The Best Babysitter in Town Vol. 2 Ch. 1 (Patreon)

I knew something was off when we were at the student union. We were part studying, part talking about the weekend when Gordy suddenly made this face like something was not alright in his world. In his twenty years on this planet, the boy has apparently never learned to not telegraph his feelings through his facial expressions, and you don’t need to be the best babysitter in town to recognize the sequence of surprise, chagrin, and embarrassment in his face. That, and the way he stopped talking mid-sentence.

“Everything okay,” I asked him. He and I had been hanging out on campus more often ever since the night I babysat him, or whatever you call watching a twenty-year-old whose dad and stepmom had gone for the evening. He’s allowed to stay home alone, of course, but not when he’s in trouble, and hoo boy did he get in trouble that day.

Long story short: he and his stepmom have this totally weird relationship or deal or something where she disciplines him just like she did when he was a kid, and she misled me into sitting for him that evening. I’d worked for the Rooneys for a couple years, and I thought I was going over last minute to babysit his younger siblings. But nope, she called me to babysit Gordon, my classmate, and didn’t tell me until I got there. No sooner had I processed that when I was told he’d earned himself a spanking and I would need to give it to him. Yes, really. She’s fucking nuts.

I only did it because Gordy said it was okay to, even if he didn’t want a spanking. And don’t think I didn’t exact a premium price from his stepmom for the weirdness of the evening, which included changing the poor boy’s diapers. He’s always been incontinent, which I knew about going all the way back to when we were in kindergarten together, and not being allowed to change himself is just another of his stepmom’s rules: if he gets a diaper rash, he’s not allowed to change himself until it’s gone plus a week or something. And yes, he was getting over a diaper rash.

And yet despite all that incredible awkwardness, and holy crap was it awkward and holy shit was he embarrassed from the moment I walked in the door almost until the moment I put him to bed, we’d had a good time. I discovered I have a little dominant streak as I was swatting his bottom into the corner, and whether he knew it or not, he is a full on submissive. That little thrill I got was enough to get me in the mood to give him a first, a soapy HJ while I had him in the bathtub, with his enthusiastic if tongue-tied consent, I should add. So I was happy to sit for him again when his stepmonster asked me if I’d stay with him for a long weekend, so long as he was okay with it (which he was, and maybe even eager).

We enjoyed our time on campus together in the few weeks since I sat for him. We didn’t meet every day, but two or three a week when our schedules overlapped, and all those awkward subjects never came up, as if by mutual agreement we just didn’t talk about those things when I wasn’t being a babysitter and he wasn’t being the babysat. Just like friends, and why not since we’d known each other since we were five.

I actually give the boy major credit: if I gave an HJ to any other man on campus, I’d expect him to think he’s going to get another and maybe more and think we had that kind of relationship just because of the one time. Not that I do that very often, but, ya know, sometimes. I kinda like giving HJs, and after that evening with Gordy, I understand why: because I’m in charge. It’s literally in my hands lol.

But Gordy never brought it up on campus. He didn’t try to kiss me. Poor boy seemed so stunned when I greeted with a hug one time. I chalk it up to his inexperience and his submissive personality. It’s sweet. He’s sweet. He’s not the type of guy I go for, and yet something is there, some kind of affection that I can quite label.

Being sweet and submissive, however, doesn’t mean he’s always honest, not that he needs to be when we’re just being friends. He has a right to some privacy. That’s why I only pushed a little when I saw that look on his face and asked if everything was okay, and he so transparently fibbed when he replied, “Yeah, fine.”

I looked at him for a moment, leaned across the table and asked him, “Do you need a diaper change?” Not in my capacity as his babysitter, just his friend.

“What? No. I know when I need … I’m fine. But, uh, I should get home. Ya know, say goodbye to everyone before they leave. What time are you coming over?” He was practically throwing his things into his bag.

“3:30. I need to leave soon too. Just gotta swing by my house and grab a few things.”

“Okay. Um, see you soon.”

“You too.” And I watched him walk away, scrutinizing his butt and, this is the babysitter in me, giving the air a little sniff. I couldn’t see (or smell) anything amiss.

Whatever sent him scurrying didn’t have to be about his condition. Maybe he forgot to do something and needed to get it done right away, which wouldn’t have surprised me given the leash his stepmonster keeps him on. But he’d probably have told me that. We joke about her all the time (and sometimes not jokes, because she is a serious bitch; he defends her sometimes, but in my humble opinion as the best babysitter in town who has gotten to see a lot of family dynamics, she’s a bitch with a capital B which stands for Bitch).

But I suspected whatever had him speed walking out of the food court was related to his condition, and I didn’t begrudge him his privacy. We’re just friends on campus and anywhere else. I think I do a very good job separating babysitter me from friend me, and I wasn’t his babysitter for another hour and a half.

Funny, I have a client who has me watch her sixteen-year-old sometimes, and she insists on referring to me as a family friend who just hangs out with the girl, so obviously a put on to spare the girl’s feelings. She must be embarrassed that her parents still leave her with a babysitter, and I wouldn’t be surprised if there were fights about it. She was pretty frosty to me the first few times, but I got her past that resentment, just another way I’m the best babysitter in town. But we all keep up the pretense that I’m not her babysitter, just a friend. She’s mostly easy to get along with and is old enough to talk to like a friend, and I’m getting paid, so what do I mind if we all pretend I’m not babysitting when I’m with her?

But there was never any pretense with Gordy or his stepmom (or, I’m assuming, his ever-silent dad, but who knows what he makes out of the whole dynamic between his adult son and his wife). Nobody ever pretended I wasn’t babysitting a twenty-year-old who’s actually a few months older than me.