Felicity’s Greek Holiday.

Felicity had looked forwards 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, but 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, after all, what is the point of being a multi-millionaire if you could not spend it on the best accommodation available. The villa came with a staff of five, a butler, a chef, a maid, and a gardener but let's not forget the chauffeur come boatman who was there to drive her wherever she wanted to go. A Mercedes and a luxurious boat came as part of the rental of this property, you really do get what you pay for in this world.

She really could not find fault with anything at the villa, it had all the facilities you would expect from a property with it own beach, swimming pool, and little dock. It would be a change having all the staff to do everything for her, definitely not something she had been used to up until now. Like she had most of her life however she felt lonely, she was nearing forty-two and 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 when it came to actually doing it she would chicken out and just run. 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, and she had worried what the postman would think when he delivered it. She was relieved 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 know 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 7 am she was down at the little dock, Demis was already aboard the boat getting it ready to sail. Felicity noticed that he was actually quite handsome, around about thirty years of age, and like the heroes in the stories she loved 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 she could not fail to notice was his tight shorts that did not really leave anything to the imagination, she was looking so intensely at the bulge 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 extremely warm very soon, today 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 that 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. The opposite was actually the truth, many men had fancied her as her body was not really that bad, but they had been put off by the negativity that 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 she changed into a white cotton bikini she came back on deck bringing two cold drinks of lemonade and offered 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 that she from being alone on this boat with such a hunk slipping away, with his genuine laugh she felt much 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 it was released and his cock was hard.

Demis once again reminded her about the sun lotion, breaking the wanderings of her mind that had actually 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, but second by second the temptation 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 began applying the lotion to her back and noticed how tense her body was and he knew that she was obviously suffering from some kind of hang-ups.

“Felicity,” he said, “I have noticed that your body is very tense, 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, she could always tell Demis to stop if she did not like it or her self-doubt 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, he told 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 and he told her that the oil would ruin the straps on the bikini top if he did not release it.

Relenting, she placed her arms that had come up to retie the straps back down by her sides, allowing him to spread some of the oil on her back. Demis was soon rubbing the oil in, he used different types of 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 tension 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 and with this realisation she felt herself getting wetter by the second inside her bikini bottoms. She began moaning in pleasure, and feeling as good she did under his skillful hands, she did not care anymore.

Demis, excited by the moaning decided to take it further, even knowing that if not reciprocated he could lose his job. He slid his powerful 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 and he restarted at the feet and began to make his way back up to 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 here 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 began to massage her from the front, paying special 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, she noticed that the bulge in his shorts was now beginning to strain the material and that the head of his cock was peeping out of the top.

She had not really seen many cocks in her life apart from the ones she had occasionally seen in movies or on television, but 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 would 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, 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 but 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, as 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 they 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. In fact, he still had his cock in his hand as he masturbated at the sight of their coupling, they waved at him, both laughing, and Felicity now feeling much better about her self 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 was not going to be shy and would fuck Demis until he could not take anymore.