A Sisters' Ploy Ch. 04

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Lucy loses her virginity.
10.8k words
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Part 4 of the 9 part series

Updated 06/16/2023
Created 03/20/2022
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Kylie spent the next few days pondering the hole she had helped dig herself into.

Having Matt take Lucy out on a date and getting her slightly pissed seemed to be a good way of getting her in the mood for more intimate sexual relations, as well as giving her dating experiences she'd never had before. She didn't begrudge Lucy that. With all the hang ups she was dealing with, she needed something like that if she was ever going to fulfil her ambition of being more relationship worthy by being accepting of the sexual side of things.

But with the current pattern of Matt visiting twice a week, and the whole date and sex thing with Lucy occupying all the available time on a midweek, workday night, Kylie had been squeezed out of what she came to realise was a desperately wanted mid-week sexual liaison of her own.

She might have got away with an early morning encounter the first week, but while it was physically satisfying, the time urgency of it wasn't emotionally fulfilling. And it couldn't be relied on as a repeatable pattern.

She could ask Matt to make it three nights a week, instead of two, but Kylie was starting to want a lot more. In a way, their current arrangement with Matt was a somewhat unusual form of 'friends with benefits'.

One where he went through the sexually frustrating process of slowly developing Lucy's interest in and ability to deal with sex, while she provided the sexual outlet to his sexual needs -- satisfying her own at the same time.

But Kylie wanted to move it to one more based on real relationships. She might have preferred to talk more in terms of a loving relationship; but wasn't yet sure how that would go down. Kylie had normal sexual and romantic desires. She always had. But at the same time, she and her less sex and relationship orientated sister were incredibly close. Kylie had followed Lucy into an accounting career and they'd both moved to Sydney from their native Melbourne together. They were each other's' best friends and most constant companions.

Sharing a household just seemed natural. But where it all feel apart was with Kylie's boyfriends. Lucy always hated and resented them. Kylie had to admit, for the most part they were beneath Kylie's grade. But in Mona Vale, surfing dropouts where somewhat in the majority in the circles they moved in. Kylie had found herself having to take what she could find. You know what they say about loving the one you're with...

Which is where Matt seemed to offer a solution. One Lucy hopefully wouldn't resent if they managed to work out how to share him.

For her more immediate agenda, the ace up Kylie's sleeve was her knowledge that, since his breakup with his previous partner, Matt was missing a more permanent residence. He was crashing in with a friend, but it wasn't suitable as a longer term arrangement.

Kylie wondered whether he was ready to move in with her and Lucy. There wasn't a spare bedroom. It would be a matter of sharing one of their beds. Or taking turns between them. That would be a detail that would have to be worked out; but Kylie felt she would be quite happy to have Matt occupy her bed. Indeed, given the sexual desires he generated in her, more than happy.

Why he generated such strong sexual desires and whether they were a solid grounding for a relationship was something she was grappling with.

Since Kylie had got to know him as a friend of her sisters, initially it was lust; pure and simple. His tall, slim, strong, athletic body, fully on display as he sat on duty in the lifesavers' tent, had more than piqued her interest. It had driven her to frustrated distraction.

His ability to give her orgasms in a way no other male had come close to doing reinforced something in her desire for him.

Whether it was lust, or now something more fulfilling, was what she was trying to work out. Matt displayed a gentle kindness and generosity that Kylie found rare in men. He'd stayed friends with Lucy, even though there had been times she'd gone suddenly and inexcusably feral on him. That was something Lucy was prone to doing and not many had showed the same understanding and it counted for a lot in Kylie's eyes. He seemed to try and understand her better than most people, and Kylie admired him for that too.

In the meantime Kylie had to work out with Lucy what Lucy's objectives were to be for Saturday. Given the way Lucy finished with having Matt penetrate her on Wednesday, it might be time for a full on cowgirl approach. At least that way Lucy would get to completely control things.

But as both Kylie and Lucy -- and indeed Matt -- were fully aware, Lucy can start out with these objectives and find herself unable to complete them on the night. That's the nice thing the girls liked about Matt. He accepts Lucy is testing her limits and as being completely in control, whether or not she follows through with the objectives she describes to him at the start.

Matt wasn't stupid. Much of this he'd already worked out. He'd recognised that Kylie had missed out on Wednesday night and there was a need to rethink the pattern of their engagements. He'd recognised that Lucy's next step might well be proper penetrative sex and that getting her slightly pissed might help that too.

But he'd also recognised that the best place to talk about this, and so many of the other issues that swirled around what was happening was over a group dinner -- or at least some communal gathering that was relaxed and not too time constrained. Which sort of conflicted with any 'date before sex' arrangement with Lucy on Saturday night.

In the end, he sent the girls the following text...

"There seems to be a lot to talk about. How about I take you both out to dinner Friday night to give us a chance to chat? Only thing is we need to find somewhere private enough to let us talk openly."

He'd chosen text because it was the only way he could communicate with both of them at the same time.

While the girls accepted the concept, it was difficult to find a place that offered enough conversational privacy. So the arrangement became one of a poolside BBQ at the girls' place; with Kylie making it clear he should bring his swimmers.

When Matt rocked up to their place around 6pm, dressed as ordered in his boardies and a t shirt, the door was answered by Kylie, dressed in nothing more than one of her rather small bikinis. She walked him through the house to the back yard where Lucy was. To Matt's surprise, Lucy was also dressed in the tiny black bikini, donated to her by her sister, which had become known as her sex bikini, because it had been used to finger Lucy to climaxes before she had overcome the crippling sense of modesty that prevented her from stripping naked for sex.

It had been clear to Matt from the first time Lucy wore it that she'd found it inadequate to let her feel comfortable with the amount of exposure. It was still not something she'd wear to the beach. But in the company of Matt and Kylie, she'd sort of acclimatised to it, now able to wear it with some degree of confidence.

Keen to get Matt undressed to get the full benefit of the visual stimulation Matt's body offered her, Kylie suggested they start with a cooling swim before getting the BBQ on the way; helping Matt take off his shirt. As she put the shirt over a nearby chair in the house, Kylie placed a hand on the cheek of his bottom, seeming to guide him back outside. But she moved her hand around on it a bit; not really rubbing it, more like she was exploring it.

Which proved to be the case as she asked...

"Have you got speedos on underneath?"

"Yea, why?"

Kylie instantly faced him, standing close as she undid the drawstring on the boardies...

"Well, you won't need these then."

She loosened the waistband and let them fall to his ankles before bending them down to strip them off his feet, having a good perve at the bulge of his manhood in the thin, revealing material of his swim briefs. That was a much more satisfactory presentation as far as Kylie was concerned; one that offered endless possibilities of visual and sensory pleasure, even before she fulfilled her intention of getting Matt to bed at the end of the evening.

But the cooling swim turned out to be a subterfuge. Kylie didn't really want to spend the evening in wet swimmers. Instead she diverted him into have a chat with her and Lucy by the pool's edge, with just their feet hanging in the water; arranging for Matt to sit between the two girls.

Matt sat with his arms spread out behind him, leaving a respectful distance between them as he sat next to Lucy, with his arm on her side further back so as not to risk contact. Kylie as she sat down had no such inhibitions, sitting in close contact with Matt from her shoulder to her knee, her hand once again resting on Matt's thigh, her back brought against the arm he had behind her, encouraging him to wrap it around her.

It was what she had missed so much about Wednesday night. Unlike her sister, she was a tactile person. A quickie in the morning had been better than nothing, but there was a world of physical interaction that Kylie had felt left out of.

There was much to talk about. Kylie had a mental agenda for the discussion, but she had to get things in the right order. So for her, the first was to bring up Lucy's objectives for the following night. These she'd already discussed with Lucy, so she encouraged Lucy to set them out for Matt.

As expected, it was to experiment with penetrative sex, cowgirl style. Everyone understood that was in order to give Lucy maximum control over proceedings. And yes, a date night with Lucy beforehand seemed like a good idea too.

Matt took the opportunity to explore just what had happened on the previous evening as Lucy surprised him by pushing his manhood into her body at the moment of her -- and as it turned out, his - climax. It was the last thing Matt had expected. Was it physically or emotionally uncomfortable? Was Matt cumming inside her problematic? Is penetrative sex of itself not such a big issue for Lucy?

The questions were put gently, but also in the knowledge that, for the most part, Lucy had few inhibitions about revealing what to others might be highly personal information.

Lucy told him that it just seemed right at the moment. For all her concerns about safe distances and lack of contact, once she had gone that far with Matt, the act of penetration didn't trigger her. She explained that, in fingering her, knowing that Matt had sometimes had three fingers inside her gave her some reassurance that her body would accept his shaft without too much discomfort. It had been tight but not painful, and felt it might even have enhanced her own orgasm.

So she felt it was time for an attempt at proper penetrative sex. But she added that being a bit tipsy had made it easier for her to overcome her inhibitions, so she appreciated Matt's offer of a date beforehand.

That let Kylie acknowledge that, while it was important for Lucy to get some experience of sleeping with a man, the date night arrangement really didn't leave any time for Matt to spend with Kylie; raising the question of whether he'd like to spend more nights with them; maybe even move in.

The additional nights, Matt had expected. The moving in caught him by surprise...

"You don't have a spare room."

"I know, you'd have to sleep in our beds."

"Is that going to cause you problems?"

"What it might mean is you don't get to sleep in the same bed every night. There would be some taking of turns. Lucy isn't sure she'd want every second night, but you'd have a welcome home in my bed any time she wasn't up for it. So I suppose the real question would be whether taking turns in different beds would be a problem for you?"

Matt knew the answer to that question was no, it wasn't a problem. Both beds were quite comfortable, even if the behaviour of their other occupant was complete opposites. He wasn't adverse to Kylie's desire to cuddle, but nor was he concerned about Lucy's desire for distance. But the real issue for him was whether the girls were willing to go deeper into what was already a complicated arrangement...

"It's not a problem for me, but I do want to make sure it's not a cause of friction between you."

Matt looked to Lucy, wanting to have some expression of her view, without it being filtered through her more outspoken sister...

"No, we've talked about it at length. We think it might actually be a good way of reducing the friction that has arisen in the past with Kylie's boyfriends."

Matt noted the use of the word boyfriends. The status of their relationship at that moment defied any single word, other than maybe 'complicated'. Living together, sharing beds and sex, was not usually the sign of being mere friends.

Was he about to become the boyfriend of two sisters at the same time? Was he to become Kylie's boyfriend while simply training Lucy in sex? Was all this a prelude to an expectation that Lucy would now be able to find a boyfriend and bring him into the house too? Or would Matt be transferred to Lucy's possession -- because after all he'd had a long friendship with her -- letting Kylie repartner with someone else?

The simple fact was, he liked both girls. He still doubted whether Lucy could ever hold together a long term romantic and sexual relationship. She had also expressed to him in the past a complete lack of interest in being a mother; something that his observation of her almost disdainful interaction with kids told him was more than a superficially held view. And she was aware of his desire to be a father. So he certainly didn't view her as a long term relationship person for him. Kylie on the other had had many of Lucy's better characteristics (and let face it, beauty), without the same problems.

But it wasn't as though he had to give up a nice tenancy or house to accept their offer. The fact was he desperately needed somewhere to live. Such furniture as he had was already in storage and he was presently living out of suitcases. He had nothing to lose except Lucy's friendship and while he valued that, his instinct was it would bring her closer, rather than draw them apart, whatever became of the arrangement long term.

It seemed worth the risk...

"OK then, when would you like it to start?"

Kylie had an answer to that ready...

"Well, you're staying tonight. Why don't you collect your stuff tomorrow?"

From the time of the discussion on Lucy having penetrated herself with Matt's shaft as she came on Wednesday night, Kylie's hand had been slid up Matt's thigh far enough for the back of her fingers to be in contact with the bulge in his speedos caused by his manhood. It was by now Kylie's standard move when she sat next to Matt.

It had stayed there though all the subsequent discussions. But her fingers had never been still. There was something Kylie found quite sensuous about rubbing her fingers on the soft slippery material of his swimwear, feeling his manhood harden and extend underneath, stretching out the material, and then pausing to let it shrink again; never really going soft, because her fingers always maintained some contact with his ball sack.

Matt never really objected to what she was doing, even though it sometimes left him, mid conversation, with a ranging erection weeping pre-cum through his swimmers. Why would he? It wasn't an unpleasant experience -- quite the opposite -- and given he knew how the evening would end, didn't remotely represent prick teasing. More an extended foreplay.

Lucy, sitting slightly bent forward to avoid any possibility of contact with Matt's arm, was well aware of what was happening. Her eyes, as she turned to Matt, often sinking downward to stare at the occasionally towering edifice stretching out his swimwear. She envied somewhat Kylie's relaxed approach to manhandling Matt's manhood. Apart from her somewhat restrained interactions with Matt, she had no previous experience of casually playing with it like that or even of just watching it grow and shrink like Kylie could induce in it.

Having again raised it to full hardened height, Kylie excused herself to get them all a drink, leaving Matt and Lucy to themselves. Matt turned the discussion to where they might go for dinner the following night; suggesting a local Thai restrauent. Lucy demurred, indicating that she didn't like spicy food, so they settled on a seafood restrauent instead, just in time for Kylie's return with three glass of red wine.

Matt noted the glasses were quite full compared to what he might pour. He also noted Lucy's was the fullest; wondering if that was just a turn of fate or intentionally done by Kylie.

He knew it was time to get up and start the BBQ. He'd been sort of waiting until his erection went down before he actually stood up; just a sense of appropriateness really. There was a brief window just before Kylie returned with the drinks when it was only half height, but he needed to finish the discussion with Lucy about dinner.

After that Kylie had fondled it back to full height again.

Matt rationalised that Kylie had caused it and Lucy had been staring at it for some time. It was pointless to pretend it wasn't there. So he excused himself as he stood up, preferring to accept the display rather than curl over his body to try and minimise or hide it.

As she sat there with her head at the height of Matt's waist, it certainly impressed Lucy.

As a lifeguard, Lucy had seen plenty of guys in speedos. They are still a common sight on Australian beaches, especially with guys over 50.

But most of the guys she'd seen had, by that age, got a fair bit of a gut overhanging the waistband. Half the time she suspected they couldn't even see their dick over it and in some cases it seemed so buried under their gut she wondered how that had sex. Regardless, the gut always made the bulge of their manhood look rather small.

Far from having a gut, Matt's torso was fully ripped. Kylie might have had her obsession about it, but Lucy hadn't failed to notice and admire it over the years; although he'd generally had board shorts on while doing lifeguard duty with her. Now the ever so slightly concave line of his stomach made the towering erection in his speedos look enormous. But even as Kylie momentarily left it alone as he first started cooking and it returned to normal, it remained as an impressive bulge compared to all the others she'd seen.

Kylie had left Lucy taking to Matt as he cooked the BBQ while she fussed about setting the outdoor coffee table for dinner, returning regularly to make sure the wine glasses were topped up. Of course, they could have gone inside to the proper dining table there. After all, the outside table was small and with only two small Ottoman chairs, wide enough to accommodate one and a half persons, sitting there left Matt and Kylie pushed hard against each other with half a bum cheek hanging off the chair.

But Kylie felt it had a nice mood about it and any small discomfort from the narrowness of the chair was more than compensated for by the tactile interaction it gave her with Matt.

The steaks and sausages on the BBQ were small but thick. By the time they were cooked, Kylie had made sure the first bottle of wine had been nearly emptied, leaving the one Matt had brought, along with all the food, ready to be opened over dinner. It had also left the three of them somewhat light headed.

The dinner itself was leisurely, full of pleasant often amusing conversation and continued to be well lubricated by Kylie's insistence on keeping the glasses full.

Matt noticed that, as the dinner went on, and she got tipsier, Kylie got increasingly frisky with him. The hand high on his thigh, rubbing his cock with the back of her fingers, became instead one wrapped around his swimmer sheathed erection. Her body, never in anything less than full contact with his side, almost seemed to meld into his, her head often resting on his shoulder.