#1 MILF - Teen Halloween

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Nicci meets her monthly contractual obligation on Halloween.
6k words
4.24
21.3k
17

Part 2 of the 5 part series

Updated 02/25/2024
Created 02/25/2023
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CasualK9
CasualK9
165 Followers

To stop efforts at blackmail by an obsessed nineteen-year-old, Mrs. Nicolle Burton agreed to an ill-advised, poorly worded contract to do whatever he wanted for two hours once per month for one year.

Part 2 - October

Halloween was approaching, and it was Nicolle's favorite holiday. She had decorated the house with lots of spooky skeletons and lights and stocked it full of candy bars to give the kids who came to trick or treat. She had been working on a creepy music playlist on her phone when a new text banner hit her screen.

"What are you going to be for Halloween?"

She replied with another blank-faced emoji.

He replied with an eggplant and a tongue.

She replied with a clown face.

"I'm serious!" Matt, the nineteen year old superfan who'd wheedled, hustled and harassed her into an ill-advised 'blackmail contract,' wrote.

Nic sighed, "I assume you have something in mind?"

"I bet you have some great costumes."

"Probably not as many as you think."

"What's your sluttiest one?"

"Excuse me?"

"Come on! I'm SURE the #1 MILF has some super slutty costumes! Literally, all the girls my age have them!"

Nic thought about her closet. Off the top of her head, she recalled a French maid outfit, a slutty nurse, Harley Quinn, a slutty cop, a slutty angel, a Hooters uniform, Wonder Woman, and a few others her husband had bought her.

"What's your point?"

"I'm going to come trick or treating at your house, and I want to see you in your sluttiest costume."

"The contract says daytime - not at night."

"Won't everyone in your house be out trick or treating?"

"How should I know!"

"Well, make sure they are! LOL"

"I am so tired of you."

"I know!"

She sent him an angry face emoji.

He sent a crazy laughing emoji back.

Nicole groaned as she looked at her phone and typed, 'I'll text you when to come, and you better be here in 10 minutes, or it is SO not happening,"

A thumbs-up emoji was all he sent back.

She was fuming inside. Her favorite holiday was going to be ruined by this stress!

____________________________________________________

The next day when everyone was either at school or work, she took a break from her Zoom calls, went to her closet, and began trying on her costumes.

She had accumulated them over the course of her 15-year marriage. Many of them were that old. To her husband's recurring frustration, some had never been worn at all, but he never stopped trying. Her 'slutty' wardrobe was greatly enhanced by having a husband who was a horndog, she thought to herself as she admired her reflection in the full-length mirror of her master bedroom.

They all fit her - mostly like they did when they were purchased. Any differences were due to her looking even more curvaceous, shapely, and toned over the years.

"You know what, I look damn good for having three kids," she said aloud as she admired the reflection of her body stuffed into the slutty nurse outfit. Her boobs were pushed up almost to her chin, and the little dress just barely covered her juicy rear end in the back. Most of it was covered anyway.

She stood on her toes, crossed her legs at the ankles, and vamped for herself. She knew she looked stunning and gave herself a cocky smile and a duck lips kiss before moving to the next outfit.

She could barely get the skimpy Harley Quinn top over her shoulders and wiggled around comically in her bedroom, struggling with it. Eventually, she got the corset-like top into position and looked better than the image on the package. Her chest looked outrageous. It was nearly impossible to see anything else on her. Despite looking like the perfect embodiment of a big-chested Harley, she rejected the outfit in her mind. Not this one, she thought. Too much fucking work.

Wonder Woman? Too basic and overdone.

French maid? She watched herself pretend to dust in the mirror. Too much like lingerie and too obvious a fantasy. Way too sexual, she thought - no way I can answer the door in this.

The authentic Hooters outfit had always been a favorite. Her husband had even gotten one from her hometown in New Jersey for what he said was the sake of 'authenticity' though he knew she'd never worked there. Nicolle snorted in laughter at the memory. He was such a great guy, and she adored him, but he'd be so mad at her if he knew the trouble she'd gotten herself into.

She admired herself in the Hooters outfit and giggled to her reflection, "You want some wings with that?"

How about the white angel? It was just a halo and a pair of feathery wings on elastic. Stupid and lazy for times when she had to dress up but didn't feel like going to any effort775.

Slutty cop. That outfit needed to be of higher quality. Too sloppy and loose. Need to be more fitted to be very appealing. And the plastic handcuffs? Please!

Slutty schoolgirl? She tried on the little plaid skirt and the collared shirt that tied around in the middle to show her bare belly. She pulled her favorite black patent leather stilettos out of the closet - the ones she wore for work - and slid them onto her sexy little size 7 feet. She strapped the short, plaid tie around her neck with its Velcro closure and looked at herself in the mirror. God, this was SO trampy. Did she look fat? She snapped a mirror selfie and sent it to Brandi. "Too fat?" she wrote.

Brandi texted three flame emojis a few seconds later, and Nic laughed. She put down her phone and turned around. Unlike the nurse's dress, this one did not cover her ass much. Two or three inches of her big, tan cheeks were visible below the stretched hem. She faced the mirror again. Her dark nipples were visible under the white cotton oxford, and her huge boobs spilled like overstuffed pillows out of the small crop top. She flexed her leg muscles proudly. Running six miles away made them look toned as hell. She looked incredibly sexy and impossibly slutty, and there was no way in hell she could hand out candy in this outfit!

Still, she told herself she had to get rid of all these things. So many skimpy costumes and bikinis! All they did was get her in trouble. Next year, she vowed to wear a full Handmaid's Tale robe with the bonnet and everything. It had been too many years of all this nonsense. Even if she could still pull it off, she was feeling over it.

Then she laughed at herself. Handmaid's Tale would be next year. How could she not wear something that looked so good on her today? She was way too vain not to look super-hot in her costume if she could. She knew it, and it seemed like Matt did too. Slutty schoolgirl it was!

On Halloween night, Nic found herself frantically busy as always. She was dressing the 6-year-old in his adorable police outfit, getting her thirteen-year-old out with her friends, taking pictures of the kids, posting them on Facebook, organizing, and setting up her music and the fog machine on the front porch. Everything was perfect by dusk, but getting there was nuts.

For the first hour, she wore a classic catsuit with a cute, black, cat-ear headband in her pretty blonde highlights. When 7 pm rolled around, she ushered her husband and son out to meet his best friend on a buddy trick-or-treat tour she had hastily arranged with the kid's mom the day she got the text from Matt. She exhaled deeply as she watched them drive up the street, popped a Xanax to calm her anxiety from all the hustle, and ran upstairs to change. She texted a quick thumbs up to Matt and grabbed her schoolgirl outfit.

One look at how small it was, and she second-guessed herself. She couldn't greet kids at her house looking like that! She didn't want to meet Matt like that either! What had she been thinking when she picked it?

She peeled the catsuit off and dropped it on the closet floor. She took the cat-ear headband off and tossed it on the catsuit. Then, she took the nurse's outfit off a hangar and pulled the tight fabric over her head, struggling mightily to get it past her huge boobs, then wiggled the tight white cloth over her hips. She wondered why her tits seemed even more prominent than usual. Was she ovulating? Whatever.

She grabbed the cute white hat with its red cross, bobby-pinned it to her hair, and ran down the stairs as fast as she could while she listened to the doorbell ring and ring. Her house was always super busy on Halloween!

Nic flung the door open with a big smile and was greeted with a large chorus of "Trick or Treat!"

The front steps were filled with a throng of kids of all ages decked out in various costumes. She invited them to take one candy bar of their choosing, and one by one, kids filed up to the big tray next to the door to choose their favorite candy.

Nic looked spectacular in the skintight nurse's outfit. The MILF was barefoot and looked leggy despite her petite frame, perhaps because the dress was ridiculously short. Her boobs were pushed almost to her chin, and her cleavage was several inches deep. Her beautiful face lit up with joy as she watched the little kids excitedly grab a candy bar and stuff it in their bags. The dad's faces lit up with joy when they saw her standing beside the tray in that outfit, but the mothers tended to look much less pleased.

A steady stream of kids came through for the better part of fifteen minutes, and by the time there was finally a break in the flow, 2/3 of her candy was gone. She shut the door and went to look in the cupboard to see if she had anything she could add to the treat tray when the doorbell rang again. She swung it open with a smile and was greeted by two people dressed head to toe with full masks. Nicci had never seen these costumes before. She had no idea what they were.

One of them said, "Trick or Treat, Mrs. Burton! You look incredible!"

She immediately guessed it was Matt under the mask but didn't want to assume anything that could have made matters even worse.

"Matt?" she asked blandly, and her smile faded when he nodded vigorously in response.

"What are you dressed as? And who do we have here with you?"

"I'm Rick! This is my friend, Mr. Meeseeks. You've seen it, right? Everyone has! From the Rick and Morty show!"

Meeseeks waved at the MILF dressed like a slutty nurse as she stood holding the front door of her fancy house.

"Never heard of it," the woman twice his age sighed, still standing warily in the doorway.

"So, trick or treat?" Matt asked again with amusement in his voice.

The #1 MILF rolled her eyes and waved them in, put the tray outside, and scrawled a hasty message on her chalkboard to put on the porch next to it. The sign said, 'Please help yourself to just one candy. Back in a few!'

"You don't have two hours tonight," she said snidely to the kid dressed as Rick. "You know that, right?"

"We'll be out of your hair in no time, Mrs. Burton," Matt offered pleasantly. "Great costume choice, by the way."

"Thanks," she replied smugly. "People seem to really like it."

"Especially the dads! You should have heard them talking as they walked up the street."

"I bet they were, Matt."

"Anyway, I'm dying to see the ones you didn't pick!"

"What?"

"Your other costumes. I bet you had some other choices. I want to see."

She sighed, "OK, but what about him?" She pointed to Meeseeks, who remained utterly silent.

"He wants to see too!"

Nic ran through her options in her head and found them limited.

"OK," she sighed, "they're upstairs in my room."

She turned, and Rick and Morty followed her toward the stairs.

As she walked, she knew the back of the nurse's dress was undoubtedly riding up, and her ass cheeks were beginning to peek out below the hem. When she started to climb the steps, Rick and Meeseeks had a clear view of those succulent cheeks and her tight pussy lips.

"Do you ever wear underwear?" Matt asked, laughing.

She continued wagging her hips confidently as she climbed the steps. She knew she was providing a show, and the boys were undoubtedly thrilled, but it was what it was. There wasn't any way to avoid it with them following her.

"I hate underwear lines."

"So, you'd rather people saw your pussy?" he laughed.

"People don't see my pussy most of the time, you idiot! They aren't following me up the steps in an outfit like this!" she snapped.

She led them to her room, walked into her closet, grabbed a few of her other costumes, and tossed them on the king-sized bed.

"Ok, ok. Cop. Angel. Wonder Woman. That's it?"

She shook her head and grabbed the others, tossing everything she'd found on the bed.

Matt walked over excitedly and stood next to her to check them out.

"I bet Harley is fun on you! Oh, and what about this one?" He held up the schoolgirl skirt. "Try this on!"

Nicci looked skeptically at the two teenage characters in their silly costumes.

"Who is this guy?" she again asked, pointing at his friend.

"Mr. Meeseeks!"

Whomever it was in the Meeseeks costume waved goofily again.

"No, who is this guy REALLY!"

"He's my best friend!"

Nicci shook her head and crossed her arms. "What's he doing HERE, though, Matt?"

Matt smiled, and his face reddened under his mask, but he didn't have a ready response. Wasn't it obvious what he was doing there? Matt was surprised. He hadn't expected Mrs. Burton to react this way.

"Just to be clear, I'm not sucking your friend's dick or whatever bullshit you two perverts had in mind. I mean, I don't even KNOW him."

"So what?"

"So what, what? So what I'm not sucking some kid's dick I don't even know? Well, I'm not! THAT is...SO not part of the deal!"

"The deal is 'whatever I want' for two hours."

"Yeah, don't remind me. It's whatever YOU want, though, not anybody else. And I'm already regretting that too!"

"But if I want you to suck his dick, Mrs. Burton...," Matt grinned under his mask. He knew he had her but wasn't willing to push it further.

"You know damn well that's not what we had in mind when we made the deal, you pushy little shit!"

Rick/Matt held up his hands in a gesture of helplessness. He was standing right next to her, and he loved it. "Maybe it's not what YOU had in mind," he chuckled.

"Well....," she felt like an idiot for not making sure the contract language was tighter before she signed it, and as a result, she had no idea what else to say to counter the relentless boy.

Finally, she sputtered, "Whatever! It's not happening."

Nicci closed her eyes tightly in annoyance before reaching down to the hem of her nurse dress and peeling it slowly up her breathtaking curves. 'Fuck,' she thought, 'it's just easier to go along with things than to engage in a back-and-forth with this little clown.'

Her large breasts popped loose with a heavy, bouncy flop as the stretchy fabric passed over them. Matt was dying to touch them the second he saw them uncovered.

Then she got stuck, her head and arms completely covered with the white nurse dress. Both boys were transfixed and thrilled as she struggled to get the tight costume over her head. She stood stark naked in front of them for a few seconds, dancing, contorting, and complaining in an unintentionally provocative show. She jiggled, bounced, shook, and complained until she finally worked the thick cotton over her head.

"Thanks for your help!" she snarked sarcastically, throwing the outfit onto the bed. She picked up the plaid skirt and found it a piece of cake to button around her hips. By comparison, the schoolgirl outfit was easy. In a moment, she stood in her tiny, see-through, collared crop shirt, silly baby tie, and the plaid skirt that covered maybe half her fabulous ass.

Without being asked, she padded her bare feet over to her closet with the boys' eyes glued to her half-exposed ass. She bent seductively but without seductive intent and slipped each pretty foot into a pair of three-inch black stilettos while they stared.

She then turned to face them in the complete outfit, held out her hands, and cocked her head, waiting for the appraisal she knew was coming.

"Oh, my God, this is way sluttier than the nurse outfit!" Matt exclaimed giddily. "I told you to wear your sluttiest costume. Why didn't you wear this from the jump?"

"I obviously couldn't answer my door and hand out candy in this!" she hissed.

"But you're supposed to do whatever I want, and I wanted you in your sluttiest outfit. That's the contract! I know you agree with that part, at least."

Knowing he was right, Nic sighed and stood before her walk-in closet, sensing both guys gawking at her under their masks. They'd each had a tent in their cheap polyester costume pants from the time she'd seen the pair at her door, but the tents had grown in prominence as they awkwardly stared at her in the schoolgirl outfit.

Matt swallowed hard. "Turn around," he croaked.

"Excuse me?"

"Please turn around, Mrs. Burton."

"That's better."

She turned slowly and stood with her feet about 12 inches apart and smiled smugly, knowing exactly where their attention would be focused. They feasted their eyes on her fabulous backside.

Matt was overcome with lust. He had never seen her in heels, and wearing them made her legs look sexier and more stunning than ever. The pleats of her tiny, plaid skirt were stretched deliciously around the broadest part of her hips, and very little of her rear was covered.

She heard both boys groaning. Maybe five inches of the fattest part of her whole ass was sticking out of the skirt, and the two kids were hurting badly for her. She enjoyed their pain for a few seconds.

"I'd say 'take a picture. It'll last longer.' But that's kind of the whole problem, isn't it? The whole reason why I'm doing this."

Matt swallowed hard. Her ass made him dizzy. And those legs.... It seemed impossible, but those high heels only made the number one MILF's ass and legs look even more perfect.

Nicci shook her head and suppressed a grin. If it hadn't been so invasive to have them right there in her bedroom, it would have been comical. These two little monkeys were just so smitten with her. How long had they been just staring? And how long would they keep doing it?

"So, listen, this gawking totally works for me," she said. "We can do this the whole time. But you have like ten minutes before I need you out of here, and I know that's short of your two hours, and I am so deadly serious about you being gone."

Grateful for the prompt, Matt grunted and tugged on his erection tentpole. She was right. He might have just stared at her for the whole ten minutes in a trance if she hadn't said something.

He cleared his throat to sound more confident. "Can you climb onto the bed?" he asked.

With her heels clacking on the hardwood floor, Nicci sashayed past them toward her neatly made king-size bed. It was adorned beautifully with a dozen decorative pillows.

She climbed catlike onto the bed, letting her ankles and stilettos dangle off the edge of the mattress as she waited on her hands and knees atop the comforter. She felt the stupid plaid skirt rolling further above her cheeks, almost to her waist, just because of her position and the width of her hips.

She heard the boys groan loudly again and giggled. A position like this wasn't leaving much to their imagination, and she expected Matt's eager hands on her hips any second. 'Oh well,' she thought, 'at least I'm naturally wet. This should be pretty quick and easy.'

There was some quick shuffling and fumbling behind her, and she felt the obsessed teenager pushing his rock-like hard-on clumsily into her pussy lips even before his hands were on her hips.

To help things go more smoothly, Nicci reached back and used her slender fingers to part the lips of her vulva and create a perfect entryway to her warm folds.

Matt was glad for the assistance and hurried his cock into the MILF balls deep. Her pussy felt like velvet, and he was ecstatic to be inside her. He'd only been in her pussy once before, and it was even better than he remembered! His hands caressed her thick, fleshy ass, parked flawlessly in front of him, and he began pumping slowly. She giggled at his obvious desire to make it last and slammed her big butt back into his belly four quick times.

CasualK9
CasualK9
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