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."
