The Best Babysitter in Town Vol. 2 Ch. 2 (Patreon)

‘Yeah, fine’ my ass. When I knocked on the Rooney’s door, I was expecting Gordy to greet me rather than his harried stepmonster who was apparently running late.

“Come in,” Mrs. Rooney said not out of breath but putting in some aerobic work effort as she tried to get out the door for her long weekend.

“Hi.”

“Thank you for watching him this weekend. I really appreciate it. He really doesn’t like going to the lake and my sister couldn’t take him this weekend and I just don’t feel right leaving that boy alone for a long weekend.”

She was walking awfully fast as she talked awfully fast. I’m not sure she fully heard me when I said, “Well, he is twenty. He can stay home alone like all the other adults.”

“I know, I know, but he doesn’t like to. He doesn’t like being on his own all weekend, and he doesn’t have a friend’s house he could go to either. But either way, I’m glad you’re here for the weekend.”

I would’ve stayed over as a friend or had him stay at my place, but if there was any confusion about whether I was a friend hanging out or there as a babysitter, let there not be. I’d specifically been asked to babysit, agreed to babysit, and was being pai a small fortune. I was charging them the going hourly rate for a caregiver, a price I got from calling a few in-home health agencies. They definitely could’ve found a babysitter for less, but aside from Gordy wanting it to be me, his stepmonster and cypher of a dad surely wanted it to be me as well, someone who knew what was up in their house and wouldn’t call the police, which I very nearly did last time until Gordy explained the whole thing was consensual. What I was earning that weekend would cover almost four and a half credit hours. Cha-ching. Seriously.

“Where is Gordy?”

“He’s up in his room,” Mrs. Rooney replied with a verbal eye roll. “He’s in trouble again.”

“What happened?”

“I’m sorry, but I’m in such a hurry to get on the road before rush hour or it’ll take an extra hour. Mr. Rooney and the kids left this morning, and I had a plan for the day and things at work just … Anyway, Gordy will explain it to you. I left a note on the table along with an envelope. I was going to walk you through it, but …”

“It’s fine. I’m sure the two of us will manage. We’re adults.” Hint hint.

“Thank you. The note has everything you need to know, but of course call if you have questions. I can talk in the car on the way up.”

“Will do if I need to, but I‘ll ask Gordy first.”

“Thank you. Do you have any questions before I go?”

“Nope. Have a safe drive.”

“Thanks again. I know him being in trouble isn’t the best start to the weekend, but try to help him have some fun. I know you think I’m too strict with him, but he deserves some fun too. He really needs to let a little loose, and he likes you. I think he has a crush on you.”

“You think so,” I asked like the best babysitter/actress in town. He doesn’t moon over me on campus, and maybe his feelings have gotten less intense since the first time I babysat, but after his bath that night, he was making puppy dog eyes at me. Especially when he tried to make a move while we were sitting on the couch. I shut it down gently, and he brushed it off, but I know the boy was hoping that HJ meant more. I didn’t know if he was still hoping that.

And I didn’t know what I wanted. I had definitely enjoyed the ways I got to dominate him that night, even if I hated giving him an actual spanking and making him cry, and I’d learned a whole lot on the Google machine since then. Things I wanted to try, but I didn’t know if I wanted to try them with Gordy, or if he’d want to. I was very aware he was lonely, frustrated, and inexperienced (a/k/a a virgin who’d never even been out on a date before), and I absolutely, positively did not want to inadvertently take advantage of him.

“O, for sure he has a crush,” Mrs. Rooney said with her hand on the doorknob. “I’ll see you Tuesday. Call if you need anything. Note’s on the table.”

“I will. Have a good trip.”

I don’t think she’s strict, by the way. I think she’s a psycho bitch, and I think either there’s a lot more to Gordy’s story than he’s told me, or else she’s on a power trip or getting her jollies off on the way she treats him. I thought maybe Gordy was getting some jollies of his own, but he insisted he doesn’t and I believe him. You would too if you’d heard the hangdog tone and seen the lost little lamb expression when he denied it. Any doubt I had disappeared when he started softly crying before I even had him over my knee, plus there was no other compelling evidence he was enjoying himself. Evidence, a little; but compelling? No, if you get my meaning.

I set my bag by the stairs and walked into the kitchen to read the note. Not before, of course, counting what was in the envelope. Did I say cha-ching already? I don’t think I’d ever held that much cash. I mean, I have no idea how much money the Rooneys have, but judging by the house alone, plenty, on top of not even blinking when I named my price.

I set aside some for Gordy, something he and I worked out in advance. Last time, I gave him half to prove I wasn’t just in it for the money, which made him feel a lot better about things, knowing I meant it when I said I cared for him. I care for all my charges, and even more with Gordy. I grew up with him. We were all protective of him back then, and I always did like him even if until now we never did anything together outside school. We weren’t friends then, just friendly. And on that first night, it made him feel much more confident to know I was still his friend and not only his babysitter.

I didn’t give him an entire half this time, and I didn’t do it to prove anything or buy his cooperation. I did it because I liked the idea of putting one over on his jerk parents. Plus he could probably use the money. I didn’t think he had a job, and I didn’t know why not he didn’t. Wouldn’t at all surprise me if his stepmom didn’t let him. But mostly, I liked the idea of his stepmom being such a bitch that she hired a babysitter for him, and that babysitter took some of that money and put it directly into Gordy’s pocket.

I listened up the stairs and debated going up to check on him first, but I decided to read the note before I did.

Sally,

Thank you again for spending the weekend with Gordy. I really appreciate it. He doesn’t like the lake, and I’d rather he stayed home than spend the weekend moping. Like I told you, he doesn’t like being alone for so long, and my sister is out of town. I’m more at ease knowing he’s with someone too.

Gordy should be able to answer any of your questions, but he’s bashful about certain things and it’s probably easier for me to just tell you.

You know Gordy is incontinent and wears diapers to manage it. Thank you so much for being willing last time to change him. I hired you specifically because I knew you’d be mature about everything. He’s allowed to change himself this weekend, but it doesn’t hurt to check that he’s doing a good job. He’s been doing a good job lately, but if you see any sign of diaper rash, he loses his privacy privileges until it goes away, so you would need to change him.

You didn’t have to change any stinky diapers last time, and you shouldn’t need to this time. We use timed voiding to avoid dirty diapers as much as possible, which means Gordy will sit on the toilet every morning until he has a bowel movement. He’s pretty regular. That said, it’s not foolproof, and messy diapers do happen. He can change those too, but it’s not the easiest thing for a person to do themselves sometimes and I always check to make sure he’s clean (to my satisfaction, not his – you know how boys can be about hygiene 😉). But hopefully that won’t happen.

You know about Gordy’s behavior issues and how they get dealt with, and thank you again for being discreet about it. I know I was a little deceptive last time when I didn’t tell you I needed you to watch Gordy, but no false pretenses this time. You’re the babysitter, and you have authority to correct any misbehavior however you see fit. I don’t know what your feelings about spankings are, and there are plenty of consequences you can try before it comes to putting him over your knee. All I can say is he does respond to a red bottom, but if you’re not comfortable doing it, of course you don’t have to. But I do ask that if anything does happen that doesn’t seem like it can be addressed some other way, please tell me when I get home, and I’ll see to it. Gordy knows that, so he should be well behaved all weekend.

Just a few other things:

⁃ There’s money on the counter for ordering in or going out.

⁃ Gordy doesn’t have a bedtime when he’s not in trouble, of course, but don’t be shy about “suggesting” he calls it a night. He stays up too late if you don’t remind him sometimes.

⁃ Have fun this weekend. Take him out for an evening. He needs to let loose a little – not much, but a little. And between you and me, I worry about launching him into the world, so however much he might protest, getting him out and socializing even for a few hours will be good for him.

⁃ We’ll be back Tuesday around lunch time.

Thanks again and have a good weekend!

I could pick apart so many things she wrote, and a whole team of psychologists could no doubt have a field day, but I’d already decided there was no point to it so long as Gordy was okay with it. I really didn’t want him to be okay with it, but that wasn’t my business. At least, not as his babysitter. As a friend, sure. On campus, I could only be his friend, but in his house, with him under my care (which is such a weird thing to even say), I could be both, but only to an extent.

As complex as that is, how much more awesomely awkward did it get when I saw her post-script.

PS,

Gordy got himself into some trouble today. I’m running behind, but Gordy will tell you about it. He’s upstairs in his room. I hate to ask you to do this again, but he broke one of the rules that means an automatic spanking. It’s best to give him a consequence right away, and I would’ve if I wasn’t already running late. If you absolutely don’t want to, that’s okay. I’ll take care of it when I get home. So sorry to start to start the weekend like this.

For fuck’s sake, not how I wanted to kick off the weekend. Or deal with at any time between Friday and Tuesday. Friend, babysitter, or both? And what had he even done? We’d been together less than two hours ago. What could he have done to earn an “automatic spanking” in less than two hours?