Felicity had looked forward to this trip for such a long time; she had always loved the old stories of the gods and heroes of ancient Greece. Recently she had a lottery win that was quite substantial, and it had allowed her to give up her job down at the local nail parlour.
Being single and not ever having had much luck with men, she decided the time was ripe to travel to the places she had always dreamed of. She wondered whether she would be able to find a swarthy, muscle-bound Greek Adonis. Still, she did not consider herself anything special and doubted that they would even give her a second look.
Rather than staying at a hotel, she had decided to rent an exclusive villa on the small island of Limnos. After all, what is the point of being a multi-millionaire if you could not spend it on the best accommodation available? The estate came with a staff of five, a butler, a chef, a maid, and a gardener but let’s not forget the chauffeur stroke boatman who was there to drive her wherever she wanted to go. In addition, a Mercedes and luxurious boat came as part of the rental of this property; you indeed get what you pay for in this world.
She really could not find fault with anything at the property. It had all the facilities you would expect from a property with its private beach, swimming pool and little dock. However, it would be a change having all the staff do everything for her, definitely not something she had been used to until now. Like she had most of her life; however, she felt lonely, nearing forty-two, she still had not lost her virginity, at least as far as men were concerned.
Don’t get me wrong, she had fantasised about sex, but she would chicken out and just run when it came to doing it. Insecure in herself, she had resorted to masturbation her whole life, firstly with her fingers, later graduating to vegetables and eventually a vibrator. Being a timid and insular type of woman, it had taken her all her courage to even order the vibrator from an online vendor. She had worried what the postman would think when he delivered it, So her relief was great when it came in an anonymous brown paper-covered parcel.
She had resigned herself to life with her toy and no men; little did she understand that her life would soon change in drastic ways.
On her fourth day at the villa, Felicity decided that she would like Demis, the chauffeur and boatman, to take her out in the boat to visit some of the other islands close to Limnos. The plan was to be back in time for dinner and so at seven am, she was down at the little dock; Demis was already aboard the boat getting it ready to sail. Felicity noticed that he was strikingly handsome, around about thirty years of age and like the heroes in the stories, that entranced her so much he had the body of a demigod. She looked him over, noticing that his T-shirt was tight on his manly chest. Another thing that Felicity could not fail to see was the bulge in his shorts that did not really leave anything to the imagination. She was looking intensely at the shape of his cock inside his shorts that, at first, she did not hear him as he spoke to her.
“The boat is ready, Miss Kendall. Would you like to come aboard?” He asked with a grin on his face knowing what had distracted her.
“Sorry, erm, yes, yes, of course”, Felicity responded.
As she came aboard, Demis held out his hand to help her aboard, which she gladly took; she could see that his hands were strong yet gentle at the same time and wondered what it would feel like to have them caress her body. Pushing these thoughts aside, she sat down on one of the boat’s seats whilst Demis let go of the lines and started the engine.
They were soon making headway, and Felicity marvelled at the beauty of the rising sun as the breeze blew her hair behind her. At this moment, she relished the peace of being out on the sea, relaxing like she had never relaxed before.
“Miss Kendall, miss Kendall,” said Demis bringing her back from her revelry,
“It will be hot today, and we are expecting temperatures of about forty-three degrees celsius. Perhaps you would like to go into the cabin and change into your swimsuit.”
Being the worrier and self-loather she had been all her life, she wondered what Demis would think of her in a bathing suit, feeling that her body was all out of shape and ugly. However, the opposite was actually the truth. Many men fancied her as her body was not that bad, but they had been put off by the negativity she exuded.
Building up her courage, she decided to change rather than suffer in the heat of what, even at just before eight, was already a hot day. After changing into a white cotton bikini, she came back on deck bringing two cold glasses of lemonade. Offering one to Demis, which he gratefully accepted and downed all in one go.
“The sun will start to get very hot soon, Miss Kendall; you really should put on some sun lotion, or you will burn with your fair skin,” Demis told her.
“Please, Demis, call me Felicity; you make me feel so old by calling me Miss Kendall,” Felicity said.
“Very, well, Felicity, it is miss Kendall,” laughing along with Felicity as he realised what he had just said.
Felicity felt the tension she had from being alone on this boat with such a hunk slipping away. With his genuine laugh, she felt more relaxed and once again, her eyes fell to the bulge in his shorts. Though she tried to resist the thoughts, she wondered what that bulge would be like if his cock was released from their constraints.
Demis reminded her again about the sun lotion. This broke the wanderings of her mind that had left a wet mark on her bikini bottoms that had not missed attention by Demis. Feeling her juices on her pants, she was embarrassed and turned away, hoping that Demis had not noticed but deep down knowing he had.
“Miss Kendall, sorry Felicity, would you like me to apply the lotion to your back?” He asked.
Felicity tried to resist the temptation to say yes. Yet, second, by second, her desire was growing, and in a wavering voice, she said that she would appreciate that.
Demis put the boat into neutral and switched off the engine. The only other boats they could see were a few fishing boats in the distance. He placed a blanket on the deck and began applying the lotion to her back, noticing how tense her body was. He knew that she was obviously suffering from some kind of hang-ups.
“Felicity,” he said, “I have noticed that your body is taut, “I could give you a massage if you like; it should help you to relax.”
Felicity was in a quandary; she did not want to accept in her mind that she was scared of sex but so in need of it. She had never had a massage before because basically she had never been able to afford one, nor had she the self-confidence to have one.
She decided that she would try it. There was the option of telling Demis to stop if she did not like it or if her doubts got the better of her.
“OK, I will let you massage me, Demis,” she replied.
Demis laid out a blanket on the deck and asked her to relax on it facedown whilst he went into the cabin and brought out some massage oils.
Nervously she did as instructed, resting her head on her arms. When he came out of the cabin, Demis handed her a cushion for her head, telling her to place her arms down by her side, which she did. She felt a twinge of doubt as he undid the strap on the top part of her bikini; she asked him what he thought he was doing. Demis told her that the oil would ruin the straps on the bikini top if he did not release it.
Her sudden fear subsiding, Felicity allowed him to spread some of the oil on her back. Rubbing the oil in, he used different movements, and she could feel the tension being released from her back; Demis really knows what he is doing, she thought.
As his hands moved over her, she could sense not only the hardness leaving her body but a feeling of arousal such as she had not really felt before.
His hands began to rub her lower back, first in circular motions and then a soft kneading. She could not help herself; she wanted his hands on other parts of her body. With this realisation, she felt herself getting wetter by the second inside her bikini bottoms. Finally, she began moaning in pleasure and feeling as good she did under his skilful hands; she did not care anymore.
Demis, excited by the moaning, decided to take it further, even knowing that he could lose his job if not reciprocated. He slid his manly yet gentle hands inside the bikini bottoms, caressing her cheeks and his fingers exploring the crack between them. As she moaned even more at this sensation, she raised her backside from the deck and told Demis to take them off.
Taking his hands out of them, he took them down, sliding them down her legs, and as she once again laid down on the blanket, he slipped them over her feet whilst at the same time Felicity removed the bra. She was now completely naked; she instructed Demis to carry on with the massage. He restarted at the feet and began to make his way back up to her now moist pussy.
He applied more oil to her backside and made sure that some went down between the cheeks and onto her neatly trimmed bush and pussy. His fingers caressed her labia, rubbing the oil into them; he then inserted his index finger inside, emboldened by her increasing moans of pleasure.
Knowing that she really needed this, it was that obvious; he inserted another finger and began to finger fuck her sending her into spasms of pleasure. He felt her time was near and increased the pace of his fingers before she shot her juices onto them; taking them out, he licked them, enjoying her saltiness.
He asked her to turn over and massaged her from the front, paying particular attention to her breasts with their now erect nipples. Felicity told him to take off his damned clothes and let her see what he had underneath, wild now with the lust of the moment. He removed his T-shirt, revealing a perfect set of abs and a hairless muscular chest. Felicity noticed that the bulge in his shorts was now beginning to strain the material. Her eyes grew wide as she saw the head of his cock now peeping out of the top.
She had not seen many cocks in her life apart from the ones she had occasionally seen in movies or on television. What she did know was that this one was no slouch when it came to cocks. With a good eye for sizing things up, she just knew it was a little over nine and a half inches with a thickness of an inch and three quarters, and she knew she had to have it in her.
Today she had decided was to be her last as a virgin, and she told Demis to fuck her and fuck her hard.
Demis needed no further invitation, and getting in between her legs, he moved up and pushed his way in. As he moved in and out, Felicity asked herself why she had waited so long in life for such an experience as this. She began to feel the frustrations of her near forty-two years without real sex melt away. She became engulfed by sensations that she had never experienced with vegetables or her vibrator.
Demis increased his speed as he felt his cum begin to churn and make its way up his shaft, wondering if he should pull out. By this time, Felicity’s legs were around his back, as were her arms holding him tight. As his sperm burst into her, Felicity’s nails scratched deep grooves into his back, drawing blood. Demis, like her, let out a guttural scream with the pain and the pleasure combined into one.
They sank as one onto the deck, for the moment sated and breathing heavily. Sitting up, Demis and Felicity noticed that there were now quite a few boats around, and one had a man aboard who had been watching what they had been doing. He still had his cock in his hand as he masturbated at the sight of their coupling, and they waved at him. Both laughing, and Felicity, now feeling much better about herself, blew him a kiss.
“Let’s head back now Demis, I will give the rest of the staff a day off, and we can enjoy the pool and the sauna back at the villa uninterrupted.”
They quickly dressed once more and made their way back to the dock and the villa. Once bitten, Felicity decided she would not be shy and would fuck Demis until he could not take anymore.