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Monday, 21 November 2011

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?


  1. Very nice dark red buttocks!!
    I like it very much!
    Greetings from venbergen

  2. This picture is a trap for the boy. The hands on her bikini says "Touch Me" but she forgot to say "For your own danger". So this is the result. A very nice drawing Banjo.



  3. She's a babysitter in my mind and definitely giving her young charge a good introduction to that most traditional of babysitting aids; the hairbrush. I wonder exactly why he's being spanked, though, and the handprints on her top make me think he got a little too fresh while they were fingerpainting and left his mark on her.

  4. Wow! This one is an absolute fantastic piece of art! I love the spanker, she is great!

  5. i think this could be titled "how a spankee is born". while it is hurting while the spanking is going on, i am sure he is aware of the erotic aspects of it. the embarrassment of her making him strip in front of her, the scolding while looking at her wonderful lap he is to go across. the apprehension of how much this will hurt. the amazement of how much it stings when the hairbrush actually smacks his bottom.the begging and dancing while across her lap. the relief when allowed to get up. how pretty she is while after spanking scolding him. then she seals it with a hug and warning that she will spoank you whenever you need one. after laying in bed and realizing how sexy she was. then a nice slow wank and he is hooked for life.

  6. She is the babysitter and hot as hell, love the pic and the story. Great spanking, love to hate the brush

  7. She's his older step-sister and she caught him peeking while she was changing her clothes. He knew his Mom would paddle him and so he accepted her offer of a spanking from her instead. She knew she could fry his ass good and he wouldn't tell so she took advantage of her freedom to strip him and paddle his naughty little bare ass good.

    A spanko and a spankee are both born...


  8. Whether babysitter or step-sister, this girl is hot! The blonde hair in bunches, the crop top with the naughty, novelty design, the panties with the sporty side stripes, the chunky bracelet and the tiny toe ring: she exudes the sexuality of a feisty college girl, and her meanness when she has a boy over her knee and a hairbrush in her hand is truly awesome. He may be new to this or he may not be. Either way the pain is clearly excruciating.

  9. I'm figuring that this boy's first hairbrush walloping (a nude one at that) from his pretty, strict female disciplinarian, will never be forgotten by him--nor perhaps by her either.

    I especially appreciate the annoyed, determined expression on her face--she's obviously not planning on stopping anytime soon... --C.K.

    1. @Crimson Kid
      Thanks! I spent a lot of attention on her expression, going for exactly that! And yes, I don't think he'll ever forget "the first time"!

  10. I really like this one. Like others, I picture the girl as a college-aged babysitter who is spanking a teenaged boy who felt he was too old to be spanked as well as too old to be babysat for. She is teaching him otherwise.

    1. @Gary
      Looking at it again, I think that's who I see her (and him) as too: a feisty college-age babysitter he thought was 'cool' but is really 'tough'!

      She'll put the 'baby' into 'babysitter' by the time she's done with him, too ("Not so grown up now, are you 'little boy'?" *sob*).

  11. The pain is excruciating indeed! And at the moment the boy is only wishing his suffering to stop. Later however he will probabably get hard every time he reminds this scene.

    This girl is an intriguing one. She looks and dresses like a bimbo and makes you want to touch her breast or pinch her bottom. Such behaviour can get you in a big trouble though (as depicted)...