I've never written threesome smut.
Dean was excited to show Sam and Cass the new outfit he bought. It was a simple sexy red dress, and underneath Dean wore a lacy thong and even a matching bra. He looked in the mirror and admired himself. He looked kinda like a stripper, but he liked it.
"Are you ready?" Dean asked from the bathroom.
"Come out and let's see," Sam said excitedly.
With a smile, Dean opened the door. He felt confident and incredibly sexy when he realized Sam and Cass couldn't take their eyes off of him.
"Wow," Cass exclaimed breathily.
"Dean, you look gorgeous," Sam complimented.
Dean didn't reply, instead he walked over to the bed both Sam and Cass were waiting on, moving his hips sensually as he walked. He climbed up on the bed and straddled Sam. Sam's hands immediately moved to touch Dean's thighs. Dean smirked and took Sam's hand to slide it underneath the skirt of the dress he was wearing. Then Dean looked at Cass, who was next to Sam. He reached over to touch the angel's chest. He grasped Cass' tie and pulled it softly, signaling him to come closer. He leaned in, and Dean kissed him on the lips. As they kissed, Dean was slowly grinding on Sam. Cass pulled out of the kiss, and Sam let Dean have a breath before taking Cass' place. Dean pulled out of the kiss, Sam chasing after his lips. Dean slowly began unbuttoning Sam's flannel. Sam quickly pulled off the flannel when Dean got it open. Dean then moved to Cass, removing the angel's trench coat. He pulled on Cass' tie to loosen it, then pulled it off over his head and tossed it away. Cass swatted Dean's hands away when he started unbuttoning his shirt. He then quickly undid his shirt himself, letting it fall to the ground. When Dean turned back to Sam, he smiled when he saw his younger brother had already stripped himself down to his boxers.
"You weren't going to let me do that?" Dean purred.
Sam avoided the question by pulling Dean in for a kiss. He flipped them over so Dean was under Sam as they kissed. Dean smiled against Sam's lips as he realized how bad his brother wanted him. Dean arched his back slightly as he felt Cass trying to reach the zipper in the back of his dress. A draft of cool air hit Dean's back as his dress was opened. Sam didn't break the kiss as he moved his hands to Dean's shoulders and pushed the dress down, letting Dean kick it to the ground. Sam then broke the kiss to see what Dean had on underneath.
"That looks really good on you," Sam said breathlessly.
"I wore it for you, for both of you," Dean replied, looking to Sam, then Cass.
Cass leaned in to kiss Dean softly. Cass' kisses felt very different from Sam's to Dean. While Sam was more rough and passionate, Cass seemed softer and more loving. As they kissed, Dean's hands moved down to Cass' belt. He undid the belt, then unbuttoned and unzipped Cass' pants, pushing them down as far as he could reach. Cass shifted so they would fall to the floor. Meanwhile, Dean could feel Sam's hand between his legs, rubbing his dick through the thin lace of the thong. Dean resisted the urge to move his hips to get more friction against Sam's hand. Cass pulled out of the kiss to slide his fingers under the elastic of the training like bra Dean wore. The angel pulled the material off over Dean's head.
"Sam?" Dean asked.
"Yes, Dean?"
"I want you to fuck me," Dean pleaded.
Sam smiled to himself as he removed his boxers. Cass opened the bedside drawer and took out the bottle of lube, handing it to Sam. Sam slicked his two of his fingers, and after removing the small amount of material still covering Dean, he pressed one finger into Dean. Dean wasn't phased, so Sam quickly added the second. This time, Dean squeezed his eyes shut and gasped at the pain of suddenly being filled. His mouth, though, was suddenly made busy with Cass' lips. Cass bit down on Dean's lip, making him open his mouth in surprise. Cass took his chance to slip his tongue in to explore Dean's mouth.
After a few minutes of fingering Dean, Sam decided he was ready. Since Cass was kissing him, Sam couldn't judge if Dean was ready by his reaction. He used some more lube on his cock, moved Dean's legs so they rested around Sam's hips, and slowly entered Dean. Cass broke the kiss, letting Dean moan as Sam slid in. Dean tightened his legs around Sam as he arched his back, wanting more of Sam inside of him. As Sam began to thrust, Cass wrapped a hand around Dean's cock and slowly, almost lazily jacked him off in time with Sam's thrusts. A few minutes passed, and Sam sped up his thrusts. Dean gripped the bedsheets around him and moaned loudly. Suddenly, Cass moved his hand away from Dean's cock and replaced it with his mouth. When he felt the warm wetness of Cass' mouth around him, Dean rolled his hips, closed his eyes and tried not to scream out in pleasure. Finally, Sam angled himself to find Dean's prostate. When he found it, Dean arched his back and screamed out Sam's name. Cass' mouth came down on Dean again, setting him over the edge. He came into Cass' mouth with a loud moan. Seeing and hearing him orgasm made Sam come into Dean right after. Dean looked over at Cass. He saw the angel still had a boner in his boxers. Dean let himself sink to the floor next to the bed. He knelt in front of Cass, who moved to sit on the edge of the bed. Dean removed Cass' boxers, exposing his erection. Cass let out gasp as Dean placed his mouth on Cass. He slowly took more of Cass into his mouth, making Cass moan and move his hips. Dean grasped Cass' hips to hold them down as he bobbed his head on Cass' cock. Cass was almost to the edge when Dean looked up at him through his eyelashes. He saw Dean's piercing green eyes and thoughts of him in the dress earlier and the sounds of his orgasm hit Cass. Cass moved his hands to rest on Dean's head, slowly pushing himself further into Dean. He came hard into Dean's mouth. Dean swallowed everything Cass gave, daintily wiping his lips after. Then Dean crawled into bed in between Cass and Sam. Sam immediately wrapped his arms around Dean, holding him in a strong embrace. Cass turned toward Dean and let him tuck his head under Cass' chin. At this moment, Dean felt the happiest he'd ever felt. He thought he was a lucky man to have two amazing and understanding lovers who accepted him, no matter what.
