Pushing the Limits Ch. 05 - Villa

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Holiday in the sun, and all of the family are invited.
7.2k words
4.62
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Part 5 of the 6 part series

Updated 06/10/2023
Created 04/10/2021
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This is the fifth part of a multi genre series, with each part designed to work as a standalone piece. The story centres on Mark, his wife Jean, their family, and friends.

In Part 1, Mark had an unexpected and slightly awkward sexual encounter with his sister.

Part 2 was a crossdressing story, with Mark becoming Maria xx, and by coincidence he ends up seducing Elaine's husband Richard.

We caught up with Jean in Part 3, a lesbian sex story, when she visited her friend Rebecca and together they explored their bisexuality.

The threads started to come together in Part 4, which straddled crossdressing, lesbianism and loving wives as Jean and Rebecca go to a gay club that Maria xx also happens to visit on the same night.

At the end of Part 4 we learn that Jean has won a holiday in Spain for up to ten people and that is where we pick the story up.

This part deals with the start of the holiday only, there is more to come. It features straight sex, lesbian sex and anal, but mostly it's about family. Enjoy.

***************************************

It was a pleasant position for the couple to be in, but a difficult one all the same. Who to invite to stay in the Spanish Villa?

"It's your prize so you get to choose," offered Mark generously, "If you just want to invite your friends that is fine."

"I mentioned it to Rebecca, but she is planning to visit Alex in London that week," Jean explained.

"Why not invite them both?" Mark wondered.

"Alex can't take the time off," Jean replied.

"What about your other friends?"

"Who? Laura and Fiona are work colleagues, if I'm taking time off, they can't. Who else is there?" Jean was beginning to feel a bit sorry for herself.

"Well, there's always your parents, and your brother wherever he is," Mark persisted.

"I'll ask them, but it really isn't their thing, they won't be interested, trust me. Andy? I don't know where he is now. I'll send him a message, but don't expect a response." Jean sounded quite despondent for somebody who had won a dream holiday. "Of course, we will have to bring Elaine."

Mark was suddenly nervous. He had never told Jean about his sexual encounter with his sister and wasn't sure that two weeks sharing a house with her was a clever idea in the circumstances.

"Elaine are you sure?" offered Mark eventually.

"She's your sister Mark!" Jean was surprised at his reaction.

"Well, if you're asking Elaine you have to ask Richard." Mark explained.

"Yeah, so?" Jean was non plussed.

"And their two kids." Mark continued.

"Of course," said Jean.

"And Elaine will want Mom to come too, to mind the kids. And you can't ask Elaine and not ask Kyra," Mark referred to his younger sister, "She'll definitely accept, God knows when she'll turn up though."

"What's wrong with that?" Jean asked.

"That's six members of my family Jean. and with us two, that's eight. We might as well ask my father while we are at it. You only have ten tickets Jean."

"Well, we don't have many other people. How about we call up to Elaine and Richard now and break the good news?" Jean was sounding more positive again.

Mark hadn't been face to face with his sister for weeks - not since their impromptu sex. Since then, he and Jean had agreed that they were okay with each other having sexual encounters with others, but it was far from clear whether that included family members. However, to protest too much would only raise questions, so he went along to Elaine's.

*************************************

Looking out the bedroom window Elaine could see Mark and Jean's car coming up the driveway. The past two weeks had been whirlwind of thoughts and emotions in an experience of absolute normality.

Her drunken sex with Mark, when it happened, seemed world changing. She had cheated on her husband, broken an infamous taboo, possibly even broken the law. Right in the moment it seemed as if nothing could ever be the same again. But within minutes of her own brother pumping cum deep inside her, she was sucked back into reality.

Elaine spent the remainder of that night trying to get a one-year-old child back to sleep. She had little more than an hour's sleep herself before her husband Richard got back from his night shift, and she was up again. The next two weeks followed the same pattern, her time spent serving others with no time to herself.

As for Mark, she had barely heard from him since. She had tried to put the incident out of her mind, but it was impossible. For all the awkwardness of their encounter, despite the drunkenness, the abrupt ending, it excited. Maybe it was the touch of a different man, maybe it was the perverse excitement of taboo, but whatever it was she craved more.

But there was also the guilt. Not for Richard - Elaine was no fool, she knew he was probably screwing around, but for Jean. Since she married Mark, Jean had become the closest thing Elaine had to a best friend. And yet she had fucked, arguably even seduced Jean's husband, and Elaine did not know if that feeling of guilt would ever dissipate.

Just then, the thought occurred, what if this is a confrontation? What if Mark confessed to Jean and now, she was dragging him up to her house to ruin their lives. She was frozen in thought until the doorbell rang. "Richard, will you get that, I will be down in a minute?" She bellowed down the stairs.

Richard was stretched out on the sofa as the bell rang and let out a childish groan as he got to his feet, as if answering the door was the biggest task ever encountered. He opened the front door to be met with Jean and a rather sheepish looking Mark. Richard was wearing an old t-shirt and a pair of cargo shorts, but he was barely out dressed by Mark and Jean (not that Richard would have cared); Mark wearing a slim fitting tracksuit and Jean wearing... Jeans... and a tight-fitting red jumper made of thin material.

"Hi Richard," said Mark meekly, this was also their first meeting since that night in the hotel.

"Do you mind if we come in?" Jean asked but did not wait for an answer and brushed straight by Richard. "We need to talk to both of you about something."

Richard noticed Jean's ample chest bounce as she walked, surmising that the voluptuous auburn-haired woman was not wearing any bra, but quickly these thoughts were replaced by worry. Had Jean found out about him fucking Mark's alter ego Maria xx? What else does she know? Does she know about the prostitutes? The babysitter who never came back? The cleaning lady at work? He could be in serious trouble.

Jean went straight into the kitchen and Mark followed several steps behind. As he passed his brother-in-law, Richard tapped him on the shoulder and glared at him as if to ask, "Does she know?"

Mark returned the stare and shook his head vigorously.

Feeling relieved Richard shouted up the stairs: "It's Mark and Jean, we're in the kitchen, Jean wants a word!"

That did nothing to ease Elaine's concerns. She could not hide from it forever. Could she? No of course not. If this was what she feared, then it was time to face the music.

Jean turned as she heard footsteps coming down the stairs. She saw a pair slim perfectly sculpted legs in a pair of transparent black tights, topped off with the hem of a maroon skirt, descending. Noting an apparent confusion, concern even, in her sister in law's face as she entered the room, Jean beamed a smile at Elaine to put her at ease.

"Hey Jeanie, how did you get on with your friend in Bangor?" Elaine asked, shaking off her nerves.

"Rebecca? Well, it was a bit tough at first, but she is in a much better place now. We even had some fun," Jean answered.

Mark giggled to himself knowing exactly the fun she spoke of.

Elaine raised an eyebrow," Oh really, you are a particularly good friend to her, you'll have to tell me all about it."

Jean smiled back "I will."

Mark wondered, and worried, 'do women tell each other everything?'

Jean continued, "and I would do the same for you sweetie," she reached out and briefly held Elaine's hand.

Mark's mind wandered briefly as he pictured his wife and his sister together in a Lesbian entanglement, but then he remembered his situation. The three people with him at the table were the last three people he had sex with, and none of them knew about the other - not that Elaine or Richard would be shocked about him having sex with his own wife, however the circumstances were, a bit different.

Jean for her part was excited to break the news. It would be great for Elaine to get away. And herself and Mark would enjoy exploring their fetishes in the sun. Then she thought 'Wait, is Richard staring at my boobs?'

Elaine noticed that her brother was avoiding eye contact, but was buoyed by Jean's positivity and thought, 'Christ above, Richard is staring at Jean's boobs!'

Richard, for his part, was not really listening, he was just looking at Jean's boobs.

"So do you guys have any holiday plans made?" Jean set about explaining the purpose of their visit. She told them all about the Villa, the competition, all the arrangements, and though she could feel there was some uneasiness between Elaine and Mark, she was delighted when they accepted?

"Do you think we could invite Mom? She hasn't had a holiday in ages, and, you know, I'm sure she'd miss her grandkids." Elaine asked, and for the first time Mark addressed her directly:

"You mean she'd miss the chance to babysit them!" He interjected

"Such a cynical little bollocks!" Elaine scoffed. "But I'm sure she could help out too," she smiled.

With that quick exchange some of the tension seemed to lift. Elaine was relieved to see that she was back to exchanging playful insults with her brother - the way it should be.

"Don't worry I have her on my list, but we will all help out, even Kyra." Jean assured Elaine.

"Kyra is coming? Don't be shocked if she lands with a new boyfriend, probably a mountaineer from Norway who brews craft beer and plays the lute," Elaine joked. She could be mean about her 22-year-old younger sister, but in truth it was probably just jealousy.

"Or a Moroccan iron monger who sells expensive homemade yoghurt from a caravan in a swanky London suburb," Mark added.

"Yes, she's coming, though she said she might arrive a little late." Jean answered.

"Sounds about right," Elaine laughed.

"You're all welcome, I even told Mark to say it to your father," Jean spoke positively but immediately noted a cool reaction from Elaine.

The siblings stared at each other. "I'm not sure that is a good idea, he is always travelling about, besides, I don't know how Mom would feel about it," said Elaine.

"I had the same thought," Mark explained, "but I texted him two days ago to see if he wanted to chat, and there's been no reply, so the chances of him coming are between slim and none."

Elaine was relieved. Her relationship with her father was not bad, but she was closer to her mother ever since they separated ten years ago. She did not remember the breakup being particularly acrimonious, but she knew they had not spoken in years, and her desire to protect her mother was stronger than her desire not to hurt her father's feelings.

They chatted some more about holiday plans before Mark and Jean returned home. The ice breaking conversation had relaxed Mark somewhat, but he left knowing that his attraction to his sister had only grown, and deep down he knew that the truth about his sexual experiences would soon be unveiled.

*****************************************

A striking middle-aged woman with shoulder length blonde hair and a figure that defied her years emerged at an airplane door on the runway of Malaga airport. She wore a red, floral pattern, low cut maxi dress with thin straps baring her mature but firm cleavage to the hot sun. A blast of warm air blows her dress to thigh height as she calmly puts on a pair of sunglasses.

The light, the heat, the flavour of the Mediterranean, the dry rocky hills. Instantly, Mary was taken back to a time before children or grandchildren. It was before the joys of marriage and the heartbreak of divorce. She and her then boyfriend, now ex-husband, Leo, travelled Spain on a shoestring budget, enjoying the wine, the food, the passion of Iberia. It was a time of innocence, adventure, and love. There were no flights or luxury villas back then. They travelled by bus, stayed in hostels, even camped outdoors, but the thriftiness only enriched the experience.

With the pain of their breakup Mary had blocked out so many memories, but not that one.

That momentary romantic recollection, tinged with a hint of melancholy, was pierced by the voice of her daughter Elaine, quickly following her from behind.

"Careful on the steps now! Jean, do you mind?" Elaine was struggling to corral her two children and all their extra luggage. She was followed by Jean and Mark, who stepped in to share her load. Last off the plane was Richard who having taken ages to locate his carry-on case, finally came down the steps in a hurry then sprinted past his companions towards the terminal.

"What's up with him?" asked a perplexed Mary.

Elaine was too preoccupied to hear her, and Mark only laughed. Jean offered an explanation; "I think he had a few beverages on the plane, and maybe forgot to use the facilities before the seatbelt light came on," she rather kindly put it.

Jean was their de facto tour leader. She had the details of their hire car, an 8-seater Seat Alhambra, and took responsibility for the driving. Richard had bragged about how he had driven all over the continent and now that they had landed, he was keen to display his expertise. Elaine quickly put an end to that notion, much to the relief of the rest of the party, pointing out that Spanish police were zero tolerance when it came to drink driving.

Jean followed the directions on the satnav, and their route drew a mixture of reactions from her passengers. "Hmm," was the only noise Mary made as they neared their destination and found themselves driving along the main strip of Torremolinos and Benalmadena. It is fair to say that the endless line of dodgy nightclubs, monstrous concrete high-rise hotels and English "pie and mash" pubs were far from what she had hoped for.

Richard on the other hand could not conceal his excitement on seeing lines of scantily clad young women making their way from the beach. At one point he whistled with excitement, but it was not clear if the target was a bunch of twenty something year old women outside a bar or the sign beside them offering pints of San Miguel for €1.

Soon though they were taking a right turn and climbing the hills that rise above the strip and overlook the coast. This was a higher class of neighbourhood with gated communities and extensive private Villas.

"Here we are, hope you have fun!" Jean said as she pulled up to a large wooden gate. She dialled a number into her phone and the gate slid open, revealing the Villa.

It was a traditional white building with a red terracotta roof and elaborate Andalusian tiles decorating various surfaces throughout. It had an open plan kitchen/diner/living room and five bedrooms. Opening out from the living area was a south facing terrace with a barbeque area, and a pool.

The holidaymakers took a moment to soak in the view over the red rooftops of the houses below which ran down to the to shore. From there they could see the turquoise waters of the Mediterranean, the ships passing along the coast, and in the distance, across the straits of Gibraltar, the Atlas Mountains - Africa.

The searing heat was exaggerated by high humidity. It was a sweaty day, and everyone had built a thirst.

'Pop!' they were stirred from their gaze and turned to see Richard filling glasses from a bottle of Cava. This time though they joined him, exchanging glances as they clinked their drinks.

*************************

The first night of the holidays ended early for Richard. By Sunset, Elaine was guiding him to their en-suite bedroom, fearful that he would stumble on the tiled stairs. Mary was putting the children to bed, leaving Mark and Jean alone on the terrace.

The sun had now dipped below the hills and the evening glow soon gave way to a moonless darkness, punctuated by the lights of the town below and of ships on the calm sea. Then, a flash. Lightning illuminated the Mediterranean sky, the flash reflecting on the sea below and illuminating the Atlas Mountains.

"Come see this, Mark invited Jean, "it's stunning."

With a glass of Rioja Reserva in one hand, Jean slipped off her shoes and joined Mark on the two-seater outdoor sofa, lifting her legs onto Mark's lap and leaning back onto the armrest. Mark's hand rested on his wife's bare leg, just below the knee as they sipped their drinks and breathed in the still warm night air.

Mark fixed his eyes on the hem of Jean's short summer dress which had ridden up to the top of her thighs. Immediately he recognised a line of blue lace, and he knew that she was wearing her blue underwear. As his eyes drifted upwards to the visible side of her beautiful breasts, he felt his cock start to stiffen. Jean felt this too, the unmistakable feel of a hard penis pressing into her leg. She knew what Mark was thinking, and she thought it too.

As thunder rumbled, Jean reached down to place her glass on the ground then leaned forward to meet Mark's lips with her own. As she did, Mark let his hand slip under her dress, under her panties and grasp a cheek of his wife's smooth round bum. Jean tugged at his shirt to open the buttons and they lashed their tongues together, with the passion and desire of two desperate lovers who had not seen each other in years.

Another flash of lightning, and Mark could see a single bead of sweat slide down the cleavage of his wife's breast. He placed one hand inside the top of the dress quickly baring her breast then planted his mouth on her swelling pink areola. Mark's suction of her breasts made Jean's crotch dampen. She toed at the waistline of his shorts, she needed him inside her.

Mark was ready to oblige Jean, he began to shuffle off his shorts when suddenly, another flash, and Jean jumped, then pushed back away from her husband. He looked up in confusion to see an expression of shock on her face, her mouth open, her eyes widened, "What is it?" he asked, genuinely perplexed.

The lightening had been enough to illuminate Jean's surroundings, enough for her to see Mary stood opposite her against the railing, glaring down at them attentively.

"Just me darling." Mark turned around to see his mother looking down at him. "So sorry, I came out here to join you..." she paused, "for a drink, I did not realise you were busy," she explained.

"Mary, I'm so sorry, I thought you were in bed," Jean offered, noting that her mother in law's eyes were on her. Jean realised that her breast was still bare, and Mary could probably she her wet panties. Jean adjusted herself.

"What do you take me for, I'm not that old," she said wryly, "besides, you still haven't shown me where my room is."

Embarrassed, but still catching her breath after her arousal, Jean offered "I'll show you. I hope we didn't shock you; we will be more careful in future."

"Nonsense!" said Mary. "You should enjoy yourselves, and anyway it was nice to see two bodies in the throes of passion, I don't see much of that these days."

"Mom!" Mark was aghast.

"Oh, don't flatter yourself honey!" Mary mocked, and as she did so her eyes met Jean's. The sexy auburn-haired woman returned a cheeky smile.

Jean got up off the chair, fixed her dress and said, "Come on, I'll show you where you are staying."

Mark watched his voluptuous wife lead his mother through the glass doors, and as they vanished inside his sister Elaine emerged through the kitchen door, barefooted, wearing only a light nightdress which exposed her legs to the tops of her legs. "Where are they off too?" she asked.