The Anonymous Blacmailer

The Anonymous Blackmailer Ch 4

The blackmailer keeps training Terry.

© 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. Now, Terry is in the middle of a scene as a submissive with a dominatrix that the blackmailer arranged, but who seems to be training him, also, on how to dominate D/S scenes while she's making him submit. Terry and Eve are both terrified about what's coming next, but intensely curious about who's blackmailing them and why. And wondering what will happen when and if it's over.]

*Thursday*

I'm hanging from the ceiling, blindfolded, my nipples painfully constrained with weighted clamps, my legs spread, my aching dick in a cock cage and a metal butt-plug up my ass. I've just had the most painful spank of my life - pretty sure from a leather flail - and I'm scared to death while at the same time, completely given over to her control. I want her to be proud of me. Is this really subspace?

I'm here because a blackmailer has set up enough evidence to have me convicted for twenty life sentences, served consecutively. He told me to come, so I came. What else can I do? And there's a woman named Eve who is also being blackmailed. I have no idea what IT - we call the blackmailer 'IT' - ...what IT is making her do today.

And my tormenter - the dominatrix - only seems to have been hired to do this. She thinks I hired her, but actually it was the blackmailer.

And you know what? Now I'm enfolded in the scene. She's seduced me into subspace. I'm thinking differently: it's scary but somehow... freeing. All I want to do is to make her proud of me. I want to hear her coo, 'good boy.' I've lost myself in this, I'm not thinking right. I'm not thinking about anything else... just the world of sensation, fear, desire and titillation she's exposing me to.

Said sensation, at the moment, being pain. The flail cracks across my ass several more times. I make noises like "ahh!" but eventually discipline them to silence. I will not cry, I keep telling myself, though I feel moisture in my eyes. Then I feel a hand on my butt. The hand feels good, but the skin still stings. There's comfort in the hand. It's like caring. It rubs around. It wiggles my butt plug playfully. And I feel a whisper in my ear, "was that what you expected?"

"Yes and no, Mistress. I had no idea what to expect..."

In my other ear, "what do you say?"

"oh... sorry. Thank you, Mistress. This is what I needed. This is what I asked for. I need you... Mistress. Please continue."

I didn't think I ever asked for this, but she's right: I need to experience this. Life experience if nothing else. I need to understand. I need to know, firsthand, what being a sub feels like. I need to understand that within me - that part of me. The somewhat-submissive side that showed up on my kink quiz. I really am part submissive, aren't I?

"Such a good boy. Brace."

And the flail cracks again. On my ass, then up my back. It's a whole different sensation there. The sound doesn't seem as loud -- like she adjusted to the new flesh - but the pain is harsher... more specific. She keeps swatting, harder and harder. I've taken so much and I just want to scream, but, no, I want to make her proud of me, so I stifle the noises as best I can."

It stops. Finally, after an eternity, it stops. Her hand again, roving my butt, my back.

"Thank you, Mistress."

"Such a good boy. So brave. So strong. I love that you're taking this for me." Damn -- it does...! It makes me happy to hear her say that! It feels infantile, but that makes it seem so uncomplicated. I get a 'good boy' and we both are happy. This is such strange psychology, but I don't have the attention to figure it out. Only enough to be here, in the moment.

And again... more swats. This time, on my thighs... and at the juncture of the thigh and the butt. I've read that that spot is extremely sensitive, but until now, I had no idea. "Aaaaggghh," I scream. Over and over again. The pain is white-hot. I don't know how I can take more...

But then again, the soothing hand. And she strokes my brow. I'm perspiring now, and she knows it. I cannot believe how engrossing this is. There is nothing in my world except her. "Such a brave, brave boy. Are you ready for the cane?"

I can't answer that. The flail was bad enough. Shaking in my voice, I say, "whatever Mistress thinks...?"

"You must experience all things." She walks back to her table. "Oh yes. This..."

She returns... and goes to the back of my neck, I feel a poke. And another. A whine escapes my lips... is she sticking needles in me? But as it continues, I realize it's one of those needle-wheels... it kinda tickles, actually. Oops, now it's in my underarms and yes! It really tickles. I'm laughing as she continues, mercilessly tickling me in my left armpit, and I feel something in my right armpit. And it goes SNAP! It feels like I've been stabbed. I think it's one of those cattle prods. "AAAuggh!" and SNAP again... this time on my lower back, "Aaahaaa!" and SNAP again, on the side of my torso. "Awmph!" Every stab makes me tense and it feels like the buttplug is being jammed in me again, doubling the sensation.

Then it changes to a crackling sound - and it moves up my side, across my front... "ooh!" It feels like the skin is falling asleep! And she moves it all over my body. It's amazing... not bad, but a ton of sensation.

Then, she messes around with the toy a bit and puts a belt around me, attaching something metal to it.

"This is a 'power tripper.' I'm going to put this on a low setting to start."

This is all coming so fast. I feel like a train is running me over. A tidal wave of experience.

I think she read my mind - I guess you have to have great intuition to be a pro-domme.

"Pet, I was actually surprised that you asked for me to cover so much ground on our first session. Normally, I wouldn't be running you through anywhere near this much. But... you were clear in your messages and we're going to play all sorts of ways!"

And I feel a shock - like a static shock, only harder - on my arm. And then it moves up my arm. "This is the low setting, Mistress?"

"Shush, boy!" And she spanks my ass. Then she moves it over my chest. It feels like needles and pins - still it kinda tickles, but in a painful way. "Next setting. It's going to hurt more now" She continues and it almost feels like razors made of electricity cutting me. She runs it over my tortured nipples and I can't help but scream... and then she moves it down to my constrained cock and teases it within the cage. It feels like she's tasing me, cutting me: I can't help but groan with pain. Hidden behind my blindfold, I don't know exactly what she's doing, but she seems to have some sort of electrode with multiple points she's using on me. I don't know what to expect. It brings all my attention to my skin, to my body. It's almost like a painful zen state.

But my body is reacting in a surprising way. I am actually getting excited by this. I feel my cock busting to get out of its confines and painfully frustrated.

"You're being a good boy. Open your mouth. Stick out your tongue and hold it out... I feel a snap on my tongue and flinch, but she makes a noise too. She did that with her tongue? Is she grounded too? The electricity snaps to her? It happens again, but quickly our tongues wrestle. That snap came directly from her - no electrode! She pulls out, then teases me with the shocks... on my lip, tongue... she even hits the roof of my mouth once - ouch! But if I'm feeling this, she's feeling it too.

I melt with trust... she won't do something to me that she won't do to herself. This is her silent promise.

"Th... th. . . thank you Mistress. Fuck!"

She shocked my chest again and I think she had turned up the power - that one really hurt!

She spanks me, but the spank has a charge too... she, her whole body, is a conductor. "No cursing, boy! Don't think I won't wash your mouth out with soap!"

"Sorry, Mistress. Thank you, Mistress."

That damn buttplug: every time I tense, it feels like it impales me, fills me. I resolve to keep my sphincter relaxed every time she does something to me.

She rubs my aching shoulders, making me moan. "Still, you were a good boy. You made me proud." This is too fucking intense... "You're so good. I'm having so much fun watching your sexy body writhe with my attentions. I like your little suppressed screams. You're so hot. Do you want down? Will you promise to be a good submissive if I let you move?"

"Yes please, yes, Mistress. I'll do whatever you say. Please, Mistress. It hurts."

"You think that hurts? Wait for this!" She removes the nipple clamps quickly and as the blood rushes back to my man-nipples, so does all the pain they've built up. I can't help but wail a couple seconds, when I see another flash. "Good boy. That is a good one!" She slaps my nipples, which increases the sting, but somehow soothes it too. Once that sensation finally calms, she detaches me from the chains, but leaves all the cuffs in place. I start to stretch.

I get another swat on my ass and she pinches both of my abused nipples "Did I say you could stretch? Kneel on the floor! Yes, like that. Slave: display!" I know that posture from my reading, and assume it, legs spread, chest out, hands behind my head. "Now bow your head to the floor. I want you to grovel."

I grovel. But she keeps giving me commands and I realize she's having me do things like yoga stretches. Downward dog. Swan... Awkward as heck, stark naked with my cock's cage flapping around at it straining painfully to get out. But the exercises genuinely feel good after all I've been through. I just hope she doesn't put me into 'happy baby' pose.

"Can you believe it's been an hour, Pet? Time flies when you're being dommed."

"Really? Yes, Mistress. It is amazing. You're amazing."

"And we've only just begun! Most people aren't brave enough to book a long session for their first time. I'm, proud of you, Pet. What have you learned so far?"

'Only just begun?' Oh, my God!

"I've learned that time has no meaning if you're in a scene! I've learned that it really does matter if the domme comforts the sub - it sorta feels like... romance, desire; it feels like... like I matter to you. You're cruel to me, but I know you're doing it at least partly

for

me so I still like it. And the things I don't like, I know I'm doing

for you

to make you proud. To get positive feedback. In this space, it matters, doesn't it? It's a mind thing: I'm just not thinking normally."

"Good answer. What does that mean for a domme?"

"Um. Never break trust, Mistress. Check in. Be in your sub's mind even more than... his... body. Dominance is still about equals... just equals playing the role that gives them pleasure. Mistress."

"Good boy, you're making me proud. Stand slowly."

I'm appreciative she said 'slowly.' Something about this has made me so relaxed I think the oxygen would've slid from my skull if I'd been too fast. I'm a little off balance, but she holds my hand and supports me up. It feels nice to hold her hand.

She moves me to something until I feel it bumping my caged cock, then she has me bend over it... It doesn't take her long and I realize I'm being strapped to a whipping bench with my butt sticking out over the end. She straps a belt around me for some reason.

The terror is coming over me again. A feeling of complete helplessness, like when I was a child, being held down for a shot: knowing that something was going to happen that I knew I wouldn't like and that I had no choice doing.

'Trust,' I remind myself. Breathe. This has been rough, but I've survived until now and I will survive...

"Hmmm. I really was surprised, Pet, when you asked for such a thorough initiation session in your messages. You really were generous and I want you to get what you came for. And... I have to admit it's kinda fun putting you through the gauntlet!

"Now. Give me a number between one and five."

It feels like a trick question. It might be something good or bad. It might mean something to her if I choose an end. I'll pick... "three, Mistress."

"See, my little boytoy? It's you asking. You want three: I'll give you three. Ask again nicely."

"Please, Mistress. Three. Please."

"I wanted to introduce you to five other impact toys." Oh, crap - this is impact play! "...but now I have to pick out the three most representative. I'm giving you five strikes of each, though, since you took away two from my fun." I don't know if she's acting or if this is really 'her,' but she seems just a little too delighted to be doing this: I can hear it in her voice.

What a mind fuck.

She shuffles over to her table and returns.

I feel a soft surface playing over my butt. It feels soft... padded... I'm guessing a padded paddle. She runs it up and down my helpless back, plays with the buttplug in my back end. She taps it across my back lightly. It actually feels kind of good - if the flail hadn't already made the skin hurt, I'd think this was a pleasure play. Then THUMP! She lands it on my ass. I feel like I should scream, but it's actually easier than the flail.

"Thank you, Mistress."

Four more 'hard' smacks. Harder than the spanks, but still not terrible. One lands on my back and another on my thighs. I'm getting the whole tour...

"Name the tool, Pet."

"Padded paddle, Mistress?"

"Good. You took it well. As you can guess, that was the easiest toy I'm going to use on you. Next..."

I'm feeling something being dragged across my back. Like a wide strip of leather. Up and down my back, my legs. Back up, over my shoulders and back down.

This one is going to hurt.

And she swats me hard on the ass. I can't help but cry out and she swats me again and again, and on the back and on the thighs, giggling at the noises I make. "Identify that one, Pet."

"Thank you, Mistress. Uum... a wide belt?"

"It's a tawse, Pet. It was invented to spank naughty Scottish schoolboys. Look it up." I love the way it raises red marks on you. I feel her fingers trace up and down my body. "So sexy..."

She goes and gets something that swishes through the air. I feel it roll up and down my back.

A cane.

She swishes it again. I am terrified. It sounds as if she's hurting the very air.

"It's a shame. You asked for no visible marks that will last more than a couple days. I want to do this so badly!" swish, swish, swish. "Hmm... Do you know the word 'bastinado,' Pet."

Fear traverses my body. "Yes, Mistress. Foot torture, Mistress."

"Your instructions have left me no choice. No visible welts that will last more than a couple days.... Lift your feet."

I do what I'm told but beg anyway, "please, Mistress. No. I don't think I'm ready. Please...?"

She stops for a moment and gets quiet. She strokes my forehead and her voice is soothing but firm. "You will take this for me, Terry. You will, because you love to please me. It's what you want, Pet. It's what you need. It's what you asked for. She runs her hand over my head, the back of my neck, on my shoulders, up and down my back... My breathing calms. It's so calming by contrast to everything else that's happening.

"Are you ready, now, Pet?"

"If Mistress thinks this will be something I can stand. If Mistress will be pleased." I can't believe I said that. I know this pain is about the worst: I've read about it. If I had a safe word, If I was in control of this situation, I'd use it now. I hope it's not that bad.

She puts a gag in my mouth. She gives me a ball in my hand and says that dropping the ball is the same as using my safe word. "This room is soundproofed, but I don't want you waking the neighbors across the street, now." Then she caresses my head, strokes my brow and whispers, breathfully, in my ear. "You're going to be a good boy for me now. You're going to make me proud. Make me proud and I'll reward you. I'm going to fuck you so good..." And she strokes me. It really feels like she cares. It really feels like... romance...?

My mind is so messed up!

She steps back and makes swishing noises with her cane. And I feel a sting across my bottom. Whew - that wasn't so bad. "That was just for practice and aim. You're saying to yourself it wasn't so bad, aren't you?" And she laughs sadistically. "It was only to get my range. That was a love tap. If I was serious, you would know it. Now feet up again and put them together." I comply. I feel her set the cane on the soles of my feet. Aligning. The wait is terrifying.

I hear the swoosh milliseconds before feeling the pain. It takes palpable milliseconds for it to register - for my brain to make sense of the pain - and then it blooms; it's heat, it's agony... like a burning hot sword just sliced the bottom of my foot. I scream as loudly as the gag will let me. And tensing my ass feels like I'm been stabbed by the buttplug. But I hold the ball. I can't drop the ball. I no longer know if I won't because of IT or because of Mistress, but, damn it, I won't drop the ball.

I feel her caress my back, stroke my hair, "that's a good boy. I'm so proud of you. You're doing this for me. It is so fucking sexy!" Then she steps away.

I feel the alignment against my feet again. Oh, god, no... not again. But four more times in rapid succession. Another camera flash in the middle of that; she's dexterous! I'm screaming, flailing, thrashing as much as I can, but that's not much in my restraints.

I groan to myself in misery: I'll never walk again.

"She rubs my feet. It hurts but it feels good. Then I feel some sort of lotion being rubbed on my back, my aching ass. She stops a moment to play with the buttplug and continues putting the soothing cream with her glorious touch on my painful thighs and finally on my tortured feet. In history, bastinado punishment was used on slaves who were caught while trying to escape to ensure they'd never run away. Now I understand how effective that is. I'm afraid I won't ever be able to walk again. If I were a slave, I'd never willingly submit to that again.

But the footrub, when not aggravating the pain, is also so nice and relaxing.

"God, that was hot. You're so sexy, Terry. I loved your muffled screams. Your thrashing almost made me cum. You know I'm going to reward you. I'm going to fuck you now, Pet. I'm going to make you mine. I'm going to penetrate you and be your first..." 'Penetrate?' Oh, shit! I thought she meant...

"You're going to feel what it's like to be used. You're going to be my sex toy, Terry. I'm going to fuck you so good..."

She goes away and shuffles at her table. I realize I have no idea what she looks like - I haven't seen her yet. I've only felt her hands, her arms and her breasts as they had pushed on my back while tying me. And of course, her awesome tongue. Judging from the angles when we kissed, I think she's shorter than me. And I've felt her hair brush against me, so I think she has long hair. I want to see her! I don't fucking care what she looks like, I just want to know who it is back there.

Oh! I didn't feel her return, but the buttplug is being moved in and out, coaxingly. "Remember all you've learned, Pet. Remember how to relax your pretty ass. Your boy pussy. I'm going to take you now. I'm so turned on, I can't promise control. For that I'm sorry, but... I'm not sorry. You need to know what it feels to be owned, Terry. And I need to cum. I need it so bad. I'm going to fuck you, Pet. I want you..."

Submissives need to feel wanted. In a strange lucid moment, my overmind took over: I see what she did there.