Summer in Tuscany

Jack had a doubles match later that afternoon and afterward took his nap. Before he left for his match, he'd instructed Isabella to find a simple sun dress for Rachel in her size in town, along with his request for dinner that evening. He realized between sets, while thinking of Rachel, that he really hadn't spent much time in the same room with her since she'd arrived, other than their brief breakfasts, the group dinner, and sex. He'd given her plenty of leeway to make her own plans all day, not that he had any control over how she spent her time, but the distance between them, a detachment during the day, was their ritual.

That nagging fondness for her produced thoughts in his head about spending more time with her, wanting to know her. Truth was he barely knew anything about her, yet he liked her company. Their time together had also been restricted to the villa, and he decided that tonight at dinner he would propose some ventures off the property, into the countryside, into town, perhaps even into Florence. He'd asked Isabella to deliver the dress along with a handwritten note he'd penned on his personal stationery:

"Looking forward to dinner tonight - J."

Rachel did not nap after her poolside session. Her lemonade-induced nap had given her enough rest, and while the experience with Geoffrey and Jack and Isabella had been intense, the physical labor had been done by Geoffrey. Other than a tingling stretch in the backs of her thighs, and a not unpleasant soreness in her crotch, there was no ailments. Instead there was a buzz of energy.

Rachel had showered, journaled, looked idly and fitfully through her phone. Nearly stir-crazy, she had decided to walk to town when there had been a soft knock at her bedroom door. Her heart leaped but as the adrenaline moved through her system her mind caught up and realized that could never be the knock of Jack. She opened the door to Isabella, who silently handed her the package and note, smiling before disappearing quietly down the hall.

Rachel bit her lip, reading the note. She felt a swell of energy and emotion in her and took some time, sitting on the bed and examining the dress, to ponder it. She felt foolish at first for having some rush of emotion, like a schoolgirl at a crush, for a man like Jack. But she quickly decided that it was not the giddiness of a crush at all. She didn't even think she found Jack all that attractive. She could recognize he had some handsomeness, but his age made that seem theoretical, distant, something for a woman his age to appreciate, not Rachel.

No, the rush of excitement had to do with something which was not love or attraction but something much more base. She knew that whatever Jack had planned, it was not simply to wine and dine her. What man would woo a woman by having his friend have sex with her? She trusted that whatever Jack's plans and motives, there was something deliciously deviant about them and that scratched an itch in Rachel that had begun to burn since her time here in his villa. She could barely guess at what might happen and there was something delightful in that.

Rachel chose to go to town just the same, but was back, and showered, and dressed in the sundress, all in time for her dinner date.

---

Jack had asked Isabella to set a small table on the upper veranda, which provided a better view of the countryside, but still overlooking the pool. Champagne was chilling in an iced bucket, candles were lit, and Jack sat in one of the two chairs dressed in linen pants and a loose cotton shirt. It was ten minutes before 8. The cicadas hummed in the background, signaling the arrival of the golden hour.

He was early because he wanted to watch Rachel walk, see how her body moved. From her bedroom, she'd have to walk outside one of the side doors and down a walkway that would serve as almost a runway for Jack to admire her. At two minutes before the hour he poured the prosecco and stood, a flute stem in each hand, knowing that she would arrive promptly at 8. He felt a schoolboy nervous excited buzz waiting for her to arrive, and when the door finally opened and she pushed through, a smile lit up his face.

She was dressed only in the sundress that Jack had delivered to her, a pair of heeled leather sandals, and a golden necklace around her throat. Rachel emerged onto the patio from her room, blinking slightly in the setting sun low on the horizon. She could not see Jack up above, having to squint her eyes, and walked carefully and slowly down the metaphorical runway, her hips swaying with each step. He could see already that she had not worn a bra underneath the dress, her breasts swaying slightly under the fabric as well.

Reaching the steps to the upper veranda, Rachel glanced upwards and caught sight of Jack finally. Blushing, realizing she had been watched, she looked down carefully at her feet as she climbed the outdoor stairway, emerging in the tiny space where Isabella had set out their seats. She blushed again, approaching the table.

With the champagne bucket and tiny table, this felt like a romantic date. Rachel wondered for the first time if that was how Jack felt about this. He certainly had not treated her like any beau of hers ever had, but then again no one had ever quite wined and dined her like this either. "Beautiful evening," she said, as she sat, smoothing her dress across her thighs.

"It is indeed Rachel." He handed the the glass of prosecco to her and tilted his, tapping the glasses together. "Here's to another beautiful summer evening in Tuscany," he said, and when their eyes connected he felt a new level of intimacy, the two of them alone. "You look absolutely lovely." He openly assessed her delicate shoulders, the line of her cleavage. He meant it. The setting sun on her face, her graceful walk, the way her breasts moved in the sundress, her hips swaying, the sounds of the countryside, was, he thought, one of the most memorable 30 seconds of his life.

"I really wanted to spend some time together just the two of us, getting to know you a little better. Thank you for indulging me. Have you been enjoying your time here?" He was fully aware of the juxtaposition of the kinkiness of the early afternoon and this setting, and and image of her breasts decorated with his jism entered his brain.

Rachel was very aware of that juxtaposition. Everything in this moment was like a romantic movie, the kind she had loved watching on a Sunday evening at home, wrapped under blankets on the couch and imagining a life in the Mediterranean sun with a man who knew how to treat her like a lady. And here she was, and though the man was quite literally old enough to be her father, the rest of the moment was exactly as imagined--Tuscan sun, prosecco in beautiful stemware, a tiny table for two on a veranda, the gorgeous landscape.

And yet, they were only hours, and a dozen yards, away from her being fucked senseless by Jack's friend, and Jack himself cumming ribbons onto her naked body. That was not part of any of the movies she had watched. In Rachel's understanding a man didn't usually go from one to the other in this direction. Once you had indulged in a scene as lewd and perverted like that, things only led downhill.

Thank you for indulging me, he said, and Rachel had to smile, thinking of all the ways she had indulged him--dinner on the veranda was the least of it. He asked her about her time here and Rachel tried to really consider that, to find a truthful answer. She began immediately to blush, faced once again with the truth of the things she had done with so little prompting.

"I have to say, yes, I have, even if I'm afraid that paints me very poorly. I know that I should not have, and perhaps it would be wiser of me to pretend that I had not and to refuse this dinner and to refuse your lodging. But I think you knew the answer already. You seem to have known things about me before I even did." She cocked her head at him, wondering at his ability to either elicit these things in her or to see them deep in recesses of her character. She could not imagine how he had done either.

"I'd like to politely disagree with you on your first point. Quite to the contrary, your enjoyment of the... activities and festivities paints you in quite an exceptionally positive light in my eyes. You're bold, adventurous, intelligent, and beautiful. I'd like to think that I'm giving you a gift that you'll remember for the rest of your life. Or perhaps shape you how spend your life," he said, taking a sip. He crossed his legs, his hair-covered ankle exposed between the hem of his pants and his Tod's loafers.

"The people you've met all have those same qualities of adventure and intelligence and sensuality, though not quite as beautiful as you. Tell me exactly what you think of your experiences so far. What did you think when you realized I was watching you. Not over breakfast. I meant the cameras. You seemed to have accepted them... and perhaps enjoyed them as well? I'm a visual person. I like looking at you," he said and his eyes leisurely strolled down her breasts and waist, and he even angled his head so could look around the small table to see her thin, tan ankles.

Rachel was almost frightened by Jack's suggestion that this little vacation, this little escape into a fantasy land, might in fact shape the rest of her life. She had somehow convinced herself that there were not real consequences to what she was doing, that if she revealed herself to be some sort of pervert, some sort of slut, to these people, well, she would leave and never see them again. That allowed her to live in a place of magical freedom. But he hinted at a type of consequence that she had pushed away in her mind, tried to ignore. What if this was not just a vacation, a fantasy. What if it somehow became her life. What if she could never go back?

Yet somehow Jack made it all sound virtuous, the life of a creative, exciting person, not a dark perversion. She framed her thoughts and her answer the same way. "I was shocked, I suppose, at first. It's hard to even say anymore," she laughed.

Gazing out over the pool and beyond she pictured it in her mind, relived it. "It'd be foolish to say I only accepted them. I suppose I would think poorly of myself if I had simply let someone do such a thing. I allowed it because yes, it brought me a pleasure that was quite surprising. It must have been in me, it was immediate, to enjoy being watched. But I had never known it. I... I thought quite a bit about the fact that you were seeing me... and later that the others were, and as much as I thought I should be ashamed, I wasn't. Or the shame was part of the pleasure, like it wouldn't have been so enjoyable if I hadn't known that it was wrong somehow."

It hadn't occurred to him until that moment but he enjoyed the sound of her voice. She was clearly intelligent, and spoke with a quiet confidence, without the "upspeak" so common in women her age, and with the quiet evening as the only background noise, he listened to her timbre and the slight trace of smokiness to it.

"Do you know why I thought you might enjoyed being observed so...closely?" He asked, and when she gave her head a little shake, he continued. "I looked at your photos on Instagram and Facebook before you arrived, going back a few years. I hope you don't mind, but honestly before I gave confirmation that you could be here for the summer, I wanted to see what I was I was getting into." He took a sip of the prosecco, glanced at her tits. "And I could see that you were growing more comfortable with your body. That you went from practically hiding it, to shedding some of the layers of clothes, until you were confident enough to post photos of yourself in shorts and ultimately, a bikini. It was as if you were running some tests, gauging reactions from yourself and from others around you."

"And I think you realized that you had something. And when I saw that, that transition, that progression, I saw something in you that I thought I could...well, exploit sounds like a negative word...that I could develop further. Yes, that's better. Develop. And it seemed like a perfect fit. Your loveliness and my admitted admiration and affection for young beautiful women."

"I understand the component of shame, and it's power, and the idea of violating taboos, which for so many people is the ultimate turn on. I think the question that I'd like to explore with you for the rest of the summer, is what are your limits? And what are your buttons? As you can tell by now, I'm sure, I have very few, but everyone has limits, and I always respect them. I would never put you in any danger of any kind, or any serious risk, and I would never hurt you, unless at some point you asked me to, a spanking or something like that. And I would always comply to your "no". Always. Are you interested in exploring more?"

At that moment, Isabella appeared from the side door holding two small plates of bruschetta with tomato, basil and mozzarella. She nodded to each of them, her cleavage on display in a tight scooped neck dress. His eyes followed her as she walked away, and turned to Rachel. "She's just here to cook and serve. Tonight it's the two of us Rachel."

Rachel fell silent when Isabella approached, swallowing the words that had begun to bubble up. She waited for the older woman to serve the food and leave, and it gave Rachel a chance to digest slightly all that Jack had said to her. She had blushed when he had described in detail her photos, what he saw as he pored over pictures of her. It gave her a sort of retroactive thrill of exhibitionism to know that he had been staring at them, clearly eyeing the slow reveal of her figure, her breasts, over the years. It was the sort of perverted behavior that she would have been disgusted by to know that any man his age had been doing, or really any man she didn't personally find attractive. But now... well, now things were different.

Taboo, yes, that was the word, she thought to herself as Jack watched Isabella leave and let her know it was just the two of them. In a normal setting that might be a romantic remark, suggestive even. In their peculiar situation, it more answered the question of whether Rachel would have to watch the housekeeper service Jack sexually, or if the housekeeper would be watching them. Taboo was the thrill she felt during all these things--thrilling exactly because she never would have allowed them, or wanted them, no normal girl would. And so it was exactly the outrageousness of it that intrigued her.

"I suppose I can see that, and trust that you both have no limits and that you would respect mine. I have done a dozen things I couldn't have imagined two weeks ago, but I can't say that I was forced. Only perhaps pushed a bit. And I do think if I said no, you would stop. But I also think you enjoy pushing me into something that I never would have said yes to."

She drank her own prosecco, letting it flow slowly over her tongue as she looked Jack over, perhaps staring at him more directly than she had to this date. "I think in fact you might spank me even if I didn't ask. But you would stop if I said so." She nodded to herself as if having solved a puzzle.

"Yes, I would like to explore more. It frightens me, you saying that you want to see my limits. Because that requires that you push me too far, doesn't it? But I do want to see more. I do..." she blushed now again, finally, at these words. "I do enjoy it that you choose for me. So I accept this little dynamic of ours." She picked up the bruschetta and began to eat, having spoken more directly than she thought she could do again.

Perhaps she was one of those people who need to think things through by talking, because it seemed to him that she'd come to a realization about herself and their situation. He keyed in on the word "ours", which connoted a togetherness, a relationship, that made him smile. And really for the first time since she'd been here he felt her truly present in a conversation with just him, and it endeared her to him even further.

He nodded as she spoke, and his cock started to rise when she mentioned spanking, because he certainly did intend to spank her. "Yes, It comes down to trust, ultimately, doesn't it Rachel. This little dynamic of ours," he echoed her, "comes down to trust... and mutual trust. Because I trust you."

"So tonight we'll explore a little more, though it will just be the two of us, as I said. I hope you don't mind terribly, but I'd like to spend more time with you during the day. I was planning on a little adventure tomorrow, the two of us. We'll hop in the convertible and take a ride, how does that sound?" He said, taking another sip of his prosecco.

"And I do plan on spanking your lovely tight ass," he said, looking at her with a devilish grin.

Rachel's brow had furrowed in puzzlement as Jack said that he trusted her. It didn't make sense to her at first, that he would need to. Wasn't she the one submitting? But as she considered it, it occurred to her that there was vulnerability on both sides. Couldn't she go to the authorities right now and say this older man had been taking advantage of her? Couldn't she contact her father and say the same? She supposed that he was trusting her each step of the way.

Those thoughts were banished when he explained that they would explore more tonight. She could feel her heart rate increase. Jack had emphasized that it was just the two of them, twice now. He seemed to want her to know no one would spring from the shadows, but at the same time the intimacy that suggested was novel. She had spent these days wondering when he would touch her and it seemed the time had come. Or had he changed how he felt? His talk of taking a ride in the car, spending the days together... she wondered briefly if somehow he had fallen for her and their little games would change.

But he ended his statement with a cheeky comment and a devilish grin and Rachel laughed, realizing that not so much could have changed in this man. Perhaps this was part of the appeal, a man who was fully matured, who would not change for her, not fall head over heels. Just be who he was. "Well, I suspected it was a bit of smoke when you suggested you wouldn't."

She did her best to sound mature, unfazed, the type of woman who would not blink at talk of being spanked. But inside she was tied in knots, her heart beginning to pound hard. "I suppose no trip to Italy is complete without a spin on a country road in a little convertible. I'll clear my calendar," she told him with a smile.

He hadn't really considered her capacity to flirt. Given their situation, she hadn't really had to, or maybe she just felt comfortable enough with him that she wanted to. Either way, it pleased him immensely, and for the next 45 minutes she did flirt, the prosecco and the wine doing their work to relax her as Jack asked her questions about school and her family and her hobbies.

Jack was feeling smitten with her, and couldn't take his eyes off her, barely acknowledging Isabella as she brought the second and third courses and finally the dessert and espresso. After she poured a light dessert wine, Isabella said, "Buona notte ci vediamo domani." She winked at Jack and smiled at Rachel, waving over her shoulder as she walked back to the house.

As the night went on, Rachel felt the facade of the relaxed, flirtatious young woman take root in here so that it seemed almost that it could be true. It was too different from the woman she had been a week ago though, for it to feel quite right. She had at the beginning simply allowed these things, and now she had repeatedly given permission, nearly asked for them.

And yet that ease she showed on the surface masked a boiling ocean of emotion. Inside, beneath the light banter, another pair of eyes watched Jack, always wondering what was coming, what he was up to, her heart spiking at the innocuous gesture misinterpreted. By the time the dinner had come to a close and the lights nearly gone, her heart was pattering like a creature of prey, ready.