Disclaimer: I don't own Supernatural or anything related to the series.

Warnings: Rated M because somewhat graphic

Pairings: Dean x Castiel, brief mention of Alastair and Hell

It wasn't quite morning yet when Dean felt the bed dip from added weight. Sheets were pulled back as a firm body slid behind him. Only one person would get into his bed at this time of day.
"Cas?"
The kiss on the back of his neck and an arm wrapping around his stomach confirmed the angel's identity. Dean yawned. He wasn't quite awake yet so he didn't bother turning around.
"What are you doing here?"
The angel's naked body was pressed tight against his back and part of him was definitely up. Dean moaned when he felt a hard pressure slide against his ass.
"I missed you," Castiel said before kissing his neck again.
"I can tell."
He could feel the angel grinding against him; his own boxers were beginning to tent from the ministrations.
"Should I stop?"

Out of all the times they've been together Dean was never comfortable with the idea of Castiel doing things involving his ass. He still had some lingering issues to do his time in Hell with Alastair. Cas knew that and never tried to push anything that he was uncomfortable with. It was obvious the angel had thought about doing more things with him but was willing to accept whatever he could get. In a way Dean was grateful for that. Maybe it was because he was still sort of asleep or maybe how much he has grown to trust the angel but right now he felt like experimenting. The steady pressure against his ass felt undeniably good as each thrust send shivers up his spine.
"No."
He felt Cas's hands near his boxers, "Can I?"
Dean smirked to himself, "Do you even need to ask?"

When Dean didn't feel his boxers being removed, the hunter huffed out a laugh. He realized what was going on.
"That means yes Cas."
"Sorry."
His boxers were slipped down his hips and he kicked them away from his legs. He could obviously feel how much Cas wanted him right now. The angel's hands gripped his hips as he continued grinding into the hunter. Dean started moving back against him causing the Cas to moan. He smirked. He knew what the angel wanted.
"You can touch it Cas."
"I can?"
"I'll let you know if I don't like it. Okay?"
Cas's hands gripped his ass and gently massaged it. The angel hummed in pleasure.

Dean was completely awake when he felt Castiel gently roll him onto his stomach. He was curious what the angel was going to do. He had never allowed Cas to take the lead when it came to sex except for their first time. He never knew how much he would end up enjoying it until they did it. The angel had surprised him and it seems he was going to surprise him again as kisses were pressed against his spine with the trail leading straight to his ass. He would be lying if he said he wasn't nervous but he wasn't going to tell Cas that.

Strong hands gripped his cheeks open as one last kiss was placed right above his hole. It took everything he had to not tense when he felt a wet tongue against his opening. He bucked into the motel bed. Tender licks across his opening and it was a strange yet pleasurable sensation. He gripped the sheets on his bed and gasped as he felt the warm wet tongue enter his body. Dean clinched but Castiel continued on. He wasn't sure what he was feeling; anxious and exposed yet really turned on. Dean moaned.

Dean had gotten so into the Castiel's actions that he almost didn't notice he was turned over onto his back. He gazed up at the angel's lust filled eyes. Given their positions he knew what was going to come next. He briefly paused to swallow before nodding his head to give Castiel his consent. The angel pulled one of his legs onto his shoulder. Dean groaned when he felt something hard and warm slowly enter him. He squeezed his eyes shut from the pain. He felt like he was getting impaled and urgently wanted to push out the intruder. Cas's reassuring caresses helped him relax as the angel slid in, utterly filling him. There may have been some extra help from the Castiel's end but he wasn't going to question it. Everything they were doing now was completely new to him. Right now it wasn't as painful but still didn't feel good. Due to his years of experience Dean knew it was normal to need some time to adjust. Given he was with an angel who was known for his patience he wasn't too concerned about time.

After what seemed like hours Dean wiggled his hips to signal Cas he was ready. Gently the angel bucked into him, rocking in and out of him as if he was made of glass. It didn't feel very good still but it wasn't as painful as it was a few minutes ago when he had been clenching. Dean used his leg around Castiel's waist to signal him to go harder by pulling him closer. He moaned loudly when he felt the angel hit something deep inside of him. It was the most incredible thing he had ever felt in his life. Once Cas knew where that spot was, he made sure to hit it repeatedly at various speeds leaving Dean moaning and groaning like he was on the verge of dying. He gasped, shouted and moaned the angel's name with each thrust while Castiel groaned in response. Every thrust felt better than the last. It was like Cas was reading his mind the way he knew when to speed up or slow down and how much pressure to apply. Any other time the thought would have bothered him but now he wondered how he was ever happy with sex before Cas.

He felt so complete and in bliss that Castiel didn't even need to touch him for him to release. Dean almost blacked out from the pleasure. With a loud groan Castiel joined him and together they collapsed on the bed. He gently shoved the angel on his shoulder to get him off. Reluctantly Cas rolled off of him and to lie next to him. Both were covered with sweat and trying to breathe normally.
"You can't tell Sam about this ever."
The angel was puzzled, "Why?"
"Cas, trust me. It's better if he doesn't know."
The angel hummed in response as they stared at the plain ceiling of the motel room. Dean leaned over and kissed him on the lips. Castiel looked up at the smiling hunter before pulling him back down to continue kissing.

Author's Notes:
I recently figured out that most of my Supernatural stories (minus one) can take place in the same alternate universe. This is one of those stories but it can be read as a standalone. My profile lists which fanfics are in the universe and what the order is for those who are interested in reading them.
I came up with the title since the theme of this story is letting go. For Dean he's letting go of what happened in Hell but also allowing someone to willing dominate him for the first time. After all sometimes it is good to let go even though it can be hard doing so.

I'm currently my own editor so if there are any mistakes please let me know.

Reviews are greatly appreciated. It lets me know that you the readers are enjoying my work.