Your Dark Promise

Chapter 49

Dean's p.o.v

Cas just kept staring down at him with wide eyes. "You just gonna make an offer like that and not follow through?" He said laughing again.

Cas opened and closed his mouth before getting a grin, "Alright so we're doing this."

Dean was still nude from his bath as he propped his arm under his head, watching Cas strip and walking to the bedside table for lube. "First, I need to prep you. I'll go really slow, and if you're not feeling it after that, then we will stop."

Dean just nodded, watching him. He was a little nervous, but he kept just breathing out, even breaths.

"It's easier if you're on your stomach." Cas said quietly as he slicked up one finger.

"Can I stay like this? So I can see it's you, not get in my head?" Dean asked quietly.

Cas nodded, grabbing a pillow from the top of the bed before tapping on Dean's hip. "Lift up so we'll both have a better angle."

Dean lifted his hips as Cas situated the pillow under him, propping his hips up at a little bit of an angle. He felt a little exposed like this, and as Cas spread his legs on either side of him, he felt even more exposed.

Cas was between his legs but kissed at his knee to one leg, trailing kisses down his inner thigh. He got to his crotch and Dean was half hard, his nerves getting the better of him, but Cas just kissed and licked up the length of him anyway. Dean watched his hands and lips move on him, enjoying this, at least as his dick started to twitch, to come to life more.

"Alright, I'm just going to place my hand down there, okay?" Cas asked from between his legs.

Dean nodded as Cas brought his clean hand to Dean's cheeks, giving them a squeeze each, Dean gave a little smile to this but kept quiet. He brought his finger with lube to him just circling it around his entrance, Dean tried not to tense to this, but his thighs went rigid. Cas massaged at his tight thighs with one hand while still running the other over his entrance. "It's okay, just relax. Everything will be easier if you let your body just be loose."

Dean nodded again, taking more deep breaths, keeping his eyes on Cas.

"I'm gonna press on you. And as you relax, I'll keep pressing, okay? If you can't handle it, tell me." Cas added some pressure to his finger, the tip sinking in just to his first knuckle. Dean's thighs tensed again. Cas leaned his head forward again, licking up his length, Dean tried just to focus on that sensation, nodding a little as Cas pressed his finger in more. Dean didn't know how much of his finger was inside of him, but he felt the stretch, the odd feeling of something being inside of him that he wasn't used to.

Cas kept pressing, keeping eye contact with Dean. Once Dean felt his whole finger make its way inside of him, his knuckles resting against his entrance, he closed his eyes to the feeling. Cas tapped at his thigh, "Eyes on me." He said gently. Dean opened his eyes as Cas kept his finger still inside of him. Dean nodded as Cas started to pull the finger out, pulling halfway before slowly pushing it back in. After the fifth time of doing this, Dean moved his hips a little, getting used to the feeling, even liking it a little.

"How do you feel about a second finger?" Cas asked, watching him.

Dean thought on this before quickly nodding his head, "I'm ready." Dean moved his hips around more, watching. Cas brought the lube back, coating another finger. When he pressed them both to him slipping inside, Dean snapped his eyes closed, turning his head into the pillow. Cas reached for his hand with his free hand and interlaced their fingers together, "Keep going." Dean got out through his teeth a little breathless.