Summer in Tuscany

Jack slept well, and the following morning at breakfast while sipping his cappuccino he was replaying the evening before and felt himself growing hard again. When Isabella arrived, wearing her trim crisp uniform, he was already erect and stroking himself slowly, the waistband of his soft cotton gym shorts he slept in bunched at the base of his shaft. Isabella saw him stroking, and gave him a smirk and a "you naughty boy" smile.

Isabella was a young widow whose children grown and moved up north to Milan. To his knowledge she had no man in her life, which surprised him. She was very pretty, dark brown hair, deep brown eyes. He had known about her, seen her in town while her husband was still alive. The husband had left her with little money, and when Jack had heard about it, he offered her a job at the villa. He was upfront with her about his lifestyle. He'd been looking for someone he could trust, who would be accepting and could help around the house. He paid her extremely well, and she was appreciative.

She had seen him masturbating around the house many times and hadn't said a word, even when she occasionally saw the group of people naked in the living room or by the pool. He'd been surprised one morning sitting at the kitchen table when he was completely naked, stroking himself while watching a video on his laptop. Isabella had come in to wash the breakfast dishes, smiled at Jack as she went about her business, Jack admiring her surprisingly firm ass in her uniform.

When she was done with the dishes, she turned and faced him and asked in Italian if he needed help. He nodded, and as she walked toward him she undid the buttons on the front of her uniform, lifted her bra up and revealed to Jack her beautiful full tits capped by large dark areola and hard nipples. Womanly was the first word Jack thought of when he saw her breasts.

She had walked up to Jack, grabbed her breasts for him to admire, and then kneeled between his legs, and took his big cock between her hands and began to suck him off. Since that day, there had been other encounters, hand jobs at first and then blow jobs before she finally allowed Jack to fuck her. She'd made it clear that it was just sex, and Jack was fine with that too - an unspoken agreement. She was willing and ready to help, and they'd gotten to the point where all he needed to do was give her a signal.

Jack returned her "naughty boy" smile and asked her if she would please quietly go into Rachel's room and clean up the small mess at the foot of her bed. Within a few minutes Isabella was back, smiling broadly, said the words this time, "Tu sei un bambino cattivo," and without hesitating, unbuttoned her uniform and pushed it off each shoulder until it was around her waist.

She unhooked her bra and placed it on the kitchen table. She knelt, cupped her breasts together and allowed Jack to fuck them. She had just managed to get her lips around the thick tip of his cock when Jack saw Rachel appear. His first thought was Ann Margaret in "Carnal Knowledge?" he tried to remember. Eyes half closed, sexy, auburn hair damp,, her gorgeous tits restrained only by the thinnest cotton of a sheer white tank top, wearing her little pajama shorts. A small groan at Isabella taking more of him in her mouth. "Good morning Rachel."

Rachel had slept well herself. Last night, as she and Jack had both watched him cum on her bedroom floor, even while she was bringing herself to her own orgasm, it had felt as if something had shifted. The sexual tension which had driven her crazy, driven them both to that point, had not dissipated in that moment but it had changed shape. It was no longer a question of what Mr. Morrison wanted, or what were her boundaries. She had left her door open, he had come in. That boundary was gone now, they had erased it. The cameras she knew were watching her simply an extra now that he had watched her with his own eyes.

He would watch her again, she knew that much, and the idea excited her. The question now was simply what would he watch her do? He had left her the outfit and the vibrator she had used last night, and that seemed to set the stage for the future. He liked to control things, she thought, to create situations. he began to wonder if he had somehow arranged for that scene at the poolside, when she had woken surrounded by his friends.

Mr. Morrison would watch again, that was settled, but the question prime in Rachel's mind was if he would touch her. He clearly desired her, and she had expected him to throw himself on her last night as she sprawled naked before him. It certainly could not be some form of gallantry that stopped him, could it? The man had cum right there on her bedroom floor. But perhaps that was meant as some noble act of restraint in his Italian soul. She could not be sure. She only knew that as crazy, as truly insane as it was, she easily became aroused at the thought of the 60 year old man thrusting on top of her youthful body.

It was with these thoughts in mind that Rachel stepped out of the shower in the morning, barely wrapped in a white cotton towel. She stopped in surprise at the sight of a figure in her bedroom, briefly thinking that she had somehow summoned Jack to her with her thoughts. But no, it was Isabella, the dark, silent housekeeper. Rachel stuttered out a greeting in Italian, adjusting the towel to cover herself more modestly. In turn the housekeeper only smiled, a mysterious little smile, stood up from where she had been working and left the room.

Isabella was gone before Rachel realized what she had been doing with that cleaning bottle and rags. Rachel could see the wet streaks on the stone where Mr. Morrison's cum had landed. On the comforter too. Rachel blushed, wondering why she had left them there---well, knowing why she had but not wanting to admit it now that she had been caught. The housekeeper would certainly know, or suspect, what had happened between her and her host and for the first time Rachel felt some shame at what was happening.

The shame did not last though. The act of dressing for breakfast brought her mind back to Jack, and soon it was the idea of his eyes, if not his hands, on her that preoccupied Rachel's mind. She dressed herself in her typical breakfast attire, even though she had already showered, slipping on the familiar tanktop and shorts, wanting to watch Jack's eyes travel over here tan thighs, feel them on her rear when she turned around. Rachel took a deep breath and hurried to breakfast, walking through the kitchen door with her chin up and her heart pounding.

She actually saw the bra before she saw anything else, looking at it in some confusion, lying on the kitchen table, wondering if it was some new gift from Jack. As her eyes shifted to him those thoughts disappeared. She hardly recognized Isabella at first, who always wore her neat uniform. Now it was hardly visible, her back bared to Rachel, her brown hands pressed to the sides of her breasts as she knelt between Jack's wide open legs. Jack was thrusting up and down obscenely, Isabella's dark head bent over him, the two locked in some perverted embrace.

Rachel gasped in shock, stopping and standing still. She was about to hurry backwards out of the room when Mr. Morrison spoke, seeming to demand some sort of response rather than pure flight. "I, I ..." she found she had nothing to say. Certainly not good morning. She actually felt tears welling, sickened at the sight of Jack, only hours after he had come to her, pleasing himself with this woman.

Jack noticed her shocked expression first, and then the shift in her weight as if she were ready to flee back to her bedroom. "Stay," he said, in a tone he thought sounded less like a demand than a plea, a friendly but firm plea reinforced by the smile in his eyes. In some ways the transition to this new phase of their relationship was more delicate than the initial one, and this morning was an important next step. He couldn't sound demanding, not yet, perhaps later depending on how much she would need and want it. But he could see the confusion in her eyes and her forehead, and he knew he needed to reassure her.

"Stay and watch," he said. Isabella took that as a cue, and with her free hand grabbed the hem of her skirt and lifted it up over her full, curved bottom that narrowed quickly to thin toned thighs, an offering for Rachel. "Get your coffee first if you'd like," he said, his smile expanding to the corners of his mouth. "I was telling Isabella how incredibly sexy you were last night Rachel." At that point Isabella took him even deeper into her mouth and he couldn't speak, her lips down his shaft. "How amazing you were, how beautiful you were." He looked in Rachel's eyes and down her body again, much like he did the night before after saying goodbye to his guests, like he knew he would many more times in the coming days and weeks, and the gesture had the same effect it did last night, as if his eyes on Rachel's breasts automatically made her nipples harden.

"And you look beautiful right now Rachel, very sexy. I love that tank top, I have since that first day you wore it for me. Your breasts are truly special, Rachel, firm and full. They're perfect." Jack also knew this next phase required moving beyond the nearly unspoken, wordless realm of sexual tension they'd been in up to this point, and into conversation.

"I'd love for you to stay and watch and enjoy yourself," he said, his voice soothing but confident. "I'd love to see you touch yourself again Rachel. Would you do that for me Rachel? Touch yourself for me this morning like you did last night? You know how I enjoyed that. Do you know what Isabella called me after she cleaned up after me this morning? 'un bambino cattivo' - a naughty boy. Yes, I'm a naughty boy. Have been for a very long time.

"How about you Rachel? Are you a naughty girl? Stay and watch and touch yourself for me Rachel. Like last night. You're so incredibly sexy So beautiful."

He pointed to a chair on the same side of the table that he had already pulled away and angled toward him. She hadn't left yet, he thought to himself, a good sign. Isabella slurped on his cock, tried to look at Rachel out of the corner of her eye and arched her back and spread her legs more. Jack wished he could see what Rachel was seeing because he was certain Isabella must be wet by now.

"Please," he said, as if using politeness were almost a last resort. "Stay Rachel. Sit," he said, gesturing to the chair again.

Jack's voice was determined enough, if not commanding, to stay Rachel's feet. She stood awkwardly, not knowing where to look, but having so readied herself for doing what he wanted her to do that she felt compelled to stay. She glanced over with a flush of embarrassment, seeing that Isabella, rather than rushing away ashamed had pulled up her skirt, revealing her full dark rear and the shadow of her pussy between.

Rachel found her eyes trailing up the curve of that spine to where the dark head worked away at Jack's crotch. Rachel found herself, despite herself, wondering at how the woman fit that giant cock in her mouth, wondering how much of it she could. There was no sign of struggle or effort from the housekeeper, only an intent effort that echoed the determination Rachel had felt performing for Mr. Morrison.

Rachel's eyes kept going up and found Jack's. They were boring into her--not just at her eyes, but up and down her body like the stroke of a strong hand. She hated herself for growing aroused, but loved it too, the now familiar tingle that shot through her abdomen and crinkled her nipples, quickened her breath. She barely heard his words, but she felt them, felt his voice like another stroke on every part he mentioned, his words making her breasts throb, her pussy hum.

The message was clear: he still was interested in her, still lusted after her. But he was not ashamed of what he was doing. There was no discrepancy in his mind between wanting to see Rachel cum, and wanting her watch him cum with another.

"I, I don't think I should," Rachel stuttered, her eyes inevitably drawn down to the head that worked on Jack's sex, the sleek dark body that curled between his legs. Whether Rachel meant stay, or touch herself, wasn't clear. It wasn't clear she meant it, as she did stay. She in fact walked towards the chair he indicated. She could not get coffee, could not pretend that level of normalcy. But she could embrace to some extent his wickedness. After all, she told herself, it meant nothing to her what these two chose to do. There was no shame in watching what they put on display. If they displayed their perversion, it didn't make her perverted. She sat delicately on the chair, keenly aware of her stiff nipples, the warmth between her thighs, the wet sound of Isabella's work.

Rachel perched herself on the chair close enough for Jack to smell her clean skin and hair. What is it about a young woman freshly showered that he found so sexy? Her position on the chair, almost like an eager student at the front of the class--Jack wondered if she had worn a uniform to her school--her back slightly arched, her knees together, accentuated her breasts, her narrow waist and balanced hips.

He hid his relief that she stayed. Her position suggested she was awaiting further instructions, as if her teacher, Jack, needed to give her an assignment. Jack leaned back in his chair to give Rachel a more open view of Isabella at work. See, class, and my star pupil Rachel, this is the proper way to give a blowjob. Notice the firm grip and steady hand work, complimented by the way Isabella is using her lips and tongue. See how she combines the consistent teasing of my tip with her ability to take me deep in her mouth and throat, while she uses her fingers at the base of my cock?

And now the assignment. "Rachel," he said quietly, "touch your breasts for me like you did last night. Watch Isabella, she's very, very good at this." He saw Rachel's eyes shift down to Isabella, and he wondered if Rachel thought he was teaching her for her to perform this act on him, or if she thought he was doing this as life lesson for her, for her to please any man in the future. He was tempted this morning to go in that direction, to ask Rachel to take her place alongside Isabella on her knees, but it was too soon. "It's ok to touch yourself. I'd like you to."

Jack continued a steady slow thrust up into Isabella's mouth. He could now smell the scent of Isabella emanating from her open legs, a scent he knew would soon be mixed with Rachel's.

Rachel's nipples in the thin tank top struck him as art. Yes, he appreciated the beauty of the Tuscan landscape, but his preferred landscape was women's bodies, and Rachel's was to him simply exquisite. Did she know this yet about herself? He wished he had a professional photographer in the kitchen to take her picture, and consoled himself with the fact that the high definition camera in the corner of the kitchen would at least capture this moment.

Rachel feels her pride at war with her arousal. She wants to do what Jack wants, as it's the same thing her body wants. It is undoubtedly exciting to sit her and watch as Isabella so expertly blows Mr. Morrison's cock, to listen the sound of her wet mouth and watch her hands tease his iron shaft. It is, funnily enough, not the perversion of the moment that bothers her and makes her hesitate. This is in fact no different than what happened last night, she reasons, the two of them watching each other as they reach their own orgasms. But the fact is that Rachel walked in the kitchen this morning expecting to have Jack flatter her with attention, flirtation, perhaps even more. Instead she found him having another sate his desires. She knew she would not stoop to sharing him with Isabella, she had more pride than that. But to be so harshly replaced, so flagrantly reminded that he did not intend to take her himself, it was a sting.

His words, though, were not demeaning, and Rachel began to ponder, perhaps for the first time truly, what Jack's motivation was in this. He had had every opportunity to take advantage of Rachel, and he had not. Had not ever touched her with more than his eyes. It was only appropriate, Rachel had to admit, for a man his age and with his association with her father. He was perhaps more aware of that situation than she, and determined to follow some sort of principle in leaving the young woman alone. His intention was instead a sort of noble mutual pleasure.

With the ease to her indignation, Rachel found her hands moving without thought, the idea of pleasuring herself under Mr. Morrison's gaze becoming more natural with every passing day. She squeezed her full breasts through her tank top, rubbing the cotton against them, as she watched Isabella's dark breasts, and the way the woman would raise and rub them against the base of Jack's cock. She rubbed the cloth against her nipples, squeezed her breast in one hand and then the other, until a hand drifted down to her freckled thighs, parting them and rubbing herself against her shorts.

Soon she had left decorum aside, watching the pornographic event happening right before her with one hand inside of her panties, her middle finger frigging at herself eagerly. She realized that Mr. Morrison did not feel he could touch her, and so he had staged the closest they could come to it. She could not suck on the cock of her older host, but she could sit inches away while an able mouth did. She dipped her fingers inside of herself, feeling certain now that Jack thought of her mouth on his cock as he looked at her, coming as close to the invisible line between them as he could.

"I want you to cum on her breasts," Rachel told him, suddenly looking up to meet his eyes. It is what she would do for him, she knew, knowing how he loved the sight of her breasts. "I want to watch you coat them."

Something had changed from the point at which Rachel had sat down. For a few seconds her mind was clearly elsewhere, and then she was back. Even through the occasional tunnel vision Jack sometimes experienced during intense periods of arousal, he could tell by the way Rachel's eyes came back into focus some decision had been made, and though she appeared distracted for perhaps only seconds, he knew somewhere in his gut that for her it was profound, more than a simple Clash-like stay-or-go decision.

But once it had been decided, her hands had gone to work, and her legs had spread and Jack watched her play with her breasts and then spread her thighs and start to finger herself. Her bottom lip had separated from her top, and Jack's eyes were drawn there, thinking about what her mouth would taste like right now, how it would look with his cock filling it, her blue eyes looking up at him. Yes, he had avoided touching her other than the brief greeting the previous night, and he would hold out a while longer. He had planned all along to do much more than that, but it would be at her insistence.

He knew his moral compass wasn't particularly strong, never considered himself a highly principled person, and both admired and reviled those who were. His principles were malleable, adjustable, flexible, adaptable from situation to situation, from week to week or minute by minute. In Rachel's' case, as of this morning, as of this moment sitting in his chair, his guideline was this: he would continue taking the game to new levels and would avoid touching Rachel until she touched him first, at which point in his mind they simply crossed another threshold, nothing more or less. Until then, the teasing would continue through a series of not at all unpleasant situations.

He saw her eyes leap up from his cock to meet his own, and he could tell another decision had been made. The tone in her voice alone almost made him cum, its timbre resonating with sex. And her actual words, her request, brought him that much closer, and the Rachel of last night was back, each moment like this unpeeling her defenses and exposing her core. "I would love to," he said, and he could tell the request had affected Isabella too, because she was gripping him harder and pumping faster.