Work Header

Dean in Panties, Five Times for You!

Chapter Text

Pairing/Characters: Sam Winchester/Dean Winchester

Sam gazed on in appreciation as the lace of his newly favorite pair of panties slid across Dean’s hips. They’d each chosen a pair of lacy panties for one another to don as punishment, pending the outcome of a dare gone astray. In this moment, Sam had never been this grateful to win anything in his life.

Dean twitched anxiously on the bed as Sam contemplated where to begin. All parts of his brother were delicious, to be sure, but this was going to be a long night and he wanted to enjoy every moment their hectic lives could spare.

Chapter Text

Pairing/Characters: Dean Winchester/Castiel

Castiel’s confusion seemed to vanish in a heartbeat, when Dean suggested they try something he hadn’t had the nerve to request. Before tonight, he’d never admit that he liked the idea of Castiel watching him stroke himself using his collection of lace and satin.

It wasn’t something he did often. Instead, he saved it to regroup following stressful hunts. He took his time, pinching his nipples and rubbing his hard cock through his panties. He’d always thought edging was the best part.

How could he have known that having Castiel’s eyes on him while he performed would be better still?

Chapter Text

Pairing/Characters: Rhonda Hurley/Dean Winchester

“That’s right. Turn around so I can see that great ass of yours,” Rhonda instructed as Dean strutted around her bedroom. “Bend over a little.”

Dean balked in reply, but quickly fell in line at the snap of Rhonda’s fingers.

“Now, turn around so I can see your cock. Touch yourself for me. Yeah, just like that. You look so fucking hot.” Rhonda grinned at her fly-by-night entertainment and soaked in the moment.

Normally, she would never be this assertive, but with a guy like Dean Winchester ready, available, and temporary, a girl couldn’t pass an opportunity like this up!

Chapter Text

Pairing/Characters: Kevin Tran/Dean Winchester

Kevin fidgeted on Dean’s bed and wondered how he’d lucked out. He’d always carried something of a flame for each of the brothers at one time, but Dean won out in the end. Sexy, confident Dean had him creaming his sheets in his sleep since day fucking one, horrifying revelations aside.

“Relax, Kevin. I’m going to do all of the work here. Trust me.” Dean smiled easily and ran his fingers over his cock that strained against the sheer mesh of his panties.

Kevin wouldn’t have pegged Dean as a panties man, but he was learning to love it quickly.

Chapter Text

Pairing/Characters: Dean Winchester/Crowley

Crowley tugged Dean’s panties down and inserted a lubed finger to work him open. A second finger quickly followed, before the head of Crowley’s cock was pressing in.

Dean felt the breath pushed from his lungs with every inch that claimed him. He’d assumed Crowley had exaggerated the terms of his own demon deal, but it was all truth.

Crowley paused momentarily to shove the panties further down, before he was back in motion, giving Dean the ride he never thought he’d take.

If gaining information earned him dick this good, Dean figured he should make deals with Crowley regularly.