The Anonymous Blackmailer Ch. 06

The Anonymous Blackmailer Ch 6

Dommed if I don’t, pt 1: it all comes to a head. But whose?

© 2024, all rights reserved to the author Flynn99

[Terry and Eve have discovered that someone on the internet is blackmailing both of them and, so far, has used that power to cause them to perform sex acts in public. Eve has been forced to display herself provocatively at work. And Terry was forced into a scene with a dominatrix which the blackmailer had arranged, but who also was training him on how to do D/S scenes while she’s made him submit. Eve was forced to perform naked, and humiliate herself at a strip club in front of Terry and the entire audience. They are Both terrified about what’s coming next, while intensely worried about who’s blackmailing them, why and what will become of them.]

*Saturday*

I thought Tuesday and Wednesdayy were brutal, but today… My life is ending.

I’m staring at the text in disbelief: IT has ordered me to tie Sandy in a chair with bondage gear tonight and fuck Eve in front of her. Sandy is the one redeeming bit of my life from before this ordeal: the love I was going to take to my grave.

And now IT is going to destroy that too.

IT is our blackmailer: Eve and I are being blackmailed to do dangerous, sexual things. We call the blackmailer ‘IT’ since that dehumanizes the scumbag. Not a he, not a she, but a thing.

I am to rearrange the house survey cameras around the living room to catch all the details from every angle. The chair Sandy will be in. The door Eve will be coming through. The couch and chair where I am to dominate and fuck her. Everything exactly in its place. IT tells me to bring lights from my studio to place in different positions around the room… But only after Sandy is tied and blindfolded. IT has access to my cameras. And computers. Andcellphone.

And I’m convinced IT’s in my brain.

Maybe IT is a creepy porn production site? Maybe the whole point of this is to make an amateur porn video that’s hyper-realistic: because it’s real.

No, calm down. That’s an overactive imagination talking. It’s not going there, I assure myself. But will there ever be an end?

A malevolent AI? A secret society? That’s the stuff of science fiction. An alter-ego Jekyll-Hyde personality I’ve expressed from myself?

Some sick fuck who’s getting his rocks off by doing this to us. Some hyper-dominant personality? Could it be Mistress Kara? She had secret-society tattoos, didn’t she?

And why (oh, why) do I have to drag Sandy into this?

I beg IT to leave her out of it. But I only get pictures in reply which were taken out of the footage from the security camera in my living room. Pictures like her fucking me cowgirl, her breasts suspended in midair as she was on a downstroke and with an adorable goofy face caught in the millionsecond of that frame. A picture of her fondling her nipples, password in her eyes, as I was going down on her. Then another, later that session, her back arched, her arms holding the back of the couch as she came, a look of ecstasy encompassing her face. Picture after picture. Half of these were taken before I even knew about IT – already too late by the time I found out.

“she already is involved up to her tits u cant stop this “

“figur out how to jus go wit it “

So, yeah, apparently, I have no choice.

I was trained by ITs diabolic machinations, day-before-yesterday, as a dom. But Sandy has no idea.

IT showed me her tastes after hacking her account on my computer. She likes the fantasy where a lover is cuckqueaned. Sandy, my girlfriend, has never admitted that to me. Nothing. I thought she was straight-and-narrow.

She has no idea I’m anything but vanilla either, despite always having been kindled in my head. I’m now ashamed to admit that we never talked about it. Neither of us. I guess we each were afraid of what the other person might think. But tonight, best case: it might – just might – be a nice adventure: a turning point in our journey to understand each other more deeply.

Or, worst case: it might be just fantasy for her, but nothing she would ever, ever want to do in real life and she’ll get pissed and leave me forever.

I feel terrified and awful. Yes, I’ve been cheating with Eve. Is it ‘cheating’ when someone makes you do it? I don’t know, but I did it and Sandy doesn’t know, so it feels like cheating.

It feels like cheating no matter what.

And Eve… I think I have feelings for her. I realize, happy, they don’t change my feelings for Sandy. I just have something completely different with Eve. But probably only until this blackmail ends, however it ends.

How will this blackmail end? I’m inured to that question by now. My future is not in my hands. IT has all the cards. I can’t do anything now except roll with it. So, damn it all, I’m going to roll.

Which first means screwing my head on straight. If I’m the dominant tonight, I’ve damn well got to act like a dominant. In that headspace, Sandy will be my sub and Eve is my other sub. Maybe Sandy could be the alpha sub? Would that help?

I’m introducing them and Sandy is just going to have to understand that that’s the way it is – I have another – at least for this scene. It won’t be Sandy’s fantasy if I don’t make it feel real and to do that, it just has to be real.

I spend the morning watching videos and practicing in my head. Watching Sandy’s favorites again, three times each, helps, then I pull a few of my own. I open Literotica and read a couple stories while playing that rich guy BDSM movie that Sandy liked in the background. I’ve got to get the technique and the mien – the assertive confidence – down. There’s no turningback anymore, so I have to make the go-forward work.

I smoke the terror I feel into a little box in my head, bind it with shipping tape and discard it in the back of my skull.

Having spent Thursday submitting, it’s a hard transition to go from my first subspace one day to – is it a word? – domspace the next.

In the afternoon, I go out to lunch, then to the studio to collect stuff. I get home and set to wrapping packages, again taming my nervousness. I am a dominant. I am in control!

I rehearse the possible options of the many ways that tonight might go. Sandy will be here at five. Eve will be here at seven. I remove the damn cock cage and happily, hear no correction from IT.

I make a nice firecracker shrimp dinner – one of Sandy’s favorites – with basmati rice and sauteed veggies, but I make enough so that there will be plenty of leftovers if Eve, somehow, has an opportunity to eat, too.

It’s five fifteen and Sandy is late. Damn, why tonight of allnights? I pull out my cellphone to text her but just then, the door opens.

“Hi, Daddy! I’ve missed you!” She runs into my arms and give me a big kiss and I kiss back. This may be my last kiss with the old Sandy, so I savor it. It may even be my last night with Sandy at all. I catch my heart as it’s about to fall in my stomach, check that thought and put my heart back where it belongs.

“Baby, I love you. God, how I love you!”

She smiles and melts against me in her arms when I say that, and just hugs me.

“I made dinner – will you serve while I pour the champion?”

“Champagne? Are we celebrating?”

I look at her knowingly. “Yes, dear. Now be a good girl and serve, please.”

I get a little quizzical Look from her as she pauses for a moment, then a quirky smile as she goes to the kitchen. I smile back confidently and wink. Dom Terry loves what’s going to happen. Old Terry is still nervous.

She tells me about her day and apologizes for being late… and we sit and I toast.

“To my darling Sandy. Above all, know that I want you. It’s been a weird few days for me but out of all of that, what I’ve learned most is how much you mean to me.”

She smiles sweetly, inclining her head a bit showing curiosity at my comment, and we drink.

She smiles and, looking into my eyes, take a bit, then looks apparently at the food. “Mmmmm… fuck, but this is good! My favorite! There’s a bunch of food there – are we expecting company tonight?”

I smile enigmatically, “Maybe…” Yes, definitely.

We chat amicably through the entrée. It is a really nice conversation. And it relaxes me.

“So, what’s on the dessert menu tonight?”

“You are, my love. In oh, so many ways.” I snicker at my private joke.

“Mmmm… I can get behind that. I could use a good lay tonight. It’s been almost two weeks, Terry! No pressure…” She smiles coquettishly.

“Ohhhh… you’re getting fucked. And so am I.” I don’t know ifmy smile came off: I was trying for wry, but there may have been some wistfulness in it.

“Ohhh, Daddy! You going to put that big cock in me tonight?”

Again! How could I have missed this in her? She really has been hinting to me about her submissive kink for months. I just thought it was silly talk!

“I’m putting that cock somewhere. But it’s not yours to question… be a good girl and clean up the table.” Her eyes go wide at that. First time I’ve ever commanded her. Tonight’s the first night I’ve used the ‘good girl’ trigger phrase. Now the game begins. How will she react?

She smiles and cocks her head. She’s definitely thinking about this and trying to catch up to what I’m putting down. But I see that cute little grin on her face and she replies, “yes, Master” as if it were a joke… but maybe not. Then she starts to clear the table.

“I like that. You can call me ‘Master’ all night.” Her breath catches in her throat and she looks over her shoulder at me and smiles. “You’ll be my good girl and do what I say, right?”

“Yes… Master.” She giggles. “I’m always your good girl. I like this game.”

“Did I say it’s a game?”

“No, Master, you didn’t.” She looks over her shoulder at me again to try to figure out what’s happening and I smile and wink. “It’s kinda hot.”

Damn. There it is. Why didn’t I pick up on this before?

“Good girl, now finish your champione. I have a gift for you.” I go to the other room and retrieve it, returning to Sandy who’s now sitting demurely on the couch. I take a moment to appreciate this scene: committing it to memory as if for a painting. She’s petite, nicely built – exactly my type. Her brownish-red hair is perfect, flowing. Her makeup is impossible. Her short black pencil skirt with stockings or panty hose underneath, scream ‘fuck me.’ Her silver silk blouse, strategically unbuttoned, screams ‘us too!’

I hand her the present and sit next to her on the couch. The moment of truth./p>

“You’ve rearranged the living room. Oh, this is for me? Thank you… uh, Master… I love that you thought of me.”

You might not when you open it, I think, sardonically. She starts tearing the paper and opens the box. Genuine surprise in her eyes. After a moment to digest what she sees, she looks up at me with bedroom eyes and says, “oohhhh…” she breathes deeply. “I… I’m surprised but. Wow, I love them. Master.” Her breath shakes as she says Master and she looks at me with a scared smile.

“Sandy, tonight I’m going to fulfill your secret fansies. I know who you are. And you’re about to learn who I am. Are you ready to take this journey with me?”

“Y… yes, Master. I am yours. I trust you. I love you.”

“Pick a safe word.”

I hear her breath catch. She didn’t expect me to be this serious. I need to give her a few minutes to digest this. “My safeword is… horsie.” She says it surprisingly comfortable. Then she gets a more lustful look in her eyes and says, “And this horsie wants her Master to ride her. Fuck, this is hot!”

Relief. Now all we have to do is to get over the Eve part.

“Now we’re all safed out. Everything will be okay, baby.” Oh, I hope it’ll be okay. If she uses the safe word, I’ll stop, but that will blow the deal with IT; then IT will release all the evidence against me and I’ll be ruined. At least she’s responding well – she seems to be turned on.

After all this time, I’m only just now figuring this out? And I had to have it pointed out? Shame on me!

So the big question now is whether the cuckquean thing is an actual wish or a never-actually-do-it fantasy.

“Strip for me, baby. Make it sexy.”

And she takes a moment to catch up again, but starts to unbutton, deeply. As she does, I keep talking, “you know you’ve wanted this for a long time. It took me too long to realize it… fuck, that’s hot… but I want it too. You are mine. You are going to learn how to serve. After tonight’sscene, we’ll figure this out, but for now, have no doubts. Oh my god!” She’s dropped her blouse and is pulling down her skirt: she is wearing a garter belt and stockings… She’s unclipping them and starts rolling them down her legs. “No, leave those on. They’re sexy.” She isn’t wearing panties. She came all set to fuck. Her pussy is gorgeous too. And she shaved for me tonight! That was very foresightful. “I want you… more than anything. I want you so much. I’ve done something that will surprise you. But just go with this experience and we’ll figure it out later. So nice.”

I ask her to pose and to turn around so I can appreciate her perfection and fully take it in.

“On your knees, I want you at my feet.”

She gets into a perfect slave display position: legs spread, chest out and her hands held, fingers intertwined, behind her back. She would make her master proud in the Gorean empire. But the interesting thing here is that her eyes seem to have unfocused. Her breathing is irregular. I’ve never seen her like this. “Yes, Master. Your little slave awaits your orders. How can I serve you?”

‘Slave’? This is a version of the fantasy I didn’t prepare for.

I guess I just go to my original plan. “Stand, baby.” She stands quickly. I get things from her present box, walk behind her and say, “collar!” She makes a little moan and dutifully tilts her head to the side, pulling her hair out of my way. As I put it on her, I say, “this is your provisional collar. You have to prove yourself worthy tonight if you ever wish to be actually collared by me.” I hear a tiny squeal in her throat. She’s really enjoying this. “You know a collar can be for control. It is a constant reminder of your slave status. But being actually collared is a serious commitment. Will you want that commitment, Sandy?” Oh, gee. I just made this a ‘promise collar’ didn’t I?

Her answer is only a moan. I don’t know if she’s avoiding the question or too lost to answer, but I’m not going to make an issue of it.

I step behind her. “You can relax your arms.” She does and I put the blindfold on her very securely. Then I start struggling her hair. Massaging her shoulders and her arms, “why did I blindfold you… Pet?” I forget to decide what I’d call her, so I’m defaulting to Mistress Kara’s choice, ‘Pet.’

“Mmm… thank you, Master. That’s nice. I guess because you don’t want me to see?”

I chuckle as my hands roam her body freely. “Yes, of course. That’s part of it. But also, it puts you in your head. It makes all your other senses that much more acute.”

“It makes me feel… helpless, Master.”

“You are helpless, Pet. You have chosen to submit to me. This is an important moment for us. But submission – true submission – is allowing yourself to be completely helpless.” I whisper in her ear, “to give up all control.” I whisper in the other ear, “you’ve given up all choice. Whatever happens here tonight is my decision. Youare just a participant. But remember, you are mine.”

As she moans, “I am yours,” my free exploration of her body gets personal. I tweak her nipples and she leans back on me and sights. I squeeze harder and she makes squeaky noises. “I would ask you if that feels good, but I know how you’re feeling right now. You’re starting to question what is pain and what is pleasure. I am doing this because I want you. And because I want to. Does it make you happy that I want to?”

Her voice is quieter… more distant, meditative, “mmmm… yes. Master. It really does. I want to please you. I want your cock, please Master.”

I spank her and get a yelp. “You don’t dictate what happens here! I do, you cum-greedy Pet. Do you need a reminder about who’s the master here?”

“You! You’re the master, Master!”

I pull her by the hair. Mock-forcefully: I would never actually hurt her. She follows me to the couch as I sit down. And I pull down on her collar pulling her into the position I want. “You’re going over my knee, Pet. You need to understand the consequences of forgetting your place.”

She whimpers. As I get her in position, I start to massage her pussy. God, it’s wet. She is really getting off on this! And this makes her sight.

This is the time; after getting her warmed and moaning, I spank her with my hand several times, getting yelps and yips. Then I massage her ass, then her pussy, which makes her moans louder.

“That’s a good girl. You’re cooperating well. Just to explain, I’m warming you up: bringing blood to the area so you will heal faster. It’s good for you in the long run. But when the paddling begins, this will make it hurt worse.”

She sighs loudly and take a stuttering breath, “thank you, Master. I need to be teach. I need to please you.”

She really is into this!

“Very well,” then I spank her continuously for several minutes, making her beautiful ass, back and tights a rosy pink. Her yelps turn to guttural noises. And then she disciplines herself to be quiet, though I know it’s getting to her because she flinches with each spank. “You’re being a good girl. You know you need this and it has to happen.” I stop and mass her pussy again; almost to the point of edge her.

I reach into the gift box with my other hand and pull out the paddle. I start rubbing it on her beautiful, naked ass. “This is one toy you know about, Pet, because you saw it. I have others.”

She’s dripping wet, moaning and trying to grind on my hand. “Master, please take your slut slave. Make me serve you. I am so horny for you. I’ll do anything. Oh!” I stop rubbing since I recognize that is an orgasm coming. But listening to her words, I am reassurered that this really is her fantasy. This is what she’s wanted: that’s her consent.

And I bring the paddle to bear.

“Ready yourself, little one. This is going to hurt you more than it hurts me!” I chuckle sadistically. I practiced this chuckle. But at that moment, I feel it. I am actually enjoying this. I’m enjoying a little playful hurting. I’m enjoying bringing her to new sensations. I’m enjoying sending her into subspace. And I’m smack-on loving getting her this horny. I am – I am a dom at heart! “In fact, I’m enjoying this. You better get a little worried about that.” I’m sure she can feel my boner underneath her delectable belly where she’s laying. I paddle her, hard, three times. She screams. “Oh, little one! That was hardly anything. But you’re going to have to be quiet. You don’t want me to put the gag in your mouth yet, do you?”

She whimpers. It’s adorable.

I finish the paddling, altering between that, and edging her. She’s already a sloppy mess, begging for release. But it’s getting close to seven, when Eve will get here.

“I’m so proud of you. You’ve been such a good girl. You’ve taken a lot from me and made me very happy.” I lift her face towards mine and kiss her tenderly, but she gets passwordate quickly.

She tries to scramble into my lap, but I stop her.

“No, baby girl. Not yet. This is only part of your fantasy. You need to live the whole thing. Will you do that for me? Because you love me and I love you?”

She whimpers and replies, in a quiet voice, “Yes, Master.”

I lead her to the chair and clip her wrists and ankles to it. Her breathing is so erratic, I’m worried that she might have a heart attack, so I get behind her and rub her shoulders again to calm her and reassure her a bit. “Don’t worry, Pet. Don’t worry, my love. Tonight is your dream. It’s not going to be bad…” …I hope she doesn’t think it’s bad, anyway.