Sweet Surrender Pt. 05

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Backstory, and tasks are undertaken.
4.1k words
4.8
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Part 5 of the 8 part series

Updated 11/11/2023
Created 10/28/2023
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Profile: surrender2mygaze (*this is a fictional account)

Gender: Male

Age: 33-40

Weight: Average

Height: Tall

Location: [redacted]

Orientation: Straight

Interested In: writing, camping, motorcycles, craft beer tours

Status: Attached

Fetishes: bdsm, rough play, voyeurism, ultra-feminine attire

Pets: Dog(s)

Some words from surrender2mygaze:

In real life, I'm the one who would catch your furtive glance from across the room and then hold it until you looked away first. But I'm also the one who would let that moment pass without saying a word or making another move. A half-smile is the only other gesture before I vanish, satisfied with having left a lingering 'what-if' in your thoughts, while my own mind remains unfettered and unbothered.

But of course, that's all a facade. My urges are in fact tightly fettered, kept under strict control, and only my imagination is running amok, constructing an elaborate narrative about you based on that one long look. I should be thinking and behaving responsibly, staying engaged in my actual life, not my fictional one. But my day has been derailed, just like I wanted my eyes to do to you. The honest truth is you were always perfectly safe, but that doesn't explain the part of my head that tends to excel in... creative endangerment? Seductive predicaments?

But that is what cyber is best-suited for doing, and all that I'm here to explore for now. To wonder what I might have been capable of, and to reveal what might have lingered in your mind for the rest of the day. Were we fated for frustration? Or destined for depravity? Let's find out.

Sienna + Ben

Date: Mon Sep 14, 9:06 AM

Subject: Chat Log

[Sienna]: Ben, I'm sorry that I haven't started my assignments. I had some unexpected travel come up for work, and I'm just now settling in again. You've been in my mind (and in my panties) this whole time, I promise. I've just been so tied up (and not in any sort of good way). Play time will resume shortly!

[Ben]: Glad you're ok! And not to worry, I try my best to maintain complete respect for all real-life boundaries. Any impatience from me is always done in fun (well, 99%). Unless, of course, you ever make a very specific commitment to doing something. Fair warning on that! For now, I'm just playfully yanking your chain (and matching your awful double-entendres).

[Sienna]: I will say that your writing has dredged many thoughts and memories to the surface lately, like the last time I was tied to a bed spread-eagled. Mortified. Flushed. AROUSED. Unable to close my legs, hide my sex, prevent anything that might be done to me. My kitty was absolutely dripping wet. Much like it is now.

[Ben]: Oh, the predicaments I would still like to imagine you in. But I could start with a simple spread-eagle, sure! *grin* I'll put that note in the suggestion box for a future story.

[Sienna]: Then you DO take requests after all!

[Ben]: When it suits me and when I have the time. The next part of the main story is roughly 3/4 done, btw. But I think you know you aren't seeing it until I get something good first...

[Sienna]: Ohhh, you are a hard task master. Which I think I might enjoy!

[Ben]: Careful, some titles should not be used too lightly. But yes, I can confirm that I'm getting hard right now.

[Sienna]: That makes me happy!

[Ben]: Also coming shortly is a four-episode story run I will call: "Motivational Techniques for Erotic Writing 101". Each day, I'm going to send you something from the demented mind of your anonymous Internet stalker, in the hopes of guiding you through the process of breaking a writing assignment down into manageable pieces, bending it to your will. With real examples! All while keeping us both entertained!!

[Sienna]: Now that makes me even happier!

[Ben]: And just in case none of that provides enough inspiration, you are also not allowed to play with yourself until you've sent me your first "warm-up" email.

[Sienna]: Fuck off! Seriously? What if my brain wants to tell you it's way too soon for you to push that kind of rule on me?

[Ben]: Oh, really? Is that so? What is your body telling you?

[Sienna]: That I'm a horny little bitch. And a total sucker for incentives.

[Ben]: Great! I'm glad we're on the same page then.

To: Ben

Date: Wed Sep 16, 11:31 PM

Subject: Something About Sienna

Let me start with a confession first. This email is not going to be quite as detailed as the one you wrote, at least not in terms of providing more recent personal details about myself. I enjoyed yours, and I mean it when I say that I can picture myself kneeling and begging for more dirty tales of your past (pant pant!), but I'm not quite ready to open my kimono yet. I hope you'll forgive a lady for being a bit skittish about her privacy and safety, and for wanting to preserve some of her carefully crafted present-day illusions for the time being? *bats eyelashes*

The whole reason I'm using the site we met on is for a shadowy version of me to get to mess around and have fun outside the confines of my DINK lifestyle, mortgage-slave, corporate ladder climbing reality. I think you understand that perspective. I'm not going to defend it to you. Most of my worst "adulting" has been in the last five years or so, and I'm feeling very torn about it. I love parts of it and I hate parts of it, but I feel like I have a lot to lose if I let myself backslide too far, if I let myself become as rash and impulsive as I used to be. Does that make sense, in a sort of 'split personalities fighting for control' kind of way?

Because I'm definitely backsliding. The girl that is connecting more with your stories is the version of me from her mid-to-late twenties. The brains-and-body total package with the cryptic finance job that involved trading things nobody else understood, and that none of her friends even bothered to ask about, as long as it kept funding the wild nights out. Downtown divas living the 500 square foot (or less) condo lifestyle, only there for passing out or fucking, otherwise at work or partying. Usually straight from one to the other. Often on the arm of some cocksure asshole you could swap out any time. Rooftop patios overlooking the city when the weather was good, exclusive invite-only clubs where we always skipped the line, bottle service in the lounge, drugs on the dance floor. And then more fucking in the bathroom. You have hammered and nailed that part of me pretty accurately. Well, in some moments.

Let's just say it wasn't always the guys that I'd end up fucking. Hey, a cunt-about-the-town needs some variety! And it felt like that option was always at my beck and call. Or was it the other way around...?

Why was a girl my age staying late at the office on a Friday night? Sometimes the job demanded it. Monetary freedom comes with a price. My girls knew I would be joining them, and that I expected them to have plenty of sordid details to share once I made my fashionably late entrance. They'd keep me updated in the meantime. But there was one girl in particular... if she checked in, if she was part of the evening's plans, I'd need a quick frig right at my desk just to get her off my mind.

That little minx used to send me the filthiest text messages, one after another, a few minutes apart, while she was out clubbing. Or a photo peek of the bra she was wearing that night. Or a snapshot of her panties already off and in her hand, in that same club. For years I kept an audio file on my phone of her cumming in the backseat of a rideshare... She was relentless. Any time I heard her custom message ding, I immediately got wet. Ring a bell, and I salivate. She took advantage of that.

In fact, she was the first person I let have any sort of real influence over me. She knew exactly what her evening text-capades would drive me to, madly rubbing myself off in anticipation of a wild night ahead. Head up, watching for the cleaning staff, legs spread under the desk, skirt rolled up to my waist, fingers molesting my clit and pussy. With so few women at work, I had the washroom to myself whenever I needed it, but where was the fun in that? I'm sad I never did get caught...

Did you enjoy that little detour? Yes, I was an unapologetic slut. Up for just about anything if it got me off, and not really caring how. It took me a long time to understand that there were some things I was missing out on. I believed I had it all, or could go out and get it! Work and play were not really separated in my head, everything was organized in terms of commodities, price, cornering the market. Being on the winning side, not the losing one. And surrendering wasn't even an option.

My career has changed in some ways, but I'm still playing equity and securities games. It is still a male-dominated field, especially in the upper ranks of my colleagues and clients. The core of what I do now is not as much about manipulation of numbers as it is manipulation of people. Using my influence to build trust, change minds, close deals, gain the upper hand. I've built a successful career on my ability to manipulate people -- men in particular -- and that contributes to my ongoing struggle with the concept of "submission". I know the games too well, and sadly most men are not very artful or clever when they put on a power move, because they rarely need to be. I see right through what they're selling. I know when it's just a lazy opening move to get me to spread my legs -- which, ok, used to be my whole vibe, I freely admit. I just can't pretend to buy it anymore, and I get boooored so easily.

The point I was trying to reach here, though, is that I did figure out what I was missing, eventually. I truly cannot get enough when I come across the right man with the ability to overwhelm me. The internal struggle between the awareness that I'm being coerced or controlled or forced, and allowing myself to go along with it, to be seduced by it, until slowly it starts to feel like I never had a choice... THAT is fucking arousing to me.

The boy has stamina, I'll give him that. And the way he handles me brooks no argument (there is only false and mild protest coming from these lips). He knows how to work a woman's body. Every time he senses that I'm getting too close, he slows his pace, never letting me quite get to where I want to go. He has me like putty clenched in his strong, young fist. I'd do anything at this point for him. I moan and mewl in frustration, but he continues the same way for a while longer, just a reminder that he is owning my body, and I have no say. Then he stops entirely, to underline his point. I'm a sopping mess. It feels like he's been fucking me for hours. He probably has been. Never once letting me cum. Always bringing me back to from the brink. I'm a quivering pile of well-fucked flesh at this stage. Drifting in a gauzy haze of brainless pleasure, my body completely drenched, and I'm begging him, pleading him to take me there.

But he won't. He just keeps pumping away, and then stopping again. Changing our positions. One leg over his shoulder. both legs over my head. Rolling onto my side. I try pulling away, needing a break, maybe some water, attempting to re-assert some level of control, but he simply flips me like a rag doll, thrusts his beautiful cock in even deeper from behind, and I'm his shattered slut. Hunched over, face pressed into the pillows, my back and ass arching up compulsively. Hungrily. Desperately. But still not orgasmically. Until finally, with a wide smirk on his face, he gives me permission to cum. Commands it. And that is mindblowing. The helplessness in that moment. I was screaming before, but now there is no sound coming from me at all. Just an eyes closed, mouth opened, toes curled massive fucking capital O.

Oops, I've digressed again, and gotten myself more than a little turned on by another resurfaced memory. Shall we leave things there for now?

To: Sienna

Date: Sat Sep 19, 11:28 AM

Subject: Motivational Techniques for Erotic Writing 101 (1 / 4)

Wow, you've earned your rewards today! Yes, you know what I mean...

Also, here's my inspirational offering for Assignment #1 - An Origin Story:

I have to admit that this is an odd little story, even for me. In a way, I'm mocking myself, using the concept that all of my repeated references to your lofty Louboutins have become like a narrative crutch for me, a writerly fetish instead of just a kink. And yet, these repeated mentions are the seed that could lead to a full-blown real fetish for your alter-ego somewhere down the road (if it isn't already, haha!).

***

She was perched on the side of the bed, almost fully dressed now, her hair in loose curls, her makeup done. She sat there and looked across the room at the closet door, trying to delay the next moment, trying not to let any of the attached memories bubble closer to the surface. But she couldn't stop them. They were already in her head. Which was precisely why she was still sitting there, staring into space for so long. She knew that every time he told her to wear the red Louboutins, her night never ended in the way she expected.

The shoes had developed quite the hold on her. Once just an extravagant gift, in time they had gradually become a direct physical trigger for her to feel instantly turned on. She couldn't wear them to the office; she would have lost her job, very quickly. It was impossible to keep her mind from fantasizing about the lust lurking behind every look that turned her way. She would ache for rough hands to pull her into an empty office and throw her on the desk. She would long to submit to the impulsive whims and sexual vices of others. And to address those urges, she would be forced to rush into the ladies' room for relief. But that very specific position of sitting on the toilet in her heels, legs spread, knees high and calves taut, would trigger another rush of reckless heat through her body. She could sit there until her clit was raw, trying to keep her noises to a minimum, but it would never completely remedy her wanton state.

She was running out of leeway before the scheduled pick-up time. At last, she stood and stepped into the closet. There they sat, perched on their own shelf, waiting for her. Confident, alert, expectant, eager, aware of their power over her. She took them down, placed them carefully together in front of her feet, and religiously slid the left foot in (always the left first, he was left-handed), and then the right. That simple ritual was entirely erotic to her, and her body instantly responded, as it always did. Her sexuality was unleashed, while her rational, independent mind was locked away safely.

***

The drive to the restaurant was taking them into the downtown core. She tried to sit back and relax, tried to make small talk, tried to act like this was just a casual night out and not an elaborate soirée with a pre-determined outcome. He steered the conversation around several times to compliment her on her appearance, spoiling her with both his attention and with this special night out. He was very well dressed for the evening, custom Zegna suit and Italian leather shoes, cufflink shirt and Hermes tie, from head to foot a true gentleman in appearance. But this was a lavish mask of deception. He was a man in total control of the evening, of the direction it would take, and of her place within it. She knew this, and not just because her shoes had been whispering it to her, promising her that it was so.

But her feet were also murmuring a few indignant complaints. In all of his effusive praise, the shoes had not once been mentioned. He had asked for her to wear them specifically, a clear signal of his mood, but now it was as if he had forgotten about them. Why? All she knew for certain was that this night was still headed sideways. Someway, somehow.

She was barely surprised when he announced that they would be making a quick stop, pulling in at his office building instead of the restaurant. He opened the door on her side of the car and offered his hand. "Come up with me, I need to take care of something. It might take a few minutes." Her shoes were already lifting her out of the car, urging her forward, so she followed him compliantly into the converted loft space, past the exposed brick and wooden beams, and into his spacious office at the back. There didn't seem to be a soul anywhere in the building, and yet he closed the door behind them anyway.

"I've called the restaurant already, just to let them know we'll be late. I'm feeling impatient about something else tonight. Put your hands out in front of you." Her arms moved of their own accord, while he unlocked a desk drawer and pulled out a long bundle of rope. As she gazed gratefully down at her shoes, he bound her wrists tightly together, and then threw the rope up and over the exposed beam above. Pulling down, he raised her arms until she was stretched and reaching upwards to her full length, heels included, before tying the end of the rope to the desk.

He took her head in his hands and kissed her deeply, powerfully, possessively. Then he smiled wickedly, slid one foot between her two, and very unceremoniously kicked both of her shoes off and out from under her.

If felt so much worse than being slapped, and she gasped in outrage. As she hung there, her toes just barely touching the floor and scrabbling to stop herself from spinning, she looked down at the discarded pumps in shock, concern and desperation, like her anchor had just been cut loose and she was drifting out to sea. He snapped her attention back sharply, lifting her chin and looking into her eyes. "You know, I am aroused by you, and obsessed with you, with or without the shoes."

She was still fiercely aroused by him, as well. But she had almost used her safe-word. It would have only been the second time ever. And not out of any concern for her own safety, no. For the safety of her shoes! Was that a bad thing? She had never found the courage to explain to him just how much she adored her Louboutins, how much of a role they played, how deeply they were connected to her erotic soul now. It was because she knew he could be the jealous type. And apparently, he already knew.

"It's time to make sure your focus is always on me, and only on me," he whispered to her.

Oh, my. This was not going to end well for anyone.

To: Ben

Date: Sun Sep 20, 10:01 PM

Subject: An Origin Story

Those poor, poor Loubs! I had to think about something else while I played with my kitty, it was all too horrific to imagine!

My thirst for smutty storytelling is far from satisfied, and you continue to stir up old memories that I can turn into tawdry tales of my own. I still feel there's a need to pull my weight and give as good as I get! I know you like it when things are unequal, but I would bet you also enjoy the sense that you've met a worthy match?

In that spirit, I offer you not one, but TWO short origin tales, a double shot espresso of who I was in my slut era, the second being the moment I realized I was no longer getting what I really wanted.

I walked out of my apartment at an ungodly hour, craving coffee and carbs after having drank my weight in martinis and vodka shots the previous night with the boys on the floor. I was feeling quite proud at being up and about. My normal routine would have been to cocoon in my king-sized bed and bemoan my condition for hours, before dragging my ass into the office to finish what I hadn't the night before.

Alone in the elevator, no stops all the way down, I was surprised when the doors parted on the ground floor and revealed a Saturday morning paper bag princess. True flotsam from the night before, sunglasses still on, carrying her shoes, hair tousled, reeking of booze and sweat. Well, hello there! Just another single girl in the city. Nothing like a solid gold Saturday morning walk of shame. I knew this girl because I was this girl.

12