Bill's Big Boss

Bill was very much looking forward to this vacation.

He had just got a promotion at work and now the billionaire CEO of his company had invited him and his wife Annie down to one of his vacation homes in Miami. Bill always loved reading by the pool, sipping cocktails, and gawking at women walking by in bikinis. But to be able to do it in January, in the dead of winter, and for free, was fantastic.

Even better, Annie's parents had volunteered to take their two children, ages 3 and 11 months, for the week. Finally, a baby free relaxing environment, and in a luxurious tropical home no less. Annie seemed every bit as excited too.

Frank, Bill's boss, had thought of everything, including first class tickets and a limo to and from the airport. Bill expected the house to be amazing, but the old world spanish architecture mixed with ivy growing on the walls took his breath away.

They were greeted at the door by a gorgeous young woman who introduced herself in a Cuban accent as Rosita and showed the couple to their rooms. The limo driver handled the bags and when Bill went to try and tip him, he refused. "I'm sorry. I am not allowed to accept that. Those are Frank's rules and he is very strict," the driver said.

Rosita asked the couple to please unpack and get comfortable in their room. She would be back shortly with mojitos for both of them, and then she was to give them a tour. Annie and Bill began to unpack as instructed and sure enough Rosita soon returned with Collins glasses glistening with condensation and filled to the top with mint, lime, soda, and of course, rum. They were just the refreshment the couple needed after a long flight.

When they were done unpacking, Annie and Bill emerged from their room and started back to the entryway where they were intercepted by Rosita, who proceeded to give them the grand tour. An indoor gym, sauna, spa, movie theater, wine cellar, indoor pool, outdoor pool, boat house, dock, and of course, boat.

It was quite hot and while Annie enjoyed the heat, Florida was a bit too muggy for her. She announced she was dying to try the pool and asked Bill to come with her back to their room to change into their bathing suits. Rosita said she would have a fresh round of drinks waiting for them poolside when they returned.

It took Bill no time at all to change so he had little to do but admire his wife as she slipped into her poolwear. Annie was still a beautiful woman at the age of 31. She had always been on the curvy side and after two children she was only curvier. She never had a flat stomach, even as a teenager, but what had always been a shapely bubble butt was now even bigger, as was her formally D cup breasts that, while a little droopier than they used to be, were now DDs.

Like most women without nannies and personal trainers, Annie was self-conscious about her post-pregnancy body, so all her bathing suits were very conservative one pieces. Still, with her natural feminine curves, Annie usually captured much male attention at the neighborhood pool. She wasn't tall at just five feet two inches, but she had big brown eyes and a petite feminine nose. It had been awhile since they had been intimate and watching Annie change made a tent out of Bill's bathing suit. Bill tried to make a pass at her, but Annie said she was tired and hot and her neck hurt from the flight and she just wanted to take a dip and relax.

Annie and Bill were another round of mojitos in, when their hosts finally arrived. Frank energetically strode through the covered lanai and out into the pool area. Frank was a big man. 6 foot 4, 220 pounds at least. And he was always sharply dressed, this time wearing an off white linen suit with a black buttoned down shirt. At 55, Frank was in excellent shape. In addition to running at least one marathon every year, he was an avid weightlifter which gave him pecs and biceps which he loved to show off.

Behind him was his wife of just five years, Chloe. She was the third or maybe fourth Mrs. Frank at least, but she played the part well. Comfortable and confident Chloe floated in wearing a floral print drawstring skirt with a large slit exposing one leg all the way to her hip. She topped it off with a cropped cami that while tastefully covering all of her cleavage also left a flat and toned midriff exposed.

The rumor around the office was that she had been an Instagram influencer with millions of followers when Frank reached out to her the day she turned 20. She easily could have been his daughter. In fact, Frank had a daughter older than her from a former wife. But Frank was funny, charming, handsome, and very very rich. They were supposedly married in less than a year.

Bill reached out his hand to greet Frank, but Frank brushed it off and went in for a big hug, completely enveloping Bill's five foot ten inch frame. Frank also didn't wait for Bill to introduce Annie, he simply turned from Bill, bowed to Annie, and offered his hand. "You must be the beautiful Annie I've heard so much about. It is truly an honor to meet you." When Annie then offered her tiny hand in return, Franks elegantly brought it up to his mouth and kissed it.

"My house is your house this week, Mrs. Annie. Anything you want, please tell our caretaker Miss Rosita, and she will be more than happy to get it for you."

"Thank you so much," Annie replied. "Offering this house was so kind of you. We have both really been looking forward to this vacation."

By this time Chloe had caught up to Frank, Bill was about to step forward and introduce himself to her before Frank beat him to the punch. "Annie, Bill, this is my wife Chloe. Chloe, this is our new vice president of compliance Bill, and his beautiful wife Annie."

"It is lovely to finally meet both of you," Chloe said, reaching to shake Bill's hand before going in to kiss Annie's cheek. "Frank has been telling me what a beautiful family you have. I'm sure we are all going to have a wonderful time getting to know each other this week."

Even with Annie rising to meet their hosts, Chloe had to move pretty far down to reach Annie's cheek. At five foot eight inches without heels, Chloe was tall for a woman. In the four inch white heels she had on now she was a full foot taller than Annie... and two inches taller than Bill. Slightly embarrassed Bill had to fight the urge to stand on his toes.

"Please don't move an inch," Frank said to the couple. "A mojito and a dip in the pool sounds perfect. We'll both be right back."

And with that, Frank took Chloe's hand and led her back inside. A few minutes later Frank emerged, mojito in hand, wearing a black bathing suit that covered just as much leg as Bill's, but was obviously tighter up front. Bill blinked twice to make sure he wasn't imagining the outline of an immense shaft beneath the polyester of Frank's trunks. Was it a flashlight? That couldn't be his dick, could it? Annie noticed too but she managed to cover up her reaction better than Bill did.

Frank chose a pool lounger next to Bill where he placed his towel and drink before diving into the pool with perfect form. He swam a lap before exiting the pool right in front of Annie, his pecs, biceps, and six pack on full display as he flexed them to push himself up and out of the water. The outline of a bulky phallus was now even more noticeable since the suit around it was hanging down, heavy with water.

Frank nonchalantly strode past Annie to his lounger and slowly dried himself before sitting down and sipping his drink. "I do love the ocean, and it is fun to swim off the side of the boat, but nothing beats a cool crisp pool to clean off in this muggy heat," Frank said.

"Oh I totally agree," Annie chimed in. "That's why the pool was the first thing I wanted to try after the tour. I'm sure all the guests say this, but this house really is amazing. Thank you so much for letting us stay here."

"You're welcome," Frank replied. "If you two have a good time this week hopefully we can make this a regular occurrence. Chloe and I don't get down here enough."

And with the mention of her name, Chloe entered wearing a simple white two piece bikini, the halter triangle top bravely trying, and failing, to contain her breasts. Her thong bottoms left little to the imagination either. She did add a tasteful flowing sheer cover, but the contrast with Amy's conservative black one piece was striking.

Both women were beautiful but in very different ways. Chloe was blonde and runway-model gorgeous. Annie had wavy brown hair and was girl next door cute. Chloe's body was toned and firm in all the right places, evidence of hundreds of hours in the gym. Annie had the body of an active and healthy woman with a busy life, who had successfully given birth to two babies. Despite their divergent appearances, the girls hit it off.

Chloe wanted to hear all about Annie's children and their home. Turns out the women both grew up in the same town and went to rival high schools, years apart of course. When Annie casually mentioned that her neck still hurt from the flight that morning, Chloe offered to take her upstairs to her massage studio.

"Frank did not want me to have a job after we got married," Chloe explained. "He wants me to be active with hobbies," she continued, "but he doesn't want me to feel like I have to go out and earn money. When I told him I was interested in being a massage therapist, and could practice on him, he jumped at the idea. He built me a studio here at the house and then he bought two spas, one here and one back home. He has somebody else run them, but I can schedule clients whenever I want."

"Will you let me take you upstairs and massage that knot out?" Chloe asked. Annie jumped at the suggestion and the two women disappeared into the house after telling the menfolk where they were going.

Aroused by the idea of his beautiful wife being massaged by an equally beautiful woman, Bill tried to change the subject to business, but Frank was having none of it. "No office talk here my friend. Only pleasure. Please take this week to relax," Frank said. "Is it true you like European football?" Frank continued, "because I think there is a La Liga game on now if you want to watch."

"That sounds awesome," Bill said. "Yeah I think Seville is hosting Valencia today. Do you think you can get the game?" Bill asked.

Frank just laughed. "Yeah I think I can manage. Come on in. How about we switch to beer and take in the game while the ladies get acquainted."

It was halftime before Annie found the menfolk. She looked much more relaxed then Bill remembered and was now wearing a comfortable floral print summer dress. "Bill, Chloe is an amazing masseuse. She knocked my knot right out. I feel so much better. You have to let her massage you this week," Annie said, before turning to Frank.

"Frank, Chloe said Rosita is back with the groceries so you can begin cooking whenever you want. Chloe is treating me to mani pedi at Frank's spa, so we'll be back in another hour or two. Bye!" Annie chirped, before heading out.

"You're a billionaire and you cook your own meals?" Bill asked after Annie had left.

"Ha!" Frank bellowed. "Not all of them. But yes I do enjoy cooking. It helps me relax and be present in the moment. I cook two or three times a week. Rosita handles the rest. And she usually does the shopping too. Let's head into the kitchen. We can watch the rest of this game on the big screen in the living room."

Bill tried to help Frank in the kitchen, but Frank kept shooing him away to the living room to relax and watch the game. And that is where Annie and Chloe found the men when they returned two hours later.

Annie immediately offered to help Frank in the kitchen and refused to take no for an answer. It's not like she wanted to watch soccer anyway, she told him.

Chloe let Frank and Annie work in the kitchen, instead choosing to make herself a fresh mojito and join Bill in the living room.

"Ah, sportsball. My favorite," Chloe said with sarcastic enthusiasm. "Is our team winning?"

"Oh I'm sorry," Bill replied. "We don't have to watch this. We already finished one entire game while you two were gone and this is the second. If anything I'm being indulgent."

"Don't worry. Please keep watching. I insist. This is a week for indulging ourselves," Chloe replied. "Speaking of which, Annie says you havent taken her on vacation in over a year."

"Oh wow she said that?" Bill replied. "That's embarrassing. I guess I don't really keep track. But with a baby about to turn one and another kid under five, life is busy. We've been fortunate enough that Annie has been able to stop nursing, but still living on one salary is tough. This promotion will really help though. I'll be able to take her on more vacations now."

"Yes it is my understanding that Frank intends to take very good care of both of you," Chloe responded. "If you don't mind me asking," Chloe continued, "how did you two meet?"

"Oh that's embarrassing too," Bill admitted. "I had been out paintballing with my friends and I twisted my leg so bad it broke in two places. Annie was my ER nurse. I thought she was super cute and normally I would never have had the courage to ask her out, but the percocet made me a little tipsy so I asked for her phone number. The rest is history."

"Oh that's a cute story," Chloe said. "I'm sure she was just smitten with you too."

"Say, if you don't mind me asking," Bill ventured. "How did you and Frank meet? Is it true you were an Instagram model and he tracked you down?"

"Ha! I've heard that rumor," Chloe said. "In fact I think Frank started it. No, the truth is far more embarrassing for both of us. I was working at a Hooters and Frank came in with a bunch of clients. As you know he is very charming, and he was hitting on me all night. Not in an obnoxious way... just being flirty. And then when he paid for the bill he asked me for my phone number. Normally I didn't date customers, but he gave me such an obscenely large tip, I couldn't say no. Frank saw something he wanted that night and he got it. He always does. The best thing to do is just let it happen and he'll take care of you."

"Ha! That is funny. I can't picture either of you in a Hooters. I mean... not that you couldn't get a job at Hooters I mean you're a gorgeous woman, Oh no, I just told my boss's wife she's gorgeous," Bill sputtered. "I just mean of course you could get a job at Hooters I just mean you seem so sophisticated... I just can't imagine you in a Hooters uniform... not that I would ever try to imagine you in a Hooters uniform."

Bill paused. Despite his best efforts not to, he was definitely picturing Chloe in a Hooters uniform. His face was beet red. Chloe burst out laughing.

"You're sweet," she giggled, reassuring him with a deliberate touch on his elbow. "Look, I'm quite aware of how I look and what effect I have on men. It's not your fault. It's not like Frank asked me out because of my personality. I mean, we eventually did get along, but I know my body is the only reason he asked for my phone number. And I'm fine with that. If I was uncomfortable with men thinking of me in a Hooters uniform, I never would have worn one."

"Now Frank, on the other hand, might not want other men thinking of me in a Hooters outfit," Chloe continued. "And that's probably why he started that Instagram model rumor."

"Your secret, well I guess Frank's secret, is safe with me," Bill said. "Speaking of which, I am getting a little hungry, maybe we could check on the cooks."

Turning their attention to the kitchen, Bill and Chloe could see Frank standing close behind Annie, his arms over hers, his mouth whispering something in her ear. Bill realized Frank was just instructing Annie on some cutting technique, but the two of them looked quite comfortably intimate, and it gave Bill a rush of anxiety.

Chloe seemed much less bothered by the scene, strolling over to the cooks and brushing Frank's shoulder to get his attention before whispering in his ear.

"Appetizers, of course!" Frank exclaimed, as he pointed to one of the mammoth kitchen refrigerators where Chloe pulled out an immaculate charcuterie board. Chloe placed the board down on the kitchen island and waved Bill over to start enjoying the meats, cheeses, olives, etc. It was just the beginning of what became a lovely meal.

After they had retired to their room later that evening, Annie was uncharacteristically frisky and Bill soon discovered what he thought was the reason why. Not only was Annie not wearing any panties under her sun dress, but her womanhood was completely bare. "Chloe sprung for a bikini wax," Annie grinned seductively. "She said we should consider it a gift to both of us from Frank."

"I love it!" Bill exclaimed. And he did. Annie sometimes trimmed down there but nothing like this. He just had to kiss his way down there and see it up close. Normally, Annie would never let Bill go down on her, not since becoming a mother at least. But having her pussy completely shaved gave her a renewed confidence in her body and Bill's tongue felt so good.

Annie laid back and enjoyed Bill's exploration of her newly naked folds, his tongue slowly savoring the length of her slit from the bottom to the top. He then started tongue fucking her hole as she oozed juices and pushed his head deep into her muff. "My clit baby, suck on my clit," Annie begged, which was so uncharacteristic of her. She was normally not much of a talker in bed. But Bill eagerly obeyed. He loved any instruction he could get from Annie, and soon her legs were shaking in orgasm. "Oh god, don't stop, that feels amazing," Annie cried as the orgasm flowed through her.

As her breath returned to normal, Bill wiped his lips clean of Annie's fluids and moved himself on top of Annie so they could tenderly kiss. Bill was about to press his dick into her wet snatch, when she lightly rubbed his head and said, "Don't forget the condom."

Bill didn't actually mind condoms. True, they made it harder to really feel Annie, but Bill also liked that they helped him last longer. Normally, Annie would be on birth control, but she was still in the process of weaning their youngest. The baby was down to about a feeding a day, with solid foods making up the rest.

Bill slank away to put on the condom before mounting Annie once again, easily slipping inside her. She moaned softly as Bill began to thrust into her, lovingly running her hands through his hair. "MMMhmm... go for it baby. I already came," Annie whispered into his ear. And with that permission, Bill picked up his pace, plowing into her as hard as he could, as Annie's body jiggled beneath him.

Bill pushed himself up to look down on his wife, her large breasts undulating in small circles as he did his best to fuck her. The site of her pouty, innocent face, along with her perfectly feminine life-giving mammaries was too much. He came. Hard. And after taking off the condom and throwing it in the trash, he was fast asleep.

Annie was gone when Bill woke up the next morning. A note lay in the bed next to him. "Went sailing with Frank. Back by noon. Love you. Annie."

"Well that's good," Bill thought. He got seasick easily and Annie loved boats. He was more than happy to stay shoreside while Frank took Annie for a cruise.

Bill headed on down to the kitchen to look for breakfast which is where he found Chloe sipping coffee at the island dressed in white yoga pants with flared bottoms, and a tight white mock neck short sleeve crop top, which allowed her, again, to show off her impossibly flat and sexy belly.

"Good morning sleepy head, I hope you enjoyed sleeping in," Chloe said warmly as Bill entered. "We've got coffee and fresh croissants here, or I can have Rosita whip you up an omelet," Chloe offered.

"No, no, that won't be necessary, the croissants smell wonderful," Bill said, pouring himself some coffee. "No sailing for you this morning?" Bill inquired.