Milf Tails: Sweet Revenge

Author's Note: A few days ago, I published this story, but due to a glitch in the Lit matrix, the story was cut off before the final scene. Rather than wait for the truncated version to be removed then resubmit, I am publishing this one so it will get to you sooner. Sorry for the technical difficulties. LC68

Chapter One

"Hey, mom!" Brett greeted his mother with a wave as he slung his backpack on the couch.

"Hey, yourself," Mom looked up from her book. "Gabe called, he said he tried your cell, but it kept going to voice mail."

"Shit," Brett rolled his eyes as he plucked his phone from his pocket. "I forgot to turn it on after I got out of class. "Maybe he needs me to come in tonight."

"Brett, you've worked five out of the last six nights," Mom reminded him. "You need to get your rest and focus on school."

"Get my rest?" he laughed. "I'm 20, I don't need as much sleep as you old people."

"Watch it, mister," Mom cautioned him with a finger. "As long as you live here, I can ground your ass no matter how old you are."

"Yes ma'am," he lowered his head demurely, but couldn't keep the smirk off his face. "Whatever you say."

"Don't humor me," she sighed. "Seriously, Brett, I know you love the new job and I appreciate that you want to work and help out, but school's more important."

"My grades are good, Mom. I had a 3.8 last semester, remember?"

"You were working 20 hours a week at Starbucks, now you're working close to twice that and until one in the morning sometimes," she complained. "I still can't believe you can serve booze without being old enough to drink."

"RI has cool laws, what can I say?" Brett chuckled. "But no worries, I don't drink."

"Right, A 20 year old college student and you have a virgin liver," Mom shook her head. "I'm not naïve, now stop dodging my point."

"I get to sleep by two, and class is at nine. I get a few hours sleep, and I study when I get home before I go in."

"It's a lot, Brett. If Gabe wants you to work, tell him not tonight."

"Come on, Mom. I'm a grown ass man now, I know my limits."

"Oh, my god," she slapped her forehead for effect. "A grown ass man? Your limits? You're not grown ass when you still live with mommy."

"Ouch," Brett winced, then made her laugh when he raked the air with his fingers and meowed. "Bitchy!"

"Just say no."

"I have my car insurance due; I need a couple of books for my next classes, and the mortgage is coming up. I promised Dad when we knew it was near the end I'd always do the right thing as a son and a man. The right thing is helping my mom with the bills and paying my own way as much as I can."

"You know," Mom gave him a soft smile. "I take it back, maybe you're at least partially grown up."

"Thanks," he rolled his eyes.

"You're a good boy, Brett," Mom saw the look on his face. "Man, good man," she corrected herself. "A good young man should do the right thing but should be having some fun too. When was the last time you went on a date?"

"Melissa," he replied, looking away because he knew what was coming.

"You two broke up six months ago. That's too long for a good looking, grown ass man like yourself to be alone."

"I'm fine, work and school keep me busy," he grinned. "Girls can be more distracting than jobs, you know."

"They're more fun than jobs," Mom frowned. "If not, there's a problem."

"Right now, your single, well rested, studious, and partially grown ass man wants to make some extra money."

"I suppose there's worse things than wanting to be responsible," Mom conceded. "Especially these days, half the kids your age don't even work."

"Kids these days," Brett sighed dramatically as he turned his phone on.

"Besides, I'm sure serving drinks might put you in contact with some attractive young ladies, but I know that's not why you're eager to keep taking shifts, its all about the right thing."

Mom looked at him expectantly.

"Unfortunately, it is a hazard of the profession," Brett said in a somber tone. "And it is embarrassing the way they fawn over me, but I tell them, ladies, can't you see I'm working here, and my mom says I have to get my rest."

"You're killing me," Mom tried to look series, but burst out laughing. "Fine, smart ass, go to work, but promise me if it starts to get to be too much or your grades slip, you cut back?"

"Promise." He nodded as he turned away, already bringing up his voicemail.

"And you're not going in before dinner, you need to eat."

"Yup," he gave her a thumbs up over his shoulder.

"Hey, kiddo," Gabe's gruff voice sounded in his ear. "Lookin' to see if you want to pick up some extra money tonight, call me back, kay?"

Bret waited until he went upstairs and entered his room before calling him back.

"Took you long enough," Gabe answered. "For a kid who wants hours, your phones off all day."

"Hi to you too," Bret replied. "I have it off in school."

"Good thing you're out then because I was getting' ready to call Tammy and see if she wanted to work."

"I'll take the shift!"

"Don't know," Gabe grunted. "Tammy's better for business, she's got those big tits and wears those tight little tops."

"And screws up half the drinks," Bret responded.

"But she's pretty and has big tits." Gabe repeated.

"Fine. I'll wear a shirt two sizes to small and giggle, how's that?"

Gabe laughed in his ear, but the laugh turned into a jagged smoker's hack and Bret eased the phone from his ear. "Christ, kid, that was a good one." He snickered. "'Sides, you're kind of pretty anyway."

"Am not!" Bret exclaimed.

"Are too, mister goop in your hair."

"Whatever, what time."

"Oh, right, seven to two okay?"

"Two? You need me to help clean up or something?"

"Shit! I'm losing my damn mind these days. It's not here, it's at my buddy, Ron's place, the Capital Grill, that cool with you?"

"Hell yeah, I bet the tips are great."

"They are, but they have a dress code for the staff, you got a white dress shirt?"

"I do, and a pair of black suit pants I can wear with it."

"Ron said he has a vest for you, but you need a red tie."

"Red tie? Shit, I only have black and grey."

"Stop and buy one if you have to. Either that or I'll call Tammy, I'm sure one of the dirty old men she screws around with probably left one behind."

"You're a classy guy, Gabe," Bret muttered. "But I'll figure something out."

"Be there by 6:45. I vouched for you with Ron so do a good job and you might get to fill in there when he needs someone."

"Thanks, Gabe, you're the best!"

"Make me look bad," he went on as if Bret hadn't replied. "And you'll be looking for new job, got it?"

"I'll be lights out," Bret promised. "I'll do the right thing by you, Gabe. I always do the right thing."

"Just make the drinks right, kid."

Gabe ended the call and Bret saw it was 4:50. He hurried over to his window and opened the blinds enough to peer through them. He smiled when he looked across the street and didn't see the red minivan in the driveway.

So far today was all about winning as he hadn't missed his favorite guilty pleasures, checking out his long-time crush, and go to fantasy since he was old enough to have fantasies about women.

Lori Matthews, the hottest woman he'd ever laid eyes on.

Chapter Two

Bret stayed by the window feeling like a creepy stalker. The fact Lori happened to be his friend Tim's mom added guilt to the creep factor, but he couldn't help himself and figured what happened in his head stayed in his head.

His brief misgivings about his secret obsession fell away when, just like clockwork, her van appeared around the corner. Bret watched her approach playing the game with himself of wondering what she'd be wearing.

Lori often wore slacks and blouses to work, but once every few days Bret would strike perv gold and she'd have on a dress or a skirt. He'd been watching her come home whenever he could since the day he'd first seen her when they moved in seven years ago and had his personal favs.

She never wore anything inappropriate. Her skirts were typically knee length or slightly higher, but nothing risqué. Her blouses tended to be loose fitting as were her slacks.

The same for her shoes which were either flats, wedges or on the occasions she wore heels, not very high, functional rather than sexy. Her brown hair, long and curly when he'd see her around the house when he hung out with Josh, was generally pinned up, or pulled back, giving her a more professional look.

For some reason, the fact Lori didn't dress trashy or revealing made her more attractive to him, gave her an air of class and mystery. A mystery that Bret, in both his wildest dreams, and waking masturbation sessions, longed to solve.

The van pulled into the driveway and Bret did a silent drum roll when the door swung open. The hits kept coming for him when one blue heel, followed by a bare leg extended from the Van.

Lori stepped out, her navy-blue dress momentarily hiked up from sitting, and giving Bret a brief, but thrilling, look at the back of her leg up to her mid-thigh before she smoothed it out.

The dress fell to just above her knee and flared out, not giving him any type of view of her ass, but when she turned to the side to approach the house he saw the top did give him a decent shot of her breasts.

It wasn't that the dress was snug, but the fact Lori was big on top. Not that he'd ever seen her wear anything to fully display their size, but when they were prominent in loose fitting outfits they had to be impressive.

"Dammit, Lori," he whispered. "Can't you wear anything to give your stalker a little something to perv on?"

He watched her walk up the driveway, his eyes following the natural swing of her hips. She reached the house and went inside, ending Bret's pathetic thrill of the day. He turned away and opened his closet door looking for the white shirt and the slacks, hoping they didn't need ironing.

He thought about the tie, Target was on the way, they'd probably have one, but he had less than two hours to shower, get dressed, eat, hope the first place he checked had a tie, then fight rush hour traffic into downtown.

The Capital Grill was high end, and he could easily make a couple hundred in tips tonight, and if he did a good job, maybe get more chances or even a foot in the door for a job, so he couldn't be late.

Bret found the shirt and pants, dug out his one pair of black dress shoes and a decent belt. He laid everything out on the bed and looked up at the sound of a car door. He could see through the still open blinds just enough to make out Josh heading into his house.

Josh...Josh whose father was an attorney and had an entire closet of suits and ties in all colors and styles. He grabbed his phone.

"Whoa, man, you stalking me?" Josh answered. "I just got home."

Nah, I just stalk your mom, Bret thought. "Listen, I need a favor. I have a chance to do a shift at the Capital Grill tonight."

"Sweet! My dad goes there all the time with clients, lot of big shots, you'll make a killing."

"Hope so, but I just found out, and Gabe said I need a red tie. I don't have much time to shop, you think..."

"My dad has a couple," Josh headed him off. "Shit, he's even got a yellow one, you know how ugly a yellow tie is?"

"Think I could borrow it?"

"I don't see why not. He's working late though and probably in a meeting, then he's got a dinner with a client, hold on."

"Hey, Ma!" Bret heard him yelling away from the phone. "Bret needs a red tie for work tonight, can he come by in a little while and borrow one of Dads?"

"Of course! I'm heading upstairs to shower; I'll bring it back down with me."

"All set," Josh told him.

"I owe you, bro."

"Hey, that's what friends are for, right?"

"I'll see you in a half hour or so," Brett hung up, a smile spreading across his face.

Extra money, a chance to impress and maybe get more work, the tie problem solved, and best of all? He'd get to see Lori for a couple minutes. This was turning into one of the best days ever.

Chapter Three

Bret hopped out of his car, feeling stupid considering he lived across the street, but he figured he'd look dumber running from his house to theirs, then back again. He made his way up to the door, ringing the bell and glancing at the black Movado watch that had belonged to his father, if he were going to dress up, he may as well go all in.

He'd taken a quick power shower, run downstairs in a t-shirt and shorts to wolf down dinner so he wouldn't stain the only white shirt he owned, then changed. Bret generally didn't go out of his way to worry about his appearance but wanted to look sharp for the higher end customers.

Fortunately, he'd just gotten a haircut a couple of days ago, and his fade was looking fresh. He added some gel to his thick sandy brown hair, not only slicking it back, but bringing out the natural waves in it.

His beard had gotten a little thicker than he liked, but he'd been running around so much he never took the time to trim it.

Time wasn't as tight now that he didn't have to stop anywhere for a tie, so he trimmed it, cleaning it up as well thinning it out. He'd flashed a practiced 'what can I get for you, sir-ma'am' smile at his reflection, and had to admit, he thought he looked pretty good tonight.

Mom's comment about girls was spot on. The bartending gig gave him plenty of chances to meet and flirt with them. He did both every night, sometimes to work a tip, others in the hopes there was some real interest, but so far nothing had gone any farther than a little teasing banter.

In a way it wasn't a big deal, Mom was right more than he cared to admit, between school, studying, and working, he was burning it at both ends, and really didn't have time to date, but the idea of a quick hook up had its appeal. He hadn't gotten any since his last time with Missy and that was months ago.

No wonder he was reduced to getting a thrill out of seeing a few inches of leg from the Milf across the street. But there were more important things to worry about right now, like helping Mom pay the bills and keeping his grades up.

Those were the right things to do right now and the two things he'd promised his father. Bret left the house, telling his mother the necessary white lie that he'd be out of there before one, and backed Dad's Chevy Impala out of his driveway and into the foot of Josh's.

His winning streak continued when Lori answered.

"Hey, Mrs. Matthews," he greeted her. "Thank you for helping me out tonight."

"No worries," she stepped aside to let him in. "Wow, Bret, you look great!"

Even though it was a simple compliment with nothing behind it other than being nice, the words sent a thrill through him.

"You think I look okay?" Five seconds in front of her and he was already being a loser and fishing for some more attention from a married woman twice his age who also happened to be his best friend's mother.

Lori cupped her chin and made a show of looking him over.

"You're looking pretty fine, I bet you're going to get some good tips from the ladies tonight."

"Yeah?" He could feel himself grinning like an idiot, but even worse...

"You're blushing!" Lori clapped her hands. "Aww, aren't you cute!"

Great, he'd gone from fine to little boy cute. Meanwhile, in front of him Lori was as looking sexy as fuck. Well, to him anyway, in the sense she wore a pair of loose-fitting shorts and a baggy Bruins T-shirt, but still had his complete attention.

Her hair was down, something he didn't see often. Lori's hair was a mass of curls that surrounded her face, and partially covered the left side of it. It gave her a wild look that was a sharp contrast to her otherwise always proper look.

There were a few grays scattered through her otherwise brown hair, but for some reason that added to his attraction to her. Maybe it was the fact she embraced her age and didn't try to conceal it.

Bret had lost track of how many times he'd imagined that hair flowing down her bare back, or over her shoulder, the curls covering the tops of her breasts. Better yet, across his stomach and thighs while she went down on him, or tickling his chest while she was on top, leaning over and dangling her...

"Hey pretty boy, here's your tie."

He'd been so engrossed in his mini fantasy involving the sexual potential of Lori's hair, he hadn't heard or seen Josh come up next to him.

"Thanks," Bret took the tie, then rolled his eyes. "Crap, I have to stop back at home. I don't know how to tie a tie."

"I don't either," Josh shrugged. "I keep mine tied or my father does it."

"I'll do it." Lori took the tie from him and flipped it over his head.

The way this day was going he was going get massive tips and a job offer because everything was coming up Bret, right now! Lori reached up and slid the tie under his collar and chuckled when she had to fasten the top button.

"Haven't worn one of these in a while I take it?"

"Not since my dad's funeral."

"Honey, I'm so sorry," Lori frowned. "I feel so bad for you and your mom."

"Yeah, bro, that's tough," Josh smacked him on the arm. "But so are you guys, right?"

"I didn't mean it like that," he didn't want her sympathy, the comment had just come out without him thinking. "Just that was the last time."

"And someday you'll be wearing one when you get married," Lori told him as she lopped the tie. "Life is full of sad endings, but also happy new beginnings."

"I guess," Bret focused on her, rather than her words, as it was a lot cheerier than thinking about his father.

She was standing so close he could smell her strawberry scented shampoo and her breasts, visible even in the shirt that was so big on her, he wondered if it was her husbands, were inches from him.

He studied her face as her attention was on measuring the tie. Lori's brown eyes were soft and warm, inviting would be a good word for them. The same word could be used for her lips which even without lipstick were full and well defined.

There were a few small lines around her eyes, and when she smiled there were some at the corners of her mouth, the only sign of her age as otherwise her face was soft, and her features smooth.

Bret did notice there were some darker circles beneath them as if she hadn't been sleeping, but they did little to distract from her natural beauty. Many women looked amazing, but because they were made up, sexed up, and putting themselves out there.

Lori looked good without trying. Both her loose casual, and professional mode of dress showed just enough for him to suspect there was a hell of a body under there but left plenty of room for him to have to imagine it.

With her messy hair and a few laugh lines as his mom called them, she wasn't the flat out smoking beauty that some women, and most milf porn stars were, but that was fine with him. She was a real woman, the kind you saw every day, the kind you had an actual chance with, well, if there was a chance to be had.

"Too tight?" Lori tugged gently on the tie.

"Perfect, thank you," Bret nodded.

"I like that cologne, what is it?" Lori tugged once more on the tie, giving it a final adjustment, and stepped back.

"Wings by Giorgio."

"I don't know, Bret, fresh haircut, beard nice and neat, dressed for success, smell good. You might get some numbers with those tips." She sighed. "Youth, its wasted on the young."

"Jeez mom, lay off, his head's fat enough as it is." Josh rolled his eyes. "Hey, when do you think Dad's going to be home?"

"He didn't say, and I didn't ask," Lori's eyes hardened and there was an edge in her voice. "Why?"

"Sorry, just wondering, I needed some help with an essay on copyright law."

"Going to be a big shot lawyer like your dad?" Bret grinned. "Cool, I can borrow money from you whenever I need it."

"Because engineers don't get paid?" Josh asked.