I wanna squish their faces.

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@rauschele
I wanna squish their faces.

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More self-indulgent sirdust lightly inspired from @totalcollapse’s latest chapter in A Wide Collar and Short Leash. I swear these two are going to kill me.
I had to draw this scene from @totalcollapse’s fic A Wide Collar & Short Leash. (Again? Yeah cuz it’s awesome.) I really hope I did this scene justice because Chap 4 was a rollercoaster.
(Phew 😅 This one took awhile!)
Nsfw headcanons for Sir Pentious?
Have you ever seen a cuter bottom in your entire life!? (Oh, also I had to rewrite these TWICE because my cat kept walking on my keyboard and deleting them :)))))))
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Sir Pentious NSFW Headcanons
After arriving in hell and becoming a cobra demon, even Sir Pentious had been surprised at the throbbing second appendage that had grown on his body, his clawed hands stroking the new and second cock as his hood would fly up in both embarrassment and pleasure at his new discovery. However, even if Sir Pentious did thoroughly enjoy the feeling of his own hands stroking his cocks, nothing made him shiver and moan like when you sucked and licked the throbbing pink appendages, the soft feeling of your lips always causing Sir Pentious to pull your hair as tears welled up in his eyes until he could no longer hold back his sobs as his orgasm would rip through his body, his voice peppered with moans always begging you to keep sucking until he had finished cumming down the back of your throat.
Although the feeling of your tongue swirling around Sir Pentious’ cocks usually left him dazed and unable to do anything but sit in pleasure, there were times whenever Sir Pentious would allow his tail to snake up slowly and touch your body. He would always start with your stomach, his tail relishing in the softness of your skin until his tail trailed lower and lower until it was finally able to caress your wet, slutty hole, and the moment Sir Pentious could hear you choke on his cocks from the touch, he would waste no time teasing you until the sheets below you were covered in your own slick.
Sir Pentious has never tried or preferred to harm you in any way, however, those morals would be mostly forgotten once you would begin to ride Sir Pentious, for the moment you slid down onto one or both of his cocks, his clawed fingers would already be digging into the flesh of your thighs, small droplets of blood cascading down your skin. It was in those moments that Sir Pentious would forget the world around him entirely, his mind focusing on nothing but his hips as they desperately rutted up to meet yours, your tight, slick hole never failing to make Sir Pentious moan and whine with pleasure.
But, the feeling of ultimate pleasure wouldn’t wash over Sir Pentious until he was finally ready to cum once more, but this time inside you. At first his moans would start to grow, his words being cut off by his own hissing as your moans would send your demon lover over the edge, but once Sir Pentious could wrap his tail around you and slam you down onto both of his cocks, his strength keeping you held down and in place, that was when he would finally let out one last loud moan as he would allow himself to come deep inside you, his tails grip never once loosening up from around your body until Sir Pentious had finally stopped cumming, his tail quickly uncurling from around you as it would instead gently place you on Sir Pentious’ chest, the both of you gasping and shaking from your previous fun.
Danger and evil are everywhere, Nature called he didn’t care, Who can help the world survive, Who can keep a dream alive? Alive, alive! An awesome alien hero, was destined to hear the cry, A Watcher known as Widget, He shot down from the sky! Woh-oh, woh-oh, Widget the World Watcher Woh-oh, woh-oh, Widget the World Watcher!

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Sir Pentious
Gif request for @horrendoushaddock!
Is Sir Pentious Jack the Ripper?
So, this is a totally crazy theory, I know. But the evidence is oddly convincing. Now I’ll be the first to say this is a wild accusation, and I would not be surprised if this doesn’t end up being the case, but the facts seem to line up.
First of all, the timeline matters. Sir Pentious died in 1888. And what else happened in 1888? The Whitechapel Murders in London from August 31st - November 9th. Jack was never caught. We have no idea what became of him. Some speculate that the reason his murder spree stopped was that he died. If Sir Pentious died after killing his fifth victim, that would put a sudden end to his killing spree.
In fairness, Sir Pentious doesn’t have a British accent, but Vaggie is from El Salvador and she doesn’t have an accent. The characters who retained their accents (namely Alastor and Angel) seem to have a strong connection with that voice. Alastor’s makes sense, as his Midatlantic accent was a popular accent for radio hosts in the 1920s and 30s when he was alive. Angel’s could be more of a personal choice, or an extension of his spider punishment. Angel is a spider demon because he’s tangled up in his family’s “web” of mafia dealings. Mafia have a strong connection to Italian immigrants, and this could be why he retains that Italian/Brooklyn accent.
Sir Pentious refers to Cherri and Angel as ‘whores’, and no other character uses this particular word except for Sir Pentious. Jack’s targets were all prostitutes. Sir Pentious even seems to bear a grudge against Angel specifically, as he tracks him to the hotel to attack him, distinctly chasing the only prostitute character with intention to harm him.
Furthermore, it’s widely accepted that Jack the Ripper wasn’t some common guy in the street. He is almost always depicted as a gentleman criminal, with most theories on his true identity being doctors and local well-to-do wealthy men. So Sir Pentious’ obsession with image and class may well reflect this idea of the elite gentleman status of the ripper. The other issue becomes, why a snake? The loose intention behind demon appearances is to punish or poke fun of the characters, and to reflect their sins in life. But look at Sir Pentious’ design. He’s one of the only characters to be a predatory animal, and not just any animal, but a cobra, one of the most venomous and dangerous snakes. Cobras (and snakes in general) also hunt like Jack the Ripper. They’re slow and methodical, sneaking quietly and silently searching for a victim. They’re cold-blooded and they strike fast, often killing prey before it can react. The added benefit of the cobra is that it can hide and pretend to be other kinds of snakes, as cobras don’t always have their hoods extended, and when the hood is down, could be mistaken for another sort of snake, just as Jack the Ripper could pass himself off as just another London gentleman. Calling a person “a snake” implies that they are treacherous and deceitful, just like a serial killer who passes themselves off as an innocent gentleman. He could also be a snake because a “snake in the grass” is a conniving person you never see coming before they hurt you. Snakes are also slick to the touch, hard to hold on to, and are easily lost among rocks and fallen leaves, just as Jack was a slippery criminal who evaded police capture. As for all the eyes? It could be because he was cautious and perceptive, having an eye in every direction to make sure he wouldn’t get caught, it could be because his killings garnered so much attention that the eyes reflect his fame, or the eyes are part of his punishment. Snakes move along their bellies, and his eyes are on his underside, meaning he has to drag his eyeballs along the ground.
re: sir pentious fashion. Idk how to fashion myself, and, sans popped collar, Id fw that shirt. I know people who wear hats like that. I mean, they're dorks, but its current enough that I'd give the guy from the 1800's some credit? He could be LESS fashionable. (his not knowing how to use his own phone is killing me tho)
Vox is literally sitting there in the car wearing his hat exactly like Sir Pent is. And it looks dumber on Vox because he doesn't have a head. Sir Pent's fashion is fine, the only reason it's being treated like it isn't is because lol Victorian dude isn't supposed to know how to modern. You're doing okay, Sir Pent!
I can't believe that Sir I-Installed-A-Touch-Screen-Control-Panel-In-My-Airship is somehow too "behind the times" to work a smartphone, so instead I've decided that he's got his own phone that he made himself, but in order to download the app for the Gram he had to get some mass-produced smartphone that isn't sophisticated enough to automatically focus and automatically adjust flash the way his own phone does. Him trying to work a smartphone camera is like somebody today used to just being able to click on a browser and get online trying to figure out how to make dial-up internet connect like it's the 1990s.
Are you still taking the prompts? If so could you do “i can’t sleep/can i hug you?” for sir pentious with s/o
(Of course you can, we all could use some noddle daddy 🐍🐍)
You never have any issues with sleeping but this time you did. You tried sleeping but you could and your loving snake lover was getting the feeling that you haven't be sleeping.
"(Y/N), have you been sleeping well, my dear," He asked as he held you close to him as he placed a kiss on your forehead.
"I've been sleeping just fine my love," you said as he looked at you as he took your word as he went about his work.
One night you couldn't sleep again, and this time you wanted Pentious to be with you, so you got up as he was working.
"Penty, I can't sleep... Can I hug you?," You said as he stopped what he doing as he got up and walked to you as he took you back to the room as he curled up to you on the bed.
You felt so safe in his embrace as he smiled down at you as he kissed your lips. As he hugged you tighter.
"Just let me know when you can sleep," He whispered into your ear as he saw you slowly drifted of to sleep.
Reactions to S/O coming home in tears
Requested by: @anitoonzforever
Sir Pentious
-As you would come home crying, he would immediately hug you and ask you what was wrong
-When you tell him you had an absolute awful and stressful day at work, he would demand who caused you so much pain so he could go blow them up
-You tell him it wasn’t anyone’s fault, just the piling up of work and being emotional hurt you a lot
-So he just snuggles you and gives you comfort and snake kisses to make you feel better
Alastor
-As you came home in tears, Alastor’s ears pinned back against his head from the noise of hearing his dearest cry. It was the worst sound in the world to him
-”My darling, what happened? I hate to see you in such a state.”
-He rushed up to you and wiped the tears from your cheeks
-You told him you were harassed by a few demons on the way home, and anger immediately boiled within Alastor, but he kept his smile on
-He made you hot tea and food and cuddles and after he tucked you into bed for the night he set off to find the demons who caused you such pain

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Heyo it's me again! I was wondering if I could maybe get Pentious, Baxter, and/or Loona with a sickly s/o who cries easily? Mayhaps a bit hotheaded but cries as soon as they start getting frustrated? I'm sorry they're all specific, but I'm sure you know that these are all very self-indulgent. Don't feel like you have to rush or anything. ^^
Baxter is a new one for me! I hope I get his personality right. Also I LOVE Loona.
And don’t be sorry, I prefer people to specify because it makes it a tad easier on me.
One last note, I gave the reader this sort of balance disorder.
Sickly, Emotional, Hotheaded s/o
Pentious:
This precious little snake boy will never leave your side. He will stay but your side just to make sure you get around okay.
You’d just grumble and release yourself from his grip, trying to get to your destination by yourself.
But your legs fail to carry you and you fall, and Pentious try’s to help you again. You just give him a look that says ‘I can do it myself.’
Pentious sighs, watching you get up and fall back down again multiple times. He wants to help you, but he knows that you won’t except it until you’re ready.
After probably an hour you are sitting on the ground, face beet red, and tears streaming down your face.
“I just want to walk properly!”
Pentious sits next to you and grabs your hand.
“Darling, I know. But you won’t learn until you except help”
You lean into him, sniffling.
“I know....”
Baxter:
This little gremlin is all over the place. On one hand he loves his experiments, and on the other hand he adores you.
So if you’re in need while he’s messing around with his stuff, he’ll be reluctant but leave his experiment behind. (After a proper clean up of course!)
“How May I be of service?”
He was cleaning his glasses, so he didn’t really see you trying to walk. Once he did see, Baxter rushed to your side.
You shoved his hands away, shaking your head.
“No! I’ve got this, I can do this okay!”
You grip the wall and try to take a few steps, only to collapse onto the floor once again.
For the next hour you continued to try, but failed miserably each time.
You sniffles and looked at your legs. Tears started to fall down your face.
Baxter sat on the ground in front of you, sighing softly.
“You ready for that help now?”
“Yeah...”
Loona:
Loona is cold on the outside and very warm and soft on the inside. So when it comes to you she is this very caring person.
She knows you need to learn to accept help before you can get better at walking, but that doesn’t stop her from trying.
“(Name) come on, just let me help you.”
“No! I’ve got this.”
She just sighs and watches you struggle to walk. After a while you start crying from frustration and lean against the wall.
“You read for some help babe?”
You look at her weakly and nod, wiping your tears away.
“Yeah..”
Valentines with their s/o (Headcanons)
Happy Valentines day everyone! Doing something special for you all today and adding five characters to this one! Which characters you say? I’ll be including Alastor, Angel Dust, Charlie, Vaggie, Sir Pentious. ENJOY! And again, a happy Valentines day to all of you!
(No gifs this time as to save room.)
Alastor
Alastor has never been a really romantic person, so Valentines day has never been a huge deal to him. But after seeing how excited you seemed for it, he decided he ought to do something for you.
He actually had to go to Charlie for advice on what he could do for you.
When you woke up the next morning he made you breakfast in bed.
“Alastor, did you actually make jambalaya for breakfast?”
“Yes my dear, but it’s made with love!”
As the day goes on, he’ll take you out dancing. However long this lasts is completely up to you, as Al can dance and sing for hours on end.
At the end of the day, Alastor has a special surprise for you. He set up a romantic dinner for the two of you on the rooftop of the Happy Hotel. This is complete with a bouquet of roses, him wearing a full on tuxedo, lit candles, his shadows playing string instruments in the background, the whole nine yards.
He even got you a present! It’s a live, beating heart of someone who’s been causing you trouble lately. Well isn’t that just romantic?
At the end of it all, he’s not overly confident in his romantic pursuits. So it’s important to be thankful and let him know you appreciate all he did for you.
In the end the two of you find yourselves under the night sky full of stars, where the two of you wait to see the sun rise together the next day.
Weiterlesen
SIR PEN X FLIRTY READER THIS IS A MIGHTY NEED (but only uf u want to no biggie)
(Of course you can have some request of the snake daddy 🐍🐍)
Sir Pentious x Flirty S/O
Sir Pentious is a mess when ever you so much compliments him.
He is a flustered boi.
You are always touchy with him like giving him hugs, giving him sweet small kisses, and giving him a massage to help him relax.
You love when tries to returned those affection back. But he is struggle central.
"Oh Penty, I need you here with me, I get so lonely with out you," you would say one night as hug him kissing his cheek.
"Well perhaps that tonight I'm in the middle of a project I'm...working on." He trailed off as he looks into you beautiful shimmering eye.
"Oh please Penty, I can help you out in any way my sweet loving overlord," you would said as your words and turn him into a mess.
Sometimes he worries that you are this way towards other but your not, it's only for him.
And you make sure he knows that. That you love him and him alone.
Hazbin Hotel.
© Vivienne Medrano, 2019. gif by, gravitygif. Efecto/PSD: [ ✘ ]
Favor de ⇄ Compartir y dar me gusta ♥ en caso de usar!. No es necesario dar mención de créditos, pero se agradece!.
Cualquier duda o aclaración favor de mandar un correo especificando el problema, e-mail: [email protected].
✦ Bonus:
Hazbin Hotel.
© Vivienne Medrano, 2019. gif by, gravitygif. Efecto/PSD: [ ✔ ] : Tutorial, sougu y pscs5.
Favor de ⇄ Compartir y dar me gusta ♥ en caso de usar!. No es necesario dar mención de créditos, pero se agradece!.
Cualquier duda o aclaración favor de mandar un correo especificando el problema, e-mail: [email protected].

Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
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Sir Pentious x Reader NSFW Alphabet pls?
Hooo boy, this was a good way to start with nsfw Pentious. Thanks for requesting it, anon, hope you enjoy! I used this template: https://the-coldest-goodbye.tumblr.com/nsfw-template
Sir Pentious NSFW Alphabet
Weiterlesen
I had to draw a little somethin for the new hunicast.. :’)