This is for Sherlocksmiley and . .ashes who requested roleplay. and for monaysalvatore for requesting Fantasy Friday again. I hope everyone enjoys this one. I liked writing it and hope you like reading it. If anyone has any ideas, or wants to see more Fantasy Friday then send me some ideas. Thank you yet again for your continued support for this story. I appreciate each and every review I get. Thank you so much.
PS I own nothing, if I did DE Fantasy Friday would have existed a long time ago. ;)
"It's Fantasy Friday again. So what's the plan for tonight?" Caroline asked Elena excitedly.
"It somehow ended up being his turn to pick again. Let's just say I lost a bet and the bet was for an extra week of choosing the fantasy. Now here I am, waiting anxiously to find out what it is." she said.
"What was last weeks again?" Caroline asked.
"Bad student and teacher. He was the teacher. I was the slutty school girl." Elena said smirking.
"So hot. Tyler and I so have to try that." Caroline said.
"You should. It will turn your sex life up a few degrees to say the least. And I guess I cant really be mad at him for winning the bet. He picks much better fantasies than I do. So much more creative." Elena said grinning.
"Well he has had so much more experience." Caroline told her.
"That is true." Elena said absentmindedly when her phone vibrated. She glanced at the phone and grinned when it said Damon.
"It's Damon." she said excitedly.
"Oooh what's it say?" Caroline asked excitedly.
"You have some shopping to do baby. The theme isn't much of a secret when I tell you to go pick something out easily strippable. If you haven't guessed already, you are my sexy stripped tonight, and I am your client. Do your worst. I'll be awaiting you. Don't make me wait." she ready out loud.
"Oh my God. You have to let me help you shop. Please Elena. Pretty pretty please." she begged.
"Fine. You can come. Although I have no idea where I would go to pick up something stripper friendly." she said furrowing her eyebrows.
"I know just the place. I have had some experience with extremely naughty lingerie and other apparel." she said grabbing Elena's hand and pulling her towards the doors. Elena laughed especially as school wasn't even over yet.
"You do realize we are supposed to be in history right now, right?" Elena asked as Caroline drove them through downtown Mystic Falls.
"Oops, this mission made me a little excited. Oh well, we can deal with it on Monday." Caroline said shrugging her shoulders.
"I suppose we can. Let's go shopping." she said enthusiastically.
"I know you better than that Elena Gilbert. I know that you have never been in this store before and you're nervous about purchasing something from you. Do not worry, Caroline is here." she said smiling.
"What would I do without you Caroline Forbes?" Elena said hugging her friend tightly.
"Well you would be standing by confused whenever Damon gives you a new mission such as this." Caroline noted as she pulled her into the store that appeared to be stocked in sexy lingerie, and easily strippable clothing. The girls perused the racks. Caroline had a rather large pile of stuff to try on while Elena hadn't yet chosen anything.
"Elena come on. Just remember this is for Damon." Caroline told her, seeing her still empty arms.
"Right. Damon. I love dressing up for him, I just hate shopping for the stuff." she said.
"Well if you are to be a stripper for him, you have to go there in costume." she said.
"I guess you're right." Elena agreed. She started looking through the racks when she found a purple sequined outfit that screamed slut.
"How about this?" she asked holding up the purple hot pants made of a leather-like material. And matching push up bra, both covered in sequins.
"That is hot. It's perfect. Now just need some hot stripper boots and thigh highs." she said.
"Okay. Lets go." Elena said more confident now that she found the outfit.
"I have the boots at home, they have stripper written all over them. Super high heeled. I also have a black trench coat that you can wear over. We just need to find the thigh highs for you." she said.
"Thanks Care." Elena said as they moved to the other side of the store where the accessories were located. They found a pair of black thigh highs and they went to pay for their purchases.
"Come to my house. I'll get you all stripper ready." she said as they walked out of the store. They walked down the street to where they parked the car before running into Alaric.
"Ladies, may I ask where you were in my class this afternoon?" he asked with his hands on his hips. "Especially you Elena Gilbert. After all I happen to know you went to school this morning because I happen to live with you." he added.
"It's Friday." Elena answered hoping he wouldn't ask questions.
"And why were you coming out of that store?" he asked staring at the bags in their hands.
"It's Friday." Elena answered again.
"I don't care what Caroline does on her own time, but Elena, I am your guardian." he said trying to figure out how to have a partial sex talk with a girl who was dating Damon Salvatore.
"It's Friday Ric. Damon is waiting for me." she said hoping he'd hurry it up.
"What is this whole "It's Friday" thing?" he demanded, wanting to know what kind of debauchery his friend did to Elena on Fridays
"Well, if you really want to know, Damon and Elena have a kinky role play night every Friday." Caroline explained.
"Oh. Yuck. Why did you skip my class to go shopping?" he asked them both.
"Damon texted and told he the theme. We needed to get some shopping down to get her ready for this. But we have to go. Time is running low. She has to be there in a little while." Caroline said grabbing Elena's hand and pulling her to her car.
"I will be having a chat with Damon about this." he called after them. They ignored him and started the car up peeling out of the parking spot and speeding to Caroline's house.
"That was awful. Alaric is my guardian and I'm off buying stripper clothes so I can strip for my boyfriend who happens to be Ric's sort of best friend." Elena groaned.
"It's okay. Nothing bad will happen." Caroline soothed her friend as she pulled into the driveway and walked Elena into the house and to her bedroom.
"Okay. Now let me do your hair and makeup. I am going to make you into a sexy seductress." she said getting to work on her. She curled her hair and tousled it making it look sexy and left it down before moving on to her makeup. She made it dark and black making her look like someone entirely new.
"Now get dressed. I'll bring you the shoes and the trench coat so no one sees what you're wearing or not wearing underneath." she said.
"Thanks for your help Care. You really should try this with Tyler. It's so fun." Elena said her confidence returning. It seemed as long as she had the costumes with her and didn't have to buy them, then she was fine. Elena waited for the rest of her costume before closing the bathroom door.
"I will never be able to walk in these boots." Elena groaned seeing the insanely high heels. There was a huge platform and at four inch heel. They were scary as hell. They were leather and they went up to her thighs. They were sexy but terrifying.
"It's not as hard as it looks. You just have to make it from here to the car and the car to Damon's front door. You'll be fine." she assure her friend.
"I have to drive in them." she reminded her friend.
"You'll be fine." Caroline assured her again. Elena sighed and dressed in the slutty costume before putting the trench coat and tying it tight around her waist.
"I'm ready." she said wobbling out of the bathroom in her heels.
"You look great." Caroline said fixing her hair before giving her a gentle shove. "I'll drive you to the boarding house, considering your car is still at school." Caroline stated remembering the oh so important fact.
"Thanks." Elena said gratefully. The girls left the room and walked out to the car.
"Okay, I'm ready." Elena said nodding her head.
"Let's go." Caroline said starting up the car and speeding towards the boarding house. When they pulled up in front of the house, Elena smiled brightly.
"Thanks Care." she said before opening the door.
"No problem. Have fun." she said grinning.
"I will. Don't worry about that." she said grinning and getting out of the car. She took a deep breath and walked up to the doorbell. If she was playing stripper, she had to do it right. And she was pretty sure strippers rang the doorbell, not walking right in. She pressed the button and stepped back waiting for him to answer. She heard the car drive away seconds before Damon answered the door.
"I take it you're the stripper?" he asked grinning lasciviously at her.
"That is right." she said grinning right back at him.
"Come on in. The money is on the table there. It's all yours if you can please me." he said.
"That is not how this situation works sir. I get paid and you get pleasure. No pleasure if there is no money." she said smirking at him.
"Well. What kind of pleasure do you give?" he asked raising his eyebrows at just how good she was getting into character.
"It depends on how much money I get. I aim to please, that's why I'm so popular. I've been known to give blow jobs, or even to let the client fuck me if the money is right." she said smirking at him.
"I think I might like you. There is four hundred dollars there. How much can that get me?" he asked.
"Well since you are oh so hot. I'll give you the whole package. I'll strip,give you a mind-fuck blow job and then you can fuck me however you want. Just because I like you and judging by the bulge in your pants, you might be talented in that area. I like talent." she said.
"I think I like you too. Now let's get this show on the road." he said going to hit in the easy chair that he had turned around so he could watch her strip in the big open area of the parlour.
"As you wish." she said standing in front of him.
"Do you take dollar bills?" he asked.
"No. I'll strip and dance for you. Then you get the bonus's I told you about. Leave your money over there and I will take it when I leave." she said running her hands down her body to the tie on the coat.
"Sounds good to me." he said getting comfortable in his chair. She pressed play on the stereo, causing a sexy song to start playing over the speakers as she untied the rope on the jacket. When that was untied she moved up to the buttons and undid them one by one, agonizingly slow while her hips swayed to the beat of the music. He watched, his eyes fixated on the slivers of skin that were coming visible. By the time she made it through the buttons on the jacket he was painfully hard in his jeans but his eyes bugged out when he saw the purple outfit she was wearing under it. He swallowed thickly at the sight before him.
"Do you like?" she asked spinning around so he could see her from all angles.
"Hell yeah." he answered thickly. She smiled and swayed over to him so she could run her hands down his chest. Desperately needing to get out of the boots that were killing her feet, she lifted her foot onto the chair he was sitting in and slowly started undoing the zipper on the thigh high boots. He licked his lips as he watched her remove the footwear. He was amazed she could make something like the removal of shoes look so sexy. When the shoes were gone she climbed onto the chair and started moving over him, giving him a lap dance. Every movement, brought her covered core close to his dick which was straining against the zipper of his pants and her breasts close to his mouth. Knowing he wasn't allowed to touch he left his hands where they were although she was causing him an immense amount of pain. He was so hard, he was sure he would cum in his pants like a teenage boy in now time at all.
"Please start taking off your clothes." he begged knowing that she wouldn't give him the "bonus's" until she was done her stripper routine.
"As you wish." she said smirking at him. She rose off of him and lifted one of her legs back onto the chair where he was sitting as she pushed the thigh highs down her leg slowly. When the first one was gone, she moved to the second one until her legs were bare. She was hiding it well but she was almost as desperate as he was. She needed him. She could feel the tingle between her thighs and all she wanted was for him to make it go away. She reached behind her and unclasped the purple bra and tossing it to the floor leaving her topless in front of him. She covered and squeezed her breasts in her hand, knowing his eyes were fixated there and his hands were clenched into fists on the arm rests of the chair, trying to keep from touching himself. Her hands slowly trailed down her body and slipped under the top of her extremely short shorts teasing him. After teasing him and herself for a moment, she pushed the shorts down her body leaving her completely nude for him. Her partially shaved pussy completely bare for him.
"Are you satisfied with the show sir?" she asked as she stood before him naked, shamelessly.
"Very much. How about the bonus's that you offered?" he asked.
"Ah yes. That. Well I suppose I should give you what I offered." she said walking over to him.
"Yes, you should. Just feel how hard your little show made me." he said grabbing her hand and pressing it to his package.
"That must be painful." she noted as she unbuttoned the jeans and snuck her hand inside.
"It is." he agreed.
"I have to see you. Lift your hips." she ordered. He did as she told and she pulled the jeans down leaving his bottom half naked. His cock rose to his belly button and she licked her lips sexily.
"Wow, I cant wait to taste you. You are huge, the biggest I've ever seen." she said still in character.
"My girlfriend says that too." he smirked.
"Ah, cheating on your girlfriend? Where is she tonight anyways?" she asked.
"Not sure. Probably with a male stripper." he smirked.
"That's hot." she grinned dropping to her knees before him. "How do you like it?" she asked as she rubbed his length from base to tip.
"However. I'm going to cum down your throat regardless." he told her.
"That's how you like it? You like cumming down the woman's throat?" she clarified.
"It's so hot." he told her. She nodded and latched her mouth onto his tip sucking hard. He yelled out at the suddenness of her attack and thrust his hips up. She continued sucking and licking at him under his rough treatment, while she searched for relief of her own by touching herself while she was sucking him off.
"Don't touch yourself." he told her when he seen what she was doing. She stopped her ministrations on herself and moved both hands to his cock and rubbed the part that didn't fit in her mouth. When he came, he yelled out and shot his massive load down her throat in thick milky streams. She licked him clean before pulling off and licking her lips.
"Yummy." she said smirking.
"You look uncomfortable." he noted as she rubbed her thighs together.
"I am." she told him.
"It shouldn't take too long for me to get aroused again." he said as he started rubbing his dick up and down. When he started hardening in his hand, she climbed back up to straddle him.
"You are big, lets see how you feel inside me." she said as she sunk down on him. He grasped her hips and dove down to attack her nipples with his lips and teeth causing her to scream out. She was definitely not being quiet tonight, as she screamed every time he hit a new spot inside her, or bit her nipples. She rode him at a fast and furious pace, slamming herself down on him on every stroke. She was being thoroughly rough with him and he liked it. He squeezed her hips tighter than necessary as she rode him to completion. She came first and he followed right behind her, her muscles milking him dry. He moaned into her chest as she screamed out his name at the top of her lungs as she came. When they recovered she didn't move quite yet.
"That was amazing." he said as he pressed a quick kiss to her neck.
"I lost it at the end though. I called out your name. I wasn't supposed to know your name." she said.
"It was so hot though. That was the best one yet." he said hugging her close to him.
"It was. Do I get to keep the money you offered the stripper?" she asked smirking at him.
"After that, definitely. That was fucking incredible." he said.
"Would you consider yourself well-pleased?" she asked raising her eyebrows.
"I would. I would definitely hire you again Miss Gilbert." he said smirking at her as she got back into character.
"Well, I have some free time. Why don't you hire me again right now?" she asked.
"I might just do that." he agreed before swooping in and kissing her lips passionately.
