Rosaline was clearing away debris from her twenty-fifth birthday party when her eyes started to swim. She knew that one would be her last. The demon would be coming to take her soul soon… But not without a fight. She understood how silly she had been, selling her soul for her 'true love', only to realise that she could do better anyway. She did do better.
Her boyfriend of three years shot her a quick smile across the room, but it dropped quickly at the sight her saddened face. "Rose, you are you alright?" He was suddenly in front of her, his hands cupping her arms. "Are you unhappy?"
She sighed and looked up into a pair of beautiful blue eyes. "I am, Cas." She paused, took a deep breath, then told him the secret that she had been hiding from him since before they met. "I know how you and your friends are always fighting demons and stuff-"
Castiel interrupted quickly, understanding flowing over his face. "You would like me to stop?"
"No. Cas, that's not it." She shook him off. The moment he knew, he would never touch her again. "When I was younger – when I was fifteen – I did something stupid." She dropped eye contact, and stared at his glossy shoes. "My boyfriend at the time had cancer, and he was dying… So I sold my soul to cure him…"
"Rosaline! Why?!" The items inside the room started to shake with the angel's fury.
She took a step back, fearful. "I had to do something! I loved him! I couldn't let him die!"
It took him a while to calm down, and all that time, she stared at his shoes. She saw them move forward so they were touching her sock-clad feet, and a warm finger gently tilted her chin up. When he spoke, his voice was soft. "Rose…?"
"Yes?"
"Do you know who the demon was?"
She shook her head. "He was British, black hair, black beard, black suit."
"Crowely." Castiel growled, then nodded. "I will be back, Rose. I need to call Sam and Dean."
She nodded, but he didn't see it. He'd already left.

It was getting close to midnight, and Castiel still hadn't returned home. She was restless. It didn't take her long to get what she needed and go to the nearest dirt crossroad. After she had buried the box, she heard a low whistle behind her.
"Well, well, well… What can I do for you now, darling?" She shuddered at the familiar gruff British voice and turned slowly, determined to keep the fear out of her eyes this time.
"Don't you remember me, Crowely?" She raised an eyebrow at the demon. He looked exactly the same as last time, down to shiny coat of his shoes.
Crowley appraised her hourglass figure for a moment, spending a little longer than necessary on her cleavage. "Ah, the little girl who sold her soul for her boyfriend. Long-time no see, eh? How is he? Back together again?
Rosaline rolled her eyes and ignored him. "I was wondering if there was any way I could… Back out of the deal. I don't care if that involves killing that boy, but I can see now that it wasn't worth it."
"Of course it wasn't worth it! Anyone could have told you that!" He chuckled and rubbed his palms together. "But my, my, what he missed out on…" He ran his tongue over his lips, staring at her figure.
She pulled her jacket closer so that it hid most of her exposed chest from his prying eyes. "You didn't answer the question: can I get out of-"
"Rose?" A flap of wings indicated Castiel's arrival. He was beside her, frowning at her whereabouts, and his demeanour changed the instant he laid eyes on the demon. "Crowley!" The angel almost roared, and went to take a step in front of Rosaline.
Crowley was too quick. His fingers curled around her arm and yanked her against him, suddenly holding a blade against her neck. She tried to squirm away from him, but it only made him press the knife harder against her soft skin. "Uh, uh, uh," he whispered in her ear. "I wouldn't be doing that now, my lovely…"
Castiel's eyes hardened and he lowered his angel blade. "What do you want, Crowley?" His voice was deep, and Rosaline could hear a trace of fear in it.
"It's not what I want – well, it wasn't – because she was the one who called for me." The demon tapped her neck. "But now, it seems that Bird has a new toy… Is that right?"
"That is… Correct…"
"Well, isn't that a surprise!" Crowley sounded genuinely amused.
Rosaline, on the other hand, was terrified. Fear was making her heart beat loudly in her ears, and she was certain that the demon could hear it. Maybe Cas, too.
"Let her go, Crowley." Cas's voice had lost its fearful tone, and was replaced by something firmer, a voice that almost promised God's personal wrath upon him if he didn't do what the angel wanted.
That made Crowley laugh. "Well, not without a gift for your beautiful young lady."
Something there was a weird sensation that started in her arm, and travelled throughout her body, making her frown. Castiel on the other hand, went as white as a sheet and ripped her from Crowley's grasp.
The demon chuckled. "Just in case my dear little hound has a little trouble finding Angel Bait. No heaven trips for you." Crowley smirked when he saw Rosaline curl into the angel's chest, face buried. Cas held her tight and stroked her soft brown hair. "Let's go." They both vanished with the sound of flapping wings.
Crowley stood there for a moment, thinking of Rosaline. She had definitely grown into something. It made the demon feel something he hadn't in a while… It pulled on his nearly non-existent humanity. Something about how she felt against him, how soft her skin was, how fragile she was. It made him yearn for her, to have her in his arms and protect her from whatever monster may want to harm her.
He shook it off and hunkered over, digging in the centre of the crossroads. When his fingers hit the tin box, he opened it and retrieved the picture of her. She wore a shy smile, her eyes were bright blue, and her hair was as wavy and reminded him of melted chocolate. He pocketed the photo, already making plans to put it into a pendant that he would hide under his shirt. "Rosaline… Let's see what we can do about you."

She lay in bed by herself while Castiel spoke on the phone downstairs. He had refused to speak to her since he had returned them home, and from what little she could hear, he wasn't speaking in English, so she gave up on trying to find out what he was saying pretty quickly.
Rosaline closed her eyes and curled up under the covers, trying her best to sleep without a person beside her. It had been so long since she had been alone like this. Even when Castiel was hunting with the boys, he would still stay with her until she fell asleep.
She was almost asleep with tears trickling down her face by the time she felt a presence in the room. She felt a warm hand stroke her head, and wiped away the tears. "Shh…" The voice calmed her. "Shh…" The voice started to hum a soft melody in the quiet room. Castiel's voice from downstairs quieted, and she knew that something wasn't right. But she was so peaceful, and the voice was so mesmorising that she didn't care. Sleep consumed her.

Crowley smiled gently at the sleeping girl, watching the rise and fall of the covers as she slept. He could tell from Hell that she was unhappy, and he couldn't just sit there. He needed to see her.
He stayed in her room until the room started to light up from the approaching dawn, and the sound of footsteps echoing up the stairs. He paused for a moment to kiss her cheek, watched a small smile bloom across her face that was better than any sunset he had ever seen, before he left for Hell.