Anthony huffed and rolled his eyes at his mother’s question. He was in the back seat of the family SUV, on the way to his uncle’s new house for Sunday lunch. His mother had her back to Anthony and didn’t see his reaction. His dad snickered. He had witnessed Anthony’s reaction in the rear view mirror.

They were driving to Anthony’s paternal uncle Mario’s new home. Mario had recently married again. His new wife, Rachel, had purchased two seats for an environmental awareness charity dinner that Mario wouldn’t be able to attend. The date conflicted with the yearly union convention in Las Vegas. Anthony’s parents and his uncle would attend the convention.

Anthony’s dad, Robert, chimed in, “Leave the kid alone, Marie. When I was our son’s age, I wouldn’t want to accompany my aunt to a charity dinner, either.”

“Thank you, Dad!” Anthony sighed with a sense of relief.

Marie turned in her seat to look at her son. “It a great opportunity to network for potential business relationships. What good is your engineering degree if you don’t look for opportunities to leverage it for your benefit? You’re twenty five years old, Anthony. It’s time to think seriously about, and start planning your future.” Marie turned away from her son and added, “Besides, your aunt Rachel could help brush up on social graces. She’s well versed in manners, conversation, etiquette, and fashion.”

Robert chuckled, “Old money doesn’t mix with new money, Marie. Anthony is perfectly content with learning, and eventually taking over the family construction business from me and my brother.”

Marie huffed, “All I’m saying is that it would be a positive life experience for our son.”

~

Rachel greeted her three guests at her front door with hugs and kisses on their cheeks. “I’m thrilled to finally have you over to our new house. Mario is the backyard ‘grilling and chilling’ - as he refers to barbequing.”

Anthony handed a bouquet of Amethyst Orchids to his aunt while his parents made their way to the backyard.  “Nice to see you again, Aunt Rachel.”

“How very thoughtful and sweet. They’re beautiful. Thank you, Anthony,” Rachel smiled as she took the bouquet. “Go say hello to your uncle while I put the flowers in a vase.”

Anthony followed Rachel and couldn’t help himself from checking out her tight, slim form. Her long, chestnut brown was tied in a springy ponytail that swayed and bounced with each step. Her snug fitting, faded blue jeans hugged her shapely hips and tight ass. The bottom hems of the jeans were rolled up well past her delicate and tanned ankles. The half sleeve, off the shoulder, flower patterned blouse teased Anthony by revealing about six, tanned inches of the small of Rachel’s back and slim waist.

Anthony thought to himself, “Uncle Mario is a lucky guy,” and grinned as he continued to ogle his aunt’s tight ass wiggle.

~

After everyone had finished eating, Rachel announced that she had made Tiramisu for dessert as she stood up from the table. “I know it’s Anthony’s favorite,” she chuckled to her husband.

Mario laughed and said, “Jeez, I completely forgot.” He looked at Anthony and asked, “Hey champ, could you hook up a new printer to our computer? I got a shit load of printing to do for work.”

Anthony nodded, “Sure, Uncle Mario. Where’s your computer? I’ll do it right now. It should only take a couple of minutes.”

His uncle gave Anthony the thumbs up and replied, “Upstairs, in the bedroom. The printer is still in the box. Thanks champ, I owe you one,” Mario smiled at Anthony.

Anthony excused himself from the table and headed upstairs. The door to the bedroom was open. Anthony spotted the monitor of the computer on a long, wooden desk against the wall opposite the bedroom door and headed towards it. As he entered the room, something in his peripheral vision caught his attention. He turned his head and focused on what had caught is eye.

The mirrored, sliding door of the shoe closet was open. Anthony honed in on a very specific pair of women’s shoes. Of all the shoes neatly displayed on the five racks, a single pair of shiny, red stilettos on the middle rack caused Anthony’s cock to twitch.

Anthony turned towards the shoe closet and inspected the stilettos. He tilted his head to the side, craned his neck and noticed that the entire outer platform, soul and bottom of the shoe was the same, sexy, shiny color of red. The finish on the leather made them look wet. As if a fresh coat of red paint had been flawlessly brushed over their entire outer surface.

He decided that he would inspect his aunt’s high heels in a more intimate manner after he connected the printer to the computer. As soon as he had the printer working; he revisited the shoe closet and focused his attention on the objects that had aroused him.

As far back as Anthony could remember; he had always been turned on by high heels. Stilettos make a woman's legs appear longer and more toned. To balance themselves on high heels, ladies are  forced to push out their chest and derrieres, which puts their breasts and asses more prominently on display.

Anthony grabbed his cock. It grew to full erection quickly. A sudden rush of adrenaline made him shiver as his fingers caressed the stilettos. He was half expecting to smudge their surface and that his fingers would be left stained with red paint.

Its thin five inch heel was sleek and sexy. He imagined how his aunt would look in the slutty footwear. How her calf muscles, tight and straining, would ripple beneath her tight skin and extenuate that sexy line that starts just below the knee and runs down the entire length of the side of a woman’s calf when she’s in heels.

Anthony loved that sexy line on a woman’s calf. He also loved the locked position and steep angle that stilettos punishingly trap a woman’s foot in. What Anthony loved the most about a woman in heels was how their back over-arches and creates that ‘fuck me’ angle between their upper back and ass.

Catching a glimpse of a woman’s breasts bounce and jiggle on their chests as they walked in high heels was always a stimulating sight for Anthony. His aunt had large breasts. Anthony began to fantasize Rachel naked and walking towards him in the red stilettos he was admiring and became increasingly hornier.

“Fuck! I gotta come!” Anthony gruffly panted.

He closed his eyes and imagined his aunt slipping her slender foot into the shoe he was holding. He pulled down the zipper of his pants and freed his throbbing, twitching cock as he fantasized about watching Rachel’s painted toes slip past the vamp, and into the red stiletto.

Anthony shut his eyes. “Fuck!” he growled through clenched teeth and began to stroke his fully erect cock.

His mind flashed provocative images of his aunt in various states of dress - but always wearing the same pair of red shoes that had triggered the profound sexual reaction in him. Anthony threw a quick glance at the open doorway and made a split second decision. He had to come. He had never experienced such an immediate and intense state of sexual arousal.

His cock throbbed with such an intense force that it caused Anthony pain. He had to fuck his aunt’s red, platform stilettos. The urge was beyond anything he could control. He’d wipe his cum out of her shoe with toilet paper and flush all evidence of his impromptu, fetish fuck down the toilet.

He tightened the grip around his engorged cock and stroked it with abandoned urgency. The pressure at the base of cock quickly peaked to the inevitable point of no return. Holding on tightly to the stiletto with both hands, Anthony aimed his cock at the opening beneath the stiletto’s vamp and thrusted into his aunt’s shoe. The swollen head of his cock crashed repeatedly against the inside of the closed, tapered toe. Anthony grunted and grimaced each time the tip of his cock met the resistance of the tight, leather cavern. It only took a couple of thrusts for Anthony’s cock to erupt and fill the stiletto with cum.

Anthony’s euphoria lasted only a few seconds. He was brought crashing back to cold reality by the sound of his name leaving his aunt’s lips, “Anthony!” Her over emphasis of the first syllable of his name unmistakingly implied the unspoken question - ‘What the fuck are you doing?’

Rachel’s reflex reaction was of great shock and anger at the sight of Anthony convulsing in uncontrollable spasms as if a demon was trying to escape from within him. She was unaware that her baser instincts had caused her body to react in a very different manner. Rachel’s pussy clenched and became very wet, very quickly at the sight.

Anthony couldn’t move. He was paralyzed and dumbstruck. He wanted to shrivel up and disappear off the face of the Earth. He turned his head to the bedroom doorway and was mortified to see his aunt Rachel standing there with a plate of Tiramisu, fork and napkin in one hand. What could he possibly say to her? Was there any point in saying anything at all? He stared blankly at her as some part of his brain managed to make his mouth move and stutter, “I’m so sorry.”

A sudden and loud ringing in Anthony’s ears muted his own voice and what Rachel had replied to his apology. The room began to spin out of control and his vision blurred for an instant. The soft touch of Rachel’s hand on his cheek brought Anthony back to the moment.

“Are you okay?” she asked him with a deep sense of concern.

Anthony took a deep breath and shamefully replied, “Ya. I’m so sorry. I can’t explain why I did what I did. It - it just sort of happened.”

Rachel stared at Anthony’s cock for a silent moment. It was semi hard and still twitching - buried in her stiletto. She placed the desert on the desk and turned to face Anthony. With one hand on her hip and her right foot tapping, she extended her hand. “Are you finished defiling my Louboutins? Can I have my shoe back?” she half sneered to emphasize how upset she was over the ordeal.

Anthony nodded as he handed Rachel the stiletto. He half turned away from his Aunt, tucked his cock back into his pants and pulled up his zipper.

Rachel was very angry at Anthony and the tone of her voice conveyed it clearly. “It took me a long time to get these. They’re nine- hundred dollar Louboutin, five inch, platform stilettos. Have you any idea how long it took me to learn to walk properly in a heel that high? I was going to wear them for the charity dinner that you declined to accompany me to - for your information, young man.”

“I’ll get you another pair, I swear. I’m really, really sorry,” Anthony groveled for forgiveness.

Rachel gasped when she looked into the toe of the stiletto and realized how much cum Anthony had fucked into her shoe. She stared at Anthony, slapped her thigh with her free hand and asked in disbelief, “Why? I mean, you’re a very handsome young man from a wealthy family. You surely have your pick of the young ladies. Any girl would be impressed and more than satisfied with the impressive girth and length of your cock. Why would you fuck and blow your load in a Louboutin? Specifically, my Louboutin, platform stiletto?”

Rachel chuckled to herself when she realized how unbelievable the question she had asked the mortified Anthony sounded. “You’re a young man - hormones and all that jazz - I get it. You studied hard and graduated in the top percentile. Your uncle tells me you work hard with him and your father. By all accounts, you're a fine young man, Anthony. Let’s put this behind us.”

Anthony exhaled hard and hugged his aunt. “Thank you! I’m really sorry, Aunt Rachel.”

As angry as she was at having had her privacy violated and her new shoes possibly ruined, her pussy was still wet. Rachel gasped when her clit began to throb from the sensation of Anthony’s semi-hard cock pressed into and twitching against her flat belly.

Rachel chuckled nervously to hide her increasing arousal, “No problem. If anyone is to blame, it’s Christian Louboutin for making such sexy shoes. The salesgirl warned me that platform stilettos drive men crazy.” Rachel grinned mischievously as she allowed the thoughts she was trying to stave off - thoughts of teaching the young stud a lesson - crept into her mind. She was surprised at how quickly she gave in to her lecherous thoughts. “I want you to call me Auntie Rachel from now on,” she demanded.

Anthony thought it was a small price to pay for being caught fucking and coming in her shoe.

“Not a problem.” Anthony smiled, “Auntie Rachel.” 

“And,” Rachel paused as she took a step back and stared Anthony down to let him know she was dead serious. “You are going to tell your uncle and parents that you’ve had a change of heart and decided to accompany me to the charity dinner. It’s a black tie event. You’ll have to wear a tuxedo.”

Anthony was a bit shocked and confused by his Aunt’s demand. She also must have undoubtedly been embarrassed at having witnessed the lewd act of him fucking and coming in her shoe. So, why would she want to spend an evening with him?

“Really?” he sheepishly asked.

Rachel nodded and replied, “Yes. Really. Consider it your punishment for filling my new shoe with your spunk.” She couldn’t help grinning at having the upper hand over the lewd situation.

Anthony knew he had gotten off easy - he had no choice but to begrudgingly agree to accompany her.

Rachel pointed to the plate she had placed on the desk and said, “Take your Tiramisu and go back to the table. I’m going to clean my Louboutin.”

Anthony did as Rachel instructed and scurried out of the bedroom.

Rachel huffed and cursed under her breath as she made her way to the master bathroom. She positioned the cum filled shoe over the toilet and took one last look inside it. As upset as she was, looking at Anthony’s cum sent a tingle through her clit. “Such a waste of perfectly fine cum,” she softly snickered.

Rachel grinned as a devilishly, perverse thought popped into her mind. Instead of pouring the cum into the toilet, she kicked off one flip-flop and placed the stiletto on the floor.

“What the hell,” she smirked, “I’m still on the right side of forty.” Rachel had recently turned forty-four. “My five inch, fuck-me-heels wearing days are numbered. Let’s live a little and enjoy a cheap thrill.”

Her grin widened as she carefully slipped her foot into the soiled shoe. She was pleasantly surprised to find that Anthony’s cum was still relatively warm. Rachel gasped when the thick, wet warmth made contact with her toes and the ball of her foot. She moaned at the sensation of the sticky and slippery liquid covering her foot whilst she wiggled her toes.

“Fuck,” she panted, “That feels so good.”

Rachel knew that she would never cheat on her husband. But the option to initiate a little naughty fun was definitely something she was up for and could easily keep compartmentalized.

~

The day after Mario and Anthony’s parents left for Las Vegas, Rachel accompanied Anthony to his tuxedo fitting. The morning of the charity gala, Rachel picked up Anthony’s tuxedo without informing him. When she got home, she called Anthony and instructed him to be at her house at six. “You can get dressed here, Anthony,” she said in a slightly stern tone.

Anthony knocked on his aunt’s door at fifteen minutes before six. A minute passed, just as he was about to knock again, the door opened and Rachel greeted Anthony wearing only a sheer, black, silk half cup bra and matching black, sheer, silk panties.

She grinned at the shocked Anthony and said, “Pick your tongue up off the floor and come in, Anthony.” She turned and walked away from the stunned young man. Rachel looked at him from over her shoulder as she walked, and casually added, “You’re early. Your tux is in my bedroom. We can get dressed together, I guess.”

Anthony swallowed hard and nodded. “Sure, Auntie Rachel.” The words barely creaked out of his tight throat.

His cock twitched and quickly grew to full hardness. He panicked at the thought of his aunt noticing his hardon through his jeans. Regardless of how uncomfortable Anthony felt, he couldn’t pry his eyes away from his aunt’s ass. Her sheer panties left nothing to the imagination. 

Anthony followed Rachel up the stairs. His eyes were glued to Rachel’s ass as it swayed seductively from side to side. To add to his dilemma, when Rachel lifted her legs to ascend each step, it provided Anthony a flash of her plump, hairless pussy.

“Are you enjoying the view, Anthony? Is your cock rock hard?” Rachel teased him in a breathy voice.

Anthony remained silent. Rachel stopped at the top of the stairs and turned to face him. Her crotch was level with Anthony’s eyes. He gasped when he realized he could clearly make out his aunt’s freshly shaved pussy.

Rachel grinned, placed her hands on her hips and widened her stance to tease Anthony. Beads of sweat pooled on Anthony’s brow. His cock strained against the denim crotch of his jeans and created an impressive bulge that didn't go unnoticed by Rachel.

She coyly asked, “Would you like to come, Anthony?”

A feral grunt rumbled in his throat as he nodded.

“Good. Come into my bedroom and strip,” she ordered.

Rachel turned around and led young Anthony to her bedroom; like a spider enticing her victim to her web. She headed to the shoe closet and grabbed a red, platform stiletto in each hand. She walked to her bed, sat on the edge of the mattress and placed the stilettos on the floor, between her feet.

Rachel grinned as she watched Anthony strip off his clothes. She licked her lips and stared hungrily at his rigid cock.

She met his gaze and asked, “Do you think I'm sexy, Anthony?”

He nodded and gasped, “Yes, Auntie Rachel. Very much so.”

Rachel eased back and rested her elbows on the mattress. She spread her legs wider and cooed, “Come closer, Anthony. Get real close to what I know you’re aching to fuck.”

Anthony knelt between Rachel’s spread thighs. His eyes widened and locked onto the glistening slit beneath the sheer crotch of her panties. Her pussy lips were spread just enough to give Anthony a teasing glimpse of her wet, pink inner folds.

His eyes shot to the stilettos on the floor between Rachel’s feet and Anthony licked his lips.

“Stroke your big cock for Auntie Rachel,” she purred and thrust her hips seductively towards Anthony’s face.

Anthony gripped his cock and pumped it as he alternated staring between Rachel’s legs and the red fuck-me stilettos. The scent of her perfume and pussy juice mixed in his nostrils caused Anthony to shiver and raised the hairs on the back of his neck.

“Mmm. That’s so fucking hot, Anthony. Watching you stroke that big, beautiful cock is making Auntie Rachel’s ... cunt … drip,” she moaned and bucked her hips in a painfully slow and deliberate fucking motion. The word ‘cunt’ had a very positive effect on Anthony. Rachel noticed his reaction and said it again. “Do you like Auntie’s cunt?” she cooed and emphasized the hard ‘K’ in the dirty word.

Anthony grunted and nodded.

Rachel sat up and said, “Stand up.”

Anthony released his cock and jumped to his feet. His cock twitched inches away from Rachel’s lips. He could feel her breath on his shiny and swollen head. Rachel grinned and sent a wisp of her warm breath to caress the shaft of his cock. Anthony knees buckled.

Rachel pouted, “I want a big load of cum from you. Can Auntie Rachel get a big load from your big cock all for herself, Anthony?”

“Yes! I can come just for you,” he gasped as another shiver shot through his body.

Rachel picked up one of her stilettos and cooed, “Fuck Auntie Rachel’s sexy shoe, Anthony. Fuck it good and hard and fill it with your jizz. Just for your naughty auntie.”

Anthony aimed his cock under the vamp of the stiletto and shoved his cock into it. He thrust in and out of the stiletto that Rachel held on to with both her hands. With each urgent thrust, the swollen head of his cock slammed against the closed, tapered toe. He grunted and snorted like a rutting stag. It only took a few thrusts for Anthony’s cum to start to build at the base of his cock.

“Ooo! Yes Anthony! Fuck my slutty stiletto with your big, bad cock. Pump it full of your spunk.” Rachel pursed her lips and seductively cooed, “Just for your dirty, Auntie Rachel.”

The dirty talk multiplied every sensation coursing through Anthony’s body. His breath caught in his throat, every muscle in his body tensed. With a shiver and long, raspy moan, Anthony emptied his balls. Rachel oohed and aahed as she watched Anthony’s cock blast spunk into her stiletto. “Oh my goodness, Anthony! That’s the biggest load of cum I’ve ever seen!” she exclaimed.

Having his aunt almost naked, watching him, and giving him jerk off instructions heightened his senses to mind bending levels. Waves of prickling and stinging sensation wash over his entire body long after the last drop of cum left his cock.

Rachel picked up the other stiletto off the floor and carefully poured half of Anthony’s cum into it. She curled her painted toes and slowly slipped her feet into the shoes as Anthony watched on in perverted delight.

“Fuuuck,” she moaned as she wiggled her toes and squished the cum under the balls of her feet. The hot, thick liquid squeezed up in between her wiggling toes. “Ohh, that feels so fucking good!” Rachel gasped as she stood up. She hugged Anthony and kissed him on the cheek.

Anthony savored watching his sexy aunt saunter half naked around her bedroom. He had been longing to see her in stilettos and witness that sexy over-arch in her back locked and strictly constrained by the high heels. That over-arch simulates body language that a woman is ready to fuck and triggers arousal in men. The thought of his cum being squished and slathered all over and in between Rachel’s toes only added to Anthony’s thrill.

Rachel purred, “The feeling of your hot spunk being squeezed and squished between my toes is ... indescribable.” Rachel tilted her head back and closed her eyes. She gasped, “Ooo! I can feel your cum under my toenails, too, and I love it! This is making me ridiculously horny. I can’t wait to get to the party to mingle and dance. Knowing that we share a dirty little secret - that my feet are covered with your cum - will edge me to the cusp of an orgasm and keep my pussy clenching and dripping wet all night.”

Anthony nervously offered, “If you need a refill at the party, Auntie Rachel, we can always sneak to the car and … I mean, if it’s okay with you.”

Rachel nodded slowly and replied, “Anthony! You are a deliciously, deviant young man. Such a thoughtful, young gentleman. I don’t see how I could possibly refuse your indecent and lascivious offer.”