📚 don't mess with the help Part 1 of 2
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LOVING WIVES

Dont Mess With The Help Pt 01

Dont Mess With The Help Pt 01

by ryantyler98
19 min read
4.26 (22200 views)
adultfiction

This is written for my friend, Anthony.

Author's note -- If you've read a couple of my other stories, you may recall that I worked part time as a waiter on Long Island in an Italian restaurant during my years as an undergrad. My very best friend was another waiter by the name of Anthony. He was 18 or 19 at the time this happened. Karma will bite you in the ass, my friends!

It was a typically busy Saturday night at the restaurant. I was a server at P_____________'s on Long Island for a couple of years on and off during my undergrad years and enjoyed the comradery of my fellow waiters and bus staff as well as the kitchen. The restaurant was family-owned Italian cuisine and while it was small, it was fairly upscale.

I had been there for about a year when Aldo hired Anthony. He was a tall, somewhat shy, Italian boy, who was the cousin of someone in the family back in Naples and migrated to the United States right after school ended.

Anthony was put under my wing to learn the ropes. His English was good, but he was unaccustomed to dealing with New Yorkers and became the brunt of jokes by the local patrons who loved to tease him because he was so formal and polite to everyone.

Physically, he was about 6'1, just a hair shorter than me, but he was leaner with a shock of very black hair that sat like a mop on his head and a five o'clock shadow that made him look a little wild and unkempt. The women who worked at the restaurant loved to mother him and the MILFS and wives that came to dinner with their husbands loved to check him out when the husbands weren't looking. He was "cute" and sexy at the same time and reminded us of a wild horse -- the Italian word for wild horse was Cavallo selvaggio, so we gave him the nickname of Cav. But his looks weren't the only reason for his name. Anthony was "blessed" in other ways -- the first time one of the guys saw his endowment in the men's room, they kidded him relentlessly about his size and called him Horse cock, so the "Cav" stuck.

There were certain couples that we considered regulars and loved serving them. They were pleasant and tipped well and the servers and waitstaff established a rapport with them over time. Because the restaurant was close to a country club in Nassau County, we would get a lot of ladies in their white tennis outfits who would stop in for midafternoon drinks with their girlfriends. To me, there was nothing sexier than short skirts and tight little tops and I had my share of friends who would tease me.

But as much as they loved flirting with me, they absolutely adored Cav and would ask for him to serve them -- by the third or fourth cocktail, they were openly checking him out and would call over to the bar and say, "Anthony, please bring us another round, darling!" When he brought their drinks, they would make lewd comments to one another about his tight little ass and how they'd love to bring him home. It was all good fun.

Everything changed one Saturday evening when a new couple came in for dinner. The reservation was under Anderson, but it might as well have been Asshole. The husband looked to be in his early forties, with thinning hair, a belly and an attitude that just reeked of contempt. His wife was younger, slender and absolutely gorgeous. We guessed that she was about thirty, with blonde highlights, a tight little body and smallish breasts. As soon as they walked in that first night, we turned to one another and said, "Trophy wife".

Cav was their server that night.

After they were seated, he worked his way over to their table, squatted down to eye level and introduced himself.

"Good evening. My name is Anthony and I have the pleasure of serving you tonight. May I start you with a glass of wine or cocktail while you look over the menu?"

The woman looked at him and beamed. The husband scowled.

She said, "Hello Anthony...thank you. This is our first time here so open to suggestions?"

The husband rolled his eyes at his wife's friendliness, turned to Cav and said, "Whiskey neat -- Jamison -- tall."

Cav nodded and then shift to the woman and waited. Her blue eyes shone, and her smile lit up the room. While he tried to maintain some semblance of decorum and respect, he felt his cock harden a little. She was wearing a fitted dress that matched her eye color -- it was conservative but short and showed off her tanned legs a little.

Cav said, "And you, Miss? A cocktail or perhaps a glass of wine?"

Hearing "Miss" made her smile, but she looked quickly over to her husband to make sure he wasn't upset by the idea that they might not be married. But he was looking over the menu and if he heard, he didn't say anything.

"I'll have a glass of Merlot please, Anthony... Thank you so very much!"

Cav smiled at her, nodded and said he'd give them a few minutes to look over everything and would be back to tell them about the specials.

I was standing over by the kitchen when he walked by to go to the bar and I whispered to him, "She's stunning -- beauty and the beast...Cav grinned but said nothing.

Once the bartender made the drinks, Cav looked over at the couple and saw the wife looking at him and smiling. The husband was looking at his phone but glanced over to her and then followed her gaze to see what she was looking at. When he spied Cav, he snapped at her, and she looked away and then down.

Cav brought the drinks over to the table and placed the merlot down first.

"For you, Miss..." he said.

He placed the whiskey down in front of the husband and said, "For you, sir."

The husband scowled at Cav but said nothing. Cav asked if they had any questions about the menu and offered to tell them about the specials, but the husband cut him off in mid-sentence.

"I'll take the filet mignon -- medium rare -- tell the chef if it's wrong, it's coming back." He barked.

His words made her wince and she put her hand on top of his to settle him down. It was the wrong move. He pulled his hand out from under hers and threw his napkin down on the table, got up and walked away.

The wife smiled weakly at Cav and said, "Sorry about that, Anthony...my husband gets 'hangry' when he's between meals -- please don't take it personally."

Cav smile and said his dad was the same way and no worries.

"What can I get you, Miss?" he asked.

The blonde smiled and asked about the specials. She picked a scallop dish with vegetable medley of the specials and Cav nodded.

"Great choice...I've had it myself...it's quite tasty..." he said, reaching for the menus from her hand.

She gave him a little smile and a half wink and said, "Tasty is good..."

Cav picked up the little flirtation in her voice and grinned.

"Yes, it is...very appetizing..."

As he took the menus from her hand, his fingers touched hers lightly and she blushed a little. As he was walking away to put the order in, he glanced back at the table and caught her checking out his ass... He got hard immediately.

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Cav put the order into the kitchen and decided to go to the bathroom. Standing at the urinal, he heard the door to the bathroom open and immediately smelled cigarette smoke -- He turned and saw Mr. Anderson walk up to the stall next to him to pee.

Cav stared straight ahead but caught Anderson checking him out from his peripheral vision but said nothing.

As he finished, he shook off and tucked his cock back into his pants and went over to the sink to wash his hands. Anderson finished and took the sink next to him. He caught him looking at Cav in the mirror with a sour look on his face. Cav looked down at his hands and then up again. Anderson was still staring at him.

Anderson said, "Where are you from, kid?"

Cav bristled at the kid comment but said politely, "Originally from Naples -- I have family there but came to the United States a few years ago -- my parents' family owns this restaurant and thought it would be a good opportunity for me. I've been here almost 5 years now."

Anderson gave him a wicked grin and turned away from looking in the mirror to face him directly.

"Let me tell you something, kid...I don't know if it's common for you to flirt with another man's wife from where you're from, but it's not appreciated here. I'd complain to the owner about you if I thought it would do any good, but since you're family, I guess I'll just tell you. Knock it off..."

Cav started to say he had no idea what Anderson was talking about, but the husband dismissed him and walked out of the bathroom back to the table.

Cav shook his head and murmured, "Dickhead" under his breath, finished washing and walked out. He glanced over to the table and saw Anderson berating his wife. Cav heard him say -- "Why are you always checking out these young kids when we go out for dinner...do you want to be his mommy or something?"

The wife was red and shaking her head. Cav heard him tell her that he told me off and said to stop flirting with the customers. Her eyes got wide, and she looked like she was going to cry but then she got mad and said,

"He was NOT flirting with me, Michael! He was being professional and polite, which is more than I can say for you! I want you to apologize to him immediately!"

Anderson snorted and said he'd apologize when hell froze over.

They finished their drinks in silence and when the food was almost ready, Cav approached and asked if they would like another drink?

"What we would like is our food...can you make that happen?" Anderson whined at him in a shrill and condescending tone.

The wife looked at Cav, her eyes almost pleading with him to let it go. Cav nodded politely and said he would check on their food and offered them a refill on their drinks on the house for having to wait.

The husband nodded and Cav put the order into the bartender. When he came out of the kitchen, he brought over two more drinks and told them their food would be right out.

Almost in defiance, he turned and saw her openly looking at his ass again much to her husband's alarm. He started to say something and thought better of it.

Cav went into the kitchen and brought out their selections, placing them silently on the table, careful to avoid eye contact with either one of them.

When he put hers down, the wife touched his hand lightly and said, "Thank you, Anthony...this does look very appetizing!"

Cav looked up and she gave him a little grin. If Anderson noticed, he didn't say anything -- he was already grunting and cutting into his steak.

But without lifting his head from the plate, he said, "Eat your food, Ashley".

So her name was Ashley....Cav thought to himself...God, she was gorgeous.

Ashley gave him a little wink and touched his calf with her stocking clad foot lightly. And then started eating.

As Cav started walking away, he felt like the blood was rushing out of his head into his cock and was a little dizzy. It wasn't the first time a wife or girlfriend had flirted with him in the restaurant, but this woman was different...conservative, poised, classy...not slutty at all. Cav understood that part of her flirting was in defiant response to her husband's insistence that she not.

He came back to the table several times and caught her checking out his crotch on more than one occasion and then looked up in his eyes and smiled at him.

The rest of the evening was uneventful. He sensed some sexual tension every time he stopped by the table but couldn't determine if she was intentionally flirting with him to upset her husband or there was a genuine interest. Cav figured it would probably be best to play it cool.

As expected, Anderson left a measly tip at the end of the night, but meeting and quasi-flirting with Ashley made up for it.

When he got home, Cav laid in bed and thought about Ashley -- she was so much classier than the girls he was dating. The fact that she was mature and married was a fun taboo too. As he lay in bed, he thought about her dropping her shoe and running her foot against his calf and giving him a little wink and smile -- even if she was trying to get back at her husband, he wouldn't have seen that, so it made Cav wonder what her ulterior motive may have been. Surely a woman like her wouldn't actually be interested in a young guy like him? Or was she?

The more he thought about it, the more intrigued he was. He thought about her tight little body and was soon hard and began stroking his cock wondering if she would be interested in him -- how she was sexually, if she would give him a blowjob? He closed his eyes imaging it all and stroked faster and faster.

"Ugggghhhhhhh!!!!" his cock exploded, spraying hot cum all over his hand, chest and stomach...

When he stopped shaking, he turned and looked at the clock -- it was after midnight, and he had to get some sleep, so he was fresh for his other part time job in the morning.

He sighed to himself..." It sucks being poor," He thought.

The next morning, Cav got a shower and some breakfast -- He had to be at the country club no later than 10AM. He liked working there -- it was close to the restaurant, and he had a lot of different jobs, depending on where and when they needed him. The pay was just 'okay' but the job had its perks.

Today, he was working as a parking valet -- A lot of very sexy rich women would come to the club to play tennis and Cav LOVED the little white tennis outfits they wore. He always believed they were just miniskirts and was sad to learn they usually had shorts on underneath. What a rip-off! But he still got to see some great legs!

He changed into his uniform and got to the club right on time. The other parking attendant was pretty busy already, so he jumped in and started taking care of patrons. He loved helping them out of the car, getting the occasional smile or quick glance at amazing legs and ass and sometimes even a tip!

He was one of the few valets that knew how to drive stick shift and whenever a little sports car pulled up, they'd nudge him, and he'd rally over to assist. Some amazing Porsches, Audis and even a Maserati or two would fill their parking lot.

He had just parked a pretty sweet Lambo and had gotten back to the valet station when a black Mercedes with heavy tinted glass pulled up. He saw a petite figure behind the wheel in sunglasses dressed in white and walked up to the driver's side door to open it for them. As he reached for the door handle, the window slid down.

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It was ASHLEY from dinner the night before! She was in a Nike tennis outfit, looking at fit as any woman could be. She looked up at Cav but didn't make the connection at first.

"Excuse me, young man...we're new members of the club -- is there where I go for the tennis courts? Do I park here?"

Cav grinned.

"Yes, Mrs. Anderson, you're in the right place..." he said.

The woman looked shocked that he knew her name and took off her sunglasses to peer up at him.

"ANTHONY!" she cried, "What are you doing here?"

Cav smiled and told her that when you were a young poor immigrant, you needed at LEAST two jobs to make ends meet and that this was his second one.

Ashley cooed and touched his hand.

"Poor Anthony!" she said, "I had no idea! I thought being a professional server in a family restaurant made you a millionaire!"

Cav looked at her dumbfounded and then Ashley burst out laughing, which made him laugh as well.

He decided to play along...

"Yes, I'm secretly EXTREMELY wealthy and just pretend to be poor so I can meet hot women in tennis outfits!"

Ashley laughed and said, "I'll let you in on a little secret...Mr. Anderson and I are nouveau rich. At least I am. I grew up in a very poor family and was one of seven kids. I didn't own a tennis racket let alone a $200 tennis outfit until we married."

Cav grinned at her and said, "Well, it's money worth spent, Mrs. Anderson. It looks amazing on you!"

Ashley grinned at him and said, "Anthony, you're so sweet! Does it look okay?" As she was talking to him, she grabbed the hem of the tennis skirt and pulled it up, revealing the shorts underneath.

She said, "And how about this? They give us these sexy short little skirts to tease the men with and then rip you off with shorts underneath. That's a sin! Ha!"

Cav nodded his head and said, "I've been saying that for years...I never knew about the shorts and would always try to sneak a peak whenever I'd see a girl in tennis gear only to discover they have shorts underneath. Boy, do I feel stupid!"

They both laughed at that and then Ashley said, "Well, it rare, but depending on the designer, some tennis skirts don't have the shorts underneath -- maybe you'll get lucky someday!"

Then she said "I see I've got a line of cars backed up behind me...Maybe you better stop distracting me, Anthony and park this beast while I go for my lesson?"

Cav nodded and open the door for her. She smiled and climbed out of the Mercedes, giving him a little view of her legs and upper thighs in the process.

"Thank you, kind sir...Here's a tip to keep your identify as a multimillionaire safe..."

She handed him a $20 and sauntered into the club. Cav watched her ass and those amazing legs as he walked away and then parked her car for her.

Later in the afternoon, he missed out on saying goodbye -- the other valet retrieved her car but gave him a message from "the blonde in in the Mercedes" that she hoped to see him again and that she had another lesson on Thursday.

Cav grinned and thanked his coworker for the news...So Ashley WAS a flirt...he would certainly have a lot to think about between now and then.

On Thursday, Cav made sure he was at the valet station early -- it was only by chance that he ran into Ashley that first time and he didn't really know anything about her schedule or anything else for that matter. He was in the middle of parking an SUV when he saw the black sedan coming up the road leading to the clubhouse and almost wrecked the one he was driving to get back in time to see her. He tried to play it cool and was nonchalant standing at the station when she pulled up. There was no one behind her, so he hoped he could spend a little time talking again.

Like before, she lowered the driver's side window.

"Good morning, Anthony...how are you on this fine Thursday?" she asked.

Cav grinned and looked into the cab of the Mercedes -- Ashley was wearing a different tennis outfit, this one was white with a pink inlay that came to about mid thigh and looked incredible on her.

He smiled and said, "Hello Mrs. Anderson -- here for your tennis lesson?"

She smiled and replied, "Indeed I am, Anthony.... how nice of you to remember!"

Cav smiled and said that he loved her outfit and how terrific it looked on her...

Ashley smiled and said, "Do you like it? It's new...It's a company called ExEat and it's called the Monte Carlo Tennis dress. Very comfortable!"

Cav leaned in a little to look at it...he touched the material of the shoulder and said, "It does look both comfortable and stylish!"

Ashley smiled warmly and said, "I'm glad you think so...it was obscenely expensive and the funny part is, you'd think for almost five hundred dollars, it would have included shorts!"

Hearing those words, Cav felt his cock swell and almost explode out of his uniform. He swallowed hard and tried to be cool, but as he tried to speak, he heard his voice crack -- his youth betrayed him...

"Oh? Really -- that IS unusual..." he tried to get out.

Ashley smiled confidently and reached down to touch the hem of the skirt and VERY slowly slid it up higher onto her legs. She was looking in his eyes as she moved the dress higher and saw his mouth drop open with eyes like saucers.

Ashley almost burst out laughing...She loved teasing the young man but knew he was about to explode, so she brought the skirt all the way up, exposing a very sheer, very transparent thong... A small wisp of blonde pubic hair tuff in a triangle under the thin material.

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