Sissy Blackmail
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Sissy Blackmail
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the home of sexy sissys, crossdressers and transgender girls.
There’s this married guy, Steve, who secretly meets guys via gay chat sites and he’s really attracted to a local dom master and is intrigued at the prospect of dressings a slut and submitting to him. The master eventually identifies Steve and threatens to expose his filthy secrets unless he totally submits. He tells Steve to make the necessary excuses in order to spend the weekend with his new master.
He’s expected to serve his new master 100% and so a safe word will not be necessary. Steve is terrified and shaking with fear but also, despite himself, excitement. maybe it’s just what he’s after, a stern master to whip him into shape. Someone that can satisfy his desire to be used, degraded and humiliated. Whatever happens he can’t allow his secret fetishes to become public and so one thing is certain: Steve is now owned. The night before Steve receives an email that contains an itinerary and orders for the weekend, it reads:
Prepare to submit you worthless slut. You will be spanked and punished harshly, it will hurt and you will feel it for days. I expect you to arrive dressed to arouse your master. You will wear silk or satin knickers, lace suspender belt and seamed, fully fashioned stockings. Your shoes will be patent leather with at least 4 inch stiletto heels. A short skater skirt, which just covers your knickers and a see through silky blouse – no bra I shall want to have access to your nipples – will complete your clothes. You will wear make-up with red lipstick and a short blonde wig. It is highly unlikely you will get it right first time and on inspection you will be punished for any infringement. Shall introduce you to the training bench after I have thoroughly inspected you by groping you from head to toe. You will be told to remove you knickers and hand them to me before I push you over the training bench.
I have a range of punishment implements, but I shall start with a traditional hand spanking to warm you up. You may not move or try to protect your bottom during your punishment or you will be strapped to the bench so that you cannot move. I shall raise your skirt and expose your bare bottom giving it a good squeeze and handling before I start to spank you.
I spank on alternate cheeks to give you some measure of recovery between slaps. I spank hard and you will feel every slap. After the hand spanking you will be introduced to the riding crop. This produces a short harsh sting and makes a wonderful noise as the the leather tip licks your reddened bottom. You may squeal as it continues to smart on your bottom and I shall slap the tops of your thighs down to your stocking tops – so make sure they are a good fit and come as high up your legs as possible. Once your thighs are nicely marked its time to introduce the tawse.
This is a punishment tool much loved by my Scottish teachers. It is a leather strap that has a handle at one und and a split in the leather at the other making a nice two fingered mark on your slutty bottom. It hurts , and will make you jump about and squeal. You may have to be tied down to take this punishment. It usually brings tears which only serve to make me more excited and produce a powerful erection in my cock. But we will deal with that later.
By now you will be a quivering confused mess. Your bottom is on fire but your sissy clit gives away the pleasure you have received from the spanking and I give you time to reflect on your situation. Your dressed in ladies underwear, your bottom exposed and on fire after being punished by a real man that you have only just met and you are no doubt wondering how you came to crave being treated like a submissive sissy slut. Your free to leave at any time….but we both know you won’t. What a slut you are.
No punishment is complete without the cane! I enjoy swishing it through the air to tease and intimidate a slut. You will take six good hard stokes. after each stroke you will say ‘Thank you, Sir. I am a sissy slut for your service.”
The stripes appear one after the other, your legs will shake and you will gasp and scream, but it will only spur me on and I shall only stop when you have six beautiful parallel stripes across your buttocks. perhaps I will take pity and rub some soothing cream onto your inflamed arse. Or maybe not.
You will be helped up off the bench and taken to humility corner where you will be down on your knees, hands behind your head facing the wall with your bare bottom on show. No Masters home should be without a punished slut in the corner.
After while you are communed to turn round and crawl over to me as I sit in my armchair with my legs part. The front of my dressing gown is open and you get the first sight of my cock. At all times you are to have your eyes either looking at my cock or at the floor. Never look directly at me or my guests unless you want a taste of the riding whip!
The rest of the evening will be devoted to oral training. You will be expected to develop excellent oral skills. We will start with light cock licking and slow and gentle sucking and worship. You will never touch my cock only your slutty mouth is allowed. You start by licking my cock from top to bottom and as it stiffens. I may hold it up so that your tongue can worship my heavy balls. You will take each one gently into your mouth and suck on it like a lollipop. Eventually I shall guide your mouth to my cock and your lipstick covered lips will take it in slowly , licking the bulbous end and taking it into your mouth.
You will stop licking and just hold it perfectly still on your tongue. You are just a cock rest. If I feel any movement of your tongue you will have your face slapped. How long you hold it will depend on my mood. Your signal to start sucking it agin will be me standing up and holding your sissy face between my big hands which effectively mobilise your head. Your mouth is simply my fuck hole and I start to slide my cock in and out of you and work up to a hard, rough face fucking. You will ag and choke and your saliva will cover my cock as I relentlessly pound you mouth and throat. Your gag control will be tested to the full as I hold my cock deep inside your throat.
You are my fuck toy now and you will know when I am about to cum as my cock starts to get even bigger and stiffer. I will pull my cock back a little so that I cum directly into your mouth. You will hold it there as I pump stream after stream of my Master seed into you. You will hold it with your mouth open until I allow you to swallow it all. I have cum fetish and now so do you. Clean my cock slut.
You will be allowed to freshen up and have a drink before you return to me. There is a ‘fuck stool’ that is prepared for sluts when they are not being used. It is a backless chair that has a dildo in the middle of it. You will impale your sissy cunt on that as we choose your outfit for Sunday.
This is a day of anal stretching as you are prepared for Sundays party.You will be stripped to your underwear and placed over the punishment bench. The fuck stool has done a reasonable job of widening you, but I will start with a thumb fucking, My thumb inserted deep in your sissy cunt rubs agains the sensitive spunk gland and produces a strange sensation of pleasure and the feeling of wanting to pee. You will not be surprised to know that this does not last for long a its my pleasure that counts, not yours.
The sound of a rubber glove and the relief of cool lube being squired into you and over your sissy cunt are the first indications that your going to be finger stretched. First two fingers, than three, then the fourth. The pain is exquisite as your hole relaxes to take them all. Then the thumb is introduced and a constant pressure is applied…will you get a fist inside you this first time? Never mind, there is no rush, but you know you will be fisted one day. Today you will be inserted with plugs, various sized dildos, cucumbers and whatever I decide to push up your hole. Your arse will be transformed into a welcoming wet and warm cunt for my friends. But you will not be fucked today.
Instead you will taste your masters arse frequently and you will love it. If I bend slightly, part my cheeks or point in the general direction you will start to salivate and rim me deep and wet until I stay stop. Hesitation will result in punishment – you remember yesterdays session? You will also taste masters piss. Piss to master is secondary to cum play but still enjoyable. I will piss on you at any time without warning and you will be grateful. Never shield yourself from Master’s piss, always face into it, hands behind back and mouth open. Failure to adopt this position will not be tolerated.
If you have performed satisfactorily during the day I shall allow you to kneel before me and masturbate yourself for my pleasure and amusement. Shooting your spunk into a tumbler. Then you will be milked as no doubt you will be unable to get that pathetic little cocklette stiff again. You will be placed on all fours and I shall milk you by massaging your prostate so that your cum starts to leak into the tumbler underneath you to join your first load.
I shall repeat the process until you are completely dry of spunk and your cocklette is so tender and sensitive that you can’t bear to have it touched. As a respite, you may be allowed to wank my cock into the tumbler as well and your reward for being a good sissy slut , of course , will be drink all that lovely spunk. Then back on the fuck stool, you have a busy day tomorrow.
Master has arranged a little party to celebrate his new slut. Two of my friends will be in attendance each with their own slut. These masters are your masters as well. Do as they say or punishment will be swift and severe. One of them, called Tom, is big and overweight but with a massive cock. He’s asked to break you in and be the first to fuck your cunt. I owe him a favour and so have agreed.
He’s massive and fucks really hard and will likely be on viagra so I may have to bind and gag you, better that than you embarrassing me with a safe word. he will expect you to take his cock into your mouth and get him ready to fuck you. His slut will pull your srse cheeks apart and lube your cunt while you continue to suck him. You will be grateful for the lube and stretching as he does not do foreplay but simply lines his cock up with your pussy and ploughs straight in.
Hearing you scream and watching you squirm as you are impaled on his massive cock will please his sadistic tendencies. To help you endure your savage fucking his sissy will come over and kiss and sooth you as he continues to ream your poor bottom. She knows how that monster cock feels and will lick your tears way.
When he’s finally finished with you and he’s pumped you full of his hot, sticky seed, your stretched, red raw and gaping hole will be dripping with spunk. You will take him in your mouth and clean his cock thoroughly as his slut drinks his spunk from your sissy cunt before giving you a cummy kiss and letting you taste the seed that was so deep inside you a few minutes ago.
Peter is a little easier and will be a welcome change from Tom. He will slap you about and manhandle you.he likes his sluts on a collar and lead. He is likely to want you to ride him in cowgirl position so that he can pull, pinch and play with your nipples. You will suck his cock until it’s stiff and then lower yourself onto him and ride his cock. I will be encouraging you to keep up a steady momentum with the riding crop on your sweet cheeks as they bounce up and down. You are not allowed to cum under pain of a whipping. Whenever Peter is finished with you and has shot his load into your wet dripping cunt, you will obviously take his shrinking cock into your mouth and clean him properly.
Should anyone want to fuck you or use you in any way, you will immediately make yourself available for whatever they desire to do to you.
This is Masters party and so everybody has kindly agreed to indulge my cum fetish. You will therefore be expected to eat every load of cum wherever it appears. I will also use my imagination and like to see sluts fight over my seed. you will eat it no matter what: from a mouth, out of a used condom, from a just fucked cunt, off the floor, my boots, a shot glass, wherever.
That’s what I expect of you over the coming weekends and regularly from now on, in return you’ll be allowed to keep your existing pathetic marriage and life. your safe word is ‘expose me’ and if you use it then it will happen. the concept of safe sex doesn’t exist for you, I decide who fucks you and whether they use protection, it’s none of your business. you will be bare backed multiple times this weekend and when a master blesses you with his seed I expect you to do two things: express your genuine gratitude and say thank you and mean it; secondly, you will squat over a plate and let the seed drip out, you will then lick it up nice and slow. watching this degrading act is what brings your master the most pleasure so take your time.
Lastly, your name isn’t Steve. it’s a fucking pathetic name and using or responding to it will get you punished. i will be testing you repeatedly over the weekend. your name is Suzie. I name you because you’re my property, you worthless bitch.
Steve – now Suzie – read the email and recoiled in horror. This had clearly gone too far and needed to be undone but how. Panic set in and then anxiety, Friday is tomorrow. she felt physically sick at how extreme the e-mail was. Master has some very compromising pictures that Steve/Suzie had provided, it would take 30 seconds to expose them on social media and that would be that, life over.
If she does as instructed and degrades herself then she’ll also be changed forever, full of guilt and shame from an extreme betrayal. That’s when she realised Master had already given him the solution. it wouldn’t be ‘Steve’ doing all these things, it would be Suzie. he’d live two lives with two personas, Steve the family man and sticky Suzie the cum dump. She was nervous because master could be cruel but she was also giddy with excitement at the thought of what the future held for Suzie.
Blackmailed Sissy 05/02/2022 In "Blackmail"
sounds awsome and scary too. but would love this to happen to me
such a great story i can somehow relate to steve and suzie….. makes me real horny
very hot. my clitty won’t stop straining, imagining a real Man owning me like that.
Im glad it got your sissy clit dripping and staining in your cage. Good girl xxxxx
Where ohhh where does a master like this live???demi would treat him like a master should be treated x demi x
We live among you lol xxxxxx Good girl, Demi xxxx
What a great story. Like lots of other sissy sluts I just wish that i could be Suzie..
Well you never know what the future may bring xxxxxxxx
Would love to have a master like this to train me and use like a sissy slut I am Hope we get a follow up soon x
This is just the start of her journey …more to come xxxxxx
If only I could find a master like you to treat this sissy bitch like that.
This is probably my biggest fantasy, to be harshly punished, stretched, humiliated….full trained before being put to the test by a group of Mature Dom Top Men xxx
I’m sure you would pass the test, Jodie xxxxx
Im sure you would perform well Jodie xxxxxxx
Oh fuck me! (please!) what a hot and horny story, made my cock instantly rock hard and my mouth water, being blackmailed or caught with consequences is my secret desire, thx Master Kraker xxx
It’s no longer a secret! Good girl Kerstin xxxx
Hoping for a follow-up on Suzie’s future?
If applicable, your username(s) on any sites (IWC, NF, Twitter, Reddit, etc.)
Marital Status: * Single Dating/Engaged Married Divorced/Widowed
Tell me about the filthy secrets you've been keeping from the people in your life, whether real stories or your fantasies.
Who are you keeping your secrets from? Who are they? Include their phone number and/or email.
©2022 Queen Chrissy
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