Rich Pickings (4 page)

I finish by slowly rolling down my stockings and depositing those on my pile of clothing. Nude, I glance back at Dan for more instructions. Where would he like me to kneel?

By way of an answer he points to the spot right in front of him. I walk over there, and drop to my knees on the floor.

“I seem to recall you said you wouldn’t kneel at my feet.”

“That was before.”

“Before?”

“Before you promised to fuck me. And to take plenty of time over it. Only, not too much time, if you wouldn’t mind. Sir.”

He chuckles, reaching out to trail his fingers through my hair. “How impatient you’ve become. But you’ll have to wait a little longer. Do you know what this is, Summer?”

He reaches into his jacket pocket with his free hand and pulls out a small object. It’s vaguely cylindrical but with a narrow band close to one end, and made of some sort of plastic I’d say. It’s a rather fetching shade of lemon yellow. I look at it, then shake my head slowly.

“No, Sir. Should I recognize it?”

“Not necessarily. It’s a butt plug, Summer. And I think you know where it’s going. Don’t you?”

“Sir? I’ve never…” I’ve been managing to keep my eyes downcast, but I almost crick my neck as I tip up my chin to stare at him. I mean, I knew about anal play, but I thought we’d work up to it a little more slowly.

“I know you haven’t. But you have to start somewhere, and it might as well be here. Now. With this. I chose a small one for you, in deference to your sweet little virgin arse.”

“I see.” Said virgin arse is clenching desperately. I might throw up.

“You can thank me for my kindness and consideration if you like.”

“Do I have to, Sir?”

“Do you have to thank me? Or do you have to accept the butt plug?”

“Well, either I suppose.” I know I’m sounding vaguely mutinous, but really, this is all moving very fast. He’s thrashed me with a belt, and I managed to accept that. I’ve stripped on command and knelt at his feet. I’d expected things to become a little less challenging from here, but instead he piles on the pressure.

“Thanks are a matter for your own discretion. The butt plug’s not optional. But it won’t hurt you either. You
can
do this, Summer. And you can do it the easy way if you choose to.” His clipped tone is not terribly encouraging, especially when he points to the floor, indicating that I should drop my gaze.

I try to inject a suitable note of compliance into my next question. “Which is what, Sir?”

“You can lean forward, put your forehead on the floor and your bum in the air. Arch your back for me like I taught you in the lift. Then you can reach back and hold your buttocks apart while I lube you up. Then, when I tell you to, you can bear down while I slide this in. Nice and easy.”

“Easy for you maybe. And the hard way?” Too late, I try to bite back the insubordinate tone, but mercifully he doesn’t pick up on it. I know I need to watch that, though—it will do me no good.

“You can make a fuss, tense up, squeeze your arse shut and try to prevent me getting in. If you ask me to stop, you know I will. I’ll never force you to do anything. But I want you to do this, and if you want to please me, you will. And you’ll do it willingly, without protest. Do your best to help. And one last thing, Summer. Your body will have no trouble at all accepting this, once your head stops fighting. This is about surrender. Are you ready for that?”

“I’m not sure, Sir.” That’s the truth at least.

“Well, we’ll soon know. Lean forward, please.”

And I do. I actually stop protesting and I do it.

Dan walks behind me and crouches. I flinch as he caresses my left buttock, the red stripes still making themselves felt despite his gentle touch. But the pain is nowhere near as severe as I imagined it would be.

“Reach back with both hands and hold your butt cheeks apart if you would please.”

Ah, so polite. Wordless, I do as he asks. The slick coolness of the lubricant is oddly pleasant as he squirts it directly onto my exposed anus. I suppose he must have had that in his pocket too, though I don’t ask him. I’m too concerned right now with the unsettling sensation of having the lube worked into the delicate skin around my arse, and even inside the rim. I gasp as he slips one finger in, swirling it to smear the goo all around. He withdraws his finger, only to replace it with what I assume is the nozzle of the tube. He squeezes a generous amount directly inside me, and I squeal.

“Wimp. That didn’t hurt.”

I clench my bum in automatic self-defense, consciously loosening the tight muscle as he places his fingertip at the entrance again. I don’t want to resist, and I’m oddly reluctant to attract any fresh censure, no matter how gentle. “No, Sir. I’m sorry. It feels odd though.”

“Odd nasty or odd nice?” His words are accompanied by the penetration of one well-oiled finger, sliding easily inside my bum.

“Oh, Sir.”

I can’t help my startled moan, and he takes advantage of my apparent acquiescence to finger-fuck my arse. He isn’t rough with me, and is very deft about it, working the sphincter open to accept his presence more readily. I have to admit, he does seem very good at this, and he was right about my body accepting what’s happening. It feels strange, and distinctly humiliating, but it’s definitely not painful. Well, not yet. I start to revise that view as he inserts a second finger alongside the first. Now it’s tight, I feel stretched, less comfortable. Hurting. Getting scared.

“Tell me, Summer.”

“Tell you what, Sir?”

“Tell me.”

“It hurts, Sir. It’s scaring me now.”

“We slow down then. You were okay with one finger, right?”

“Yes, Sir. One was fine.”

“Like this?”

My body relaxes immediately as he reverts to just one finger, sliding it deep inside me and out again, each thrust hard and strong but no longer painful. I’m amazed, it was so easy. All I had to do was tell him.

“Okay now? Does that feel good?”

“Yes, Sir.” And it does. Incredible though that may be, it really does.

He shifts, reaching around and under me to strum my clit with his other hand. I groan my appreciation as my orgasm begins to unfurl. Helpless to resist, my pussy spasms in response as I lay my cheek flat against the rug under me. Dan takes that as his cue to up the ante once more, and slides that second finger into my arse again. This time, though, I’m fine. Bolstered by Dan’s quiet, confident efficiency, I’m even managing to relax and though it’s still tight there’s no sense of panic now. I gasp, but a couple of well-directed flicks across the tip of my clit soon restore orgasmic order. Moments later I’m climaxing hard.

Dan continues to thrust his fingers into my bum until the final waves of my release settle. He then pulls out, but only for a moment. Within seconds the cool hard surface of the butt plug presses against my now unresisting arse. It’s cool, but smooth, and less wide than his two fingers had been. It slides into my well lubricated and loosened arse with remarkable ease. My ring of muscle tightens around the narrow section, holding it in place. Dan circles my bum with his fingertip, nudging the protruding part of the plug to cause it to move inside me. I’m intensely aware of it, of each rocking, swirling motion. I groan, sinking my fingers into the deep pile of the rug. Dan gives the plug a couple of experimental tugs to ensure it’s not going anywhere. Then he stands and walks away from me. I hear running water, and crack open my eyes to see him washing his hands at the sink in the kitchen alcove. He finishes then turns to face me, a towel in his hands. He’s regarding me, his expression cold. I’m struck by how handsome, and how powerful he looks, towering there still fully dressed in his smart wedding finery. Whilst I grovel on the floor in front of him, naked, humiliated. And so aroused I could weep.

“Are you in pain, Summer?”

“No, Sir. I’m fine.” I mumble my answer through my disheveled hair but he hears me.

“In that case, what are you doing still on the floor? Kneel up. Now.” His tone is curt, and my contrition is instant.

I try to push myself back onto my knees, but each movement brings a wave of rather odd sensation deep inside my arse. Not unpleasant, but very, very unsettling. I’m not in pain, but still feeling delicate. At last, though, I’m back on my knees, my hands laid on my thighs palms up, my eyes directed toward a spot on the floor about a foot in front of me. And it’s that spot that Dan chooses to plant his feet as he comes back to stand over me.

“Look up, Summer. Look at me.”

I obey, regarding him through a shimmer of tears. I’m not sure why I’m crying. Maybe I’m not—not really. It’s just all so, so…overwhelming. He sees my emotions painted across my face. Of course he sees. He misses nothing. He crouches, now at my eye level. He wipes away a tear from my cheek with the pad of his thumb, but makes no other comment.

“Now for the fucking part. You were looking forward to that I think, my sweet little slut. Are you still of the same mind?”

I blink, shake my head briefly in an attempt to clear my vision if not my thinking.

“Yes, Sir. Please.”

He smiles as he cups my chin with his hand. “Good. You’ve done well this evening. I know that wasn’t easy, and I can tell by your face it still isn’t. But you haven’t whinged, haven’t complained. I’m very impressed. You deserve something nice now. Go into the bedroom and wait for me there please.”

He gestures with his head to a point somewhere behind me, presumably the bedroom, though I’ve yet to enjoy the grand tour. I was hardly through the door into the apartment before he ordered me to strip and kneel.

Obedient, I start to rise, but find this is not easy. Each time I move, so does the plug, sending waves of sensation through my arse. My cunt clenches, the hardness of the plug pressing against the soft walls of my pussy. I stagger as I try to stand, and might have dropped back to my knees but for Dan’s steadying hands under my elbows. Despite his chilled sharpness when he spoke to me a few moments ago he’s all concerned kindness now, gently easing me onto my feet. I cling to his arms, aware once more of his pristine fully dressed elegance in sharp contrast to my own state of naked vulnerability.

But I feel safe. Totally safe. And very enthusiastic about what’s to come.

“Go on. I’ll be with you in a minute.” He turns me and points to a door across the room. He drops a kiss onto my shoulder and pats my still tender bum.

And I start to move. My progress is slow, decidedly unsteady, but I’m determined to get to the bedroom. As he says, I’ve earned it. As I reach the door Dan calls his final instructions to me.

“Face down on the bed. There are restraints on the headboard. Please slip those around your wrists and I’ll tighten them in a moment.”

Chapter Three

Two things strike me immediately as I enter the bedroom—two dominant features. First, the bed, which is huge and looks to be made of solid oak does indeed sport leather straps attached to the headboard. It is oddly positioned in the center of the room. A large chest, also oak by the look of it, sits at its foot. The duvet is a plain, deep red which matches the carpet.

The second striking feature is the St Andrew’s Cross positioned against one wall, huge and sturdy and constructed of a dark, warm looking wood. The last time I saw one of those my friend Freya was strapped to it, naked and blindfolded, in the club in Lancaster. I have a strong suspicion I will become intimately acquainted with the capabilities of this particular item of equipment myself, if not this visit then soon. But not now. Not immediately. Dan promised me something rather nicer. I turn my back on the cross and, courtesy of the plug nestled conspicuously in my bum, clamber somewhat awkwardly onto the bed.

I only just have time to wriggle into position, my wrists threaded through the loose leather straps, as Dan enters the room. He closes the door behind him then leans against it to survey me. I turn my head to look at him, uncertain whether I should smile, speak, make eye contact or what.

Dan settles the matter by flashing me a dazzling smile. “You look absolutely beautiful, your bottom striped from my belt, my plug up your arse.”

“I, I feel good. Sir. I think.”

“You think?”

“A little sore. Your belt is heavy, Sir, and I didn’t like having the plug put in. But I’m glad I did it.
We
did it, I mean…”

“You can thank me if you like, for my time and attention in teaching you how to do these things. And if you’d like to offer your apology again for yesterday’s display on my brother’s front step now might be a good time.” His smile is warm as he strides across the room toward me, despite his stern words. And it all seems so easy, suddenly.

“Yes, Sir. Thank you, for teaching me. And for helping me. And especially for slowing down when I was finding it hard. I did appreciate that, really. And I am truly sorry for what happened yesterday. I can’t believe I did such a thing. It’s just not me, it really isn’t. Even before you beat me with your belt I was deeply ashamed.”

He sits beside me, trails his fingers slowly across my shoulder and down my spine. It feels wonderfully sensual and I raise my hips as he reaches my bottom. Maddeningly, he stops there. “You’ve accepted your fault, and your punishment.” He traces the lines on my bottom by way of emphasizing his point. “And I get the impression you’ve learnt from the experience. There’s no need for you to feel ashamed now. It’s done. We’ve moved on. It’s what you do from here that matters, not what happened in the past.”

If only everything could be so simple.

“Thank you, Sir.” I whisper my response as he continues to caress my throbbing buttocks. He reaches for the straps to tighten them around my wrists then seems to think better of it.

“I’ve changed my mind. I think I’d prefer you on your back. Roll over please.”

I do so without hesitation, although the pressure on my bottom as I settle my weight again is uncomfortable, both inside and out. Without waiting for his instruction I place my hands back in the restraints, and this time he tightens them around my wrists. He tests the fit to make sure I’m securely held but my circulation is not compromised. Needless to say, he is entirely satisfied on both counts.