Thanksgiving in Maui

Author's Note: All sexual participants are over 18 years old. This is a work of fiction that I've written for fun. This work is intended for people 18 years of age and older. If you are reading this and are under 18, please go to another website or story.

Chapter 1 is a story about a retired gentleman finding fun again after his wife tragically passed away. If you are looking for a quick jump in the sack, this isn't it.

Chapter 1 - Preparation ...

Bob Walters sat at his computer in his den. It was a gift from his two boys the previous Christmas and it had taken him almost all year to learn how to really use the damn thing.

With Thanksgiving approaching, he wanted to have a small family reunion and he wanted to create semi-formal invitations for his boys and their families to join him on the lovely island of Maui for Thanksgiving.

Bob grew up just south of Boston, only a few miles from the famed Pilgrim Plantation. He believed in his family's tradition that family and friends should gather together, near the end of November, and feed on turkey, stuffing, cranberry sauce, and incredible deserts. But Bob had moved to Mauii three years early with his wife of 30 years only to have her fall victim to ovarian cancer soon after moving. Her name was Gail, and she had been a wonderful woman and fabulous wife and Bob loved her dearly. She was a woman whose inner light lit all those around her. Magnanimous, caring and giving, she was a constant source of how imperfect Bob often felt. The cancer took her quickly so her pain was done but Bob's pain continued on in everything he did and everyone he saw.

It had been all set. What they had worked for and saved for their entire lives had come to fruition. Bob had designed the cluster of cabins on a downward slope of land leading to a small beach. The cabins would be a source of income and a place for his and her large extended families to come and visit. The building had gone well with their cabin at the top and a series of decks and waterfalls leading down to the cabins and the main pool. It was all perfect only ovarian cancer struck Gail in their 3rd month there. Bob watched her wither away and die within a few months.

It was tempting to move back to family and friends in Boston but something called to him to stay in Maui. At 63 years old, and a shade over 6'2" tall, he was semi retired but still extremely active athletically. Without Gail, he pushed himself deeper into his athletic endeavors. He played golf, biked, tennis, swam, and climbed the hills and mountains around the large cabin he had retired to. He took risks on his mountain climbs and one time stood on a precipace and weeped openly. As his eyes grew moist, he looked down and leaned forward. It could be so easy to fall off, but he held himself there on the edge of a cliff. You could say that he held himself on the edge of his life.

He rented the cabins out. Mostly they were vacation rentals but on occasion, there were some locals who rented them for a few months. Most of the income, he was setting aside as a surprise for his kids as he really didn't need it.

He looked at the blank screen before his eyes and finally composed his email and then composed it a 2nd, 3rd and 4th time. It was important to send it by the end of September so that they could ensure they they could make the trip. The boys and their wives had come for visits before and after Gail's passing but it had been almost a year since he had seen them. Finally, he clicked "send" and the email was off. It basically said: I miss you; Please visit for Thanksgiving; I'll get a nanny for Jarod; I'm paying!

Bob closed his browser but stopped for a moment. He felt a stirring in his shorts and shook his head. One thing that was very difficult to get used to was the lack of sex. Gail had been voracious in that department of life and kept him well pleased. He found himself using his hand and it was less than satisfying compared to caressing her soft breasts and sucking her long nipples. Most of all, he missed pleasing her and watching her cum as his cock pounded her pussy.

He re-opened his browser and found his favorite website. It was an amateur site filled with men who liked being voyeurs. They took pictures of their wives and posted them on-line and enjoyed the knowledge that other guys were enjoying THEIR wives. Bob found a video clip of a buxom woman with large aureoles. He stroked his dick and felt it grow stronger, pulling it from the confines of his shorts. She slowly teased by pulling down her sweater and then pulling it back up with a haughty laugh as her nipples became erect. She blew a kiss. Bob imagined her full lips wrapping around his thick cock and he stroked himself.

The clip was 4 minutes long and at the 3 minute mark, Bob's hand stroked rapidly as he watched her squeeze her nipples. A milky white substance emerged and she smiled that knowing smile that she has big tits, a tight pussy, narrow hips, and the killer of all horny men, leaking and milking nipples. She squeezed and the left breast squirted and Bob groaned. She squeezed the right and he could feel his balls ache to explode. She reached up with both hands and laughed as she squeezed her big tits down to her nipples and both breasts sprayed milk toward the camera. Bob could hear the husband behind the camera: "Baby, you made me cum in my pants!"

Bob came too.

* * *

The invitation came to Sara Walters and she immediately picked up the phone and called her sister-in-law.

"Are you going? Please say that you are going!" she implored.

"I don't know if we can afford it, Sara," said Lisa.

"Didn't you read it? He's paying the expenses and the cabins are free. We get a free trip to Hawaii! Come on, I want to see you there."

"I think Todd is up to it but I just don't know about flying 12 hours with a baby. Plus my mother is also having Thanksgiving at her house."

"Lisa, you have got to find a way to come. We'll have so much! We'll shop, we'll swim, we'll tan! The boys can golf."

"That's great for you. I've got a baby and you'll probably be making your first!"

"You didn't really read his invite, did you! It says that he is going to hire a nanny for Jarod,so don't worry! Say 'yes'! ... PLEASE!"

"Yes, we'll see."

Lisa Walters laughed as she hung up the phone. If she was going to go, she only had 6 weeks to really lose this baby fat. Jarod was almost six months old and though she worked out regularly, the fat just didn't seem to come off her thighs and hips. Plus, her tits hadn't returned to their normal size. It wasn't a bad thing. After all, Mark seemed to like them! She had avoided the beaches of Cape Cod all summer long and had refused to buy a larger bathing suit.

Over the next hour as Jarod napped, she cleaned out the refrigerator of all the unhealthy foods and made a list. "Whole foods, here I come," she thought to herself.

* * *

Bob had found Craigslist pretty easily and posted his ad for a qualified nanny. Now he was getting emails from various Maui residents looking for a little extra pay. He had forgotten to specify the hours required for the 10 days he needed nanny help. There were some who were available evenings and some were available days and a few that were available full time or were willing to be on-call.

He really hadn't thought this all through, yet. There were many that he just pushed into the digital wastebasket and after a few days of reading through resumes, he had it narrowed down to 3 women. The interviews went well but one woman really caught his interest.

Her name was Ria. Really, it was a nickname so that English speakers could pronounce it. She was born of Hawaiian and Filipino parents. She stood in his doorway at 5'5" tall, unusual in a Filipino, with her 9 month old baby comfortably on her hip. Her smile was wide and bright topped with classic Filipino high cheekbones, sparkling green eyes and long flowing dark brown hair with blond streaks.

"I'm Ria and I'm pleased to meet with you." she reached out her small hand and Bob took it.

"Yes, I'm uhh, Bob Walters and I am happy to meet with you too!"

She put her child down on a blanket with a few toys. He was very well behaved and played with a set of large brightly colored, plastic keys as they talked.

Bob was smitten by her smile, the way she tossed her hair back, and her smooth golden skin. She needed a place to live and was willing to take whatever salary he offered as she had just left her husband only 3 weeks earlier. She declined to discuss the circumstances of their parting and apologized to Bob that although her situation seemed unstable, she was a very stable person.

Bob hesitated. Maybe there was some confusion. "You know that this is a temporary job. It's just for 10 days."

She looked heart broken. "10 days? Oh no, I didn't see that in the ad."

"Yes, I'm so sorry. It's really my mistake. I'm not so good with computers and I probably neglected to put that in there."

She stood. Tears flashed briefly in her eyes. "Well, I need something more permanent than that. It's just so hard to have a child and hold a job without a support structure. I hate being on unemployment and I hate being on welfare and I have no one to watch my kid while I work."

"What about your parents?"

"They both work and honestly, it was hard to move back in with my parents as a 32 year old. I've been independent for close to 10 years and now. So, I'm with them now but I'm sleeping in a small room with my little brother." She laughed, "He's not really all that keen on it either. So, I've got to get out. In order to get out, I have to get a job!"

Bob nodded. "Sorry about that mistake. I just goofed on the ad."

"Well, thanks for meeting with me. I'll just go on to the next opportunity."

"What opportunity is that?"

She looked at the paper in her hand. "It's a dog walking job. I've got to start somewhere!" her cheery mood returned.

"Hang on. Would you be willing to do some cleaning and take care of a pool area and 4 hot tubs prior to the time when I need a nanny?"

"What do you mean?"

"I've got 4 cabins in addition to mine. As you look out my window ..."

"Nice view!"

"Thanks. You can see the cabins on the right. They are 3 bedrooms and each has a hot tub on their private deck. There is a shared pool in the middle of them."

"It's more like a villa!"

"Yes, I guess. I designed it."

"And you have your own kidney shaped pool here on your deck."

"Yes, and on the right is a walkway to the beach. The only way to get to the beach is that walkway and by boat so it is pretty secluded."

"Wow, this is quite the property," she spoke with a slight sense of awe.

"Built on a hill like this and facing west, I get the sunsets each day out these large windows. The ocean is only 150 yards away and the cabins have their own privacy and view too."

"Well, I've never taken care of a pool or hot tubs. I don't know about the chemicals or anything but I don't mind cleaning."

"Here's the deal," he smiled. "I like you. I think we can work this out. I have a cabin that is available. You get to live in one of the cabins free until January 15th. No parties, no family overnighters or anything like that. Otherwise, you are just another renter and can used the facilities just like any other renter. You sweep and clean the pool areas, the decks and hot tub areas before and after renters. The pay is $100/week. This is pending a background investigation and your references check, of course."

She smiled brightly. She needed more cash than that to pay off her debts but at least it was a start and a place to live. "It's a deal!"

He checked her references and they were excellent. He gave her the schedule so she could ensure the pool and hot tub areas were clean. It was off-season so there really wasn't much work to do.

* * *

Bob stretched as he left his bedroom to look out the window at the beach, the surf, and the islands in the distance. It was late for him but he still had his early morning woody.

It was great having Ria around. The cabins were rarely rented now and one of the renters had just left the day before. He was surprised at the zealous job she was doing. So, all the guests were gone and there wouldn't be any new renters until after the family arrived for Thanksgiving. Generally she carried her baby in a backpack as she cleaned. Renters tended to leave crap around when they left and she was right on top of it. He found it to be a good deal for both of them already.

He stepped into his living room and yawned. Stretching his arms over his head, he thought about relieving his hardon by looking at his favorite porn sites. And there she stood about 4 feet from him cleaning the deck and his pool area. At least, she was until she saw him in his shorts with his cock hanging out the slot of his boxers. His eyes widened and so did hers.

The baby was asleep on her back. She glanced down at his hardness and smiled. He looked down too. It was still thick and hard and pointed straight out. He tried to cover it but failed so he turned and quickly went to the bathroom.

Ria stood a moment longer enjoying the lingering image of that fit older man and his long cock. She had no idea that he was hung like a horse. It had been more than 3 months since she got laid and she wondered how long it had been for him.

That afternoon, Ria was at the main pool enjoying the sunshine. She had fixed a light snack of cut apples, mango, and papaya. Bob came down the brick stairs with a small cooler. He had just ridden his bicycle up and down a mountain and he had a slight gleaming sweat covering his bare chest that was sprinkled with gray hairs.

"May I join you?" he asked.

"Please! I could use the company of an adult!" she smiled broadly.

As he sat in the lounge chair next to her, opened a beer and offered her one. She declined.

"I'm sorry about this morning," he started.

"No, it was my fault. I shouldn't have been there so early."

"Well, I guess we are both sorry. Let's put it behind us."

"Ok, well. If you were uncomfortable, I certainly don't want to have that happen again."

"Yes, umm, I guess it is just going to take some time to get used to having someone here even when there aren't any guests.

She reclined on the lounge and rambled about her father, her brother and her mother. One of her knees was bent up slightly. Her bronzed legs led to her short, jean shorts. Her shirt was open up the middle revealing a flat stomach and a bathing suit top underneath. He could not see much but he knew that the shirt was over-sized. He finished his beer and drained a second.

Bob walked to the outdoor shower and turned on the water. He still hadn't gotten used to the fact that in Hawaii, you really don't need hot water at an outdoor shower. He stepped under its cool spray and rinsed off the dried sweat.

The pool was waiting and he dove in, swam the full length and returned. With his arms up on the side, he looked at her. "Coming in?" he asked.

She pointed to her child a few feet away. "Let me feed him and I'll be right in!"

She picked him up, opened her shirt wider, and lifted her bikini top releasing a massive breast to her child's lips. He sucked and gurgled actively as the warm milk filled his cheeks and slipped down his throat.

Bob tried not to stare. After only a few minutes, Ria switched him to the other breast leaving her drained breast uncovered. The nipple dripped a creamy liquid. Bob looked away.

"It's about the only way he takes a nap now. Either this or in the backpack. That seems to work too."

Bob was speechless. A few minutes later, she was standing above him pulling down her short, jean shorts.

Her legs were longer than most on the island. Her thighs and calves were thin and brown. Her feet were small and tanned. Her bathing suite bottoms were different than her top. The bottom was a bright green French cut while the top was fluorescent orange halter top. Her hips were narrow leaving a small space between her thighs. The halter top barely contained her breasts as they pressed together creating a 5 inch cleavage. Her nipples, still hard from their brief stimulation, pressed against the flimsy material. She raised her arms over her head to put her long hair in a bun. As her arms whirled around her full breasts bounced lightly.

"This is my pre-pregnancy bathing suite. It kinda doesn't fit anymore."

Bob wasn't sure what to say. He could feel his cock pressing against his swim shorts. "Looks fine to me" he offered.

She smiled. Blushed. "Thanks" and climbed into the pool.

She swam back and forth a few times. He was been speechless as her legs and ass churned the water before him. She came to him and got close. He was concerned that she would bump his cock. She climbed out next to him.

"Bob," she started, "We're both missing something."

She touched his shoulder and stroked his neck lightly and he nodded agreement.

"I know," he responded.

She ruffled his hair slightly, leaned over and kissed his head.

"We shouldn't do this. I'm old enough to be your father."

"Bob, you're a man. I'm a woman. We BOTH have needs. Why not satisfy them?"

"You could be my daughter!" he said with a laugh. He refused to turn and look at her.

"Yes, if you find that kinky. I'm ok with it but I thought you had two boys."

"I do!" and he turned and her halter top was off.

"Do you mind if I go topless while there aren't any renters?"

"Uh, no," he stammered. "Not at all."

They were there before him. Golden tanned, large and full with thick, dark brown nipples pushing out proud from her chest. She scratched the sides and stretched slightly pushing them out further.

"They needed release. It's hard for my girls to be couped up inside a bra that's too small!"

Bob nodded absently.

"You'd like to touch them?" she asked.

"Ria, I can't. I'm not sure that this relationship is working out."

"I can put them away if you want," Ria shook them slightly and leaned into him so that her nipples grazed his bicep, "but I don't think that is what you really want."

He turned and drew her to him into the water. She latched her arms around his neck and felt his hardness against her stomach. Their faces close she whispered. "It doesn't have to be love, Bob. Just some release from the tension. Just some release from a friend helping another friend. You helped me in my hour of worst need. You were a friend. I want to be a friend back and release some of your tension ... and maybe some of my tension too."

She reached down and pushed his shorts to the bottom of the pool and felt for his pole. It was even thicker than she expected as she slowly pulled the skin back and forth over the hardness. The head was plum sized and purple. It filled her small hand.

"This isn't right." he whispered half heartedly with a grunt.

"Yes, it IS right. Just a man and a woman."

She pulled on his pole harder and looked forward to having it inside her. The veins were bulging now. How could an older gentleman have such a hard cock? Her bottoms found their way to the bottom of the pool, too. Her tits hung down and and rubbed her nipples across the head. Bob had his eyes closed and she didn't know if it was some sort of shame or enjoyment. She hoped it was enjoyment. If his hard cock was any indication, it was enjoyment. Ria lifted her right leg onto his hip and eased his cock head between her pussy lips. She felt him stiffen and then put his hands on her ass guiding her up and onto him.

As she slowly worked her pussy on his cock she watched his eyes roam her body. She was half submerged in the water and riding him, enjoying him, and her tits slapped at each stroke. She felt him rising inside her. It was big and fulfilling. She was being filled and loved the sensation.