Blackmailing Bitch Sisterbysilkstockingslover©
Summary: A nerdy brother blackmails his slutty bitch twin sister.
Note 1: This is a summer 2012 contest story so please vote.
Note 2: Thanks to KatieKay, MAB7991 and Bill for copy-editing and LaRascasse for his plot suggestions.
BLACKMAILING BITCH SISTER
1. CATCHING MY SISTER IN THE ACT
I have always hated my sister...always.
Even back when we were just five years old I hated her. We were both getting ready for the first day of kindergarten and she was already playing the diva persona that she would come to exemplify in the years that followed. I was wearing my favorite Mutant Ninja Turtle t-shirt and Brittany with a big smile on her face, threw the last half of her chocolate milk on me. I was shocked and started crying. To make matters worse, when Mom came in to see what had happened Brittany lied and said I spilt it on myself...and of course Mom believed her. It was this and a trillion other similar trivial but mean moments that was the life of me...the nerdy twin of the fabulous Brittany: cheerleader, prom queen and utter bitch.
While high school was the bane of my existence it was the peak for my sister...she would probably marry the football star, have babies and never leave this god-awful small town. For me, on the other hand, the road ahead was filled with promise and in six weeks I would be off to Princeton on full scholarship...away from my bitch sister who was not only the school diva but who could also do no wrong in the eyes of my doting parents, who had never lived anywhere other than here as well...high school sweethearts who married and lived happily ever after with their two kids, white picket fence, blah, blah, blah.... They could never understand what they called my 'fixation to nowhere'. They couldn't understand why anyone would want to leave the small utopia of Paradise Valley, a very deceiving name if ever there was one.
Regardless, I was just biding my time until I could leave and find real paradise, which I believed was anyplace but here, when opportunity fell on my lap.
My parents were gone to a wedding for the weekend and I was supposed to be going to a buddy's for the weekend (I may have been a nerd...but nerds stick together) when I happened to come home Saturday afternoon and caught my sister in the act. This wouldn't have been a big deal, Brittany was eighteen and had been dating Lucas for two years. They obviously fucked and according to the rumors, a lot. But what made it a big deal was it wasn't Lucas, nor was it a guy, nor was it someone her age.
I heard moans coming from my parent's room, which was odd as well, and before moving further double-checked that my parents' car wasn't in the driveway (their plans could have changed like mine did when Elmer got a bout of the flu...ending our Star Wars marathon only partway through the second movie. My parents' car was not in the driveway. Although a couple doors down, there was a blue Ford Focus I had never seen before.
Curious, I quietly moved up the stairs and I heard a female voice I didn't completely recognize at first although it was vaguely familiar. "Oh, yes, eat my cunt, Brittany."
I stopped, frozen in my tracks. Brittany was with a girl? Now a morally upright brother may have turned and walked out, but, for many reasons, that is not what I did. I was a virgin; other than on the Internet, I had never seen a girl naked. Christ, I was even too shy to buy some adult magazine at a convenience store. But an open door and the promise of lesbian sex and the curiosity of who my sister was seemingly pleasing was impossible to ignore. Realizing the great revenge opportunity as well, I pulled out my phone, turned it onto video and pressed the record button.
I crept forward, my heart full of trepidation, petrified of being heard as the naughty talk continued. "That's it baby, keep licking me. You are such an eager little cunt-licker, aren't you?"
I was just outside the door when I heard my diva sister, whom everyone falls over their feet for, reply, "Thank you ma'am, I love pleasing you."
I couldn't believe what I was hearing and a second later I couldn't believe what I was seeing. My sister was between the nylon legs of someone I couldn't see, my sister's picture perfect ass staring directly at me. The unknown woman moaned, "I know you do my dear, you are a natural-born pussy-pleaser."
At hearing the phrase 'my dear', I held in a gasp as I realized who was on my parents' bed, legs spread open and being pleasured by my bitch sister. It was Mrs. Charles our drop-dead gorgeous English teacher. She was in her forties, but I imagine as many teenagers stroked themselves at night to her as they did to my popular cheerleading bitch sister.
Mrs. Charles was a blonde haired, blue eyed goddess who always wore skirts or dresses, always wore three inch or higher heels and always had her legs wrapped in a pair of pantyhose. Although she didn't dress like a slut like my sister did, her breasts were just as ample and showcased slyly by her various blouses. I can't even begin to count the number of loads I have shot thinking of Mrs. Charles' big breasts and to-die-for legs.
The main difference between my voluptuous English teacher and my equally voluptuous bitch sister was that Mrs. Charles was nice. She was a caring, compassionate, sincere and intelligent woman who was my main reference for my Princeton application and my educational idol (both academically and fantasy).
I couldn't fathom in a million years how she ended up on my parents' bed being pleasured and seemingly in control of my bitch sister...who always...I mean fucking always...was in control. It was a mystery as unexplainable to me as the Bermuda Triangle...or how to speak to a girl.
I was brought back to the crazy reality as Mrs. Charles moaned, "I'm close my dear, finger-fuck my cunt, my slut."
Hearing a teacher call my sister a slut was shocking and yet hot as hell. I only wished I could see her face as she was brought to orgasm. I recorded, my cock a missile in my pants, my ex-teacher's orgasm.
"Oh yes, yes, Brittany, suck my clit, get me off, oh yes, fuuuuuck, you dirty fucking sluuuuuut," my Princeton scholar teacher mumbled incoherently as my sister brought her to orgasm.
My sister remained between Mrs. Charles legs for a couple of minutes while our ex-teacher recovered from her orgasm.
I stared at my naked sister from behind and although I had never considered her sexually...she was just my bitch sister... I was suddenly having thoughts of what I would like to do with her.
"Ready to be fucked?" Mrs. Charles asked, still breathing heavily, as she sat up and I quickly moved away from the door.
"Fuck yes," my sister replied, in a tone of desperate hunger I had not heard from her before.
"Grab the strap-on, my dear."
Peeking around the corner cautiously, I watched my sister go to a bag on the floor and pull out a big black strap-on. She handed it to a now standing Mrs. Charles whose big breasts were staring at me. My sister wordlessly wrapped the harness around our teacher's waist.
Once the strap-on was on, Mrs. Charles said, "On all fours, my little cheerleader pet."
Brittany quickly got back on our parents' bed, clearly eager to get fucked by a plastic cock.
"You are such an eager little slut, aren't you," Mrs. Charles asked.
"I'll always be your slut, Ma'am," my sister answered, so unlike her usual in-control demeanor.
Mrs. Charles looked delicious in only thigh high stockings and a cock wrapped around her waist. I wondered if she wore thigh high stockings under her conservative teacher attire all those days she taught me. I was dying to know how my despicable sister and my favorite teacher ended up as sex partners...it just seemed too preposterous to be true and if I hadn't been seeing and taping it, with my own eyes, I would never believe it.
Mrs. Charles joined my sister on the bed and seemed to be teasing my sister. From my viewpoint, I got a great side view and could see that the plastic cock was still not in my sister.
"Please just fuck me," my sister moaned, the teasing clearly driving her nuts. Watching her begging and not in control was easily the greatest moment ever.
"Beg, my slut," Mrs. Charles demanded, making the hot scene even hotter.
My sister, giving in like some cheap slut, begged, "Oh fuck, please fill my cunt with that big cock of yours."
Mrs. Charles obliged and thrust forward, the entire cock disappearing inside my sister.
Brittany screamed, "Oh fuck, yes, fuck your slut, fuck my cunt."
Moaning, dirty talk and hardcore lesbian fucking continued as the sister I despised and the teacher I idolized went at it hardcore, way better than any of the hundreds of porn videos I had watched online. I began rubbing my cock through my jeans as I continued filming the shocking scene, the greatest moment of my young life. A million ideas of how to blackmail my bitch sister were already spinning in my head as my cock begged for relief.
I don't know how long Mrs. Charles fucked Brittany; five minutes, maybe ten, fifteen for all I know as I just continued rubbing myself and filming before Brittany screamed, desperately, "May I come Mommy?"
"Always with the Mommy," Mrs. Charles replied with a chuckle, "If I didn't know better I would think you want to be your Mommy's little pet slut too."
"Oooooooh please, Mommy, can I come," Brittany whimpered, begging like a dog.
"Fuck yourself to orgasm, my cheerleading slut," Mrs. Charles ordered.
Brittany moaned, "Thaaaaaanked yoooooooou," as she began bouncing back hard onto Mrs. Charles plastic cock.
"Fuck you are such a horny little minx," Mrs. Charles assessed, slapping my sister's ass.
"Oh God, oh God, oh God, fuck, yes, yes, fuck, oooooooooooooooh, God, I'm commmmmmmmmmmming," my sister screamed as we both reached orgasm at the same time, as I coated my underwear with my cum simultaneously as Brittany's juices flooded out of her. Brittany fell forward and Mrs. Charles returned to fucking Brittany.
"Keep coming, slut," Mrs. Charles ordered, as she pumped the plastic cock in and out of my sister's still leaking cunt.
A minute later Brittany begged, "Please stop, I can't take it anymore."
Mrs. Charles pulled the cock out and said, "Clean up my toy, slut."
Brittany, her face red with joy, quickly obeyed, bobbing up and down on the plastic cock licking her own cum. I knew then and there I was going to make her suck my cock. I didn't care that she was my sister....I was going to make her my fucktoy....
I kept recording until she took the cock out of her mouth. Then, I quietly went back down the stairs and out of the house as I prepared my blackmail plan.
2. MANIPULATING MY TEACHER
While I waited down the street, I emailed the video to my account. It was about fifteen minutes before Mrs. Charles came out of my house, her bag of toys over her shoulder. Timing it perfectly, I started walking so that we would meet at the end of my sidewalk.
"Hi, Mrs. Charles," I greeted, startling her.
Her face went red instantly and she stammered, "H-h-h-h-hi Samuel."
"What brings you by my humble home in the middle of summer?" I asked, having fun with my rattled teacher.
I had to give her credit, she was quick. "Oh, I was just hoping to catch your Mom to sign some papers for your scholarship."
"Oh, well she should be back Monday. I'll tell her you stopped by."
"Thanks, Samuel, that would be great," she replied, seemingly a bit relieved.
Knowing her dirty secret somehow gave me a confidence I never had before. "Mrs. Charles, you look very nice."
"Thanks, Samuel," she replied, like she would a child, underestimating me like so many others had done my whole life.
Thinking she was safe, she started walking to her car. A little offended by not being taken as a man, I said, "Mrs. Charles, I love your legs in thigh high stockings."
She froze in her tracks. "Pardon."
"You are wearing thigh high stockings, are you not?" I asked, smiling.
"Why do you think that?" she asked, her worried look back on her face.
"Just a hunch. A sexy woman like you would not wear pantyhose," I smugly said, a suaveness in me I didn't know existed.
"Samuel, what has gotten into you?" she asked, surprised by my aggressiveness.
"Not what was just in my sister," I said, revealing all I knew.
There was a long silence before she gasped, her face instantly going as white as a Ghost's, "Oh my God,"
"Funny, that's what Brittany kept saying when you were fucking her," I quipped.
"Oh Samuel, I can't believe you saw that," she was clearly mortified at being caught.
"Actually, I recorded it," I revealed, piling on the dirt.
"You didn't!" she gasped.
"Would I lie to you, Mrs. Charles?" I asked, moving closer to her.
Frantic, she begged, "Samuel, please don't...I would be ruined."
"I have to ask, Mrs. Charles, how did you and my sister end up fucking?" I asked, purposely being crude, trying to take control of the situation.
"Samuel!" she gasped, clearly surprised by my uncharacteristic behaviour.
"Mommy," I countered, repeating Brittany's words during intimacy.
"Please, Samuel," my teacher pleaded.
"I like a girl who begs," I smiled, before going in for the kill. "What are you willing to do to keep your little secret between just the three of us?"
"Samuel!" she said my name again. "What're you implying?"
"I think you know very well what I'm implying," I countered. My beautiful teacher remained silent until I added, "I want you to suck my cock like Brittany sucked yours."
Her face was now sinfully red as she whispered, "And you will delete the video then."
I lied. "Of course, Mrs. Charles." Although I was already thinking of how I was going to tape her blowing me.
She was trying to figure out how to deal with my offer. I suggested, "The garage."
"Now?" she asked, surprised.
"No time like the present," I shrugged.
She looked around and sighed, "Ok, let's go."
Even though I came only twenty minutes ago, give or take, I was rearing to go again. I led her to our garage and she followed as I slyly pulled my phone out of my pocket and into my hand.
Once in the garage, I closed the door and was surprised when she immediately fell to her knees.
Again quoting the scene I had witnessed earlier today, I said, "You are such an eager little slut, aren't you?"
She looked up to me with an angry look, clearly offended at being called a slut, but she undone I belt and pulled my pants down.
My sticky wetness on my underwear was obvious, I apologized. "Sorry, Mrs. Charles, watching you fuck my sister made me shoot my first wad."
A slight smile crossed her lips as she fished my cock out of my underwear. Although I am nerdy looking, pretty scrawny and still with acne, I was relatively well equipped, a solid eight and a third inches erect (I know, nerdy, but I measured). Her reserved behaviour seemed to fade as she held my cock in her hand. She looked up at me and complimented, "What a nice cock you have Samuel."
"Well, you are the first to ever see it," I admitted.
"If the high school girls knew what you were packing you would have to beat them off with a stick," she said, slowly stroking my cock.
"That I find hard to believe. I don't throw a football or bounce a basketball."
"That may be true," she said, licking my cockhead. "But most girls can't resist a nice big cock and you have a nice big cock." She opened her mouth and leaned forward engulfing it.
I let out a whimper, the feeling of having lips wrapped around my cock a sensation way greater than my wildest fantasies. My teacher took her time, slowly moving back and forth as I awkwardly clicked the record button on my camera and moved my hand to my side to get a great side view. I was thankful I had come recently or I would have shot my load in seconds. I watched in awe as my favorite teacher, my idol, sucked my cock.
After a few minutes of slow sucking, she surprised me and asked, "Did you ever masturbate about me sucking your cock, Samuel?"
"Yes," I moaned, her tongue swirling around my mushroom top.
"Of fucking me on my desk?" she questioned, pushing my buttons.
"God, yes," I admitted.
"How about me being your personal fucktoy?" she continued, before returning to my cock and deep throating me. Amazingly, she held my cock deep in her mouth for a few seconds, causing me to shiver with pleasure.
My pretty teacher allowed my cock to slip out of her mouth. Looking up at me she surprised me when she demanded, "Call me a slut!" she wrapped her lips back around my cockhead and pulled back, treating it like a lollipop. A loud 'pop' sound was released as she relinquished the suction on my cock.
"You slut," I whimpered, so in awe of my first blow job.
"You can do better than that, Samuel," she teased, again stroking my cock. "Make me your slut, baby."
Being called 'baby' turned me on even more, making me to come. I said, grabbing her head and pulling her to me, "Suck my cock my slut teacher. I am going to fill your cocksucking mouth with my cum like the cheap teacher whore you are."
She moaned, clearly turned on by the belittlement, as she began to furiously bob back and forth on my cock.
"Faster, slut," I demanded.
She obliged and I continued to talk nasty to her. "I bet you want my big cock in your cunt, don't you, slut?"
More moans as she continued devouring my cock.
"And feel my hot seed filling your slutty cunt," I added.
Her head was moving faster and faster, continually taking all eight plus inches in her mouth. Unable to last any longer, I grunted, "I'm coming teacher slut. Swallow every drop of my cum or else."
She didn't slow down as I exploded my cum in my favorite teacher's mouth. I couldn't believe how amazing my orgasm felt, unlike any that I had done while on my own. After my balls were emptied, Mrs. Charles slowed down and eventually allowed my still-hard cock to slip out of her mouth.
She stayed on her knees, looked up from her submissive position and asked with a sexy smile, "Was it all you thought it would be?"
She noticed the phone and smiled, "You are quite the bastard."
"You are quite the slut."
Standing up, she leaned forward and kissed me. Funny, I just realized I got my first blow job before I got my first kiss. Her lips were soft and when she broke it a minute later she said, "Can I assume you will keep your sister and I and you and I a secret?"
"I am not sure that was grammatically correct, Mrs. Charles," I teased.
"You brat," she said, slapping me playfully.
"I never planned to use it against you," I admitted.
Looking at her watch, she said, "Shit, I am late."
"I still want to know how you and Brittany ended up together," I said.
She squeezed my cock and smiled, "Another time, stud."
She turned to leave and I took a risk and said, "Slut, stop."
Thankfully, she did. She turned around with an unreadable look on her face.
"Give me your cell number," I demanded.
"Why is that?" she asked, demurely.
"I plan to fuck you like you desperately want me to," I said, with a confidence in me I didn't know existed.
"You do, do you?" she asked, pulling out a pen from her purse.
"Oh yes, Mrs. Charles. I plan to use you as my slut all summer," I promised, my head spinning with the potential.
She handed me her number and said, "By the way, stud, it is no longer Mrs."
"You're divorced?" I asked, surprised.
"Been separated from him since January, but it's not something I would announce to my students," she said.
She gave my cock one last squeeze. "Oh yes, I'll be gone for the rest of the weekend, going to the country Jamboree with Mrs. Waters and Ms. Houston."