Playing Dare with Sis Part 4
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 friends. In this chapter, Kayleigh role plays that she is under age, she is in fact 18 years old, and there is no depiction of under-age sex.
Do not read if you are not interested in this theme.
Highly Recommend reading parts 1-3 prior to this chapter.
It was an unbelievable sight to behold, the perfect babe that was my teen sister was getting double teamed by the Dudleys, perhaps the most monstrous father/son duo that the western world had to offer. Mr. Dudley had his large hands around her feminine hips and was pounding away at her pussy from behind. Despite the predicament she was in, Kayleigh couldn’t help but moan softly with each blow. Of course she would have been allowed to moan louder if it wasn’t for my friend Vlad’s cock stuffed in her mouth. Over the short period of time over the past 2 days Kayleigh had become quite skilled at being able to give a deliciously orgasmic blowjob while being fucked from behind. I had just had the pleasure of getting one of these blowjobs moments earlier.
I couldn’t help but get hard again watching the sight before me. I had realized since this ordeal started that I had quite the voyeur fetish. For some reason watching my sexy sister getting used and abused by men that she would normally be repulsed by was beginning to become my real life fantasy that I loved to watch.
Making sure that it was videotaped also turned me on. We first started recording so that we would have enough blackmail material to keep Kayleigh under our control. The truth was that we now had enough blackmail material to last a life time. Despite this, I made sure each moment was recorded. There was something about recording every depraved sexual act, essentially immortalizing it, that turned me on. I even had fantasies of releasing it for the viewing of others online so that men everywhere could get off on the footage of my sister. But then of course, the only thing that was keeping Kayleigh under our control would be gone and she’d be free to leave. I couldn’t let that happen.
Vlad’s eyes quickly rolled back as he jizzed on Kayleigh’s pretty face. Mr. Dudley’s thrusting intensified. He split Kayleigh’s juicy ass cheeks apart so that his dick could get in deeper into her tight teenage pussy. Kayleigh was now moaning out loud in a mix of pain and pleasure. I pushed the tripod closer to the bed so that the high quality camera was zoomed in on her face. She had tears running down her face and was grimacing with each blow. Her eyes were mostly closed but when she opened you could tell that her eyes were rolled back. There was obviously a primitive part of her physiology that was making her enjoy this fucking.
“Uhhh uuh UHH” Mr. Dudley moaned as he thrusted harder and came.
Almost like a comic scene, his last thrust was so powerful that he thrusted the young teens body forward causing her face to slam into the camera, and actually knocked it over! The high quality camera fell to the ground and shattered. Vlad and Mr. Dudley hardly noticed. Mr. Dudley collapsed onto Kayleigh’s thin naked body practically causing the girl to suffocate!
He started playing with her hair and softly kissing her hair.
“Oh bless you, you young hot babe.” He said dreamily.
It was pretty impressive I thought to myself. For being an older guy, Mr. Dudley sure could fuck. He had fucked Kayleigh four times over the last day! Surely his Viagra pills were helping, but it was impressive nonetheless.
Our latest sex session had lasted hours. Mr. Dudley told Kayleigh to go freshen up. We all needed the break at this point.
We all watched her perfect ass in awe as Kayleigh got up and walked out of the room and into the shower. Her luscious butt bounced playfully with each stride.
“Fuck they didn’t make girls like that when I was 16..” Mr. Dudley laughed
We laughed too.
As we made our way downstairs, Vlad and I decided that we should fill Mr. Dudley in on the real situation.
We sat down.
“What’s up boys, is this about my new young girlfriend?” He asked
Vlad and I looked at each other and smiled before detailing what had really happened.
We took turns explaining that this all started just two days ago. We explained that due to pure chance, Kayleigh was made to spend time with us by my parents. We used this opportunity to play a game of dare with Kayleigh. The game started off innocent, but gradually we got Kayleigh to reluctantly undress down to her underwear. Stubbornly, she didn’t want to lose the $100 that we had bet on the game, and had no idea what our true intentions were.
I could tell Mr. Dudley was intrigued by the story.
We went on to explain how we had Kayleigh pose in provocative pictures in her bra and panties. We took pictures making it look like she was about to have sex with us. Over the fear of having these pics released online to her friends, we coerced Kayleigh further into having sex with us all night. We recorded it all, adding to our blackmail arsenal. From there we got Kayleigh to spiral further into depravity.
Mr. Dudley’s eyes lit up and urged us to continue.
Vlad explained how we fucked her all night in various ways. The next day we even invited our friends over and we had group sex with her during the day.
“Then we thought we should give you the best birthday present of all time dad.” Vlad grinned
“Well that you certainly did boys..” He chuckled
Then I chimed in with the best news. I explained that originally we thought we only had Kayleigh for the weekend. But then, my parents called saying that they were going to be away for two more weeks, so we had Kayleigh all to ourselves for even longer now!
“So sorry we lied to you Dad, guess Kayleigh didn’t want to be your girlfriend.” Vlad said sheepishly
“Fuck are you kidding me boys! What’s better than a girl friend? A hot young sex slave!” he roared “With girlfriends you have to take into account their feelings and bull shit, with her we can do whatever we want now can’t we boys.” He chuckled
“We sure can pops.” Vlad grinned
Just then Kayleigh came down the stairs. She was wearing one of Mr. Dudley’s t-shirts, practically swimming in the thing.
She looked shyly at us. Before chirping up to Mr. Dudley. For all she knew she was still putting up an act as his young girlfriend.
“I hope it’s OK I wore your shirt sir, I only have my dress here and didn’t feel like wearing it.”
Mr. Dudley grinned devilishly at her, licking his lips.
“Oh no you don’t girl.” He sneered “The boys filled me in on what’s really going on here. You’re gonna be living under my roof til your folks are home. And when you live under my roof, there are some ground rules.”
We saw a new side of Mr. Dudley coming out now. Gone was the one that feigned interest in pleasing Kayliegh as a potential girlfriend. He knew now that he had all the power and could treat her in any way he wanted.
“In case these nice boys didn’t explain it to you, you’re our property.” He said authoritatively “And there are ground rules.”
Kayleigh looked at him frightened.
He continued
“#1: I want to see that sexy teen body of yours completely naked at all times. You are to be completely nude 24/7. You will wear clothes when we allow you to. That means lose the shirt.”
Kayleigh wimpered before taking the shirt off, revealing her D cup breasts.
“Mmm, now wouldn’t wanna hide big young tits like that from daddy would you.” He smiled
He motioned her to walk up to him. He grabbed her luscious ass cheek and gave it a sharp smack.
“#2: You are to please us three, and whomever else we ask you in any way without a second thought.” He said before giving her another sharp smack “You understand?”
“Yes sir.” She whimpered
“3: For your breakfast, lunch and dinner, you are to give the three of us blow jobs and swallow the cum.” He laughed “if you need more food you will only eat what we feed you. Wouldn’t want this perfect body getting tubby now would we.”
“Y-yes sir.”
“#4: When you’re body is not being used, you are to keep the house spotless and prepare our meals”
He gave her three hard smacks on the ass
“Yes sir, certainly.”
“If you’re a good little slut and follow all the rules for the next two weeks, all of that footage stays between us 4 and you get to go back to your privileged life. Sound good babe?” He sneered
“Yes sir” Kayleigh complied.
I started getting horny watching how authoritative Mr. Dudley was being with my sister.
“Hey sis I think I got some lunch for you.” I smiled as I took my dick out. Vlad laughed before pulling his out too “Me too babe.”
We stood beside each other
Kayleigh, completely naked, crawled over on her knees. She started sucking Vlad and I off at the same time. Alternating rapidly between each shaft with her lips and hands.
Looking at her work, it was amazing how quick she learned and how good she was. I knew she was a straight A student and high school varcity athlete but I’d be damned if I didn’t think being a professional whore was her true calling.
It didn’t take long for us to deposit our loads into her. She swallowed them down just like she was told.
It occurred to me that our camera had broken earlier. Having sex with her was great, but I wanted to ensure it was all caught on tape.
“Mr. Dudley our camera broke upstairs. I think we really should try and record every minute of our time with my sister. Two weeks is gonna fly by after all.”
“Your right kid.. I got just the idea! You boys get ready. Meanwhile you missed some cum slut, you better clean it up.”
He pointed to some spunk on the ground. Kayleigh sighed softly in disgust before lowering her face down to the cement floor and licking the cum off.
“Good slut.” He cooed before giving her a demeaning smack on the ass
Vlad and I quickly threw on some shorts and t-shirts. Vlad, Mr. Dudley and I came downstairs to find Kayleigh in the nude washing some dishes.
“Here girl, toss this on.” Mr. Dudley through her some cheap looking small white robe. “One of my hookers left this here after a fuck session, figure you can wear this out.”
Kayleigh looked quizzically down at the frilly thin silky fabric before trying it on. She struggled to try and tie the straps in front of her. The only point where the front ends of the robe connected was the very point where it tied together which was around her belly button. Above this point, the robe parted so that the outer seams just managed to cover her nipples. Below the robe parted completely just below the lower edge of her pussy. From behind almost her entire ass was jutting out.
The way she looked was making me drool. It highlighted how narrow her waist was in comparison to her ass and tits. Her physique really was a miracle.
She looked down in dismay.
“A bit short huh girl. I guess that hooker didn’t have quite the tits and ass as you do. Any way no time to waste girl we’re heading out.”
He urged us to get into the car and Kayleigh followed suit. She looked incredible. Her ass cheeks and tits essentially fell out of her robe with each stride.
We got into Mr. Dudley’s Car.
He turned to Kayleigh.
“Lose the robe girl.”
Her cheeks reddened before she untied it. He commanded her to lose it all together and hand it to him.
He laid the robe out over his lap and turned the car on to drive.
Kayleigh’s cheeks were flushed red. Here she was completely naked in a car about to go for a drive in public. The car windows were lightly tinted but she could still definitely be seen.
Mr. Dudley smiled as he turned down Kayleigh’s window completely. She almost gasped in embarrassment.
“Were gonna make this ride interesting slut.” He smiled as he took his dick out and put the flaccid thing on the robe over his lap.
“You’re gonna suck my dick as I drive. When you make me cum and swallow all of my jizz, you can have your robe back. If you don’t make me cum by the time we reach our destination, you’re gonna walk out of the car with us completely naked.”
He started driving.
Realizing her predicament, Kayleigh quickly bent her body over the passenger seat and put Dr. Dudley’s big dick in her mouth. She started sucking it like her life depended on it.
The window was wide open. If someone was to look in from an even level, they wouldn’t be able to see Kayleigh as she was bent over. However, if someone looked in from a higher level they would see the sight of a lifetime; Kayleigh’s gorgeous naked body bent over to give an old disgusting geezer a blow job.
The cock slowly started to come to life with Kayleigh’s amazing cock sucking skills. She used every trick in her bag to get the thing to cum. She was licking the tip, putting his saggy balls in her mouth, alternating from slow to fast. Soon enough, Mr. Dudleys cock stiffened to the maximum, and he started moaning.
His hand instinctively grabbed her luscious hair and forced her to deep throat his cock.
Just as he was about to cum we heard a honk from beside us.
We looked over, it was two middle aged Mexican men driving a pick-up truck. They were looking directly into our cabin, amazed. Just then Mr. Dudley came all over Kayleigh’s face. The cum dribbled down to her tits.
At the sounds of honking, Kayleigh instinctively looked. The men couldn’t believe the sight that was in front of them. A gorgeous teen babe with cum dribbling down her mouth onto her naked D Cup tits. They admired the sight in front of them as we stopped at the red light.
Kayleigh was about to slump down.
“Oh no you don’t sis, give them a show.” The voyeur in me was coming out. I wanted these guys to get the show of a lifetime. “Lick the cum off you tits Kayls.”
She looked at them before lifting her right tit to her mouth and licked the cum off. We heard snaps from their smart phones.
“Holy fuck you’re one lucky dude pops!!.” They hollered
Kayleigh was in dismay. What if these guys posted the pictures online? What if it went viral? She realized that she didn’t have any control over this, and had to do as she was told.
“Show them that ass Kayls.” I ordered
Kayleigh reluctantly turned around and stuck her juicy ass out the window.
We heard the sound of several more snaps.
“My god this white girl’s ass is even better than her tits. She’s got a Latina butt!” They hollered
Just then the light went green and Mr. Dudley took off while our new friends waved us good bye.
Kayleigh was beet red, she was breathing hard and practically sweating.
Mr. Dudley threw the cum stained robe at her.
“A promise is a promise.”
Kayleigh feverishly put it back on. Thankful to now have just this thin frilly piece of fabric saving her from complete public humiliation.
We drove through the seedy part of town before reaching our destination.
Mr. Dudley parked outside of a small shop. The shop looked old and worn down. The window edges were rusted, and white metal bars were barring the windows and the door. Above the door was a neon sign reading “The Spy Store”.
Mr. Dudley motioned for us to get out of the car. All eyes were drawn to my beautiful sister as she got out of the car. She struggled to keep as much of her ass and tits covered as she could, but to no avail. Vlad snuck up behind her and lifted her robe up, giving her ass cheeks a squeeze.
“Fuck I could grope this ass forever.” He moaned
Kayleigh was exposed in public for the first time, her cheeks were beet red. I looked down the street, it was fairly empty but there were a few homeless men further down the street. I heard them yelling over to each other as their attention drew to the young hot teen being groped in public.
“Come now boys, we don’t want to cause too much of a scene now.” Mr. Dudley sneered.
Kayleigh quickly tugged the her robe back down covering as much of her ass as possible.
Mr. Dudley then led us inside the store to do some much needed shopping.
