The Devil’s Bargain
A Halloween Fictional Story by Beelzebabydick.
Darren adjusted his costume—a half-hearted devil getup consisting of red dress pants, a crimson button-up, and a pair of plastic horns perched on his head. He’d considered going all out, maybe with the full pitchfork-and-tail ensemble, but his enthusiasm had waned as the party drew closer. Truth was, Darren hadn’t wanted to come at all. His roommate had practically dragged him out the door.
“Bro, you’ve been moping for weeks,” Marcus had said. “It’s Halloween. Live a little.”
So here he was, nursing a warm beer and watching other people have the time of their lives while he lurked near the snack table, pretending to be interested in a bowl of candy corn.
That’s when he saw her.
She was across the room, laughing at something a mummy said, her head thrown back in genuine amusement. Her costume was simple but devastating—a classic witch. Black corset cinching her waist, flowing black skirt that ended mid-thigh, fishnet stockings, and pointed black boots that added four inches to her already impressive height. A wide-brimmed hat sat at a jaunty angle on her dark curls. Red lipstick. Hazel eyes that caught the light.
She was the most beautiful woman Darren had ever seen.
And she was looking at him.
No, that couldn’t be right. He glanced over his shoulder, expecting to find someone behind him. But when he turned back, she was still watching, a small smirk playing at the corners of her painted lips. She raised her drink in a mock toast—something amber in a rocks glass—and took a slow sip.
Darren’s face went hot. He managed a weak nod, then immediately looked away, his heart hammering. Smooth, he thought. Real smooth.
For the next hour, he tried to blend into the wallpaper, but his eyes kept finding her. And every time, she seemed to sense it, glancing up from her conversations to catch him staring. The smirk never left her face. It was like she knew something he didn’t.
Around midnight, he stepped out onto the back porch for some air. Most of the party had migrated to the basement, where someone had set up a makeshift dance floor. The porch was quiet, lit only by a few flickering jack-o’-lanterns that had started to sag, their carved grins collapsing into eerie sneers.
“Running away already?”
The voice came from behind him. He spun around.
She stood in the doorway, silhouetted by the orange glow from inside. Her hat was gone now, her hair loose around her shoulders. The corset pushed her breasts up and together, creating a shadowed valley that Darren’s eyes accidentally dropped to before snapping back up.
“I—no,” he stammered. “Just getting air.”
She stepped out onto the porch, the heels of her boots clicking against the wooden planks. “I’ve been watching you,” she said, not bothering with pretense.
He swallowed. “I noticed.”
“Good.” She stopped a few feet away, close enough that he could smell her perfume—something dark and spicy, like amber and smoke. “You’re cute. Shy. I like that.”
Darren’s brain short-circuited. “I’m… thanks?”
A laugh escaped her, low and rich. “Relax, devil boy. I’m not going to bite.” A pause. “Unless you want me to.”
The world tilted. Was this actually happening? Women like her—women who looked like that—didn’t talk to guys like Darren. And they definitely didn’t flirt with them at Halloween parties.
“What’s your name?” she asked.
“Darren.”
“Darren.” She tested it slowly, drawing out the syllables. “I’m Whitney. But tonight, you can call me whatever you want.”
He swallowed again. “Whitney. That’s… nice.”
“Nice,” she repeated, tilting her head. “You’re a man of few words, aren’t you? I bet you’re better with actions.”
The innuendo hung in the air between them, thick as fog. Darren’s dick twitched in his pants, a reminder of the inadequacy that had haunted him his entire adult life. Three inches. Three miserable inches on his best day. He’d been laughed at, rejected, humiliated. And this woman was standing here, looking at him like she wanted to devour him.
It was going to end badly. It always did.
“Look,” he said, “you seem great, but I should probably—”
“I have a confession,” she interrupted, stepping closer. She was tall, almost his height in those boots. Her eyes searched his face, and for a moment, the playful confidence slipped away, revealing something else beneath. Something… hungry. “I came to this party with a specific goal in mind.”
“Yeah? What’s that?”
She smiled, slow and wicked. “To find a man with a small cock.”
The words hit him like a physical blow. He froze, sure he’d misheard. “What?”
“You heard me.” She reached out and traced a finger down the front of his shirt, stopping at the waistband of his pants. “I have a very particular taste, Darren. And you—” Her finger dipped lower, just barely grazing the bulge in his pants. “—look like you fit the bill.”
Darren’s mind reeled. Was this a prank? A trap? He looked around the porch, half-expecting someone to jump out with a camera. But they were alone, just the two of them and the dying jack-o’-lanterns.
“Why?” he managed.
“Does it matter?” Her hand pressed more firmly against his crotch, and he gasped despite himself. “I like what I like. And what I like is watching a man squirm while I tell him exactly how pathetic his little cock is.” Her eyes gleamed. “But consensually, of course. If you’re not into it, I’ll walk away right now.”
Later, he would think about this moment. About the choice he made. But right then, with her hand on his groin and her breath warm against his cheek, he couldn’t imagine saying no.
“I’m into it,” he whispered.
Her smile sharpened. “Good boy.”
—
The spare bedroom was on the third floor, tucked away from the noise of the party below. Whitney led him there by the hand, her grip firm and sure, not once looking back to see if he was following. She didn’t need to. He would have followed her anywhere.
The room was small, furnished with a twin bed and a dresser, the walls covered in band posters from a decade-long past. A single lamp glowed on the nightstand, casting soft shadows across the room. Whitney closed the door behind them and turned the lock.
“Sit,” she ordered, pointing at the edge of the bed.
Darren sat.
She regarded him for a long moment, then began to undress—not herself, but him. Her fingers worked the buttons of his shirt with practiced ease, pushing the fabric off his shoulders and letting it fall to the floor. She ran her hands over his chest, her nails scraping lightly against his skin, leaving faint red lines that made his breath catch.
“No hair,” she observed. “I like that. Smooth.”
“Genetics,” he said lamely.
She laughed. “Shut up.” Her hands moved to his belt. “Stand up.”
He obeyed, and she unbuckled his belt, unbuttoned his pants, and pulled them down along with his boxers in one swift motion. The cool air hit his skin, and he felt his cock—already half-hard—begin to stiffen further under her gaze.
Whitney looked at it. Just looked, her expression unreadable.
“Three inches,” she said quietly. “Maybe.” She looked up at him, her eyes dark with something that made his stomach flip. “I’ve seen bigger on a toddler.”
The words should have crushed him. Instead, his cock twitched, a bead of pre-cum forming at the tip.
“Oh,” she breathed, “you like that, don’t you?” She wrapped her fingers around his length—her hand easily engulfing the entire thing—and gave it a slow, deliberate stroke. “You like being told how small you are. What a little nub you’re working with.”
“Yes,” he gasped. “Fuck, yes.”
She stroked him again, her thumb sliding over the head, smearing the pre-cum around. “Say it,” she demanded. “Tell me what you have.”
“I have a tiny cock,” he said, the words tumbling out before he could stop them. “It’s small and pathetic and—”
“And what?”
“And it’s never satisfied, anyone.”
Whitney’s lips curled into a smile. “That’s the most honest thing you’ve said all night.” She released him, and he whimpered at the loss of contact. “Lie on the bed. On your back.”
He did as he was told, settling onto the creaky mattress, his erection pointing uselessly toward his stomach. Whitney stood at the foot of the bed, watching him with an expression that bordered on contempt.
“Look at you,” she said, shaking her head. “A grown man with a dick the size of a lighter. It’s almost sad.”
“Almost?” he asked, his voice barely audible.
She laughed. “Don’t fish for compliments, darling. You don’t deserve them.” She reached behind her back and began unlacing the corset. “Now, here’s what’s going to happen. I’m going to undress. And you’re going to watch. But you’re not allowed to touch yourself, and you’re definitely not allowed to touch me. Understand?”
“Yes,” he breathed.
“Good.”
The corset loosened with each pull of the laces, and Darren watched in a haze of arousal as the garment finally fell away, revealing her breasts—full and perfect, each tipped with a dark pink nipple that hardened in the cool air. She let the corset drop to the floor, then pushed her skirt down over her hips, leaving her in nothing but the fishnet stockings and a tiny black thong that barely contained her.
“Enjoying the view?” she asked, turning slowly to show him every angle.
“So much,” he managed.
“Too bad that little thing between your legs couldn’t do anything with it.” She stepped out of the thong and climbed onto the bed, straddling his chest. Her knees pressed into his sides, pinning him in place. The heat of her body washed over him, and he could smell her arousal, musky and sweet.
She looked down at him, her hair falling around her face like a curtain. Then she reached between her legs and began touching herself—slow, circular motions that made her eyes flutter closed for a moment.
“This,” she said, her voice thick, “is a real orgasm. Not the fake ones you’ve probably gotten from every woman who took pity on you.” She moaned softly, her fingers moving faster. “God, I’m so wet. Can you see it? Can you see how wet I am?”
He could. The evidence was glistening on her fingers, on her inner thighs. His own cock ached, desperately hard now, leaking steadily onto his stomach.
“You’re leaking,” she observed, glancing down at him. “Like a broken faucet. Is that all you’re good for? Making a mess?”
“Yes,” he said. “I’m sorry.”
“Sorry,” she mocked. “You should be. You should be on your knees, apologizing to every woman who ever had the misfortune of—” Her breath hitched, her hand moving even faster. “Of seeing this pathetic excuse for a cock. Of feeling it inside them. Did they even feel it, Darren? Or did they just lie there, waiting for it to be over?”
The cruelty in her words made him dizzy. He’d never heard anyone speak to him like this—not in real life, anyway. The humiliation was a physical thing, a hot flush spreading across his chest and face. And yet, his cock had never been harder.
“Tell me,” she demanded, grinding against her own hand now. “Tell me about your worst moment. The time you felt most inadequate.”
He didn’t hesitate. “My ex-girlfriend,” he said, the memory rising unbidden. “She laughed when she saw it. First time we were together. She actually laughed.”
Whitney moaned, her hips bucking. “God, that’s hot. Tell me more.”
“She said—she said it looked like a mushroom. A tiny mushroom.” The words felt like acid on his tongue, but he couldn’t stop. “She asked if it got bigger when it was hard. It was hard. It was as hard as it could get.”
“Oh, baby,” Whitney breathed, her eyes rolling back slightly. “That’s so wonderfully tragic. She laughed at you. Laughed.”
“Then she told her friends. All of them. I couldn’t show my face at the bars she went to for months.”
Whitney’s movements became frantic, her breath coming in short gasps. “You’re so small,” she said. “So worthless. Just a pathetic little man with a pathetic little—” Her body tensed, her back arching. “—cock.”
She came with a cry, her thighs clamping around his chest, her fingers working furiously between her legs. Her body shook with the force of it, and Darren watched, transfixed, as she rode out her orgasm above him. When it finally subsided, she collapsed forward, her hands braced on either side of his head, her face hovering inches from his.
“That,” she said breathlessly, “was the best orgasm I’ve had in months. And you didn’t do a single thing to help.” She smiled down at him, her lips red and swollen. “That’s how useless you are.”
“Please,” he whispered. “Please, I need—”
“Need what?” She sat up, swung her leg over him, and settled beside him on the bed. “You need to come? With that thing?” She laughed again, the sound sharp and cruel. “I suppose I could help. But you have to earn it.”
“How?”
She considered this, tapping a finger against her chin. “Beg.”
“Please,” he said immediately. “Please, Whitney. I’m begging you. Please touch me.”
“That’s not begging.” She lay back on the bed, propping herself up on her elbows. “Get off the bed. On your knees.”
He scrambled to obey, dropping to the floor beside the bed. The carpet was rough against his knees, but he didn’t care. Nothing mattered except the promise of release, even if it was tainted with humiliation.
Whitney turned to face him, letting her legs fall open. The sight of her—spread before him, glistening and pink—made his mouth water.
“Now beg,” she said.
“Please.” He leaned forward, his hands clasped in front of him. “Please, Whitney, I’ll do anything. I need to come so badly. Please touch my little cock. Please let me come. I know I don’t deserve it, but please—”
“Tell me what you are.”
“I’m pathetic,” he said, words spilling out in a rush. “I’m worthless. I have a tiny, useless cock that can’t satisfy anyone. I’m a joke. A disappointment. Please—”
“Good enough.” She leaned over the edge of the bed and took his cock between two fingers, holding it as if it were something dirty. “Look at this,” she marveled, her thumb and forefinger working him with mechanical efficiency. “Look at how I can barely even grip it. It’s like trying to jerk off a baby.”
The degrading words, combined with her touch—finally, finally—were too much. His balls tightened, and before he could warn her, he was coming, spilling into her hand with a strangled cry. It wasn’t much—a few thin spurts that landed on her fingers and dripped onto the carpet.
Whitney examined the mess with mild distaste. “That’s all?” she asked. “That’s what you’ve been holding onto all night?” She wiped her hand on his discarded shirt, then sat up and reached for her clothes. “I’ve had runnier nosebleeds.”
Darren knelt there, spent and shaking, as she dressed in silence. The haze of arousal was already beginning to fade, replaced by a hollow ache that had nothing to do with his physical release.
“You can stay here if you want,” she said, adjusting her hat in the mirror. “Rest up. Recover.” She turned to look at him, and for a moment, something like sympathy flickered in her eyes. “I’ll be downstairs if you want to talk later. Or not. Up to you.”
She unlocked the door and slipped out, leaving him alone in the dim room. The muffled sounds of the party floated up through the floorboards—laughter, music, the clink of glasses. Someone was having the time of their life down there.
Darren waited until his legs stopped shaking, then gathered his clothes and got dressed. His shirt lay in a crumpled heap, stained with his own release. He left it there.
When he finally made his way downstairs, the party was beginning to wind down. A few stragglers lingered in the living room, but most had dispersed into the night. He found Whitney on the front porch, sitting on the steps with a cigarette between her fingers, smoke curling lazily toward the moon.
She looked up as he approached. “How are you feeling?”
“Honestly?” He sat down beside her. “I don’t know.”
“That’s normal.” She took a long drag, then offered him the cigarette. He shook his head. “For what it’s worth, you took that better than most.”
“I’ve had practice.”
She laughed, soft and genuine. “I bet you have.” She studied his face for a moment, then tucked a strand of hair behind her ear. “I didn’t mean to push too hard. Sometimes I get… carried away. If any of that was too much—”
“No,” he interrupted. “It wasn’t too much. It was—” He paused, searching for the right word. “—cathartic, maybe. In a weird way.”
“Good.” She stubbed out the cigarette on the stone step. “That’s good.”
They sat in companionable silence, watching a group of costumed kids stumble down the street, singing off-key. The moon was full and bright, casting long shadows across the lawn.
“Can I ask you something?” Darren said.
“You can.”
“Why do you like it? The whole… small dick thing?”
Whitney considered the question for a long moment. “Power, I suppose,” she said finally. “I like being in control. And there’s something honest about a man who knows he’s inadequate. No pretense. No ego. Just acceptance.” She shrugged. “It turns me on.”
Darren nodded slowly. “I think I get that.”
“Do you feel better?” she asked. “Worse? Somewhere in between?”
“Somewhere in between,” he admitted. “But I’m glad it happened.”
She smiled, and for the first time that night, it wasn’t wicked or mocking. It was just a smile. “Me too.”
A taxi pulled up to the curb, its headlights cutting through the darkness. Whitney rose to her feet and dusted off her skirt. “That’s my ride.”
Darren stood too, suddenly awkward. “Will I see you again?”
She tilted her head, considering. “Would you want to?”
“Yes.”
The word came out before he could think about it—before he could second-guess whether wanting something like this made him broken or fucked up or any of the other things his ex had called him. Maybe it did. Maybe he didn’t care.
Whitney’s smile widened. “Give me your phone.”
He handed it over, and she typed in her number with quick, sure fingers. When she returned it, her touch lingered against his palm, warm in the cold October air.
“Call me,” she said. “Maybe we can do this again sometime. If you’re brave enough.”
She climbed into the taxi without waiting for a response, and the car pulled away, its taillights receding into the night. Darren stood on the porch, phone in hand, watching until it disappeared around the corner.
The jack-o’-lanterns had gone out.
But for the first time in a long time, he didn’t mind the dark.
The End.
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