It had now been four months since Gabriel gave Dean wings. Dean now found himself standing on Bobby's roof, shaking like a Chihuahua.
"C-Cas, I d-don't th-th-think I c-can d-do th-this." Dean stuttered.
"It is alright Dean. I will catch you if you fall. Take a breath and calm yourself." Castiel said from in front of him. His wings were unfurled behind him, and dean gasped when Castiel stepped off of the roof. A few moments later, Castiel rose up until he was eye level with Dean. Noticing that his lover was still terrified, castile held out his hand.
"It's okay Dean. I will have you the entire time." Castiel said. Dean's shaking hand found Castiel's, and held firm in a white knuckled death grip. Dean's wings spread out, and Castiel began gently pulling him toward the edge of the roof. With his toes hanging off the edge of Bobby's house, Dean's entire body seized up. His eyes were as large as saucers, darting wildly around.
"Dean, close your eyes." Castiel instructed. Dean more than willingly obliged, shutting his eyes tightly. Castiel grabbed Dean and pulled him off the roof. Dean let out a very immaculate scream, and Castiel cut it off by pressing their lips together. Dean clung to Castiel tightly for a moment before he realized he wasn't falling. Dean slowly opened his eyes and broke the kiss. He looked around and saw in the corners of his eyes that his wings were moving. His grip on Castiel lessened, and a smile like Castiel had never seen before graced Dean's features. Castiel held out his arms around Dean, palms up.
"Dean, rest your hands on mine." Castile instructed. Dean nodded, and pushed himself back by grabbing Castiel's arms and pushing. He put his hand son Castiel's and gripped them.
"No. Do not hold my hands, just rest yours on mine." Castiel said. Dean released his grip on Castiel, and looked at the angel.
"Cas, I'm flying." Dean said.
"Yes Dean, you are flying." Castiel said smiling. "Now, 'm going to move my hands away from you." Dean nodded, and Castiel's hands fell away. Dean was now flying unassisted. He realized this, and his wings faltered, but he quickly righted himself. Dean practically glowed with achievement, and the look on his face showed the childish pride he'd beam with when he pleased his dad.
"Can I- can I try moving?" Dean asked.
"Yes. Just remember what I taught you." Castiel said, moving off to the side. Slowly, Dean changed his position, and propelled himself forward. Dean moved slowly in each direction, and within ten minutes, he was racing Castiel around Bobby's house and the salvage yard. Curious as to the yelling from outside, Sam and Bobby soon found themselves beers-in-hand, leaning on one of the junk cars, watching Dean and Castiel.
"You only beat me because I slowed down for you." Castiel said after landing.
"Nah, I beat your ass fair and square." Dean replied, quickly kissing his angel.