Playing Dare with Sis
Introduction:
This is a fictional work and all characters are above 18 years old. Themes involve a brother blackmailing his sister into sex with him and his friend. Do not read if you are not interested in this theme.
While Kayleigh and I used to get along great as children, That soon changed as Kayleigh developed through puberty. We grew apart, and furthermore, she is kind of a bitch now.  We used to get along great when we were younger but ever since she started high school she became popular because of her looks and by grade 12 she was the “Queen Bee” at our school. While she could have helped me gain popularity as well, instead she chose to bully me and my friends, often mocking us. Thankfully it was over.  It was now summer vacation and the living was easy. Â
One Friday night I had my friend Vlad Dudley over for a sleep over.  Now I don’t consider myself a looker but compared to Vlad I was Brad Pitt.  Vlad was really fat, had greasy red hair, and had glasses and bad acne. To add to that he was by far the horniest guy I’ve ever met.  My sister walked through the room as we were playing video games; she looked at Vlad with disgust, called me a loser like usual and walked upstairs to get ready for a party.  We both tilted our heads and stared at her juicy ass as it swayed from side to side with every step she took up the stairs.Â
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Vlad finally broke our gaze by saying “Damn what I would give to tap that ass.”
We both laughed and returned to the video game. About half an hour we heard Kayleigh angrily scream
“FUCK Mom you are so lame.”
We continued playing; I was used to my Mom and Kayleigh having loud arguments. My Mom talked pretty calmly so we could only hear Kayleigh’s side of the argument. She continued.
“But MOM this was going to be the party of the year!” “FUCK FUCK FUCK, okay I guess if you’re making me I have to do it then!”
A few minutes later my Mom and Dad came downstairs and said “Hey boys, we’re going to go visit grandma for the weekend because she’s gotten awfully sick, Kayleigh and David, I want you to spend all weekend together during this tough time OK?”
“Okay mom” I said
I said as they left the house. Â
Kayleigh came downstairs in a loose hoodie and sweatpants and said “Well because of you little shits, I have to stay home this weekend, I hope you’re happy.”
“Quite happy.” Vlad replied wittily.
Kayleigh responded with a glare.  She sat down on the couch and watched us play for a bit. We got bored after a while and decided to just watch TV. Vlad quickly rushed to sit right next to Kayleigh. She glared at him in disgust and moved to the next couch, I found this pretty funny. As we were watching TV I noticed that Vlad wasn’t even watching the tube, he had his eyes placed squarely on my hot sister. Even though she was wearing loose sweat pants and a hoodie I noticed that Vlad had a boner. Kayleigh either didn’t notice or didn’t care that Vlad was staring at her. I guess she was used to being stared at by guys everywhere she went. Â
“Ugh nothing’s on.” She said “I’m so fucking bored.”
I thought for a bit, “Um Sis, why don’t we play a game to pass the time.”
“Well since there’s nothing else to do what do you have in mind?”
“Dare. Like we used to when we were kids”
“Fine.” She said unenthusiastically. She thought that this might at least take her mind somewhat off of missing the party she couldn’t attend now.
The three of us sat on the floor in a triangle. I looked at Vlad, he was looking at Kayleigh and had a very menacing smile on. I knew exactly what he was thinking. Â
My sister talked “I’ll play but there are some rules, nothing that’s dangerous” then she turned directly to Vlad and said “no nudity and nothing sexual.”
He reluctantly agreed but added “let’s make it interesting, if someone wimps out on a dare they owe the darer $100.”
We all agreed on the rules and started playing. The dares started out innocent enough, whether it was making a prank phone call, or barking like a dog, or doing a silly dance. But sure enough a few dares into the game Vlad took it to the next level. He dared Kayleigh to take off her sweater.
“Perv” Kayleigh said before she took off her sweater revealing a tight white tank top that was pushed to its limits by her round tits. I went next.
“Lose the pants Kayls.”
“Eww no I’m only wearing a thong underneath”
Vlad chimed in “Well that is technically not nudity so it’s either that or you’re coughing up 100 bones”
She thought about it for a bit before saying
“Ok, but this doesn’t leave the house okay”
We nodded and she slowly slid down her sweatpants revealing a sexy white thong that fit her juicy ass wonderfully. Vlad and I were both very hard. It was Kayleigh’s turn. “I’m gonna make you pay.”
She glared at Vlad and I “I want you both to go into the bathroom and drink the toilet water like dogs.
“EWWW Fuck that” we both said. Â
But sure enough she followed us into the bathroom and watched as we drank the (thankfully unused) toilet water. Kayleigh was laughing her ass off. After we were done Vlad said
“Ok you’re gonna get it bitch. Take off your shirt.”Â
The smile on Kayleigh’s face disappeared quickly. She knew this dare was within the rules so she slowly took off her tight tank top revealing a small silky white bra that matched her thong. The bra was clearly having difficulties from keeping her perfect breasts from spilling out. Kayleigh looked in the bathroom mirror and adjusted her thong and bra so they could cover up as much as they could. This was rather futile, what she had on wasn’t meant to cover up; it was meant to look sexy. Â
Vlad and I had completely forgotten about the game, we were completely awe struck by my half naked sister.  She broke the trance by saying “Well it’s your turn loser.” I thought for a second, what could possibly make Kayleigh look better without nudity? I looked at the shower and got it.
“You’re going to love this Kayls, I want you to take a cold shower, and you have to put soap on and everything.  And me and Vlad get to watch.”
She had a look terror on her face. But she knew she had to do it. Vlad was ecstatic he was jumping up and down in excitement. Â
“I’m gonna get you back.” She said as she entered the shower and opened the curtain the whole way so that we could watch.Â
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She turned the water on, I felt it to make sure it was as cold it could be. I gave her the okay and she turned on the shower. She screamed out loud. She had goose bumps all over her beautiful body and her nipples were instantly hard. Her bra started to slip off due to the water pressure. She noticed at the last second and readjusted it and kept her hands on it (much to the disappointment of her audience). Â
She pleaded to stop but I pointed at the bar of soap. She hastily rubbed some on her chest, stomach, ass and legs and turned off the water as fast as she could. She came out shivering. Much to our delight her bra and thong were pretty much transparent and her nipples were hard. There were still white soap streaks on her chest and ass. Â
“Ok my turn” Vlad said “What the Fuck, it’s my turn!” Kayleigh said
“No you used a double dare on both of us when you made us drink the toilet water, so you miss a turn. ”Kayleigh accepted it.  We went back to the living room. Â
“I want you to get on all fours, close your eyes and open your mouth.”
Kayleigh looked confused for a second and then she figured it out and looked disgusted. “EW you gross kid, I’m not going to give you a blowjob, nothing sexual is allowed remember?”
“Who said anything about a blowjob, just do it, I promise if my dick even touches you I’ll give you a hundred dollars and stop the game.”
“Okay.” She replied, looking confused, but knowing the rules of the game. Kayleigh was saving diligently for a car, and although she knew she had already let this game get too far, she knew that she would not be doing anything sexually inappropriate. After all, she had her boundaries.
She got on all fours closed her eyes. Â
“Open your mouth real wide and stick your ass out as far as you can. Hold it for 2 minutes.”
She looked so hot, her hard nipples were clearly visible through the soaking bra and her tiny thong was engulfed by her juicy ass cheeks. Vlad and I hadn’t even seen a real girl in a bikini before and now we had a 18 year old babe presenting in front of us on all fours, dripping wet and dressed in almost nothing!
She did as Vlad said, she probably just thought horny Vlad just wanted a mental picture to masturbate to later. She was wrong. Vlad reached into his backpack and took out a small digital camera. I knew this camera well; it made no sound and no flash. Vlad used this to get pics of girls bending over or whenever an opportunity of an up skirt came up. Vlad smiled at me devilishly before walking up to Kayleigh’s ass. He gave her thong a tug, pulling the poor white string entirely into her juicy ass cheeks.
“Hey!” Kayleigh screamed
“Hey What! My hand slipped. Calm down.” Vlad laughed.
“One more slip and this game is over.” Kayleigh sneered.
If only Kayleigh knew how her ass looked. The string between her cheeks was entirely engulfed. Her pussy lips were visible. Vlad took some close up pictures of her mouthwatering near naked behind.
He smiled as he sneaked over to her front side. He walked over to Kayleigh’s mouth and whipped his cock out.  He placed his cock as close to her mouth as possible and started snapping pictures.  He motioned me to her ass and I did the same thing.Â
I took my cock out and motioned as if I was fucking her from behind. He took some pics. Then he set the camera up on a table and we both got in position making it look like we were double teaming her. We put our cocks away and hid the camera
“Ok time’s up get up” She did.
“This game is getting boring let’s stop.” Kayleigh sighed Â
“Whoa not so fast it’s my turn.” I said
“OK go loser, last round, and then I’m going to bed.”
“Take off your bra.” I tried
“Fuck you, you know the rules.” She replied
Vlad added “New rules. From now on anything goes, and only we get dares.”
“Yeah that’s really going to work; you horny twerps need to go after someone in your own league. I’m going to bed.”
”Vlad just smiled and took out his camera and showed her the pics we had. Kayleigh’s eyes widened in horror.Â
 “If you don’t do what we say we’ll send these pics to everyone you know and everybody will think you are a slut that likes to fuck us nerds, and even worse people will think you let your own brother fuck you. Do you want that to happen?”
“N-n-noo.” She said as she was tearing up “Then I suggest you do what the man asked
Kayleigh paused. She was now terrified as she knew she has no control. She looked at me, hoping I would put a stop to this. I didn’t feel any remorse. My dick was doing most of the thinking at this point. I wanted to do unspeakable things to my sexy sister. It actually felt good to have control over Kayleigh for once.
“Go ahead sis, show us those sexy titties.” I smiled
”She shakily took off her bra, releasing her perfect D cup breasts. Vlad and I were in awe. It was amazing that such a skinny girl could have such big and perfect breasts.
After a while of just staring at her breasts Vlad snapped out of it and went on to the next dare.
“I want to take off your thong with my mouth.”
“NO! I won’t let you!” she screamed
Vlad quickly snapped a few pics of her topless. “Mm we’ve watched a lot of porn Dave, but have you even seen a nicer pair of tits then the ones on this slut?”
“Stop doing that!” Kayleigh snapped
“I will if you just let us do our dares.” He said with a devilish grin on his face. “Now bend your body over that couch and let me take your thong off.“
She bent over the ledge of the sofa so that her legs were on the floor standing while her body rested on the sofa. She was crying softly.
Vlad approached her ass and put a palm on each juicy cheek. He moaned as he groped her ass. He split her butt cheeks apart and brought his face closer to her most intimate part. His hot breath sent a shiver down my sister’s spine. He then sunk his nose into her ass cheeks, before delving his head in further. Kayleigh squeamed uncomfortably. It turned me on beyond belief watching Vlad’s ugly pimple filled face delving into my sister’s hot ass.  I took the camera and flashed some more pics.Â
It was funny because Kayleigh normally wouldn’t let the most popular guy in the school touch her like this, she loved being a tease and being the one in contro. Now quite possibly the ugliest boy in the world was having his way with her! I watched as Vlad fished out her thong and slowly led it down her legs, making sure to lick every inch of flesh that was on the way. He got it all the way off and it seemed like he was going back to her ass but I stopped him
“Hey not so fast, your turn is over. ”I laughed
He seemed disappointed but realized he would have plenty more time with my Sister. Â
“Ok Kayleigh now that you are completely naked I want you to give me a lap dance, and end it with a happy ending if you know what I mean.” I said as I gave her a wink.
“EWWW No” A simple flash of the camera showing Vlad’s face in her ass was enough to whip her into shape. I leaned back on the love seat and she came over. I threw the camera to Vlad and he set it to video mode. Kayleigh stood still, Vlad barked at her “Come on slut let’s see what you got. Dance for the camera.” He laughed
Kayleigh slowly started her dance to the song Low by Flo-Ryda. She swayed her ass side to side and like a snake and a charmer my dick began to grow. She was a cheer leader throughout high school, and she was a great dancer. Her hips moved faster and she slowly started massaging my dick with her sexy ass.  She got back up and turned to face me. After some more sexy moves I decided I couldn’t take it anymore and I motioned to my cock.  Still dancing to the beat she bent down and slipped took my pants off.Â
Then she slid my boxers down and paused.  She looked up at me; she really didn’t wanna do it. I pointed to the camera as if to remind her of the consequences if she didn’t do it and slowly she lowered her mouth. She wrapped her lips around the head of my cock and slowly deep throated. It felt so good and warm.  Now Vlad zoomed in, even though neither of us had any sexual experiences before, but we both have watched plenty of porn and knew how to film this.  Being my first blowjob I came about a minute in but boy was it a big explosion.  I looked down and Kayleigh’s face and chest was covered in cum. Â
“EWW” she screamed as she raced to the bathroom to clean up. She came back good as new. Â
“Sorry I didn’t last long Sis, but I guess we can work on my endurance this weekend can’t we?”  Â
Vlad roared in laughter. Â
Kayleigh just glared, but she knew the truth, she was ours and we could do anything we want to her with the incriminating evidence we had.  She was now defeated. Vlad asked for a blowjob and this time I filmed.  He came even quicker than I did!  We had another round of blowjobs (lasting much longer this time) before we decided we needed a bit of a break. After feeling Kayleigh’s hot body up for a little bit we ordered her to make us some burgers while we played some video games.Â
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 She served us dinner in front of the TV, as she walked back to the kitchen to clean up Vlad gave her a slap on the ass as if to say good job. I laughed.  I couldn’t believe the events that had occurred this night. In a matter of hours Kayleigh went from the girl that made our lives miserable to our hot sex slave. Whereas most brothers would die of guilt doing anything close like this to their sister,  I felt no remorse. I felt that I was owed this for all of the bullying that Kayleigh and her friends delivered to me over the last few years. After all, I just wanted sex, I knew that we would never actually ruin her life by releasing the footage.
After dinner Vlad said “I don’t know about you but I’m ready to fuck this babe.”
“No please. ” Kayleigh begged“
Vlad and I looked at each other and laughed. We didn’t even respond to this preposterous request. We took Kayleigh up to her bed and instructed her to lie down on it.  Vlad said
“Since you are her bro I’ll let you do the honors, I’ll film”
“Thanks buddy.” I said
I quickly stripped down and got on top of her. I spread her legs and brought my penis close to her pussy. Â
I slowly brought my dick to her pussy and entered gently.  For all I was doing to Kayleigh I didn’t want to hurt her.Â
I thrusted in and out slowly. Â She moaned slowly, I thought she actually might be enjoying this until I looked up at her face and tears were flowing freely. Â I started going a bit faster and I started sucking on her tit. Â Right when I was about to explode I took my penis out of her pussy and exploded on her chest. Â
“Ew gross man, I don’t want your cum on the tits that I’m going to be sucking on.”
“Hey bitch be a sport and lick it off. ” He said as he smiled.
Kayleigh knew by now that whatever we said she had to do, no matter how gross it was. She nearly puked as her tongue touched the cum on her titties. Â She slowly and painfully slurped up all of the cum. Â It was so hot watching her lick my cum off her boobs, and of course it was all on film. Â
“My Turn!” Vlad said He gave Kayleigh no break or warning as he jumped on her body and started fucking her roughly.  He had no regard for her pain like I did.  She was in a lot of pain, not only from his 6inch member firing in and out of her tight pussy but from the weight of him since he weighed 220 lbs, about a hundred pounds more than her! Vlad was really gross to look at naked, he was fat and had zits on his ass, back and face, almost the complete opposite of Kayleigh who was skinny and didn’t have a single blemish on her golden tan skin.Â
Again the sight of this monstrously ugly boy fucking my insanely hot sister turned me on. He roughly grabbed her tits and bit into one making Kayleigh scream out loud.
He said “Here cause I’m a good guy I’ll make it easier for you.”
He grabbed her head by the hair and stuck his dick in her mouth before exploding. This caused my sister to gag and choke but she eventually got it down. “I don’t know about you man but I’m pooped, I’m gonna go to sleep. ” Vlad said “Yeah I’ll be right back. ” I said
Vlad ordered Kayleigh to take a shower and then come back to sleep with him. Â
I logged on to my computer and unloaded all the footage and pics on to my computer in order to make more room on the camera.  Seeing Kayleigh forced to do all of these depraved acts got me hard again. I couldn’t believe that I could do whatever I wanted with her for the next two days.
With that I walked back to the bed. Ron was fast asleep and his fat naked body was cuddling Kayleigh, much to her dismay. She was wide away. She looked at me as I approached her. I rolled Ron off of her.
Kayleigh was looking at me, terrified “Please no.” she whispered.
I didn’t say a word to her, I flipped her around on to her stomach, put my hands on her big boobs, slid my dick into her from behind, and started thrusting.
