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#alastair
casual-trash-art · 1 day
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Trying a new style of shading and idk if I like it
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koemiexists · 1 month
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need a overstim fic w alastor pleaseeeeee and maybe some bondage with his tentacles????
I Wanna Ruin Our Friendship
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summary: alastor is your best friend, you think. but he doesn't want that. and you're okay with it. word count: 1.6k tags: smut, light bondage, tentacles, tentacle sex, overstimulation, monster form alastor, multiple orgasms, breeding kink, creampie, vaginal sex a/n: sorry for the wait!! i have been busy with school, as per the usual... but again!! slowly but surely!! the tortoise wins the race as they say!
You and Alastor were practically best friends. He never said it explicitly, but you knew that you and him had to be really close for him to be so at ease with you. 
Rosie had told you that not once had his smile dropped, even in private with her. You, however, witnessed it one time. It was an accident, sure, you had just looked up at the exact moment his smile dropped from a wide grin to a bit of a grimace. It happened so quickly you almost thought you were imagining things. 
Considering this, if anyone asked, you would confidently say that you and Alastor are best friends.
Alastor didn’t think the same, though, you came to realize when he loomed over your bed one night.
You were upset, to be honest, especially because you barely had time to yank your hands out of your underwear when you heard the telltale sign of him entering.
His shadow had spread out along the wall, staring down at you as you shot up, staring at Alastor, cheeks slightly red. The room was illuminated by two light sources; the constant dim lighting of Hell and all of the artificial bulbs that littered the streets, and Alastor’s glowing red eyes staring straight at you.
“Alastor?” You whispered, tilting your head in question of just why he was at your bed in the middle of the night. Angel had dragged you to a bunch of shopping stores for the entire day, rambling about how your wardrobe was especially lacking, so you were tired, and just wanted to let loose steam before finally sleeping.
In retrospect, you were glad you went along, considering you brought Charlie a new suit that she loved.
A sharp crackle of radio static forced your thoughts back on the Radio Demon’s form, and how he just continued to stare, before clearing his throat, the constant noise altering his voice rising. 
“Apologies, (Name).” He started slowly, gently sitting at the edge of your bed as you continued to silently look at him, your confusion heightening as you began to get apprehensive of what his goal was here. 
Despite the air thickening with static and apprehension, you couldn’t help the fact that you began to get wetter at the sight of Alastor. He cleared his throat, eyes narrowing at your form. 
“Why are you here?” You question softly, removing your covers from your body as you begin to perspire lightly. “You don’t normally come into the women’s bedrooms without permission. You said that it’s not of a gentleman’s nature to do so without courting her...”
He nods lightly, inclining his head towards you as he places his microphone to the side. “You’re correct,” Alastor’s eyes are on you again, glowing lightly as his grin sharpens. “And I am here particularly to court you. Although... it seems I may have interrupted a private matter.”
You flushed, and looked away. “Yeah, you have. Is that why you were acting a bit weird?”
Alastor huffed. “Weird?” His fluffy ears drew back against his head as he rolled his eyes, his grin still present. “I was not acting in an abnormal way.”
Feeling bold, you decide to wake the lion in the den with some teasing. “Oh? Am I supposed to believe that, Al? Obviously, something is up. You’re acting weird around me.” You huffed, crossing your arms as you glared up at him.
“Watch your mouth, dear. I will not be kind to you if you keep talking.”
You snort. “How are you going to shut me up, hm? Is the big, bad Radio Demon going to broadcast my screams? Going to make me beg for forgiveness? Are you going to try and take my soul? Huh?” You’re not sure why you’re so emboldened, and why you’re trying to get a rise out of the one sinner who can kill you in an instant, yet you feel thrilled when you see his brows furrow.
His antlers grew in size, and his eyes became radio dials as his large size towered your smaller frame. His grin was so wide, you felt your heart stop for a moment as his claws dug deep into the side of your pillow, right by your head. 
Alastor watched you yelp in fear, and he can almost smell the way your blood was pumping, the way you began to clam up. “Done?” He spoke slowly, as you nodded. “Good.”
Instead of shifting to his regular form, he just snapped his fingers, and you let out a high pitched squeal when your pajamas disappeared from your body. You were left stark naked, and Alastor only gave you a look, as if to punish you for your behavior. 
“Bad girls don’t get to orgasm once and be done with it.” A tentacle shot out from his back as his shadow self held your legs in order to stop any potential movement you may make. “You’ll take what I give you. And you have made me very upset, (Name).”
You whimpered, but he ignored it, instead pulling a chair up and sitting right next to the bed. His tentacle then went straight to your awaiting cunt, rubbing from the opening of your tight pussy to the tip of your clit. 
Twisting, you let out another squeaky noise, eyes wide and face flushed. Alastor peered at you, but you only let out a gasping ‘green’ as the tentacle plunged deep in you. You shifted again, trying to make the appendage go deeper into you.
“Needy? I barely touched you.” He smirked at your writhing form, the way your hair was splayed against the pillows. Your hips began to buck upwards, trying to get closer to the base of the tentacle. “Who were you thinking of?”
You sobbed out in pleasure, feeling your abdomen tighten as a second appendage began to rub at your clit at a fast pace. “W-what? What are you-” You interrupted yourself with another pleading moan exiting your mouth. 
Alastor rubbed your legs slowly, humming. “When you were masturbating.”
“Before you arrived?” You moaned out, an arm over your head as you hiccuped. “I- It’s embarrassing. This is embarrassing.” You told him, trying to keep your noises at bay. You felt your high cresting, but you didn’t want to cum so quickly. The tentacles kept their touches up, and you bit your lip hard, drawing blood.
He narrowed his eyes at you, the room filling with a cursed energy as he continued his ministrations, ever so slightly speeding up as you barreled to your release. 
You orgasmed around the tentacle inside you, whimpering as the other one rubbed your clit at the same quick pace, throwing you into the side of overstimulation. Crying out, you try to push it out of the way, however two more tentacles come out to pull your arms back. You writhed, your leg automatically jolting out in response to the constant stimulation on your cunt, and you shrieked as Alastor began to tease another tentacle against your already filled pussy.
“Now who?” He inquired once again, watching as you sobbed from the pleasure, tears rolling down your flushed cheeks. His erection pressed against his tight pants, but he just disregarded the pressure, focusing on the way your hair was tousled up, and the saliva dripping from the corner of your mouth.
After another tortuous moment of this, you caved, bucking your hips as your lips parted. “You! You, Alastor! I was thinking- I was-” You moaned roughly, and he smirked as you tried to gain your bearings. “Mm, I was rubbing my wet cunt at the mere thought of you!” 
Humming, Alastor grasped your hips, retracting his appendages that were holding your arms down. He leaned over you, in perfect position to thrust inside if he was bare.
“You look gorgeous.” Was all he breathed out, as you shrieked when the second tentacle at your cunt thrusted inside. You instantly came, whining pathetically for more, even as you were overstimulated. 
The other appendages retracted, and he unzipped his pants to thrust his hard dick inside you. You choked on a moan at the feeling of his cock, especially considering it was thick and long due to his monstrous form. “Al- Mm, Alastor!” You keened, wrapping your trembling legs around his hips. 
With every thrust, the bed shook tremendously, causing the headboard to bang against the wall. In your lust-filled mind, you couldn’t remember how there was others in this hotel, how everyone must have woken up due to the amount of noise you were making-
“No one will see you in such a state, darling.” Alastor groaned through the heavy static in his voice. You let out a quiet whimper as he abused your cunt with sloppy thrusts. He was getting close, and you just wished he’d fill your pussy, to the point where you were stuffed full. 
You were well aware of his questioning gaze at you, and you tried your best to fight through the fucked dumb haze, swallowing a few time as you tried to move your tongue to make sounds. “Breed me,” You stuttered out, looking up at Alastor. “Breed me until I’m full, Alastor, please.”
Alastor growled, and shoved his cock deep inside you, watching as you squirted all over him and the bed from the strength of your orgasm. Your pussy was squeezing him so tight, and he grunted as he pulled your hips flushed against his own, before cumming inside you.
You couldn’t even moan anymore, instead making a tired yet pleasured noise at the feel of Alastor’s thick, hot cum inside your swollen, puffy pussy.
You felt, rather than saw, Alastor slowly become his regular form. He shifted you gently, and you groaned at the way your legs ached. “Apologies, dear.” Alastor said, seeming apologetic as he kissed your sweaty forehead. “You must rest now. I believe you are properly sated?”
Smiling cheekily, you gave him a half-lidded lustful glance. “I may need some tending to, tomorrow.”
Alastor let out a small huff of amusement, smiling genuinely at you. “After I tell Charlie and the others that you’re perfectly fine.”
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angelfangs-666 · 13 days
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sometimes i get stupid ideas and have to draw them :>
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nattycat08 · 27 days
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Charlie is ashamed of her two dad✨️🍎❤️
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the-evil-clergyman · 9 days
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Illustration from Manon Lescaut by Alastair (1928)
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alastortotally · 1 month
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Uhhmmm I kinda like this radioapple ship..👉👈 (IM SORRYY)
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strawlessandbraless · 3 months
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throttle him thursday
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old-glory · 4 months
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Alastair, Crucifixion, n.d.
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carebeardean · 6 months
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we could get somebody else, but we want someone like you!
dean + gun. my chemical romance
w*ncesties dni!🔪
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seasononesam · 3 months
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@suncaptor ​birthday event: day one | dean & alastair
But daddy's little girl, he broke. He broke in thirty. Oh, just not the man your daddy wanted you to be, huh, Dean?
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paigegonerogue · 3 months
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Me: I like this show!
Hazbin Hotel: Stayed Gone
Me: …Well holy shit I didn’t realize this was a fucking masterpiece
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angelfangs-666 · 25 days
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it´s easter or whatever, BUNNY AL!
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winchestergifs · 7 months
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STACKEDNATURAL ⇉ 103.5/327
4.9 I Know What You Did Last Summer Written by Sera Gamble Directed by Charles Beeson Original Air Date: November 13, 2008
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acecroft · 11 months
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SUPERNATURAL 4.16
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alastortotally · 21 days
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Learn a new trick in shading
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becauseofthebowties · 10 months
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4.10 - Heaven and Hell • SPN Time Stamp Roulette (50/?) •
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