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Bonnie and Damon were feeling restless. All was basically quiet on the someone-is-trying-to-kill-them front and they were bored.
“Bon, I’m bored,” Damon Salvatore told his best friend – almost girlfriend.
“What do you want me to do about it?” Bonnie Bennett asked as she looked up from the magazine she was pretending to read.
“Entertain me!” Damon begged.
“Um no!” Bonnie said rolling her moss green eyes.
“Let’s play a game,” he suggested.
“No, you cheat,” she reminded.
“Not that kind of game,” he smirked.
“What’s the game?” Bonnie asked nervously.
“It’s called Fantasy,” he said.
“No Damon. I’m not playing a game called Fantasy with you,” Bonnie said.
“Why not?” You don’t even know what the rules are,” he teased.
“I don’t care and you probably just made this game up,” she said.
“No, I didn’t. it’s a game about honesty. And you’re always saying I could stand to be more honest,” Damon chided.
“How is a game called Fantasy about honesty?” Bonnie asked.
“Players have to be completely honest, obviously,” he said winking.
“Explain the damn game, Damon,” Bonnie said frustrated.
“Fine, don’t get so touchy. Each player has to reveal a fantasy in detail and the other people have to give their initial reaction to said fantasy.”
“No, I’m not playing. My fantasies are not your business.”
“Why not? We’re BFFs. It’s about time we found out about the down and dirty side of each other,” Damon said matter-of-fact.
“Your concept of BFF is skewed,” Bonnie said.
“How so? Besties share secrets. Fantasies by nature are secrets. Making this the perfect best friend game,” Damon reasoned.
“No,” Bonnie said emphatically.
“Great. I’ll go first. I admit I have fantasized about Elena, Caroline and you in my shower. At first you’re only taking a shower but one innocent touch by Caroline leads to not-so innocent touches and then you guys are having wild hot sex in my tub and then my bed,” Damon said in a low sexy voice.
“What am I supposed to say to that?” she asked her eyes averted.
“Tell me what you think, Bon,” he implored.
“A couple of things. One, it’ll never happen. Two, I’m surprised you included me,” she told him honestly.
“Why?” he asked.
“I didn’t know you thought of me that way,” Bonnie answered honestly.
“Now you know. Your turn,” he said eyebrow quirked.
“I maybe have in the past fantasized about being tied up,” Bonnie admitted shyly.
“Hot!” Damon commented. Bonnie laughed and blushed. “My turn. OK. I have fantasized about you and me having hot sweaty, passionate sex all over this house,” Damon admitted.
“Wow! When did you have that?” she asked.
“When we were trapped and you very quietly masturbated in your room. You weren’t as quiet as you thought you were,” he answered. “What were you thinking about?” he asked.
“Damon,” Bonnie whispered.
“Tell me,” Damon said moving next to her.
“I can’t,” she said shaking her head.
“You can. Close your eyes and tell me,” he whispered into her ear.
“I fantasied that you would come into my room while I was getting dressed and you’d make some rude comment. I’d insult you and you’d kiss me and we’d have insanely hot sex,” Bonnie admitted.
“You only had to ask, Bon,” he whispered. His warm breath making her tremble. Without opening her eyes, Bonnie turned her head and kissed him.
Damon immediately responded. He pulled her into his lap and lifted her top over head. To his delight, Bonnie has chosen to go bra less. He took her nipple into his mouth and greedily sucked; her skin tasted better than he’d imagined.
Bonnie reached between them and opened Damon’s jeans and reached in to pull out his hard cock. She stroked it leisurely. Damon kissed her again, gathered her skirt around her waist and slid her panties to the side and removed her hand from his cock, then slid home to the sound of a pleasure sigh from Bonnie. She pulled herself closer to him driving him deeper inside of her. Bonnie rode Damon’s engorged cock until she came with a cry of completion to be followed minutes later by Damon’s moan of satisfaction.
“Wow, Damon I…,” Bonnie started.
“Don’t say anything. It’s my turn,” he said.
“What? We’re still playing?” she asked surprised.
“Yep, but now there’s a new rule,” he said.
“OK. What is it?” Bonnie asked as a ripple of excitement passed through her.
“First answer a question. If you were going to have stranger sex would be with a male or female?” he asked.
“You’re serious?” she questioned. He nodded yes. “I guess a woman because it seems less skeevy,” Bonnie chuckled.
“OK. The new rule is we have to act out each others fantasies. No matter how elaborate,” he explained. She nodded her understanding. “So you and me road trip. We stop in a nice wholesome town and I take you shopping in the local mall. While in the mall we pick out a woman we both like. You convince her to join us at a nearby hotel for a little fun,” Damon said.
“Why don’t you convince her?” she asked.
“Nope, cause you would say I used compulsion even though I clearly don’t need it. This way the situation is completely on the up and up. What do you think?” Damon asked hopeful.
“Let’s go,” she answered kissing him.
Bonnie and Damon both tossed a duffle bag in the trunk of the Camero and hit the road. They sang along to 90’s hits and had sex in the back seat. They had a lot of sex actually. In the bathrooms of roadside diners, in hotel rooms, they’d even stopped and had sex on the hood of the Camero a couple of times. By the time Damon pulled into the parking lot of the Pentacities Mall Bonnie’s sexual confidence had grown and she was more than ready to find a willing partner for and Damon.
You weren’t feeling particularly happy today. You had recently, like last, caught your boyfriend cheating on you. It was a blow to your self-esteem. The girl he was cheating with had life threateningly perfect breast. You were positive they were fake. Her tan was fake, her hair was fake and she gave a fake ass apology as you ran her out of your apartment. You’d also kicked him out and had the locks changed and the mattress replaced. All in all you’d had a productive day but it didn’t change the nagging feeling that maybe he cheated because something was wrong with you. Maybe your boobs were too small or your ass too flat your hair too plain. You weren’t sure but you were in the mall to change your hair and insert a little sexy into your otherwise tame wardrobe.
You emerged from the salon your Y/hair color hair looking radiant. It felt silky and soft and you couldn’t help but toss it. Your next stop was Victoria’s Secret. You’d learned the key to being sexy was feeling sexy. So you figured a couple new bra and panty sets would help with that. You noticed an attractive couple standing across from the store when you entered. Not because they were creepy but the two of them standing there together were striking. They were both gorgeous. Without another thought to them you began shop.
“This would look great on you,” a voice said holding a very tiny pair of panties out to you.
“Excuse me,” you stammered.
“I think these panties would look good on you,” she repeated. You realized with a start that she was the girl you’d noticed on your way into the store.
“Um thanks but no,” you said.
“Why not?” she asked.
“They’re not my style,” you told her.
“Oh, too bad,” she said shrugging.
“Why is it too bad?” you asked.
“These scream sexy. It’s too bad you would pass up walking around feeling that sexy,” she said shrugging.
“You’re right. I came in here looking for things to boost my confidence and make me feel sexy. I shouldn’t shy away because it’s not my style,” you said taking the panties from her.
“You’re gorgeous. Why do you need to boost your confidence?” she asked.
“I’m not but thank you. My boyfriend, ex-boyfriend cheated on me with a woman the world deems as gorgeous and I’m feeling a little undesirable,” you admitted.
“I’m Bonnie and I’m known for being honest. And I’m telling you that you’re gorgeous and very desirable,” she said with a wink.
“Thank you. I’m Y/N,” you told her.
“You’re welcome but you don’t believe me,” Bonnie observed.
“How can you tell?” you asked.
“Lucky guess,” Bonnie said.
“It’ll take more than a stranger to tell me I’m gorgeous,” you told her.
“I agree. Y/N, I have a secret to tell you. Promise you won’t run away or think I’m crazy,” Bonnie said moving closer to you.
“I won’t run away or think you’re crazy,” you breathed Bonnie’s proximity was making you a little nervous.
“See that man out there,” Bonnie said pointing to the attractive man you’d noticed earlier. You nodded yes. “his name is Damon. And he is the reason I’m talking to you,” she said. You turned to look at her and her expression was indecipherable.
“I don’t understand,” you said.
“We’re playing a game. My part in the game is to convince a woman that we agree upon to come with us to have some fun, we chose you,” Bonnie said sexily.
“Fun?” you asked.
“Yeah fun, the naked sweaty kind,” Bonnie clarified.
“is this something you and your boyfriend do often?” you asked her still unsure of the entire situation.
“He’s not my boyfriend. He’s my best friend with benefits. And no this is the first time,” Bonnie told you honestly.
“Why me?” you asked.
“You’re hot and we really didn’t need anything else. We picked you on sight. But now after talking t you I like you. And you didn’t deserve to be cheated on. You need this confidence boost and we want to give it to you,” Bonnie answered honestly.
“I don’t know what to say,” you said.
“Say yes,” she purred in your ear.
“I’ve never...with a girl, I mean,” you told her a little embarrassed.
“I hadn’t until recently. Damon and I are on a road trip and on one of our stops he convinced me to give it a try. Let’s just say I highly recommend it,” Bonnie told you her hand on your back.
“Oh,” you said nodding your understanding.
“So what’s it going to be?” Bonnie said as she slid her hand to your ass and gave a light squeeze. Your eyes grew wide.
“I’m flattered but I have to pass,” you said rushing away from her. There was no way you could do something like that no matter how tempted. Stranger sex was not something you were brave enough to try and neither was a threesome. You found an attendant to let you into the dressing room. You stood in front of the mirror looking at yourself trying to figure out what Bonnie and her friend had seen in you. You didn’t know but it did flatter you and make you stand more proud than before. To your surprise Bonnie slipped into your dressing room.
“Bonnie, what are you doing?” you asked trying to cover your scantily clad body.
“I was going to give up on you but then I thought I’d get a look at what I was passing on and I’ve decided I don’t want to give up on you,” Bonnie said.
“No means no, Bonnie,” you said firmly.
“You’re absolutely right. But can I ask you a question?” she said looking into your eyes.
“Yes, I guess,” you answered.
“Why’d you say no?” Bonnie queried.
“Why?” you asked. You hadn’t expected the question and didn’t readily have an answer.
“Yeah, why?” she asked again quirking her eyebrow.
“Because stranger sex, especially with two strangers, is not my style,” you told her.
“Neither are these panties but you’re going to give them a try,” Bonnie said holding up the pair of panties that had been her icebreaker.
“That’s different,” you said taking them from her.
“Doesn’t have to be?” Bonnie said.
“How not?” you asked.
“You’re on a quest to get your confidence back and the haircut and panties are a start…,” Bonnie began.
“How’d you know I got a haircut?” you interrupted.
“Didn’t you?” she asked.
“Yeah but how’d you know?” you asked again.
“You have the air of a woman who recently got a haircut. You touch it a lot and toss it and you don’t seem like one of those girls who toss their hair on purpose,” she explained.
“I’m not and you’re right I got a haircut this morning,” you admitted.
“And like I said those things are a start. You need positive reinforcement. Damon and I can be that for you. I’ve been cheated on before and I know how long it take to get back your confidence. I’m offering to bypass the sadness. Right now you feel like there is something wrong with you. And it colors how you feel about everything else, right?” Bonnie directed at you.
“Yes, but,” you answered.
“You know that saying the way to get over an old man is to get under a new one?” Bonnie inquired.
“Yes, so?” you responded.
“Little known fact, they mean a one night stand with a gorgeous stranger. And let’s be honest, Damon is gorgeous. Don’t tell him I said that,” she answered.
“Bonnie, I’m flattered but you’re making a mistake. I’m not the wild type. I wouldn’t know what to do in a situation like this,” you admitted honestly.
“I understand and I promise you until recently I would probably have had this exact reaction or worse. But each day is a gift and we should treat them as such. And you don’t need to worry about what to do. All you need to do is feel. Damon and I will do the rest,” Bonnie assured you. You were tempted, they were both gorgeous and you needed this, no you deserved it. You were still afraid but willing to put the fear aside, you trusted Bonnie.
“OK,” you breathed.
“OK, really? Great,” Bonnie said smiling beautifully.
“What next?” you asked.
“You finish up in here and meet us outside. Oh and before you leave put your bra and panties in your purse,” Bonnie winked as she exited the dressing room.
You exhaled deeply unsure of what you were getting into. You didn’t try on anything but you did remove your own bra and panties and placed them in the bottom of your purse. The only thing you purchased was the panties that Bonnie picked out. You exited the store to find them waiting for you. Bonnie peeked into your bag and smiled her approval of your purchase.
“Y/N, this is Damon. Damon this is Y/N,” Bonnie said handling the introductions.
“Nice to meet you,” you said extending your hand.
“It’s a pleasure to meet you,” Damon said taking your hand and brushing his lips across your knuckles. You blushed prettily and smiled.
“Thank you,” you answered.
“So Bon tells me your ex cheated on you,” Damon stated. You simply nodded. “well, he should be killed for hurting such a gorgeous creature,” he said while caressing your face. You were speechless; a simple touch form him had you spellbound. “meet us at the Pentacities Hotel,” Damon said, “room 615,” he said as he took Bonnie’s hand and strolled away.
You were surprised. You’d assumed they’d make you ride with them to assure you wouldn’t back out. They trusted you to keep your word and that trust made you not to want to let them down. You stopped in front of the expensive Pentacities Hotel and looked at the extravagant building. You reapplied your lip gloss and ran your fingers through your hair final time. As you your looked into the rear view mirror you realized you were excited. You had tried not to think about what was going to happen when you reached the hotel. But now that you were sitting in front of it images bombarded mind. The images were shocking to you to say the least. You continued to see yourself naked with their hands all over you. The image caused a physical reaction in your body and your skin began to tingle. You exited the car and entered the lobby. You couldn’t believe the posh interior. You admired it as you made your way to the elevator. You pressed the sixth floor button and took several deep breaths. When the doors slid open you stepped into the hall and followed the doors until you were standing in front of 615.
“Bonnie, our guest is in the hall; at the door actually,” Damon whispered in her ear. They were sitting on the couch in their room. Bonnie looked toward the door and smiled. “Her heart is beating fast, like a little bird,” Damon said.
“What’s she waiting for?” Bonnie wondered aloud.
“Patience, Bon,” Damon smirked and pulled her into his lap and kissed her. Bonnie responded immediately. She’d thought that she and Damon were going to pass the time fooling around but he’d wanted to wait for their guest. Bonnie straddled Damon on the couch his hands under her dress gripping her ass. The knock on the door caused them both to smile.
“I’ll get it,” Bonnie said removing herself from his lap. She moved to the door quickly her anticipation showing in her steps. She pulled the door open a wide welcoming smile on her face. “hi, Y/N! Come in,” she said as she pulled you into the room. “Damon, look who’s here,” she said as pulled you forward into the room.
“Hey Y/N. Welcome,” he said with a sexy smirk.
“Hi,” you responded. You didn’t know what to do next so you waited.
“Would you like a drink?” Bonnie asked.
“Sure,” you answered shrugging. You figured the alcohol would relax you a little.
“Damon, we’d like a drink please,” Bonnie said. You watched as Damon moved to the in room bar to make your drinks, “Y/N, have a seat,” Bonnie invited. You sat on the couch and started to cross your legs but your uneasiness about being panty less stopped you. You were sure a woman more bold than you would probably have flaunted the fact that she was without panties. You were not that woman. Damon handed you your drink his fingers grazing yours. Then he handed Bonnie hers and that included a fiery kiss. Your thighs clenched at how hot they were together. He sat beside Bonnie leaving a space open between you and her.
“She’s almost ready, Bon!” Damon whispered in Bonnie’s ear. Bonnie nodded her understanding. She smiled at you prettily. You took a sip of the drink Damon had given you. Your eyes teared up at the strength of the bronze liquid. The room was silent and to you awkward. You looked up from your glass to see that Damon had leaned over to kiss Bonnie his hand under her dress gripping her upper thigh. You wanted to look away but you didn’t because you were secretly a voyeur. Not the creepy kind who watched the unsuspecting with a telescope but you had once watched a couple in the park who thought they were alone. And since that day the idea of watching people have sex had aroused you. You heard Damon chuckle then he whispered in Bonnie’s ear again and they both turned to look at you.
Bonnie armed with the knowledge that Damon had smelled your arousal made her want to move forward. Damon got to watch at first because that was part of the fantasy. Bonnie wanted to put on a good show for him to encourage his participation. The sooner the better.
Bonnie moved closer to you. She took the drink from your hand and handed it to Damon. She brushed your hair from your face and kissed you lightly. Your eyes widened slightly. You didn’t expect her lips to be so soft. She deepened the kiss putting more pressure on your lips. She pulled away from you and sat on her knees beside you. She gripped the hem of her dress and pulled it over her head. You were surprised that she was completely naked beneath her clothes. You admired her body. Her perky breast and cafe Au lait skin. She reached for the hem of your dress and you had a mini silent panic attack. What if she got your clothes off and they changed their minds? What if she got your clothes off and they didn’t change their minds? By the time your thought was concluded Bonnie had your dress over your head and was looking at you. You tried to cover yourself but she wouldn't allow you to. She reached out and tweaked your nipple. You inhaled sharply at the touch. Bonnie smiled a deviant smile and leaned forward enveloping your nipple into her mouth, her other hand playing with the other breast. You closed your eyes enjoying the sensations.
Bonnie urged you to lie back on the couch. You did as asked one leg on the couch one on the floor. Bonnie continued the assault on your nipple but her other hand began to slide down your body. When she made contact with your clit you moaned. She began stroking your clit vigorously while now sucking the other nipple. You were being carried away and you were reveling in the feeling. Bonnie moved down your body and replaced her fingers with her mouth. She licked your clit slowly then slid her fingers into your wet pussy causing you to buck your hips. She had two fingers deep inside you pumping them in and out of your clenching hole. She inserted a third finger and began to work them deeper and harder into your pussy. You began to fuck her hand trying to get your release. Bonnie sucked your clit and fireworks burst behind your closed eyes.
She moved back up your body. You thought she was going to kiss you but before she could Damon kissed her. Your pussy clenched when you realized he was tasting you on her lips. He smirked at you when they pulled apart. He stood up and pulled you both from the couch. He pulled you to the bedroom of the suite and pushed you to the bed beside Bonnie. He got on his knees in front of you. You didn’t know what he was going to do. He smirked playfully and slid his fingers into Bonnie’s pussy. You watched his fingers slide in and out of her. Your pussy getting more and more wet. When his tongue entered you a moan of pure pleasure escaped your lips. He was relentless in his assault on your pussy. You were crying and thrashing around on the bed. Your orgasm crashed over you. When you opened your eyes Damon was holding his rock hard dick steady at your entrance.
“Tell me you want it,” he said. You were silent. You were on sensory overload; speech was beyond you.
“Tell him you want him,” Bonnie whispered in your ear.
“I want you,” you said sensually.
“What do you want?” he asked sexily.
“Tell him you want his rock hard cock deep in your juicy pussy,” Bonnie prompted in your ear.
“I want your rock hard cock deep in my juicy pussy,” you said sexily.
You had never been a person to use dirty talk but you liked the feeling it gave you. It made you feel sexy and powerful. He slid his granite dick into you and your world shifted. You were actually having sex with a stranger, two strangers. Two of the hottest strangers you’d ever seen. While Damon was sliding in and out of you Bonnie whispered in your ear again.
“Will you eat my pussy?” she purred. You turned your head to look at her. “Please,” she added.
“I...I,” you stammered turning your head away.
“I promise I taste good. I’m so wet. Please. Look,” she whispered. When you looked Bonnie was removing her fingers from her pussy. She held them up to your lips. She made eye contact with you and you darted your tongue out to take a swipe at her fingers. You were surprised at the taste and that you liked it. Bonnie kissed you then. “Will you eat my pussy, Y/N?” she asked again. You slowly nodded your head yes. Bonnie smiled and settled herself over your face. You opened your mouth and gave her pussy a pass with your tongue. Bonnie moaned and you gained confidence from her pleasure. You began to eat her out in earnest. Bonnie grinding her pussy on your face and you tongue fucking her. Bonnie leaned forward and Damon captured her lips in a fierce lip lock. He fucked you harder and deeper and you tried to take the pleasure you were feeling and make Bonnie feel it. You licked and sucked Bonnie’s sweet wet pussy, while you fucked Damon’s rock hard cock.
When you felt the beginnings of your orgasm building you began to tongue fuck Bonnie with more vigor. You wanted her to cum at the same time as you. You could feel yourself tipping over the edge being driven to some foreign place by the cock buried deep inside you. You sucked Bonnie’s clit and then slid your tongue as deep into her as you could and lapped up the juices as she came into your mouth as you climaxed on the dick inside you.
She slid from your face as Damon slid his cock from inside you. He kissed you deeply and you knew he was tasting Bonnie on your tongue. Bonnie laid on her back legs open and waiting. Damon kissed you once more then slid his still hard cock into her. She grabbed your hand and smiled prettily.
“Let me taste your sweet pussy,” Bonnie said.
You straddled Bonnie’s head and lowered yourself onto her mouth. You ground your pussy on her face as she greedily ate you. Damon’s hands were not idle as he kneaded both of your breast; playing with your nipples. Your body hummed with pleasure. He sucked each of your nipples causing your pussy to react and causing Bonnie’s tongue to go deeper. When her orgasm rocked her body she brought you along with her, your pussy gushing into her mouth.
You slid onto the bed beside her. Damon was looking at the two of you and then he winked at Bonnie and smirked. She returned the smirk and you had no idea what was happening. The next thing you knew Bonnie had lifted one of your legs and slid her pussy onto yours in a classic scissoring position. She started slowly rubbing her swollen pussy against you sensitive clit. The feeling was indescribable. You responded by sliding yourself against her a little faster until you were both rubbing your pussies and clits together furiously. You could feel Bonnie’s pussy leaking onto you mixing with your own leaking pussy and it turned you on even more. You turned your head to find Damon stroking his magnificent cock to the sight of you and Bonnie fucking. The sight made you rub yourself more vigorously against her. Bonnie responded by moaning loudly and grinding her pussy into you. You were both anxious, chasing an orgasm that was just out of reach. Your rubbing became fast and furious matching Bonnie’s movements.
Damon moved closer still stroking his cock. He was watching the two of you intently. His stroking getting faster and more intense. You and Bonnie fucked each other wildly in response to the sight of Damon. Then Damon’s climax erupted from him splashing onto you and Bonnie. The feel of his warm cum running down your body sent you spiraling over the edge into ultimate bliss, Bonnie tumbling headlong after you.
Later, it could have been seconds, minutes or hours you felt a warm rag on your body. You opened your eyes to see Bonnie and Damon cleaning you. You smiled and stretched, loving how deliciously sore you were.
“Y/N, that was great!” Bonnie said happily.
“Yeah,” you agreed smiling.
“The sight of the two of you together is something I will never forget,” Damon said with a sexy smirk, “Y/N never believe you’re not sexy. It’s a fucking lie,” Damon said before he ran his finger through your slit to gently flick your clit. You moaned low and he rubbed you a little before he kissed your forehead and stood up.
“The room is paid for until you leave. Don’t rush. Enjoy it. You earned it,” Bonnie said before she kissed you. You pulled her to you and the two of you made out; hands roaming to all of the familiar places.
“Thank you both. I’ll never forget what you did for me,” you said your voice full of gratitude.
“Bye Y/N,” Bonnie and Damon said as they left you lying naked, sore, satisfied and utterly confident in your desirability.
You couldn’t be sure but you thought you heard Bonnie giggle and tell Damon it was her turn before the door to the suite shut.