Just a Friendly Trick & Treat

Just a Friendly Trick & Treat

A Halloween Adventure in the Trans Zone

Millie Dynamite

© Copyright 2023 by Millie Dynamite

NOTE: This work contains material not suitable for anyone under eighteen. This is a story and contains descriptive scenes of a graphic sexual nature. This book is pure fiction. Names, characters, places, and incidents either are the product of the author's imagination or used fictitiously—any resemblance to actual persons, whether living, deceased, actual events, or locales, is entirely coincidental.

All characters are over the age of 18.

Just a Friendly Trick & Treat

Quinn tucked herself in carefully. It takes extra care to hide what you have when you're a girl with a lot extra. Donning her Harley Quinn costume, she admired herself in the mirror. The Daddy's Little Monster, emblazoned across her pert chest, had quite the double entendre.

She might not have as large a chest as Harley, but Harley Q. didn't have a monster banana in her panties.

Armed with her costume and a bag full of treats, Quinn set off for the night's trick-or-treating. Her white pleated skirt barely covered her ass, and the ripped shirt showed off her tight tummy to full effect. She had dressed to impress and intended to get as many sweets as possible.

The white pleated skirt allowed her long, shapely legs to attract the bees to her flower. Of course, she'd need to pick the right bee. But how does she choose one that'll yield to her charms and not freak out?

This was the question.

Her phone lit up, and the text appeared, "Hi, I'm Rich, and your Uber awaits."

"Be right down, Rich," she sent him.

She exited the brownstone, promenading down the stairs, swinging her bat, and swishing her ass. What a shock—the Uber was a shiny, silver Rolls Royce. Beside the back door stood a tall man wearing a black suit and tie.

"Your carriage awaits, Ma'am," the driver said.

"You're Rich?"

"Richard, actually, and unfortunately, I was rich. Now, I'm only a poor Uber driver."

"Rich, would it upset you terribly if I sat up front with you?"

"Not at all, Ma'am," Richard said. Opening the front door, he held his hand out to Quinn.

Switching the bat to her other hand, Quinn lightly held his and slid into the seat.

Closing the door, he moved to the driver's side and entered the car. Starting the motor, he checked traffic and pulled from the parking spot. Trying to be nonchalant, he avoided his eyes darting to her. He wished she'd sat in the back, where he would have been able to admire her build without being obvious.

"You're going to knock the boys over at your soiree," Rich said.

"Oh, you think so?"

"Absolutely."

"Rich, you look about 30 years old to me. What happened to your money? Oh, never mind, that's rude of me."

"No, it isn't. My father died, and all he left me was this automobile. My trust fund, which I had lived off of, well, Dad had more debt than assists, and his debt became mine. So, I have a grand total of three hundred thousand left to my name."

"Well, that isn't chicken feed."

"Yeah, I know, but not enough to live on the interest. I have no skills at all other than driving. I'm an excellent driver. When you're ready to leave your Halloween doodad, just text, and I'll pick you up."

"Surely you have other clients tonight, right?"

"Nope, not a one."

"Why not be my plus one?"

"What?"

"You heard me. You're in costume, dressed as a chauffeur, so why not?"

"Are you sure?" Richard said.

"Well, Rich, you're pretty cute. But, I should warn you, I'm a trans-girl."

Stopping at a light, he turned to her.

"You're absolutely stunning," he said. Lifting his right hand, he made a scissor motion with his fingers, "Snip, snip?"

"No, I still have my boy thing. I'm Quinn, by the way."

"Pleased to meet you." A small, slightly fearful smile crossed his lips. "Sure, I'll be your date."

"Interested?"

"More curious, I guess."

"Drive on, Macduff."

He laughed, turned, and noticed the light gleaming bright yellow, turning to red.

"Next light change," she said.

"Yeah." He turned back to her. "Very curious, Miss Quinn."

"Quinn is my first name."

"Pleased to make your acquaintance, Quinn."

Taking off her seat belt, she slid to the middle beside him and kissed his cheek. Running her hand over his face, she kissed his ear and whispered to him.

"I'm a trans-dominatrix, top. Still curious, baby boy?"

Taking a deep breath, "Yes, exceedingly curious."

Thoughts of his college days and a few wild experiments ran through his mind. However, those were different. Richard's roommate and he had been quite close. Man to man, you know. But this transgender thing was something new to him.

"Do you find pleasure in light pain?"

"Oh, my, yes."

As he drove toward their destination, Quinn snuggled against him, her hands roamed his body. Touching him tenderly for a moment, pinching flesh with a ruthless delight the next. When her hands found his stiffened shaft, she rubbed him with a scintillating tenderness.

Her breasts were firm and pressed warmly into his arm. His manhood stirred, and his balls rose.

"Best if you stop."

"Oh, does my plaything think he might nut?"

"Yes."

Quinn moved away from Rich and put her seatbelt back on.

"I'm gonna punish you for this."

"I know," Richard said.

Richard's eyes darted to her and to the road. She sat there, stoic, perhaps a bit angry. The blood drained from his penis, and he wondered if he'd fucked up. For a moment, he thought he might say something, but what? He didn't know what could make the situation better.

"I'm sorry."

A deep, sensual giggle turned into a chuckle and, eventually, a hardy laugh.

"Oh, my dear, not rich, Rich, you will be."

This had a playful tone, and he felt better. However, he knew Quinn might be more serious than she appeared. He thought back to college and his roommate. His only same-sex friendship with benefits. He'd been pretty dominant. Rich had enjoyed his cruelty.

However, Quinn seemed to be more so in all of it than Blake. He shook Blake from his mind. This was nothing like they had. Rich glanced over at her.

Quinn had her thumbnail between her teeth and ground on it. His impression was that she was thinking of something — nasty — to do to him. She arched her eyebrows a few times.

"Yeah, I'll make you regret pushing me away."

"I really am sorry," he said, returning his attention to his driving.

Once they parked, he went to let her out. As soon as he reached to take her hand, cuffs came from nowhere. One side was on his left wrist. She stepped out, turned him to the car hood, and bent him over. Pulling his right arm back, she cuffed the wrist.

She pulled her bat out of the car, locked the doors, and closed her door. He stood and faced the building. Quinn put the bat on his back and pushed him forward. She told him to move every few steps and smacked the bat into his spine. Nothing brutal or cruel, not yet. He pretended to drag his feet.

"Keep moving, sweetie pie, keep moving." Quinn struck his back a bit higher and vigorously.

Once in the door, Quinn handed her invitation to the doorman.

"Miss Quinn Landry and her companion," the man said.

All eyes turned to them. Quinn Landry roughly pushed Rich forward. The crowd gave a golf clap of approval. One older man said, "Bravo." A young woman dressed as a demoness let out a devilish laugh. Everyone was dressed in costumes. The orchestra played a waltz.

Quinn and Rich danced. Richard, with his hands restrained behind his back. Quinn rested one hand on his shoulder, the other holding the bat, allowing it playfully to strike his hands and ass. They promenaded about the floor.

"May I cut in?" a voice said as a man tapped Rich on the shoulder.

"Rich, be a good boy, stand still, right there, until I come back." Quinn turned to the man. He took her hand and wrapped the other around her waist.

"Can you leave the bat behind?"

"Yes, I can, but I won't," she said, tapping his leg fat end.

Immediately, she took control and danced him into an adjoining hall. Quinn guided the stranger into a dark corner in a few quick movements. She stepped back and put the bat against his chest. Her smile morphed into a hateful glower.

"Who the fuck are you?"

"Jason Stiles, Miss Landry. Please move the bat."

Pulling the bat down to his stomach, she made a quick motion and punched him.

He exhaled and hunched. Out of defiance, he straightened himself. Standing his ground, ready to make his argument.

"Do you know who and what I am?"

"I don't believe it. No one as beautiful as you, so well put together, could be a transgender woman, and certainly, I don't believe, if you are, that you have some monstrously enormous cock. More than likely a shriveled-up Vienna sausage. I'm also unconvinced by your dominance."

"Oh, Mr. Stiles, you are so very wrong. How much cash do you have on you?"

"What?"

"You heard me. How much money is in your wallet and pockets?"

"Well, maybe $1500, why?

"How about a bet? I bet you, $1,000, my cock is bigger than yours?"

"I'll take that bet," he said. Unzipping his pants, he whipped out a not-unimpressive-sized dick, somewhat lacking in girth but nearly seven inches.

"So, Trick or treat, Quinn, show me what you have."

Reaching under her skirt, she freed herself, and her meaty appendage hung free.

Stiles went white, dug out the money, and handed his cash to her.

"Do you want to join me and my slave?"

"Um, no, I don't think so. Is the other thing true? Are you cruel?"

"Come play with slave and me. Find out for yourself."

Quinn walked out of the hall, slipping the money into her candy bag before she returned to her dance partner. Without speaking, she resumed their dance. They moved about the dancefloor, Mistress and slave. Richard was dying to ask what happened. Somehow, he realized that would be a mistake.

The other revelers drifted into the background, for Richard only had eyes and ears for her.

After twenty minutes, seven full dances, they sat down at a small table, and she fed him cheese, lifting a glass of champagne to his lips, now and then, for him to sip. All the while, she taunted him.

"Wish I could hold you," he said.

"Oh, you do, do you?"

"Yes."

"There's this lovely dungeon here. Shall I take you there?"

"Oh, my yes, Mistress."

The couple meandered through the partiers, and Quinn Landry spoke to men and women as she passed them. Everyone seemed to know her, and from the looks they gave Richard, they understood better than he what was about to happen. While Richard envied their knowledge, the unknown didn't frighten him.

A massive door, with a key poised in a lock, stood in one corner of the room. When the couple reached it, Quinn twisted the key. It unlocked with a sharp, scraping click, and she opened the door. She retrieved a small sign from inside and hung it on the door handle.

Do Not Disturb.

They entered a small three-side room, and stairs ran down on the fourth side. The same noise echoed in the darkness when Quinn locked the door. It was as if the door between heaven and hell sealed him in one place or the other. But which was it?

Thick, moist mustiness greeted them. A heady odor, some nasty scents of sex and danger. Harping in the back of his mind was excitement tempered by fear. His flesh crawled with fire ants burning underneath, making a journey from his mind to manhood.

"Should things be too intense or painful, just pink, and I'll redirect things. Now, let's go down. Be careful, sweetie pie. If you fall, you'll hurt yourself. That's not your job. It's mine." Her words were kind, cold, and hateful simultaneously. He moved forward and down, cautiously taking the steps, slowly, one at a time.

Pushing him in the back with the bat. Rich stumbled.

"Not that much care," she said.

"Yes, Mistress."

It took only a few seconds to descend into the dimly lit room, but Rich's expectations made it seem an eternity. Once he found the flat level ground of the dungeon, he gazed about, his mouth agape, with a sense of childlike wonder. There were racks, tables, X-cross, and all kinds of whips, chains, restraints, binders, spreaders, and implements of torture about the floor and walls.

Quinn Landry removed the cuffs and breathed barely audible words into his ear. Her husky voice sent shivers down his spine.

"Strip, cutie pie." She walked by him as he disrobed, running hands over whips, flogs, crops, and canes. After she found what she was looking for, Quinn hiked up her skirt and shimmed out of her panties, allowing them to fall to her ankles. The pleated skirt fell back over her ass.

When she turned back to him, her skirt stood straight out, with a bulbous prickhead just beyond its cover. Quinn's love stick was the largest he'd seen in the real world. Much bigger than his college buddies.

"Gawd," he said in a referential drawl. "Never, in all my born days, seen such a big pecker."

"Go to that X-Cross," she said, pointing with a four-foot cane. "Shackel your feet, cuff your left wrist, and wait there like a good boy."

"Mistress, do I face the wall or look away?"

"The wall." Quinn Landry bent the cane, holding each end. She flexed it several times as her slave followed her direction. "I suggest you find something for your hand to do other than jacking or covering your ass. Those would be bad choices."

Striking each of his ass cheeks softly three times, "I always warm up before I get serious."

She again spanked each cheek a bit harder, three more times. The air was thick with the stench of old sex, pain, and expectancy. Slowly, each blow hit rougher than the last.

Rich sucked in air with each blow. Exhaling between the strikes.

Without warning, the assaults turned rougher. Five in a row turned into ten, fifteen, and twenty. Richard clutched to the hanging unused restraint. Resisting the dual temptations of jerking his prick or trying to shield his butt.

For a moment, a brief one, the word pink, hung inside his mind. He pushed it from his thoughts. He wanted, needed this.

The blows were clean, sharp, and resounded loudly upon his buttocks. When he cried out, his whimpering smothered in a throaty, guttural grunt. Quinn beat the living piss out of him, and he'd asked for more.

"Oh, please, Mistress, more."

Rich understood the pain of the cane would last for days. Sweet lingering memories would taunt, tease, and make him seek her. His will had melted into her desire, and there was no turning back.

Quinn had his attention, and there was more to come.

"Please..."

The blows fell faster. The intense agony intensified. Richard had never felt such a beating, so sharply erotic, driving pleasurable pain into him. He was...desperate...for it to stop. And yet, he wanted this so badly. The pain was harsh and awakening. Sensations and feelings he'd forgotten. He desperately wanted to rub his hard-on, but resisted.

Quinn paused and moved to him. She grabbed his crotch. Squeed until a drop of precum leaked from his piss slit. Bending down, she licked the drop from the tip. Rising to him, she kissed him, thrusting her tongue into his mouth.

"I'm working hard to make you happy, right?"

"Yes, mistress."

"More, or are you at the end of your rope?"

"More."

She ran her hands, fingernails catching his flesh, down his back. Hugging her body against his, she ran her nails across his chest and abs. Quinn pinched his nipples. Biting Rich's neck and pressing him into the rough wood of the X-Cross.

"Gawd, that hurts so good, Mistress."

Quinn pressed Richard's chest into the wood of the cross. She moved away, retrieving her cane. Once more, she pounded his ass, back, and upper legs again. As she whipped him, his dong banged into the cinderblock wall.

Involuntarily, he humped the wall under her assault.

Quinn Landry used her free hand to pinch his balls. She twisted and pulled until he yelped.

Her attack stopped. She took Rich's peter and turned it toward the floor.

"Cum, bitch. Shoot your load on the floor."

Thick ropes of semen shot from his dick. His cum covered the floor and dripped from his rod. Jacking him, squeezing his balls mercilessly, milking him dry. Quinn released his balls and cock and walked away.

"Release yourself and lay prostrate and eat your cum like a good boy."

Quickly, he followed her orders. As he lapped up his discharge, "Fuck, Mistress, this is the best day of my life."

Quinn chuckled quietly. "Not yet, sweetie pie. Have you cleaned it all up?"

"Yes, Mistress. That was incredible, Mistress."

"It's not over yet, loverkins."

She moved to him, kicking his ass again and again. Retaking the can, she swatted his ass once more and stopped. Working the top over her head, flung it off into the surrounding dark.

He gazed up at her orange-sized breasts. But he directed most of his attention to her bobbing girl-prick. What a monster it was. She bent down to him, worked up a mouthful of spittle, spread his raw red cheeks, and spat on his asshole.

Standing, Quinn Landry shimmed out of her skirt and kicked off in the general direction of a rack. She spat on her meaty pork, rubbed it, stroked the shaft, and spit more sputum to lubricate herself.

"Hands and knees, baby."

Squatting above him, Quinn pressed the massive bulbous head into his asshole. She spat more on the opening.

"Ready or not, here I cum." thrusting her hips hard, she dove several inches into him.

He panted and moaned into the musky air of the dungeon. The mustiness amplified the seduction of his Mistress. His ass ached as the head pushed deeper inside him. Thrust, withdraw, go deeper, retreat, hammer in, withdraw, and repeat. With each thrust, she invades deeper into his shitter.

Quinn establishes her dominance by digging fingernails deep into the tender flesh of Rich's neck and scalp. Her attack inside his ass was more fevered and angry than he'd experienced with college roomy.

"Who's my bitch?"

"I'm your bitch," he responds, his breathy exclamation soft, loving, and pained.

Mistress Quinn pushed his chest to the concrete and yanked his head back as she pounded more of her girthy monster into her guts.

His ass stretched to accommodate the invader.

She spits on her meat again. Fucking into Rich brutally hard. He surrendered to her vicious charms. Richard and Quinn moved their bodies in rhythm. For his part, Rich no longer inched forward with each thrust, but pushed back into the force.

The lining of his ass massaged her prick. The Mistress arched her back as she humped her toy. The manginess of the dungeon didn't matter. They made wild, violent love in the darkness.

Suddenly, she stopped, pulled her anaconda free, and straddled him.

"Get on your knees and use your mouth to service me." without saying more, she turned away, ambled to a table, turned around, and leaned back into it. "Crawl to me and obey."

His insides ached for her return. The thought of her prick with all the nastiness from where it had been thrilled and revolted him. Crawling on his belly, he made his way to her. Kissing her shoes, licking his way up your legs, he ascended her body. Slowly making his journey to her massive girl-pecker.

The dominatrix's thick shaft hung in front of his face. He opened his mouth and took her stiff prick into his mouth. He sucked the shaft deep into his willing mouth. Nuzzling his nose into Quinn's thick crotch hair, rubbing his face against her.

She tasted of sweat and sex.

Taking a handful of his hair, she pushed him off her penis.