Three's Company (Crowley x fem!Winchester reader x Cain)AU

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(a/n: This involves a polyamorous relationship so don't read if that's not your thing.)

You smiled as you walked into work that morning. No one else was happy to be in the office that early on a Monday morning, but you had your reasons. Those reasons being your bosses. Mr. Crowley and Mr. Cain. You were in a relationship with both of them and things were good. At least you thought they were until that particular morning.

While you were certain things between the three of you were fine, Crowley and Cain disagreed. They'd hoped to work out their problems without you finding out, but that was proving troublesome. Because they were higher ups in the company, they worked odd hours and it was getting to the point where you spent more time with Crowley than with Cain and it caused a lot of tension between them in the office. It upset Cain to no end and he spent a good amount of time fighting with Crowley.

That's what they were doing when you entered the office. Your brow furrowed at the sound of raised voices behind the door so you quietly approached Cain's office door. You knocked and heard a very gruff, "Come in," from Cain. It was unusual for him. You opened the door and found them both glaring daggers at each other. They turned to you and smiled for a moment before returning cold gazes to one another.

"What's going on?" you asked softly as to not attract outside attention. "Close the door please, Y/N," Cain said as he turned to sit at his desk. Crowley placed his left ankle over his right knee and he sat back in his chair across from Cain. You closed the door and took the seat next to Crowley. "What is it? I've never seen the two of you so upset with each other," you said, your gaze flicking between Cain's cool blue eyes and Crowley's rich hazel ones.

"This isn't working out anymore, Kitten. Cain here is upset that you have been spending so much more time with me than him and I can't say I blame him. We did have a deal, after all," Crowley explained, not once taking his eyes off you. You looked at Cain, a frown etched deeply on your face. "Is this true? Why didn't you say anything? You never complained. I know you work late nights, but you could have said something. Anything! I would have been here."

"I know that. It is not only that. Having to share you has been putting a strain on my working relationship with Crowley. I am afraid you have to choose. One of us or neither of us." Your jaw dropped open as you searched his face, hoping to find some hint that this was a joke. He couldn't possibly be serious. However, one look at his face and you knew he was.

"I-I...how can you ask me to do that? I love you both. How can you make me choose?" you were fighting back tears. You'd been in a relationship with both men for over two years. How could they expect you to suddenly just drop one or both of them? You couldn't do it. You wracked your brain for some way to save your relationship because, judging by their body languages and the looks on their faces, they really didn't want this end either.

You licked your lips and flicked your eyes between them both again before asking, "How much vacation time do I have saved up?" Crowley's brows rose and Cain cocked his head to the side as he answered, "About a month." You nodded. "I'd like to make a proposal. I take my vacation time and split it in half with both of you. Two weeks each. I want to save this relationship if I can. Please?" They exchanged a look before they both nodded. You smiled at them then got up, kissed them both on the cheek and left the office.

*one month later*

You were sitting on your bed, talking to your brother on the phone while Crowley was in the shower. The two of you had just gotten back from your two week vacation together. You'd hoped the vacations with both him and Cain would help to ease whatever tension there was between the two, but you wouldn't know until you all returned to work the next day.

"I have no idea whether or not it worked at all, Sammy! What if they still make me choose? I don't know if I can do that," you told Sam. While both your brothers had accepted your relationship with Crowley and Cain, you could talk to Sam about it a little easier than you could Dean. Dean didn't want to know anything about his sister's love life. "Relax, Y/N. If it didn't work, you'll know by tomorrow. Look, they both love you. That much is obvious and, if they what you to choose it's because they believe you can't be happy with the two of them at each other's throats. Just be honest with them. They're...somewhat reasonable. I'm sure they'll understand."

You smiled as you heard Crowley turn off the shower. "Thanks, Sammy. I'll call you tomorrow night?" Sam agreed and you hung up just as Crowley came into the bedroom, a soft smile on his lips. "I take it you were talking to Moose?" You nodded and leaned up to kiss him. "I have to go, but I will see you at work tomorrow," you told him and left, ready for whatever the next day brought.

It was quiet in the office the next day when you arrived with your boss' coffees. The door to Cain's office was open and you could see both men inside. At first, you were worried, but then you realized that they were simply talking, not fighting. You knocked on the open door with your free hand. They turned to you and smiled. "Good morning, Y/N."

"Good morning," you greeted, eyeing them warily. "Come in and close the door." You did as you were asked before turning to face them both again. "We believe we've solved our little dilemma," Crowley said, handing you a piece of paper. "A new schedule?" They both nodded. "With this new schedule, it will be easier for us all to have equal time together. What do you think?" You pretended to look it over, knowing that you really didn't care. You got to keep both your partners! Without a word, you threw your arms around Cain and then Crowley, loving the feeling of being able to hold them both.  

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