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Sunday, 14 May 2017

Art - The New Babysitter

"The New Babysitter"

Following a brief hiatus (more on that soon; it's not for negative reasons but due to a combination of real life dullness and a more exciting ongoing project I will talk about soon) we leave the wonderful Mean Maid Month behind and move on to something a bit different...


One of my all-time favorite spanking fantasies. Why? I don't know. Maybe because I never really *had* a babysitter as a kid (not the 'young highschool/college girl/au pair' stereotype, at least)? Maybe because back when I first discovered I was a spanko (rather than just having "funny feelings" about bossy girls as a kid) I was in highschool and thus the peers I had those first truly 'spanky' thoughts about were that perfect 'babysitter age'?

Regardless, it's a theme I love to revisit in any form (art, stories, ageplay videos/audios) so was fun to return to here. I've already done a few art pieces in the past that could be seen as babysitter scenes (such as here and here), but this one is the first I've posted here that was expressly intended to evoke that unique spanking relationship.

The concept behind this image is that this is a boy's first 'sitting session' (i.e. encounter) with a brand new babysitter. Whether this is his first-ever babysitter (forever making him associate the idea of babysitters and spankings!) or just his latest babysitter when the previous ones were much more easy-going, sweet and far less inclined (or even not inclined at all) to administer corporal punishment, THIS sitter is certainly making a very painful impression on him, I think!

I envisioned this sitter as deliberately different from the "normal" babysitter fantasy (vanilla or spanko); usually, such sitters are either pretty 'girl next door' types who earn their charges' crushes (or, more commonly in vanilla cases, their charges' fathers' crushes!) through a mix of innocence and peppy charm, or "hot cheerleader" types who flaunt their sexuality and have boys and men of all ages reaching for the tissue box between visits!

*This* sitter in my pic is neither sort of girl! I imagined her as in her final years of highschool or (more likely) early years of college. She's something of a 'bad girl' or 'rebel', with her tattoos, piercings, dark makeup, short hair and goth/punk fashion sense... certainly not the kind of 'good girl' a mother usually looks for in a babysitter! Nonetheless, she's somehow become this poor boy's new sitter, and is now making clear to him that she is *not* someone who messes around when it comes to discipline!

She's using a paddle on him here, another deliberate choice, as I wanted to make it clear that when *this* babysitter comes over, she brings her own spanking paddle with her! This isn't a girl who has to borrow Mummy's hairbrush or press a ruler (she was using for homework) into service when her charge unexpectedly misbehaves... THIS sitter comes prepared - perhaps even premeditating - to spank and spank soundly! Her severity is clear from her choice of paddle, too; that purple-painted wooden paddle with holes is a tool designed for just one thing: to make a bare bottom *burn*! If she's not already a sitter who's feared for her willingness (eagerness?) to spank, she'd be surely feared as "the babysitter with that awful paddle!".

I wanted to make this instantly appear to be a visibly severe spanking, too... from his expression to the state of his bottom! This is not a girl who "goes easy" on anyone, whether it's their first spanking or their hundredth!

As for the spankee... given his appearance, he's possibly at the age where he thinks he doesn't *need* a sitter, but his mother has insisted. One does wonder *why* he needs a sitter at his age, though, and/or how he ended up with *this* particular no-nonsense girl who's denim-clad lap he's now frantically squirming and writhing across?

Maybe his mother is very overprotective of him, still viewing and treating him like Mummy's Darling Little Boy despite him being a teenager now? How embarrassing! In such a situation, the poor boy's mother probably didn't mean for her Precious Dear to get severely spanked at all, but rather that she just naively selected a random babysitter from the phone book, or on recommendation of a friend, without any idea that this particular sitter had a policy of spanking *every* boy she sits, good or bad! Oops! I do like the horrible unfairness of that scenario, though, I admit! Will his sitter, once the 'mistkae' is realized, be fired... or will she 'persuade' the boy not to tell his mother and return for increasingly painful visits? Perhaps - despite her rather 'rock chick' appearance, the sitter is able to put on a good, sweet face for the mothers of those 'nice boys' she sits?

On the other hand, maybe he's a bit of a troublemaker who's proven that he *does* need supervision when his mother is out? In that case, his mother probably selected this babysitter based *knowing* that she would be a lot stricter than most; possibly her reputation is well-known in this scenario! A teenage boy who needs a babysitter needs someone a lot stricter and harsher than a sweet little boy who can be paired with a peppy, 'fun' teenage girl... a surly, rebellious teen boy needs a babysitter who won't put up with any nonsense and who isn't afraid to lay down the law... or the paddle! In this case, the sitter's 'bad-ass' attitude would likely be known and welcomed by mothers who hire her... she's the girl you hire when your son gives grief to the 'nice' sitters and/or is in need of a painful lesson from someone other than his own mother (which could lead to cases where mothers don't just hire her knowing she'll spank freely while she's out, but where they might hire her with the specific purpose of spanking him when they can't or won't themselves).

Whatever the reason, whatever the scenario,one thing is certain: this boy is always going to remember THIS particular babysitter (and this spanking!) for the rest of his life!

As always, comments are very welcome and encouraged! What do you think of this scenario, how it compares with 'typical' babysitter fantasies, and how/why this spanking might be happening? And what will this pair's future relationship be? Will this be a 'one-time' sitting deal, or the start of an ongoing 'relationship'? What will Mom think? Why was she even hired in the first place? Leave yout thoughts and comments please!

As most of you know, I often go into far more detail than needed when creating characters and situations in my art and stories. Usually, the only place much of this detail is found is in my blog posts. Equally, while I might be able to tell you the relationships I imagined between pairings in certain works, I often prefer to let the viewer decide for themselves, which is why I like posing questions in my posts and getting feedback and comments from others on them...

However, in this case, I wanted to reveal that while all the above is true from a 'musing' point of view regarding this artwork, the spanker depicted here is actually based on a rather detailed character that I created a while back. She also appears in an (as-yet-unpublished) story I did for someone, however only in a very minor capacity. She's a character I really like and often re-use (along with many others!) and have thought about involving in other projects too.

Her name is Avril Novak. After a rather rebellious time at high school, Avril made money as a babysitter while in college where she was known as one of the meanest sitters around, before dropping out of college eventually to form a garage punk/alternative all-girl band (the 'Riot Syrens') who went on to become rather popular, but who developed a fierce rivalry with another all-girl band named... well, that's going into too much detail and will spoil my next art post! TBC!


  1. Hi Banjo

    I love the babysitter topic. In my fantasy the babysitter is in the same age or younger than the boy she babysit.I like the gothic outfit. Perhaps she should wear a t-shirt with a scull on it, or a message like I HATE BOYS. She also should have a sadistic smile, so everybody could see that she enjoy what she is doing.Thank you for your work and greeting from


  2. Interesting profile of this Avril character. I'm interested to see where this battle of the bands idea is going, and how it would relate to F/M shenanigans.

    I can't imagine that the boy's mother saw her show up in that shirt and still let her babysit, though. I guess she arrived a few minutes after the mom left home.

  3. I also wonder; did she really get that paddle just for babysitting, or was it originally for use on boyfriends?

  4. Great image.You have a gift.

  5. Well I love babysitter fantasies and I love goth girls so this really ticks all the boxes for me :D

  6. Glad to have you back! Your work is fantastic fantasy! Would that I was receiving....

  7. This artwork is as beautiful as it is hot, the purple background setting off impressively both the dark tones of Avril's outfit and the rich hue of the young man's paddled bottom. In fact, I'd say that this abstraction of plain colour in the background has greater impact in helping to define the figures than would a particular setting such as a bedroom or lounge.

    Avril's punk-goth look is great. I especially like the boots. I'd have been tempted to complete the look with PVC pants rather than denims, though it's true that this is, after all, an evening spent babysitting rather than a night on the stage with the Riot Syrens, so maybe denims are more fit for purpose (unless she's off to a gig later, using the opportunity to spank her charge now as a way of firing herself up for a riotous performance in the bar or club!) The badges on her bag are a nice touch. I imagine a girl with her sensibility would wear rings and a few other 'alternative' adornments but I'm quibbling: again, it may be for practical considerations that she's going jewellery-lite this evening, bearing in mind all the pulling, grasping and shoving involved in 'girlhandling' a babysat brat for his paddling!

    I wonder whether this bottom-bruising paddling represents an escalation in severity from a previous babysitting session with the boy, of perhaps the week before, when she'd dressed down a little, by her standards (maybe wearing a black Riot Syrens tee shirt, denim pants and sneakers) and settled for handspanking him (albeit with firm, buttock-flattening, ultra-stinging smacks!) This might have been what she'd said to him after that spanking:

    "Okay, brat! So your mother is due home any minute... and you have a choice to make! You could put your pants back on, dry your eyes and pretend I *haven't* just smacked your butt red raw! Like this hasn't happened! Or I guess you could carry *on* bawling, show off your red butt to 'Mummy' and blab about what a bitch babysitter I've been! Hah! Make your mind up, brat... but watch your step! Suppose you *do* snitch! What then? Maybe your 'Mommy' will be all about kicking me out, waving her arms around in horror and never giving me this gig again! Yeah, maybe. *Or*... maybe she'll be cool with this, like all 'Whatever!'... paying me a freakin' *bonus* and asking me back for this time *next* week! And you know what? If *that's* what happens, if I return... I'm *soooo* bringing my paddle! I'd be dressed for it too, cos next week I'd be going straight from here to a downtown dive bar for Mayhem Night with the Riot Syrens! Well, brat? What you gonna do, huh? *You* know your 'Mommy' better than I do. You keeping this a secret? Or are you gonna snitch and risk... THE REVENGE OF THE BABYSITTER!?"

    It seems he made the wrong choice...

  8. Whilst your guesses are close, there is but one true story.

    Her name is Avril. The boy is James, her younger nephew, the son of Mildred. Indeed, even though Avril is family, the young goth was not Mildred's first choice of babysitter. A long line of college-age girls have failed to tame James: petty blonde things, church-going brunettes, and one fiery Irish redhead - all thought they would try their hand at minding the neighbourhood terror for ten dollars an hour.

    You witness Avril's second night babysitting James. The first went the same way as with the other girls. Three hours of wilful disobedience drove even the most hard-up girl from accepting another thirty dollars. No amount of money was worth dealing with that brat.

    After her first attempt at babysitting, Avril said to Mildred, "That boy needs to be taken down a peg, Mrs Sherwood. Given a good dose of discipline."

    At first, Mildred had been shocked - none of the other babysitters had said so much on their hurried scurries from her house, though neither had any accepted a second gig. "Whatever do you mean, dear?"

    "Has the terror been spanked before?"

    "Good heavens, no."

    "Thought as much," Avril said. "Look, I really need the money, and I'm happy to look after him again, but if he acts up like tonight, he'll end up over my lap getting a red butt. Guaranteed."

    Two weeks passed before Avril received the call, after Mildred had tried and failed to get each and every one of the previous babysitters to look after her dear James. Only in desperation did she call the last number on her list. Avril reiterated her plan for dealing with misbehaviour. It was a reluctant mother who agreed, telling herself that her son would surely behave himself this time, though perhaps deep inside she knew what her son needed even if she could not give it herself, for she gave poor James no warning how painful misbehaviour might prove that night.

    Licking her lips in anticipation, Avril slid her spanking paddle into her backpack. One ounce of misbehaviour and she'd give the little cretin the spanking of his life.

    Unfortunately for James, as you can see, Avril knows how to give a naughty boy the spanking of his life.

    How do I know this story?

    Avril just called and told me to stand hands on head in the corner. She's on her way back to our place, apparently all hot and bothered from the brat's squirms and tears. Now, I am going to get that horrible paddle simply because Avril feels like giving a second dose of discipline before she lies back and enjoys my pleasurable ministrations.

  9. Take it to the next step. The father discovers the boy's well spanked bottom. Knowing that his wife did not do this he ask's the boy who spanked him. When he finds out it's the babysitter he contact's her and offers double the money to spank the father of the naughty boy. After all the boy had to learn bad manners from somewhere. Now the father will get the discipline that his wife refuses to do...

  10. Love babysitter fantasies. Based on my own experiences, tough, I'd go more for the schoolgirl look with cabled knee socks or soft tights that provide stimulation below to contrast with the punishment above!