Milf Tails: Sweet Revenge

"You boys both have bright futures and have proud moms." Lori assured them.

"Going to be just like my dad," Josh nodded.

"Hopefully not just like him," Lori muttered, and when she smiled at Bret it seemed forced. "Going to be a good night for you, I can feel it."

"Thanks Mrs. Matthews," he responded as she walked away from him heading out of the room I think it will too."

She gave him a wave over her shoulder, but his eyes were on the backs of her legs. The shorts showed about as much as he'd ever seen from her. Even in the summer when Bret would come over to go swimming in their pool, she never came out in a bathing suit, or even a tank top, just t's and shorts.

Lori had some height to her, standing only a few inches under his 6'1, and her legs were long. They weren't slender but looked damn good. For that matter, she had a little to her hips, and between that and the apparent size of her chest, he always imagined her ass would have some meat to it, and her thighs on the soft fleshy side.

Bret had no issue with a little curve. Real women had curves, and knew how to use everything they had, girls his age were still finding their way, an older woman had been fucking for as long as he'd been alive and...

"Take a picture, it lasts longer." Josh punched him in the arm.

"Huh"

"Please, dude, you been staring at my mother since the first time you ever came over here."

"Sorry," Bret gave him a sheepish grin. "Didn't mean to be obvious."

"No big deal, I've checked your mom out a few times," Josh admitted. "We're guys, we can't help it."

"Guess not."

"I don't get it though, I mean, I know my mom's pretty, but she's not like super hot, and she dresses frumpy."

"What's frumpy?"

"I guess kind of unflattering, I heard my dad tell her she dresses frumpy and like an old lady."

"I think that's what I like about women like her, they look good without trying and they're not putting themselves out there like it's a free lunch sign,"

"Whatever, just control yourself, you looked like you needed a cigarette when she was tying your damn tie."

"Hope she didn't notice."

"I doubt it, you're a kid to her, she's not thinking you'd be checking her out." He laughed. "Especially in that damn shirt. My dad says she needs a GPS to find her in those clothes."

"Seems like she's not happy with your father," Bret glanced at his watch, "I have to get going."

"Yeah," Josh followed Bret as he headed for the front door. "They've been on the outs lately."

"Sorry to hear that," Bret walked out onto the porch. "What do you think is wrong?"

"I don't know, but the last few months my father's been making a lot of cracks about how she dresses, doesn't care what she looks like and acts like an old lady."

"What's he want her to do, dress like she's our age?"

"I don't know, but Mom keeps coming back with his job going to his head and sorry she's not a young trophy wife with fake tits like all his asshole partners have. Told him to grow up and get over his midlife crises."

"It'll blow over," Bret assured him. "Couples go through things like this."

"Wow, you already have that bartender philosopher shit down, don't you?" Josh laughed.

"Yeah, I guess so," he grinned. "Didn't even realize I was doing it."

"Well, go do it and make some money. Maybe if you decide to take a damn day off we can hang out."

"Yes," Bret nodded while making his way towards his car. "Promise, I could use some fun."

"Then come to Rich's party next Friday, his folks are away and there's going to be a lot of girls there. You can dress like that, and they'll swoon."

"Jealousy is a bad thing, Josh." Bret smirked while he opened the car door.

"Maybe you can get one of them to wear baggy clothes and pretend to be my mom. Goddamn perv." Josh winked to show he was joking with him.

"Thanks for the invite," Bret slid into the car and started it. "And the idea! Going to buy a Bruins shirt and bring it to the party."

He shut the door and backed out of the driveway as Josh laughed and slapped the hood of his car as a goodbye. As Bret pulled into the street, he wondered if Josh would think it was funny if he knew Bret had imagined his mother on more than one occasion when having sex with his former girlfriends.

It was kind of sleazy, and he'd felt guilty about it, but he hadn't planned it, it had just happened in the heat of the moment. Guess He couldn't do the right thing all the time.

Chapter Four

"Thank you, sir," Bret beamed as the man he'd just handed to Martinis to, slid a five dollar bill over to him.

"Keep making them like this, and you'll do just fine," the man's wife declared as she took a sip. "Perfect!"

"I'm here to please," he declared as he plucked a couple of empty glasses from the bar with one hand and gave the top of it a quick wipe with a towel.

"Is that so?" A woman with long dark hair and a snug fitting green dress sitting to his left asked. "I'll keep that in mind."

She gave him a sultry smile that caused his heart to skip a beat but didn't stop him from returning the smile. "Please do."

"And he says please," her dark eyes locked onto his. "I do like a boy with manners."

She raised her glass, toasting him, before she brought it to her red lips.

Bret's smile wavered when he saw the silver ring on her finger.

Married. Hot as she was, his father had told him when he'd started dating that if it wasn't yours don't touch it. No sex was worth having a mad dog husband of boyfriend come looking for you.

He'd gone to say some women fooled around, then deliberately let the husband find out so they'd be angry and jealous. He didn't need any drama and was relieved when a man at the corner of the bar, waved at him and pointed to his empty glass.

"I got you, sir!" he picked up a bottle of Jack Daniels, pouring it into the glass while he squirted some coke into it. He gave a deliberate pause, then dropped a little more JD into the glass, making it stronger.

He slipped a piece of lime into it, added a stirrer, and brought it over.

"See what you did there," the man handed him a twenty, "Keep the change because I'm liking what I see."

An $11 dollar tip! By his count he was up to a hundred and twenty dollars and it was only 9!

"They treating you okay?" Jill, the bartender handling the other end, asked as she came over to grab a new bottle of Cuervo from the shelf.

"Hell, yeah! This is more than I get in two nights at Gabe's."

"Surprised you get that much at that place." She paused to adjust her red bow tie, and he couldn't help noticing the way her white blouse stretched tightly across her ample chest.

He could make out her black lace bra beneath it. Bret wasn't a fashionista, but knew a woman only wore black under white when she wanted it to be noticed.

"I'm over two hundred already," she winked.

"You have more to work with." He pointed out, and she grinned.

"I do, that and men are hornier." She angled her head towards the woman in the green dress. "Not my business, but watch out for Mari, she's way more trouble than she's worth."

"Kind of picked up on that, but thanks."

Bret had to hand it to his father, he gave some damn solid advice.

"Hey, Bret!"

He turned to see Frank, the head of the wait staff, coming over to the bar.

"Yes sir?"

"No need for sir," he waved him off. "Frank's fine. Listen, Julia's working the small bar in the dining area, and she needs to go on break. Can you cover there for a half hour?"

"Absolutely!" Bret hurried around to the end of the bar, let himself out of the small gate and with a wave, made his way into the dining area.

He spotted the bar, which was half of the size of the one he'd been working at and came over.

"Hi, I'm Bret, I'm coming over so you can take break."

"Thanks sweetie!" The tall blonde swung the gate open for him. "I'll be back in soon."

"Take your time."

Bret went to the center of the bar and with no customers, sprayed it down and gave it a quick wash, then pulled the glasses out of the small dishwasher under the bar, and hung them carefully on the overhead rack.

A man came over and ordered two Cranberry and Vodka and left him a $10 tip. Goddamn, he had to find a way to get a gig here. He could make so much more money to help Mom, and himself.

He leaned against the back counter, idly surveying the crowd as they ate and chatted around the large round tables. His eyes wandered over to the small tables for two on his right, and just like that the night took a turn, a wrong turn.

Sitting a couple dozen feet away was Josh's father, Tom, and sitting across from him, her hand over his was a slender redhaired girl that couldn't be much older than Bret, if she were even that old.

"Holy shit," he whispered as he watched her tease a long red tipped finger over Tom's hand.

He wore an expensive charcoal gray suit and black tie, his dark salt and pepper hair slicked back, and smiling away as he talked to the young girl. Not that the way she was touching Tom's hand, or the way he was looking at her wasn't enough to tell Bret what this was, her outfit did.

The neckline of the girl's tight black dress plunged down between her breasts, revealing an uncomfortable amount of cleavage. The dress was short to the point he could see her entire upper thigh from his vantage point, and her long legs ended in a pair of heels that featured straps winding up to behind her knee and looked like something a stripper would wear.

She laughed at something he said, then when he continued, she pushed her hot pink lips into a pout, and batted her long lashes at him. Tom sighed and his expression looked as if he were giving in to something. He reached into his suit and produced an envelope.

The girl took it and after sliding out what looked like two tickets, she smiled and gave him a lascivious flick of her tongue.

"Oh, this is bad," he mumbled. Josh had told him his father was going away to a conference in LA next week. Why did he have the bad feeling he'd just showed her plane tickets?

What the hell was he supposed to do? Call Josh? Lori? Not say anything?

Things became much worse when Tom rose from his seat, and after walking around the table to give his barely legal looking friend a kiss, turned and made his way towards the bathroom.

Turnaround, duck, but those options vanished when one of the waiters came up to the bar and said he needed two seven & sevens.

"Gotcha," Bret hurriedly turned to put his back to the bar and made the drinks.

His hands shook as he grabbed the bottle of Seagrams and fished in the small fridge for a can of 7-Up, he made the drinks quickly, figuring Tom had passed him by now and wanting to be able to watch for his return.

He turned and put the drinks in front of the waiter and his stomach sank.

Tom was now standing at the bar.

"Hey, Bret, since when do you work here?" He slid into the stool directly in front of him.

"H...hey Mr. Matthews, I don't, I'm just filling in."

"Didn't see you when we were seated."

"I was on the other side; I'm covering for Julia."

"Timing is everything I suppose." Tom grunted. "Okay, kid, I'm not going to dodge the issue here. You saw who I'm with."

"Who is she?"

"Her name doesn't matter. Let's just call her stress relief."

"She's really young."

"I have a lot of stress," Tom began to smile, but it faded when he saw Bret wasn't amused. "Don't judge, Bret. You have no idea what it's like."

"Like as in married to a beautiful woman and having a great career and a good son? That kind of stress?"

"Touché' Bret, you have some balls on you. But here's the thing son. I know you think you're a man, and know how things work, but you really don't."

"I'm not your son," Bret replied with an edge. "But she could be your daughter."

"Ouch," Tom winched.

"I know how marriage works," Bret continued. "Two people fall in love and spend the rest of their life together; they don't cheat on each other."

"There's a saying my father taught me," Tom didn't seem affected by Bret's words. "If you're not an idealist at 20 you don't have a heart. If you're not a realist at 40 you don't have a brain."

"Maybe you don't have a heart. How's Josh going to feel knowing what you're doing to his mother?"

"Let's not be hasty, Bret." Tom put his hand up and spoke softly. "How about we talk for a couple minutes, a little man to man."

"Hold on," Bret nodded towards the waitress who had come over. "What can I get you."

"A C&C and an Appletini."

Bret made the drinks, noting his hands were still trembling. He was sick to his stomach, and had no idea what Tom wanted to talk about, other than he didn't want him to say anything, but how could he not?

He passed the drinks to the waitress who gave him a friendly smile and appraising glance before she walked away.

"She's into you, kid," Tom sighed. "Man, to feel your age again."

"Looks like you're feeling my age over there."

"You're quick, Bret, sharp tongue on you, must come from your mom. Your dad was a mellow guy."

"Don't talk about my dad, or my mom." Bret folded his arms over his chest. He found he was getting angry.

Such an amazing night right into the shitter as he was confronted with some hardcore real-life shit.

"Bret, I know what you see. I make great money, I have a nice house, my wife is a good woman, and I'm damn proud of Josh."

"Then why this shit?" Bret gestured towards the girl who had spotted them and alternated between looking at them, then playing with her phone. "That jailbait worth your marriage?"

"Be nice, you don't know her. She's a smart girl, she uses what she has to get nice things and have some fun," he shrugged. "Sure, she has some daddy issues, and can be kind of whiny, but..."

He stopped and nodded.

"Okay, let's get down to it. Sometimes, Bret, a man just needs to sink into some new flesh. Young flesh, exciting flesh. Flesh that doesn't nag or talk about her job, and never says they're not in the mood.

"Lori was so fine when we met and a goddamn wild cat between the sheets. She still could be, but in her mind, she's a mom first, and a career woman second, and I come in last. Look at her, she dresses like she's ashamed of her body, and I don't know, maybe she is, she has put on a few pounds the last couple years."

God, what a d-bag! Bret was so taken aback by Tom's bullshit; he had no immediate response. Taking his silence to mean Bret was listening, he went on.

"Hair's either pulled up like a preacher's wife, or a goddamn mess, getting a few wrinkles. Doesn't even care she's going gray."

"So? She looks her age," Bret pointed. "I'm going to ask Julia if she's carding your friend, because I don't think she's 21."

"Don't try to be a hard ass, kid, I'm being nice because you're Josh's friend." Tom scowled.

"And you're wrong."

"Maybe you should be in prelaw with my kid." Tom muttered. "But like I was saying, we're not old, Bret. We are to you, but I have plenty of fun left in me, and speaking of fun? Lori's about as exciting these days as sticking your dick in a jar of Vaseline."

"Whatever," Bret held his ground. "Sex isn't everything and if she were that bad, just get a divorce, why cheat?"

"Never heard of having your cake and eating it to? I deal with big time clients and they're either family value types or party hounds. The family types, Lori is a good mom, with a respectable job and looks good on my arm when she knows we need to impress.

"For the younger guys or the players? Girls like my friend over there are what they understand. Armani suits, expensive taste, and a hot little sugar baby on the side."

"Its not the right thing to do," he insisted.

"Bret, there's right in general and right for the individual. This is right for me, and my business is my business, not yours."

"Josh is my friend, and your wife has always been good to me." He tapped the tie. "Yours by the way."

"Looks good on you, keep it." Tom waved a hand at him. "But let's talk about Josh and Lori. Ignorance is bliss. Josh is smart, he knows me and his mother aren't getting along, but we're together and that's all that matters."

"They find out, Josh is heartbroken, we get divorced, he has to choose who to live with, his head gets all messed up, his grades slip. Ignorance is bliss, kid."

"They should know," Bret said, but less confidently than before. Tom had a point it would cause a lot of drama and was it really his place to say anything.

"Yeah," Tom proved himself to be the exceptional attorney he was, reading his face. "You're thinking about it and see my point. That's good, Bret, you always have to see both sides."

"Now, tell you what." He reached into his suit. "I know it's been tough on your mom financially since your dad passed. She makes good money at the hospital, but a lot of medical bills due, regular expenses, you're in school.

"That's why I'm working so much to help her out."

"Now that's the right thing to do," Tom gave him a pat on his forearm. "Good man there. What I'm getting at is money's tight and here you are working hard, and I'm taking up your time."

He pulled out a money clip and counted out five hundred dollar bills. "Here, put this towards school or give it to your mom."

"And if I take this it means I don't rat you out."

"It means you're using discretion and realism over being naïve and thinking life is always perfect."

Bret stared at the money. It could be a big help this month.

"Like they say on the game shows, but wait, there's more!" Tom smiled, the smooth perfect smile of a lawyer, all teeth, and no sincerity. "I'm tight with Ronnie and Kate, the owners. How about before I leave, I grab their ear and suggest they find room for a young man who's working through school and helping his widowed mom?"

"You could do that?"

"I can, all you have to do is just look the other way, Bret." He put his hand out. "Think you kids call it the bro code, we just call it tend to your own house and no one else's."

Tom slid off the bar when a waiter came over and asked for four bottles of Sam Adams.

"I'll go with my gut you'll do the right thing." Tom spoke as Bret pulled the beers from under the counter and popped the tops off. "I'll talk to the owners before I leave."

"Thanks man," the waiter left with the beers on his tray, and Bret returned his attention to the money on the bar and Tom still speaking.

"But if for some reason you get all moral and ratfink on me? You won't have a job at all, and I know people on Kent hospital's board of directors, could be time to wonder why they're giving your mother so much overtime, and straining her shift's budget."

He smiled again, this one the cold closing argument version.

"As an aside, I wouldn't be surprised if Josh didn't end up hating you for opening your big mouth and turning his life upside down to be a goody two shoes. Especially after I fill his head with that."

He tapped the bar with two fingers. "You take care, Bret, and think about what you gain or lose here."

He walked away, and Bret picked up the money before the waitress coming over saw it. He made the drinks she asked for as his mind raced. More than the money he'd slipped in his pocket, but getting a gig here?

How much could he make in four or five shifts? Less hours, way more money and a lot of high roller types, good people to get to know if you could. He could better his and mom's situation and avoid putting Josh and Lori through a lot of hell.

But the money and the job were to shut up and turn a blind eye to people he cared about being hurt. Blood money was kind of dramatic, but he felt that's what it was. On the other hand, the truth would hurt them, and maybe more in a way.

Was it his place to make that decision? For all his talk he was still a kid in many ways. He supposed he could go to his mother, but he didn't want to involve her, she had enough to worry about.