Playing Dare with Sis Part 3

I still couldn’t believe the events of the last two days. Our parents had left for the weekend because my grandma had fallen ill. They wanted my bitchy sister Kayleigh and I to spend the weekend together, much to Kayleigh’s dismay. On Friday, Vlad and I had coerced my bitchy but unbelievably sexy sister Kayleigh into a game of dare on Friday night. Over a fear of losing $100 over the game, and being fiercely competitive, Kayleigh had agreed to take her top and pants off and parade around in her underwear. She had no idea how much trouble that would get her in. Vlad took care of the rest, he started to secretly take compromising pictures of her.

From there, the game spiraled completely out of Kayleigh’s control. She tried to end the game, but at the fear of Vlad releasing those pictures to Kayleigh’s friends, she complied with our increasingly provocative dares. Of course after we got her completely naked, we started filming Kayleigh the entire night. She was absolutely stuck at this point. Even if she was now ok with the original pictures of her in her underwear being released, there was no way that she would want naked videos of her around two nerds like us being released online, her life would be ruined.

From there, we knew we had her completely under our control. I finally got to live out my long time fantasy of having sex with my sister, From blowjobs, to eating her out, to fucking her, I had my way with Kayleigh completely. I was in heaven. Of course, Vlad had his way with her as well. It shocked me how much it turned me on seeing a babe like Kayleigh being forced to have sex with a hideous guy like Vlad. It almost turned me on as much as fucking her myself.

We had our way with her all night. It was funny, at first Kayleigh seemed angry, and then she was unbelievably sad, crying openly for most of the evening while she realized how out of control the situation had gotten for her and how utterly powerless she was at this point. As the night went on, she had almost become numb to everything emotionally. She became totally compliant with everything we were asking of her. It amazed me to see my sister, who was a notorious bitch who always had to have her way, become completely powerless and accept it.

The next day, I decided that I wanted to invite my friends over and let them have their way with Kayleigh. Not only because she made their life hell throughout high school, but also to fulfil my own perverted fantasy. I figured that it turned me on so much seeing Vlad have sex with Kayleigh, that it would be unbelievably sexy to see her get gang banged by nerdy friend group.

Vlad and I invited my friends over, and to their shock, showed to them the sex object we had turned the girl of their dreams, and nightmares into. We feigned a game of dare, but quickly got Kayleigh to undress completely for them and perform sexual acts on each of them. This soon escalated to a complete gang bang, filmed of course. I was so turned on watching this, as well as taking part of course.

As the afternoon progressed and the guys had a few more drinks, I decided I wanted each guy to have Kayleigh to himself to fulfil his fantasy. I followed each one of my friends and filmed the act so that they could look back on it after the weekend was over. One of them took Kayleigh’s anal virginity in the shower, one had an oral fixation and ate her pussy out for an hour, another licked fudge off of her legs and ass before fucking her, and the last actually pretending that she was his little sister!

After a long day of fucking, my friends went home. Vlad was even so caught up in the action, that he forgot that it was his dad’s birthday! So he rushed home.

That’s when an idea hit me. As I was beginning to understand, I had a voyeur fetish, especially when it came to watching Kayleigh being forced to have sex with guys that she would normally be repulsed by. It turned me on like crazy watching her being used by Vlad and the rest of my friends.

Next I wanted to see my sexy sister forced to have sex with an older man. With Vlad’s father, Mr. Dudley’s birthday, I decided I would give him the birthday gift of a life time.

Vlad’s dad was virtually a spitting image of Vlad, but had about 30 years of terrible aging on him. He was monstrous man. He was tall at about 6’2”, but almost morbidly obese, he must have been around 300 lbs. He was completely bald except for some straggly hair at the side of his scalp. He had psoriasis plaques on his balding scalp, giving it a scaly appearance. His face was full of acne scars. His wife, Vlad’s mom, had long left him and Vlad. I always felt really bad for him actually, he seemed to have a miserable life. He was always very nice to me. He would always let Vlad and I drink at his place, and would even let us watch porn without caring.

I actually think that Vlad inherited his perversion from his dad. Being seemingly single forever, and garnering no attention from females, he was almost always watching porn, and made no attempt to hide it. He had preions to various magazines and porn sites. Since I was over at Vlad’s house a lot, I noticed that he was particularly into hot teenage girls. Nothing pedophilic of course, but he seemed to get off to the ‘barely legal’ categories on porn sites, preferring to look at the models which looked a bit younger than their stated age.

Vlad told me that he would also frequently hire cheap prostitutes to satisfy his lust. He was poor and worked a shitty job so he could never hire the types of girls he fantasized about, but it was still better than nothing he figured. I couldn’t imagine what Mr. Dudley would give to even touch a girl like Kayleigh, much less have his way completely with her.

I called Vlad with the plan, and he was equally excited. Not just for the sexual part, but he was genuinely happy to gift Kayleigh to his dad to bring some happiness into his life. After all, Mr. Dudley didn’t have much to look forward to in his life. This would be the gift of a lifetime.

I was getting hard just thinking about Kayleigh railed by Mr. Dudley. I walked to the bed room where Kayleigh was lying. She was sound asleep. She must’ve been exhausted, after all she probably had been forced to have sex 30 times that day!

That didn’t stop me though, I was horny and needed a nut. She was sleeping on her tummy. I took the covers off of her and admired her body. I couldn’t believe how delicious her voluptuous ass and toned legs looked. I stroked my hands up her long, smooth legs and thighs. She really did have the perfect body. She moaned softly, before returning to her subtle snores.

I groped her juicy ass cheeks, before mounting her. I split her ass cheeks apart before sliding my dick into her tight pussy. I started to thrust and she started to moan. I groped her large boobs as I thrusted. They felt so big and soft. She moaned louder as I started fucking her faster. She woke up half way through the sex, and the moaning stopped.

I figured that she may have been dreaming that she was having sex with some stud, but then when she woke and realized it was me her excitement waned and her repulsion returned as reality set in. I didn’t really care. I finished deep inside her.

I laid down beside her, I realized that this was actually the first time I had with her alone since the weekend started. I think she realized this too. She looked at me with her gorgeous eyes, some of the emotion was returning in them now. She had a look of feeling betrayed.

She opened her mouth “I can’t believe you’re doing this to me.” As her eyes welled up with tears.

I remained stout

“You did this to yourself sis. If you weren’t such a bitch to me in high school, there would be no way I could do this to you, no matter how irresistible this ass was.” I said as I gripped a handful of her ass and pulled her in closer to my body.

She continued to cry “I’m sorry David, I shouldn’t have bullied you and your friends like that, but this is too much.”

“Relax Kayls, I’m considering this as payment. Things will settle down when mom and dad come back. Keep doing what you’re doing, and no one will release any of these tapes.”

She nodded silently

“Good girl.” I continued “In the meantime, focus on the pleasure. Try to enjoy yourself, you’ll be happier.”

She looked at me and said nothing. I knew she probably wanted punch me in the mouth right now. She simply said nothing.

I continued “Now that that is settled, I want to tell you my plan for tomorrow.”

I video called Vlad, who was now in his room at home.

He smiled as he answered “Hey bud, and hey babe.” He jeered at Kayleigh “drop the covers babe show me those titties.”

Kayleigh cringed before sliding the covers down, exposing herself to Vlad through the phone.

“Mm that’s what I like to see babe.” He smiled

I laughed.

Him and I then worked out the plan for the night. Vlad was going to tell his dad that we had set up a blind date for him which is going to be Kayleigh. Kayleigh was going to be very friendly towards him and would do anything he asked. The thought of my hot sister Kayleigh with Vlad’s monstrously ugly Dad really turned me on. Kayleigh would of course be looking her sexiest for her date.

As a special twist, I told Kayleigh to tell Vlad’s dad that she was 16 years old. It made the story kinkier, and turned me on. I knew Mr. Dudley had a thing for barely legal girls that looked younger than 18 based on his porn habits. I figured he probably liked women even younger then legal age, if he could. The added kink of having a babe like Kayleigh being below legal age would probably be his ultimate fantasy. Kayleigh’s youthful looking face could definitely pass for younger then 18.

Vlad readily agreed to this. I told Kayleigh to get ready, I picked out a slinky black dress for her from her closet, as well as some sexy underwear. I headed out to Vlad’s, and told Kayleigh to get there for 8:00.

I went over to Vlad’s house and knocked.   His Dad answered.  He was as monstrous looking as always. I wished him a happy birthday, he invited me in happily. He was in a rather good mood today. He gleefully explained to me that Vlad had set him up with hot date. He excused himself as he went to go get ready.

Vlad and I got together, we wanted to see all of the action throughout the night, so our plan was to hide in the closet in the living room and look through the panes. We would follow them where they went and look in. Of course, Kayleigh would help facilitate us sneaking around and following them, Mr. Dudley would have no idea though.

At around 8 pm the bell rang. Kayleigh walked through the door. She looked stunning as always. She was wearing a light jacket around her dress.

She walked in and Vlad’s dad said “Hey there! I didn’t know that my date was going to be so young and stunning.” He laughed

We saw Mr. Dudley look Kayleigh up and down. She looked amazing. The jacket covered the top of the dress. But the bottom revealed a tight thin black dress which ended at her thighs just a few inches below her ass.

Mr. Dudley almost looked like he was about to salivate. He wasn’t able to hide his obvious stare at her legs. He had never seen a girl like this in person. He wondered how in the hell his son arranged this! He didn’t care at this point before talking.

“Well hello there beautiful. I didn’t know my date was going to be so young and stunning!” he laughed

Kayleigh gave a fake laugh before thanking him for the complement and wishing him a happy birthday and giving him a long hug. She went on.

“Well yeah, Vlad said you were single and it was your birthday, so I thought we could get to know each other, you know.” She smiled

“So I have to ask, how do you know Vlad?” He asked curiously. He was quite confident that his son didn’t have any girl friends, much less one this stunning!

“Oh, I know him from school Mr. Dudley, he’s a great guy,” she replied

Mr. Dudley asked nervously “So you’re done high school now, like Vlad right?”

“Well actually Mr. Dudley, I’m two grades below him,” she responded

Mr. Dudley almost started blushing “Oh erm how old are you Kayleigh?”

“Oh I’m 16 sir. But don’t worry about anything, I’m really mature for my age, I’ve never really gotten along with the immature boys at my school.” She said coyly “So that’s why when Vlad told me you were single and looking, I wanted to see if we would get along better.”

“Well erm Kayleigh, I understand what you mean but what would your parents think of this?”

“Oh they’re out of town Mr. Dudley. And after all, I’m 16 I can make decisions for myself.” She said in a seductive voice

Damn my sister was a great flirt when she wanted to be!

“Well that’s good enough for me” He laughed “why don’t you let me take your jacket for you?” He was having an internal struggle. Here was this beautiful underage girl wanting to get to know him. He was wondering if this was some sort of set up? He decided he would take things slow and see where this went.

He slipped her jacket off. He was clearly stunned at the sexy dress she had on. What she had on was more lingerie that a dress!  It was sheer black and had to thin straps around her shoulders, it was extremely low cut, pushing up her breasts. It was a dress that one of her boyfriends had gotten her, and that she had previously worn only for him. Now she was flaunting her assets in it for a disgusting old stranger!

 

Mr. Dudley was clearly ogling her assets. “My my, you’re quite, erm developed for a 16 year old.”

We noticed a bulge form in his crotch.

Kayleigh laughed “Oh Mr. Dudley, you’re making me blush. So what’s on the schedule for our date?” she asked

“Well Vlad and his friend are in their rom playing some video games, we can just hang out in the kitchen until dinner’s ready.”

“Sounds good Mr. Dudley.”

They walked past us into the Kitchen. We snuck into a different closet in the kitchen. Kayleigh saw us, and kept Mr. Dudley occupied with small talk. She continued to explain to him why she didn’t like the boys at her school, and needed a mature man. This of course, was a lie but was music to Mr. Dudley’s ears.

Mr. Dudley sat on one side of the table and Kayleigh sat on the other. “Why don’t you come on this side Kayleigh.”

She did as she was asked.   She sat down next to him.   He put his arm around her. He gradually was pushing his boundaries. He thought that there was no way that a girl who was out to trick him would let him get away with such liberties. Still, he wanted to test her slowly Kayleigh had a disgusted look on her face. He didn’t notice since he was staring down her impressive cleavage with his mouth open the whole time. 

He tried making some small talk but it was obvious he was only interested in one thing.   We watched as his rough hand moved up Kayleigh’s smooth legs. She cringed but let it happen. He reached all the way up her legs to her thong.  

He thought that there is no way that this was set up now, no decoy would allow her panties to be touched. He figured if there were no policemen barging into his door at this point, there would never be. He licked his lips, and his character changed from the befuddled and nervous next door neighbor to the sex starved pervert that he was.

He was about to reach inside her thong when the oven timer rang. He looked disappointed but he knew he had to get the chicken before it burned. He poured some wine for Kayleigh and himself.  He insisted on feeding Kayleigh. Kayleigh in turn fed him as well. We noticed him urging Kayleigh to drink more and more wine. I knew that she didn’t drink much usually. He poured the rest of glass down her throat before filling another one all the way to the brim.

“The wine is good isn’t it Kayleigh?” he cooed

“Yeah I guess sir, but I’m feeling a bit woozy.” She laughed. I knew she wasn’t acting.

“Oh that means you’re body likes it babe, have more.” He said as he poured another half glass down her throat, until she started choking a bit.

He laughed “You’re a light weight babe, but you have to drink more with me, it’s my birthday after all.”

“Ok Mr. Dudley, you’re right” she slurred

He knew what he was doing, he wanted to get her defenses down. He forced her to have another glass of wine with dinner, before taking what was left of the bottle to the living room. He led a now wobbly Kayleigh to the couch. Her cheeks were flushed. He put on a romantic movie.

We scampered back to the living room closet when Mr. Dudley excused himself to use the washroom. Vlad said that he keeps his Viagra in the bathroom, so he probably went there to take 1 or 2 pills. Kayleigh actually looked kind of scared as she’s been on enough dates to know this is when a guy makes his move. He came back to the couch. He brought his arm around her slim waist and brought her body close to him with his flabby arm. 

He put the opening of the bottle of wine on her lips and reared it back.

“Gulp it down babe, go ahead and finish the bottle.”

Kayleigh again too several gulps before choking on the cheap red wine.

Mr. Dudley thought that she was probable inebriated enough now for him to have her way with her. He was a couple glasses in now too and was no longer worried at all about having his way with this sexy jailbait teen. This was his ultimate fantasy, and now that he had some liquid courage he was thinking with his cock only.

As the movie went on he started whispering stuff in her ear. Kayleigh forced out some woozy laughs. He brought her even closer to him with his arm and let his hand rest on her breast.   Seeing that she wasn’t resisting he started squeezing her breast through the dress.

He continued to grope her breast.

“Babe tell me how old you are again.”

“Sixteen sir.” She slurred

“Mmm” he moaned “So you’re telling me these big breasts are only 16 years old?”

“Yes sir.” She complied

“And what about these legs?” he cooed as he slipped his hands again under her dress. He reached for her inner thigh and moved upwards to her sex.”

“Sixteen Mr. Dudley” She giggled

He reached her silky panties. He slipped her underwear to the side and faced no resistance. He moaned as he slid a finger into her tight pussy. She moaned. I assumed she as acting but she was drunk at this point, and her body may have been betraying her.

Next, Mr. Dudley locked lips with the beautiful teen. Her first reaction was to resist but remembering what I said she kissed him back.  He then locked lips with her and forced his tongue deep down her throat. Sensing that if he fell on top of her she might suffocate, she pushed him back on the couch and got on top of him.  They were furiously making out.   If he wasn’t so monstrously ugly I would have thought she actually was into him.  Mr. Dudley clumsily fell to the ground, causing the whole house to shake!  Kayleigh once again got on top of him and started kissing him; she was on her hands and knees with her ass in the air.  

“Mr. Dudley you’re such a good kisser.” She moaned.

He reached down her body and started squeezing her juicy ass.  

He peeled her dress up exposing her thong clad ass.   He felt her juicy cheeks for a bit. 

“Oh god what an ass babe.”

Next he slid the straps of the dress down revealing a strapless black pushup bra that made her tits look incredible!  Not knowing quite how to dispose of the rest of the dress Mr. Dudley just tore it with his brutish hands and threw it on the floor beside them.  

After kissing a bit more Mr. Dudley took his tongue out of her mouth and stood up. He lifted Kayleigh up with one hand and put her over his shoulder and walked upstairs.   I’m sure he thought he was being romantic but I couldn’t help but think of an old monstrous troll carrying a young beauty back to his lair.   We had placed Vlad’s camera in his dad’s room on the dresser and hooked it up to the big screen TV in the living room.   We turned it on and saw Mr. Dudley throw Kayleigh onto his bed.  

He licked his lips.

“I’m gonna fuck the shit out of your sixteen year old pussy babe.”

I could see that Kayleigh was scared at this point, but she did a good job covering it up. This time she didn’t have a chance to get on top as he almost fell on her.  They started making out again. Kayleigh was trying to push his gut off of her but to no avail.  He unhooked her bra and tossed it to the ground. 

 

Her big breasts were free; he licked his lips.

“Babe I watch a lot of porn, but I’ve never seen tits like this.”

He admired them for a moment before going in to feast. He sloppily toyed with her tits with his tongue before he started sucking on the nipple and ruthlessly twisting the other with his hand.   Then he put the whole tit in his mouth, it was pretty funny because it looked like her was trying to eat it.   As he was mauling Kayleigh’s tits with his mouth he slipped her thong off with his hands.   He started massaging her juicy ass cheeks at the same time.   He took off his shirt letting his full gut hang loose.   Then he took off his pants and boxers.   He had a really big dick! It was probably 12 inches, and really thick! 

“Oh god.” Kayleigh cried as she stared at his monstrous cock.

There was so much good stuff he didn’t know where to put what first!  He decided on French kissing Kayleigh’s mouth, playing with her tits with his hands and without warning and almost instinctively he thrust his cock into Kayleigh’s pussy. This made Kayleigh let out a scream that I thought would shatter the windows of the house!  She had a lot of cock in her over the weekend but none the size of Mr. Dudley’s.  

Much like Vlad, it didn’t seem like Mr. Dudley cared what Kayleigh was going through, he only cared about satisfying himself.   Now he freed his hands and mouth and placed his hands on her legs.   He was focused on fucking her as fast and hard as possible.  With each long thrust her tits would bounce, her head would hit the headboard and she would let out a moan that would echo through the house. 

The sound of her moaning was very sexy and seemed to drive Mr. Dudley to go even harder. It was incredible how long he was lasting.  Vlad explained that his Dad spent a lot of time with prostitutes so his endurance was incredible. Then something new happened.  

Kayleigh started moaning louder and louder. Her body started to writhe in a way that I hadn’t seen before. She eventually orgasmed!  Her body went limp and she had a really weird look on her face.   Mr. Dudley was still going hard. He stopped for a second and flipped Kayleigh around.  

He made her get on all fours and started fucking her doggy style.  Once again the moaning started and her tits started to bounce as he started fucking her as fast as he was before. I had to give it to Mr. Dudley, maybe he had picked up a thing from all the porn he watched, he was fucking my sister like a pro!  

He slid his hands down her stomach to her tits and grabbed her nipples.   He twisted them as he pumped her from behind.   After about ten minutes Kayleigh let out another huge moan and she orgasmed again! Her body once again went limp and her knees collapsed making her lie flat on the bed.  

 

Mr. Dudley spread her legs as wide as they would get and started fucking her more. After a few minutes he withdrew; sensing he was about to cum.  He stuck his dick in between her tits and started titty fucking her. After a few minutes he started moaning. He stuck his dick in her mouth and after about a minute of sucking he let off a huge load in my sister’s mouth. He put on his robe and instructed Kayleigh to clean up.  

We heard him coming down the stairs so we quickly turned off the TV. “Hey boys, time to go to sleep guys. ”

“Alright goodnight Dad.” “Goodnight Mr. Dudley. Happy birthday again” I smiled

“Goodnight boys.”

As we were walking upstairs I looked into the bathrrom and saw him take another pill of Viagra and smile. We didn’t get that much sleep that night, Kayleigh’s constant moaning mixed with a loud rhythmic thump kept us up. 

We woke up the next morning and went downstairs. 

Kayleigh was in the kitchen cooking and Mr. Dudley was sitting at the table reading the newspaper.   Kayleigh looked tired but still looked hot as hell. Mr. Dudley had her cooking completely naked. I couldn’t help but notice she was moving with a noticeable limp.

“Good Morning Boys. This is my girlfriend Kayleigh.” He beamed “You know her from school right Vlad?”

“You bet dad.” Vlad giggled “Looking good Kayleigh.”

“Now David, Vlad, I don’t want you to think it is weird that Kayleigh is here and naked, she’s old enough to choose who she wants to be with, trust me she likes this.”

Kayleigh couldn’t help but cringe.

I almost spit out my food laughing. This man actually thought this bombshell willingly is doing this for him.

“No judgement here pops, congrats on finding such a sexy babe!” Vlad exclaimed.

“Thanks son, why don’t you have a feel of young Kayleigh’s assets, I’m sure she wouldn’t mind, would you babe?”

“Of course not Mr. Dudley.”

Vlad didn’t need to be told twice, he soon started groping her big tits. I missed her ass too so I got up and groped her ass cheeks, moaning.

“Woah woah boys, don’t scare her off now.”

I gave her a sharp smack on the cheek.

“Oh its OK Mr. Dudley, boy will be boys, and I like the attention.” She lied.

“Oh Kayleigh, if only all young women could be like you.”

That’s when my phone rang. I picked it up, it was my Mom.

“Hey Mom”

“Hey sweetie, I have some bad news.   Grandma’s still pretty sick, so you’re Father and I feel obliged to stay here and help out around the house. It may be a couple of weeks before we’re back.”

“Oh Ok”

“Yeah, do you have somewhere to stay?”

“Um yeah we can stay at Vlad’s house.”

“Well as long as that’s okay with Mr. Dudley.”

“Oh I’m sure it is.” 

I laughed”

Ok bye sweety, and remember, in tough times like this, you and Kayleigh should spend as much time together as you can.”

“Trust me Mom, we are.”  I laughed

I returned to the kitchen and back to groping Kayleigh’s body. I could sense Mr. Dudley breathing harder now. He was getting turned on seeing his sexy jailbait slut being felt up by me and his son. He walked over.

“OK boys, me and my babe have some business to take care of upstairs. I need to pound this babe. But why don’t you two come and watch us. I think it would turn Kayleigh on, wouldn’t it girl?”

“Yes sir.” Kayleigh complied

“And maybe after papa is done you two can have a turn, would you like that babe?”

“Yes Mr. Dudley”

“Good Girl.”

He picked up the slender teen over his shoulder again and carried her up the stairs into his bedroom. Vlad had brought a high quality camera recorder and set it up at the foot of the bed. Mr. Dudley put Kayleigh down face down and pulled her ass up.

“Face the camera girl.” He commanded as Kayleigh faced directly into the recording camera

Soon the bed began to creak as Mr. Dudley’s thunderous strokes landed in Kayleigh from behind. The camera showed her face beautifully as her tits rocked back and forth recklessly. She grimaced with each blow.

Vlad and I both had our dicks out, this was such a hot scene. Kayleigh moaned in pain and pleasure as Mr. Dudley sped up.

I couldn’t believe that in two days we had Kayleigh do all of these depraved acts. After Mr. Dudley came deep inside of her. Vlad and I climbed onto the bed. Vlad put his hard dick in front of her face and she instinctively started sucking. I started fucking my sister from behind, her pussy still tight, and practically gushing with fluid.

I couldn’t believe we had 2 more weeks of having my incredibly sexy sister all to ourselves. My mind started buzzing with ideas of what I wanted to make her do next.

 

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