Learning the Rules Ch. 05

[Hello lovers! Here comes chapter five of eleven...

This one's a bit of a quickie, to set the scene for what's coming next, so sorry not sorry for the slight tease... I'll make it worth the wait ;)

Enjoy!

EG x]

As I stand waiting on Mr Swift's doorstep the next evening, I find myself feeling excited. Not just to see him, though I am, but to find out what my training will involve this time.

When he opens the door, my breath catches in my throat at the sight of him. He's dressed all in black, from his expensive looking suit to the shirt underneath, to the silk tie he's just finished tying, adjusting it as he ushers me in,

'Jessica! A pleasure to see you again.' He smiles,

'Likewise.' I manage, then 'Have I got the time wrong? You look like you're heading out.'

'I am!' he replies, 'We are.' He smiles, but first, let's take care of the formalities.' He raises his arm towards the stairs, 'I'll be with you in five minutes, take off your coat, but do not get undressed until I join you, understood?' I nod mutely and make my way up the stairs.

As I kneel by the foot of the bed, still wearing my floral dress, I wonder if this keeping me off balance is all part of the training? Expect the unexpected? I don't have long to wonder as I hear Mr Swift coming through the door. He crosses to me and lifts my chin gently so that I'm looking at him,

'Jessica, what are your safe words?'

'Yellow and Red, Master.'

'Good girl. Take off your underwear and bend over the dresser.'

Okay, this part I can do. But why am I still dressed?

I step out of my panties and cross to the dresser, assuming the now familiar position, though it feels much less indecent when I'm mostly clothed.

Mr Swift retrieves something from a drawer and crosses to show me. It's another new butt plug. It's shiny and black with a clear sparkling jewel at the base, and it's significantly bigger than the gold one he used yesterday.

'Tonight, I would like to fill your pretty little ass with this. Would you enjoy that, Jessica?' he asks with a smile.

'Um, Yellow.' I breathe quietly. Immediately he puts the monstrous looking plug to one side and stands me up straight to look at him.

'Well done for using your safe word, Jessica.' He smiles kindly, 'Tell me what's worrying you.'

'It's just,' I start, 'It's huge. Much bigger than the one you used yesterday, which felt enormous, I'm just really not sure I can.' I shrug

'It's certainly a challenge. But it's one that I think you're up to, and that you'll enjoy.'

He hands me the challenge in question, 'as you can see, it's rubber, not metal, so although it's bigger, it's also a little lighter, and much more flexible.' I play with the toy a little and realise he's right.

'If you'd like, we can start with your gold plug, and I'll use the black one in your pussy so you can get a feel for it, then maybe try it in your behind, or, we can stick to just using the gold. What would you prefer, Jessica?' he says, as though he's asking if I'd like to try oat milk in my latte.

I wrap my fingers around the black plug, they just barely make it all the way round, but it's actually quite flexible.

'I'd like to try, Master.' I say with as much confidence as I can muster.

'Good girl. Get back in position.' He smiles.

I do as I'm told and take a deep breath as I bend back over the dresser. A wave of pleasure rushes through me as he eases my dress up and over my back, smoothing his palm over my behind. He picks up the gold plug,

'Open your legs Jessica,', I do as he says and feel him push the tip of the familiar gold toy against my wet pussy. It glides inside me easily, but he works it back and forth a few times to make sure it's well lubricated before sliding it up against my tighter little hole. Without warning, he pushes the gold plug straight into my ass in one fluid motion, making me moan blissfully.

'Feel good, Jessica?'

'SO good, Master!' I pant

'And so easy, I think you underestimate yourself Jessica.' He says, sliding his thumb in against the plug to make his point, and make me pant harder. 'Are you ready to try the black one in your pussy now?' he asks, working his thumb in and out of my ass, the gold plug still in place,

'Yes please, Master.' Keeping his thumb where it is, he retrieves the huge black plug with his free hand and presses the tip against my wet lips.

'Take it as slow as you need to, Jessica.' He says calmly, still fucking my ass with his thumb as the black plug stretches my pussy wider.

I am pure sensation as I find myself rocking my hips to meet his thumb each time, willing him to fuck me deeper. With another wanton moan, I push back against him impatiently and my wet pussy takes the black plug smoothly to the base.

'Oh Master, that feels incredible!' I breathe

'I knew you'd enjoy having both your sweet holes so full.' He replies, working both toys in and out of me in time. 'Would you like to try it in your ass now, Jessica?' he asks, moving it firmly in and out of my pussy, making sure it's as slick as possible. Sink or swim time, Jess, I think to myself.

'Yes, Master. Yes please.'

'Good girl.' Slowly, he removes his thumb and then the gold plug from my behind, in a heartbeat, it's replaced with just the tip of the black plug and I back against it before I can chicken out. He stills me with a hand on the small of my back.

'Easy, Jessica, take your time.'

I breathe deeply and rock my hips again, taking the same portion in and out a few times, getting used to how wide it's stretching me.

From nowhere, I feel his fingertip on my clit and almost come without permission on the spot. I wail with delight, bucking back against him, and the huge black plug slides all the way into my eager ass.

'Would you like to come for me, Jessica?' I can hear a smile in his voice as he continues to gently circle my clit,

'Oh yes please Master!' I wail,

'Then do.' He curls two long fingers inside me and I come hard around them, and the huge new plug in my ass, throwing my head back in complete ecstasy.

As my breathing starts to return to normal, he twists the jewelled base of my new plug a few times, making me almost purr in contentment.

'Are you happy for me to leave this where it is while we go out, Jessica?' he asks. Shit, I completely forgot we were going out. In the car? Will I need to sit with this in me? Will I even be able to?

My own stubborn determination starts to kick in... plus something else. I realise I have an overwhelming urge to please my Master. And my new plug already feels so much easier.

'Yes, Master.' I reply with a smile and he mirrors it back at me.

'Excellent. Then let's get you dressed.' I look from my dress to him and back again, confused. 'You look lovely, Jessica, but it's not quite right for where I'm taking you tonight.'

Oh.

Immediately I've all but forgotten about the intrusion in my ass in favour of wondering where we're going?

'I'm going to call us a cab, you may choose anything you'd like from the wardrobe and meet me downstairs in ten minutes. Understood?'

'Yes, Master.'

When he leaves, I take a deep breath and tentatively cross to the wardrobe, bracing myself for how the huge plug in my ass will feel when I move. It feels strange, but definitely not unpleasant.

I dare myself to clench my cheeks around it and when I do, a jolt of pleasure spreads straight to my clit, making me gasp.

Alright. I can do this.

I open the wardrobe to see what my options are and quickly realise it's unlikely Mr Swift is taking me to another fancy restaurant.

Most of the "dresses" are little more than lingerie -- indeed, some of the options actually are lingerie, and very sparse examples at that. So much for Mr Swift not being into subs in kinky little outfits. Does he seriously expect me to leave the house wearing one of these?

Yes, Jessica, he does -- and you're probably down to about seven minutes left to choose, so let's hurry it up, I think to myself.

I spot a little strappy black satin dress that looks slightly less obscene than the rest of the choices available and slip it off the hanger. Realising my white lingerie will look ridiculous underneath it, I strip naked and wriggle into the new dress. It's skin tight and barely covers my pussy, clinging snugly across my thighs, but the fabric does feel gorgeous against my skin.

I step back to have a look in the full-length mirror and decide that actually, it looks great. Slutty, but good. I twist to have a look from the back and gasp -- there's a little heart shape cut out -- right on my ass, perfectly positioned to show off the sparkling base of the monster plug in there.

Shit. So much for less obscene.

Increasingly aware that I'm running out of time, I decide it'll have to do and quickly dismiss bothering to look for any replacement underwear. I throw my coat on over the top and hurry downstairs.

* * * * *

I sit with Mr Swift in the back of a large black Audi, grateful for the privacy screen that cuts us off from the driver.

'Now, Jessica.' Mr Swift starts and I turn to look at him.

'As I've told you already, Dominants have a wide variety of tastes when it comes to how they enjoy their submissives. It would be impossible to teach you about all the possibilities within our week together, but it is vital that you experience at least some of the variety that will be expected of you, should you start working for Crystal.' He tells me

'That makes sense, Master.' I nod, feeling both anxious and excited to find out what it means

'To that end, tonight, I am taking you to a BDSM club.'

I had suspected that might be the case, but hearing him confirm it makes me swallow nervously. He calms me with a strong hand on my bare thigh.

'Don't panic Jessica, you will be there purely as my submissive, to observe. I will not expect you to perform publicly, or to serve any other Dominants this evening, understood?'

'Yes, Master.' I reply quietly. Very aware of the unspoken implication that he may expect me to do those things on another night.

'You can still use your safe words at any time, but other than those, I will expect you to speak only when asked to, and to follow my instructions without hesitation. Alright?'

'Yes, Master.' I nod again, feeling a flutter of anticipation between my legs.

'The other most important lesson you will learn tonight, is discretion.' I narrow my eyes a little, not really understanding. 'In the club we're going to, you will likely observe things that shock you, or make you uncomfortable, perhaps even disgust you. But you must remember, that everyone in attendance is there of their own free will, to indulge their kinks in a safe space, free from judgement.'

'So, live and let live, I guess?', he nods.

'Exactly that. By all means, make note of anything you'd like to add to your hard limits - you should never partake in anything you're not comfortable with, but shaming someone else's kink is equally unforgiveable.' I nod, digesting the information and wondering just what sort of madness might be going on in this club.

'Excellent. Now, we're almost there, take off your coat.' I look up at him, alarmed and he regards me impassively.

'Jessica, there is plenty of space in this car for me to discipline you before we arrive at our destination.' He warns mildly.

'Yellow.' I whisper softly and his expression changes in a heartbeat.

'What's troubling you Jessica?' he asks

'Um, my dress. It's rather revealing at the back.' I tell him awkwardly and he smiles.

'I'm aware of that, Jessica, but you needn't worry. The club has an underground car park and entrance, there will be no public exposure, I assure you. And trust me, once we're inside, you will likely find yourself decidedly overdressed compared to most.' He smiles reassuringly, then adds, 'And as your Dom, it will please me a great deal to see your new plug displayed so invitingly.'

I feel myself blush at his words, but I can't deny that the thought of pleasing him turns me on. I take a breath and shrug out of my coat, draping it neatly on the seat beside me.

'Good girl.' Mr Swift smiles proudly, stroking my hair. I find myself leaning into his touch. 'One more thing,' he continues, 'I need you to wear these.' He finishes, producing a pair of black leather cuffs, held together by a length of silver chain threaded with red ribbon. I feel my eyes widen.

'I know that I haven't taught you much about restraints as yet, but it's a requirement of the club management that submissives be at least lightly bound at all times, so as to avoid confusion.'

'So that the subs know their place, you mean?' I say before I can stop myself, 'Sorry, Master. I didn't mean to answer back.' I add quickly, looking down. He tilts my chin back up to make me look at him,

'Don't apologise, Jessica, you're quite right. But these aren't terribly restrictive, and I'll cuff your wrists in front of you so that you'll still be able to move freely. The red ribbon shows that you are mine alone, not accessible to any other Doms without my express permission.'

Almost on autopilot, I lift my wrists together in front of me.

'Good girl.' He says, binding them together in the cuffs. 'You're doing exceptionally well, Jessica.' He tells me, grazing his thumb gently over my bottom lip. I feel my mouth curl into a small smile as the car comes to a stop.

'Ready?' he asks, bowing his head to look into my eyes.

'Yes, Master.' I reply softly.

Mr Swift takes hold of the chain connecting my bound wrists and helps me out of the car. Almost instantly I feel the cool night air against my exposed ass and my cheeks clench involuntarily around the plug buried in it.

'You made an excellent choice of dress, Jessica.' Mr Smith tells me as his fingers glide across the base of the toy, giving it a sharp tap that makes me gasp.

'Thank you, Master.' I reply demurely with my eyes cast down as he leads me inside.

[Your thoughts & comments are welcome as always - chapter six will be up soon! EG x]