†Supernatural x Male Reader Oneshots†

Stealing (3)

: Dean Winchester

* Please read the other parts on this book! Also yes this includes SMUT, and because its been a while...here is some bottom Dean!!! thank you for reading :D
* I have not written smut in a WHILE so excuse if it sucks, i think i did good...but who knows lol

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Deans fingers locked in on Y/n's hair, tugging it ever so slightly when the hunter felt a little too good. This had been the first time in ages that Dean Winchester allowed himself to be with someone of the same sex, as embarrassing as it was—Dean wasn't completely used to this.

Dean opened his eyes and looked down at the man who was giving him so much pleasure. Y/n was skilled; in the back of Deans mind, he wondered why this felt better than the many times he had done this with a women. Soon enough Y/n lifted his head and smirked at Dean, wiping his mouth a little before sitting up fully between the hunters legs.

Dean was out of breath, while Y/n seemed to be more composed. They sat staring at each other for a moment before Y/n chuckled breathlessly, it was becoming a little awkward.

"Hey, Dean? You there?"

"Huh...? Oh yeah, sorry i think i spaced out..."

Y/n shook his head and leaned down to kiss the hunters lips softly, in an act of helping him feel better. Dean kissed back and put his hands on the sides of
Y/n's neck. Y/n pulled away and sat up again.

"Are you ok, Dean?"

Deans breath hitched as he felt the others hand caressing his thigh, he knew this was coming—yet for some reason he was surprised it was happening so soon. He wasn't scared of this, no way, Dean Winchester was never scared...but this proved to be different from the other times he had with men.

"Yeah...im fine."

Y/n furrowed his brows not completely believing the hunter, but Dean gave a look of wanting to stop talking about it. Instead to show that he was willing and ready, Dean sat up on his elbows and spread his legs apart just a little. Y/n smiled and reached over to his bedside table, opening it and grabbing a little bottle of flavorless lube and a condom.

Dean watched as Y/n put the condom aside and opened the cap, squeezing some onto his fingers, the bottle was tossed aside waiting for another use while Y/n looked at Dean, silently asking for permission. Dean took a breath and nodded softly, closed his eyes and relaxed his body.

Y/n kissed Deans scarred chest and softly put a finger to the mans entrance, tracing around it to insure there was enough lube coating it. Dean held his breath, feeling his body start to react to the feeling that he hasn't had in a long while. Y/n continued kissing Deans chest softly as he pushed his index finger inside, slowly going past his middle knuckle.

"Relax, Dean. You're doing great."

Y/n praised, using his other hand to rub the other mans thigh. Dean hummed and tried to relax himself, but it was proving to be more difficult than he would have liked it to be. Y/n's words of praise were helping, Dean couldn't deny that he enjoyed being praised every now and then.

The slow pumping of Y/n's finger continued, but this time he added another, and then another. Dean felt like he was in heaven, and this was quite literally only the beginning. Deans soft moans filled the room, and soon enough a little whimper when he felt
Y/n's fingers start to pull out. Y/n chuckled and reached over for the condom he had grabbed earlier.

He opened the packet and pulled the already lubbed up condom out, taking a little breath before rolling it over his hard on. Dean now knew he had to prepare himself more than ever, sure he was excited, god he was so excited for what was coming next, but that didn't stop that tingle of fear as he felt Y/n get into position. Y/n's member slowly tried to push in, with Y/n holding onto Deans hips to steady himself.

Dean leaned his head back into the pillow and hissed as he felt Y/n start to go further inside. There was a burning sensation coming from inside of Dean, he felt a trickle of tears come from his eyes at the little bits of pain he was feeling. Y/n bit his lip at the sudden heat consuming him, it was clear that Dean had not been having sex like this for a while. After bottoming out, Y/n stayed still for both of their sakes, breathing deeply in and out to steady himself.

Dean felt that familiar knot in his stomach already, but he desperately tried to keep it at bay. Y/n leaned down and kissed Deans beck softly, hoping that, that would somehow help him feel more relaxed. It worked, mildly, Dean took a deep breath and breathed it out softly. He opened his eyes and looked at the h/c man above him, they locked eyes and Y/n used one of his hands to caress Deans cheek.

"How are you feeling, Dean?"

Dean swallowed some spit and nodded a little, saying softly:

"I'm...okay."

Y/n nodded and wiped a stray tear from Deans cheek. Y/n moved his hand back down to Deans hip along with his other hand and slowly started to pull out, causing Dean to grip onto the blanket under him. Y/n waited a second and pushed back in, as softly as he could. Dean hissed and felt his legs start to twitch, the knot in his stomach growing with each slow thrust.

After doing this for about a minute, Y/n started to speed up his pace. Dean let out a soft moan as he allowed his grip on the blanket to lessen ever so slightly. Y/n moved his hands from Deans hips to Deans thighs, holding them from the bottom and using this as an advantage to get deeper inside. Dean gasped and breathed heavily as this continued.

The bed started to shake as the thrusts got harder and faster. Dean felt his mind start to escape him, the only thing he could latch onto was the close but distant feeling of release. He tried keeping his moans at bay, not wanting to seem like a chick or something, but there was those moments were he let them loose. Y/n loved it, he smiled and went faster, begging silently for those sweet sounds to come out more often.

Dean hissed at the feeling of his end coming quicker and quicker. The pit in his stomach became almost painful as he tried to hold it back—it had only been around 5 minutes, god, how pathetic he felt. Y/n huffed and felt his upper body strength start to escape him, his arms gave out slightly, making him need to lay down on top of Dean.

Dean hummed and jerk his hips upward, now feeling warmth against himself. Y/n kissed Deans neck softly, letting the Hunter know he was coming close to the end. Dean silently thanked whatever god was out there that he could finally release. And so he did.

Deans head laid back on the pillow and he let out a low groan, huffing out as he felt his cock twitch, his load finally leaving his system. The man above him hummed and used whatever strength he had left to lift himself up and release himself as well.

Dean didn't notice, nor did he care. His head was to the side, trying to catch his breath as he felt Y/n slowly slip out of him. Dean hissed and closed his eyes, whimpering quietly. Y/n put a reassuring hand on Deans chest, softly caressing it as he continued to pull all the way out.

After a second or so, Y/n threw off the condom into his trash can. He breathed heavily as he laid beside Dean and put an arm around him. Dean hated to say it, but he was really thankful to be getting some kind of attention.

"God, your wonderful, Dean."

Y/n kissed the side of his head and grabbed the blanket from beside them, tossing it over the two of them. Dean hummed and leaned his head back onto Y/ns shoulder. He had a lot of things to worry about, but all he needed to think about now, was Y/n.