Holidays with Benefits

It was his custom to step out onto the veranda and take in the view. He believed he could never tire of seeing the sun set into the bright blue sea, with the yellow sandy beach in the foreground. It was just perfect. His attention was distracted by a figure running towards the car park; from the bright-blue polo shirt he knew it must be Lauren. Anyway the car she had just got into was clearly hers. This was the third time in the last week that he had seen her upset. Again the temptation to intervene gnawed at his conscious. He really treasured his anonymity on the island and had no wish to lose it. On the other hand he was not the sort of man just to stand by and watch someone struggling. Especially when he knew what was causing it.

The following morning he wandered by Lauren's desk in the reception area of the hotel. As usual she was staring into her iPad, which was resting upright on its case in front of her. She smiled and wished Leo a good morning. Leo looked into her big brown eyes and saw the strain and tiredness that lay behind them and that instantly made up his mind to act.

"Hi, Lauren," he said. "How about a cappuccino before you go? We should talk." He knew she normally left in about thirty minutes or so and grabbed a quick coffee before she went. Initially she refused, but he persisted, and in the end she somewhat reluctantly agreed. Her enthusiasm waned even more when he suggested they had the drink in his villa. Committed now, she felt unable to back out. However, Leo observing her car was parked right by his place, and so she wouldn't lose any time coming to his villa, did little to make her feel easier. She even wondered for a moment if he had been spying on her.

However, he did a good job of making her feel relaxed when they finally got to the villa. She parked herself in a comfy armchair. She watched him making the coffee and wondered for the first time about Leo. He seemed to live quietly in the hotel, no one took any notice of him, other than to serve him and she had seen him be charming to staff and guests alike. All in a quiet unassuming kind of way. For all that he was good-looking and athletic, although he was to her 19 years old eye's very old. She had no idea how old, but her eyes then saw a bunch of birthday cards announcing his fiftieth birthday. Wow that old she thought. Seeing birthday cards in a holiday villa was odd too; did he live here all the time?

The coffee was lovely and made to perfection in one of those top of the range Nespresso machines. Lauren's mum had one at home so it was extra nice, but it did remind her of home and the feelings of homesickness welled up inside her once again. Leo sat down opposite her with his own drink and smiled at her. His opening comment made her forget all about home.

"Lauren, you will probably think this none of my business, but you don't seem very happy." He said bluntly. She started to protest, but was shot-down by Leo explaining he had seen her in tears three times in one week. Again she started to be defensive, but was again stopped in her tracks by what Leo said. "I take it Margaret is giving you a hard time," he said.

Margaret managed the team of holiday reps in which Lauren was a team member. As the only new starter that season Lauren had been made to feel a complete outsider. All the other reps appeared to be Margaret friends. Margaret though had seemed to hate Lauren from the moment she met her. She was too posh, too pretty, too hard working. To Margaret being a holiday rep was about meeting lads, getting pissed and then laid. She wasn't about to tolerate some bloody outsider making her and everyone else look bad. Amazingly to Lauren, Leo had worked out what was happening, so had guessed what had occurred.

"Don't worry," he said. "Margaret always sends the ones she doesn't like to this hotel, after all its full of crinklies. No chance of getting shagged." The last sentence he said in a brilliant imitation of Margaret's accent, which made Lauren laugh. "That's better," he said. "Its good to see you smiling." That was when Lauren told him she had forty tickets to sell to a pub-crawl and nightclub trip that she was meant to organise. Of course she had been set up to fail, because no one in this hotel would be interested in something so clearly aimed at the twenty nothings, and she had no idea where else to go.

In a backhanded comment that made Leo laugh, she told him, "after all you are one of the younger ones at the hotel and you wouldn't want to go would you?" He protested that he might want a night out getting drunk, and they had laughed about what she had said. Leo, always a man of action, announced he was going to help her get rid of the tickets. Incredibly within two hours she had sold them all, but the two she needed to keep back. Leo was a marvel. He seemed to know everyone. He sent her to two hotels, where they snapped up the tickets in no time.

Margaret was clearly stunned when Lauren arrived at the office with the ticket stubs and money. Sadly however, Margaret's shock turned very quickly to anger, and Lauren was told she was, "on her own," she could run the evening herself. Margaret had been meant to have one of the spare tickets, Lauren the other and together they would host the evening. Now Lauren was abandoned.

"You had better fucking sell that spare ticket too," Margaret said, "and remember to get everyone to fill in a survey. I want to know if they had a good time and if they didn't then you are fired." Lauren left crestfallen, and once more trying hard not to cry. Thirty minutes later Leo was answering a knock at his villa door and consoling a distraught Lauren. It was she though who realised that Leo buying the spare ticket was the solution to all her problems. It was someone to help her on the night and she also got rid of the remaining ticket. As she said selling a single would be impossible. The way Leo had argued that he was not too old for such a night now came back and haunted him. He resisted valiantly for a while but in the end he handed over the fifty euro's for the ticket. He could not leave a damsel in distress could he?

Part two

When Leo opened his eyes they hurt, despite the curtains being pulled and the light therefore being pretty dull. So he closed them again. Where the hell am I, wandered through his mind, as he struggled to think. Realising he was in his villa Leo sat quickly upright, but that just made his head spin, so he flopped back down again. He had no memory of anything after playing drinking games at the third bar they had gone to. God knows how he got home, but he was relieved to see he was still dressed. He vowed never to drink again.

On the side were two big bottles of water and some aspirin with a note. It was from Lauren. She said that they had brought him home and put him to bed. He really had no idea who "they" were, but clearly Lauren had left the water and pain killers and for that he was very eternally grateful. Lauren went on to say that she hoped he would be okay, and there were lots of thanks and kisses. Also there was a comment that everyone sent their best wishes too, and that they had all had a great time. Leo imagined he had had a great time too, he just wished he could remember it.

It was mid-afternoon when he braved the hotel lobby and a cup of coffee. He was surprised to see a very happy Lauren walking towards him across the floor of the hotel.

"How are you?" She said, looking concerned. Leo smiled weekly and said he would live. "Good." She said. "Because here is your ticket to next weeks night out." Leo looked confused, then worried. "It was your idea remember?" She said. "You talked everyone into rebooking for next week too. Apart from the fact you passed out before you could pay for your ticket. But everyone agreed it would not be the same without you, and so they clubbed together and bought yours. And so here it is." Lauren handed it over, smiling at the way his hand was shaking as he took it. And at that point she kissed him on the cheek, her lips lingered on his skin for just a moment longer than necessary and her hand behind his back caressed him momentarily. She told him he was amazing and left.

He watched her tight little ass swaying across the floor. In the very tight, short grey skirts that was part of the holiday's firms uniform. He noticed for the first time the bright golden-coloured zip that seemed to go all the way down. Her shapely legs were nicely tanned and looked good even in the flat shoes she was wearing. He pushed the wicked ideas, which were making his cock tingled with expectation, out of his mind. She was too young for him, but there had been something in that kiss that made him wonder. He called for another coffee, if only to put the fire out down below.

While he waited for his drink, he tried to remember. He had a brief flashback on the coach, of Lauren begging everyone to fill in some survey. Somehow, despite the fact he was pissed, he worked out this was a Margaret thing. So he suggested they all rebooked to prove better than any survey that they had enjoyed the night. A few people were going home, but the others bought up any spares. He closed his eyes, thinking hurt, so he tried to relax and prayed once again for his hang over to pass.

He did smile though. He was too old and clever to make the same mistakes again. Leo old boy he told himself, there is no point getting older, if you don't get smarter.

So, on the second night out he was still the life and soul of the party. He still organised drinking games, mostly new ones, and got the group having a great time, but he managed his alcohol intake skilfully. Missing out on a number of rounds, so by the time it was getting near to leaving for the nightclubs he was still sober. Someone announced that should play truth or dare and everyone agreed enthusiastically. Lauren and Leo took a back seat and let the guests arrange themselves into the two groups that basically they had come as. The two games went back and forth, with righteous laughter all round, as people performed dares, told truths about themselves or picked up forfeits. Suddenly there was a bit of chatter and both group's bottles were placed facing Leo.

"Truth or dare," they all shouted to him. Leo hesitated and went for the truth option. So they asked him how many women he had slept with. Pretty much all the truths or the dares had a sexual connotation and so that was why Leo went for truth. However, he was forced to hesitate over the answer before he told the group "three." They howled with protest, and told him he was not telling the truth, and he had to pay a forfeit.

In order to validate this one of them held up a picture and profile of Leo Wood. The piece of paper left everyone in no doubt that he was, or as it turned out had been a porn star and a very successful one at that. This had been exactly why he had been reluctant to help Lauren. He dreaded all the attention and questions when people knew what he had been. Often it was just natural curiosity, but he still hated it.

However, after holding out the proof they all roared with laughter and told him not to worry about it. It seemed in his drunken state the week before; he had told them all that he had been a top porn star. They had doubted him, but someone had checked it out. So all of them, even Lauren knew. They all thought it was great fun and told him not to worry about it. However, there was no way he had therefore only slept with three women, Lauren laughed and said it was probably more like three hundred, and again the group roared. Even Leo now joined in and began to relax again.

However, there was no way he was not going to pay his forfeit. Lauren complained she had not had a turn. Someone yelled that maybe Leo should have to do whatever Lauren wanted. The group yelled yes and so that was it. Leo awaited his fate with trepidation. Lauren decided his punishment could wait because it was to dance with her. Apparently he had protested last time that he did not dance. Yes, everyone roared again, that was perfect. Leo groaned inside.

At least they had not made it a porn related forfeit. That had been his real fear. All too soon they were in the first nightclub. He watched the others dancing and chatted easily with those that were taking a rest from being on the floor. The others were all couples, so Lauren regularly dragged Leo onto the floor to dance. Slowly he began to feel less nervous about dancing and began to quite like it. Soon they moved onto the second nightclub, and after more dancing they all gathered at the bar for shots. Suddenly, the lights went down and slow music started.

Lauren dragged Leo onto the floor, "yelling forfeit time," and draped her arms around his shoulders, she rested her head on his shoulders and they began to slowly move together.

"I thought I had paid my forfeit already," laughed Leo in Lauren ear.

"Nooooooo, not yet," she whispered back in a low, almost seductive tone.

"This is so nice," she added, as they moved around the floor together. During the dance Lauren told him she did not know why he hated dancing, he was really very good, and then suddenly it was over. The music stopped and DJ announced it was time for everyone to kiss his or her partner goodnight.

Lauren took one step back, and dropped her head shyly. It was an awkward moment and Leo knew he had to do something. In the very dim light Lauren raised her head, and Leo placed his hand on the side of her cheek. However, it was Lauren who was the one to reach forward and kiss Leo. Their mouths instantly locked in a passionate embrace. Lauren was forced to stand on tiptoes to reach him; silently wishing she had put some heels on. The kiss went on and on, Leo changed the angle of his head a couple of times, but still their lips eagerly explored each other's mouths. Finally as Lauren hand hovered at the side of Leo's face their mouths parted, but their heads stayed so close, they were almost still touching.

"I thought you wouldn't want to," said Lauren, a little breathlessly.

"I thought the same," replied Leo awkwardly. She thought it great that despite his past he could still feel unsure what to do. Their foreheads moved together as slowly the lights came up. They smiled and looked up at the lights. "I guess we better get the gang home," said Leo, and Lauren nodded.

Part three

Leo stumbled tiredly into his villa the last one to be dropped off. This was his punishment apparently for the week before, when not only did he have to be dropped off first, but also everyone had to wait whilst keys to his villa were picked up from reception, and then he was put to bed. Everyone in the group had been great, so he really did not mind, although he had been sad to see Lauren get off at the first stop. He had no idea why, when it was not near where her apartment was. As he wandered into the lounge he thought he heard a noise and so immediately wandered through into the bedroom. Sitting on the bed looking nervously at him was Lauren.

"I hope you don't mind, I grabbed a quick shower," she said. She was now dressed in only a tee shirt and knickers. "Sit here," she said, and so Leo obeyed and sat on the bed beside her and she immediately put her arm around him. The two of them gently caressed each other's back.

"Are you sure this is a good idea?" He asked and she immediately nodded. "Do you want me to take a shower too?" He added.

"No, its okay," she said and she reached forward to kiss him. The first kiss was a brief peck, followed by another. They continued to kiss each other, their mouths touching and parting rapidly, as Leo stroked Lauren stomach, and then cautiously reached up to touch her breasts. "We could turn a lights down a bit," she suddenly said. Leo smiled and got up. Lauren sat still watching him, an arm defensively placed across her chest, as he dimmed the lights.

"I was worried you wouldn't want me," she said. He replied that he had been so disappointed when she had got off the coach at the first stop. "That's good," she said quietly.

As he returned to her side, she told him that was better and now she reached forward properly, arms round his shoulders and they kissed much more passionately. Like they had in the nightclub. Leo's hand rubbing and squeezing Lauren's tits as they kissed. Leo's head moved to her neck and he kissed her there, holding the other side of her head with his hand.

"Mmmmmm," whispered Lauren. "That feels so nice." Leo buried his head into her shoulders and then slowly his lips reached hers again and they kissed. Leo's hand placed gently around her neck to hold her head in place. Meanwhile Lauren's was pushing his head into hers.

When they paused kissing. A quizzical look crossed Leo's face.

"How the hell did you get in here?" He asked, suddenly realising she had somehow got into his villa.

"Oh, a taxi and the key from last week," she laughed. "I kept it hoping I might find another use for it."

Leo looked down, and his hand found its way under her tee shirt, cupping and squeezing her right breast as it reached up inside. Lauren helped him to lift her tee shirt, revealing a pair of small, but wonderful breasts.

"Do I have nice tits?" She asked and Leo told her they were lovely. When she uncovered her left breast, he briefly touched it, before taking it in his mouth.

"Very lovely," he said, in a dreamy voice, just before he took her nipple into his mouth.

"Kiss me," begged Lauren and so Leo reached up and they resumed passionately kissing again, all the time his hand was rubbing her breasts. When once again their mouths parted, Lauren asked nervously if she should take her tee shirt off and Leo nodded. So as he rested his hand on her chest she lifted up her arms and removed her shirt. "Your turn," she said and she helped Leo undo the buttons of his shirt and remove it. Her hand nervously touched her mouth, as she told him he had a wonderful body and she reached out to touch his chest. His body felt so hard and firm, as she eagerly kissed and nuzzled his neck. Suddenly, she licked him, giggled and asked if he liked that. He breathed out heavily and smiled. Lauren concluded that was a yes. So she did it again.

Leo's chest rose and fell slowly again as he reached down to gently lick and caress her nipple with his tongue, making Lauren lean back and support herself with her hands, as she occasionally kissed his shoulder.

"Oh," she quietly moaned, as his tongue made her nipple come alive. He swapped breasts and she moaned again, as immediately she felt the same wonderful sensation. Slowly her hand reached out and touched his leg and then the bulge in his trousers. His cock felt hard and very large.

He kissed her again. "Are you ok?" He asked and she smiled.

"I feel wonderful," she said. He was rubbing the back of her neck now and it felt great. "That's lovely," she murmured. So he got her laying on her front on the bed and then sat across her legs. He began to rub her neck, getting immediately sounds of approval from Lauren. Gently he worked on the muscles of her neck, occasionally she raised her head, but mostly she laid it on the bed, loving the massage she was getting. Gradually his hand went lower and then eventually it found its way inside her knickers.

"Take them off if you want to," she said. So he jumped off her for a moment, removed them and then sat across her again. Rubbing now her neck, back and ass, he continued to massage her, before lowering himself he kissed her neck and face. Lauren smiled; raising her head to receive his lips, before flopping back down again. Finally he kissed her ass, making her laugh and kick her legs before he resumed his massage.

"Is that ok?" he asked. "Not too hard?"

"Its lovely," she said. She closed her eyes and kept still for a while before quietly adding in a wistful tone. "I am so horny."