I had a bunch of fun making these for the Spanking Slumber Party discord server and I found I really regretted not posting them elsewhere, so here they all are in one post now that all is finished, and next year, I'll post em each day like the art!

Spanktober 3 Oct. 31st: Trick or Treat frankly I don't think these characters need to be named, you know who they are by now I would imagine~ And with this, Spanktober is complete! HAPPY HALLOWEEN, EVERYONE! Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober Oct. 30th: Doll The possessed doll is making its rounds, but it has found a most uncooperative host this time. She flooded Rhyly's mind with all the right thoughts, he just reacted wrong! Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober Oct. 29th: Scream You thought you'd escaped the cursed hairbrush this year... but there is no escape. Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

#Spanktober Prompt #22 - Music Box "Behold, a mechanical marvel! A music box that sings beautifully with the turn of a crank! ... No, you may not look inside."

Spanktober Oct. 28th: Carnival A reference to my old TTRPG game and the effects of eating haunted carnival food, featuring @smolpanda2020.bsky.social ~ Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober Oct. 27th: Tarot "I forsee a beating in your future!" Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober 26th: Scarecrow What good is corner time in an actual corner?? You'll do somethin useful with your time out! Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober 25th: Crystal A continuation of mine and @dolliboi.bsky.social 's Invisible MIschief prompts; Crystal is getting his comeuppance for lettin Ollie take the blame~ Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

Spanktober 23rd: Candles Whoops looks like I forgot to upload this one Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

#Spanktober 24th: Bone Crystal with a bone, being boned, by someone dressed as bones~ Im out of town so check out my previous posts for links!

Spanktober 22nd: Music Box Here we have a Corwyn, who belongs to my friend @courtjestarart.bsky.social , being a pretty ballerina~ Turn the crank :3c make him dance and sing~ Join us on SSP! discord.gg/tJT764jqep or just tag your art #spanktober !

#Spanktober Oct. 21st: Grim Grinning Ghosts Beware of hitchhiking ghosts! They have selected you to join spanktober, and they will haunt you until you create. Now I will post the spanking prompt, and a ghost will follow you home! Hahahahahahahaaa!

Spanktober Oct. 20th: Devilish Just cause Lian is dressed as a priest, he takes it upon himself to punish the devilish Crystal! The holy water doesn't burn, but it makes the holy paddle stings WAY MORE! Dx Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober Oct. 19th: Experiment And even though I know I'm gonna get teased for it, I decided to make an alt showing that Crystal can, in fact, be tamed. Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober Oct. 19th: Experiment Something people like to do on the SSP discord is Crystal taming, which is reacting to Crystal with spanks until he says he'll behave. Aithen, the dom here, partakes in this tradition often. Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober 3 Oct. 18th: Hunter's Moon "Honourable hunter, pursue the echoes of blush and I will channel them into your strength. You will hunt brats and I will be here for you, to embolden your sassy spirit." Blushborne Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober 3 Oct. 17th: Haunted Portrait The piece is based on the changing portraits in the haunted mansion >:3c which reveal their ghostly secret during lightning flashes. Character is Pink1's Magical Girl Bumble! Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober Oct 16th Sleepwalk Ah yes bed time, the time when an adult can indulge in all the embarrassingly adorable ageplay accoutrements, and no one will see, right? ... no one will see, right?? Character owned by/is Dreyer Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober Oct. 15th: Were-Creature The full moon falls upon @wuffywufferson.bsky.social , transforming him into the most dreaded beast of all A WERE-HUMAN! Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober Oct. 14th: Ghost Train This ghost train wont kick you off for not having a ticket... but you will spend the entire trip like this~ And maybe get your clothes back at your stop. the sub is Arkham Insanity's Oberon! Join us on SSP! discord.gg/QGSArkscQg or just tag your art #spanktober !

Spanktober 3 Oct 13th: Mummy Beware the mummy's curse~ Or cursing in front of Mummy. That'll also get you in trouble The dom is Sekhet, who belongs to Leila! ! And the sub is Sally, who belongs to Sally! Join us on SSP! discord.gg/588NTPuc or just tag your art with #spanktober !

#Spanktober prompts 10 and 11 in panorama~

Spanktober 3 Oct. 12th: Invisible Mischief All the great and terrible things one could do with invisibility and Crystal uses it to prank his mommydom Amelia. And Ollie is certainly going to be blamed and spanked for it~ Join us on SSP! discord.gg/QGSArkscQg or just tag your art with #spanktober !

Spanktober 3 Oct. 11th: Gargoyle Amber the Gargirl is who spanked that naughty Paladin/Champion/Seraph Robin in the previous pic! You don't mess with Amber's graveyard or you get got! (I keep forgetting to post on time!) Join us on SSP! discord.gg/QGSArkscQg or just tag your art with #spanktober !

Spanktober 3 Oct. 10th: Grave This naughty Paladin/Champion/Seraph was assaulting the undead ghosts of a certain someone's graveyard! Whose? Weeell, (see next picture!) The character is named Robin, and belongs to Peeker Join us on SSP! discord.gg/QGSArkscQg or just tag your art with #spanktober !

Spanktober 3 Oct. 9th: Faustian Bargain Damnit I keep forgetting to upload these even though I am doing them on time! original description: "Be careful what you wish for~ you don't know who might be listening~" Join Spanktober on SSP! discord.gg/fTAZMMZVKh or just tag your art with #spanktober !

Spanktober Oct.6th: Puppet welp I forgot to upload this yesterday = u =; I did *do* it on time but there goes my perfect upload record for this year This is Count Kevula from SSP getting magic puppet'd~ Join Spanktober on SSP! discord.gg/fTAZMMZVKh or just tag your art with #spanktober !

#Spanktober Prompt #3 - Jack-o-lantern

Spanktober Oct. 7th: Raven A warning to all of the dangers of letting your chastity cage's key be too shiny~ The Character is Fritz, and belongs to, well, Fritz! Join Spanktober on SSP! discord.gg/fTAZMMZVKh or just tag your art with #spanktober !

Spanktober Oct.6th: Captive I kinda love how dramatic Crystal is being here x3 Join Spanktober on SSP! discord.gg/fTAZMMZVKh or just tag your art with #spanktober !

Spanktober Oct. 5th: Gothic “Who dares insult us with this blasphemous mockery? Seize him and disrobe him—that we may know whom we have to paddle, til sunrise, on the battlements!” -Masque of the Red Butt Join Spanktober on SSP! discord.gg/fTAZMMZVKh or just tag your art with #spanktober !

Spanktober Oct. 4: Haunted Hayride I think Rosie sees something neat over there~ Join Spanktober on Spanking Slumber Party! discord.gg/fTAZMMZVKh or just tag your art with #spanktober so we can see all your lovely creations!

#spanktober Prompt #2: Hypnosis

Spanktober 3 Oct. 3rd: Jack-o-lantern Laurel, what have we told you about putting random things in your mouth? Laurel belongs to @dolliboi.bsky.social Join Spanktober on Spanking Slumber Party! discord.gg/fTAZMMZVKh or just tag your art with #spanktober so we can see all your lovely creations!

‪ Spanktober 3 Oct 2nd: Hypnosis First Nikki >:3c then the rest of you! Join Spanktober on Spanking Slumber Party! discord.gg/fTAZMMZVKh or just tag your art with #spanktober so we can see all your lovely creations!

First prompt for #Spanktober2025 #1: Red

Spanktober 3 Oct 1st: Red Some vampires mesmerize with their eyes. This is how vampire Crystal does it~ Join Spanktober on Spanking Slumber Party! discord.gg/fTAZMMZVKh or just tag your art with #spanktober so we can see all your lovely creations!

Spankober 3 is finally here! Come play with us on Spanking Slumber Party! discord.gg/fTAZMMZVKh or just tag your art with #spanktober so we can see all your lovely creations!

Rhyly is such a good boy, how did he earn a spanking? @dolliboi.bsky.social helped me with the backround~ #Spanking #art #ageplay #chastity #buttplug #pacifier #ABDL #sissy #femboy #crossdress

Sometimes I draw girls! This is Charity, a TTRPG character that ended up captured in a kink campaign. She's havin a time. She looks too much like my vampire queen character... I need to change Charity's hair later. #spanking #breasts #bondage #BDSM #dungeon #ridingcrop #nudity

Ollie also got in trouble because @dolliboi.bsky.social also needs to do his art homework~ (our cute way of referring to commissions, in case I've never made that clear) Ollie is an adult. #Spanking #cornertime #chastity #buttplug #sissy #femboy #bottomless #kemonomimi #ageplay #mouseboy #pacifier

Hey it's art from this year for once! I forget if I've uploaded this already Just Crystal paying for my transgressions, as usual~ Don't feel bad for him, I pay for his transgressions all the time. #Spanking #cornertime #ageplay #chastity #buttplug #pacifier #ABDL #Bottomless #sissy #femboy

still uploadin art from last year. This one I just needed to get back into practice, so I drew a kitty Crystal~ #spanking #petplay #tailplug #chastity #pacigag #ageplay #ABDL #sissy #femboy

Unfortunately we have to take a break from Damien's Babysitting, I havent made the next one... a year later x3; Here's puppy boys Damien and Crystal getting some pet play in at the hot spring comm'd by @liankoakland.bsky.social #Spanking #tailplug #petplay #sissy #femboy #chastity #blowjob

Turns out even a noddle armed subby Little like Damien has enough strength to turn on a spanking machine~ #spanking #ageplay #ABDL #machine #diaperposition #sissy #femboy #paci #gag #bondage

So, Damien is a Little and a sub; his spanking arm is not strong or practiced. Crystal's pain tolerance is much too high for sissy Dami's noodle arms~ he's use to being properly thrashed by actual doms, after all! #Spanking #ageplay #ABDL #nursery #sissy #femboy #bottomless #OTK

Another in the Damien Babysitting chronicle~ As he settles more into being Mommy, he's dressing up like his mommy dom, Charlotte~ (who belongs to @dolliboi.bsky.social ~), matching her signature colors and dress~ #ageplay #ABDL #sissy #femboy

The next in the series of commissions~ This is Damien's first idea for taming naughty Crystals~ #Spanking #ageplay #pacifier #ABDL #chastity #sissy #femboy

I was commissioned to do multiple pictures of Damien babysitting Crystal (both adults, just ageplayers). Damien, a Little, has had ideas of how to quell Crystal's naughtiness. #spanking #ageplay #ABDL #sissy #femboy #bottomless #chastity