Milf Mona's Vacation Nightmare

Disclaimer: This story and all characters are fiction. In real life, non-consensual sex of any kind is illegal and immoral, and not condoned by the author. All characters are over 18.

MILF MONA'S VACATION NIGHTMARE

Husband's new friends and old enemies blackmail busty mature wife

1. Paradise Point Resort

Despite his life being labeled as perfect by many of his friends, Brian Doyle felt like something was missing. He had a good sales job, two healthy, well-mannered teenage kids, a house in the suburbs, and of course, Mona. Brian's attraction to Mona, his sexy 36-year-old wife, had only grown over the years.

While Mona had the natural good looks that came with being a leggy 5'10, skinny, and physically active woman, her body type had changed as she became a mother. In particular, her bust had grown considerably after the birth of two children, and her skinny frame now supported a wonderfully large but still firm 34dd bust. Mona had also worked especially hard in in the gym to transform her "flat" butt into what could now be considered a "bubble" butt. She could certainly now be considered a voluptuous mom in every sense, and Brian couldn't get enough of it. It did not matter what she wore -- nearly every guy that crossed her path found it impossible not to stare at her Barbie-like proportions.

Brian found it hard to quench his insatiable desire for sex with his hot but still very conservative wife. Ever since he had known Mona, she had always been shy and tried her best not to attract any additional attention. Brian had bought her sexy outfits over the years and tried his best to convince her to wear them, in private and out in public, but rarely had any success.

Over time, Brian's fantasies evolved to thinking about her with other men who might have more success in stirring up her wild side, but he was too worried about her reaction to that idea to bring it up. Regardless of whether that ever came to fruition, Brian felt that they needed a vacation to rev up their relationship and love life, and he soon found what he thought was the perfect, romantic destination.

A few weeks later, with the kids shipped off to Grandma's house for the next 5 days, Brian and Mona Doyle jetted off to Cancun, Mexico. Brian was excited for many reasons, but seeing his big-titted wife strut around in a bikini for a few days topped the list.

After checking into their room, Brian and Mona headed down to the beach. Mona looked like the definition of a milf, her natural, voluptuous body on display in a bright pink bikini for every male onlooker who walked by.

One of those who took notice of Brian's beautiful wife was the owner of the beach resort, Tom Diggs, a balding, 52 year old man who stood 6'2 and had the physique of a former body builder. After making millions as an investment banker and watching his first marriage unravel because of his inability to spend enough time at home, Tom had decided that a change of scenery was what he needed. After many months of researching potential new business ventures, he had stumbled upon the Paradise Point resort in Cancun, which was in need of repair and a new owner. A few months later, he was the proud new owner of the resort and his spirits lifted as he envisioned a new beginning.

Over the five years since Tom had bought Paradise Point, he had built the resort into a premiere destination in Mexico, and he had become something of a local celebrity in Cancun. One of the other fruits of his success in building a highly rated resort was the tremendous number of attractive women who made their way to his hotel. With Tom's reputation and ability to woo women with simple yet effective gestures such as free room upgrades, complementary drinks and meals at their highly acclaimed restaurants and invitations to his 5,000 square foot luxurious villa, he found it easy to have affairs with both single and married women.

But Tom liked a good challenge, and married women, particularly those with their husbands close by, fit the bill. For his favorite targets, Tom would frequently offer to upgrade their accommodations, and he would place them in the Roosevelt or Edmond Suites, both of which were equipped with hidden cameras throughout each room. During his days in the cutthroat world of investment banking, he had enjoyed the many hours of prep time, analyzing a potential deal, concocting a plan, and then doing whatever it took to get it done. He viewed women in the same vein, and enjoyed getting a detailed glimpse of their bodies before he swooped in to claim his prize.

Tom had been on the beach prepping a few of the new bartenders at their new Tiki Bar when he caught a glimpse of Brian and his beautiful leggy wife, Mona. She was wearing a white mesh cover up over what looked like a pink bikini. Her skin tone was perfect, and her long flowing brunette hair was partially covered by a straw sun hat. Tom had a weakness for tall, natural looking women with curves -- his first wife had been a former model -- and he felt a tingling in his groin as he saw Mona strip off her mesh top to reveal a mouthwatering set of heavy firm tits to match her supple behind.

For the next hour, Tom found it hard to concentrate on educating his new crew as he tried to catch a glimpse of Mona. He had tried to focus elsewhere but nearly ejaculated in his pants when he saw the leggy beauty emerge from the water after losing her bikini top, clutching those wonderfully huge milky white jugs as they wobbled in her arms. He knew at that moment that he had to have this beauty, and he began to concoct a plan.

Brian and Mona had enjoyed their first day at the resort, and they were looking forward to dinner at one of the four star restaurants on the property when they heard a knock at the door. At the door was one of the hotel's assistant managers, Douglas, who said he had heard they were celebrating a wedding anniversary (Brian had specified this on the reservation in hopes of getting more perks), and wanted to offer the opportunity to upgrade them to the spacious Roosevelt suite. Brian and Mona smiled widely as they asked what they had done to deserve such a wonderful gift, to which Douglas replied, our hotel does whatever it can to make our guests feel special.

After Douglas had brought the excited couple to their new room, Tom heard him radio back down to the front desk that the room switch had now been completed. He had, of course, inquired about the name of the couple after he had spotted them at the pool, and instructed the hotel staff to come up with a reason to upgrade them. Tom could barely contain himself with excitement as his thoughts immediately focused upon the big-titted Mona, who he would hopefully get a glimpse of later that evening.

Tom stared up at his 65-inch screen surrounded by 10 smaller televisions with views of every room in the two suites. He was fully aware of the legal ramifications and likely jail time if word ever got out that he was filming his hotel guests. He went to tremendous lengths to hide his setup by hiring an external cleaning staff. They signed confidentiality agreements that stated they would be sued if they spoke of anything they saw during their time at Tom's residence; and they were never to enter Tom's "private screening" room.

Tom dialed down to the Three Pines Restaurant, where he had been told the Doyles were dining, and asked that two bottles of wine be sent to their table, with his compliments. Tom had hoped the free wine might lead to some additional sexual activity that he would get to enjoy on video later in the evening. When the bottles were delivered, Brian and Mona looked at each other in disbelief. Brian remarked how lucky they were to be staying at such a wonderful place and hoped to meet Tom to thank him in person.

Tom was in the middle of eating his dinner when one of his camera screens picked up the couple coming back to their suite. Tom's heart raced as he anticipated seeing Mona's hot body nude. After a few minutes of lingering on the couch, Mona made her way to the bedroom to get ready for bed. She slowly unbuttoned her shirt and Tom nearly ejaculated in his pants as she unhinged her bra clasp.

Tom's cock throbbed as he watched Mona rub lotion on her magnificent jugs. Her areolas were dark and wide as they covered at least a third of her boobs. Their natural shape was perky but had a slight sag and slowly swayed from side to side. She had stripped down to a pair of white thong panties, which gave Tom an even greater appreciation of her physique. While she had a few wrinkles on her backside, it was bubbly and muscular and looked ripe for a spanking.

Brian staggered into the room 15 minutes later and began to sloppily massage his wife's back and kiss her. It was clear he was drunk, and she was not. Hoping that he would get to enjoy some much anticipated sexual activity between the couple, Tom was disappointed when Mona appeared to rebuff Brian's advances as he made multiple attempts to take off her thong. Brian soon passed out on the bed as Mona made her way to the bathroom to shower off.

Tom's face pressed up against the screen as he watched Mona drop her thong and climb into the shower to scrub off her perfect milf body. Tom's penis swelled as he watched her lather up with soap, scrubbing every voluptuous curve and shaving the edges of her well-manicured landing strip. Tom imagined himself in there with her, pressed up against her big behind, reaching around to grab a hold of her mammoth breasts as she rubbed her bubble butt on his dick. After drying her hair, she changed into a silky nightgown that fit tightly against her curvy body. It was clear that this magnificent woman would not give in easily to sexual advances, even from her husband, so Tom would need something to loosen her up and spark her interests.

II. THE APPROACH

Brian woke up early the next morning to find his lovely wife nude from the waist down as her nightgown had ridden up during the night. She lay there peacefully with her perfectly manicured thin brown landing strip leading to her tightly puckered pussy lips. Even after two kids, Mona was incredibly tight and could rarely take Brian's average 6 inches without sufficient lube. Brian was overcome by the sexiness of his hot exposed wife. Before he could think about the consequences, he took his rock hard erection and tried to maneuver it into his wife's tight vagina. Immediately upon insertion, she jumped up and screamed in pain.

Mona punched Brian and yelled, "Don't ever pull something like that again Brian!"

She was furious and stormed into the bathroom. Emerging a while later, Mona declared she needed the day to herself to get over Brian's unwanted advances and he should go do something on his own. Brian explained that he was just sexually frustrated but she wouldn't have any of it. She said she would be in the main beach area today and it would be best if Brian found somewhere else to spend his time.

Eagerly watching from his television display, Tom had awoken to Mona's screaming and overheard everything that followed. He couldn't have been more pleased with how things were shaping up. He began to get dressed, knowing the opportunity to meet his beauty would arrive very soon.

A few minutes later, Tom dialed up his "wingman" Steve Mobley, his closest friend who lived down the road. 15 months ago they had met at the local Dive bar and became fast friends. Steve had also hit it big as a venture capitalist and decided to retire early. Steve was in his mid-40s and had a smooth, calming presence that most women found very appealing. It also helped that he was a 6"5, blond haired, in shape, surfer-model type. Both men took special pride in the conquest of married women, and Steve often accompanied Tom whenever he pursued them at his resort. Tom gave Steve the quick run-down on Mona. From his description, she sounded too good to be true. Steve was in and planned to head over to the resort that afternoon.

Tom also made a quick call to another close American acquaintance, Jake Wyles, who lived 20 minutes away on the other side of Cancun. Like Tom and Steve, Jake had achieved financial success as a stock trader and spent a few months a year in Cancun. He spent much of his time as an amateur videographer and photographer, and he was Tom's "go-to" guy for "special projects" which were always to remain confidential. Tom rarely made these types of "business calls" to Jake, but this occasion called for it and Jake was the man for the job. Like Tom, he had a dark sexual side to him, and an appreciation for beautiful women like Mona, so he was "all in" when he heard about the chance to help Tom with this one. Tom told him to arrive early in the afternoon, and to make himself invisible while getting some footage of Mona at the beach. Tom assured him "he would enjoy every second of it."

It was already after 12 pm and Steve had arrived a few minutes before to rendezvous with Tom. Tom had scouted out two spots at the Tiki bar that gave the men a clear view of everyone entering the beach area. Everything would take place at the Tiki bar around happy hour. Just as they began to discuss how to handle Brian Doyle, Tom tapped Steve's arm - Mona had arrived, and she had found a chair only 50 feet away from where they were sitting. And what a stunner she was -- Steve's cock throbbed as she slowly pulled off her sundress to reveal the hottest milf body he had seen in a long, long time. As she walked over to pick up a towel, her massive breasts jiggled as her top struggled to contain them.

"Wow what a hot fucking milf, " Steve remarked. "And that ass too! It's big and juicy with all the right jiggle." And her bikini was not at all what Steve expected to see after Tom described her as a boring conservative dresser. "It looks like someone wanted to show off the goods today," Steve said.

But the best part of the outfit, as Tom and Steve quickly noticed but apparently Mona did not, was that her bikini bottom became transparent when wet, and the dark pubic hair of her neatly trimmed landing strip was somewhat visible. "That hot bitch," Tom said. "Let's give her time to get comfortable and tan that hot body before we make our move," Steve said quietly.

Tom had also noticed Jake, already set up with his small portable camera back near the far edge of the patio that ran parallel to the beach.

Tom shot him a text that said: "White bikini. Preparing to engage target soon."

Jake glanced over and zoomed in on her luscious rack. He gradually panned down to her white bottoms, which hardly left anything to the imagination, as her camel toe and pubic hair were visible. His cock immediately stiffened in his pants.

"Holy shit Tom. Those tits! This is going to be a lot of FUN," Jake texted back to Tom.

Brian had felt conflicted all day - angry with himself for violating Mona but turned on by the thought of his cock slipping into his wife's tight pussy without her approval. Although he was banned from hanging out with her that day, Brian still hoped to get a glimpse of her lying out in her swimsuit. He slowly made his way to the back of the beach, propping himself up a few feet away from the Tiki bar behind a straw hut.

Brian surveyed the scene. At first he did not see his sexy wife lying face down on the lounge chair. But he soon identified her big juicy butt in what looked like to be a tiny bottom that barely covered anything. He couldn't believe she was wearing an outfit like that without him! She must be really angry. Before he could sneak over to get a closer look, he saw two well-built men staring at his wife and overheard them mentioning her by name. He was confused - how could they know Mona, and why were they talking about her? At that very moment, Tom and Steve got up and began walking in Brian's direction. Brian acted as if he didn't see them coming and stared into the distance.

"Hi my name is Tom and this is my friend Steve. What is yours?"

"Brian. Nice to meet you guys. How can I help you?"

Before he could finish talking, Tom excitedly said, "Brian Doyle who is married to the beautiful Mona?"

"Yep that's me. And you are Tom! Thank you so much for the upgrade and wine. We really appreciate it."

"The pleasure is all mine Brian." Tom said.

"Care to join us for a drink over here at the pool?"

"Sure."

After making small talk and getting a buzz going from the alcohol, Tom commented that Brian was "a lucky man to have a wife as beautiful as Mona, and he must wake up happy every day having a woman like that sleeping next to him."

Brian replied with a stern but intrigued look, "That is a bit forward."

Steve chimed in, "Brian, if you want forward, let's cut the bullshit - your wife is super hot, and I'm sure you must love seeing her show off those big tits and ass of hers in a bikini like the one she is wearing over there. We sure do."

Brian took a big gulp of his drink as he felt his penis become fully erect at the way these men were talking about his wife. He loved that they viewed her in the same way that he did.

"To be honest guys, I think my wife is the most beautiful woman in the world, and it's a turn on to me that you guys like her too," Brian said with a sly smile on his face.

"Like her?" Tom said. "We love her. Excuse my French but she is a hot fucking milf who I would love to get my hands on."

Brian thought about how other husbands would respond angrily to a crude comment like Tom's. But Brian actually enjoyed the way these men perceived his wife and he wanted to bait them further.

"Our sex life has been crappy for a while now and I've been fantasizing about her with other guys," Brian admitted. "I can't believe I'm admitting it, but I love that you guys are interested in her."

"Brian - your wife deserves to be sexually pleasured. If you are open to it, why don't you hang back behind the Tiki bar around happy hour and you can watch us work our magic on your wife. Just one rule - stay in the background and don't interfere. I promise you that you won't regret it." Tom said.

Brian couldn't believe that he was giving these two older men permission to pursue his wife, but the thought of her being pleasured by another man was overpowering and he went with it.

"Go for it guys. She's always been very shy and introverted so good luck in whatever your plan is." Brian said.

"Thanks but we won't need it. Just enjoy the drinks that we will be sending your way," Steve said.

As Brian walked away, Steve whispered to Tom, "Game on. Just keep feeding him drinks and we should be all set. "

Nearly three hours had passed since Mona had stretched out on her chair. She had gotten quite a tan already and enjoyed spending time on her own that afternoon. Mona began to get her things together to go back up to the room when a waiter walked over with a drink, indicating the drink was from a gentleman named Tom at the bar. The waiter pointed to Tom, who waved her over to the Tiki bar 20 feet away. Not wanting to be rude, but also having no interest in being picked up by random men, Mona walked cautiously up to the bar. Jake, stealthily positioned at the far side of the pool away from any resort guests, zoomed his camera in on Mona's jiggling ass, her cheeks bouncing from side to side as she approached the two men.

"Mona!" The gentleman hooted enthusiastically. "My name is Tom and I own this resort. Did you enjoy your wine last night?" Tom said.

Mona's uncertain look quickly changed to a smile, "Oh, it's you! I was wondering when I would get to meet you and thank you in person!"

"Well here I am. You can thank me and my friend Steve here by joining us for a drink." Tom said.

Mona desperately wanted to head up to the room but felt that it would be disrespectful if she turned him down. "Ok well just one - I'm a bit of a lightweight and have been sitting in the sun all day," she said.

The two men charmed Mona as she quickly lost track of how much she was drinking. The Tiki bar was packed with others enjoying happy hour, and nearly every guy in the joint found it difficult to keep their eyes off Mona's massive tits. She was also too inebriated to notice that guys kept "accidentally" bumping into her and one of her large areolas had popped out of her bikini top for all to see. She was completely oblivious to the many eyes that focused on her exposed breast.