In my future speculative headcannon: Cressida, Mor, and Emerie enjoy a long and indulgent Away to Day. I imagine they're listening to poetry in incense rich tea houses on floor pillows, taking sulfur baths on the desert plateaus, enjoying clove oil massages, sipping mead, eating dates, and getting glyph blessings painted on their skin in gold. I think the trio would be a hit there.🌴🌅
A/N: This story includes mentions and descriptions of what I think the gang would look like and behave if they were drag queens. I love going to and watching drag shows both on TV and in person. I am also a member of the LGBTQA+ community myself and I mean zero hate or disrespect with writing this fic. I have the utmost respect for the performers and their craft. The names that I have chosen for the performers are based off their character in Supernatural. If these are the names of real drag queens, this is purely coincidence.
You knew tonight was going to be busy, but you were not prepared for the mass of customers waiting outside the club. It was the first Saturday of the month and that meant that it was drag night at The Bunker. The Bunker was a little bit of everything: a strip club, a bar, and for one Saturday a month a drag show. The club was a safe haven for the local LGBTQA+ community in Kansas as well as everyone else that walked through the door.
The drag show started at 10:30 and the clock in the dressing room read only 8:45. You had another dance to do in five minutes, so you touched up your makeup and made sure your outfit was in place.
You made your way onto the stage as the first few beats of your song pumped through the speakers. You began your sensual movements around the pole as you took in the customers around you. There were lots of new faces among some of your regular patrons. You smiled at Gordon as he made his way to the front row of the stage and placed his money down. You took off your crop top to reveal your bikini top that covered just enough to keep the people interested.
“Good evening, Mr. Walker,” you purred as you got down on your knees in front of him on the stage and guided your hands across your chest. You smirked at the growl that rumbled from his chest over the music. You learned long ago what he liked and you were more than willing to use that information to help pad your bank account.
You turned around and put your elbows down and began to shake your ass to the beat as you felt the familiar sensation of money being tucked into your bikini bottoms. You flipped your hair as you glanced over your shoulder at the older man with lust in his eyes. You thanked him as he stood up and walked back to his table. You giggled to yourself as you eyed the bulge in his jeans.
“You’re looking extra beautiful tonight,” a familiar voice drawled from the other side of the stage.
You crawled over to the familiar mullet-clad man as you positioned your tits close to him. Ash added to the cash in your bottoms and you took off your top as a thank you. He loved your tits and you squeezed them together in appreciation. He stayed for the remainder of your song and you left the stage with your discarded clothing and went back to the dressing room.
As you entered the three main performers were already busy doing their makeup, but welcomed you as you entered.
“Girls, the party can begin because Y/N has arrived,” Sam announced as he stood up to give you a hug.
“Please, everyone here knows that y'all are the reason this place is packed tonight and every first Saturday. The Bunker belongs to you,” you quipped as you began to change your outfit.
“I'm so sorry I'm late. Traffic was insane and they almost didn't let me in!” A new face complained as he made his way in.
“Be grateful you have a baby face, hunny. It has to be better than asked if you are an AARP member everywhere you go,” Dean retorted. “Jack, darling, this is Y/N, she-”
“Oh my god, you look amazing. Did you get your tits and ass done? They look so real!” he exclaimed as he saw you changing. You blushed and were cut off by Castiel before you could even respond yourself.
“Okay, number one: you never, ever ask someone that to their face, especially when you first meet them; number two, Y/N is 100% woman. She works here. She’s cool, but you need to play nice, hunny,” he warned.
“It’s okay. It’s not every day that I get compliments on my tits and ass from a guy that doesn’t want to fuck me,” you giggled as you held out your hand to Jack. “It’s very nice to meet you.”
“It’s so nice to meet you, too,” he gushed, “I’m so sorry about that.”
“Don’t worry about it,” you replied as you waved him off and finished getting ready.
It was unlikely that you would have to dance for the rest of the night, but you ensured that you were ready in case someone asked for a private dance. The chances of that were slim with the show that would be going on, but the staff wanted everyone ready just in case. When you were finished, you sat down and watched them get ready and enjoyed listening to their chatter.
Sam, Dean, and Castiel were hot as fuck out of drag and even hotter in it. Castiel was an old-school queen. He always looked beautiful in the elaborate gowns that were encrusted with jewels that he made himself. His makeup was always perfect and flawless. His aesthetic usually favored blues and silvers. When Castiel turned into his stage persona, Alotta Grace, you couldn’t help but believe that the name chose him. Dean’s persona, Cherry Galore, was a campy queen with exaggerated features and always quick with an insult and a come back that made the audience erupt with laughter. Sam made a drag style all his own. His persona, Ann T. Christ, was bubbly, sweet, and just a little sassy. Jack’s style for his persona, Cinnamon Rollz, was what he described as Vivian Ward from Pretty Woman meets Goodwill. What that was supposed to mean, you would have to wait for his finished look to see.
“Is Balthie going to be here tonight?” you asked after a lull in the conversation.
Dean rolled his eyes, “No, sweetie. He’s currently,” he looked at his wrist for emphasis,” either fucking the new guy he is with this week or sleeping because they’re done already.”
“You’re such a shady bitch,” Cas griped as he slapped Dean’s arm playfully. Dean just rolled his eyes as the group finished getting ready. You were about to follow them out and wait in the audience to watch their performance when Ellen, the house mom, stopped you.
“Hey Y/N, you have a private dance waiting for you in room 2,” she informed you as she gave you a once over, “and if I were you, I’d put on your slutty schoolgirl outfit.” You rolled your eyes as you headed back into the room to change, knowing exactly who asked for you.
“There’s my sexy little kitten,” Crowley groaned as you entered the private room. Crowley was nice when he got what he wanted, but he wanted what you would never give him. He always tipped extremely well when you played that part that he was after. You had turned down his offer to be his sugar baby more than once. He was handsome and older with an accent that always made you a little weak in the knees, but you couldn’t imagine living your life at the hands of another person.
“Good evening, Professor Crowley,” you purred as you moved to stand in front of him. You played your part as a shy and coy girl as you twisted one of your pigtails around your finger and stared at the ground.
“Are you behaving yourself tonight?”
You looked up slowly and bit your lip before answering and moving slowly towards him. “I’m always a good girl when you’re around, Professor.”
“Show me how good you can be, kitten,” he begged. You obliged as you straddled his lap, your knees on either side of his thighs. You smirked as you felt his hardness through his pants and your covered core as you began to grind yourself to the music. Tonight had been a slow night, even with two of your regulars tipping you as they usually did, so you started to push all the right buttons to get what you could from the man you were dancing for.
“Professor,” you started as you placed your hands on his chest, “I was wanting to be a little bad and wondered if you’d help me out.”
“What did you have in mind, kitten?” he moaned.
You silently grabbed his hands and moved them to onto your ass. His eyes went wide at your actions. “Oh, you are a naughty girl tonight. I thought we weren’t allowed to touch?” he tsked.
You leaned in and whispered, “Just consider this me trying to get extra,” you ground yourself down hard on his cock at the word, “credit. I might need to get a spanking, too, Professor.”
“Oh, is that so?” he asked with a cocked eyebrow. You winked as you maneuvered yourself across his lap and wiggled your ass.
You could sense his hesitation as he slowly slid his hand over your ass, so you encouraged him, “Please punish me, Professor Crowley. Please, I need you to spank me.”
The first impact of his hand on your ass made you jump as you moaned in pleasure. The second and third made the wetness in your panties grow as you let your wanton whimpers flow freely.
“Such a dirty girl you are,” Crowley praised. He slowly snaked his fingers into your hair as he leaned in to whisper in your ear, “I bet I know what else you like. May I?” he asked as his grip tightened slightly. He took your needy whimper as a yes and yanked you back by your hair as he smacked your ass a little harder. You wiggled your cunt against him trying to gain some friction. A brief thought that this might go too far was pushed out of the way as sat you up facing away from him. Your ass was still on his hard cock, his hand still gripping your hair as he moved his other hand to your white button up top, tied in a knot.
“I think we should remove this, don’t you?” he asked and you could only nod in response. His expert fingers quickly undid the knot and exposed your tits to him.
“Oh you naughty, naughty kitten. You didn’t wear a bra?” he questioned.
“They told me you asked for me and I wanted to be extra good for you, Professor,” you managed to reply.
He placed his hand on your thigh as he asked, “How good do you want to be for me kitten?” You knew what he was asking. You were needy and high on his touch. You considered his proposition before coming up with your own.
“As much as I’d love to feel your thick cock deep inside my tight little pussy, Professor, you know we can’t do that. You’re my favorite and you’re the only one that I’ve ever let touch me.” He pulled his hand away slowly, defeated. You grabbed it as you turned as much as you could with his hand in your hair to look at him, “But I think I have an idea that you might like.”
“I’m listening.”
You tapped his arms and he let go of you. You got down on your knees in front of him and began to undo his belt. His eyebrow shot up again, but you giggled as you explained, “I can’t touch you and you can’t touch me, but we could touch ourselves.” His belt was undone and you slowly unzipped his zipper. You stood up and fully removed your top and bent over at the waist as you took off your plaid skirt. You turned around to find himself palming himself through his underwear at the sight of you. A neon pink pair of lace panties, white stocking, and heels were all the adorned your body.
You sat down on the other end of the couch and spread your legs. He moaned even though he couldn’t see anything. He had wanted this, or as close to what you were giving him, since the moment he saw you dancing months ago. You smiled as you squeezed your tits together and moved on to roll your hardening nipples between your thumb and index finger. You moaned at the sensation. You looked up to see Crowley’s lust blown eyes focus on you.
“May I please see your cock, Professor?” you asked as you trailed one hand down to your covered core.
“I thought you’d never ask, kitten,” he smirked as he freed himself from the confines of his underwear.
Your own eyes went wide and you gasped at the sight of him. You could feel that he was well endowed when you sat on his lap, but you never would have guessed that he was this huge. He was long and thick and you wanted to take on the challenge that his package would entail.
You began to rub your clit through your panties at the sight before you as he began to pleasure himself. You were enthralled watching him work his length in one hand and cradling his balls in the other. You slid your hand inside your panties as your excitement grew. Your back arched as you felt your orgasm near.
“That's it, kitten. I want to see your face as you cum for me,” he growled as he stroked himself faster.
Your body tensed as you circled your clit faster and squeezed your nipple harder. Crowley's moans quickened as he watched you edge closer to your release. When you finally came undone, you had to bite your lip to stifle the scream that tried to tear through you.
As you came down from your high, you could tell Crowley was doing everything he could to hold back. You dipped two fingers into your soaked hole to coat them in your juice and leaned over to him.
“Would you like to taste how sweet I am, Professor?”
His groan was your answer as you slipped your fingers into his open mouth. He moaned around your fingers and it sent a shock to your core. He pulled back and asked you to go on your knees.
You pushed your tits together as he stood up, towering above you. “Are you going to cover my tits with your cum, Professor Crowley? Hm? I want to see you cum for me, please?” You begged as you stared up at him.
“Bloody hell. Fuck kitten, fuck,” he growled as he began to spurt hot, white ropes onto your chest. You moaned at the sensation of his cum cascading onto your skin. Once he was finished, he fell back onto the couch with a huff.
“Bloody hell, kitten. You're going to kill me or make my sell my soul to keep you around,” he chuckled as he grabbed a towel to clean himself up before handing it to you.
You cleaned up and got dressed. Thoughts of shame, regret, and embarrassment began to seep into as you stood in front of Crowley.
“I should apologize for-” you began as Crowley cut you off.
“Darling, you have absolutely nothing to apologize for. I understand if this is a once-in-a-lifetime opportunity for me. I will accept it and cherish the memory of this until I die,” he chuckled. He reached into his coat pocket and pulled out a plain, white envelope. “I hope this will suffice, love. Thank you again.” He handed you the envelope as he left the room.
You quickly opened the envelope and saw enough money to cover your rent for the next few months and then some. You’d count it later, but now you wanted to see how the drag show was going on. As you made your way to the dressing room to put your money away, you saw Cinnamon Rollz performing to Joan Jett’s Do You Wanna Touch Me. She was killing it a leather bodysuit and studded bra. You smiled watching her enthralled in her performance. Once you were in the dressing room, you put away your money from your dance.
“Looks like someone was a busy bee,” Ann called from the other side of the room. Your cheeks warmed at the realization of what she saw.
“He has a thing for the whole school girl look,” you chuckled as you began to change. “Have you already performed tonight?”
She nodded as she sat down. “You were in there for a while. All tea, no shade. A girl’s gotta do what a girl’s gotta do to pay the bills. You do you, honey. Lord knows I’ve been to hell and back for a Benjamin,” she chuckled.
Once you were changed, you gave Ann a kiss and walked back as Shania Twain’s Man I Feel Like A Woman started to blast through the speakers. Cherry Galore appeared on stage and your eyes were glued to her the entire time. You chuckled out loud each time she said: “Man, I feel like a woman” in her regular, deep manly voice. She was working the crowd and making lots of well-deserved tips. You joined in and cheered her on.
Alotta Grace was up next and she didn’t disappoint. Then again, she never did. In her usual style, she performed to a classic song Fever by Peggy Lee. Her gown was as elegant as ever, adorned in silvers and blues, She met your gaze in the crowd and gave you a knowing wink.
By the time the show was over, the club was working on shutting down and calling last call. You were in the dressing room changing into normal street clothes with the other performers.
“Ya know, we do have an amateur night and we are inclusive. You are hot as women, and dare I say even hotter men,” you winked.
Sam and Jack just dismissed you, but Dean and Castiel were listening. “You two have killer bodies, amazing smiles, and obviously have the moves. Hell, I’m sure you could put me to shame.
“Well, a little birdy told us that you could buy us a boat, so I don’t think that’s true,” Cas whispered. You instantly shot Sam a death glare, knowing he was the only one that saw.
“I earned that money and none of my morals were corrupted, thank you,” you hissed.
“We aren’t judging you, Y/N. Do you want to come over to our place and hang out?” Dean asked.
“And you are under no obligation to wear that school girl costume,” Castiel added.
“I mean, unless you want to,” Dean added, which promptly caused Castiel to slap dean in the shoulder.
You rolled your eyes, but took them up on their offer.
***
Beer was flowing freely between the three of you and talks of everything from sex to politics had been discussed. You stood up to grab all of you another round when the alcohol really hit you.
“Fuck, I’m going to have to stop if I’m going to get home,” you complained. You nearly missed the look that Dean gave Cas as you made your way into the kitchen
“Or, you could spend the night here,” Cas offered.
You snorted. “Yeah, sure. I’m sure you’d love that. What, are we going to tell ghost stories and braid each other’s hair?”
“We could do that. Or, we could think of something more...exciting,” Dean offered.
When you made your way back to the living room, the confused expression on your face said more than you could eloquently communicate.
“We’re dating, but we are also bisexual. Both Dean and I find you extremely beautiful and we’ve actually talked about this before.”
“Wait, you guys talk about me?”
Dean held up a hand, “Only good stuff, though.”
You shrugged, “I’ll do it under one condition.”
“Name it,” they answered in unison.
“I want to watch you two together.”
***
Cas was laying on his back on the bed with Dean in between his legs sucking his thick cock while you were at the head of the bed rubbing your clit. You never expected to see this, but you were sure as hell glad you were.
Castiel’s moans sent jolts of excitement to your core every time Dean coaxed them from him. He caught your gaze. “Do you like watching Dean suck my cock?” he moaned. You could only nod in response. He chuckled, a slight darkness behind it.
“She likes watching your pretty lips wrapped around my fat cock, Dean.” Dean moaned around his thickness.
“Come here,” Cas moaned out. You complied and Cas positioned you over his face, facing Dean. Cas’ mouth was on your wet cunt in a second. The wave of pleasure his mouth brought you would have sent you falling forward if his arms weren’t wrapped around your hips holding you in place.
Cas’ lips vibrated around your clit as he moaned as Dean continued to work his cock in his mouth. You looked up to see Dean’s emerald eyes trained on you. He was stroking his own cock as he watched his boyfriend pleasure you with expert tongue. When two of Castiel ’s fingers plunged into your hole, you came undone. Waves of pleasure ran throughout your body and your moans of ecstasy filled the room. Your eyes were locked onto Dean as you came down from your high, but you still needed more.
“Please. Please, someone, fuck me,” you begged. Dean stopped sucking Cas’ cock with a pop as he released it from his mouth as he flipped you onto your back. He grabbed a condom from the bedside drawer and quickly placed it onto his hardened cock. He slid into your tight pussy with one push. He filled you completely and you enjoyed the stretch. Your whimper of desperation sunk in and Dean slowly pulled out and slammed back into you.
You wrapped your legs around Dean and placed your ankles on his ass to pull him closer. Your moans filled the air as you felt another orgasm building inside you.
“Dean, stop,” Cas commanded. You whined when Dean obeyed and stopped moving. You hear the click of a bottle opening and knew Cas was lubing up his cock and Dean’s hole. You mewled when Dean jerked inside you at the cold liquid applied to his hole.
You were able to look over Dean’s shoulder to see Cas lubing up his cock. You bit your lip as he lined himself up with Dean’s waiting hole. Cerulean eyes found yours and Cas smirked as you watched him slowly sink his thick cock into his boyfriend’s tight ass. Dean was cursing in your ear as he let himself become re-accustomed to Cas’ thickness.
Once Dean was ready, Cas began to thrust into him letting him feel the full length of himself before slamming back in. Dean’s face contorted into pleasure and you squeezed yourself around him.
“As hot as this is to watch, do you think you could-” you began to ask Dean.
“Of course, darlin’,” he drawled as he began to move. Dean and Cas worked in perfect unison. You continued to squeeze your cunt around Dean as another orgasm began to build inside you.
“Not gonna last long if you keep that up,” Dean moaned at the sensation.
“Me either,” Cas added.
“Then cum for me,” you begged the couple. Their pace quickened and faltered as the orgasms of the three of you came closer. You were the first one to let go, your cunt spasming around Dean. Your orgasm spurred on Dean’s as he filled the condom with his hot cum. Cas followed quickly behind his boyfriend as he filled his hot ass. The two men fell onto the bed on either side of you. You let them snuggle into you as your breathing returned to normal.
“That was hot as fuck,” you finally managed.
“If you think that’s hot, just wait until you see Dean make us breakfast in the morning,” Cas teased as he placed a kiss to your cheek.
Thorin Oakenshield : Daughter of Thrain Son of Thror, Queen Under the Mountain, Sister of Frerin and Dis, Aunt of Fili and Kili, the Queen Without a Mountain
"I would take each and every one of these dwarves over an army from the Iron Hills, for when I called upon them, they answered. Loyalty, honor, a willing heart. I can ask no more than that."
