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He kept a steady pressure and rhythm of suckling and pinching, enjoying the reaction of her body, feeling the shift in her ribcage as she pushed against him mouth. He released each nipple, and paused, letting them react to the absence of pleasure and pain, and then switched places, her breath catching as he took the swollen just-pinched nipple into her mouth. His hand, his free hand, slid down her stomach, toward her pussy.
The Tuscan air, even at night, was not particularly cool. Yet when Jack released her breast from his mouth, the wet nipple puckered harder from the sudden chill. The other pulsed, his sharp pinches having brought a rush of blood right to the surface. It was a relief when he suddenly bent his mouth to the pinched nipple, sucking hard on the enervated flesh. But knowing what was happening next, Rachel clenched her body, fists clenched at her side, as Jack pinched the other nipple tightly until she rose on her tiptoes.
The nerves running up and down her body were at wit's end; they did not know whether to tell Rachel she loved what was happening or was horrified. They hardly noticed Jack's hand sliding own her stomach until it reached the increasingly sensitive flesh below. All she could think about was red hot sensation burning through one heavy breast and the intense suction on the other. The young woman felt as if her body were ready to explode.
---
From the cameras in the bedroom, bathroom, and living areas, he'd seen every single inch of her body.
He'd watched as she washed her underarms, as she even clipped her nails, put on her makeup, watched her pee, had seen her masturbate on many occasions, had watched her shave her pubic hairs off exactly two inches from where his hand was now headed.
Touching all of this, finally, brought its own new unique pleasure, connecting the points in his brain between the visual and tactile that now, after how many weeks, finally melded.
So though he'd seen how flat her stomach was, the dimpled muscles visible when she was in the shower, or wearing a bikini, feeling the tautness under his fingertips was so different, and new, and now he was determined to explore with his fingers that to this point he'd touched only with his eyes.
He heard her breathing over the cicadas. Her stomach had a different scent then her nipples, and he looked forward to the release of the scent of her cunt when her lips opened for his fingers.
Rachel's stomach was taut, tensed from the sensations Jack was pouring into her. As his fingers trailed downward, they sent ripples of new sensations through those muscles, down through her body, so that she was primed for his touch before it reached each new spot. Rachel stood, hyperfocused on his fingertips, his mouth--with one hand she touched Jack's shoulder, grounding herself as she swayed on unsteady knees. With her other hand she unconsciously reached again for Jack's erection. Her hand slid softly across it the same way his fingers stroked her stomach.
The lower his fingers explored, the tighter Rachel's grip on Jack's cock. When he brushed across the thin wisp of her panties, Rachel squeezed hard and gasped from the subtle but intensely anticipated sensation. "Oh, Jack," she breathed, looking up at him with wide eyes. Her nipples still pounded from his intense treatment, now she could feel her pussy throbbing, waiting for a touch. Would he truly touch her? Was this the night, finally she submitted--no, she had submitted long ago. Would this be the night he took her?
Why did it hit him right then that in the days she'd spent living under his roof, they'd actually spoken very words directly to each other. "I'm going into town, be back later" was probably the phrase he'd heard most often. Had she ever called him by his name?
He pondered that as his fingers followed the thin edge of her panties. So as a percentage of the total words they'd spoken to each other, Oh Jack counted for one out of a thousand? One of ten thousand? whatever the actual number, the weight of those two words was disproportionate, especially given the tone she'd used. She'd probably use more words that night, and certainly more for the duration of her stay, and he did vow that he would talk to her tomorrow, really talk to her tomorrow and every day after, but whatever the final count of words were that she'd speak for the rest of the summer, the significance of those two simple words would stick with him, possibly forever.
Did those two words chisel away at some hidden romanticism he had buried somewhere?
Oh yes, and she was gripping his big cock tighter. He liked that. Too many women patted or feather-touched his cock like it was a pet. He wanted to feel a grip, a squeeze, a mini-vise, especially as he aged. It helped. Get that blood flowing and throbbing and echoing in the veins.
His mind circled back to the task at the tip of his fingers. He'd seen her masturbate enough, and had seen it when his friend Craig fucked her, that she was deliciously, excessively wet when she was aroused. He wanted to feel that, and was already thinking about how he'd slather her juice across her nipples and lick it.
For Rachel, she was unaware of what was happening in Jack's mind. She was hyperfocused on only his fingertips, their meandering path down her body. They had brushed across the thin fabric of her panties. Now they outlined the swell of her lips through the silk. He could feel the wetness that had soaked the fabric. Could feel the heat that his touch had generated flowing here out of her core.
And Rachel felt his touch--both firm and sensitive, like him. He was larger, bolder, more intimidating than the younger men she knew. Yet he was also more aware, more delicate, more precise than they would ever be. She felt him explore the terrain of her crotch through the panties, but knew he could tear it away if he wished, could plunge himself inside of her, or manipulate the nerves of her cunt with immense precision. Her gaze drifted back down, thinking of nothing but what those fingers would do next.
The obvious next step would be to slide his fingers down inside her panties, but Jack stopped just underneath the delicate hem, and instead of pushing underneath, he grabbed the waistband and tugged upward, putting pressure on her clit and splitting her lips ever so slightly.
Rachel responded with a grunt of surprise. Ready for the light touch of his fingertips, she instead felt an intense pressure on her sex, her slight panties suddenly tight against her in a way that would be uncomfortable if she wasn't already highly aroused. Any touch was welcome--no, desperately needed--and so even this caused her to flush and moan in need.
After hearing her moan, he knew he'd done the right thing, and though he thought of bringing her to an orgasm this way, as he'd done to many other women, he did want the sensation of her pussy walls clenching against his longer fingers.
He released his grip on her waistband and pressed his hand back against her flat lower belly and started to tunnel into her panties
At just the right spot, her wetness reached his fingertips, and Jack gave out a groan of his own. She'd squeezed his cock, a cause and effect, when he'd tugged on her panties, and within an instant his hand pushed further down until his palm cupped her pussy. "Rachel... you're soaked... good girl," he said.
After the slow tease of his fingers--in a way, the slow tease of his presence over the past week, circling, circling her but never quite touching--the sudden dive of his hand deep into her panties felt atomic. Rachel's mouth opened in a quick intake of breath, her hand once again squeezing Jack's shaft hard. She moaned, as much from Jack's words from the feel of his hand on her wet lips.
She could no longer help herself, control herself. Rachel found herself grinding her pussy hard on the base of his hand, her wetness on his palm, her slight panties stretched wide. She jerked his cock wildly, stroking back and forth, needing more from this encounter, from this moment, from his flesh, needing more.
"Slow down," he said, "tease it, stroke it, don't jerk it," as he curved the tip of his finger and started to push up into the open wet furnace of her cunt, the tip pushing in and out until past his first knuckle, the whimper of voice in his ear blocking out the sounds of the summer evening. "You're so tight. So wonderfully, deliciously tight."
Rachel groaned in frustration at Jack's instructions. She was barely even aware she was doing something to his cock--her fist around his shaft was simply acting out the sensations his hand were producing in her body. And the last thing she wanted now was to slow down--for her to slow down, or for him to. Yet there was authority in his voice, in his presence, that the young college student felt keenly. She did not think to fight, or ignore his instructions.
A portion of Rachel's brain took over the job of slowly stroking the older man's cock, up and down, a light touch on the hot flesh. The rest of her brain was only aware of his finger entering her, her own hot flesh bearing down on him, resisting and inviting him at the same time as she pressed against his venturing hand.
Jack knew from his own experience in his youth that most men, or boys, rush the fingerfucking. They're so thrilled to finally have their finger inside a woman's pussy that it's like something takes over their hand and they can't control it. He had since learned, like a lot of other elements in life, it was about rhythm, anticipation, teasing, alternating slow and soft and fast and hard. And so though her hips were reacting already to his penetration, he pushed his finger deeper inside her tightness before dragging it almost all the way out.
The older man's expertise brought the results he intended. Rather than the rough pounding most men learned from porn, his patient teasing had Rachel's legs parting like a flower, her moisture running, her vaginal walls squeezing with intense excitement. He reaped the rewards in how eagerly she worked his cock, but that wasn't even an afterthought of hers, it wasn't a thought. Just the motion of his fingers translated into the sensations of her body translated into the motion of her own hand.
Rachel groaned and swayed, her body eagerly pressing to take him deeper, but glad he was not simply heeding her body. He knew better than it did, and soon she was rocking to the rhythm of his moments, crying out in need.
With his finger now working a steady beat pushing in and out her pussy with his long fingers, he wondered if she'd ever squirted. He guessed she hadn't, and made a note to himself to introduce her to it another night. He changed his position enough to reach behind her and cusp her firm buttock for leverage, and reattached his lips to her erect nipple, a hint of a scrape from his teeth.
His touch brought Rachel into a perfect arch--her body wanted the contact, more contact, his mouth on her breast, his hand on her rear, and inside her pussy, she pressed into all of that, forcing her body into a beautiful bow, her own head thrown back and eyes closed. The suction of his mouth against her sensitive nipples was enough to send her spiraling. She felt herself pulsing, clenching against his finger as her body began to throb in time with his movements.
Rachel crushed her breast to his mouth, needing it, needing all of it. More of it. "Oh Jack, Jack... fuck Jack..." she crowed, her cheeks flushing, her chest flushing.
There it was again, her using his name. Why was it affecting him this way? He dug his fingers deeper into her buttocks, playing with her body, bringing her right to the edge. Another night he would have teased her even longer, make her beg for release, take his fingers out of her completely, but not tonight. He kissed her tonight, they'd talked, she'd used his name.
For the first time - why now? he thought about sleeping with her, actually sharing a bed overnight with her, what it would be like to wake up with her - all why keeping his fingers pulsing in and out, his palm bumping her clit. He released her nipple to say, "Now, Rachel."
He was deeper and deeper in her with each stroke. She knew they were just fingers, they couldn't possibly be reaching deeper than the dicks she had taken--than her friend's dick she had in her just today. But it felt so somehow, his finger curling into her. And the pound, pound, pound of his palm against her clit. She could feel it striking that part of her like a timpani, ripples of pleasure moving throughout her crotch with each strike. She thrust against it, against his hand, pounding herself against him harder.
Rachel could feel something catching inside of her, a hitch in the engine, driving her into another gear. When the cool night air hit her nipple, and his now absent mouth told her 'now', she knew he was right. Of course he was right. He knew her and her body better than she did. She reached with her free hand and pinched that moist nipple, pinched it hard while she ground her mound against his hand, seeing stars. Her mouth opened but nothing came out, not even a breath.
He sucked on her nipple harder, he guessed, than anyone ever had, his mouth and fingers sensing the explosion now coming, hips bucking, her tight stomach muscles clenching and releasing, her gyrations out here by the pool such a contrast to the calm Tuscan evening. When she held her breath, he knew her release was just seconds away
In that last moment, Rachel forgot about Jack's cock, forgot about the Tuscan evening, forgot about the housekeeper who might be watching them from afar, forgot about her eventual return home, forgot about her father whose friend had his hands all over her body right now.
She seized the back of Jack's head with her suddenly free hand, pressed him tight to her full naked breast, grabbed onto his arm for balance, and came in multiple hard convulsions against his hand and around his fingers. She squeezed those fingers and she squeezed his head and she shook uncontrollably in his grasp as she came from toes to scalp in a way no man had ever made her, nor her own touch. She came in waves and when she was done she opened her eyes foggily to find herself still in his grasp.
In the twilight, his mouth looser on her nipple, her body in the throes of her orgasm, she of course couldn't see his grin. It wasn't a bemused grin, or a sly grin, just a smile that he was giving her so much pleasure. The intensity of her orgasm surprised even him. Of her many orgasms since she'd arrived in Tuscany, the first in direct response to his touch and his mouth.
He liked the sensation of her beautiful full tits bumping against her, the way her pubic mound thrust against his palm, the tight buttock muscles under his finger tips. He'd tell her later, or maybe tomorrow in the car during their day together, how her body was shaking, or maybe he'd let her tell her him how she felt. Rachel's pussy kept contracting around his finger, and he couldn't help but think about how delicious her tight pussy would grip his big thick cock when he did finally enter her.
When her body started to calm, her breathing started to slow, he dragged his finger out from her pussy, and he caught a glimpse of it glistening before he put that finger on the other nipple and rubbed her juice on it. He knew her nipples were extra sensitive after her orgasm, so he gave her nipple just a lick, tasting her cunt juice for the first time.
He hadn't forgotten about his cock, but now that her intense orgasm had passed, his cock reminded him that it was throbbing and needed relief. Before standing up, he brushed his palm against her pussy again, a new coating of wetness, and licked it, then stood up, caught a glimpse of Rachel's glossy eyes and then kissed her, wanting her to taste her pussy juice on his tongue.
It took Rachel a moment to begin to think clearly again--no, to think again at all. For a timeless period she only experienced her pulse, her pleasure centers, nothing else. The moment was prolonged by the little touches of Jack's hands and mouth, light now, but just enough to connect one moment to the next, to keep these aftershocks going. By the time she was really present again in time, Jack was standing and kissing Rachel.
Kissing her glistening lips. It was then she recognized the taste on her own mouth, the same taste he must have found on his palm, on her nipple, and dripping from its origin--her pussy. It was erotic, to have him share it with her, with his own lips, the unmistakable scent of femininity on this older man's lips.
And she realized it, only then, that this was a series of firsts for him as well. The first time to touch her like this, to suck on her breast, to know her taste. She kissed him back, kissed this man the age of her father, with no hesitation or irony, but simply out of lust.
Her hand found his cock again naturally, without thought. She felt its iron hardness and a part of her realized how eager he must be. She did not hesitate to stroke him as he had instructed her, but a bit harder, a bit faster, thinking he too must be ready to explode.
Jack considered himself, prided himself, on being a disciplined, patient lover. He took great satisfaction at teasing women until they were begging for release, that pleading pushing his arousal to its peak. He'd already fantasized about how we'd teach Rachel to give a long, slow handjob, with a healthy dose of dirty talk.
So why, then, did he now feel an unusual urgency in reaction to Rachel's touch on his cock? Why her? Why now? Was is it the kissing? This nagging question since she first arrived... am I developing feelings for her?
The last of the twilight was fading, the candles from the table where they'd had dinner flickered across her pretty face, the intimacy of their faces close, breathing each other's air, her tits pressed against him, his cock, whose throbbing had almost been put on hold while he focused on her, now jumping and twitching as she stroked him. The teaching moment about exquisite handjobs would have to wait for another time, because he now needed to release.
He bucked his hips toward her, together finding a rhythm. He broke their kiss..."Feels so good Rachel... I'm going to cum for you."
Rachel did not know the thoughts or plans that lurked in Jack's mind as he initiated all this tonight. Yet she noticed something change in him, felt some reverberation of his small loss of inner control. She could not know he had planned not to cum so easily, yet she recognized in him something like what she had been feeling herself--the rush of lust and orgasm that sweeps away any ability or even interest in stopping it.
It pleased her, she found herself smiling at the response her touch was having on him. She took a half step back so that she could look down and see what she was doing to him. One hand working his cock in a slow corkscrew, and now the other reached down and stroked his balls, scratching her nails along him, wanting to feel it as he came. She looked up into his face, hoping to see a flicker of loss of control, see that for once she wasn't the only one reeling.
The look on his face aroused her, inspired her hand. She jerked down to the base of his throbbing cock with harder strokes, fisting the head of his cock and letting it slide through her soft young palm. He would cum all over her if he came now, but she didn't care, so eager was she to be the one bringing him over the edge. "Cum for me, Jack," she breathed, looking into his eyes. She leaned up and ran her tongue over his lips, almost purring. "Cum on me."
Sometimes the turning point for the release is one little detail, a look, or motion, or a visual cue. This time they all arrived right after each other - the surprising scratch of her nails along his balls, the glance down at her big beautiful tits with their hard nipples, her tongue on his lips, and then her words, half instruction, half pleading, the distinction between cumming for her, and cumming on her. Yes, he'd cum on her once already that day, but this was different. This was her asking for it, and it was her hand and mouth and tits directly touching him that was making it all happen.
