Jack's Head

by Siggy Shade

My pulse quickens, and an excited shiver runs down my spine to settle between my legs. William proposed last night with a five-carat diamond solitaire. I accepted, of course. “Is it lingerie?” “Something to put in your mouth,” he whispers in my ear. I grin. “A chocolate eclair?” He snickers. “Saltier but a similar shape.”

I lick my lips at the prospect of William’s cock. He probably wants to play out the erotic story we read about the highwayman and the tavern wench.

William kneads my tense shoulder muscles. “Now that you’re joining the family, it’s time to show off your legendary fellatio skills.” Samuel beckons with a gloved hand. “Make it good, and we’ll approve William’s choice of fiancée.”

And he’s stroking a stubby cock that, even when erect, barely extends past his fist. My stomach plummets, and I slap a hand over my mouth. My fiancé wants to pimp me out to his uncles?

“W-what made you think I would agree to this?” The words catch in my throat because I can’t believe he wants to share me with his fucking relatives. “Bess.” He waves his hand toward the older men. “This is just like the novella we read together last month. You said it was hot.” My jaw drops. “But that was fiction!”

Even when our relationship got sexual, part of me waited for a catch. But William claimed to love my fuller figure and my attitude toward sex. We used to read smutty books together and try out the spicy scenes.

Purr

“You’re a great assistant and an even better fuck. But looks-wise, you’re a five at best.”

Hn yo uncle got a micro

“I’d rather suck a corpse than go anywhere near your relatives’ rancid cocks.”

Thats what shes about to do to hehehehehe

“Halloween is too dangerous for you to drive alone,” he says, sounding smug. “Headless Jack haunts the roads, hunting for people to kill. At least stay until morning.” “So you can coerce me into getting on my knees?” I yank the door closed, start the engine, and pull out of the parking spot.

Moments later, the temperature drops, and a flash of silver lights up my periphery. I glance at the rearview mirror to find the road empty, save for a glowing horseman. And he’s galloping toward me, a foot above the tarmac.

In the middle of the road ahead dances a black horse with eyes of fire and a mane of smoke. It stands over eight feet tall and looks like it could trample my Beetle to dust. More worrying is its rider. He wears a similar highwayman’s costume to William’s but the cloak is frayed. In one hand, he carries a double-headed ax, and in the other a jack o'lantern filled with flames. Cold shivers run down my spine. There’s a void above his shoulders. He doesn’t have a head! I shift into reverse, twist toward the rear window, and speed back down the road. The horseman places the jack o'lantern on his shoulders and rides forward. “Fuck.” He’s no longer a silver specter—he’s real. And he’s advancing toward me with that ax.

The car hits an invisible barrier with a hard jolt. I whip my head around to see the horseman jumping off his steed.

I can’t outrun a man, let alone a horseman that can do eighty. And he probably gets off on a woman’s shrieks. Clomp, clomp, clomp. His heavy footsteps shake the car. He’s the tallest man I’ve ever seen and worryingly solid.

“Stand and deliver!” shouts a voice deep enough to penetrate my bones. “Your noggin or your life.” How the hell does he expect to take someone’s head without taking their life? I grit my teeth and snarl, “No. Fucking. Way.”

The horseman holds his ax like he’s about to take a swing. A swing at my head. I pull right to swerve out of the trajectory of his ax, but the steering wheel won’t budge. My pulse quickens. In a few seconds, I’ll become headless—just like him. Instead, I duck, just as his blade slices through glass and metal, cutting through the roof like a tin of corned beef. Cold air blasts over my scalp. An even colder hand grabs me by the neck and lifts me out of my seat. I squeeze my eyes shut and gasp. “I have you now,” he booms.

With a shuddering breath, I wait for the blade to strike, but he hesitates. From the way his flames warm my breasts, it’s not a stretch to imagine why. The horseman pulls me into his chest, filling my nostrils with the scent of sulfur–probably because he’s fresh out of hell. I’ve got to act fast. My life flashes before my eyes. Vague recollections of the parents who died when I was four, followed by a bleak childhood spent in foster homes.

A cool breeze whips around my body, making my nipples tighten. I shove those memories aside. If I don’t think fast, I’m going to wind up worse than dead. Why isn’t William here, being threatened instead of me? He’d probably offer me up to the headless horseman for a blowjob. Wait—that’s not a bad idea.

He doesn’t react until my fingers skim his breeches. The grip on my neck loosens, allowing me to breathe. My pulse beats a rapid drumroll. It’s now or never. I slide my hand down his crotch, my fingers tracing the outline of a cock almost as thick as my wrist. Bloody hell. At his sharp intake of breath, I crack open an eye to lock gazes with a pumpkin as long as my head and twice as broad. Yellow flames flicker from its triangular eyes and from a broad mouth carved with jagged teeth. My gaze wanders to the top, where a thick stalk curls backward, surrounded by withered leaves that simulate hair. Fuck. Self-preservation kicks me in the ass. I should be seducing, not scrutinizing. As I give his cock a gentle squeeze, a groan reverberates through his broad chest. The flames that fill the pumpkin’s eyes and mouth burn brighter, bathing my face with warmth.

The shiver down his huge body says he does. He places me carefully on my feet, the way a gentleman might help a lady out of a carriage. My survival instincts scream at me to keep going. “There’s more where that came from.” I lick my lips and hope to god I sound lusty. “Now, let me see your other head.” His chest reverberates with a deep rumble that borders on a growl. My skin tingles with trepidation, and every hair on my body stands alert. “Show me what else you can do, wench,” he growls, the sound going to the pulse between my legs. “Impress me, and I will spare your life.”

Jack’s deep growl makes my hair stand on end and chases away my insecurities.

“Well then?” he says, his voice unusually husky for a man with no head. “Will you accept my challenge?” My fingers tremble over his thick length. Could I get away with giving him a handjob over his breeches?

The pulse between my legs pounds so hard that I have to squeeze my thighs together to muffle the sound. Fuck. He’s twice the size of my ex and three times as thick. I slide my fingers over the ridge of his cockhead and stifle a moan as heat floods my pussy. This guy has some serious potential. “Take it out,” he rasps. He doesn't need to tell me twice. I fumble around his fly, finding a flap of fabric that runs diagonally over his crotch. After undoing the buckle at the top, I slip my hand inside.

His flesh is warmer than expected, with soft pubic hair that curls around my fingers like vines. His chest rumbles, and I delve further down and wrap my fingers around a thick and hot pulsing length. The horseman groans. So do I. It’s the longest, meatiest cock, adorned with prominent veins and a bulbous head. A bead of precum glistens on its tip, making me gulp. “Well?” he says, his deep voice sharp with impatience. I lick my lips and run my hand along the shaft. “It’s just so…” “Were you expecting a summer squash?” “Of course not,” I blurt. “But I’ve never seen anything so huge.” At the horseman’s rusty chuckle, the rope of tension around my neck eases, and I can finally exhale. “I’ll wager you’ve never tasted anything so hearty. I’m standing. It’s your turn to deliver.”

It’s impossible to know where to look—at the oversized pumpkin or the oversized cock, which fills the entire right side of my periphery.

I gulp, my gaze landing on the blade of his ax. My dilemma should be simple: lose my head to this homicidal specter or suck his monstrous cock. Even that second option is perilous—his erection is alarmingly big. It could cut off my air and send me to an early grave. He clears his throat with a hollow sound that stiffens my spine. My gaze jerks back to his cock. It’s surprisingly alive up close and flushed with prominent veins running down its underside. I try not to imagine how it would feel, splitting me open, but my pussy clenches with need.

ax. I lean forward and place a kiss on his damp cockhead. Apart from being almost twice the size of William's dick, it’s no different from a living penis. I run my tongue up the length of his shaft. He smells mostly of stone, if such a thing is possible, with the taste of human skin. Jack’s breathy groan fills my pussy with a thrill of satisfaction. I reach into his breeches to cup his balls, but he grabs my wrist.

Pushing aside the question of why he wants to keep me away from his testicles, I wrap my fingers around his erection and squeeze. Jack moans as I flick my tongue back and forth over his slit and lavish his shaft with up and down strokes.

I part my lips and engulf Jack’s cock in my mouth. My jaw opens to its full capacity to accommodate his size, and I hum my appreciation. “Wanton wench,” he says, his voice breathy. “You sure like the taste of my cock.” Sucking in my cheeks to create more of a vacuum, I hide a smile. It’s too early to celebrate. I still have to make him cum. As Jack rocks forward on the balls of his feet, I ease him further into my mouth.

but all men become tame with their cocks in another’s mouth. Timing the movements of my head with the up-and-down strokes of my hands on his cock, I build up a rhythm that makes Jack pant. He breathes heavier than a normal man, his chest sounding like bellows. Heat builds low in my belly and the pulse between my legs quickens. Wetness floods my pussy, and my clit throbs for attention. I squeeze my thighs together to create some friction.

“Eyes on me,” he growls. I tilt up my head and meet the triangular holes in his pumpkin, filled with flames.

but kneeling here with his cock in my mouth makes him look otherworldly. It doesn’t help that he’s still holding that fucking ax. “Good girl,” he snarls. My heartbeat quickens, and I hum around my mouthful. I really shouldn’t be getting so excited over a malevolent spirit’s praise. “You like that?” he says without moving the pumpkin’s carved maw. “You like sucking the cock of a vengeful ghost?” I choke around his cock.

“More?” he asks. “A lusty lass like you can take it.” His words send a bolt of arousal straight to my pussy. My hand drifts between my legs, and I rub my clit through my petticoat, apron, and skirt. Chuckling, Jack cups the back of my head with a gloved hand. This time, warmth radiates through the leather. Before I can consider this temperature change, his cockhead hits the back of my throat. My pussy tightens, wishing it was the one taking such a heavy dick. “Here it comes.” He pushes forward, toward my tonsils, somehow circumventing my gag reflex. Every time William used to go deep, I would retch and splutter. It’s different with Jack. My throat relaxes, accommodating his cockhead. Perhaps deep down, my body knew William wasn’t the one.

“Take deep breaths.” He runs his fingers through my hair, the caresses a balm on my frantic heart. My brows rise. Is the headless horseman being considerate? Now’s probably not the time to question his motives. “Alright,” I try to say around his girth, but the words are muffled. I inhale through my nostrils, filling my lungs with air. Once I’ve gotten used to his size, I give him a nod. He pulls back several inches until his tip stretches my lips. I flick my tongue up and down its slit and lap up the salty precum. “You are taking my cock so well,” he rumbles. I preen at his praise. Jack snaps his hips and reenters me with a sharp thrust that sends shocks to the marrow of my bones. He pulls out again as I swallow around him, only to fuck into me once more. I should cough, I should splutter, I should struggle for air, but my pussy is so hot and wet and slick that all I care about is my release. It’s impossible to reach my bare clit, since I’m kneeling on my skirts, so I rub harder through the layers of fabric. Up and down, up and down, I move my fingers in time with Jack’s thrusts. Pleasure circles my core like a cobra, coiling and collecting until I can’t stand the pressure. I need more friction.

My ears fill with Jack’s heavy breaths and deep, shuddering groans. I lash my tongue from side to side, wondering if I'll survive the night. “Good girl.” Flames coil from the pumpkin’s jagged maw, but the words echo from deep within his belly. I keep my eyes upward, just as he ordered, even though my vision blurs. “Such an eager slut.” His fingers tighten around the back of my head. “But I wager you could take even more.” I make a noise in the back of my throat and try to nod through his iron grip. This is no longer about impressing Jack. I want this for myself. Bobbing forward as much as he’ll allow, I encourage him to give it to me harder, faster, thicker. Jack pistons in and out of my mouth, his breath quickening. The flames that fill the pumpkin’s eye-holes burn so bright that my vision fills with yellow. I rub the fabric over my clit, my pussy pulsing with need. As Jack’s moans become deeper, more guttural, more inhuman, every nerve in my body thrums with anticipation. The air stills, and the flames that fill his eye holes recede. My skin tingles, the way it does when waiting for lightning to strike after thunder. The drumbeat between my ears beats loud enough to muffle the sound of his movements. Jack is about to cum, and all I can think about is how I’ll swallow all his spunk. His cock swells and a roar fills my ears that rattles my skull and hits every inch of my skin like static. The cock in my mouth pulses, once, twice, three times, before he pulls out with a sat...

I sit back on my heels and frown. Where’s the cum? Do ghosts have dry orgasms? Part of me wanted a mouthful of jism. Jack tucks himself back into his breeches with one hand. The other holds the ax up to the sky. Moonlight glints on its sharp edge, and I swear it’s already coated with blood. Fucking hell...

With a deep chortle, he offers me his hand. I take that as a good sign and let him help me to my feet. “You are free to go, Milady, but I would like to make you one more offer.” “What?” “Satisfy me until sunrise, and I will show you the location of five hundred gold sovereigns.”

“Your answer?” he snarls. “May I ask a few questions?” He nods. “You asked me to satisfy you.” I gulp. “Will it hurt?”

Jack pauses for a few heartbeats before answering, “Only in the most delicious way.” Heat surges between my legs. I already know from the ache in my throat that fucking his cock would be phenomenal. But what if sex with a specter is deadly? “Will I come out of it alive?” I ask. Jack cups my cheek. It’s a gesture so tender that my breath catches. Warmth radiates through the butter-soft leather glove, making my skin tingle. The affection causes the butterflies in my stomach to flutter their wings. “If you accept this second challenge, you will end the night as a very rich woman.”

Jack shakes his pumpkin head. “If your cunt is as sweet as your mouth, you will be worth every pound of that treasure.” My throat tightens. “But that doesn’t answer—” Jack places a finger over my lips, cutting off my words. “You will come to no harm. On my honor as a gentleman and a thief.”

“What do I need to do?” “Look at me,” he says. My eyes snap open. I hope to every imaginable deity that Jack doesn’t demand a kiss. The flames curling from the pumpkin’s jagged maw look like they could sear my soul to cinders. “For the rest of All Hallows Eve, you will submit to my desires,” he rumbles. “You will give me free rein of your cunt and mouth and rump. Should you wish to end proceedings, you will leave empty-handed.” In other words, he wants to fill my holes.

Before I can ask for more details, he swings his ax across the air, sending shards of glass flying into the trees that border the road. Then he lowers me onto the hood of my car. He looms over me, his monstrous pumpkin the only source of light. “Jack?” I croak. “Lift your skirts,” he says, his voice a rough command. My clit throbs as I gather the lower half of my dress and petticoat over my hips. A cool breeze blows over my exposed thighs, making the skin there tighten into goosebumps. “Push your drawers to one side.” It takes a second to register that he’s referring to my knickers. As I expose my pussy, the lace trim brushes over my clit. My breath catches, and the muscles of my core clench. I need more friction. Jack draws so closely that I tremble at the heat of his flames. “My, my, what a comely little cunt.”

My clit swells at his praise. And my gaze wanders down to the erection straining his silk breeches. The hours would fly past if I could get Jack to pleasure me with that meaty cock. “Thank you,” I murmur. “You should see how prettily you glisten.”

“What do you want, wench?” he snarls. I reach down between our bodies, trying to palm his erection, but he presses down on my hips so it lies flush against my pussy. Jack isn’t going to fall for that trick again. “Answer me,” he hisses. “Y-your cock,” the words come out garbled. “What about it?” “Please fuck me with that huge, thick erection,” I blurt. He loosens his grip on my neck and draws back a few inches. “You will earn that privilege.” My brow furrows. “How?” “You will take Rudger.” Dread pools in my gut, which tightens with a sense of impending terror. I glance over his shoulder at the horse and grimace. No amount of treasure could make me stoop to something so depraved. “Absolutely not.” I place my hands on his shoulders and give him a shove, but he’s immovable. I wait for Jack to explode with rage, the way William might in the face of rejection, but he snickers. The sound is breathy, joyful, yet oddly sinister. He’s taking my refusal rather well. “Rudger is the weapon I stole from His Majesty’s executioner,” he says.

His ax spins in his palm, its blade glinting in the moonlight, before Jack points the hilt toward my pussy. “This is Rudger.” “Oh.” An inanimate object is a hundred times better than a horse, but do I want to be fucked with his murder weapon? Five hundred gold sovereigns say yes. “What say you, wench? Will you take its haft?” “Alright,” I say, assuming that haft is old English for a handle.

“Frightened?” he asks. “A little,” I whisper. With a flick of my wrist, he slices through the fabric of my blouse, exposing my left breast. “Beautiful,” he says, his voice warm. The words send a shiver of pleasure across my skin, but I don’t dare make a move to thank him in case I ruin his concentration.

“Your cunt is aching for my Rudger,” he growls, the flames in his nostrils receding. “I can smell it.” I bite back a moan as he slides the blade up my inner thigh, my muscles clenching in anticipation. Jack grabs my knee with his free hand, pushing it further apart from the other and laying me bare. A cool breeze meanders over my exposed pussy, sending shudders down my spine. This is edgier than anything I ever did with William—no one’s ever wanted to penetrate me with an ax. Ax. Ax as in ax murderer.

“That’s the same ax you use to chop off heads.” This is a statement, not a question because there’s no way a monster like Sixteen String Jack would keep a spare one just for the ladies. The flames that fill the pumpkin’s eye-holes narrow. “What of it?” “You can’t put that thing inside me without cleaning it.”

With a harrumph, he dips the entire handle into his fiery maw, filling the air with the scent of burning firewood. When he extracts the ax, it’s shiny and new. “Better?” he asks, his voice sharp. “Perfect.” My legs flop open. “Now, fuck me with Rudger.”