Blackmailing younger sister
- 3 years ago
- 22
- 0
The Blackmailing Mistress free porn video
Jennifer atwood is the the former ceo of a large tech company. She enjoyed the rush that business gave but she grew bored with the office day to day. She wanted more excitement, something had to change. At 35 she decided to sell her company for billions and begin an early retirement. She took on the name miss jessa and became a very special kind of mistress...
As I scroll through the profiles I am pleased to see everything is in place. I have chosen my first targets and just staring at there pictures is making me horny. I allow my hand to wander down as I scroll.
Target 1- Elizabeth stevenson, age 21, attends arizona state college where she is the head cheerleader. She is 6'1 with pure blue eyes and long blonde hair. Her body is almost a work of art, between the six pack abs and ample tits she has the appearance of a greek goddess. I have evidence of a scam in which her and her friends gave a few handjobs to a teacher to pass a tough class. Plenty enough to get her expelled and humiliated. I also dug some things up on her boyfriend Daren, he seems to be a bit of a bully... He is the running back of the football team and they have been dating since freshman year of highschool, they are waiting till marriage for full sex but lie about it to their friends.
Target 2- Mathew stevenson, the younger brother of elizabeth, age 18, still attending his local public highschool but graduation is very soon. He only stands at 5'7, extremely overweight, both face and body acne. Due to low self-esteem he doesn't bathe and has poor hygiene/body odor. In the search of his phone I found several pictures of his impressive yet unused dick. About 10 inches long with foreskin covering the whole tip. It appears he may not be able to peel it but further info is needed. He is a shy nerd but seems to be kind from what I can tell.
Elizabeth's relationship with her brother seems to have taken a turn for the worst. From what I can tell they were close as children but as she hit highschool her attitude toward him changed. She seems to be extremely critical of his appearance and constantly reminds him he will remain a virgin forever at the rate he is going. Since she has been in college they have had little to no contact.
I was curious what Mathew masturbates too and was surprised to find it was mostly japanese doujins... It seems he feels more comfortable with 2D women. I've noticed "glory hole" is a tag he searches alot among many others. I used that in combination with a simple hack of one of his friends phone to inform him of a mistress with a glory hole better than he can believe. I had the friend also tell him the first visit is free. It took twenty minutes before he caved and set up an appointment on my website.
Elizabeth on the other hand got an anonymous text yesterday with pictures of her holding her teachers cock. The caption was a date/time and an address. The caption read"your secret can be kept, Be here on time and wear your old highschool cheer uniform."
She will definitely show up those pictures could ruin everything for her. I feel giddy as I get zipped into my black latex suit. It grips every chiseled muscle in my body, except the cut out part to show off my incredible six pack abs and just hint of the bottom of my titties.
I have bought a large warehouse a few miles from where Mathew lives with his parents. He doesn't have a car so I needed something in walking distance. The top side just looks old and dusty but I have remodeled the massive basement below. Once you are let through a secret hatch and down some stairs you arrive at big red double doors of my little club.
Inside is a lowly lit classy looking bar. All the booths are red velvet and gold. The bar itself is massive and extremely intricate. Beautiful dark stained wood with inlays and nice high backed chairs to match. I even have a dance floor and dj playing music. Behind the bar is a door that leads to many rooms I have set up for different... Party's.
I have some extremely expensive call girls on retainer and they populate the club along with a few friends I've invited to just party and dance. I want it to appear like a sexy little secret club and I think I've done a good job. I hear my phone ding with a text, it's elizabeth she is here!
I down a shot of far too expensive whiskey and hurry up stairs. As I open the hatch I see her back as she is looking around the building trying to figure out what this place is. Her fat ass is barley covered by her skimpy pale blue little outfit that she has far out grown. I whistle and she jumps at the noise.
"Right this way ma'am my mistress will be pleased to know you are here." I say this with the kindness of a professional host. I don't want her to know I am pulling the strings so I will play the part of my own assistant.
She scans me with bright blue angry eyes as she approaches. Her beautiful creamy white tits are nearly exploding out of the top of her cheer uniform. Seems someone has grown up quite a few cup sizes since highschool. It is beyond sexy so see that body squeezed so tight.
"What the fuck is this about! I don't know how they got those pictures but they... Are photoshopped... You cant just do something like this!... I will go to the police!" Oh wow somebody is feeling the heat huh? I love her anger it will make this more enjoyable. I don't show any emotion to her words.
"You are free to involve the police ma'am... Unfortunately my mistress is quite hard to track.. Impossible to track in fact... so the only result will be your expulsion for cheating... Humiliation on the internet... And a certain highschool sweetheart learning of his beautiful lovers infidelity" she is shook to her core by my words. I love seeing her realize I am speaking the truth.
"I wasn't cheating on my boyfriend!... I just.. my team... I had to pass that class to stay... On the team..." She deflates a little at the end of the statement.
"It is none of my concern I simply do as my mistress commands... We all have things we would rather not get out ma'am" I bow a little. This act should make her feel like we're in the same position, make her a little less combative with me personally.
"Now if you will follow me ma'am I have a special room reserved just for you" I extend my hand indicating she step inside the hatch.
She hesitates and opens her mouth to argue but the words catch in her throat. Rage flashes thru her eyes but she slowly walks forward and steps down into the hatch. I smile as she enters... Her descent is both literal and metaphorical.. I giggle quietly to myself.
As we enter the club I can see elizabeth blushing at the stares. For a girl who gets hungry gazes by thousands of people every weekend she is pretty sensitive huh? I lead her behind the bar and pour her and myself a shot of whiskey, she doesn't even hesitate to shoot it. I then lead her through the doors.
As we walk down the hall I hear another ding from my phone. Damn mathew is here! Of course he would be early I need to hurry this up. I open the door to her little room and lead her in.
The room is painted completely black and is big enough for a few people to stand in. The lighting is actually fairly bright On the wall is a hole with a small sign below it with a arrow pointing up "Slut hole... Enjoy!" As she realizes what this is I see fear and rage combine on her face.
"No.. no way this is disgusting!.. I've never.. sucked any dick but my boyfriend's.. let alone some stranger!" I smile as sincerely as possible.
"My mistress wishes you to give this dick the same treatment as your boyfriend actually... The blowjob from your first hawaiian vacation to be exact" I see the words hit her and she flinches.
"How do you know about... That... Video" she seems so concerned now but I don't have time to toy with her too much.
"My mistress informed me there is a one hour video of you giving a superb blowjob to your boyfriend on vacation... And as you have viewed it many times you are very aware of each step... Feel free to improve but all parts of the video should be covered at some point... Including your dirty talk" she is starting to sweat as I speak. Her rage is very evident but I know she will do it.
"If I do this... Will she.. let me go?"
"I do not know ma'am... My mistress can be very kind.. and equally cruel... It all depends on your effort and execution of the goal."
I see her mulling it over in her mind. I can see her nipples through the uniform, I bet she wanted a bra but it couldn't possibly fit with how tight everything is. She closes her eyes and breathes deep.
"Fine" is all she says.
"Very good ma'am I will fetch the stud and we can begin... Don't forget really show the effort to be rewarded" she nods as she frowns.
I leave the room and lock the door behind me. I want her to hear it lock and know there is no hope of getting away from this dick now. I love the mental aspect of being a mistress this will be glorious.
I run quickly upstairs and find mathew doing the same thing his sister was. He is pouring sweat from his walk, his shirt even has pit stains. Perfect. I walk to him and I can see is is caught off guard by my sexy chiseled body. He looks at me like I'm an alien and even looks a little scared. So damn cute.
"Young mathew I presume?" He nods slowly in awe.
"Right this way young man your milking slut awaits and she is very hungry" his cheeks turn beat red at my obscene phrasing. He has no idea how obscene tonight will get.
He follows me as if he is scared to speak. I can't blame him this must be overwhelming. I lead him down thru the club and he looks around like it's a candy store. He probably never imagined he would see so many beautiful people in one place. I pour a shot as we come behind the bar, he declines at first but after I smile at him and offer again he caves.
I escort him down the hall to his little black room. There is a hole in the wall with a sign and an arrow that says "milking sluts need nourishment"... There is a plug in the hole so elizabeth can't peek.
"Ok young man disrobe and I will put your cock into the hole... You will have a small viewing screen to watch all of the action on the other side"
"Oh wow I will?... I.. I can't believe this is real... But I'm not hard yet.. is that ok?" I smile and giggle a little.
"Well of course that's ok, that is the milking sluts job" and with that be quickly begins to disrobe. As he does I can smell him almost immediately. He already has a musk and that few mile walk didn't help. He is so fat and hairy in all the wrong places... His paleness is almost legendary. As I see his cock I remember my much needed question.
"Not to be personal young man but can you peel your foreskin?"
He looks embarrassed but still answers honestly "kind of but it can hurt... And I haven't in months"
I lick my lips in excitement. I slowly put in a small ear piece. "Ok young man I will be able to hear you if I have to enter the other room to help... So please be vocal with any concerns" he nods excitedly... He is probably surprised by how in depth my glory hole is. I have cameras all over each booth linked to my phone so I can watch both sides effectively and control all kinds of things.
"Any last minute questions?" I ask with a smirk excited to get this party started.
"Umm... Is it ok... If I cum in her mouth?" His cheeks are burning red and he seems scared to ask such a perverted question.
"Of course young man I know for a fact she loves the taste of steaming hot jizz" I wink as he looks down embarrassed.
"Now without further ado please insert your dick here.." I uncork the wall just before he pushes into it, both his dick and balls easily fit thru. The sides of the hole auto seal and tighten with soft thick rubber to ensure no sound can get thru.
He looks nervous and excited. He doesn't even notice me pull the strap from the wall to secure his head against the video viewing slot. Before he can react I already have the waist strap in place as well. They auto tighten making escape very impossible.
"Hey woah what the hell is this!"
I put my hand on his sweaty shoulder to calm him "nothing to worry young man this will enhance the pleasure, trust me"
He seems to calm a little but not much. God this is the moment. I can feel my heart racing and my tight pussy throbbing. I feel even more adrenaline than I thought possible... Retirement was really the right choice. I whisper sweetly in his ear now.
"I shouldn't tell you this but this particular girl is a virgin... She has used blowjobs to keep her boyfriend at bay for many years cuz she wants to wait till marriage... Her skills are quite something after all that practice... Are you ready to see the slut that will give you your first blowjob?"
"I... Yes.. please.." he sounds insanely nervous... And he should be.
I push the on button for his viewing screen and he doesn't react right away. Its like he can't believe what he is seeing. He then violently starts to struggle as he realizes what is happening.... but there is no escape now, only empty balls will get him that.
"Is that!.. elizabeth!!!... Ma'am you have to stop this right now!!... That's my sister!... That's not a slut it's my sister quick!"
I lean into his ear again "Oh young man it's too late now... Your sister is gonna milk every bit of your smelly cum and there is nothing that can stop it now" he is still struggling to no avail.
"What the fuck!.. no you can't that's so fucking wrong please!.. it's incest.. are you sick or something!??.. it's so fucking wrong.... You can't let her do this!!!... I love her! she is my big sister this is disgusting... please!" I see a tear falling from his eye and I quickly lick it off his face. Ahhh the taste makes me shutter.
"Oh your sister loves you too and now she is gonna show it properly... And no closing those eyes I want you to see her taste every inch.. If you stop watching I will make this little party a live stream" I bite his ear as I finish the last few words. I have no intention on doing that but I want him to get the full show.
He tries yelling and screaming but this room is sound proof nobody will hear a peep. I check my phone and see elizabeth is looking horrified at the massive sweaty cock. I can tell by her flaring nostrils she smells that sour musk from feet away. I better get over there quick to get this rolling. I see he has stopped struggling and is just incoherently begging me to stop this... Hell begging god to stop this. I love every second.
"Ok I'm gonna go help the slut peel that foreskin and feast on your smegma buffet... You be good I'll be sure to switch the cameras up so you always have the best view" I kiss him on the cheek and slam the door on the way out. I stop in the hall for a moment to laugh and rub my wet pussy. This rush is everything.... I quickly compose myself and enter the other room.
"Oh miss elizabeth he is quite excited, he wants you to start immediately" I laugh inside knowing he can hear me say that. I can here him whimpering and begging so I turn him on low for now.
"This thing is so... Disgusting... I've never seen one with.. all that.. extra skin" she looks horrified and I laugh again on the inside remembering she has only had contact with two dicks... Her professor and her boyfriend.
"Oh miss elizabeth allow me to assist, Ill teach you all the benefits of such a generous foreskin." I lightly push her forward so she is on her knees looking directly down the barrel of it. I get on my knees next to her.
"Now with foreskin this tight you have to work it a bit before it peels... So slowly jerk with one hand pointing his dick up while you make out with those dirty nuts... After a some time it should peel" She looks horrified but takes a deep breath knowing she needs to do a good job.
"Oh and please be very vocal I want to hear what you are thinking as you put that tongue to work... Feel free to talk with your mouth full" she flashes the dirtiest glare at me but slowly grips the cock.
As her tongue makes contact I turn up my ear piece... "Elizabeth please no... I haven't showered in over a week!.. please God stop this.. you are my sister you need to stop!" he is still crying a little. I smile quietly.
"Ahh this tastes disgusting!... Even worse than my boyfriends after two a day practices!... The taste is so glekkk" She gags as she tries to finish that sentence, her huge tits nearly pop out of the tight uniform. I just look at her plainly waiting for her to continue... She quickly takes the hint.
*Lick... slurp...gag... Lick... Gag... Kiss... Slurp... Gag* she has so many different tricks. Light kisses... Massive circles with her tongue... She even lightly bites the ends of his sack
The noises echo in the small room. I whisper quietly to her. "Gargle honey" she nods slightly as she is licking and takes one of his massive nuts in her mouth. She gags for a good minute and a half straight but calms herself and begins gargling extremely aggressively... In-between his whimpers I can hear mathew moan despite himself. She adeptly starts working his cock as she does all this... I'm actually a little impressed. She releases his ball with a load *pop!* And quickly starts in on the other. All those years of protecting her little pussy with blowjobs is paying off.
I can tell by her grimace and constant gags that his balls are extremely pungent. In her video she never once gagged handling her boyfriends clean little nuts. Her pretty blue eyes are cloudy with tears as his sweaty musk invades her taste and smell more than she probably thought possible.
"I have never.. gluh.. *gag*.. tasted anything so... Pleh... Gross" she can barley get the words out as she continues licking and sucking like a good girl. Oh she has no idea about gross yet.
I let her go on for 15 minutes. Poor little mathew is silent now aside from a whimper or sniffle here and there. I know he is hating himself right now for enjoying his sisters expert mouth on his nuts... Such a good boy.
"Oh I think he is ready to be peeled now... Be sure to be extremely carful it can be painful for him" I smile widely at her unsure slobbery face. She does as she is told and lowers his dick to eye level as she slowly peels.
I hear mathew start to beg and plead again to stop this... I smile knowing what is to come. As the skin pulls back on his 10 inch half hard cock a thick white and yellow gunk is revealed. I knew there would be some but I've never seen so much! It has to be half an inch thick and runs inches down this cock to the edge of the foreskin base. The smell is like a fish market with no ice buckets on a summer day. We both can't help but crinkle our noses at the smell.
"Ug what is this rancid stuff!?!"
I whisper in her ear "old smelly congealed cum left to simmer in sweat under his foreskin for months... Good milking sluts learn to love the taste.... eventually" I pat her hand in a reassuring way.
I reach into my pocket and pull out a small tooth brush... I put it into elizabeth's hand and break the bad news in a whisper again so her brother can't hear.
"The mistress specifically demanded you brush your teeth with dabs of this smelly yellow smegma smegma until atleast half of it is gone.. if you don't I'm instructed to put the smegma up your nose... I'm sorry elizabeth.. I really am" I try to sound concerned and sincere at the end. I see tears well up in her eyes as she stares at the toothbrush in disbelief. I whisper in her ear one last time..
"After you finish this part begin to suck it like your boyfriend in the video... Remember to match your enthusiasm and dirty talk word for word as closely as possible... The mistress demanded during dirty talk you should refer to the stud as big brother or big bro..... Just to enhance how obscene it sounds.. you can choose any variation of that you wish.. Now I am off to check on our happy stud here" I kiss her on the cheek and I'm out in the hall in a flash before she can respond.
I check the camera and turn up my ear piece. I see elizabeth hesitate and just stare at the smelly dick cheese.... Her eyes look vacant, I wonder if this was too much?... There will be serious punishment if she backs out of this but I do understand her fear his musk is consideredable... Hopefully she understands there is no choice though... I'm really rooting for her.
Mathew is speaking up now. "Lizzy please you don't have to do this... I love you lizzy just please stop you don't have to do it!!!!" He is screaming at the top of his lungs now. The poor boy knows she can't hear him but he keeps trying so hard... Little "lizzy" as he put it scrapes his dick with the brush getting a hefty scoop of cheese... She jams it in her mouth before she can chicken out. I finger myself a little as the hardest gag yet rocks her perfect body.
Mathew just keeps saying "oh lizzy... No... No lizzy.." over and over... He looks so distraught and sad as his sister gags over and over while continually brushing her perfect white teeth with his scum. I've never been so aroused in my life as I watch her massive tits jiggle and bounce with each gag. Spit is already glazing the tops of her considerable cleavage making her already creamy white skin gleam brighter in the light.
I switch the cameras so he can watch her tits like I am. They are truly a masterpiece and the overly tight cheer outfit is the icing on the cake. I can see his dick throb just the slightest bit for a moment when he sees them.. It was only a twitch but I know what it means... Little mathew likes his sisters sloppy tits. Very interesting indeed that will be helpful when it's time to cum... But we are quite a ways from that.
I need to get back in the room with mathew and mess with his mind a bit... I don't like how quiet and repetitive he is being I think I can do better. I take a deep breath and enter.
He is of course were I left him but considerably sweaty now. I approach and mute the volume on the tv. I rub the back of his head lovingly... I enjoy how short he is.
"Shhh mathew what seems to be the problem? My mistress was sure you would love this" I smile... I knew he wouldn't.
"Are you kidding me!?!.. you or who ever you work for is demented... I can't believe you would do this to my sister..."
"Oh mathew it's already gonna happen why not enjoy it?... Don't you find your sister attractive?" Im lightly tracing my fingers down his back tickling him a little.
"That's not the point... Of course she is... But this is fucked!.. No it's not ok to enjoy it that's my sister bitch!... What don't you get about that are you insane!?!" My smile fades now... I don't take kindly to that tone one bit.
"If you want to speak harshly like a bad boy I unfortunately have to punish you... The mistress was very specific on this... I always let the bad boy or girl choose the punishment they want" he half scoffs half whimpers.
"Choice 1- I paddle your sister 10 times.... Choice 2- I put what smegma you have left up your sisters nose.... Failing to choose will result in both punishments being carried out"
"Wait wait... I... I'm the one who should be punished.. please I didn't mean to say what I said.. please don't punish her for it!"
"I'm truly sorry my mistress was very specific... You have ten seconds to choose"
He closes his eyes in rage.. he probably feels so helpless... And so stupid for getting his sister in an even worse position than she already is. I relish the seconds as he pictures the punishments in his mind... Trying to spare his beloved sister whichever is worse.
"The... The paddle... I'm sorry for my tone ma'am... Please just... go easy on her." I smile widely again, he really is such a sweet boy. I hope he learns his lesson from this next time will be considerably worse.
"I'm sorry young mathew that's not how this works"
Mhairi
- 29.06.2022
- 11
- 0
Blackmailing Shalini Story 1
- 2 years ago
- 21
- 0
Blackmailing my old mother in law
- 2 years ago
- 32
- 0
