Slave To The Wager: Chapter 4 - Sunday Lunchtime

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#11 of Kink

Master has always wanted a sissy and now he has a slave for a day, it's the perfect chance. But will she reach her true calling and achieve sissygasm while satisfying her owner at the same time?

This story is 18+ as it contains themes of sex, bondage, and BDSM.

The chapters can be read independently, but you can read the others here:

Chapter one: https://www.sofurry.com/view/2057550

Chapter two: https://www.sofurry.com/view/2070415

Chapter three: https://www.sofurry.com/view/2080235


Noon, Sunday

"Down!" Master says and I assume the position, kneeling on the floor with my paws on my lap.

"Good boy," he continues, clipping the lead onto my collar. I feel a sharp tug and I'm suddenly onto all fours, obediently trailing behind him. He leads me towards the dungeon, my knees unaccustomed to the harder surface of the floor. I wince as I move, but Master pays me no heed, he is far too focused on the closet in the corner.

"Now," he says as he opens the door. "You're going to be a little sissy this afternoon." He rummages amongst the clothing before fishing out a pair of pink velvet panties. A bra follows, along with knee-length white and pink striped socks and a similarly coloured skirt.

"Put them on," he says as he lets go of my leash. I jump as it clatters on the floor. "I haven't got all day."

I clamber to my feet, swiftly taking the accoutrements and climbing into them. My sheath stirs as I look down at the panties. There is a hole at the back through which I slide my tail, while the top of my crotch is marked by a pretty pink ribbon.

I put on the socks next, pulling them just below my knees. I then lift up my arms and Master fastens up my bra. I then slip on my skirt. He takes a step back and looks me up and down.

"Such a gorgeous little girl," he says, a slight leer creeping onto his lips. "What are we going to do with such a pretty little princess?"

I gulp as I feel the tip of my cock rubbing against my panties. This only stimulates me more, a noticeable bulge forming. Master looks down and laughs.

"Slut," he says as he baps his paw against my package. I whimper but manage to stand up straight. I know what the punishment would be if I ever back away.

Master takes my lead once again and I drop to the floor. He pulls me over to the cage, which he moves away from the wall to meet me.

"Get in," he says, tilting his head towards the open door. I oblige, darting over the metal frame and onto the padded mat.

"Turn around and move forward." I acquiesce. Master grabs my head and moves it into position, before shutting the doors around my neck. I hear the sliding of bolts and the clicking of locks before I realise that I am locked in position. I try to look up, but the cage is gripping me tight, meaning I can only see my Master's ever-increasing bulge.

He laughs before I hear the sound of four locks clipping my cuffs to the cage. I move my arms and legs in response and find them fixed to the bars, a movement that's coupled with the unmistakable first rush of endorphins knowing that I'm now at his mercy.

"Now then little sissy," he says as I hear something being dragged in the distance. "Are you going to be a good little girl and come for me?"

My mind races, unsure as to what he means. My cock starts to protrude from my sheath, kissing the soft velvet of my panties tenderly. I feel a small wet patch forming.

"Looks like you've already started," he chuckles as I hear more dragging behind me. I then hear the flicking open of a bottle of lube before my tailhole is liberally slickened.

I tilt my head in bemusement, but I realise what's coming when I feel the cold press of a dildo on my pucker. I breathe heavily as Master tries to line it up, its tip widening my entrance slightly.

I then hear the sound of a plug going into a socket, before a switch is flicked and my home becomes wider still. I gasp as the toy starts thrusting inside me, rhythmically gliding from the tip to the base. My cock twitches at the same pace as it starts pounding my prostate, a feeling of fullness starting to overtake me.

"Does that feel good, little slut?" Master says. "I bet you're loving it." I whimper my approval as Master turns up the speed, the toy increasing its pace as it delves deeper inside me. I feel a slight dribble of pre in my panties as my eyes roll back in delight, my cock twitching in time to the motion inside me.

I start to breathe heavily as I lose myself in the rhythm, the ecstasy building inside my excited mind. I hear the pumping of the machine increase in intensity as the toy repeatedly punches my pleasure button. The sensations start building deep in my loins, a warming feeling that grows from the base of my tail.

The toy keeps pounding, rigorous and remorseless, as the tidal wave increases inside me. My eyes roll back further and my tongue starts to loll as the pressure builds at the base of my cock. I feel my erection straining my panties, as more dribbles of pre soak into the fabric.

Master turns up the power and the dildo oscillates some more, poking my prostate and forcing the tension to build. A guttural growl works its way from the back of my throat as the yearning builds into a crashing crescendo.

I'm breathing heavily, my mind fully in the moment as my button is pressed again and again. I hear my Master as a mirage, an echo in the ether, whispering sweet nothings into my ear. "Come for me," he says as soft as an angel, yet he is the devil with wicked desire. "Come for me."

I gulp as the pressure becomes unbearable, the cock barrelling down my tailhole, forcing my muscles to tense. My tongue lolls out some more as I pant in desire, the storm reaching its apex in a thundering tsunami. Then the dam breaks and I howl in delight as pleasure rushes over me as quickly as the liquid squirting out of my cock. My panties fill up and the fluid starts to drip down my legs, but I don't care as I'm shuddering in exquisite ecstasy.

Second feel like minutes as I wide the wave of my orgasm, the toy still churning away at my hole. "Good slut," I hear, my Master bringing me back down to earth, as I try to look up and fail once again.

I notice his bulge and I lick my lips expectantly, hoping for a taste. As if he's reading my mind, he casually unzips his pants, revealing his cock proudly standing to attention.

"Do you want this, girl?" he says, wavering it in front of my muzzle. I catch the sweet smell of arousal, combined with his musk, my cock swelling harder at this exquisite elixir.

"Y...Y...Yes, Master," I cry, the toy still delving deep into my donut, addling my brain with my building desire.

"Good girl," he says, grabbing my muzzle and twisting it slightly.

"Sniff it," he demands, moving his cock down the tip of my snout. I trace the veins with my nose, inhaling his scent. I smile, a smile that becomes a wince as the dildo keeps burrowing away.

I look up expectantly, waiting for his next command, but time seems to pass incredibly slowly. "You do know you can have multiple sissygasms in a session. I wonder how many you'll have today."

He chuckles as my heart slightly sinks. I'm already exhausted after the first, I don't know how many more I can take. Before I get chance to think any more, he breaks the silence.

"Lick it," he says and I wrap my tongue around its tip, tasting the umami and already yearning for more.

I smile as his paws clamp either side of my muzzle and he forces his rod deep into my mouth. I gulp, then gip, as the toy keeps poking my button, the overwhelming tide of desire starting to build once again.

I concentrate on Master's cock as it slides slickly over my tongue, almost in rhythm with the toy pounding my tail. The taste is divine as dribbles of pre fleck the back of my throat, the saltiness almost as consuming as his increasing arousal.

"Watch those teeth, girl," he demands as his paws grasp ever tighter. I hear him starting to pant as he jerks his cock harder into my mouth. I gag, a steam of drool seeping out of one corner as he pushes my muzzle deep into his crotch.

I inhale, the unmistakable musk of a horny wolf adding to my own sense of excitement as the cocks in my mouth and my tail move as one inside me.

I wince as the toy keeps knocking at the door, starting a fire deep in my loins. I feel it catching, spreading across my pelvis and towards the base of my penis, a sensation of burning and pent-up desire.

"What's that girl?" Master says as I groan into his crotch, but I try to stay focused on my duty as a pet. I gurgle, the stream becoming a river as the drool dribbles to the floor as pendulous streams hang casually off the inside of my lip.

Master ignores it as he keeps hammering my throat, his breathing becoming increasingly raspy as he tips closer to the edge. My nose becomes moist with the build-up of sweat on his groin, giving an olfactory tang that only increases my horniness.

The fire becomes a conflagration in my crotch as I'm milked from the inside, the tension white-hot, causing me to melt. My eyes roll back as my desperation increases as a spark like a firework ignites my whole body.

Ropes of seed shoot out of my cock, cascading into my panties then seeping onto the floor of my cage. I shudder in exaltation but don't miss a beat with my muzzle, wrapping my maw tighter around my Master's twitching cock.

His breathing becomes erratic as he gets closer and closer, while the toy in my tail is as remorseless as ever. I feel more dribbles of seed coming out of my cock as I feel my Master's cock twitch at the base of my tongue.

"Ready, girl?" he rasps but I have no time to reply as he shoots his load all over my tongue. I feel its comforting warmth on the base of my tongue, allied with the comfort it has given my Master. His groans subside as quickly as his spunk slides down my throat, but he leaves his cock on my tongue for a few seconds longer.

It feels comforting, right, in the heat of the moment as the tension in my tail starts to subside.

"Good girl," he says as he takes a step back, shaking the final few drops of seed onto the tip of my tongue. I smile as I lap up his nectar, delighted to serve, but my happiness is soon punctuated by the pain in my tail.

My heart sinks slightly when I see him put his cock away, but I know I am lucky to have had such a tasty treat. He strokes the top of my head before looking around behind me, noticing the viscous white pool which had formed beneath my prone form.

He laughs.

"Looks like I wasn't the only lucky one," he says as I feel the fireworks set to begin once again. I moan, hoping he can read the hidden meaning, but Master strides over to the controls and only increases the rhythm.

I cry, unsure how much more of this I can take, but I also want to do my Master proud. I know I have a safe word but I am always reticent to use it, only calling upon it in genuine emergencies. I have always liked the challenges set by my Master and feel I'd let him down if I bailed early on this one.

Tears form in the corner of my eyes as the burrowing becomes intense once again. I feel my cock twitching as it prepares for yet another milking, while my exhausted prostate is moaning, desperate for sleep.

I close my eyes as I go through the cycles once more, like a wave machine in a leisure centre that's starting to power up. The sound of the machine is as hypnotic as its motion and soon I succumb to its deviance once more.

Stars flitter across my eyelids as I feel another wave build before it crashes against the walls of my pelvis. Thirty seconds later and it's coming once again, this time more powerful, but the damn doesn't break.

I open my eyes, circles floating across my vision as I spy my Master sat on a bench staring directly at me. I suddenly feel self-conscious so I retreat into my mind, trying to enjoy the building of tension deep in my tail.

Another minute, another wave, this one a tsunami as the desperation becomes ever more intense. I groan, feeling the edge getting closer and closer, but when I think I'm about to spurt, the troops are called off.

I breathe a sigh of relief, but the respite is temporary, as there's another charge by the troops and the general is in charge. I moan ever louder, envisaging the smirk on the face of my Master, as the fireworks begin in the seat of my pants.

A few drips squirt into my pouch, still saturated from before, and they soak swiftly through the velvet and dribble onto the floor. I feel the rocket being launched, thrashing mercilessly into the darkness, before an explosion of seed fires straight from my dick. Colours flash across the sky as I moan in delight, the remnants scattered in the firmament of our myriad dreams.

I pant, the post-climax comedown tarnished slightly by its relentlessness, but a few seconds later, the machine is turned off. The silence shocks me for the first few seconds, it hanging heavy in the air, as my mind stands on the knife-edge of arousal and relief.

I do nothing, unsure what to do, my mind fogged by a sheer sense of exhaustion.

Seconds could be hours as I hang there in stasis, chained to a cage, perhaps for eternity. I jump as I feel Master's paw ruffling behind my ears, before he starts to unlock my paws from my binds. I stay motionless, partly through order and partly through desire, not knowing yet what I needed to do.

I sigh in relief as the toy is removed from my ass, my donut throbbing in time to its previous thrusts. My knees start to wobble as I am finally freed, but I know my neck is still in the door of the cage so I dare not make a move.

I hear a clanging in my right ear as Master puts a key in the lock, opening the first before moving onto the second. He opens the doors slowly and my head becomes free, allowing me to look at his face for the first time that afternoon.

"Good girl," he says but I feel my knees starting to wobble, a sensation that soon takes over the rest of my body. Instinctively I fall, collapsing into my seed as the events of the last hour finally catch up with me.

"You did good," he continues, stroking the top of my head, before wrapping his arms around me in the best hug he can give. I smile, despite my muzzle having sunk into my drool, knowing that I had been a good slut.

"Are you okay?" he continues and I muffle the word "Yes," unable to extricate my muzzle from beneath my hand paws. I hear him sit down at the entrance of the cage, before feeling his paw behind my ears once again.

"It's okay," he says softly as he continues to stroke. "You're back and you're safe. Everything's fine." I struggle to look up at his face, but I try nonetheless, my heart swelling with happiness when I am greeted by a smile. I smile back before sinking my muzzle down once again, needing a few minutes to recompose my thoughts.

"Take as long as you need," he says as his paw moves to the top of my back. "I'll go and get you some water and then I'll come back."

My smile becomes a grin as my brain tries to process events, knowing it'll take time to come to terms with the ordeal. I look up, seeing his feet paws moving away as he heads to the kitchen to get me my drink. My heart swells further in love. I'm lucky to have him.