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The Dilemma

"Michael has a problem. Does he let Dora stay with her lesbian friend Terri, and risk losing her?"

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Author's Notes

"Dora goes to London but leaves Michael with a dilemma. She wants to visit her lesbian friend, Terri, in Brighton. Michael thinks he will lose Dora’s affections if he relents. He visits Penny for her advice – and she decides a session in bed with her will solve the problem. Later, Michael discovers Penny has a kink well beyond the mild spanking she had during their swinging evening."

Dora vanishes into the station, bound for London, and I ease the car back down the approach road, her question still echoing in my mind. All the way back home my thoughts churn – yes or no, yes or no – without resolution. In the kitchen, a mug of coffee cooling between my hands, I remain undecided. 

Hoping a second opinion might help me, I step out of the cottage and wander along the lane, wondering if Nigel or Penny can help untangle my dilemma. I pass down the side path to the back garden and, through the open window, spot Penny at the sink. She lifts a yellow‑gloved hand in greeting, her smile bright. “Morning, Michael. Are you coming in?”

I nod and step through the open door.

“Fancy a cuppa?” she asks. The offer is perfect. Never mind that the tea will sit atop my recent coffee; it’s the opening I need.

I settle at the kitchen table, watching her peel off the Marigolds and bustle about, kettle boiling, mugs waiting. With the steaming brew between us. I clear my throat, stumbling over the words. “Penny, I need your help with a little problem.”

Penny tilts her head, a cascade of thick black hair falling aside to expose the delicate pink earlobe I had kissed only days before, while, across the room, Dora basked in Nigel’s unwavering attention.

'Oh, please,' the voice in my head protests, 'I came for her counsel, not her body.'

“Well, Penny, it’s like this. Dora wants to visit her friend in Brighton. You know, the one she had an affair with last year before she returned to me.”

Her lips purse, then soften. She speaks quietly, “Is that the lesbian one?”

I nod. “Yes.”

She pauses, weighing the thought. “And she wants you to go too?”

“Yes.”

Her reply strikes at the core of my worries. “So you fear being left out while Dora rekindles things with her friend? You’re afraid of losing her?”

The truth hangs between us, and I feel the relief in my voice. “I know we have no commitment; she’s free to choose. I just don’t know what’s right.”

Penny’s smile is gentle, her hands sliding across the table to clasp mine. She leans closer, whispering, “Come with me, Michael.”

She rises, leading me into the hall, up the stairs, and into their bedroom. My nerves prickle – this isn’t supposed to happen. “Penny, please, what about Nigel?”

She giggles, light and untroubled. “Oh, he’s in Birmingham with his mates. They’re going to a match at Villa Park tonight. He won’t be back until midnight.”

Her demeanour changes; seriousness creeps into her voice. “You are here, in my marital bedroom, about to make love with me. That doesn’t diminish my devotion to Nigel. Do you understand, Michael? Dora can have her cake — and eat it.”

The words strike clearly, and realisation dawns; I see she is right. I draw her close, arms tightening around her, and whisper gratitude into her ear. My lips brush the delicate lobe, teeth grazing gently, sealing the moment and acknowledging the intimacy to come.

I catch the faint aroma of her perfume as we ease down and sit on the edge of the bed. She leans against me, her voice vibrating through my chest. "Nigel's in Brum with his mates," she says, "and Dora's in London." The silence stretches until she tilts her face back and meets my eyes. "So we have all day together."

The bed creaks as she shifts, and one hand curls into my shirt front between two buttons. "Mikey, you're not going to pretend this isn't happening?" she murmurs. There's an edge to her voice, like she's daring me to back out.

That this is the first time we have been intimate without our partners weighs on my mind, and her contraction of my name signals something, but I can’t quite place what. A fleeting thought crosses my mind. 'Am I cheating on Dora?'

I can't answer her with words. Instead, my fingers find the hem of her blouse, sliding beneath it to trace the curve of her waist. She laughs softly, as if she hadn't expected me to move first. "So, you know what you want.”

Her wedding ring catches the sunlight when she reaches up to unbutton my shirt, deliberate and slow. "For the record," she murmurs, lips brushing my mouth, "I don't want you being gentle today." 

I feel the mattress dip as she straddles my lap, knees pressing into the duvet on either side of me. Her perfume smells different now; there’s something primal mixed with it.

My hands slide up her back, finding and releasing the clasp of her bra. "Is that how you do it with Dora?" she says. The remark makes me laugh against her throat.

Her fingers work the rest of my buttons open, palms slipping over my chest as she pushes the shirt off my shoulders. "You were thinking about this before you stepped into my home today. Weren't you?" she accuses, but there's triumph in it. I cannot deny it – because it’s true.

The bra slips free, followed by her sharp inhale when my mouth finds the side of her neck. "Mikey…" Her voice fractures as my hand cups her breast, thumb circling deliberately. "That’s nice."

Penny's hips grind down, working across my hard shaft. "Mikey, I want your cock," she mutters, fingers yanking at my belt. The buckle clicks open, and her hand slips beneath the waistband without hesitation.

She moans when I bite down on her neck. "That'll leave a mark," she warns. "Nigel will know," but the way her thighs push against me betrays how little she minds. Her skirt rides up as she rocks forward, the friction drawing a groan from me that makes her smirk. "Oh, do you like that?  Thought you might."

She breaks away just to tug my trousers down past my hips. "Down," she orders, shoving me backward until my shoulders hit the mattress, then she climbs over me, pinning my wrists with a look that dares me to move them.

"You're overdressed."

"So fix it," she challenges, releasing me just long enough to hitch her skirt up higher. I feel the wet cotton of her knicker's crotch pressing against me.

In that moment of freedom, I peel her blouse off completely. Her bra follows, and finally her skirt is discarded somewhere near the pillows. Then I grasp her hips and roll, flipping her onto her back.

"Hmmm, you are so masterful," she laughs. Her thighs clamp around my hips, heels digging into the small of my back.

I hook my thumbs into the waistband of her pale knickers. She lifts her hips obligingly but stops me halfway with a palm pressed against my chest. "Not yet." Her other hand strokes down my front, fingers dragging lightly over my ribs before pressing through the fabric of my boxers with the palm. "I want you to be desperate."

Penny whimpers when I press my mouth to the damp cotton covering her pussy. I shake my head side to side, teeth scraping the sensitive skin beneath. The noises she makes run straight through my cock. Her thighs tremble as I drag the fabric aside with my fingers, probe her slit with my tongue, and flick around to find and work her clit. Her hips jerk up instinctively.

Her exclamation, "Oh, fuck! Michael…" trails off into a series of gasps.

The taste of her is salty, and the way her back arches off the bed tells me she’s close. I slow, watching her squirm, grinning when she pleads, "Don't stop." The words dissolve into a moan when I slide two fingers into her, crooking them just right.

Her thighs clamp around my head, muffling her cries as she comes, fingers clenched in the duvet. She shudders through it, breathless, before pushing me away.

I crawl up her body, lower my mouth onto hers, and she tastes herself. Between our bodies I feel her hand grasping my erection, squeezing and rubbing gently.

Our tongues dance together, her hunger driving both of us on. I roll off to lie alongside, her hand still glued to my cock, as we kiss again, and my saliva flows freely into her mouth. My hand strokes her mound, then slips down to find her wetness. My two fingers push inside and crook again, pressing against her secret place, while my thumb pushes against her little bud.

Penny’s hips start to flex, and her breath comes in ragged gasps, “Oh, God, yes.” Then her whole body vibrates, every muscle in spasm. I watch in awe as her orgasm takes hold, and I draw my hand out from her pussy. The only contact between us is her hand clamped to my shaft. And that feels as if it is squeezing the life out of me.

The seconds tick by, then her eyes open, but I feel she cannot see. Her teeth chatter, but she cannot speak. I watch and wait.

She subsides slowly, her tremors dying away, and the hand grasping my cock relaxes, then falls away. 

She looks at me, her smile trembling as she finds her voice. It comes so softly I can barely catch it, “Mikey, thank you. That was something special. Now, I want you to enjoy something special too.”

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Her hand searches for mine, and when our fingers lock, she whispers, “Pull me up.” I rise from the bed, take her other hand, and draw Penny to her feet. For a moment she sways, then steadies herself with a quiet, “Come.”

We step out onto the landing. She leads me to the other bedroom, opens the door, and pulls me inside. The last time I saw this space, it was nothing but an empty shell. Penny had stood beside me then, her hand tracing slow circles across my back. I remember it vividly – the first time we met, her constant touches as they showed us around their new home.

In the weeks that followed, builders and decorators filled the cottage with noise and dust. Nigel and Penny spent long nights with us, sleeping in our spare room, sharing laughter, warmth, and their bodies. Yet nothing could have prepared me for what I see now.

The room is cloaked in darkness, wood shutters sealing the window. Slate-grey paint covers the walls and ceiling, the floorboards beneath us stained dark red. At the centre, there is a single object: a wooden bench. Its top is padded and wrapped in leather, and on its legs hang metal chains and rings that glint faintly in the light of a single spot on the ceiling.

I stand transfixed, unable to believe my eyes. Penny sees my hesitation and swings around to face me, and a hand grasps my half-stiff cock awaiting its turn for action. Her fingers alternately squeeze and release my flesh, sending shivers of pleasure racing through my body.

She closes on me, her soft breasts press against my chest, her breath wafts against my shoulder, and ever so softly, she explains, “Mikey, you are going to fix me to that, then you will thrash me and fuck me. When you are finished, you will leave me there and go home. Nigel will release me when he comes back.”

“But, Penny, that will be hours away.”

“Yes, but you cannot understand my needs, how the feeling of waiting for him turns me on. He will guess and be aroused, then he will take me roughly. Do what I want, like I said earlier; don’t be gentle.”

She slips from our embrace, guiding me toward the wall beside the door. Only then do I notice the shelves and hooks fixed there, an arsenal waiting in dim light. Penny reaches for something that looks like a fly whisk, lifting it with deliberate care. “Use this, Mikey.”

Her voice hangs as she pauses, fingers drifting to a leather strap. She takes it, then selects more. “And this… and this.”

I look at the objects she has dropped on my palm, then Penny’s voice breaks in, “Those are a hood and a ball gag. Help me put the hood on — zip it at the back for me. Then lead me to the bench and secure me. Lastly, force the gag in, then tighten the strap as hard as you can.”

She shifts and stands back to me, lifts the hood over her head, wriggles it around, then asks, “Zip it up, Mikey.”

I pull her panties down. After she steps out of them, I take her hand and lead her to the bench. I watch her explore the padding, then lie on top with her arms and legs hanging down. One by one I shackle her limbs, then fetch the gag and kneel beside her head. 

“Are you ready for the gag, Penny?”

“Yes, but one more thing. You must watch for my safety signal. If I cross my fingers on both hands, you must stop the punishment. Okay?”

I hadn’t thought about that, mumbling an acknowledgement just before commanding, “Open wide,” and pushing the gag ball inside her mouth.

I tighten the buckle on the gag, locking the strap tight, Penny's muffled whimpers barely audible through the gag.

"Count for me," I say, running the flogger's tails lightly over her thighs, watching goosebumps rise in their wake. She hesitates just a second too long before mumbling out a quiet "One" that sounds like “Mnn”.

I tighten the last buckle on the gag’s strap with a satisfying click, and Penny's muffled whimpers become barely audible.

My second hit lands across both cheeks, the impact drawing a sharp cry from Penny. Her "Two" sounds like “Urgh”, as her hips twitch against the restraints.

I murmur, "Good girl," and her answering moan is muffled but unmistakable.

The flogger flashes down again, this time in quick succession – left cheek, right cheek – and Penny's thighs clamp together reflexively before she relaxes them apart. "Ee, Ur," she groans.

I pause, letting the tension build, admiring her sweaty skin gleaming under the dim light. "Let's try that again," I say, dragging the flogger's tails up the backs of her legs.

A choked giggle escapes her, cut short as I land a stroke low across her buttocks, the sting drawing a yelp. "Aith!" she blurts out, hips jerking against the bench. I circle her, trailing fingertips along her spine just to feel her squirm. "Good," I whisper close to her hooded ear. "But we're far from done." Her answering whimper makes no sense, a barely audible blur.

I strike ten hits in quick time, and the flogger becomes a blur – staccato impacts that create crimson stripes across Penny’s cheeks and thighs in quick, merciless succession. Her body convulses against the restraints with each strike, muffled screams dissolving into garbled, wet noises behind the gag. 

By the fifth hit, her legs tremble violently; when the tenth lands with a final, crisp thwack, she collapses onto the leather, breath coming in shallow gasps. Drool soaks the padding beneath her chin, her entire body glistening with sweat.

I pause, looking for her safety signal. It is not there, so I strike ten times more.

The flogger falls again in a painful rhythm, each stroke layering over already throbbing skin. Penny's body jerks like a marionette with every impact, her cries reduced to ragged, animalistic grunts behind the gag. 

Halfway through, her thighs clamp shut involuntarily – muscles locked tight – before the next strike forces them apart. By the final blow, her fingers claw uselessly at the bench’s legs, knuckles white, her entire backside a uniform angry red. Her chest heaves against the restraints, spit pooling in thick strands from the gag's holes, her hooded head lolling side to side as she whimpers weakly.

This time, when I look and I see her signal, she has submitted. I drop the flogger and push my hand between her thighs, feeling my fingers glide effortlessly through her slickness. Penny’s hips arch against my touch, thighs trembling and shuddering with oversensitivity.

My fingers press hard into Penny's swollen clit, rubbing tight circles that make her entire body seize. Her thighs try to close around my wrist instinctively, but there's no strength left in her; they relax again almost immediately. Drool spills freely from the stretched gag, her hooded head thrashing side to side against the leather padding, her breath coming in wet, sobbing gasps. Every pass of my fingers draws another broken noise from her throat, her oversensitive body caught between pushing against my touch and twisting away – but the restraints hold her perfectly in place, leaving her no escape from my ruthless pressure.

Penny's body trembles uncontrollably, her knees locked out. The orgasm rips through her body, bucking uselessly against the restraints as she comes hard, her clit throbbing under my relentless fingers. Drool drips from the gag, her hooded face pressing into the leather as she whimpers through the aftershocks, her entire body tense and twitching.

I shift between her legs and line up my throbbing shaft with her tunnel. Penny's body jerks weakly as I push into her, and I feel her clench around me. Her thighs quiver against my hips, and her restraints clink faintly with every shuddering breath. The gag stifles her moans but doesn't hide the way her hooded head rolls back against the bench, helpless noises in her throat as I start to move.

My hips slam forward, driving Penny's body up the bench as my cock pistons into her dripping cunt – each thrust eliciting a cry from behind her gag. Her restraints rattle with the impact, and her thighs tremble against my hands where they grip her hips. The slap of skin on skin mixes with Penny’s choked whimpers as I chase my release. When I come inside her, I roar with the sharp pleasure of orgasm, and she goes utterly still save for the involuntary clench of her muscles around my cock.

Breathing heavily, I walk around and stand by her head, stroking the hood. "I'm going home now; Nigel will release you later.”

Penny's head tilts weakly toward the sound of my voice, her breath still uneven, and a faint, muffled noise escapes the gag, something between acknowledgement and thanks. Her shoulders twitch against the restraints as my fingers trace the stitching of the hood, then along her spine, her damp skin warm under my touch.

I lean down, kiss the leather-covered side of her head, and whisper, “Bye, and thank you.”

At the door, I turn and take one last look at her body, then turn off the light and close the door behind me.

Published 
Written by SandG_Play
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