Flashback: Bedtime Series

This series of artworks is actually the oldest of all my work. It was one of - if not the - first works I ever did, and so is a bit "rough around the edges", especially compared to my newest pieces! I was still learning the ropes of how to do this when I made this set.

However, for some reason I know it happens to be one of my most popular works, and I've got several nice emails about it since I opened this blog, even though I wasn't even planning on re-posting it here. So, by popular demand... I present one of my first-ever attempts at spanking art: The 'Bedtime' series!

I don't know why, but I've always had a 'thing' for "bedtime spankings". Maybe it's the childhood urban legends/folklore of "crying yourself to sleep" after a good sound bedtime spanking, something I personally never experienced? Maybe it's the intimacy of a sleepwear-clad spanker and spankee? Maybe it's the idea of anticipation (a bedtime spanking is - at least in my mind - not really a "spontaneous" spanking, but a premeditated and preordained one). I really don't know, and would love to hear others' thoughts on the whole "bedtime spanking" concept, routines and effectiveness, from both the point of view of spankers and spankees.

But first, to the artworks... all nine of them!

"Bedtime #1" (1 of 9)

When making this, I'm pretty sure I imagined the character to be brother and sister (likely "his new older step-sister), or maybe cousins. Her state of dress rules out 'babysitter' for me, and she looks too young to me to be 'mommy' or 'auntie', probably.

Whoever she is, it's his bedtime now, and she's paying a visit to his bedroom (or perhaps summoned him to hers?), and is wagging her finger in his face as she lays down the law. The scenario here strikes me as somewhat "playful", at least from her point of view, so I can almost imagine her scolding here to me somewhat "acted", though the poor nervous young man likely doesn't know this!

Perhaps she's explaining how she won't let him get away with nonsense and disrespect now they're "family"? Perhaps (if his cousin), she's lecturing him on what a brat he's been all day and how he's got this coming? Or perhaps she's just telling him how she intends to give him "hot, hard bedtime spankies" whenever she wants to, and that he'd better not tell anyone about it, if he knows what's good for him!

"Bedtime #2" (2 of 9)

As with most bedtime spanking scenarios, at least as I imagine them, he was likely already told to get undressed for bed before it was time for her to deliver his "goodnight smacking". Typically, I'd expect this to mean somewhat childish pajamas for a young man's bedtime spanking, to really drive home he's a "boy" being smacked and put to bed. However, this particular young man seems to be wearing the more "teen trendy"/"grown-up" sleeping/boxer shorts.

Well, it doesn't seem like it matters much, as she isn't about to leave them on for long! I wanted to have her looking him in the eye as she hooks those fingers in his waistband here... as if she's telling him "Oh yes, these are coming down whether you like it or not!"

"Bedtime #3" (3 of 9)

He's blushing with embarrassment at having his shorts tugged down (and off!) by her, but she grabs his wrists to prevent him covering himself. She's amused at his shyness, and quite possibly even teases him about it! Depending on his 'reaction' down below (which we can't see here, though she clearly can!), she may be amused by that too?!

"Bedtime #4" (4 of 9)

Over he goes! Possibly his first-ever "lap time"? I wanted to make him look nervous, either way, as she settles him into position and raises her hand for the first smack. He tenses up... maybe a last-minute plea "please don't spank me" or maybe just "not too hard"? Or maybe just silent, anxious anticipation?

"Bedtime #5" (5 of 9)

SMACK!!! The first swat of many lands, and it's a stinger! In fact, they're all "stingers"! He's finding out a bedtime spanking is far from 'childish' when it comes to the sting and burn! I wanted to make it apparent that she's not holding back or even giving him much in the way of a "warm-up" here... no, it's straight to the super-stingers from the first smack!

"Bedtime #6" (6 of 9)

Panic sets in as he grabs at her ankles. I wanted to depict his "hanging on for dear life" mixed with "oh noooo!" emotions here. I imagine big "Oooooooh!" gasps of shock and pain; he had no idea it would be this painful! Indeed, his poor bottom is on fire already, but she's far from done with him yet...

"Bedtime #7" (7 of 9)

Tears are running down his face now, dripping on the bed covers and carpet as he squirms and kicks on her lap. Sobbing pleas - "Stop! Please! No more!" - and desperate attempts to reach back and block her swats come at this point, but she knows this just means her spanking is getting through to him and having the proper effect. Perhaps he'll promise her to be good? Heck, maybe he'll promise her anything he thinks she wants to hear? I know I would!

"Bedtime #8" (8 of 9) - Never before published!

Hands that reach back are easily dealt with! So are squirming legs! Firmly pinned and locked into place, she can finish up his bedtime spanking with a minimum of fuss from him now. Well, kind of... note that his face is now a mess of streaming tears and icky snot! Ugh! What a crybaby! Still, she is smiling here, so I guess she's pleased with the reaction she's getting from him, don't you think?

Note: this image - number eight in the series - has never been posted or seen before! It was originally intended to be part of the set but I could never get it to work, so I omitted it... I found it today and polished it up and have included it here, though it's a bit rougher than I'd like in a perfect world (which should also explain the slight difference in lighting to the rest of the series). Still, it is nice to have the series finally "as intended"... consider the extra image an 'exclusive' for this blog!

"Bedtime #" (9 of 9)

Finally, it's all over. Rolled off her lap, he kneels before her, rubbing and cupping his burning hot buttocks and sniffling tearfully as she lifts his chin and makes him look her in the eyes. Time for a few final words, though what they are I'll leave to the viewer's imaginations! Is she telling him off for being such a baby about his spanking? Promising him many more bedtime smacked bottoms in the future? Warning him not to tell what happened? Reminding him she can do this any time, any place? Or just making it known that she expects him to go straight to sleep now... or she'll be back to give him a second dose?! What do you think?

Whatever she's saying and whatever the future holds, I'd bet good money he'll be sleeping on his tummy tonight, eh? And very likely will be crying himself off to sleep!

Anyway, I hope you've enjoyed this trip down memory lane! It's been a rather nostalgic experience for me, since this is - as I said - one of my earliest ever artworks and one of the few 'series' I ever tried (I soon discovered how much work they were, so stuck to single images pretty much after one more experiment). As always, please leave comments on any or all of these pics, and if you want to talk about certain images in the series in particular, just mention the number of it in the comment.