Toying with Lily

In my experience, women who seek a sexually submissive role are often people who are dominant and forceful in their daily lives. They do not slide meekly into a submissive role. There has to be dominance before there is submission. This story gets you inside the head of a Dom with a fiesty Sub and shows what it takes to be in charge.

“Toying with Lily” appeared in “Hurts So Good” Alison Tyler (ed.), Unrestrained Erotica (Cleis).

It was a finalist for the 2009 John Preston Short Fiction Award. The John Preston award is given by the US-based  National Leather Association: International (NLA-I), a leading organization for activists in the pansexual SM/leather/fetish community

Toying With Lilly

© Mike Kimera 2008

The jeans are a deliberate act of provocation. Lily, my allegedly submissive, “You can do anything to me. Anything at all. I’ll even call you, Daddy while you do it.” mistress, likes to test my limits by defying me.  She wants to see what I will put up with and what I will do to keep her in her place. She likes to be kept in her place.

At the moment, her place is standing in front of my chair with her hands behind her back and her head held high, waiting for me to flog, pinch, spank and fuck her to orgasm. We both know that by now she should be naked. Instead, she has chosen to present herself wearing tight-fitting jeans and a sly smile.

True, Lily is impressively naked above the waist. She is a fully fleshed woman, short without being in any way small. Her breasts are large and heavy, and when, as now, she holds her hands behind her back, they push out almost aggressively. Her stomach is soft and flows over the cruelly tight fastening of her spray-on jeans. At any other time, I might have relaxed back into my chair and considered whether to start by using the soft calf-leather hand-lash on her belly or by suspending weighted clamps from her nipples.

But now my focus is on her jeans and the smile that accompanies them.

I could just tell her to take them off.

Or I could throw her onto the bed, wrestle them from her, maybe even cut them off her, and then raise welts on her substantial buttocks with the crop.

But then I would be doing the obvious, which means I would lose the initiative and, if that were to happen often enough, I would lose Lily.

I don’t want to lose Lily. She makes me feel alive in a way that no one else does.

I rise out of my chair silently and lean forward until I am almost touching her.

I, of course, am fully dressed. This is the middle of the business day. A suit and tie are de rigueur.

For a moment, I see myself as the Evil Victorian Headmaster about to inflict punishment on the Vulnerable Pupil. My cock salutes the image, but, although Lily is fourteen years younger than I am and although I am stronger and larger than she is, she does not look vulnerable.

Her smile is still in place. She is daring me to do something to her. Bracing herself in pleasurable anticipation of my assault.

I push my thumbs into her jeans at each hip, grab the denim and pull upwards until Lily is forced onto tiptoe and much of her weight is on the seam of the jeans that is riding up into her. She has the good grace to keep her unbound hands behind her back and let herself fall against my chest. The small groan that escapes her makes me smile.

I lower her until her naked feet are flat on the floor and then use her thick, wavy hair to pull her head all the way back. She is still smiling, damn her.

I push my tongue deep into her mouth. Before she can respond, I release her and step away. I want her to feel my absence for a while.

Turning my back on Lily, I face the coffee-table on which she has laid-out the bondage gear. It is a tradition with us that she arrives at the hotel first, bringing her toys with her. I can tell the kind of satisfaction she is seeking from the “pallet” that she presents me with. I make my selection and resume my seat in front of Lily.

I’m pleased to see that she has not moved and that her tight jeans now display an impressive camel-toe. But what pleases me most is the surprise she shows when I fasten the ankle-cuffs of the spreader-bar over her jeans.

The whole point of the spreader-bar is to keep Lily open to me, so using it when she is wearing jeans would appear to defeat the purpose. I’m sure that Lily is bursting to ask me what I intend to do but then, of course, she would lose our game and so she remains silent.

“Turn,” I say, slapping, Lily on the thigh. Legs forced wide apart, she turns awkwardly and slowly, making her breasts swing in an ungainly way that I find perversely satisfying. When she has her back to me, I rapidly put a cuff on each wrist and then fasten the cuffs together, keeping one wrist above the other. We both know that I could have done this without making her turn, but that would have been much less fun.

Lastly, I stand and fasten the collar around Lily’s neck. The collar that Lily had laid out for me covers her entire neck and has a lip that pushes upwards under her chin so that it’s almost impossible for her to move her head. I know from this that Lily needs a hard session that forces the orgasms from her. Lily had already attached a leash to the front D-ring of the collar, inviting me to make her my bitch and drag her wherever I need her to be. She is indeed a treasure beyond price. Nevertheless, she is a defiant treasure who needs to be brought in line, a process I am now ready to start.

“It was thoughtful of you to keep your jeans on,” I say, closing my hand around Lily’s collared throat and forcing her back against me. I have large hands and I have often used them to deprive Lily of air at crucial moments. “I’m sure it’s a polite way of letting me know that you don’t need to be fucked today.”


The word escapes before Lily can stop it. Remaining unfucked is one of the few punishments that would really make Lily suffer. To paraphrase Rhett Butler, Lily is the kind of woman who needs to be fucked often and by someone who knows how. That’s one of the reasons she is here with me instead of with her loving husband: I know how.

I also control when.

“How many days has it been now, Lily?”


I’m impressed. According to the rules, Lily is not allowed to have an orgasm for two days before we meet. It gives our meetings an edge. Four days of restraint will have honed Lily’s hunger to a razor’s edge. And yet she couldn’t resist defying me by keeping her jeans on. Still, if Lily could move in a straight line from need to satisfaction she wouldn’t be dependent on someone like me to bind and beat her along the path to release.

“So, you haven’t come in four days,” I say, bringing my left hand down from Lily’s throat and closing my fist around her breast, digging in my fingers hard enough to bruise the flesh. Lily stiffens at the pain, holding her breath in anticipation. “And yet you keep the jeans on to keep me out.”

With my right hand I pop open Lily’s jeans and pull down the zipper. Lily sighs happily and seems to be certain that she knows where my fingers will go next. Lily has a prominent and sensitive clitoris that reacts dramatically to being bitten or pinched or flicked hard with a fingernail. I slide my fingers in that direction, feel her arse clench against me as she prepares herself, and then I surprise her by reaching up for the leash and pulling hard until she is bent double at the waist.

Lily’s size makes it an effort for her to bend like this. Her legs are tensed to take the strain and the blood is already rushing towards her head. Her breasts hang, heavy and full, like udders needing to be milked. Being a generous man, I help her maintain her position by tying the end of the leash to the spreader-bar.

Roughly and with some difficulty I roll Lily’s jeans down off her wide arse until her sex is exposed. I brush the tip of my finger across her slick lips and breathe in the earthy scent of her arousal. Lily groans. It takes all my restraint not to enter her then.

Instead I move round in front of Lily and, reaching into my jacket, I remove a small velvet bag.

Lily sways slightly, straining with the effort of trying to look up at me from her bent-double position.

“What are you doing?”

Wet both know what she means is, “Why aren’t you fucking me?”

I take two silver cigar-shaped cylinders out of the velvet bag. They are each about the length of my index finger but twice as thick. I hold the cylinders directly in front of Lily’s face.

“These are a delightful idea, Lily. I picked them up on my last trip to Japan. An executive sex-toy… just like you.”

“Bastard,” Lily spits at me.

“A commonly held view,” I reply.

“At first they look at little like Benewah balls don’t they, Lily? I know: been there, come on that, but notice the wires at the end of each cylinder. They attach to this nifty little control that enables me to control the speed that each of them vibrates at.”

Lily does not look impressed. She’s taken on bigger toys than this in her time.

“Size isn’t everything, Lily, persistence counts and these things have long-life batteries. They can keep a bunny buzzing all night long.”

As I talk I slip a condom over each cylinder

“Why two condoms, you’re wondering. Work it out, Lily.”

Her eyes widen. Lily is not a fan of anal sex.

“You wouldn’t…”

We have been down the road less traveled by from time to time but for Lily this has been more a price she has paid than a pleasure she’s sought. I want to change that. The image of Lily begging to be sodomised feeds some of my darkest hungers.

“I will, Lily. And before I untie you today, you will thank me for it.”

Moving quickly, I step behind Lily to put the toys in place. Lily’s labia are short and swell into ridges like the runners on a sledge when she is aroused. I help the swelling along by pinching one lip hard between my finger and thumb and pulling it sideways to give me access. I push the first cylinder all the way in. It’s a bit of a struggle to get all my fingers, my thumb and the cylinder inside her but I am very well lubed and I persevere until I feel the cylinder touch the cervix. Lily’s knees buckle slightly at the contact and only the fact that so much of my hand is in her keeps her upright.

To her credit, Lily regains control quickly and without complaint, pushing hers arse up and back, taking the rest of my hand into her up to the wrist in the process. Lily loves to be fisted. Something in the brutal power of it appeals to her. If I give way to her now, she will quickly fuck herself to an orgasm.

With my free hand, I slap Lily hard across the arse to bring her to a halt. Then, slowly but determinedly, I extract my hand. The wire from the cylinder hangs obscenely from Lily’s still-gaping cunt.

“Please,” she says, her voice slightly ragged.

“The word I’m waiting for is Thank You, Lily”

“That’s two words”

I smile at the fact, that even bound and fisted, Lily refuses to yield.

“Then perhaps a second cylinder is what’s needed to produce them?”

Without waiting for a response I force my cunt-slickened thumb into her arse. It’s a very tight fit.

“Resisting will just make this worse, Lily.”

The muscle around my thumb tightens its grip.

I sigh with feigned disappointment, then I work the thumb in a slow but firm circle until the muscle relaxes a little. I slide the second condom-covered cylinder beside my thumb and push. Lily cries out at being stretch so but I work quickly, thumb and cylinder soon swap places and Lily’s rose clamps shut around the thin wire that goes to the control.

Bent over, bound, with wires dangling from both holes, Lily looks delicious.

I’d like to savour the moment but Lily has started swaying her hips from side to side as if she can shake the toys loose. I need to move us on. With as much economy of movement as possible, I release the leash from the spreader bar, pull Lily upright and then drag her jeans back up until her arse is once again clad in denim. I even manage to refasten the jeans and pull up the zip. The control hangs from the top of Lily’s jeans like a tail.

“What are you DOING?” Lily is not happy. Lily wants to be fucked not dressed.

“Teaching you what happens when you defy me, Lily.”

Then I turn on the toys.

Lily twitches like a fish on a line. I wrap one arm around her chest, pressing her back against me to keep her from falling. I’ve set both cylinders to high. Even covered by the jeans, I can hear their buzzy engines working away.

“You’re killing me!”

“No, Lily, I’m helping you. But I’m a reasonable man. I’m setting the one in your cunt to low so that it’s not too distracting.”

The noise abates a little. Setting the toys this way will keep Lily focused on her arse and make it less likely that she’ll come quickly.

I wrap Lily’s leash around my fist and then let go of her chest. Before she can regain her balance, I drag her after me towards the bed. The spreader-bar makes her stagger and it’s all she can do to keep up.

Lily and I use a boutique Edwardian-themed hotel in Bloomsbury for our trysts. Part of the appeal is that the repro ‘gentleman’s club’ furniture is so bondage friendly – a bit like the gentleman’s clubs were themselves, I expect. My favourite feature is the four-poster bed. Something of an anachronism for a room like this but I’m more than willing to forgive the style lapse in favour of the practical advantages the bed offers.

I push Lily up against one of the posts at the foot of the bed, and tie the leash around it at neck height. To keep her upright I slip a line through the belt loops of her jeans and cinch it tight to the post and I tie the middle of the spreader-bar to the dragonball foot of the bed.

Lily immediately pushes forward so that her breasts jut out either side of the post. This is such an appealing sight that it takes me a couple of seconds to realize that Lily is humping the post, trying to get off and to distract herself from the insistent little agitator in her arse. This will not do. I put an end to her hopes by sliding an overstuffed cushion between her and the bedpost. Lily shouts her frustration in a string of curses that would make a docker blush. I do not tolerate shouting. Lily knows this. I remind her of my views by closing one hand over her mouth and using the other to force her nostrils shut. After a few moments the noise stops and I release her.

I’m hot, slightly out of breathe and I have an erection I could hammer nails with. It’s time to get comfortable. I hang my jacket up, take off my tie, unbutton my collar, slip off my shoes, and climb up onto the bed in front of Lily.

My day to day life is filled with plans and deadlines and checklists. My time is accounted for months in advance. These sessions with Lily free me from that. In these little islands of lust and wickedness, I eschew all planning, listening only to my instincts and Lily’s needs. If I can maintain my focus, my actions and her reactions can fuse into a single dance of restraint and release. Today we both have a powerful need for that release.

So far, Lily’s defiance has set the scene. Now it is time for my desires to lead us in the dance.

If I listen to my blood-engorged cock, then I would fuck and fuck and fuck until neither Lily nor I could move. But my cock lacks judgement. I know that my enjoyment will increase as I bring Lily closer and closer to abandoning herself, to letting go of everything except me and my will. Then I can drive us both into that moment when pleasure is all there is.

Putting conscious decision making aside, I focus on Lily.

She is slumped against the bedpost, hair sweat-damp against her forehead, breasts splayed around the phallic bedpost, legs forced wide apart by the spreader-bar and arse pushed out an inviting angle. All in all she’s looks wonderful.

I kneel up on the bed and brush Lily’s hair back off her forehead. She closes her eyes. Gently I kiss each eye, letting the tip of my tongue brush lightly across her eyelids. Then I place both hands on either side of her face, close my eyes and kiss her on the mouth.

When I pull back and open my eyes, Lily is looking at me. She is waiting calmly now. She knows the dance is about to begin.

I lean close to her, my mouth at tracing the line of her jaw, my arms around her waist.

I murmur her name and feel her body relax against me. I kiss my way down her body and suck one of her nipples deep into my mouth. When I’m certain the all the tension is gone from her, I find the control hanging from her jeans and reset both cylinders to high. Lily jolts upright and tries to pull away from me. I hold her in place by biting down hard on her nipple, then I spend a delightful few moments randomly resetting the speeds of cylinders, playing a tune with the buzzing they make and using my teeth to create a contrapuntal beat of pain in Lily’s nipple. She rises up on to the balls of her feet but succeeds in not crying out. I set the cylinder in her arse to high and the one in her cunt to medium and then I stand up on the bed.

Lily is glaring up at me, mouth firmly closed as she concentrates on ignoring the sensation caused by the toys.

I smile at her and release my cock and balls from my trousers. I keep the trousers on because I enjoy the constrained freedom and because the image of naked arousal blossoming from Saville Row pinstripe pleases my sense of the absurd.

I’m now at just the right height to use Lily’s mouth. At one time this would have required a ring-gag. Not that Lily came to me innocent of the joys of oral sex but she was used to “giving head”, a process that allowed her complete control. I was more interested in taking than letting her give. Very little matches the satisfaction of a good face fuck. Under my tutelage, with her wrists bound behind her back and a ring gag in place, Lily learnt to surrender herself to my use. Now her throat is always available to me. All I have to do is slap her face with my erection and Lily opens her mouth wide and offers her tongue as a slipway on which to launch my violent lust.

Lily knows what I’m about to do but she keeps her mouth defiantly closed. It takes three hard cock slaps across her cheeks before her mouth opens. I position my erection on her tongue, grasp her jaw and the back of her head and force myself into her mouth. The angle is not the easiest and my cock is proving itself inflexible but I manage three firm strokes, the last of which gets almost all of me into her mouth. I hold her head in place until I see the tears forming in her eyes, then I pull out. Lily wretches and copious amounts of spittle slips over her chin and onto her breasts.

“Be a good girl for Daddy,” I say pulling Lily’s head back so she is looking up at me. “Beg me to sodomise you.”

Lily is still getting her breath back so she shakes her head firmly and waits to see what I will do next.

This time it takes four cock slaps before Lily’s mouth opens. I slip my index fingers into either side of her mouth and use my thumbs to push my balls past her lips.

“Work your tongue, Lily. Suck like you mean it. I know you’ve had the practice.”

Lily’s eyes narrow in distaste but she works my balls nonetheless. The sensation itself is not particularly exciting, although seeing my erection rest on Lily’s face while she struggles to please me is entertaining. As with so many pleasures, context is everything. In this case the context is set by the fact that it is not my balls that Lily has been practicing on.

I think it’s only fair that, if you are going to fuck another man’s wife, he should get some benefit from it. Alan, Lily’s husband, is man of simple sexual needs who, over the two years of my association with Lily, has found his sex life becoming more complex. First I had Lily habituate him to letting her film their fucking. She told him it turned her on. True enough in its way. She has come many times while replaying the film on the state of the art LCD screen the hotel thoughtfully provides. I like to try to beat a come out of her before her husband’s on-screen performance ends with him collapsed on top her. Initially this didn’t give me a lot of time but I usually managed it.

After a while I had Lily insist on being on top, facing towards the camera when they fucked. I’d grown profoundly tired of watching Alan’s arse, the sight of Lily bumping and grinding and pulling at her breasts was a decided improvement. It also had the benefit of making the fucking last long enough for me to do a more thorough job of beating Lily during the playback. Besides, with Lily facing the camera, she could mouth “Thank you, Daddy,” before each sticky dismount. It’s our way of sharing.

Recently, I’ve spiced things up a bit by phoning Lily before each session with Alan and telling her how I want her fucked. At my bidding, Alan has been introduced to the delights of having his balls sucked and his arsehole rimmed while Lily jacks him off onto her substantial tits. Alan never lasts long but he is extremely grateful. Lily on the other hand, finds these sessions very frustrating. When Alan is happily asleep, I call Lily and make her fuck herself for me in front of the camera while Alan’s drying cum puckers the skin on her breasts.

Now Lily is sucking my balls when she would rather be fucking. I’m sure the message is not lost on her.

When my balls are wet I pull them out of Lily’s mouth but leave then resting against her cheek.

“Ask Daddy, to ream your arse, Lily, there’s a good girl.”

“Please, Daddy,” Lily says, “Fuck me hard and deep.”

I smile. Progress.

“But use my cunt. It’s wet and it aches for you. Please, Daddy.”

Not enough progress. Time to change tactics.

I climb down from the bed, my cock swaying absurdly in front of me, and set to work on detaching Lily from the bedpost. Leaving her hands cuffed behind her back and the spreade-bar in place, I wrap the leash around my fist and pull her roughly down on to the bed so that she’s lying on her back with her legs spread.

She can’t help but grin as she bounces on the bed. Lily is anticipating getting fucked. I’m anticipating taking her breath away.

It seems the constant stimulation from the toys has had an effect; the crotch of Lily’s jeans has been darkened with moisture. Instinctively, I lower my head to investigate. Lily lifts her hips, offering herself to me. Now it’s my turn to grin.

I place my hands on her thighs and push them even further apart. Quickly and without warning, I bite down hard on Lily’s mound. Lily thrashes beneath me, too shocked even to scream. I bite a second time and she stiffens, back arched. The third bite does it; Lily’s first orgasm rides her like an epileptic fit.

When the shaking stops, I grab the spreader-bar and use it to force Lily to bend her legs until her knees are pressing into her breasts. I’m bent over Lily, inches from her face, tying the leash to the spreader-bar so that she will remain folded, when her eyes open.

“You BIT me.”

There is as much surprise as anger in her voice.


“THREE times”

Indignation seems to be loosing out to incredulity. I finish the knot that will keep Lily bent double, kiss her forcefully on the mouth and say, “It seemed like the right number.”

“You are a sick, twisted, freak.”

“And your point is?”

“Fuck me. Fuck me right now. Please.”

I stand up and start to undress, slowly, carefully folding each item as it is removed.

“Come ON.” Lily says, rocking a little, testing the strength of the knot that holds her.

I still have my trousers and shoes on. I will not tolerate being hurried.

I grab the spreader-bar and push down until it rests quite firmly against Lily’s neck. A little more pressure will deprive Lily of air. She becomes very still. Her eyes widen.

I’m fairly certain that there is a part of Lily that wonders if, one day, I will go to far, step off the ledge of safe, sane and consensual and freefall into the unbridled violence. I know there is a part of me that asks that question. Finding out the answer afresh is part of the frisson of our little sessions.

“You will be quiet now, Lily,” I say. My voice is level and calm and all the more menacing for that. “You will not speak until after I have fucked you.”

I can see that Lily wants to ask a question but she restrains herself.

“Good girl,” I say.

I stand where Lily can see me while I finish undressing. Her eyes never leave me.

When I move to the coffee-table to pick up what I need, she loses sight of me. She doesn’t see the knife until I climb back on the bed.

We both know the knife is very sharp. We keep it that way in case I need to cut through any bonds in a hurry. I run the blade across my thumb. Blood blossoms bright and fast. I push my thumb into Lily’s mouth. She doesn’t need to be told to suck.

“You should have taken the Jeans off, Lily,” I say, running the knife flat along Lily’s breast until the blunt side of the blade presses against her nipple. Lily stops sucking. As far as I can tell, she stops breathing.

I withdraw my still-bleeding thumb and move the knife between Lily’s legs, placing the tip against the seam of her jeans. Lily closes her eyes but she does not scream and she does not try to move. I’m proud of her.

I think about what it would mean to try to cut off these skin-tight jeans with this knife. The pain it would cause. The blood that would flow. I look inside myself to find my desire.

Nope. Not my thing. What I want to do with the woman below me is show her what it feels like to be fucked in the arse by a man showing the appropriate level of enthusiasm.

Lily still has her eyes closed when I put the knife down on the bed and start to manhandle her jeans. It isn’t easy but I manage to get them undone and drag them down Lily’s legs until they are bunched at her knees and her arse is exposed.

Lily’s sex is soaked. The rich earthy smell of her arousal floods my senses, making me salivate with need.

I bend closer, breathing her in. Only then do I notice the cylinder control hanging out of her.  I’d almost forgotten about them in all the excitement. I reach down and turn them both off.

Lily opens her eyes and grins at me.

On her back, bent double, legs forced apart by the spreader-bar that is still tied to her collar, toys in each sweat-slickened hole, Lily is an invitation to wickedness.

I’m not in the mood for finesse. I tug the cylinder out of Lily’s cunt easily. The one in her arse takes more work but it’s clear that her muscles are much more relaxed than they were.

Lily is looking at me intently. My guess is she’s willing me to fuck her cunt. My focus is a little lower but the angle is not quite right. I slide my hand, palm up, into Lily’s sopping sex, clamp my thumb on her clit and lift her just a little.

I keeping my hand in her I position my cock against her arsehole and push. God, she is tight. The head of my cock squeezes its way into her like a pot-holer in cave. Her arse ring clamps on my shaft but I keep pushing until I am all the way in.

All I want now is to fuck. Ignoring her protests and please I pull my hand out of her and position myself for maximum leverage by closing my fists around her breasts and letting her take my full weight. Then I let loose all my control and I fuck as hard and as fast and for as long as I can. I’m aware that Lily is making some kind of noise but, for once, I’m not listening. I’m nothing but sweat, and muscle and heat and friction until finally, deep inside her, I find release.

When I come back to myself, all tension, all sense of purpose has left me. Still inside her, I work impatiently to release Lily’s ankle cuffs from the spreader-bar. I throw it aside and let myself collapse onto her.

“You can speak now, Lily,” I say, softly in her ear.

For a moment she says nothing, she just wraps her legs around me. Then, in a voice that oozes contentment she says, “Thank you, Daddy.”


© Mike Kimera 2008 All rights reserved. Do not reproduce without written permission from


A story without a reader is incomplete. Please let me know what you think of this story by leaving a comment below.

2 thoughts on “Toying with Lily

  1. this is my favorite so far, i really like this, there was closure at the end and that was nice and it was perfect for me because i have recently learned to like anal. i found it particularly arousing, i dont like the word arse because its something my grandpa called asses, seems like an outdated or sensored word, but that could be just me. thanks for the story im truly greatful

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