“Trick or Treat!”
Henry opened the door for the hundredth time that evening with the nearly empty bowl of candy in hand.
“Oh, wow, what do we have here?” he asked with joy. Halloween was one of Henry’s favorite holidays. He truly enjoyed seeing all the neighborhood kids in their costumes. His favorite were the new parents with the babies dressed up as miniature versions of animals, fruit, or whatever. He gave mental bonus points for matching parent costumes. His next favorites were the elementary kids dressed in super-hero costumes that really got into their characters. Henry even tolerated the goth teenagers dressed in all manners of death and fright.
“We’re the Avengers!” exclaimed a group of what must have been about fifth graders.
“I see that, wow!” Henry mirrored back their excitement. “Captain America, Black Panther, Hulk. Very cool!” Henry reached out with the candy bowl. “Here you go, kids, help yourself. There’s not much left, so why don’t you guys split the rest. Super heroes need lots of sugar.”
“Wow, mister, thanks!” the kids said together as they scrambled to grab the last of the full size Reese’s, Butterfingers, and other assorted sweets. Henry didn’t skimp when it came to Halloween, and all the kids in the neighborhood knew it. His house was always popular. Henry didn’t even mind too much when he noticed some kids came more than once.
Henry and his late wife had never had kids, despite their best efforts. It just wasn’t meant to be. Instead, Henry enjoyed being an uncle, and since his wife’s passing a few years ago, he tried to look out for the kids in the neighborhood.
Iron Man was last in line and he looked hesitant to take the last two candy bars in the bowl. Henry gave him a reassuring smile and a nod and hoped the kid was smiling under his plastic mask.
“I like your outfit, too, mister,” Iron Man said before he turned and ran down the lit walkway to catch up with his friends. Henry looked down at his navy blue airline pilot costume, complete with shiny brass wings, ringed cuffs, and a wide uniform cap. He sighed and closed the door, then flicked off the front porch light switch to signal to the kids he was out of candy for the night.
He’d hoped to spend the evening with his new girlfriend. Handing out candy would have been much more fun together. Beautiful women in slutty costumes was his second favorite thing about Halloween. Rebecca was ten years younger than Henry and he’d hoped that she would come through with a great costume. She worked as a flight attendant, which had inspired Henry’s pilot costume, but unfortunately she was called into work at the last minute and had to cancel on him for trick or treat.
Henry plopped down on the couch and took off his cap. He missed the days when he and his late wife, Helen, had been invited to adults only Halloween parties. His wife had been gorgeous and could slut it up with the best of them at Halloween. Henry’s favorite costume of hers had been the slutty football player. She’d worn a crop top jersey with no bra underneath and the number 69, super short running shorts, and black lines on her cheeks. Henry had been a referee, of course. He couldn’t keep his eyes off her all night, and when she reached for something on a high shelf he’d been able to see just the right amount of underboob. Another time she’d gone as a slutty policewoman with a micro mini-skirt, a tiny uniform top with lots of cleavage, handcuffs, night stick, and fuck-me shiny pleather boots. Henry had been a prisoner that year. They’d been very good together.
He still thought of Helen often. They were great together in many ways, and they’d always had such great sexual chemistry together. There’s nothing they hadn’t tried at least once, and they’d been faithful to one another their whole lives. They satisfied the other’s needs in a way most couples dream of. Of course, the cancer had changed some of that at the end, but Henry’s deep love for her meant that his priorities just shifted to care for her in loving ways. Thankfully, for Helen, the end had been fast without much suffering.
Henry grieved for a long time before he felt like he could start dating again. His family and friends had been supportive, but there’s nothing that can replace your best friend. He spent many days, nights, and holidays alone and eventually his loneliness was more than he could handle. He was too young to lose interest in sex and companionship, so he started dating again.
He’d dated a few women before he met Rebecca. She brought vitality back into his life. There was the age gap, which created more laughter than problems, but she had a positivity and adventurous spirit that Henry found so attractive. And she was smoking hot. She was tall and athletic, whereas Helen had been short and buxom. Rebecca was incredible in the bedroom and liked to role play scenarios like Helen had done. That’s another reason Henry had always loved Halloween; it was the perfect excuse for an imaginary scenario that could be played out in the bedroom after all the candy was handed out.
Henry walked to the kitchen and poured himself a glass of expensive red wine and grabbed the one Butterfinger candy bar he’d saved for himself. He sat down, alone, at the kitchen table and opened the wrapper. “Happy Halloween,” he said to himself ironically as he took the first bite and followed it with a swig of wine. Despite being alone, the combination of the cheap chocolate and fine wine made him smile.
He was surprised when he heard the doorbell. He was certain he’d turned out the porch light to indicate he was out of candy. Sometimes teenage kids just didn’t take the hint, Henry thought, especially when they knew he handed out full size candy bars. Henry sighed and grabbed the first snack he could find in the pantry, a handful of individually wrapped beef sticks, and headed to the door, reminding himself that he enjoyed this.
He opened the door expecting to find some punk teenagers barely in costume. Instead, Rebecca stood there still in her flight attendant uniform. She was leaning against the doorframe and she smiled warmly at Henry. After a moment of surprise passed, Henry whistled and checked her out, up and down. Her navy-blue blouse had several buttons unbuttoned and he could see her black lacy bra underneath. Her form fitting top accentuated her small waist and the pencil skirt showed off her subtle rounded hips. She had removed her typical black stockings and Rebecca’s tan legs were visible above her sexy heeled shoes.
“Trick or Treat, big boy,” she said sultrily. “What do you have for me there - your beef stick?”
Henry laughed when he realized he was still holding a wad of shrink-wrapped beef sticks. “Yes, I suppose I am! Come in, please,” he said as he dropped the sticks in the empty candy bowl next to the door.
“I got off work early tonight and thought I’d make a surprise appearance. I hope I’m not interrupting anything,” she said honestly.
“No, not at all, I just handed out the last of my candy to a group of Avengers. Come on in, I’ll get you a drink,” Henry said as he headed to the kitchen. “What’ll it be?”
“Bloody Mary, of course, it’s Halloween!” Rebecca said coyly, then laughed. “Just kidding, I’ll take some sparkling wine if you have it.”
“Sure, I have a great sparkling rosé,” Henry replied. Rebecca made herself at home on the couch. Henry busied himself with her drink, grabbed his own off the table, then he returned to the couch with their wine. Henry handed Rebecca the fluted glass of bubbles and settled on the couch next to her.
“I’m so glad you got off early, I was just thinking of you. Well, you and Helen.” Henry always made it a point to be honest with Rebecca about himself and about his deceased wife. Rebecca took this as a sign of trust. “I’ve always loved Halloween for the slutty costumes,” he added with a smile, “and this year was turning out to be a dud.”
“Well,” Rebecca said, “the night is young, there’s a full moon out, and we have matching ‘costumes’ - even if mine is the real deal. I think we can have some fun with that.”
Henry felt his cock twitch in his pants at Rebecca’s words. He loved how she was so often the adventurous one in the relationship.
“Where are you getting back from?” Henry asked.
“Bangkok, of course!” Rebecca laughed. “At least that’s where I hope I’ll end up tonight!”
Henry’s cock twitched in his uniform pants at Rebecca’s joke. “Seriously, baby?” he asked.
“No, it was Cincinnati, but that doesn’t sound nearly as punny,” she replied.
“And how was Cincinnati?” Henry asked as Rebecca shifted in her seat, exposing more of her black lacy bra as her flight attendant uniform top opened slightly. He was rapidly losing interest in Rebecca’s itinerary.
“Who cares, my love,” Rebecca said, leaning forward on the couch. “I just want to see if you’re glad I’m here.”
She leaned in toward Henry and gave him a deep kiss. She swirled her tongue around his just to let him know she was serious. She tasted like rosé as her soft lips caressed his mouth. Henry cupped Rebecca’s cheek in his hand and slid his fingers into her long brown hair.
Abruptly, Rebecca pulled back. “Hold on there, captain,” she said smiling. “We need to cover some important safety information before today’s flight.”
Rebecca stood and stepped back away from the couch. She slowly reached toward her blouse and undid another button, revealing more of her lacy black bra. Then she stood erect and looked very official as she began her pre-flight instructions.
“Before departure please ensure your cock is in the upright and locked position,” she started as she ran her hands up her hips to her breasts. She unfastened the rest of the blouse buttons, revealing the olive skin of her flat stomach. She opened her blouse and untucked it from her skirt, then dropped it to the floor behind her. Henry was transfixed by Rebecca’s gorgeous body and her perfect tits pushing up from behind her sexy bra.
“In the event of intercourse, you may hyperventilate. Oxygen masks are not available, but should you become lightheaded please place your head between your partner’s legs,” she said laughingly as she made a gesture toward her crotch.
Rebecca then moved her hand to her hip and slowly unzipped her skirt zipper and wriggled her hips side to side while inching her skirt slowly down her body.
“For your enjoyment, smoking hot sex is allowed in all areas of the plane, including in the seating areas, the lavatory, and of course, the cockpit.”
Rebecca’s fitted skirt cleared her athletic hips and fell to the floor at her feet. She slowly stepped over the fabric in her heels, then turned to face away from Henry. His eyes widened with delight at the sight of her shapely ass and small black thong. His cock strained against his pilot costume pants.
“In the event of emergency arousal,” she continued, “all exits may be used for your pleasure.” Rebecca bent at the waist, keeping her long legs straight, as she reached a hand between her thighs and gently stroked her pussy through the thin cloth. “Please take a moment to locate your nearest port of entry, keeping in mind it may be behind me.”
Henry laughed as Rebecca looked back and smiled at Henry as she continued to stroke herself. Henry couldn’t take any more teasing. He stood and quickly removed his pilot hat and jacket. Before he could undo his belt buckle, Rebecca straightened and turned back toward him.
“I’m sorry, sir, but I’ll have to ask you to remain seated while the show is in progress with your belt buckled low and tight around your waist.” She smiled, placed a hand on Henry’s chest and gently pushed him back onto the couch. Henry sat and leaned back into the cushions with a wide smile.
Rebecca took a small step forward then kneeled onto the couch and straddled Henry’s legs. Her knees pressed into the couch cushions on either side of Henry’s hips, and she ground her pussy against Henry’s straining erection as she leaned forward and rubbed her cleavage against Henry’s face. The lace of the bra felt rough and contrasted with the softness of breasts. Henry’s hands caressed her back and shoulders as the feminine floral scent of her perfume overwhelmed him. Rebecca moaned and reached her hands back, and with a smooth practiced motion unhooked the clasp of her bra and slipped her arms out of the straps.
Henry eagerly cupped and kissed each of Rebecca’s breasts which senT shivers of pleasure through her body. Rebecca tossed her head back and her long brown hair cascaded down her back. She pulled Henry toward herself, encouraging him as he sucked on each nipple in turn.
After several moments Rebecca pulled her body back and leaned down to kiss Henry again, passionately exploring his mouth with her tongue. Henry reached his hand between her legs and caressed her swollen pussy through her lacy panties. Rebecca moaned into Henry’s mouth as she bucked her hips in time with his hand. Finally, Rebecca backed away again and lifted her legs off of the couch to stand before him.
“Please remove my underwear before removing your own,” she continued breathlessly and with a smile. Henry reached up and began to pull down on her black panties. “My pussy may be used as a pleasure device. You may use your mouth to stimulate me in the event of my arousal.”
Henry leaned forward as Rebecca flexibly placed a long leg up on the back of the couch behind him. Her bald pussy spread before him. Henry was amazed at her swollen pussy lips and immediately began licking between her labia. The salty-sweet taste of her wetness was intoxicating. Rebecca cupped his head in her hands and pulled him toward herself. Henry’s hands slid up to her ass as he licked and kissed Rebecca to her first loud orgasm. Rebecca shivered in delight as she came lightly from his attention, but was hungry for more.
“Ma’am,” Henry said, trying to stay in character, “I’m going to need you to return to your seat, we are coming in for a landing.” Rebecca placed both feet back on the floor, then Henry stood and kissed her before gently turning Rebecca around and gestured toward the couch. Rebecca smiled and sat down, then spread her legs, licked her fingers, and began stroking her clit in slow circles.
Henry quickly undid his tie, and nearly ripped a shirt button as he hastily undressed. His belt slowed him down for a moment, but soon his pilot costume was on the floor and he stood naked with his cock jutting out like a fuselage.
“Mmm, captain, my runway is open,” Rebecca said playfully, then leaned forward to tease Henry with a brief kiss on his cock before turning around on the couch. She kneeled on the cushions and rested her elbows on the back of the couch, then turned her face back toward him with a “fuck me now” look.
Henry took a step toward her exposed pussy and slid the tip of his cock against her wet pussy lips, then drove his long cock all the way inside of her in one smooth motion. Rebecca yelped at the suddenness of his entry then sharply inhaled, but a moment later she acclimated to his size and pressed her hips back toward him.
Henry gripped both of Rebecca’s hips and began thrusting his cock in and out of her tight cunt. He grunted and blew out a long breath to avoid cumming too quickly in her tightness, but the moment passed and he continued to thrust in and out of Rebecca. She moaned as he filled her, and she reached a hand between her legs and aggressively rubbed her clit as Henry fucked her.
Henry was focused on the feminine shape of Rebecca’s petite shoulders, her thin waist, and her broad hips as his cock slammed into her again and again. He released the grip with one hand and slapped her ass, leaving a slight impression of a handprint.
“Yes, captain, give it to me!” Rebecca moaned as the sting on her ass subsided. “God, I want your cum so badly. Fuck me like the whore you want me to be!”
Henry slammed his cock deep into Rebecca and held it there. He could feel his balls contracting, preparing to empty themselves inside of her. He let out a long breath, eager for their fucking to last longer. Rebecca could feel his cock swell inside of her and squeezed his cock with the walls of her pussy, teasing him, as her fingers continued to fly against her clitoris.
Henry felt the pressure and knew he was about to explode, so with all his willpower he slid himself out of Rebecca. The sudden emptiness made Rebecca yelp again and she stopped her stroking. She looked back to see Henry’s primal hunger written across his face. He grunted again and gruffly pulled on one of Rebecca’s hips, flipping her over onto her back. Rebecca grinned, happy with Henry’s obvious attraction, and scooted back to position herself against the couch armrest, then spread her legs wide so one leg was against the couch cushions and the other was on the floor.
“Come here, captain, the flight’s not over yet,” she said as she crooked a finger in a come-hither motion. Henry kneeled on the floor and leaned forward to devour her cunt, lapping at her pussy with an intensity that nearly pushed Rebecca over the edge once again. Before she came, though, Henry stopped and positioned himself over her. He slid his cock inside of her once again and began thrusting. Rebecca’s head fell back against the couch as she continued to finger herself while Henry fucked her.
Henry felt Rebecca’s pussy walls contracting again and looked into her eyes. He watched her pupils dilate and she bit her lower lip as she began moaning, then her body was convulsing in a whole body orgasm. Henry felt his balls begin to contract once again and knew there would be no stopping it this time. He thrust into Rebecca’s tight cunt a few more times, then pulled out and grabbed his cock. He pumped twice before spurts of cum erupted onto Rebecca’s stomach and tits.
Rebecca watched enthralled as Henry’s cock shot the last remaining bit of cum onto her body, her own orgasm still waning. Then she took a manicured finger, scooped up some of his cum off her flat belly, and looked him in the eye as she sucked it from her finger. It tasted delicious, and was all the treat she wanted for Halloween. She continued to clean Henry’s cum off of her body and swallowed every last drop.
“Happy Halloween, baby,” Henry said.
“Thanks for flying the friendly skies,” Rebecca said with a smile.
