Summer In Tuscany Ch 05

After a night like that, Jack usually went to sleep with a clear head, a pleasant afterglow inducing a soporific state almost immediately. But last night, it wasn't until he started brushing his teeth that he snapped out of a daze and realized he needed a shower to wash off the physical remnants of the evening. And when he finally slid into his sheets sleep didn't easily or immediately arrive as it normally did.

Instead he kept replaying every detail of the evening with Rachel, and though his mind did recall the sexual aspects of the night, it was her voice that kept playing in his head, keeping him awake. Little snippets of things she'd said, her smile, a new tone of flirting he hadn't heard before. Then later, the whispers urging him to cum for her.

And unlike other nights with his various partners, where there always been a polite but clear ending to the evening without any awkwardness or unmet expectations, a mutuality of intent, with Rachel, a splinter of uneasiness stuck in his brain about the way the night had ended.

Had he been rude? Abrupt? Even after he'd fallen asleep, he didn't sleep well. Once during the night, when he woke up, he wondered if the pressure he'd felt against his back was Rachel, that maybe she'd crept into his bed in the middle of the night, but when he reached behind him it was nothing but a pillow.

When he awoke to the morning sun, he didn't feel the usual restful benefits of sleep. But he also met the morning with a new level of anticipation that he'd see Rachel at breakfast, and remembered his commitment from the night before to spend the day with her. He tossed on his usual morning attire of cotton shorts and a snug t-shirt, debating whether he should run, or wait for Rachel in the kitchen.

For Rachel, sleep had not come easily. The combination of the evening's wine and the fading of her adrenaline had seemed to set the stage for falling into an easy slumber. All she needed to do was shower and climb into the luxurious bed set in the hillsides of Tuscany that she had dreamed of for months before getting here. However, every step of that plan served to tease Rachel back into wakefulness. And more.

The redhead stripped down, looking at the dress Jack had bought for her and thinking over the night. There was a low hum of arousal already--though he had brought her to one shivering climax, she suspected she was capable of many. She was not the girl who had landed here in Italy weeks ago.

But standing naked and turning on the shower reminded Rachel of Jack and his cameras. He had left their evening hurriedly after his orgasm, and it was easy to imagine the older man asleep, spent. But Jack was not just an ordinary man. It was just as easy to imagine that he was watching her again as she showered. As Rachel ran the soap across her glistening, increasingly tanned skin, she felt a throb of excitement building inside. Each swipe of her hand across her body, each step out of the shower towards the large mirror, came with the feeling of eyes upon her.

Maybe not just his eyes, Rachel mused, as she slid into a silk nightie, and dried her hair. Jack was like no one she had met, or imagined, in that his perversions ran broad and deep. He had invited friends to watch her, and more, before. Why couldn't one be watching her now, as she tread with her bare feet to the bed?

She knew he had watched her here, also, touching herself beneath her covers. Now she was doing it again. Her eyes flitted about the room as her hands roamed her body. Who knew where the cameras were. Could they see her now as her hand slid between her thighs? She slid the sheets down, and she touched her breasts, bringing her nipples to throbbing stiffness poking through the silk. Could he see? She was not sleeping, but writhing on the bed, her fingers working, until she came one more time with a gasping moan.

Even as she finally closed her eyes, Rachel wondered what she would wake to. Would it be like the patio, strangers staring at her? Would she find herself tied to the bed when she woke, her body being played with? She fell into a fitful, aroused sleep.

***

And was almost disappointed when she woke to no audience, no bound limbs. She felt a bit of wetness on her cheek and gasped, touching it, thinking someone might have stood over her as she slept. But no, it was just a bit of drool from her own mouth. Rachel flushed, embarrassed at her own strange imaginings.

But they lingered with her, and she found herself hurrying to the kitchen in her short silk nightgown, her breasts swaying freely, eager to see Jack, eager to know what might be next. She found the kitchen empty and fussed with the Moka pot, her back to Jack as he finally entered, unseen.

He was surprised to hear noise coming from the kitchen and at first assumed it was Isabella, but it was still 30 minutes before her usual arrival time. When he turned the corner toward the kitchen, he was met with a lovely sight. The sun streamed into the kitchen, lighting up Rachel's figure as she moved, highlighting the fullness of her breasts in the sheer nightgown he'd chosen for her days ago, hints of her nipples. The silk hugged her firm young buttocks and her narrow waist and slender hips. Her hair was mussed from sleeping, and the tenderness he'd fell asleep with was instantly replaced with pure lust.

If they were a couple, he thought how he'd step up behind her and press his morning wood against her buttocks and cup her big tits. But were they a couple? What was last night? They'd kissed, given each other orgasms, but there still so much unsaid. His hand reflexively reached for his cock through this shorts and gave it a squeeze, watching her move.

Unlike last night, when he planned the limitations of the evening, intentionally withholding the act of fucking her, at this moment, watching her, it was all he could think about. He thought of lifting up her nightgown and urging his thick cock into her pussy as she stood at the sink.

Him watching, her unaware, appealed to his voyeurism. And this wasn't through a camera, it was right in front of him. He thought of spinning her around and kissing her, pressing against her passionately. Within just seconds, he'd pushed the waistband of his shorts down, freeing his swollen cock, thinking of digging his hands into her hips and pounding her from behind. He didn't want to alarm her, so broke the morning silence, his cock in his hand, with a "Good morning, Rachel."

She jumped at the sound of Jack's voice. She was unaware of how the sudden movement caused her breasts to leap beneath the thin silk, the muscles of her thighs and ass to clench, enhancing the vision he had been soaking in. Rachel was only aware of the sudden skip in her heart, and the flood of something hitting her bloodstream at the surprise.

Her mind finally caught up and processed the sound, realizing the voice was Jack's. That set off an entirely different set of hormones. All the night's thoughts, imaginings, and more cascaded through her mind as she turned to face him. The question rose again, what now? What else?

She saw his face first, his smile, as she processed his polite welcome. But it did not take her a moment to find her eyes drawn by the posture of his arm, down, down, to see his cock revealed already. His fist gripping it. Rachel looked up to his face and read some version of the lust there.

She cast her green eyes back down to his cock and soon was treading across the kitchen on bare feet. She had known Jack to always be in control, supreme control, not just of her but himself. She could not help but assume that he was in control now, and knew exactly what he was doing. And she thought the message was clear.

Coming close to her host, she continued to stare down at his cock in hand. Rachel did not hesitate, the college student lowering herself down to her knees in front of the retiree. Her eyes finally looked up to meet his, but only as she leaned forward to take him in her mouth.

He loved watching her walk, even though it was only half the distance across the kitchen. The trouble was where to focus his eyes. He tried keeping his eyes on hers, but then the bounce of her breasts captured his attention, and then he had to watch her hips, a glance down at her slender thighs, back up to her flat stomach and the most beautiful breasts he'd ever seen, and back to her eyes, and by that time she was on her knees in front of him.

He wasn't sure exactly what he'd expected from pulling out his cock and stroking it. He'd wondered how she'd react, whether she'd start playing with herself, or turn around and bend over, and he was very pleasantly surprised to see her not even hesitate when she saw his cock out. He wondered whether she was already aroused, thought he could kick himself for not watching his cameras this morning. Then he realized he hadn't watched her last night! That would be the last time that happened.

Jack flinched with pleasure at the first touch of her hand. A quiet moan escaped at the sensation of her warm mouth taking him in. "Mmm, that's a good girl Rachel," he said, and his hand reached for the back of her head.

Rachel quivered at the sound of his words. She was hooked on the perversion at this point, the perversion of her servicing this older man, seemingly at his whim, and her only reward his encouragement and validation. There was a small voice inside of her, scared of what she might do for him, if only he continued to tug her down this path. To tell her she is a good girl.

But that was a small voice, and the larger one was her own passion, carefully stoked all night as she twisted in the sheets. Rachel was eager, eager to prove herself to him, forgetting their seeming agreement that it would be him who would decide what happens next. Taking his cock in her hand she opened her mouth and engulfed as much of it as she could in one go.

She had no expertise at this; a girl with her face and body had never needed to prove herself in this way. But she managed to take half of his cock in her mouth, not enough to cause her to gag, and to lock her full beautiful lips around it. She ran her tongue up against his shaft, sucking in her cheeks as she dragged her head back, back, until only the tip lay on her lips, and then pushed forward again, eagerly taking him back inside.

Jack was undoubtedly thrilled that she was sucking his cock, and he admired her enthusiasm. It did feel good of course - how could it not - but it didn't take long for him to realize that her technique needed improvement. That there was really no method to it.

Jack remembered a snippet of their conversation from the night before, about teaching her, guiding her, and he saw this an opportunity. He'd had his cock sucked by some immensely talented women who could edge him for close to an hour, and mind-blowing orgasms. Since he knew now he wanted this to be a regular thing from Rachel for the rest of the summer, he decided that that morning was a good time to teach her some technique, to teach her how to suck his cock, of course, the way he liked it, but as a service to the men in her future whose cocks she would suck as well

"That's it, Rachel... mmm, that feels good... now... use your hand on me too. Remember the way I taught you to hold my cock last night? My shaft?" He tried not to sound too professorial. "Get a good grip on my shaft and stroke it slowly while you focus your mouth on my tip, ok? Try that for a little while."

Rachel looked up and met Jack's eyes, as she carefully wrapped her soft hand around his hardness. If any other boyfriend had given her instructions like this, she would have been mortified, stung that she was not a good enough lover on the inside - and giving him an intense cold shoulder or fuck you on the outside. But when Jack said it, the older lover who had taken her under his wing and taught her the perverted underbelly of sensuality, it did not make her feel small, hurt, or pissed. It did make her determined to not be the foolish little girl she was sure she seemed to him, however.

Rachel stroked his cock, slowly, softly, like he had instructed her last night. Her hand went from his root to her mouth, back and forth, in a slowly increasing rhythm. Meanwhile, she did as instructed, wrapping her full lips around the head of his cock. She sucked that fat head, her tongue lolling around it, her head subtly bobbing despite itself, a centimeter at a time. She looked at Jack, looked up at his face the whole time she suckled him.

The change in technique was subtle but important to Jack, confirming how coachable she was, confirming again her willingness to learn and desire to please. That combination would continue to lead the two of them down very erotic, kinky pathways. She could have ignored his guidance and instruction completely, or half assed it, but she listened, corrected her actions, and the result was more pleasure for him, and the added thrill of her following his instructions.

Then there were her eyes

Last night in the dusk, twilight, and candlelight they'd experienced a new level of intimacy, their first true intimacy, the touching and kissing, and they'd made eye contact between kisses, and stroking, but this was different.

In the morning sunlight in the villa's kitchen, her eyes were still the slightest bit sleepy, but it was the first time she'd looked at him with his thick cock filling her mouth, and the sensation was electric. A mixture of hungry lust, and yet almost a pleading for positive reinforcement. He smiled down at her, put a hand in her auburn hair, and said, "Yes, that's it...exactly. You're such a good girl Rachel. You're so sexy, such a quick learner. So beautiful."

Past his cock he could see her hard nipples against the silk, her full cleavage. He pumped his hips slowly. He loved dirty talk, and wanted to bring that more into their relationship, "You're going to be such a wonderful cocksucker, Rachel. Do you want to become an amazing cocksucker?"

At his last words, a moan slipped past her lips before Rachel had even processed the speech. She had preened at the compliments he dripped down over her, but the word 'cocksucker' struck her somewhere deep in her gut. Her guttural moan slid past his cock, heavy on her tongue. Green eyes heavy with lust, her eyelids half closed as his words sank all the way into her. "Yes," more a breath than a word.

She felt the shiver from her core as she agreed, agreed not only with his statement, but agreed to let him speak of her like this, to turn her into something much different than the girl who had traveled here to Tuscany. Something much different than anyone wanted her to be.

"Yes, please, help me," she breathed, the idea of driving this jaded, experienced man crazy with her own mouth, her own skill, setting a fire in her belly. She took him in her mouth again, twisting her lips and tongue and mouth on him as she stroked him, firmer now, wanting to make a reaction, wanting him to be shocked and impressed, wanting to be the best he had ever had, this man who had had so many.

He could tell she reacted to the word, and his praise, by a new level of eagerness on his cock. "Good girl, Rachel. I'll help you. I'll turn you into a very talented cocksucker. Of course that means plenty of cocksucking practice, doesn't it. I recommend once a day. Before breakfast, every morning, cocksucking lessons.

"And when get you really good, perhaps I'll invite some friends over so you can practice on them as well. Would you like that Rachel? Sucking my friend's cocks too?" While talking, he kept up his steady pumping of his hips, imagining his friends in a small circle around Rachel, going from cock to cock. Someday, yes, perhaps, but first she would need to practice on him.

"And of course a good cocksucker swallows every drop, doesn't she Rachel. You'll have a nice big load of cum. That's it... just a little firmer with your hand now."

Rachel did not answer with her words. She couldn't, not without taking her mouth off of Jack's cock, and she didn't want to do that now. She wanted it less the more he talked, the more he aroused her with his words. She communicated her answers with an eager nod of her head that led his cock to bobbing, with the intense suction of her mouth, with the eager swirl of her tongue.

And that did not stop even at Jack's mention of his friends. As pleased as she was in this moment to finally have Jack's cock to herself, for their relationship to have moved forward in this way, she knew there was never going to be anything normal about it. Nor did she want that. She was not in love with Jack. But she was in some all-consuming passion for what he did to her. It had begun with him watching her and sharing her, and now she knew it would continue. His friends' cocks in her mouth, in her cunt, their cum down her throat.

The thoughts, the words, were driving her crazy, and she could not help but increase the pace and the intensity of her blowjob. Her head bobbed, and as he directed, she squeezed tighter with her hand on his slick shaft.

She wanted it, she wanted this load of cum in her mouth. Because it was nasty. Because it was wrong that her father's friend should talk this way, treat her this way, use her this way, make her throat an empty vessel for his cum. The nastier Jack's words became, the more she moaned in excitement, her eyes rolling up to look at him as she feverishly stroked him with her hand, her lips, tongue and throat.

From the way her pace increased on his cock, the intensity of her mouth, a new mewing from her throat, and from the reflection in one of the windows of her hips grinding, he knew his words were having their intended effect. He wondered if it was the idea of her sucking of his friends that had done it, or just the dirty talk in general. There would be more of that, and he would train her to use it, last night a delicious hint of what those words would sound like from her in the throes of lust. But first...

Behind Rachel, he saw Isabella walk across the hallway and stop. She smiled at him, shook her head bemusedly. She turned her hips as if she was about to continue walking and he mouthed the word "stay" to her.

Isabella turned to face Jack again and undid the top buttons of her shirt, her deep cleavage appearing. Rachel's tits were amazing, his favorite, but Isabella's were lovely in a different way, and she knew it. She cupped her breasts and squeezed them, creating a deeper crevasse, as Rachel continued bobbing away at his cock.

The words came fast. "Such a good cocksucker, Rachel. That's it... suck my cock... I know you love my big thick cock don't you, Rachel... you want me to fuck you with my big cock, don't you. But now you're going to swallow my load... that's it... that it..."

Jack looked down at Rachel's eyes, up to Isabella's, who gave him a little nod, and that's all it took. He lightly held Rachel's auburn hair and pumped his hips, unleashing the first load of jism into her eager mouth. He moaned, pulled back and pumped again, the pleasure so intense he struggled to keep his eyes open, his hips trembling. Two more thrusts and he knew he was empty.

Rachel was dimly aware of something drawing Jack's attention. As Rachel looked up at him, she could see his gaze move behind her, focus on something else, and then return. She wondered vaguely what it might be. She had a vision of his group of friends standing behind her, watching. For a moment she saw herself as someone standing back there might: Imagining herself on her knees, the desperate way in which her head was bobbing, imagining the sound of it, the sight of it. Her mind and body thrilled, her hips unknowingly grinding against air as she imagined the scene.

A quiet little voice in her head wondered what he was truly looking at, but it was silent compared to the roar of need in her mind, need for this cock, need for Jack to cum. She let his dirty talk wash over her, and there was a part of her that felt its power, and knew that in this moment she would agree to any of that, agree to anything he said in a moment like this.