Disclaimer: I own nothing but a warped imagination and a weird sense of humour.
A/N: Well it's been a while... In short I've got a new job and the hours are kicking my arse. 8am starts don't agree with me. Anyhoo, this is a long one.
List Item: Dress up as a woman
Summary: "This is like a torture device." He stated, reaching down the back of the skirt and prising the material from between his cheeks. He decided thongs could not be classed as underwear. Underwear was supposed to cover your butt, not try to cut it in half.
Next: Hug a Hybrid Day
A month after the Stefan incident, Damon had decided it was time for him to choose another item on his list. He'd looked over and noticed the last one – Let Stefan be in charge. He knew there would be a world of pain attached after what he'd subject his brother too, so in order to take the heat off himself, he decided to allow Stefan to select from the other items on his list and set the terms required for it.
"So I get to pick any one I want and name the terms?" Stefan inquired, glancing up and down the list. "I notice you've removed the one for me being in charge."
"What can I say brother, I'm saving the best till last." Damon smirked smugly as Stefan cast him a knowing glance.
"Fine," Stefan dragged his eyes over the list, pondering the terms he could set for each of them, but only one stood out. "Dress up as a woman."
Damon groaned. "I should have known you'd choose that one but fine, name the terms."
"Forever?" Stefan asked, a lost hopefulness in his voice.
"Ha. Ha. Nice try."
There was quite a debate about the length of time Damon should be dressed up for. Stefan finally decided on 10 years and a bidding war began – Stefan lowering his terms from 10 years and Damon refusing to budge from one day.
"Two weeks?" Stefan was getting annoyed. The discussion had gone on for longer than he would have liked. Obviously when Damon told him he could set the terms, that hadn't been exactly true. Sure he could set them, but only if Damon was okay with it.
"That's a week too many, one day."
"You're going to live forever, two weeks is hardly anything."
"A reputation can take a second to destroy and a lifetime to rebuild."
"Fine, one week then, that's as low as I'm going." Stefan stated, sitting back and folding his arms tightly across his chest. He wasn't budging. A week was barely anything.
Damon thought for a moment before nodding. "Fine, I can deal with that."
Stefan removed his phone from his pocket as Damon eyed him suspiciously. "I don't know about you, but I'm not an expert in dressing like a woman, we're going to need reinforcements." Damon furrowed his brows. "I'm calling Elena."
"Ha, well I would have settled for two weeks – too late now, loser." Damon stated childishly before poking his tongue out at his brother. Stefan didn't seem fazed by it, just rolled his eyes and pressed the call button.
Two hours later there was a knock at the door. Stefan answered, grinning smugly to himself at the sight before him. Elena had brought a friend.
"What's blondie doing here?" Damon questioned from where he was slouched on the sofa.
"We were shopping when Stefan called, so we got a few things for you." Caroline stated as she and Elena held up the variety of bags.
Damon eyed the many bags they were holding. "What the hell did you buy, the contents of an entire store?"
"A week worth of female clothes and accessories, actually." Elena stated, placing them on the floor as Caroline did the same. The word 'accessories' made Damon shudder.
"You were so hard to buy for, we didn't know what sizes to get so some of these may be a little tight." The blonde furrowed her brows before reaching into one of the bags before pulling out what at first looked to Damon like a piece of cloth.
"I'm not wearing that!" he exclaimed, pointing towards the thong.
"You have to, you said I could set the terms, those are part of the terms." Stefan stated smugly. He finally had Damon right where he wanted him. He was going to make his brother pay for that one day with a week worth of humiliation.
"Time lengths were agreed, not clothing items." Damon stated in a matter-of-fact tone, scrunching his nose up at the offensive item.
"I went easy on you on the time length, you had a bit of leeway there and that's all you're getting. You're going to wear it."
Damon scowled at his brother and the two females before him. They all focused their stern gazes on him, causing him to sigh. "Fine, whatever. I'm comfortable with my sexuality."
Stefan smirked, eyeing his brother curiously. "No one said you weren't."
"Shut up Stefan."
The process of getting Damon dressed took way longer than it should have. Caroline and Elena were nice enough to sort the clothing into neatly folded piles, a different outfit for each of the days and some extras in case Damon decided he wanted to dress up a bit more. Most of the items were dresses and skirts. There had been a single pair of jeans, but they'd turned out to be way too tight.
"You can see everything, he can't wear those." Elena stated, placing her hand out in front of her to block out the visible outline of Damon's manhood through the dark tight denim.
Caroline cocked her head to the side. "It's only a bit, people might think it's just a bunched up piece of denim."
"Do you mind not checking out my junk." Damon cocked an eyebrow at the blonde.
Caroline's mouth snapped open before she glared. "I'd rather gouge my eyes out."
After a few more minutes of discussion it was decided, much to Damon's dismay, that the jeans were too tight and that the skirts and dresses were going to be the only appropriate items. He had tried to fight his corner, but when after Elena told him the only way he'd get away with them was by either cutting it off he'd quickly backed down.
Soon Damon was dressed in a red padded bra and matching thong, a red vest top, a black knee length skirt, tights and black heels.
"This is like a torture device." He stated, reaching down the back of the skirt and prising the red material from between his cheeks. He decided thongs could not be classed as underwear. Underwear was supposed to cover your butt, not try to cut it in half. No one seemed to be listening though. Stefan was absorbed in some book and the girls were inspecting his appearance so far and muttering amongst themselves.
"We can see his leg hair and it's sticking out the material…we need to wax his legs." Caroline said casually to Elena who started nodding in agreement.
Damon looked down, noticing the pantyhoes did look rather furry, but he shook his head. "No way blondie, not happening." He would agree to wearing the clothes and the underwear, but stripping him of his leg hair was a step he wasn't willing to take.
"Well we need the tights then." Elena reached into the bag, pulling out the packet of tights they'd purchased. "I'm glad we thought of everything."
"Aren't you two just peaches?" Damon snorted sarcastically.
The tights were a little too small, but it didn't matter. Damon's package couldn't be seen beneath the skirt but it did take a hell of a long time to get them on. At first Damon had insisted on putting them on himself.
"I'm a big boy, I can dress myself."
"Fine, knock yourself out." Caroline threw the tights at him. He held them by the waistband, unsure of which way they were supposed to go.
"The coloured stitching goes at the back." Elena stated as Caroline huffed from beside her and muttered something about letting him figure it out himself if he thinks he's so smart.
Damon placed the tights over his feet, yanking them with so much force that the rather sturdy material ripped apart entirely.
"Oh yeah, you can clearly dress yourself." Caroline mocked, rolling her eyes at his stubbornness as he threw the destroyed tights to the side.
"Can we please just help?" Elena asked sweetly, batting her eyelids as Stefan snort-laughed from the sofa.
Damon narrowed his eyes, taking in her pleading smile before sighing. "Fine, but don't get fresh."
The girls each took a leg and eased the new pair of tights up, making sure they were stretched as far as they could. When they reached the top of his thighs they allowed Damon to take over, reminding him to be careful not to rip the material again. After all, he was going to need to adjust to make everything as comfortable as possible.
"Stefan?" Stefan raised his eyes from his book to look at his brother. "Do these tights make me slimmer?" he questioned coyly, standing on the side and placing his hand on his abdomen. Stefan rolled his eyes and stood up, retreating to the kitchen.
Caroline and Elena dived into another bag, pulling out a variety of different makeup supplies. Damon was getting annoyed. The tights had been fine at first, but now they were starting to feel uncomfortable, pinching around his balls and digging in at his hips. He pulled at the waistband, shoving his hand down in an attempt to manoeuvre things around.
"Stop adjusting, it's not lady like." Caroline snapped, fixing him with a glare.
He scrunched up his face, ignoring her demands and continuing to sort himself out. "I'd like to see you wearing tights with balls, there's not much room."
"What's going on?" Stefan questioned, slumping back down on the sofa again.
"Damon's complaining about lack of ball room." Caroline huffed, placing a hand on her hip and pointing in Damon's direction. Stefan looked at his brother as his face contorted with each hand movement.
After around a minute Damon finally stopped adjusting himself after Stefan accused him of playing with himself in the living room in front of guests. Damon had huffed and removed his hands, casting a glare in his brothers direction.
Then it was time for makeup. Caroline squealed in delight at the discovery that they'd gotten a foundation that matched Damon's skin tone perfectly. As he looked in the mirror he had to admit the foundation did look pretty good. His skin was flawless to being with but the makeup made it look even better.
After foundation they applied blusher and eye shadow, when it came to eyeliner, things went a little awry.
"Will you just hold still." Caroline snapped trying to hold onto him as Damon leaned his head away from the pencil, his eyes blinking furiously.
He pulled his head from Caroline's grasp and moved back out of reach. "And let you poke my eye out? Not a chance, give it here." He snapped back, holding out his hand expectantly.
"Fine." Caroline huffed and slammed the eyeliner into his hand, almost snapping it before slumping down on the sofa beside Stefan, arms folded tightly across her chest.
Damon's mouth dropped open as he brought the pencil towards his eye. He placed it carefully and started moving slowly, "Ow!" he shouted, dropping the eyeliner as he blinked furiously. "How the hell do you do this?" He picked up the offending item, "It's got a point! An actual point!"
"Yeah, pencils usually do have points…" Stefan stated slowly before smirking over at an annoyed looking Damon.
"It serves you right." Caroline stated, childishly poking her tongue out at the older Salvatore.
Elena rolled her eyes and knelt down in front of Damon. "Here, I'll do it." Damon eyed her open hand cautiously. "Would I poke you in the eye?" She quirked an eyebrow as Damon pondered that thought. He was pretty sure she wouldn't do it intentionally, but it could happen by accident. However, she was a girl, she probably had a steadier hand than he did.
"Why don't we just line his eyes with that really dark eye shadow?" Caroline suggested, noticing that Damon still hadn't handed the eyeliner over and didn't appear to be considering it any time soon.
"Yeah, good idea." Elena picked up the pot filled with dark dust, loading up a thin brush before taping off the excess.
Damon blinked rapidly as the brush ticked his eyes, water building up and almost running down his face. The eye make-up took a lot longer than it should have. Damon's eyes kept watering every few seconds, sending black tears streaming down his cheeks. The wig had come next. Caroline and Elena had chosen a black wig, but of course Damon complained saying he wanted to be a blonde "Blondes are said to have more fun," he complained, scowling at his appearance in the mirror.
Damon was stood in the middle of the living room doing various poses when the doorbell rang. Damon and the girls didn't seem to hear, in fact they'd been so preoccupied with Damon's new image that no one had noticed when Stefan snapped a few pictures of his brother in various poses. He had a feeling he was going to need them as ammunition later on. Stefan sighed, placed the book he was reading on the sofa and got up to answer the door. When he opened it, he couldn't believe his luck.
"To what do we owe this pleasure?" he questioned, smirking at the three men stood outside.
"A little bird told us something rather interesting was going on at the Salvatore residence, we felt we needed to come and see exactly what it was." Klaus smirked, attempting to peer into the house behind Stefan.
"By all means, come in." Stefan smirked to himself and stepped to the side allowing Klaus, Kol and Elijah to enter. Once they were in Stefan shut the door, surprised that they hadn't moved from the hallway. Under normal circumstances he'd have kicked them out, but making Damon suffer was his top priority.
"My, that is a most unfortunate looking woman." Elijah commented, glancing over to where Damon was stood posing in the centre of the living room.
"That's no woman brother." Klaus stated, looking mildly horrified at the sight that was in front of him.
Kol looked up to see what they were talking about, a mocking smirk appearing on his face as he took a few more steps forward "Damon Salvatore?" his mocking tone filled the air followed by hysterical laughter. Damon's head shot in the direction of the hallway, his mouth dropping open in surprise. "This is the best," Kol commented, removing his phone from his pocket and snapping a picture. Within a spit second Damon appeared in front of him, going to snatch the phone as Kol dodged it, reappearing over the other side of the room and shoving his phone back in his pocket.
"You know, I think I'll call you Delilah." Kol grinned smugly, folding his arms across his chest and giving a satisfying nod.
"I think you actually looked more feminine before." Klaus commented, his expression somewhere between amusement and disgust as he observed what Damon was wearing.
"Hey there Delilah, what's it like in New York city?" Kol sang dramatically from the doorway.
"Go get daggered." Damon sneered, not bothering to hide his dislike for the youngest male original.
"Now Delilah, that's not very lady-like." Kol tutted mockingly as Caroline and Elena came from the living room, announcing that they were going to the Grill – they also included Damon. While getting ready Stefan had set out a few more terms of the week. Damon wasn't allowed to hide at home, he had to venture out in public and remain out until Stefan decided he could return home. No Vampire powers allowed at all. Damon has to play up to the part at all, times, acting like a girl as opposed to a guy dressed in drag.
"Here." Caroline stated, handing Damon a black purse.
"You're seriously expecting me to walk around with this?" he questioned, dangling the purse off his finger like it was diseased.
She quirked an eyebrow as she looked him up and down. "You're wearing a thong, a skirt, tights, a halter…so yes."
He groaned, ignoring the snorts that came from Klaus and Kol at the mention of a thong. Elijah just stood looking rather disturbed, his eyes casting over Damon's appearance before he shook his head. Caroline was right. He'd already gone all out on the outfit, a purse wasn't going to make much difference. "Fine." He opened the purse and threw his phone inside before swinging it over his shoulder, hitting Kol in the face.
"Watch it." Kol glared, muttering something under his breath that Damon didn't quite catch.
"What you gonna do, hit a lady?"
"I see no lady, just a tramp." Klaus
As Damon headed out the door, Kol scrunched up his nose. "Are you really wearing a thong?"
"Shut up small fry." With that Damon strutted out the house.
"Right, that's our cue to leave, so out." Stefan waved his hands, ushering the originals, Caroline and Elena from the house. Elena said bye to Caroline before she and Stefan scurried off after Damon.
It turned out he hadn't made it far. They caught up with him not so far ahead, bent over and trying to prise a heeled shoe from out of the grass.
"How the hell is anyone supposed to walk in these damn things?!" he huffed, pulling the shoe from the grass before removing the other one.
"Heel's aren't made for walking on grass." Elena stated, dragging Damon off the grass and onto the concrete.
Damon huffed again and dropped the heels onto the floor before putting them back on. Stefan and Elena stifled chuckles as they followed behind a stumbling Damon. Every now and then he would fall off the heels or they'd get caught in a crack on the pavement, sending him flying forward onto the floor whilst his shoe remained stubbornly wedged into the crack.
When they arrived at the grill Damon sauntered up to the bar and Stefan and Elena noticed that people were casting strange looks in the direction of the stumbling large 'woman'. He ordered his drink before sitting down on one of the barstools. Stefan and Elena cast each other knowing looks before joining him.
Over an hour later and Stefan and Elena were bored. There was a lack of conversation and Damon just seemed to be quite happily drinking himself far away from sobriety.
"Can we go now? How do you expect to walk home drunk when you can't even walk sober." Elena nearly whined, resting her chin on her palm.
"They're not glued to my feet, I'll just take them off." He shrugged. Stefan noticed the barman looking in their direction his brows furrowed as he listened in on their conversation.
"Make your voice a bit more feminine."
"Why? I could be a 60 a day smoker making me a husky voiced female." Damon wiggled his eyebrows and Stefan rolled his eyes.
"Nice try, but no. Sound more feminine or there's going to be an eternity of torture attached."
Damon glared at Stefan but his brother refused to budge. "Fine." He practically growled.
"I'm sorry, what was that?" Stefan glared.
Damon cleared his throat, gritting his teeth before letting out a rather high-pitched "Fine."
"Much better." Stefan smiled smugly before taking a sip of his drink. "Your glass is looking kind of empty there sister, you better order another one."
Damon's nostrils flared and he ground his teeth together before turning to the barman. Stefan watched in satisfaction as Damon called the barman over before ordering his drink in a ridiculously high-pitched voice. The barman cast him a suspicious look before quickly fixing his drink and hurrying off down the other end of the bar to dry some already dry glasses.
Stefan watched as his brother sipped his drink. He needed to think of something, a way to truly get Damon back for the day of hell he'd put him through. It had taken Stefan two weeks to finally get his room back to normal. The flour and gunge had clung to everything and got into every tiny little space. The worst damage had been done to his bookshelf, all the pages of his books were still tinged pink around the edges.
He tipped back his glass and downed his drink. He needed to go back home and gather his thoughts. He needed to plan. He needed to make his brother stuffer.
"I've got to go." Stefan said, casting Elena a look as she nodded in understanding.
"Why? Need to think hard about how to make my week even remotely as bad as your day." He smirked, taking a drink. "I can hear the cogs working full speed already."
Stefan rolled his eyes and kissed Elena before leaving without another word.
Elena watched him leave before turning to Damon, her arms folded on the bars surface. "So how long are you planning on staying here?"
"Until I forget that I'm dressed as a woman." Damon smirked as Elena sighed in annoyance. She was going to be in for a long night.
Around three hours later Damon finally decided he was ready to leave. He hopped down from the stool, almost toppling over on his heels but being caught by Elena who's hand landed on his chest padding
"Hey, no gropey unless you're willing to let me do the same." He made to grab Elena's chest, a smirk on his face. She groaned, removed her hands from him and let him fall to the floor.
"Stop being a jerk Delilah." She folded her arms across her chest and quirked an eyebrow as Damon pouted up at her from the floor before clumsily getting up. Elena was sure he'd flashed his tight covered ass to the people behind him as they grimaced. Damon flattened his clothes down before picking up his bag and storming unsteadily from the Grill. Elena watched him leave before taking a deep breath and following behind.
She'd just stepped outside to see Damon stood on the sidewalk, glaring to the other side of the road where a drunk man was hollering and wolf whistling.
"Men are such pigs." He Damon commented, swinging his purse over his shoulder and scoffing in the direction of the drunken man.
Elena snorted as she followed him "Men are such pigs." She mocked. "Are you serious? You've been dressed as a woman for less than a day and you're already talking like one."
"Just playing the part Elena, now hurry up. My feet are killing me."
After making sure Elena got home Damon hobbled off. When she'd suggested him walking her he was going to make the argument that he was no longer a man and it wasn't considered necessary for him to escort her home, however he couldn't help but feel that would be taking the dressing as a female just a little too far.
He walked through the door and kicked off his shoes, sighing in relief and wiggling his toes. He reached into his top, unclipping the bra and letting it drop to the floor. Girl clothes were the most uncomfortable things in the world.
"Stripping in the doorway, not very ladylike."
"Bite me." Damon growled, heading off upstairs and discarding each item of clothing along the way. Stefan chose not to follow, his brothers thong covered butt wasn't something he wanted to see.
The second day of Damon's transformation was nowhere near as fun as Stefan had hoped. Damon chose to stay in his room, claiming not to be ready to get up. At around noon Stefan had had enough. He marched into the room and forced Damon out of bed before ordering him to get dressed and come downstairs.
Around an hour later Damon came downstairs looking like a kid had used his face as a canvas to play with Crayola. His eyes and the surrounding area were covered in electric blue eye shadow. His eyeliner was about 4 mm from where it was supposed to be and there was mascara dotting his eyelids and the underneath of his eyes.
His cheeks were covered in a blush that was just too red, his lips half covered in pink lipstick and his foundation blotchy from lack of blending.
"The circus isn't in town this week." Stefan commented as Damon slumped down onto the sofa opposite him. Damon ignored him. "You look like you got into a crash with a Crayola van."
"Well I'm sorry that unlike you, I'm not used to applying makeup." Damon quipped and Stefan rolled his eyes.
"You've been up there an hour and that's the best you could do?" Stefan scoffed, waving a hand in the direction of his brothers face. "I've seen corpses that look better."
"Well I'm not exactly alive, am I?"
"No, but unfortunately you're up walking about and talking."
Damon dramatically slapped his hand over his head. "You've wounded me bad Stefan."
"If only…"
"Give it up brother, there's no way you're going to get me as good as I got you."
"You're right," Damon looked shocked for a moment before casting Stefan a smug look. "I'm going to get you better." The smug look on Damon's face dropped as Stefan smirked.
"You wish." Damon scoffed before reaching up and grabbing a drink.
Stefan tried to get Damon to snap, he really did, but it was no use. Every single insulting thing he threw at him was brushed off as if he hadn't even heard it. On the odd occasion he threw some comment back, but the majority of the time he ignored it entirely, just giving the odd humming noise here and there to let Stefan know he'd heard.
After what felt like a lifetime of trying to get Damon to react, he gave up and admitted defeat, retreating to his room to make some calls and plan for the days ahead. His call with Elena hadn't been going great, the only suggestion she had was announcing in public that Damon was actually a man, but Stefan just knew that wouldn't bother Damon in the slightest. However, when Caroline turned up at Elena's, she unknowingly gave him an idea when she suggested to Elena that they go shopping.
The next day Stefan had decided to put his plan into action. He'd spent most of the night lying awake, thinking of other ways to get Damon back. His brother had pretty thick skin and no amount of insults was going to bother him. Stefan had to take physical action if he was going to get a reaction from his brother.
Damon was dressed and lounging around the house when Stefan came in with Elena and Caroline in tow.
Damon groaned and let his head roll back. "What now?"
"We're going shopping!"
"Why? I already have plenty of clothes."
"Because as a female most of us enjoy nothing more than a day of shopping. You're being a female for the week so you have to come."
"A day on my feet in heels? No chance." His feet still hadn't recovered from the day before and the bra was cutting into him like no body's business.
"You have to and we were nice enough to get you these." Caroline held up a pair of flat black shoes. "When your feet start to hurt you can just put these on."
Damon narrowed his eyes at the smiling blonde. "Fine, only if he's coming."
"Of course I'm coming. Do you really think I'd miss out on a day of torture for you?"
"You'll be shopping too."
"But I'll have you as entertainment."
Stefan grinned smugly as Damon huffed and lent forward, putting on his shoes before standing up, grabbing his jacket and purse and heading for the door. They all cast each other a look before Stefan smirked.
"Today's going to be a whole load of fun."
It turns out the day wasn't as fun as he'd imagined it would be. At first Damon whining about his sore feet and the bra and tights cutting off his circulation had amused Stefan, but after an hour he was considering running away and locking himself in a dark room.
"Can you just shut up for one minute." Stefan snapped, pressing the bridge of his nose.
"You try walking around in heels."
"You've got some flat shoes, just put them on." Stefan stated, signalling to Damon's overly stuffed bag. He couldn't help but wonder what Damon actually had in there.
"And miss annoying you, not a chance. The tables have turned."
"I hope your feet fall off."
"That's very immature of you Stefan." He stated before poking his tongue out at his brother.
When they went to the makeup shop, Damon decided to act like a child. He picked up various coloured lipsticks and eye shadows, smearing them all over his face before shouting across the store at Stefan. "Honey, what do you think of this colour for our anniversary night out."
The next shop they went into was a jewellery shop, Elena wanted a pair of earrings and Caroline just enjoyed looking at the sparkling expensive jewellery. Stefan noticed how Damon's complaining of sore feet had stopped entirely and he didn't seem to be struggling to walk anymore. He was certain his brother had only complained in the first place to piss him off. Stefan had been looking at a rather fancy ring when he heard loud talking coming from over at the counter. He looked up to see Damon pointing at various rings while the woman behind the counter quickly fished them out.
"Oh these are beautiful!" he cooed in an overly high pitched voice. "He'll say they're too expensive but I just know he'll get me one," he sighed before turning to look at Stefan and waving. The woman behind the counter's eyes followed Damon's line of sight.
"That's your boyfriend?" she asked, shock evident in her tone.
"Yeah, dreamy isn't he? Hey honey, I like all of these." He signalled to the rings on the counter. Stefan chuckled and shook his head before walking over to Elena who was admiring a pair of earrings.
"What do you think of these?" she said, holding them up to the light so the purple gems sparkled.
"They're nice, but on you they'll be beautiful." He near whispered before wrapping an arm around her waist.
"You pig!" Damon's shrill voice filled the air. "My sister? I see you're not even trying to hide it, how long's this been going on?"
Elena turned, brows furrowed and a look of confusion on her face. "Da—Delilah, what are you talking about?"
"How could you do this to me Esmeralda, we're sister and you know he's the love of my life." Damon stormed forward, slapping Stefan hard across the face. "I never want to see you again," he cast a look in Elena's direction. "Either of you." And with that he stormed from the shop, Caroline hurrying after him trying to stifle her giggles. Stefan and Elena looked at each other, then to the woman, then to the doorway Damon and Caroline had just went through.
"I can't believe you did that." Elena stated once they'd arrived back at the Salvatore residence. She felt humiliated. After Damon and Caroline had left herself and Stefan received disgusted looks, shakes of the head and tuts from the women behind the counter. Stefan had quickly removed his arm from around her waist before they sheepishly left the store, walking through a small crowd who had gathered at the sound of the commotion
"I didn't plan it, it's not my fault he can't keep his hands to himself in public. Besides, he knew I'd set him up as my boyfriend – he brought it on himself, and you for that matter." Elena pouted. "Really you should be angry at him, he caused it."
"Did he tell you to kick up a fuss? The women probably didn't even notice until you drew their attention to us."
"Of course they noticed, they were ogling him the second they saw him. This could have been all avoided if I hadn't been dressed as a woman. My dashing looks would have completely captured their attention."
"If you weren't such an ass you wouldn't be dressed as a woman in the first place." Stefan pointed out, placing his arm around Elena as she slumped down on the sofa.
"Whatever, the only reason any of you got a chance to suggest this was because I decided to write a new bucket list – it's not my fault you decided you wanted to torture me." Stefan furrowed his brows. "Basically, all of this is your fault and I accept no responsibility." Damon didn't wait for a reply, just headed off upstairs feeling rather pleased with himself.
"You have to get him back for this." Elena stated, turning to face Stefan.
"You think I haven't been trying?"
"You need to try harder." Elena urged, poking a finger at his chest for emphasis.
"There's nothing I can do, I've got so many things going through my head but I just know they're barely affect him. I'm not sure if you've noticed, but Damon isn't exactly normal."
"There's only one thing for it, you're going to have to think like him." Stefan frowned. "If you want to get even the smallest reaction, you're going to have to get into his frame of mind, think about what makes him tick."
Stefan pressed his fingers to the bridge of his nose. "I thought this was about torturing him, not me."
"No pain, no gain."
As much as Stefan didn't want to admit it, Elena was right. If he was going to get a satisfying reaction out of Damon, he was going to have to try to work his way into Damon's mind – a place he really didn't want to vist.
"Grill?" Damon didn't even bother saying morning to his brother as he swung his purse over his shoulder and paused briefly in the living room doorway.
Stefan suppressed his grin and nodded before following his brother out the house, chuckling inwardly at how oblivious Damon was. In his few days of being dressed as a woman, he'd picked up how to talk in heels surprisingly quickly, he'd also managed to apply his makeup without looking like a clown. Stefan was pretty sure he'd mucked it up a few days earlier on purpose.
"You go on ahead, I've got something to do first." Damon eyed his brother suspiciously.
"Ooo, secretive Stefan." He taunted, complete with jazz hands. Stefan rolled his eyes. "Whatever, it's not like you could do anything remotely humiliating." With that Damon left.
Stefan grinned to himself before walking over to the bookshelf, pulling out a stack of papers he'd hidden before Damon got up. He knew his plan would never humiliate Damon to the extent he wanted, but he was fairly certain he'd react to it. There was no way he could just ignore it.
Damon had been drinking alone for around an hour and a half when Stefan walked into the grill, a huge grin plastered across his face. "What's got you looking so smug?" he questioned as Stefan ordered himself a drink.
The bartender placed the drink down and the younger Salvatore took a sip, not meeting his brothers eyes as he grinned again. "All in good time."
A while later Damon was bored of drinking and Stefan was practically bouncing with anticipation. He couldn't wait for him to get outside and see exactly what he'd been planning since early morning. Damon got down off his stool and Stefan hung back slightly, following his brother to the exit and out the door.
Damon stepped out on the street, wondering exactly what Stefan was up to when chuckling met his ears. He turned to see his brother stifling his laughter. He quirked a brow before looking around, wondering what had made Stefan so amused. At first he didn't see anything, everything was perfectly normal. He reached up, ensuring his wig was still in place and then he noticed it. A piece of paper on the lamppost in front of him. He sighed and walked forward, having a fairly good idea what he was going to see on the poster. He was right.
"You've got to be kidding me?" he groaned, peering at the poster stuck to the lamppost. A laugh sounded from behind him and he quickly turned around to see his brother in hysterics. "Seriously Stefan, could you not think up something original? You just had to steal my idea."
"I had to put up with it, it's only right you have to do the same."
"The thing is, brother, I'm not bothered by this in the slightest. Every single guy that's called my phone has quickly hung up when a male voice answered. Your little plan's failed."
"You may not be bothered by that, but you will be bothered by this." Before Damon could blink Stefan dashed forward and grabbed hold of the pantyhoes and thong, pulling as hard as he could. The sound of tearing material filled the air followed what could only be described as the noise of a wounded animal.
Damon's face turned red as he fell to his knees, clutching his crotch. "Seriously, not cool. My balls…" He fell fully onto the pavement and adopted the foetal position. Stefan stepped back to watch the show as Damon groaned on the floor. The pantyhoes had ripped entirely at the back, Damon's snapped blue thong and one butt cheek on show.
Stefan quickly snapped a picture of his brother, forwarding it on to Kol before walking back home. He sat down on the sofa and waited, he knew Damon would soon be coming through the door like a tornado who's aim was just to destroy him.
It was quite some time later when Damon returned home – a grimace on his face and walking like John Wayne. He waddled his way into the living room, making to sit down on the sofa but changing his mind. He went to lay down face first, but again changed his mind.
"Would you just decide how you're going to sit already?" Damon was on his eighth position attempt and Stefan was growing increasingly annoyed listening to the sound of his brothers heels on the wooden floor.
"If you hadn't wedgied me while I was wearing a thong, I wouldn't be having this problem right now." He went to sit sideways but quickly stood back up, shaking his head and clutching his crotch. "You've left me bruised and broken, brother."
"You're lucky, you deserve so much more pain."
"Just keep telling yourself that if that's what helps you sleep at night." Damon made one last attempt to sit down before giving up and standing awkwardly by the wall.
"I don't feel guilty about any of this."
"You should, if I were human there's a 90 percent chance you would have destroyed my ability to produce children."
"If you're trying to make me feel guilty, you're failing. Stopping you having children would be considered a good thing."
"Denying the world of more cheekbones like these, it would be a crime." Damon stated, stroking his face for emphasis.
"Allowing your genes to multiply would be a crime." Stefan stated in a matter-of-fact tone.
Damon rolled his eyes and headed off upstairs, muttering something Stefan could have sworn sounded like 'Better than mini Stefan's with extra big chins and eyebrows.'
"What are you looking so smug about?" Damon asked as he came downstairs to find Stefan grinning like the Grinch when he stole Christmas.
"We're expecting guests."
"We?" Damon inquired, quirking an eyebrow. Stefan didn't have to reply as the doorbell rang and he quickly got up to answer it. Damon turned to face the doorway to see Elena and Caroline walking in with Stefan following behind them looking extremely proud of himself. "Oh God, what now?" Damon groaned dramatically.
"We come bearing gifts!" Caroline called excitedly, holding up the bag Damon hadn't noticed she'd been carrying.
"What's in the bag blondie?" He eyed the bag like it was a bomb about to explode.
Elena and Caroline shared a grin, looking at each other, then at Damon, then back to each other before back at Damon again. "Corset." They said in unison and Damon's face fell.
Damon sneered as Caroline and Elena advanced on him with the dreaded corset. The second the word had fell from their mouths he'd made an attempt to escape, only to be stopped by Stefan and have his daylight ring taken. He'd tried to get it back but Stefan was always one step ahead of him. After a few failed attempts at stealing it back he decided to hear Stefan out. In order to get his ring back, all he would have to do was do as they say and wear what they say. He agreed, that was until he actually saw the corset.
"I'm not wearing that." He pointed towards the corset, taking a few steps back before hitting the wall.
"Why? It's a good one." Caroline holding the corset up to herself and admiring it as the three of them cornered Damon. The corset to Damon looked ridiculously small and the netting on it looked extremely itchy. The only thing he considered nice about it was that the shade of blue wasn't so bad.
"Yeah Delilah, it's a good one." Stefan smirked, loving the look of horror on his brothers face.
"I don't care, I'm not wearing it." Damon folded his arms and pouted.
Stefan held up Damon's ring, wiggling it back and forth as he headed towards the closed curtains. "You sure about that?"
Stefan only had to burn Damon once before he agreed to wearing the corset. He watched in amusement as the girls dressed a petulant looking Damon. "Pull them tighter." He stated, watching in satisfaction as his brother grimaced.
"Any tighter and I'll have a broken rib to go with my bruised balls and sore butt." Damon gasped out, clutching his side as the blonde vampire tugged harder at the strings.
"Good, if I can't bother you I'll torture you instead."
"But you're not torturing me, blondie and the corset are." Before Damon could react Stefan dashed over, grabbed the corset strings and yanked them. A bunch of expletives left Damon's mouth as his face turned red and his face contorted.
"I believe that was me torturing you."
Damon didn't say anything, just clutched his side and tried to wriggle around and loosen the corset strings.
"We got you these." Caroline called cheerfully and pulled out a pair of extremely high clear platforms.
"We thought you could go for the hooker look today. It suits you more than something classy." Stefan was amused. Damon looked like he wanted to charge him and snap his neck, but he was holding back. He wasn't going to let Stefan win, he was just too stubborn. The older Salvatore narrowed his eyes before taking the heels from Caroline, sitting on the sofa and slipping them on his feet.
"Makeup time." Caroline muttered to herself, grabbing the makeup bag before pulling up a chair to sit in front of Damon. She peered at his skin, running her finger over it before furrowing her brows. "Your skin's a little dry today," she stated, peering closer at Damon's skin." She reached into the bag beside her and pulled out a tub of exfoliating face wash. "We're going to need to exfoliate."
Damon leant back as far as he could, his eyes widening. "You'll do no such thing, my skin's sensitive, you're not scrubbing away at it with that."
Caroline turned the tub around to face him. "It's for sensitive skin." She, pointed at the writing.
As Caroline scrubbed Damon's face he complained the entire time that it was burning, that he was going to start bleeding and that he could feel tingling which could only mean he was having an adverse reaction to it. At one point he even pretended to choke, claiming that his throat was starting to close up.
"We should have laced it with vervain…now that would have been a treat." Stefan commented from where he was grinning smugly in the corner of the room.
"Um, excuse me, I'm a vampire too. I don't exactly want my hands burning." Caroline scolded, narrowing her eyes at Stefan before wiping the product off Damon's face and reaching for the moisturiser and makeup.
Caroline worked away, brows furrowed and her tongue peeking out the side of her mouth as she applied moisturiser, primer and foundation to Damon's face. "The foundation isn't covering properly, we're going to need to wax your upper lip." The words had barely left Caroline's mouth before Damon jumped up and backed away into the corner, shaking his head vigorously from side to side.
"I've agreed to a corset, hooker heels and exfoliation, waxing is just crossing the line."
"Oh my God, you actually have boundaries?" Elena gasped dramatically, holding her hand up to her mouth. She'd been that quiet that Damon had actually forgotten she was even there.
"Surprisingly, yes."
"So let me get this straight, after all the things you've done in your life – staking vampires, compelling and killing people…waxing is just a step too far?"
Damon rolled his eyes before nodding.
"Well that's just tough, this is my week, what I say goes."
"I think you'll find the item that gives you full control is still sitting safely on my list."
Stefan sneered, "What's the matter, scared it'll hurt?"
"No. I'm protecting my masculinity."
"You're wore a bra and thong, you're wearing heels, a skirt and a corset…you've been wearing makeup. Any masculinity you had went away the second you put on that red thong."
It took some persuading, but after an half an hour they managed to talk Damon into it. Stefan even pinned him down just to be sure he could take off and change his mind at the last minute. Caroline had started, but Damon insisted the wax was too hot so she waited for it to cool down before putting it on his lip and placed the strip over the top.
"One, two—" she didn't wait for three, just ripped the strip and watched in amusement as Damon's face contorted and his eyes watered slightly.
"Was that a bit painful?" Stefan cooed mockingly.
Damon gritted his teeth as Caroline placed the soothing moisturiser over the top. "Nope, I can handle anything you're planning on throwing at me."
Damon's makeup was soon applied so his outfit was in full swing. He'd decided to do a few laps around the house after taking a couple of steps in the heels before stumbling sideways, crushing a cabinet and flashing his French knickers to them all.
The rest of the day didn't go according to plan. They had intended on taking Damon out in public, but he was ridiculously unsteady on the heels. They'd suggested him changing but he'd refused, insisting that he was going to get the hang of them. Really, he'd just wanted to avoid going out in public, but his plan had been flawed. He'd eventually managed to walk in the heels without endangering himself or cabinets and found himself tottering to the Grill, Caroline and Stefan walking either side, ready to catch him if he fell.
Damon received quite a few looks as walked into the Grill, most of which were ones of confusion at the large, strange-looking, barely dressed 'lady'. Damon didn't seem to notice that though, all he noticed that all eyes were on him so he was revelling in the attention as he strutted towards the bar.
"Why were you walking like that?" Caroline asked, brows furrowed as she slid onto one of the bar stools.
"I was totally working it." Damon grinned, picking up his drink the second the barman placed it down.
One and a half bottles of bourbon later and Damon was wasted. Stefan watched in half annoyance and half amusement as he realised his brother was the type of drunk girl who tried to remove her clothing.
"Will you stop it." Caroline stated as Damon flopped his torso down onto the bar top, his arms moving awkwardly as he tried to undo the ties on the back of the corset. "People are looking." She hissed, noticing over half the people in the Grill were looking at the scene taking place.
Damon lifted his head up, wig wet from the whiskey he'd spilt on the bar earlier. "Let them look, I'm uncomfortable." He whined kicking off a shoe and sending it flying halfway across the room. He watched it land before smiling to himself and kicking off the other. This time however, it landed in someone's food, sending the meal flying in the customers face and the drinks on the table flying. Damon watched in amusement as chaos broke out at the table, it's occupants jumping up and frantically trying to wipe the wet from their clothes.
"You're going to have to get him out of here." The barman stated towards Stefan, using his eyes to signal towards a chuckling Damon.
"Hey!" Damon shouted, turning to face the barman whilst Stefan and Caroline took hold of each of his arms. "I'm a lady!" he shouted, puffing out his padded chest for emphasis.
"Yeah, sure man." The barman looked awkward as he rubbed the back of his neck, looking pleadingly at Stefan to just get the crazy guy out of there.
"I am woman!" Damon shouted, pointing an accusatory finger at the barman whilst Stefan and Caroline began to drag him backwards. "I am woman!" he shouted again, his heels dragging against the floor. "I am woman! I am Delilah!" With that they dragged him outside, the doors swinging closed.
Between the three of them it took them an hour to get Damon home. Every single person they came across, Damon felt the need to tell them the story and get angry when they didn't share his shock at the barman calling him a man. After a few people got yelled at and hit with Damon's purse, Stefan took matters into his own hands, snapping Damon's neck before swinging his brothers unconscious body over his shoulder.
"You're like a caveman carrying your woman home." Elena snort laughed as she followed behind, chuckling every time Damon's hands slapped against Stefan's butt with each step.
"Are you going to tell him he touched your butt?"
"No, it's not something I want to remember, never mind share."
Elena laughed loudly and Stefan turned round, frowning at the cell phone clasped in her hands. "Sorry, but this is something I never want to forget. Goodnight caveman." Stefan watched as Elena blew him a kiss before heading off towards her house.
Stefan sighed, hitching his brother further onto his shoulder. "Damon Salvatore, you're a pain in my ass."
The next day Stefan sat at the bar in the Grill, spinning the glass between his fingers on the table top and watching as the amber liquid swirled around. He was disappointed. His attempts at humiliating Damon hadn't worked as well as he liked. It turned out his brother had extremely thick skin and pretty much nothing phased him. All he'd managed to do was cause physical pain and that wasn't the type of torture he was aiming for. He only had one more day to think something up and he was feeling at a loss.
"Stefan mate, how the hell are doing?" Stefan looked up to see Kol sliding onto the seat next to him and ordering a drink.
"I don't like you."
"That hurts, I thought you loved me, darling?"
"I despise you."
"The feeling's mutual, you want to know what else is mutual? Our contempt towards your brother. I heard about your day of hell, why not make this his week of hell. I can help you."
Stefan eyed Kol suspiciously as the youngest Mikaelson male cast him a smirk. "What did you have in mind?"
Stefan and Kol's plotting had filled their heads with ideas from putting itching powder in Damon's tights to selling him to a man Kol met in Egypt in exchange for a camel.
"I don't think he's worth a whole camel." Stefan chuckled to himself.
Kol sighed and looked around the bar, his eyes suddenly widening before he turned to Stefan. "We hire him out as a prostitute."
Stefan choked on his drink. "What?!"
"We get him to go home with some drunken fool, imagine the sheer horror when the unfortunate customer realises he got a whole lot more than he bargained for."
"I like your thinking, but there's no way Damon's going to go home with some guy, even if I do threaten him."
"I know and that's why we'll drug him. Imagine the look of terror on his face and the thoughts going through his head when he wakes up in a strange bedroom with some half naked guy leering over him?"
Stefan thought for a moment. He had to admit the idea was gold, but he had doubts it would even work. Also, he didn't want anything to happen to Damon while he was out cold, but then again what exactly could happen. It wasn't as if he could be killed normally and any man wanting a female prostitute certainly wouldn't do anything with Damon after figuring out his real gender.
"I like it. Now, how are we going to go about this."
"Follow my lead." Kol grinned, getting up from the stool and heading to one of the corner booths in the grill. Stefan finished his drink and following, his eyes landing on a lone man.
"Excuse me my good man," Kol stated, approaching a drunken man who was hunched over his drink. "What are your thoughts on prostitution?" Stefan had to stop himself from choking. Kol certainly didn't do things by halves.
The man looked up at Kol before a sneer appeared on his face. "You're not my type."
Kol laughed. "That's funny, but you're not my type either darling. I do however know of a young lady who's extremely filthy and even cheaper. She'll be in here later and I happen to know the secret to get the night of your life from her."
The man sat up, his shoulders rolling back as he narrowed his eyes at Kol. "Why would you do that?"
"Because we're friends."
The man eyed him suspiciously. "What you playing at?"
Kol held his hands up defensively. "Nothing. I'm always looking to help a friend out."
"Since when have we been friends? I don't even know you."
"I'm everybody's friend, I'm just that nice of a guy."
"Seem like a bit of a creep to me." The man sneered.
Stefan half expected Kol to snap and drain the man entirely, but strangely he laughed before sliding into the booth opposite the man. "Darling, you're lucky I'm not sensitive."
Stefan slid in after him, waiting for the man to get up and leave, but he didn't. Instead he leaned further across the table.
"Tell me more, how do I get this girl."
"It's simple really, no charm or skills necessary. She'll come in, I'll point her out to you. You go up and buy her a few drinks. On the third slip this into her drink when she's not looking," he placed a small vial of liquid onto the table, "when it starts taking effect, take her to your home or where you're staying and lay her on the bed. Don't do anything other than get ready. Wait for her to come-to and you're in for a wild ride."
"That easy, huh?"
"Yes, that easy. In fact, here's a picture for motivation." Kol reached into his inner jacket pocket, pulling out a folded up piece of paper. Stefan observed as he unfolded it, revealing the picture he'd used for the posters. "She's something, isn't she?"
"Something's right." The man muttered, taking the picture from Kol's hands and looking at it.
"You can keep that." Kol stated, sitting back and flashing the man a smile.
"So, where can I find her?"
"She'll be here very soon. In the meantime, I could do with a drink, another one?" Kol asked the man who just nodded, his eyes still focused on the picture in his hands.
Kol came back with drinks and they sat in silence. A few times Kol attempted to engage the man in conversation but he just grunted, not removing his eyes from the picture. Stefan was bored. Despite his genius idea, he really didn't want to talk to Kol. The original may have helped him out, but it didn't mean they were friends or that they liked each other. He was certain that once the week was over they'd go back to how they were before.
"She's here…" Kol sang, a demented smirk forming on his face as he watched Damon enter the bar. He was confident on his feet now and kept flicking his hair every so often.
"Where?" the man questioned, looking around the bar. Kol slid from the booth and the man did the same, standing right beside him. Stefan grinned to himself and slid out, wandering to stand behind the panel of one of the booths. He wasn't going to miss this for the world or screw it up by having Damon spot him.
"There she is." Kol pointed across the room to where Damon had sat at the bar. The man looked over, his eyes trailing him up and down before he nodded.
"I like 'em well built. What's her name."
"Delilah VanBooben." Kol stated, his face entirely straight. Stefan snorted, wondering whether Kol had planned using the name or if it had been a spare of the moment thought.
"VanBooben?" The man quirked an eyebrow.
Kol nodded. "She's Romanian, quite the gymnast so I've heard."
"You've never…?"
"Oh no, I'm much to clean handsome, she prefers rugged…men such as yourself."
The man considered what he'd said for a moment before nodding and sauntering over. As the man approached Stefan moved back to stand next to Kol, their arms folded as they waited for the fun to begin.
"You do realise he's going to flip." Stefan stated, watching his brother unsuspectingly downing his drink.
"I'm immortal and unless he has a white oak stake lurking around, I'd say I'm safe. You on the other hand, I'm sure the fact you're his brother will excuse you from being killed."
Damon entered the grill and walked up to the bar, taking a seat on one of the stools. He was surprised how quickly he'd picked up the whole walking in heels thing, but that being said they were still as uncomfortable as hell. He ordered a drink, downing it quickly in hopes of it numbing the pain in his feet. He was about to order another when a man slipped onto the stool beside him, grinning widely.
"Can I buy you a drink?"
He looked the man up and down, deciding he was really creepy but deciding to accept. Who was he to turn down a free drink? He cleared his throat and adopted his girl voice. "Yeah, sure. Bourbon. Straight."
"Hard Liquor? My type of woman." The man grinned and licked his lips at Delilah before ordering her drink.
Damon was two drinks in and really couldn't be bothered to socialise with the man who was leering over him, but he certainly wasn't one to turn down a free drink so he decided he'd just deal with it, make polite conversation, get a few more drinks out of the man then return home.
After his third drink, he started to feel strange. His vision was becoming blurry, but he hadn't had anywhere near enough to make him drunk. He could drink a whole bottle and not feel even the tiniest effect from it. As his vision grew worse he started swaying, almost falling over only to have the man catch him.
"Steady on there Delilah." He stated, hitching him up and putting his arm over his shoulder. "Come on, we'll get you some fresh air." Damon could hear the words coming from the man's mouth and wanted to protest but he couldn't be bothered, instead he nodded in agreement. Fresh air sounded like a fantastic idea, his head was feeling rather hot from the wig.
The cool air brushed at Damon's face, his wig feeling less irritating, but doing nothing to quell his dizziness. The man said something that Damon didn't hear but he nodded. He could have sworn he heard the word sleep and right now sleep sounded like the best idea ever.
Half way down the main street, Damon's vision went completely, but he could hear the man saying that they were nearly there and that he could go to sleep soon. Damon nodded, but he wasn't entirely sure that his head followed what his mind said it was doing. The last thing he could remember was feeling his head hit a soft, but scratchy pillow before sleep took over him.
As Damon woke, he groaned at the pounding in his head. He didn't know where he was or how he got there, but the rough sheets beneath him certainly weren't his own. His immediate thought was he'd found some girl, until he remember – he'd been dressed as a girl, so that was pretty much out of the question. He opened his eyes slightly to find the curtains closed and the room he was in dimly lit. A hotel room.
Damon groaned again as a shooting pain surged through his head. He opened his eyes, squinting into the dimmed room. There was a man sat on a chair at the foot of the bed wearing only his boxers and a manic grin. "You're awake my angel." Damon's eyes widened in horror. "Don't panic my sugar, I've been waiting for you to wake up. I loved watching you sleep." Damon jumped up, grabbing his purse from the bedside table as the man stood up, barely reaching his chin. "You're a big girl, I like that." The man's hands landed on his hips. Damon quickly shoved them off before jumping over the bed.
"The boy told me you'd be feisty." The man smirked, licking his lips as he prepared to pounce.
"Wait, Boy? What boy?"
"Don't remember his name, posh boy, think he was a bit of a woopsie, called me darling – would have knocked him out but his friend looked like a bit of a hard case. Broody looking guy."
"Kol." Damon growled. He should've known the youngest male Mikaelson would have something to do with it and he wasn't claiming to be psychic, but he was fairly certain the 'broody looking guy' was Stefan.
Damon didn't say anything to the man, just quickly grabbed his shoes and left the room. As he walked down the street plotting the death of his brother and Kol, his shoes and pursed grasped in his hand, he tuned out from the rest of the world, ignoring the strange looks people were giving him. He was sure Kol had been the mastermind behind the plan, there was no way Stefan could have thought something like that up.
Damon entered the house to hear hushed voices talking from the living room, he veered round and stopped in the doorway to see Stefan sitting on the sofa. He quickly eyed the room, looking for who Stefan was talking too but he couldn't see anyone, so instead he walked into the centre of the room, stopping just short of Stefan.
"Good morning sunshine." Stefan grinned up at him looking like a kid at Christmas.
"You and small fry, you're dead." Damon shouted, his fists clenched at his sides.
"Late night darling? How was the walk of shame?" Kol's voice sounded as he strutted through one of the other doors, a proud smirk on his face.
"You," he pointed a finger at Kol. "You're going to regret this."
"I have no regrets, never have and never will." The smug calm look on Kol's face gave Damon a strong urge to beat it away.
"Oh I'll be sure to make you regret this."
"What makes you think it was my doing?"
"For one, Stefan doesn't have the kind of mind to think of something like that and secondly, our new friend described you perfectly – 'little weasel looking kid' I think his exact words were."
"You've wounded me." Kol stated dramatically before chuckling, stopping briefly as he dodged the heeled shoe Damon sent flying at his head. "Now there was no need for that."
"When you're involved there's every need."
"Come on, you've got to admit I got you good."
Damon laughed manically, shaking his head from side to side. "Wrong small fry, your little stunt has left me unaffected, apart from a stronger urge to torture and kill you." With that Damon turned and headed upstairs. Kol had just left when Stefan heard Damon's door opening.
"Where are you going?" Stefan questioned as Damon came down the stairs dressed in his 'best' outfit.
"Out, it's the final day and girls just wanna have fun and all that jazz." Stefan quirked an eyebrow. "Basically, I'm going to go out and spend the day getting blind drunk before dancing my feet into a heel induced coma."
Stefan nodded and stood up. "Okay let's go then."
"Should we tell him his wig's fallen off?" Elena questioned, looking to where Damon was dancing around, eyes closed and waving his drink around in time to the music. They'd been at the grill for two hours and Damon had been drinking like a sailor. He'd already finished a whole bottle of bourbon and the one he had waiting on the bar for him was almost gone.
Stefan cast his eyes up to his brother and took a sip of his drink. "Nope, just let him keep going."
If it had been any other time, he would have done something to humiliate Damon, but he'd decided to just let him do it on his own. There was no need for him to act any further because as Damon danced around unaware, Kol was off somewhere carrying out another one of his master plans.
Stefan had asked what he was up to but Kol had refused to answer, just telling him that all would be revealed in good time and that patience is a virtue.
Damon felt something beneath his foot and looked down to see a bunch of hair on the floor. He ignored it before something in his brain clicked. His head was no longer melting or itchy. He reached up and patted his head – his wig was gone. He looked around to see people staring at him. He casually bent down and picked it up, put in on his head. He knew it was askew, but he wouldn't be seen getting worked up. Instead he flattened it best he could and sauntered out the door.
The second he stepped outside and the fresh air hit him, he realised exactly how drunk he was. He was so drunk that he didn't even notice Stefan and Elena following behind him, videoing him as he removed his shoes, then his wig, then his jacket, then bra, then pantyhose, then thong, tossing them to the floor behind him as kept walking. He even started into a little dance whilst singing "Girls Just Wanna Have Fun". Stefan knew the journey to Damon would be a blur, but he'd be certain to show him the video as a constant reminder.
Damon woke up with a slight ache in his head and noticed that he was barely dressed. He groaned at the constriction of the skirt before he realised. It was over. He'd served his time and despite the odd hiccup along the way, he'd come out virtually unscathed.
Stefan listened glumly at the sound of running water and Damon singing loudly. He'd failed. The week had been a breeze compared to what Stefan had hoped would happen and Kol had never actually followed through with his plans as promised.
Damon came from the shower, saluted Stefan and then headed out the door. He had intended to stay and chat, but he was in too much of a good mood and wanted nothing more than to go and get drunk without having to worry about falling over in a skirt and flashing everyone in the vicinity.
"Hey," A gruff voice called just as Damon took a sip of his first drink. He turned slowly, his eyes widening in horror as his "Client" stood before him. "Don't I know you from somewhere?" he inquired, leaning forward to peer closer at Damon, his Tequila soaked breath making Damon's stomach churn as he vigorously shook his head.
"Hey there Delilah." A familiar voice sang as someone brushed into Damon. He looked up and glared at Kol's retreating form as he looked over his shoulder, flashing Damon a devilish smirk. Damon turned his attention back to the man who watched as Kol left before turning back to Damon, his eyes widening in horror.
"You." Damon rolled his eyes and stepped forward. He was going to have compel the man to forget, to leave mystic falls and never return, then he was going to torture and kill Stefan and Kol.
After a long day of trying to clear up the mess created from the week Damon slumped down onto the sofa. He was just getting comfortable when his phone started vibrating in his pocket. He fished it out, looking at the name on the screen.
"Elena, how can I be of service?"
"I'm going to send you a link, you might want to check it out. It's all over town."
He ended the call and a text buzzed through on his phone. He clicked the link, a web page opening.
Damon Salvatore A.K.A Delilah VanBooben.
There was numerous pictures of him getting dressed up as a woman. He shrugged. Nothing new there. The video's however, they certainly captured his attention.
The sound of the front door opening spread a grin across Damon's face. Stefan was home. He'd been so smug after his and Kol's little stunt and had been fairly certain that Damon had been somewhat traumatised by the experience. How wrong he was. In a way Damon found it kind of amusing, they'd obviously put a lot of effort into the plan, but he doubted the outcome was what they'd imagined.
Damon's grin widened as Stefan came into the living room. "Looks like you've been screwed over, brother." Stefan's brows furrowed. Damon sat forward and turned the laptop round, hitting the play button on the video he considered to be the 'best'.
Stefan watched, his face contorting as a video showing his and Damon's "Love" played across the screen complete with "My heart will go on" playing in the background.
Stefan slammed the laptop closed, his fists clenching at his sides. He was about to storm off upstairs when he caught a glimpse of someone looking in their window with a devilish grin on their face. Damon stood up, glaring at the person.
"Kol Mikaelson, you're dead!"
"Undead actually darling!" He called through the window before quickly taking off before the Salvatore's could even blink. He knew his actions would have repercussions, but passing up on an opportunity to humiliate the Salvatore's wasn't something he would ever forgive himself for doing. Whatever they were going to attempt to do to him, he could take it. He was after all, an original.
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