Gary Answers A Dateline Advertisement

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Gary had been effectively celibate for nearly a year, except for 'five finger Mary', who lived on the end of his arm. Although masturbation gave him some temporary relief, he longed for prolonged sessions of oral love, fucking and very some light S&M. He had attended some Seniors Centers and various senior social events, but found that most of the women he met there had marriage on their minds. Gary had a wonderful marriage with Lori that lasted forty-eight years until she died. They had raised their children to adulthood and he, at seventy years old, did not want to complicate his remaining years with a wife. Most of the women he met at these 'seniors' functions also had extended families, which did not appeal to him. What he wanted was a sexual relationship that would be satisfying to both he and his partner without involvement or commitments.

He had thought about Cherie and Tabbitha over the past year, but both of them had found men, their age, that loved them and their children. Further, these men were looking for long term relationships that involved marriage. Gary was happy for both of these marvelous women, but sad because he no longer would be making love to either of them. He also considered call girls and prostitutes, but knew that their only interests would be his money and he wasn't ready for that either. Further there was a health risk that he found unacceptable.

He read his morning paper and happened on the Dateline ads. He decided to look them over. As he read and rejected ads for single straight women, his eye caught an interesting ad. 'Single white woman, 55+ yo, slender body with special needs, seeks older man for fruitful relationship without commitments'. Gary circled the ad and continued reading his paper. Later he called the Dateline number and asked about the ad he had circled. He gave the receptionist his name, age and telephone number. Gary really didn't expect any response because of his age, but 'nothing ventured-nothing gained'.

Two weeks passed and he hadn't heard from the woman or the Dateline people. He assumed that his age had prompted the lady to decline calling him and he put the whole incident out of his mind. Gary decided to book a trip to Greece and a cruise of the Greek islands in the Aegean Sea. Perhaps a cruise or a tour of the Greek islands might prove more fruitful. If nothing more it would be a welcomed change from his daily living. His booking was for the next week. The only first class stateroom available had two beds and a private balcony. It was more expensive, but money wasn't a problem so Gary reserved the booking via credit card.

Gary rummaged through his wardrobe seeking appropriate clothing for the trip and found that he was pretty well set. He might have to buy some new items, but he decided to buy them on the trip. Finishing his packing except for his toiletries, he sat down to read the morning paper as he watched TV. The phone rang and he answered. The voice on the other end pleasantly asked, "Is this Gary Harrison?" He answered affirmatively and the voice continued, "This is Monique Caldwell. Are you the Gary that answered my Dateline ad?" she asked.

"Yes, I am," he answered with some excitement in his voice.

"Well hello. I'm glad that you responded to my ad. Not too many men will respond to a fifty-eight year old woman's cry for help," she said teasingly.

"And I'm glad that you called, because I didn't expect any woman to respond to a seventy year old man seeking to satisfy 'special needs' as you put it in your ad, Monique," Gary said to her, "Incidentally, may I ask what those special needs are?"

"Yes, you may, but how about over lunch today, if you're free? And please call me Mona if you like," she said. Gary agreed to meet Mona for lunch and asked her to pick the time and place. Mona picked the Bramwell Country Club, which Gary recognized as a very expensive club to join and belong to. He had lunched there before with friends and told her he would be glad to meet her there. "Good." she said, "Just ask for Mrs. Caldwell's table if you get there before I do. See you at noon, Gary." They said goodbye and Gary hung up the phone. 'Well,' he thought, 'if she belongs to that club she's no ordinary lady and must have tons of money.'

Gary showered, shaved, dressed appropriately for the club and soon was driving his Town Car towards the exclusive Bramwell Country Club. He arrived just after noon and asked for Mrs. Caldwell and he was shown to a small personal dining room off the main dining room. Entering he approached a lady of slender build with an attractive bust line. She stood up to greet him and he saw that her legs were very well shaped with a lovely ass. "Hi, you must be Gary. I'm Monique Caldwell," she said, offering her hand. Gary took her hand, shook hands with her and sat down to join her. He smiled at a very pretty face for a lady of her age, although she looked much younger, with few wrinkles and a very pleasant smile.

"Thank you for inviting me, Monique," Gary said, "I'm very pleased to meet you."

"You're welcome Gary. Let's order, shall we? Everything on the menu is simply splendid, but I favor the luncheon filet." They both ordered the filet and Gary noted that she too ordered her filet medium rare. Monique asked the waiter to bring each of them a glass of wine asking Gary what wine he preferred. He told her a red Zinfandel and she smiled broadly as she ordered the same. "Zinfandel is one of my favorites, both the red, white and the blush," she confided. Gary noted that so far they were both on the same page.

They sipped their wine as they waited for their food. Gary told her that she was a lovely woman and he was very glad to meet her. She accepted his compliments with grace and charm that one would expect of a lady of her obvious status. They made small talk until their food arrived and they ate while still discussing nominal issues. After lunch, they ordered and were served another glass of wine. Monique asked the waiter to shut the door behind him, as he left. "Where to begin?" Monique said as she swirled her wine in her glass, "Gary, I'm going to come candidly to the point and speak plainly." Gary nodded his approval as she began. My special needs are all sexual, Gary. As you probably suspect, money is not a problem with me. My husband, now deceased, left me very well cared for financially.

"He was a wonderful lover. We both loved performing oral sex often and very prolonged sessions between us, was our passion," she continued, "He pleasured me orally and I did the same to him with great relish. Yes, we indulged in intercourse too, in every imaginable position, with some unimaginable ones too," she added with a little smile. "I am not a nymphomaniac, Gary," she said, emphasizing the word, not, "but I am addicted to sex more than most women. "I also admit to enjoying light S&M such as some bondage, spanking and lightly applied clamps wherever you can think of placing them," she concluded with a twinkle in her eye.

Gary smiled and reached out to take her hand in his, "Where have you been hiding these past few years. Monique? You're a girl after my own heart." They laughed at his remark and Gary noticed how comfortable they were with one another. "I'm seventy and I too enjoy all the various sexual activities you just talked about, Monique," he told her. "I'm also widowed, but let me be very clear about one item," he said, "I'm not looking to get married. I've had a wonderful marriage doing all of the wonderful things you obviously enjoyed doing with your husband. Financially, I'm set too, not overwhelmingly wealthy, but sufficiently that I don't want for anything, except good sex with an assist from Viagra. My hair is naturally brown, I don't use any color and I don't know why it hasn't become gray or white," he concluded.

"Gary, you seem to be a perfect match for my needs. I too am not looking for marriage, for the same reasons as you. Once one has had a 'perfect' marriage it is hard to ever conceive of marrying anyone else. But, I do have these wonderful sexual needs and urgings that I have to fulfill soon, or I shall go stark raving mad!" They laughed and began to discuss other aspects of their lives, which once again seemed to fit like hand in glove. Food, wine, music, theatre, art and politics were a perfect match. Both of them knew that they would get along very well.

Monique told Gary that she had to fly to the coast that afternoon to be with her youngest daughter who was expecting a baby any minute and would return toward the middle of next week. She would look forward to long date with him then. Gary told her about the cruise he had booked and that he would try to cancel it. Monique interrupted and told him she would love to cruise the Aegean and would book herself on the same cruise. Gary grinned, knowing that all the first class staterooms were sold out and told her that she could 'bunk' with him since the cruise was sold out. Monique thought that was a splendid idea and offered to pay her share. Gary declined telling her, "It's my treat, Monique. You get to treat me on the cruise," he said slyly. Monique grinned and agreed.

Monique insisted that she pay the check and Gary finally relented. She walked him to his car and gave him her home phone and cell phone numbers, asking him to call and tell her the time she was to be at the pier for departure next week. Monique kissed him on the cheek, promising much more later. Gary returned the kiss to her cheek, thanked her for lunch and drove off. He mused about his lunch date as he drove home. He recalled reading that Monique's husband, George, having passed away last year. Her husband was CEO and sole owner of a computer graphics company. George had sold his company for several hundred million dollars to one of the largest graphics companies in the world. The Caldwell's PR said he wanted to enjoy life, but in truth he had developed severe prostate cancer which soon took his life. Monique had been a widow for less than a full year.

Gary wondered if she had dated anyone since, probably not since she went to great lengths to find just the right person. He hoped that he and she would truly be as compatible as it appeared to be on the surface. The cruise would decide. In the next few days Gary picked up and paid for the double occupancy of the stateroom. He called Monique on her cell and reached her in the hospital where her daughter had just given birth to a son. "Hi grandma," Gary teased her.

"Oh Gary, he's just a beautiful baby boy. I couldn't be happier as a granny," she replied happily. Gary gave her the dates and times for departure. He told her he would meet her at the boarding gate for the airplane in New York, to fly to Athens, Greece. Satisfied with the trip arrangements, Gary notified his home security company, the newspaper delivery service and the local police that he would be gone for the next two weeks on vacation.

On the designated day Gary arrived at JFK airport in New York. He walked to the boarding gate for the flight to Greece and Monique was there, waiting for him. She rose to hug him, telling him how excited she was. Monique whispered in his ear that the waiting was more than she could bear and had pleasured herself nearly every night that she was on the coast. "I hope I fulfill your expectations, Monique," he teased her.

"Oh I just know you will, Gary. I'm so thrilled and horny I might just jump your bones on the plane," she whispered with a grin.

"Well, I'll finally make it into the 'Mile High Club' if you do that," he joked. Monique whispered that she had brought extra pantyhose that he could use to restrain her and two large tubes of KY jelly. "It appears that you have thought of everything," he told her, "I picked up several more Viagra pills from my Doctor, so it seems all the basics are covered." Gary enjoyed Monique's candor about everything. If she had a thought she expressed it and let the chips fall where they may. He liked that a lot about her. "To be honest, Monique, I can't wait to see you naked," he whispered in her ear. She grinned and squeezed his hand.

"Why do you always call me Monique? Most people call me Mona," she asked.

"Because Monique sounds so much more mystifying, intriguing and sexier," Gary said, "At least to me," he added.

Soon the boarding call for the flight was announced and first class passengers boarded first. Monique chose the aisle seat, giving Gary the window. They ordered a Blush wine and sipped it until the flight was backed away from the jet way. Soon the huge powerful engines lifted the big Boeing into the sky and it proceeded to climb towards their cruising altitude. Once there the attendants refilled their wine glasses and brought them their meal. The cabin was chilly and Monique requested a blanket for both of them. Receiving two blankets, they each covered their bodies and welcomed the warmth. Monique held Gary's hand under the blanket and soon brought it to her crotch. Gary felt the soft curls of her bush and slipped his hand lower to let it lie on her moist pussy.

She wore no panties and that pleased Gary no end. Gently, he expertly found her clit and rubbed it as Monique stifled a low moan. Her clit swelled rapidly and was soon erect and engorged. Gary judged that her clit was nearly three quarters of an inch in length and very sensitive. That pleased him too. He trapped her clit between her wet pussy lips and slowly began to roll the upright nub with her wet cuntlips. Monique tried to keep from writhing, but was not too successful, unless the attendants were close by. Gary kept pleasuring her with his fingers bringing her close to orgasm several times only to pause when he sensed she might cum. Monique loved it! She wanted to cum very much, but Gary's keeping her on the edge while denying her relief was so wonderful that she didn't want it to end. She had chosen him wisely, she thought in between trembling.

Gary continued to masturbate Monique as the plane flew into dusk and finally nighttime. The attendants turned off the cabin lights and grinned at them, sensing what was going on. Privately they were wondering if Monique was a screamer when she came and even drew up a little pool amongst the crew. Monique was breathing hard and buried her head into Gary's shoulder as he continued 'tormenting' her clit. He looked around to see if anyone was watching and was pleasantly surprised when a very pretty attendant handed him a finger towel. He unfolded it and a short note appeared stating, 'I'm next, when you finish with that lucky lady,' signed Jan. Gary turned his head to look for her, but she had gone to the galley. Monique moaned softly and bit Gary's jacket to keep her self as quiet as she could.

Monique began to wish that Gary would let her cum, but he was relentless and refused to hurry the job. He correctly guessed that he had been 'tormenting' her for over an hour and finally decided to let her cum. Sensing that she was rising to orgasm, he didn't pause and she erupted in a powerful cum, spewing her juices into the small towel and all over Gary's fingers. She steeled herself not to scream, but Gary kissed her mouth so hard that the only sound she made was a low groan then she bit Gary's jacket again. Gasping for air, her orgasm finally subsided and she was left spent and exhausted. She kissed Gary again and looked deeply into his eyes. Her own eyes displayed the supreme satisfaction of her orgasm. She mouthed the words 'Thank you,' to Gary and laid her head against Gary's shoulder where she soon fell soundly asleep.

Gary wiped his fingers on the towel then looked up to see a smiling flight attendant handing him a hot towelette. He accepted the hot towel and raised his eyebrows as a gesture of having completed a wonderful task. The attendant leaned toward him to adjust his pillow and whispered that if his lady friend ever tossed him out she was available. Gary thanked her for her tolerance and told her it would be his pleasure, but he thought this lady would be a long-term companion. The attendant nodded and left them to sleep the rest of the way. Gary and Monique were awakened when the plane was entering its approach to the Athens airport. Monique smiled and kissed Gary good morning as the huge jet touched down at Athens.

They successfully passed through Customs and soon were in the taxi moving toward the port city of Piraeus. Arriving at their pier they had their bags moved onto their cruise ship, named the Aegean Wind. The ship would be leaving in the early afternoon and Gary and Monique decided to spend the rest of the morning in their stateroom. Once inside their room, Gary locked the door and swept Monique into his arms. They kissed while Monique hurriedly unbuttoned Gary's shirt and removed it. She immediately kissed and licked his nipples, evoking a sigh and a moan from Gary, as he unzipped her dress and let it fall to the floor. Her lack of panties brought her scent to his nostrils, as she was still moist from his masturbating her on the plane. He inhaled her scent as he reached around her to undo her bra.

Monique had unbuckled his belt and his pants fell in a heap around his ankles. He stepped out of them just as he pulled off her bra to marvel at her magnificent breasts. They were not huge, but well shaped with dark areolas and hard nipples nearly a half inch in length. Her breasts heaved as he held her at arms length to marvel at the beauty of her svelte body. Monique's breasts seemed to have yielded somewhat to gravity, but there was only a slight sag to them belying her fifty-eight years. He bent to her breast and licked her areolas and nipples one after the other. Monique sighed deeply and held his head close to her breasts as her other hand reached to his cock, hardened with desire.

She gasped at its heft and at his huge free swinging balls as she fondled him. Gary raised his head from her breasts and kissed her deeply. She pulled him by his cock to the bed and laid down on her back with her legs over the side. Gary stepped back, took two Viagra pills from his shirt as he gazed at her lovely body. Her bush was trimmed, but ample and she had shaved all the hair from around her pussy. Gary kneeled between her legs, swallowed the Viagra and began to kiss and lick her inner thighs as she moaned with pleasure. He nuzzled the soft curls of her bush, sprinkled with traces of gray.

He pulled at her bush with his lips and placed her legs on his shoulders. Monique sighed and ran her fingers through his hair as he licked the creases where her thighs joined her torso. The fragrance of her wet cunt tantalized his nostrils. He kissed her nether lips as though they were her mouth. She gasped and moved her hips up to meet his mouth as he kissed her pussy again. He licked the outsides of her cuntlips, avoiding her clit as it exited its hood seeking attention, but being denied for the moment. "Please," she gasped as Gary ignored her plea and continued teasing her. Monique marveled at Gary's technique as he played with her pussy by pulling her cuntlips with his lips.

She moaned as he sucked each cuntlip into his mouth to lick and savor it before moving on to the other one. Her cunt juices flowed heavily as he allowed her cuntlips to close shut. He gently bit them and pulled them with his teeth, while she moaned aloud. Her breathing was labored as he continued to tease and fondle her pussy with his mouth. She gave a start as he parted her cuntlips with his tongue while he reached up to rub her hard erect nipples with his finger tips. Monique groaned with pleasure as his tongue swirled into the pink inner folds of her pussy. Her juices flowed into his mouth and he eagerly swallowed them as he licked her relentlessly.