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...

Babysitters!

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.

Art - Getting Girly-Brushed

"Getting Girly-Brushed"

In the spirit of my inaugural 'Spanker or Spankable? (SoS)' post, comes this new art piece...

Here we have the type of girl who I suspect others might normally think of as a spankee. She's young, possibly late teens to early twenties. She's also a very 'girly' girl, seen here in a very "girly" bedroom where she is currently giving a young man what he perhaps had often derisively called a "girly spanking".

"Only girls get spanked" is what he might have said. Or "being spanked by a girl doesn't hurt" is an even more likely boast.

So, now she's re-educating him with a "Girly-Brushing": her own trademark bare-butt walloping with her chunky pink hairbrush! Think he's changing his mind about being spanked by girls? I think so.

Spanker or Spankable? #1

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Flashback - One Mean Teen

"One Mean Teen"

This piece is an oldie. You might even recognize the spanker, as variations of her appeared a few times in my earlier works. In this piece, though, she's a bit younger than usual; I envisioned her in her late teens, but her youth doesn't make her any less of a formidable spanker, as you can see!

Since my early youthful spanking fantasies, I have always been a bit besotted with the idea of 'teen spankers', such as babysitters (one of my favourite fantasies growing up), sisters, friends' sisters, cousins, classmates or even girlfriends. The idea of a boy being spanked by a girl close to his own age yet who is still totally 'dominant' over him is as much of a 'hot button' for me as the more traditional 'Auntie' spanking fantasy, for some reason.

I wonder if it had to do with my own teenage sexual urges? I was often confused when I was younger that I found myself inexplicably attracted to the more 'mean girl' types at school; that 'bitch' everyone else hated was the one I found often gave me 'funny feelings' I couldn't explain! Also, as I got older, I realized that while my friends were usually dreaming about winning the heart of (and making out with) that pretty girl sitting across the classroom, I was instead mostly daydreaming about what it would be like to be spanked to tears by her!

But enough embarrassing self-analysis for now; let's move on to the art piece...

Flashback - I'm Not Your Girlfriend

"I'm Not Your Girlfriend!"

This oldie is reposted here by popular demand; I've had several long-time fans tell me in comments or privately that this was one of their favourites, so I felt it only fair to republish it here.

The idea behind it was that he's got a spanking from his attractive young babysitter, and she's pointing out to him that despite his signs of 'excitement' that she's not interested in him in that way at all! To her, he's just a "little boy" (regardless of their relatively close age, in my mind) and she's "not your girlfriend!" but his babysitter, who can spank his bare backside like she was his mommy or teacher whenever she wants!

This old artwork actually went under several names until I settled on this one. Originally I was going to call it something like "Just a Little Boy", which on reflection suits the piece more (and I think I like it more, too), but I felt that some might mistake the title for meaning he WAS a little boy, rather than that just being how she saw him here. I also entertained the title "Not So Big Now", as a clear sign of her feelings about him AND how he's feeling now, physically and emotionally, after her sound hairbrush spanking.

In the end, though "I'm Not Your Girlfriend!" hopefully says what I wanted it to say: she's not only given him a very sound, very humbling, bare bottom hairbrush spanking over her knee, but she's just shattered any illusions he may have had that this attractive older girl might have been 'interested' in him; that his crush on her since she started babysitting him might be returned someday.

No, she's quite clear: she's "grown up and mature", and he's just some little brat who needs a babysitter!

Perhaps she's been sitting him for a long time, and this is the 'showdown' that's been building for a long time with her increasingly annoyed by his obvious fantasizing about her and fawning over her like a lost puppy?

Or maybe she had no idea, and caught him staring at her legs or boobs with a bulge in his pants, and decided to nip the problem in the bud here and now?

Maybe she's reacting to second-hand information? His parents or her girlfriends might have somehow found out/overheard that he had a crush on her, and the next time she babysat him, she confronted him on it... with her hairbrush providing her closing argument?

Or just maybe she came upstairs when he was supposed to be doing his homework or sleeping, only to find him in a very compromising position, 'enjoying himself' with a yearbook or family picnic photo of her (stolen from somewhere, probably!) in his free hand? I think that would definitely warrant a hard on-the-spot spanking and a need for a lecture on the reality of their relationship!

I kinda imagine him as a rather shy, awkward boy, who usually falls apart around pretty girls. As for her, maybe she's not as "mature" as she thinks (a 'cheerleader' type who boys and parties when she's with her friends), or maybe she really is (a top-of-her-class potential honors student, respected by all for her academic excellence and wisdom), but either way he's waaaay out of his league with her!

I also feel this is his first spanking from her, maybe his first spanking ever? Is it telling that he's only wearing his (pulled down) underpants here? From the looks of it, do you think she has "spanked him soft" or is lifting up his stubborn erection with the back of her brush?

What do you readers think about this situation, and how it might have played out? And how will things move on from here?

How does he feel now that his beloved babysitter crush has blistered his bottom and belittled him? When she leaves him alone tonight, will he collapse on his bed for a heartbroken cry... or a furious bout of masturbation?

How about her? Will she continue to sit for him after this? Will she tell anyone what happened (laughing with all her friends about the "overgrown brat she had to spank" or just informing his mother what happened?) or keep it their private little secret? And if she does sit him again... will she spank him again, too? Does she enjoy spanking him or see it as discipline only?

Maybe she will come to enjoy it, and maybe - just maybe - through that enjoyment she'll come to see him as more than just a naughty brat and as a potential naughty 'boyfriend'; one that can't answer her back or disobey her without fear of a sore red bottom; one that - unlike the other boys she knows - has to do anything she says... or else!

It's certainly possible that his submissiveness to her (born from both her babysitting authority and his desire to please his 'crush') might well give her a rather stimulating sense of power over him... maybe she spoke too soon with that "not your girlfriend" comment after all?

Flashback: Unexpected Side-Effect

"Unexpected Side-Effect"

Another art post, another hairbrushed young man! This Flashback is by request from an anonymous poster... who remembers this piece from my old group, no doubt.

I like how this spanker turned out; she's young, somewhat "geeky" but cute. I seem to remember that I thought of her as his same-age girlfriend when I made this back in 2003 or so, which still works for me... but she could easily be his step-sister or babysitter (whom he might have a secret 'crush' on!) too. She actually looks a bit younger than him, but (like most girls!) is probably rather more mature for her age than he is!

He's of course in tears (how any spanking should leave a spankee, IMO!) and blushing furiously... though despite his embarrassment, his main concern is clearly still the burning heat that her hairbrush has ignited in his poor backside; throbbing hot cheeks that he continues to frantically rub with both hands... though to no avail, it seems!

As many know, I like playing with the often wildly differing emotions a spanker and spankee feel during the same 'event'. Though both are obviously focused on the poor spankee's unexpected and humiliating uncontrolled erection and cum-spurting, both are very likely thinking very different thoughts about the situation.

Here, our bespectacled, pigtailed young spanker doesn't seem to know whether to gasp in shock or laugh in amusement... she sure didn't expect to see that when she let him up off her lap! He made such an awful fuss about his spanking, too - all that crying and kicking and pleading - and she was sure she was walloping him hard, too! But now look at him, all stiff and naughty, and dripping messily... and all over the leg of her nice new jeans, too! If it wasn't so hilarious, she might be cross with him for that. Gosh, dd he actually like being spanked?! Or are boys really just that silly and lacking in self-control that their little penises get stiff whenever they are that close to a cute girl?

For his part, our hapless young man is in tears and likely very embarrassed about his "reaction". He's confused too: he didn't enjoy his spanking (it certainly wasn't a "playful" or "sexy" one!)... she spanked him hard, and that hairbrush really hurt! So why was he all stiff and drippy "down there"? Was it was all the friction from his wild squirming and wriggling against her denim-clad thighs, as her hard hairbrush was firmly and repeatedly applied to his bouncing bare bottom? Was it being so close to such an admittedly cute and attractive girl - no matter their relationship - that "set him off"? Or did he indeed - even if only on a subconscious level - find some degree of pleasure in his strict and stinging punishment?

For my part, all I can say is (from both memory and personal experience!) that us 'boys' (of all ages) are definitely prone funny physical reactions we just can't consciously control or explain!

Art: His Very First Hairbrushing

"His Very First Hairbrushing"

Ahh, the hairbrush!

Is there a more perfect symbol of female spanking authority? Compact, feminine, innocent-looking (to those yet to experience it's authority!) yet exquisitely painful and able to reduce a naughty boy (or girl!) to kicking and tears in mere moments. In my opinion, it's the ultimate 'domestic' spanking implement.

I intend to write a full feature article on this - my favourite (well, love-to-hate, anyway!) - implement, but that may have to wait for when I have more time. For now, I'll have to be content with this new artwork.

With this piece, I wanted to capture the experience of a young man being 'introduced' to it for the very first time. Maybe he's never been spanked at all before, or maybe this is just the first time with the hairbrush? Either way, it's a moment in his life he'll never forget!

As such, I tried to present him having quite a distraught reaction to this particular spanking! Lots of tears, of course - it is a hairbrushing, after all! - but I also wanted to capture the mixed shock and anguish of a "first timer" too... he certainly didn't expect it to hurt this much! I tried for a sense of desperation as well; he knows his spanking is far from over, yet it already burns and stings far beyond what he thought he could handle! He's definitely panicking and fighting against it, with his arm reaching back either to block the blows or even just to beseech his spanker to "Please stop!" or "Not so hard!" or (most likely) "Pleeeease! No more with that brush!"

As for the spanker herself... I see her as perhaps either his step-sister, cousin or babysitter. She seems the perky, spunky, peppy sort normally, but a real meanie when she has a boy across her lap! I rather like her blond pigtails (something of a "cheerleader vibe"?), chunky jewelry (that toe ring just seemed to suit her) and cheeky shorts and crop-top (hands off!), too.

The actual reason for this "hairbrush indoctrination"? Maybe he pushed his sister/sitter too far and she decided "a good dose of the brush" was long overdue for him? Maybe she's spanked him before but her hand just doesn't seem to be working anymore... so she's decided that it's time to 'graduate' him to the hairbrush? Or maybe she's just bought herself a nice new wooden hairbrush and wants to try it out on him... just because she can?

Whatever the reason, she's certainly burnishing his buns with it though... it doesn't seem like she's going easy on him at all despite this being his first-ever brush-spanking!

I'm actually quite pleased with how the 'battle damage' turned out this time... it looks distinctly sore and more "hairbrush caused" than just general redness you might get from "just" a handspanking. I suspect he'll be having serious trouble sitting down in comfort after this!

Famous spanking artist Jay Em once captioned one of his pictures: "The first brushing is forever". I think this young man would heartily agree with that sentiment, don't you?