was inside. The ring of muscle around my finger was tight, tighter than I expected, but I don’t know what I expected from the sphincter of a twenty-year-old who wears diapers both kinds of accidents. Probably best if I made an effort to have no expectations when it comes to Gordy; he surprises me every time.

I slipped my finger in a little deeper and turned it left and right. I couldn’t help notice that it felt like, well, the soft insider of a person. It was an interesting sensation, obviously for him but for me too.

I had this off thought to feel around for a sec to see if I could find his prostate. It was more biology experiment, but since the first time I slapped Gordy’s bottom and discovered my own little dominant streak, I’d done some exploring online and definitely liked the videos I’d seen of prostrate milking.  It’s just inexplicably hot watching cute boys writhe helplessly on the end of a woman’s finger. Just … looks like fun for all involved.

But it wasn’t playtime (among other things, I didn’t have Gordy’s consent). Still, it left me curious just where his prostate was.

“Okay, I’m gonna take my finger out now. Everything feel okay?”

“Yeah.”

“Ready for the real thing?” Wow, what an odd way I phrased that. Haha. Everything is perfectly normal. Ha.

“Um, y-yeah.”

“Wanna take a break first? Put your knees down?”

I took it as a yes that he dropped his knees and took a deep breath. I’d seen it so much, I hadn’t even noticed Gordy’s peepee when I took his diaper off. It was, ahem, hard not to notice it then. Well, hard not to notice but easy to overlook, if you get my quadruple entendre. It’s just cute, is the only way to describe it. Among the other new and interesting I discovered about myself while discovering new and interesting videos on websites ending in -tube and -hub and -bang was an appreciation for small ones. With his build, he could totally be a femboy too. He doesn’t even need makeup; just say his name and his cheeks go so red.

We both studiously ignored it. Well, I did. Gordy was keeping his eyes glued to the ceiling tiles, but I’m assuming he knew his little pump was primed.

“You ready,” I asked again.

“Y-yes.”

“Okay,” I said skeptically without meaning to. I wasn’t actually skeptical. It was more of a if-you-say-so-cutie tone that I tried to stop thinking about to focus on the task at hand: helping the diaper-wearing twenty-year-old I babysit and occasionally spank make a poopie in the potty. My life is different than other college women my age.

He lifted his knees, and I offered, “I’ll help this time,” and put my hands against his heels. “Actually,” I said as soon as I did, “just a sec.” I needed two hands. One for the bottle and the other to, you know.

“Ready?” He nodded. “One, two, three.” I slipped the tip of the bottle all the way in. “Is they okay? Comfortable?” He nodded rapidly, and I put my hand back against his heels. “Okay, I’m gonna start squeezing, alright?” I gently squeezed the bottle, and nothing.

He didn’t see me frown at him. His eyes were closed, and he was holding his breath. 

“You gotta relax, sweetie. Deep breath.” He did, and the bottle became easier to squeeze. I worked it a little this way and that to make it flow better, and kept a steady pressure on the bottle.

“So,” I asked him, “do you use two bottles right in a row, or, um, do you take a break in between?”

“In, in a row.”

“Okay. Almost done with this one. How do you feel?”

“F-fine.”

“Not too full?” He shook his head. I have the almost empty bottle a harder squeeze to get the last drops in him.

I’m a big believer in projecting confidence as a babysitter even when I don’t feel it. It keeps the kiddos I sit for calm. But sometimes admitting you don’t know something can instill confidence. This wasn’t one of those times, but this was a very necessary question: “So no good way to ask this, but when I take this bottle out, so I need to be worried that’s not, um, all that’s gonna come out?” He sighed and I think shook his head. It was a very small shake, and I figured this was one of those things it’s important to confirm, so I asked, “Was that a no? I can get your diaper ready to pulled over you just in case if you just spread your legs a …”

“No. It’s okay.” He was embarrassed, for sure. Humiliated even. And he just sounded sad and frustrated (and not just because he was constipate - who isn’t sad and frustrated when they’re constipated, right?). It kicked on one of those automatic babysitter things I say without even thinking. 

“You’re being really good right now. Really good and really brave. We’re almost done. I’m taking this out.”

I did, and Gordy let go of his knees for some reason, putting them across his eyes instead. It caught me off guard, and I almost dropped his ankles. I didn’t know why he did that, and he seemed to be done using words for the next couple minutes. Maybe what I’d said upset him. Maybe what we were doing upset him. Kinda either way, even though I sympathize with his feelings, it wasn’t a very mature thing to do, by which I mean it wasn’t a very mature way to handle whatever feeling he was having. But I’m nothing if not empathic.

“Almost done. One, two, three.” I started squeezing. If he’d left me a free hand, I’d have given him a sympathy rub on his thigh.

The second bottle went quicker. “I’m taking it out now. You’re doing good. Ready to get up?”

From behind his arms, he said, “It helps to wait … on my back.”

“Can you take your knees again?” He did, and I put the bottles and boxes in the trash, then my gloves. He seemed to rock himself back a little. I was confused, but the power of logic only took a half a second to clarify. why he did that. I was sitting next to him, and once more operating by babysitter instinct, I put my hand on his tummy to give it a little rub.

His tummy was wet. Which led me to take note of his soft penis. Which led me to say in my head o shit o fuck o gawd! Is that why he dropped his knees? The poor little lamb. Of course he’s humiliated. How awful for him.

As casually as I could, I rubbed my thumb and forefinger together. First time in my life I ever felt an impulse to jump to my feet and declare, Hooray! It’s not pre-cum! He’d just piddled a little.

He put his legs down, and I pulled his diaper over him. I didn’t tape it. “Do me a favor and hold that when you get up?” Because reasons. Very obvious reasons.

He didn’t respond, but he did start to get up. My cue to leave.

“I’ll wait in your room. Call me if you need help.” Okay, what the fuck kind of help could he possibly need from you right now, the part of my brain that too frequently makes itself heard after the babysitter part has already put my foot in my mouth for me asked. He didn’t see me blush. I closed the door and went to my bathroom to wash my hands.

While I was waiting in his room, I restocked his changing table (and straightened his desk and nightstand because I’m a crazy person; I half tempted to empty his dresser, retold everything neatly, and put it back, but I’m not that sick). I waited … and I waited … and I laid everything out to get him in a fresh diaper … and I waited … and I went down the hall and put my ear to the door … and I was about to gently knock and ask if everything was alright when I heard very clearly (very clearly) that everything was exactly as planned and retreated to his room … and found a booster pad and laid it on the open diaper.

I waited and waited some more and resisted the impulse to go knock on the door. What could I provide except a pep talk, though he’d needed one of those earlier. It’s not like he’s a toddler who needs his bumbum wiped … at least, not when he’s upright. I waited and scrolled on my phone and oops! I googled how to find the prostate, but I closed the window as soon as I heard a flush. I put my phone away when I hard the bathroom door open, and then in walked a sheepish Gordy. Because it would be mean to say to him, I’ll say it here: he probably wouldn’t feel so sheepish if he didn’t walk around naked between his socks and shirt. I’d gotten used to it, but I couldn’t shake the way it just seemed toddlerish, like he wasn’t aware of this thing called modesty. Yeah, I saw it (and touched) during diaper changes, spankings, baths, and now enemas, but context kinda matters. Had it bothered me, I’d have asked him to cover up. Even though it didn’t bother me, it seemed like one of those points of etiquette I should impute as his babysitter (and friend and woman), but Gordy is so sensitive, I knew he’d take it as a scolding and catastrophize. He’d probably think he had harassed me and go damn near catatonic with guilt. He hadn’t, of course; he’s just a twenty-year-old who’s had his diaper changed so often and by so many caregivers that he doesn’t see his own nudity as, well, that kind of nudity, i.e., adult. At least, that’s my guess.

“Feeling better,” I asked him. He was looking at the floor again as he handed me the cream I’d used to lubricate his button. I guess give him credit for putting his shirt back on.

“Yeah … Thanks for your help.”

“What are friends for?” Not that. Friends are not for that. Shut up sometimes, why don’tcha? “Sure you’re all done?” He was in there on his own almost a half an hour; for the poor little dear’s sake, I hope he was finished.

“I think so, but …” He left the rest unsaid. He hopped up on the changing table.

“I got it,” I said as he started to position the diaper on himself. “Just lift up.” I got it situated right. 

I lifted his ankles, and in response he told, “I just did that.”

“Humor me,” I said in good humor. I got a wipe from the warmer and ran it through his crevice. He tried to hide it, but he winced. I don’t, ya know, stare back at it while I’m doing the job, and the wipe would’ve kept it hidden anyway, but turns out someone else wincing is something you can hear, see, and feel if you all there is between your hand and their button is a baby wipe. Just a little wince and just a little clench. I looked at the wipe - either he didn’t clean himself as well as he thought (or was happy with how clean he was; boys and their hygiene, right? Of course I’m right), or he was a little leaky back there. It wasn’t a lot, but it was enough. In fact, from my metaphorical and literal point of view, anything but a pristine, white wipe is enough and too much.

I knew he doesn’t always do a good job wiping, which leads to diaper rash, which leads to him being grounded from changing his own diapers. Part of me wanted to show him the wipe, tell him it was yucky, and that he needs to try harder. In fact, had he been about a quarter of his age, I would’ve told him exactly that and asked him if I needed to tell his mommy and daddy that they needed to work on that with him (or maybe not really said that, but I have ‘suggested’ to a couple parents that in fact, no, not all kids that age have undies like that and they need to brush up on that skill; hopefully it’s not a failing the parents passed on - yikes!). But like he hadn’t been through enough for one day (and weekend that wasn’t even twenty-four hours old, and lifetime). I was more concerned about the wince, and I could see the reason.

“Little tender down there?” It was a rhetorical question. I put a glove on, took a dollop of rash cream, and spread it gently. “That will probably help sooth that.” I then finished the job (this time with one of his regular nighttime diapers), and he sat up,, swinging his legs over the side and just sitting there for a moment.

“Wanna tell me why you suddenly got upset during that,” I asked directly because I may be the best babysitter in town but I still get tired of dancing around stuff, and we were dancing around so many things.

“I didn’t get upset.”

“Sure seemed like it to me.” I got no response, so I pointed out, “You were talkative downstairs, and then you clammed up again.”

“I don’t need you to manage my feelings. I’m not a little kid.”

Whoa. I’m pretty positive I didn’t deserve that, and I didn’t see it coming either. He may be twenty, but sometimes he reminds me of my child development textbooks for teens - prone to mood swings, can go from being an adult to a child very quickly. He’d peed on me and joked about it a couple hours ago, helped me with my homework, and then snapped at me. 

“If you were one of the little kids I sit for, I’d tell you that’s not a very nice tone, and then I’d sit you down in my lap and we’d talk until you told me what was wrong, and then we’d fix it together. You don’t have to tell me, but I’ll say it again anyway: I’m not judging you; I like helping you; I’m still your friend; and you can tell me anything.”

“Not when it’s …” He cut himself off and sighed before hopping down off his changing table.

“Yes you can.” I waited a beat and got nothing. “Could you please go put your pants back on and throw away the diaper in the bathroom? I’ll be in my room for a bit if you need anything.”

Bonus about babysitting twenty-year-olds: you can take a break from being a babysitter and be reasonably assured no one will get hurt, nothing will get broken, and they won’t follow you like a puppy. I had a pretty good idea what Gordy wanted to say, and I was kind of glad he didn’t. I needed time to think about it.