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 - Thrashed By The Maids

"Thrashed By The Maids"

Few spankings are more painful than a caning... except perhaps a double caning!

As Mean Maid Month continues, I bring you a piece that depicts what I see as a truly "nightmarish" ordeal for this young man, as he finds himself on the receiving end of a very sound and severe thrashing at the hands (or rather, canes) of two decidedly cruel (but sexy!) uniformed maids.

Art: The Hairbrush Dance

"The Hairbrush Dance"

There's nothing like an impromptu "spankie dance" by a spankee shows that a spanking REALLY got through to them, I think.

To be in such hot-bottomed agony that you literally jump and prance about the room, frantically clutching and rubbing your stinging, burning buttocks, head thrown back back and howling to the heavens... that's the sign of a well-spanked young man (or young lady... shh!) and - so I'm told - a rather amusing sight for a spanker to watch.

Further, I believe there's few things better for producing a post-spanking "war-dance" than a properly-applied hard wooden hairbrush!

That's what I wanted to capture in this new artwork. Here, a satisfied lady watches as a young man performs what she affectionately terms "the hairbrush dance"; that is, hopping about while sobbing and rubbing his crimson buns like there's no tomorrow! For her, it's the clear sign that he'll remember this hairbrushing for a long time to come! For him, it's the point where he's oblivious to anything else in the whole world except the burning and stinging of his well-spanked buns. Two very different "emotional states"  in the same moment.

When I made it, I imagined that she was his "aunty" (possibly a "surrogate aunt" or even stepmother?) and had just given him a sound hairbrushing before going to bed (hence her somewhat "undressed" state and his nakedness)... this wasn't some totally on-the-spot spanking, but a measured approach to really setting his tender cheeks aflame! Her expression - or at least what I was going for - is one of something along the lines of "hurts, doesn't it?" or "you certainly felt that, didn't you?" or "I think that did the trick, eh?" etc.

What do others think of this scenario? How do you imagine their relationship, and their respective thoughts and mindsets now, post-spanking? And do you think this particular dance he's doing is unique to her hairbrush, or just an all-purpose "ouch-it-really-really-hurts" dance?

Oh, and yes... this art piece IS the origin of my seemingly much-loved "evil aunty" decorative image from this post! I liked how her character turned out so much, I wanted to use her to "illustrate" my blog too, but was saving this original pic to go with the approaching article series.

Art: A Tattletale Earns Him Seconds

"A Tattletale Earns Him Seconds"

This picture (which was the basis for my new blog site's "banner" and logo decorations) came about after wanting to do a new "school" scenario artwork. I wanted to feature both a teacher and a "schoolgirl", and decided to make the latter the "class tattletale".

The tattletale's uniform is admittedly more "adult store" than "real school", but it kinda fits my imagination of this as an exclusive college or private senior high, where the girls are allowed (and encouraged!) to dress as teasingly as they wish!

It also fits with my idea that his erection was likely caused by the mean little tattletale sneakily teasing him (crossing her legs so her skirt rides up, playing with her tied blouse, sucking on a pencil) every time he risked a glance over his shoulder from the corner... and then calling the teacher over in mock-shock when he was visibly aroused!

The boy in the corner, already soundly paddled for some unknown offense (perhaps related to his tendency towards "excitement", though I tend to think it was a more mundane and typical school offense, like forgotten homework or tardiness) is desperately trying to persuade the girl not to draw attention to his involuntary excitement... but of course, it's too late and she's not listening to his frantic "shushes" anyway!

The teacher, for her part, isn't impressed. She probably thinks he's aroused as a result of his sore bottom, the perverted little brat! Well, she'll give him something to be excited about this time... it's back in front of the class and over her desk for a second - and *much* harder and longer - paddling for him now!

And it's all that bratty little tattletale's fault...

Flashback: Birthday Surprise

"Birthday Surprise"

"Happy birthday, darling! Do you like surprises? Well, take those underpants off, lay face down on the bed, and close your eyes, honey... I've got a BIG surprise for you!"

With this old artwork, I wanted to do a birthday spanking piece of some kind, and rather than the typical, I decided to suggest a 'surprise bottom warming' from his Significant Other that night.

While looking at it now, it could be viewed that she's finally agreed to grant him his spanking fantasy wish... but at the time I made it, I had something less-nice in mind, I'm afraid:

HE is excited because he really thinks she's got him something nice, and it looks set to be a romantic evening, too... however, SHE is trying not to smirk because she actually only bought him a sturdy wooden hairbrush to receive his blistering birthday spanking with! (maybe he's only had birthday handspankings other years... or maybe this is his first one full stop?).

Mean, or just all in good fun? What do you think?