Learning the Rules Ch. 07

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Jessica's lesson in restraint comes with a huge reward...
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Part 7 of the 11 part series

Updated 06/14/2023
Created 01/29/2023
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ElizaGrey
ElizaGrey
272 Followers

[Hello kittens! Thanks so much for all your enthusiasm so far - it's much appreciated!...Here comes chapter seven --- Enjoy! EG x]

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Polite notice: this, is chapter *seven* of an eleven-chapter novella.

Personally? I think the chapters are infinitely more enjoyable read in order, but of course I'm not going to police how you enjoy your smut!

It's also a prequel, to the first story I shared - Rules are Made to be Broken - it's not essential to have read that first, but this chapter in particular makes more sense if you have. Your call!

Too busy to catch up? Here's where we're at:

Jessica, is training to be a submissive call girl, she's on day four of seven, and her teacher, Mr Swift, has just brought her back from a field trip to a BDSM club (it's worth catching up on at least chapter 6 for that fun ;)...

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When we get back to Mr Swift's house, he pours us each a glass of white wine and we sit together on the sofa.

'So, I imagine you have questions?' he asks with a smile

'Um, yes Master. Lots.' I confirm with a small smile of my own

'Oliver, Jessica. Consider this a break in tonight's lesson -- a de-brief if you like. Remember how important it is to be able to switch back after submitting.' He says seriously and I nod.

'Right. Then yes, Oliver, I definitely have questions.' He smiles at me again,

'Then ask away.' He replies, and I take a deep breath.

'Alright. Pandora. Why did you...' I trail off,

'Why did I give her permission to let you come?' I nod, taking a large gulp of wine from my glass. 'Because I knew that I had exposed you to a lot in a short time and that you're not used to being edged. I offered a means of release because I wanted you able to concentrate and take in everything around you, not have you using all your focus to suppress your orgasm. Of course, I could have taken care of you myself, but by allowing Pandora to relieve you at my instruction, you showed me trust and a deeper submission. You did very well.' He smiles and I blush at his praise. 'Did you enjoy letting Pandora touch you?' he asks,

'Yes.' I reply quietly, 'Although, not because she's a woman -- I've never been curious about that, but just because I needed that orgasm so badly, and I knew that you had permitted it, so I just...' I shrug

'You submitted, instinctively.' He fills in the gap, proudly.

'I guess I did.' I muse. 'What Vincent did, to Citrine, before they left. Will you do that to me before the week's out?' I ask tentatively, not sure if I really want to know.

'Do you mean will I have you perform on stage, or will I add a clamp to your clit?'

'Both.' I whisper.

'Yes, Jessica, I will do both.' He replies simply and I swallow hard. 'Unless, you use your safe word, of course. Crystal likes public submission to be included in the training so that a potential employee can find out first-hand how they feel about it, but she has plenty of clients with no interest in club bookings, and several girls who choose to make them a hard limit.' I feel myself breathe a sigh of relief, though remembering Citrine's cries of sheer pleasure, maybe it would be silly not to at least try? I push the thought to one side for now.

'And what about what she was doing when we got there?' I ask instead

'Edging herself, you mean? With the dildo in her ass?' I nod

'Also, yes. It's a valuable tool in learning to control your pleasure, whether in public or otherwise.' His reply makes my pussy throb and I'm not sure why.

'Will you -- flog me, too?' I ask tentatively,

'Absolutely. Floggers are a common preference for most Doms, so it's really a vital part of your training. Vincent's toy is very much a custom version though -- he's a diamond merchant by trade -- Vincent Salter -- as in Salter's Stones? He likes to show off a little now and then.' There's good natured mocking in his tone, 'I prefer more traditional styles in suede and leather.' He adds with a smile that does nothing to calm the ache between my legs.

'What are you by trade?' I ask, my curiosity getting the better of me, 'Sorry, am I even allowed to ask that?' I correct myself quickly but Oliver just smiles.

'Of course, you are! We're chatting as equals Jessica; you can ask me whatever you like.' I smile back, relieved at his relaxed response. 'I'm an art dealer -- I own a couple of small galleries here in the city and another in Paris.' He adds humbly,

'Oh, wow.' I reply, impressed, 'So, paintings or sculpture, or?' I trail off.

'A little of everything; fine art, photography, sculpture, textiles. I suppose you could say I consider myself a connoisseur of beautiful things.' He adds, looking at me pointedly, making me blush. It feels like a good time to ask the other question that I wasn't sure I'd be allowed to,

'So, Citrine. Did you train her too?' I ask, already knowing the answer. Oliver nods.

'I did. Crystal has around a dozen girls on her books at present, I trained eight of them.' He tells me plainly, as if reinforcing the lesson, I'm sure he seeded earlier. 'Like you, they're all intelligent, beautiful young women; who I am sure will use this opportunity to fund impressive futures in whatever destiny they choose for themselves.' He says it with something like pride or admiration in his voice.

I start to realise that tonight was about more than just taking me to that club.

He's gently trying to burst the hedonistic bubble I've been lost in since I met him, reminding me that I'm considering a job opportunity, not a lifestyle or a relationship with him. It makes me feel somehow bolder about all the things I've done so far. Because I'm choosing to do them, to push myself, not just blindly following orders like those collared blondes.

I think of what Citrine said about indulging my submissive alter-ego -- then I remember Crystal's words from Friday night and it hits me -- I already do feel empowered by my own actions, and by giving myself permission to indulge in what's bringing me huge amounts of pleasure.

I sit back a little, trying to think of what else I wanted to ask and inadvertently drive the plug in my ass deeper, making myself gasp. There's a twitch of amusement on Mr Swift's mouth.

'Pandora told me you let her fuck your little ass quite thoroughly with that plug -- not bad considering you didn't think it was going to fit.' He muses and I blush with a smile

'I'm definitely finding pleasure in things I didn't expect to.' I tell him honestly

'I'm very glad to hear that, Jessica.' He smiles, 'Now, would you like to go upstairs and finish tonight's session?' he asks and I nod, slipping back into my submissive alter ego.

'Yes please, Master.

Upstairs, Mr Swift has me strip out of my tiny dress before he positions me on the bed on all fours. He stalks around me, slowly unbuttoning his shirt. I realise it's the first time I've seen him partially naked, other than his cock, and he doesn't disappoint. His broad shoulders are muscular and lean, and judging by the toned muscles in his arms and chest, Mr Swift is no stranger to the gym. I try not to stare as each new inch of flesh is revealed, but he's delicious.

'Since you handled being cuffed so well, Jessica, I'd like to restrain you again now, a little more substantially.' He says plainly, showing me a heavier pair of leather cuffs joined by just an inch of chain, and another set that are attached to a metal pole about half a metre wide. When I make no attempt to protest, he continues.

'Good girl. Now, ease your shoulders down onto the bed and put your hands behind your back.' I do as I'm told, breathing a little harder as he binds my wrists tightly together behind me. A soft gasp escapes my lips when I feel another cuff being attached to my left ankle, then his hands parting my legs a little wider to make room for the metal bar before securing my right ankle in the other cuff, effectively holding me open and putting me on display.

I feel instantly vulnerable, but the helplessness of my bound position is only turning me on and with my pussy spread open, there's no way to disguise the evidence of my arousal that's already coating my thighs.

'You look stunning, Jessica.' He tells me from behind, and I blush, panting softly with anticipation, 'Very, inviting.' He muses as he smooths his palms over the curves of my ass. Then his hands are on my wrists, urging them lower. 'Can you reach the base of your toy, Jessica?' he asks casually and my breath catches in my throat, momentarily stunned.

'Ow!' I cry out as a sharp spank lands on my right ass cheek.

'Remember the importance of prompt responses, Jessica.' He scolds, but with a trace of a smirk in his voice.

'Sorry, Master.' I breathe quickly, then without thinking, stretch as best I can to reach for the toy buried in my ass. I find I can actually curl my fingers around it quite easily. 'Yes, Master. I can reach it.'

'Good. Then show me how Pandora worked it in and out for you.' He says, reverting to his casual tone. I briefly think about saying yellow, but then I remember how good it felt when Pandora got me off with the toy, and my own lust wins out. I take hold of the butt plug and start working it in and out of my ass while Mr Swift watches.

'How does that feel, Jessica?' he asks softly,

'So good, Master.' I reply dreamily

'Do you think you could make yourself come as hard as Pandora did?' he toys sweetly,

'Yes, I think so, Master.' I murmur. And I really, really want to. At that moment, another hard spank lands on my ass and Mr Swift's other hand covers mine, forcing the plug back inside me and stilling it there.

'Not without my permission, Jessica.' He reminds me, gently but firmly. He fingers me deeply, scooping up my creamy juices to smear more against my little puckered hole and around the toy that's stretching it full. 'Again.'

He makes me bring myself to the edge of orgasm three more times, bound and held open, easing that monster plug in and out of my own ass, harder and faster as per his instructions. Each time, when I start to breathe harder and faster, willing him to let me push myself over, he lands his palm sharply on my ass to bring me back from the brink.

'You really are doing very well, Jessica.' He soothes, stroking the rounded cheeks of my ass. 'I think you deserve a reward.' Then his hands are gone and I hear the familiar sound of a condom being opened and very nearly come undone at the mere thought of finally feeling his cock inside me.

A moment later, I get my wish. He eases slowly, but firmly into my creaming pussy, making me cry out in desire. With my ass still stretched full by the butt plug, he feels huge and I feel impossibly full. It's almost overwhelming, but it's incredible. He pulls out all but the head of his hard length and then pounds me again, harder, then again, faster, holding onto my hips, gradually building pace until I'm mewling pleasurably, lost to his deliciously deep fucking.

'Is that what you've been craving, Jessica?' he presses his hard chest against my back and growls in my ear as he claims my needy little cunt over and over.

'Yes, Master!' I manage to reply breathlessly, followed by a fresh wail of lust as his fingers take hold of the base of the butt plug. He starts to work it in and out of my ass again -- slowly at first, building momentum until he's fucking my ass in time with my pussy and I'm moaning almost constantly, submitting myself entirely to this man who seems to know exactly what I want, what I need.

'Oh Master, please. Please may I come for you?' I whine, not sure how much longer I can last

'Not yet, Jessica. Not until my cock is buried deep in your sweet ass.' He growls, never missing a stroke. I'm momentarily thrown. He's made no secret of the fact he plans to fuck my ass, but feeling how hard he's pounding my cunt, I'm worried he'd split me in two. He must feel me tense up because he says,

'Give me a colour Jessica.', still steadily fucking both my holes, but more gently now. I realise I want that powerful urgency back, and I want it wherever he wants to give it to me.

'Green, Master.' I breathe without hesitation and he quickly gathers steam again,

'Good girl.' He whispers, reaching around to stroke my clit and sending new waves of delight rippling through me.

'Please Master!' I moan desperately, 'Please fuck my ass!' the words are out before I realise what I've said. I want to come so badly; I'll do whatever he wants to earn it -- but it's not just that. I'm so turned on, so full of lust and craving because of how good the plug feels, that I really do want to feel his hard dick in my most intimate little hole.

'Oh, with pleasure, Jessica.' His voice is low and controlled, but in a heartbeat, he slides the plug out of my ass and replaces it with his thick cock in one fluid motion and with a satisfied grunt of desire. I scream at the feel of him, buried to the hilt in my tightest hole, holding me steady, giving me a moment to get used to the new, deeper and more delicious intrusion in my eager ass.

'Now, you may come, Jessica.' He breathes against my ear as he starts to move. Still gently stroking my clit, Mr Swift claims my ass with his delicious cock, harder and deeper than the plug ever reached, and it is divine. He's thoroughly lubricated from pounding my pussy, his thick length gliding in and out of my ass with ease. With his permission, and his fingers still dancing on my clit, I have one of the most explosive orgasms of my life, followed quickly by a second.

He fucks my ass soundly through both, never stopping his long, deep strokes. Eventually, I feel him still, and an animalistic roar of satisfaction announces his own climax, still buried deep in my tight, stretched ass. After a minute of breathing deeply, he pulls out gently saying,

'I told you that you'd learn to love the feel of my cock in your ass.' I can't help smiling

'You did. And you were right, Master... That was incredible.' I breathe back.

* * * * *

I wake the next morning feeling well rested and energised. I lie in bed, stretching out in the early sunlight, re-running last night over in my mind -- the huge new plug, the club -- the collared blondes -- meeting Citrine -- letting Pandora make me come -- letting Mr Swift make me come in the middle of the club -- and of course, when he finally claimed my ass.

Those few hours were more adventurous than my entire sex life to date. It was kinky and decadent and dirty and I loved every moment. It feels bold to embrace my own wanton desires, but the idea that doing so might let me turn my entire life around, is what's really making me smile. With that thought in mind, I bound out of bed, deciding that today is the day I do something I've been deliberately putting off.

Downstairs, Anna is making coffee, she offers me a cup and I gratefully accept, perching on a stool at the kitchen island.

'You seem very cheerful today.' She says, eyeing me curiously, 'Which is a good thing!' she adds quickly, 'I've hated seeing you so knocked down by what that wanker tried to do...' she trails off, her eyes flashing anger. She's talking about Clarke trying to proposition me, of course.

'I know. And thank you, Anna -- really -- for being there, and having my back, and letting me have my old room back.' She waves me off,

'Don't be stupid Jess, that room is yours, always. I'm just glad to see you looking brighter.'

'I feel brighter.' I agree, 'And I'll feel even better after today.' I tell her. She narrows her eyes at me in question. 'I'm going to go and get my stuff from Clarke's spare room so that I never have to see that disgusting man ever again.' I announce proudly.

'Not on your own, you're not.' Anna replies without missing a beat, 'Tom's gone to work already and I'm supposed to be viewing potential premises for the bakery, but I'll rearrange -- you are not going there on your own.' She repeats firmly.

'I'll be fine.' I tell her. 'I checked his schedule on the university website -- he's hosting a lunch for some lecturers visiting from Canada -- I'll be in and out before he gets back. Don't you dare change your plans -- you've got your own big dreams to make reality!' I beam at her brightly and she relents,

'Well, as long as you're sure he won't be there?' she warns,

'Positive.' I smile back.

* * * * *

About an hour later, I let myself into Andrew Clarke's flat using the key he gave me three months ago. I step cautiously into the hall and listen for any signs of life -- silence. I take a deep breath and head to the room I'd been staying in until last week.

I shudder on sight of the bed. Images flood my head of Clarke pushing me down on it roughly, his hands roaming, my skirt bunched around my waist, his fingers grazing my silk underwear... the memory makes me feel queasy. I force myself to block it out and get on with what I came here for.

Quickly, I start bundling my clothes and other possessions into the floral hold-all I brought them here in, grateful that I packed very lightly. I do a quick sweep of the en-suite and retrieve some make up, moisturiser and my toothbrush. I don't want to leave any part of myself here.

I cross to the writing desk, tuck my laptop carefully into the side pocket of my bag then sweep the rest of the surface into the main part -- pens, notebooks, post-its and flash drives -- all in one swoop before zipping it up and swinging it onto my shoulder. Finally, I open the drawer and take out a weighty cardboard box file. My only printed copy of my manuscript -- An Untameable Girl. I stroke the box lightly, smiling softly to myself. Hopefully, by this time next week, I'll be on my way to publishing her on my own terms.

'I knew you'd see sense and change your mind.' Andrew Clarke's voice behind me makes my heart stop and my blood run cold. I turn around to face him,

'What are you doing here? You're supposed to be at a lunch -- with' I start,

'Postponed.' He cuts me off, 'My guests' flight was delayed. Must be fate.' He smiles easily, oozing charm, eyeing me salaciously, 'Because look at the pretty little treat I've come home to instead.' he says, looking me up and down lecherously. I suddenly hate myself for embracing this morning's sunshine and throwing on a short strappy sundress. 'You know,' he continues, moving toward me, 'That was quite a feisty kick in the balls you gave me last week, but I'll forgive and forget as long as you take your time kissing them better.' He sleazes, stroking his forefinger over my bare shoulder. It makes me shudder, but I find I'm frozen to the spot, still clutching my manuscript tight to my chest. 'Maybe, you should get on your knees and start making it up to me right now.' He muses, sliding his fingers up the back of my thigh and under my dress. Finally, my instincts kick in and I pull away, stepping around him so that he's no longer between me and the door.

'Don't you dare fucking touch me!' I spit at him and his face darkens with anger

'Careful, little girl. I'm prepared to give you a second chance, but keep up the attitude and I might not be inclined to play nice.' He sneers, closing the distance I've put between us. 'Or maybe you'd prefer me to get a little rough?' he taunts with his head to one side, leering at me.

'Nice? Are you fucking kidding me?' I throw back. 'You were never nice -- you were a manipulative, predatory creep! I was just too stupid to see it! Not any more though, my eyes are wide open now.' I turn to leave.

'Jessica! Get back here now or I swear you will never publish that precious little book of yours.' He snarls. I turn back briefly and scowl at him with contempt.

'Watch me, Andrew.' I reply defiantly and head for the front door.

I practically jog to the main high street and flag down a taxi. Once I've flopped into the backseat, I let myself take a deep breath and try to stop my head from spinning.

ElizaGrey
ElizaGrey
272 Followers
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