The first time Dean acted up was at the hospital where they were investigating the supernatural death of a few puppy lovers.

"Look, we didn't mean to um..." Cas turned away from the naked cupid and back at the Winchesters, hoping for some help.

The boys encouraged him in a teasing manor, making him turn back. "Hurt your feelings." Cas continued.

The cupid spun around and latched onto the angel, burying his face in Cas's neck. Dean cringed when Cas cried out in surprise. The cupid spoke into his shoulder, "Love is worth more to me you know I..." The cherub started sliding his hands down Castiel's back, resting them on his hips. "I love love! Love it! And if that's wrong then I don't wanna be right!" Dean clenched his jaw as he watched his angel continue to comfort the cupid.

"Yes... Yes of course I..." Castiel had his arms wrapped around the cherub, before speaking bluntly, "I have no idea what you're saying."

The cupid pulled back, locking his eyes with the angel, his hands still firm against his waist. "I was just on my appointed rounds!" He looked at Castiel pleadingly, "Whatever my targets do after that it's nothing to do with me! I was following my orders!"

Dean tried not to let his voice cack as he saw Cas pushing against the cupid's chest with his hands, struggling. "Please! Read my mind! Read my mind you'll see!"

For a short time, the angel and the cherub gazed at each other, making Dean even more uncomfortable. "He's telling the truth." Cas tried to turn back to the Winchester brothers as he spoke, but was held in place by the hands on his hips.

"Thank you!" the cupid smiled.

Dean coughed. "Wait wait." Dean said as the hands on his angel's hips slowly started to slide even further down his backside. Trying to get his attention, "you said you were just following orders?" He watched as the cupid stopped to nod at him. "Who's orders?"

The cherub laughed, "Haha! Heaven silly! Heaven!"

"Why does heaven care if Harry meets Sally?" Dean tried not to glare as the roaming hands started to move on Cas again.

"Oh mostly they don't. But you know, certain blood lines, certain destinies." He tore his attention away from the angel in his grip for a moment, "Like you!" he smiled.

"What?" Sam spoke this time.

"Yeah! The union of John and Mary Winchester? VERY big deal upstairs. Top priority arrangement."

Cas was really starting to hate this guy. "Wait, you're saying you fixed up our parents?"

The cherub rolled his eyes, "Well, not me but... Yeah." He smiled, then turned his attention back to Cas.

"Haha! It wasn't easy either. They couldn't stand each other at first, but by the time we were done with them... PERFECT COUPPLE!" Cas let out a tiny gasp as the 'perfect coupple' was accent with a light squeeze against his arse.

Dean clenched his jaw. "Perfect?" the cherub nodded. "They're dead!"

Thankfully, the cupid ripped his attention away from Cas and back to Dean, "I'm sorry but... the orders we're very clear. You and Sam needed to be born. Your parents we're just meant to be." Another light squeeze against Castiel's arse.

It took all of Dean's will power not to kill the bastard right then and there.

"A match made in Heaven~" the cherub sang, dancing around a bit, making Cas follow his lead. "Heaven~"

That was the last straw. Dean bolted forward, ripping Cas out of his arms.

"Son of a bitch!" Dean punched him across the face as hard as he could, rubbing his injured fist afterword.

The cupid had disappeared. Cas and Sam were looking at Dean confusingly. "I believe you upset him." Cas said.

"Upset him?" Dean was furious.

"Dean, enough!" Sam intervened. "You just punched a cupid!"

"I punched a dick!" Dean said defensively.

"Are we gonna talk about what's been up with you lately or not?" Sam asked annoyed.

Dean looked at Cas, then back towards his brother. "Or not." With that, he left the room in an angry huff.