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Prompt: Feel like taking another request? How about Weecest with crossdressing!Sam and super sweet sexy time? Praise!kink, maybe? Please and thank you. <3
Sam twirled in the mirror, admiring the red panties against his ass. They were lace and soft and hugged his ass in just the best way. His cock was straining in the tiny fabric and pushing the silk away from his body. The lip-gloss tube was lying beside him as he used the brush to paint the pink, cotton candy flavored gloss on his lips. There was a tiny bit of kohl under his eyes which Katie assured him would make his eyes look beautiful. And she was right.
He grabbed the skirt and put in on. It rested perfectly on his hips and the tight silk shirt contorted to his muscles. He was beautiful.
He glided out of the bathroom and watched Dean on the bed. His older brother had his head buried in a magazine facing away from Sam. “Oh De-ean,” Sam purred. “What do you think?”
Dean dropped the magazine and turned around. “Why are you bugging m–,” He froze. “Holy shit, what are you wearing?”
Sam’s head fell. “You don’t like it?”
Dean’s eyes widened. “Oh god no. I mean, I don’t not love it. I love it, you look so sexy,” Dean said. “Holy fuck you’re practically edible.”
Sam flushed happily. “You think?”
“Oh yes,” Dean assured. “I’d really like to peel those clothes off and lick you all over.”
“Oh yeah?” Sam regained some of his confidence. “You gonna do something about it?”
Dean stalked over and grabbed Sam’s skirt. “C’mere, baby boy. You look so gorgeous right now I can hardly take my eyes off you.” He guided Sam to the bed and kissed his glossy lips. “Hmm… you taste sweet. I like it.”
“Cotton candy,” Sam replied.
Dean slid his hands underneath Sam’s skirt. “I did this to plenty of women, but they never had something so big underneath.” He squeezed Sam’s cock. “I never really liked eating girls out, but you’re a whole different story. I’d like to lick and suck your dick all day. I love the taste of you.”
He preened with all of Dean’s praise. Sam’s cock begged to be released from its satin prison. “Dean.”
“Oh baby boy, you look so pretty I want to fuck you with these clothes on.”
“You can,” Sam replied immediately. Dean lit up.
“Get onto your stomach,” Dean demanded. Sam acquiesced and felt Dean flip the bottom of his skirt over Sam’s ass. He pulled the panties down just far down enough to expose Sam’s hole. The fabric rested against the bottom of Sam’s thighs and every time he shifted he felt the lace leave an imprint in his skin. Dean spread his cheeks apart and put a finger on his hole. “I wasn’t kidding about wanting to eat you,” Dean said. He kissed the small of Sam’s back and then grazed his tongue down Sam’s body until he was lapping at Sam’s hole. The little pink pucker stared invitingly at him and Dean slobbered over it, getting it nice and wet and wiggling his tongue inside.
Dean remembered the first time they did this. Sam was so grossed out he almost pushed Dean away. The older Winchester persevered, however, and then Sam had to admit how wonderful it felt to have Dean’s tongue eating him out. Dean liked the way Sam tasted. It was unusual and musky but so wonderfully Sam that Dean felt addicted. And anything that made Sam whimper was worth it. The lace rubbed against Dean’s neck and his nose bumped the skirt. He didn’t think he’d ever been so horny as he had the moment his baby brother came strutting out of the bathroom with his skirt and tight shirt on. And the lip-gloss. Oh, it tasted so wonderful. It made Sam’s beautiful lips all shiny and wonderful.
Dean wanted Sam to dress up like this every night. He wondered if Sam would go for it. Maybe he would even make Sam wear the panties regularly. He could buy his brother a couple more pairs in different colors, maybe some pinks and purples and blues. He grinned against Sam’s ass. He wondered how Sam would feel about wearing panties when Dad was around, trying to control his arousal. He could really abuse this kink of Sam’s.
Sam kicked his leg out. “Taking a break, Dean?”
“Just admiring the view,” Dean replied. “You’ve got the ass of a porn star. Firm and soft just like I enjoy.”
“Better than a girl’s?” Sam asked.
“Girls are all soft,” Dean said. “I love their bodies, sure, but I can’t fuck them hard and wild like I can with you. It’s wonderful to have the kind of amazing sex we have along with love. No girl can do that for me. You’re my perfect little baby, my sweetheart. So good for me.”
Sam grinned into his pillow. “My dick is feeling kind of neglected.”
“You’re pretty needy,” Dean said. “I’ve half a mind to leave you hanging.”
“But you won’t,” Sam chirped.
“But I won’t,” Dean agreed. “Because I’m a good brother.”
“A good brother than fucks his baby brother,” Sam pointed out. “Well, right now he’s too much of a pussy to fuck me bu–,”
Dean flipped Sam back over and breathed over Sam’s pretty cock. The lace was soft and the skirt fanned across Sam’s hips. His lip-gloss was smeared and his eyes glowered like a cat’s. He was so beautiful Dean thought he might explode. “There’s my pretty little girl,” Dean crooned. “My pretty baby.”
Sam’s eyes flickered shut as Dean sealed his mouth over the hard piece of flesh. He squeaked and involuntarily bucked his hips up. “You’re really good at that.” Dean shrugged, his mouth still full of cock. His eyes sparkled mischievously, however, and Sam dug his nails into Dean’s shoulders. “You’re a deviant.”
Dean winked and bobbed his head. His tongue played with the head of Sam’s cock and his nail scratched the sensitive vein. He’d figured out all the spots on Sam’s dick that made him squeal like a pig. “Imagine if Dad were here, seeing how much you like your big brother sucking your cock.”
“Jerk.”
“Bitch.”
Sam grabbed the lube from their nightstand. “Get the show on the road, Dean.”
“Okay, baby boy, you needy little bitch.” Dean uncapped the lube and drizzled some on his fingers. He opened Sam up quickly and then slid his cock inside his baby brother’s tight ass. They fucked roughly, like their sex always was. Sam made desperate little noises in his throat and Dean’s hands wound in his skirt. “Dressed up like a girl, damn Sammy, that was really hot. I didn’t even know that was a kink.”
“I didn’t know either,” Sam admitted. “But I accidentally grabbed the wrong pair and it was the most comfortable pair of underwear I’d ever worn.”
Dean kissed the column of Sam’s throat. “We should probably indulge in this kink a little more often. There’re a couple other things I could purchase for you. You ever heard of a garter belt?”