This screenshot looks like Dean just suggested that AU Dean stay so they can have a threesome with Cas. And AU Dean is contemplating it.
(Don’t worry! Cas can take both of them~ Sorry. Or am I??)

seen from United Kingdom

seen from Germany

seen from Kuwait
seen from Germany

seen from United Kingdom

seen from United Kingdom
seen from China

seen from Germany
seen from Italy
seen from China
seen from Malaysia

seen from United States
seen from China

seen from Sweden
seen from China
seen from United Kingdom
seen from United Kingdom
seen from China
seen from Malaysia
seen from Canada
This screenshot looks like Dean just suggested that AU Dean stay so they can have a threesome with Cas. And AU Dean is contemplating it.
(Don’t worry! Cas can take both of them~ Sorry. Or am I??)
From the prompt list, if you want: 50: "It's not what you think it is"
Hey, thank you so much! I appreciate you sending this ask to the absolute max and I'm sorry this took so long to answer. I got some stuff I'm dealing with at the moment and it's taking a toll on me.
I hope you like this! I feel like it might be a little rushed at the end, but it is what is it for now.
Thank you again!
************
10 Oblivious Years to Make Up For
🌟(previously titled Teachers AU)🌟
“Mr. Winchester, why do you hang out with Mr. Novak so much? He’s the history teacher and you’re the P.E. teacher. You aren’t even in the same departments.”
“Well, for starters, he’s my best friend. And second, we have been married for over ten years and he’s the love of my life, so… I think that entitles me to spend as much time with him as I want.”
“You’re married to Mr. Novak?!”
That’s how Dean finds out that his and Castiel’s students and the staff—their friends—of Lawrence High all thought he and Castiel were…just friends.
~~~
Magic School AU Prompt
“How was your first day at the Academy, Cas?”
Castiel looked up at his guide, a bubbly redhead named Charlie, and shrugged. “It seems like all my other schools.”
“Like a normal human school?”
“Yeah…”
Charlie laughed. “Well, good. I mean, that’s kinda what we’re going for. But here, you’ll learn to harness your magical abilities and when you graduate, you get a guardian.”
“A guardian?” Castiel asked, raising an eyebrow questioningly. He was about to ask more about it when a loud commotion drew everyone’s attention and to one end of the hallway. There he saw a group of boys in varying degrees of undressed from the academy’s uniform. They were pushing, shoving, and laughing with each other as they walked down the hall.
Castiel sighed and was about to roll his eyes because they seemed just like the jocks from all his old schools, but he froze when he saw the the one in the middle—the boy who all the others seemed to be trying to get the attention of.
Castiel froze because that boy was absolutely beautiful. Hair that couldn’t decide if it was brown or blonde, freckles Castiel could see even from how far away he was, and when they made eye contact, Castiel’s breath caught in his throat as the purest green he’d ever saw started back at him.
Castiel couldn’t have broken eye contact even if he wanted to as the group made their way towards him and Charlie. When the boy smiled at him and winked as he and the group walked passed, Castiel felt himself blush so hard his ears burned.
Then the boy turned to one of his friends and Castiel could breathe again, but he still couldn’t help but stare at the back of the boys head for as long as he could until the group turned a corner and were gone.
“Ugh,” Charlie said, pulling Castiel back to the present. “You know, I love Dean, but sometimes his friends can really push me close to my breaking point. They can be quite obnoxious—”
“Who was the one in the middle?” Castiel interrupted, “The one with green eyes and freckles. Who was that?”
Charlie‘s face broke out into a smile that she had a hard time controlling.
“Him? The tall Adonis with the eyes like a meadow in the Angelic Forest?” She asked, and Castiel nodded enthusiastically. “Oh, why, that was my friend Dean. Dean Winchester.”
Castiel’s heart leapt into his throat. “What? He’s your friend?”
“Oh, yeah. He’s our best guardian at the academy. He’s only ever gotten top marks in his skills classes,” Charlie said, “Why do you ask?”
Castiel blushed again, looking down at his feet as he picked at his nails. “No reason.”
Charlie let out a cough that sounded suspiciously like a laugh.
“Cas,” she asked, and Castiel looked up at her hesitantly. “Would you like me to introduce you? He’s like my brother, and honestly…” Charlie leaned in, her eyes glimmering as she said, “I think you two would get along really well.”
(insp.)
The Birthday Bee Cake Incident
"Why are you putting a bee on the cake?" Sam grimaced at the cake, moving to poke at it. Dean slapped his hand away and glared.
"Cas loves bees," Dean stated, turning back to put the details on his boyfriend's birthday cake. "And I love Cas, so..."
"Why the crown, as well, then?" Sam asked again.
"'Cause he's my Prince," Dean answered offhandedly as he used his precision tweezers to place a fondant jewel on said crown.
"Wait, what?" Sam reeled back. "He's your Prince?"
Dean froze. "What? No! I didn't say that."
Sam laughed heartily. "Yes you did! I heard you loud and clear!”
"Shut up!"
"Oh I'm never letting you live this down." Sam threw his head back as he continued to laugh. "Do you really call him that?"
"No! Sammy, don't be stupid," Dean said, setting his jaw angrily.
"Oh my god, you do!" Sam sat himself down in a chair before he fell over. The very thought that his older brother—Dean Winchester, notorious flirt and hater of anything and everything chick flick/sappy—called his boyfriend his prince had Sam weak in the knees.
"Shut up, Sammy! Or don’t be surprised if you get a fist to your jaw," Dean grumbled.
"Okay, okay," Sam relented. He was quiet for a second before he spoke up again. "What does Cas call you?"
"Shut. Up.”
“Dean.”
“I'm so not telling you."
"C'mon," Sam pleaded.
"No."
"Are you his king?"
"Sam," Dean warned.
"His Queen?"
"What?! No!"
"His knight?"
Dean hesitated, his face turning red. "No!”
Sam’s body began to shake.
"You're his knight?!"
“Shut your cake hole!”
Sam started laughing. He threw his body back and ended up having to scramble to right himself before he fell over.
"That's classic!"
Dean set down his tools and took a deep breath. He looked honestly angry right now and Sam felt a pang of guilt.
“Sammy, I swear to god—"
"Okay, I'm sorry. Really," Sam said, wiping at the tears that had started to leak from his eyes. "I actually think it's sweet."
"I don't care."
"Honestly!" Sam said. "I think it's great you found Cas."
Dean looked up at him, still angry but getting softer around the edges. "Shut up and let me work."
"Okay," Sam said. He sat back and watched Dean as he continued to lay fondant onto the cake. The angry clench of his jaw dissipated as he worked, being replaced by a smile that Sam had no doubt was caused by thoughts of Castiel.
(insp.)
Dean’s a lucky man.
--
It’s an old joke, but I saw one of those wrong dialogue posts and drew this instead of going to bed. I have no regrets.
Sick & Sound
“I’m sorry I’m making you stay home from school, Dean... I know today was dissection day and you’d been looking forward to it...” Castiel whispered, digging his face into Dean’s neck. Dean turned his head to press a kiss to Castiel’s temple as best he could.
“It’s okay, babe,” Dean whispered, “I can guarantee you that I wouldn’t’ve had any fun knowing that you were home sick with no one to take care of you.”
“But—”
“No buts,” Dean cut him off. “I promise, I’m right where I want to be today.”
“Are you just saying that to make me feel better?” Castiel lifted his head to look into Dean’s eyes.
“What kind of boyfriend would I be if I was lying?” Dean smiled softly at Castiel and leaned forward on instinct to steal a kiss, but found a finger being pushed against his lips instead.
“I’m sick, Dean,” Castiel said, turning his head away to cough, as if for proof of said sickness.
“I don’t care,” Dean said as best he could with a finger against his mouth. Castiel turned back and fixed him with a look of loving disbelief. “Please? Just one kiss.”
“No,” Castiel said with finality. He maneuvered his arm back into the blanket around him and put his head against Dean’s shoulder, sighing happily.
Dean and Cas stayed like that for a long while, almost having a competition of who could stay quiet the longest.
“You know…” Dean broke first. “They say that physical activity is good when you have a cold.”
“Dean Winchester,” Castiel groaned, a smile forming on his face at his boyfriends antics. “We are not having sex while I’m sick.”
“But think about your health!"
“Oh my god,” Castiel laughed, “Is this because I wouldn’t kiss you?”
“What?” Dean feigned hurt. “Am I not allowed to just want to worship my hot boyfriend’s naked body when he’s sick without there being a reason?
“When I’m all better, I’m going to kick you.”
“Kick me into bed and let me love you,” Dean mumbled. Castiel only smiled.
“Sure, Dean.”
(insp.)
Winchester Technology Presents: Angel Companions
Dean Winchester was a man to be both admired and feared. He’d taken over his father’s pharmaceutical company at just twenty-two and rebranded it as Winchester Technology. He expanded the business model to include robots with AI chips, meant to be doctor and nurse assistants, and began mass producing these robots. Within just one year his robots replaced every and all others in hospitals and medical institutions across the globe. The quality of these robots outranked any competition from being able to outdo him or even compete in the first place. The amount of reports of malfunctions or flaws were so small, Winchester Technology Headquarters could count all their files of reports on just one employee’s single, tiny, little hand.