date-night-extended-version
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Date Night Extended Version

Date Night Extended Version

by eding8667
19 min read
4.22 (24500 views)
adultfiction
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Dana stared at the soft glow of the vanity mirror. Her reflection gazed back, a woman she barely recognized anymore. Her hand moved in practiced motions. The ritual was comforting in that respect, simple and familiar. Tonight, though, wasn't about routine. She faced the truth. A truth that she wasn't quite prepared to admit to herself.

Every stroke of the makeup brush felt weighty, as if it held deeper meaning. As the blush tinted her cheeks, she couldn't help but feel the weight in her emotions. As Dana delicately applied her mascara, she knew very well that Jack wouldn't appreciate the details. He never did. He wasn't supposed to.

But she could pretend.

Her son. Her Jack. How had it ever come to this? She would never deny the love that ran deep between them. it was there from that first breath he'd ever taken. Somewhere along the line, though, something had... changed. It wasn't supposed to, but it had. And now it was like an elephant in the room, and she couldn't pretend it didn't make her heart race when they were in the same room.

She longed for him in a way that terrified her.

It had started innocently enough. Dana had been severely depressed. Jack had seen it and suggested that he take her out on mother/son dates.

"Let's go out, Mom," he had said, in a voice full of innocent compassion. "Just you and me. Let's get you out of the house."

He had noticed what her husband had failed to. Dana was losing herself as her marriage seemed to be dying. Herb seemed to be retreating into himself. Drifting further away from her every day. They hadn't been intimate in more than two years. The fire had not only cooled between Dana and Herb, but it had gone out. The loveless bed that they shared day after day had only added to her heartbreak.

Her mind turned to the dinners and outings of the past few months, the dates. It had been just the two of them, Dana and Jack. Jack had seen that she had been in pain, and he'd stepped in to fill the void. He had also filled her heart.

It had all been so innocent and pure. Jack would take her out to dinner, maybe to a movie. They would talk and laugh, and for a few brief hours, Dana felt alive again. Not as a mother, not as a wife, but as a woman. She hadn't realized how much she'd needed that, how much she'd missed feeling seen, until she had it again.

With each date, something began to shift within her, something she couldn't name at first. Her heart would react to the sound of his laughter, and to the gleam in his eyes when he told a story. She started to look forward to their dates with an excitement that felt, different. It was like being young again when she and Herb had begun dating.

Seated in front of her mirror, reality weighed heavily upon her. For the first time, even if only in the privacy of her heart, she admitted the truth to herself. She had fallen in love with her son. The older, innocent maternal love was there too, but now there was more. Something she didn't dare speak aloud. Something that she knew was wrong, yet couldn't bear to give up.

She wasn't naive.

She knew Jack didn't feel the same way. For him, he was just keeping his mom company, seeing her through what he assumed was a bad stretch. He couldn't know what it meant to her. He didn't understand these were the nights she lived for. That she prepared for them as though she were a woman in her 20s, preparing to spend an evening with her man. She had selected her clothes carefully, matching it with the very sexiest lingerie. Though he would never see it.

She did admit to herself, privately, that she wished that he could.

She closed her eyes, willing herself to keep control of her racing thoughts. It wasn't his fault. Jack was tender, thoughtful, as Herb could be, if he were still willing. Jack had stepped into a position that was not his to fill, but he had done it out of love. Pure love, not the teenage like infatuation that seemed to consume Dana. In her loneliness, Dana had let herself hope for things that could never be.

Her eyes strayed back to the mirror. Although she was no longer a young woman, there was a beauty about her. She did, she supposed, look pretty damn good. At 5'6", she was a little taller than the average woman, but her long thin frame gave her feminine shape an extra emphasis. Her long dark hair, tied back in a pony tail, framed her delicate face. She knew that she was beautiful, to any men who looked.

Herb wasn't looking anymore. But when she was with Jack, she felt seen. Even if he didn't know what he was seeing.

For Jack, it had been a simple and uncomplicated love, the love of a son for his mother. Dana, though, had crossed an emotional line, one she could never come back from. She would keep it buried. For his sake. For hers.

Finishing her work, she put her makeup away, her hand trembling just a little. She would smile. She would laugh, listen to his stories, and pretend everything was all right. She wouldn't let her muddled heart ruin the evening.

Because Jack didn't need to know. He couldn't.

Yet, even knowing that and fully understanding the lines that must never be crossed, Dana allowed herself a flicker of hope.

She was dressed sensibly for their date that evening. They were going to the county fair, so she was in tight jeans, with a warm flannel shirt and a stylish pair of knee-high boots. She smiled to herself. She looked sexy.

Guilt prodded Dana. Herb didn't know about any of this. Her feelings, her selfish daydreams of unattainable love. He couldn't know. This wasn't about Jack trying to cheer her up anymore. It went deeper, something that couldn't be said, not to him, not to anyone.

Herb trusted her. He still loved her. The fact was that she loved him too. If he gave her even the smallest bit of what she desperately needed, she wouldn't be so drawn to something so wrong.

At the front door, Jack was waiting, smiling in that warm, easy way he always did. Radiating that effortless charm he'd had since he was a boy. He was so like Herb that way... well, so like Herb used to be.

Dana and Jack were riding the Ferris wheel as it creaked to a soft stop, leaving them suspended high above the county fairgrounds. The distant hum of laughter, and the smell of cotton candy and fried foods wafted upwards towards them. Up here, everything seemed still. They were in a world all of their own. The fading light of the sunset bathed the horizon in a soft, golden glow.

Dana leaned back in her seat, the worn vinyl squeaking softly beneath her. She craned her neck to take in the view. It was amazing. The moment was perfect. She turned towards Jack to say something. She would never remember what she had meant to say in that moment.

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But before she could speak, he too turned, perhaps reacting to her movement. Their faces came together in the most natural way. Lips met lips, unplanned, undiscussed. It was as though the universe ordained the moment, and they were merely actors caught up in its web.

It was gentle at first. A brushing of lips, unsure, yet electric. For an instant, time seemed to stand still. Nothing else mattered. There was no Ferris wheel, no fair, no one else in the world existed but them. Neither pulled back, it was as if they feared that something precious might break. Their lips moved together, and the kiss became more deliberate. Their kiss deepened, at first with tenderness, with love, then with need.

His hand, almost reflexively, caressed her cheek, his fingers grazing the soft curve of her jaw. Her body pressed towards his, her arm going around him and pulling him tight against her. Their kiss deepened, filled with longing and desire, from both of them.

Heat spread through Dana's body like fire, starting at her lips and spreading all through her body. This wasn't just a kiss. It was raw, potent, and savage. Her toes curled, the intensity of her desire sending shivers down her spine. She could feel her heart hammering wildly in her chest. It was overwhelming, as if something inside of her had just woken up for the first time.

Jack, too, felt the sudden rush. It was a shockwave of desire and of something deeper, more profound. His heart too was racing. He hadn't anticipated this, hadn't even realized he was waiting for this until it happened. The kiss wasn't hurried, but it was profound. It laid bare every unsaid thing between the two of them, all the feelings that had simmered beneath the surface.

Eventually, the kiss ended as naturally as it had begun. They drew back, only partially. Their foreheads were resting against each other's, and their noses were still lightly touching. Their vapor from their breath mixing in the chilly evening breeze. Neither spoke. Something significant had just passed between them.

In the quiet solitude, high above the fair, nothing had changed except everything.

The Ferris wheel finally kicked back to motion and they creaked slowly towards the ground.

The earth beneath Jack's feet felt solid, but his mind remained in the clouds. He could still feel it. He remembered the heat from his mother's lips, the feel of her body against his. His mind boggled at the way everything stilled for that single, infinite moment. He walked hand in hand with his mother as they wandered the fair, his thumb lightly caressing the back of her hand. He realized that he truly loved her. Not just as his mother, but as a desirable woman.

He looked over at her, the woman who had raised him, the colorful lights of the carnival casting her upturned face in a variety of colors. She looked a bit lost in her thoughts, a faint flush colored her cheeks. He hadn't spoken since they'd gotten off the Ferris wheel, and neither had she. Words didn't seem important now. What had happened up there was too fragile, too new, to disturb with conversation.

That kiss... it had changed everything. He'd convinced himself, for months, what he felt for her was simple, straightforward. He and his mother were close, she was going through a hard time, and he was just there for her. That was all. It could be nothing more.

And yet, that kiss.

His stomach twisted in a way that wasn't unpleasant. Something in him had shifted when their lips had met. Up to that moment, the moment of the kiss, he had been telling himself that what he was feeling was just normal affection. He knew that there was no going back.

Jack was still replaying the kiss in his head when he heard a voice he knew well cut through the noise.

"Hey, Jack!"

He blinked and looked up to see his friend Mark threading his way over toward them, grinning like an idiot. Jack's heart sank.

Jack had told his friends, including Mark, about the time that he had been spending with his mother. He had been clear that it was to cheer her up and help her. But Mark had been on his case for several weeks about how much time he'd been spending with her. He had teased Jack about his "girlfriend." It had irritated Jack to no end. And here Mark was, seemingly intent on embarrassing both Jack and his mom.

Jack's pulse raced, knowing full well what was about to happen before Mark had even opened his mouth.

"Hey, Jack! This must be your girlfriend Dana you've been talking so much about!"

Jack could feel his face burn with his embarrassment. As the words hung there, a familiar ball of annoyance constricting his chest. He was about to roll his eyes and give his usual exasperated response. But then he felt Dana's hand tense just a little in his. He turned to her and saw it. A flush was creeping up her neck, her eyes were widening. It was obvious that she was feeling hurt and surprised.

Dana hadn't known he'd been talking about her, that his friends knew that he was taking her out. She was suddenly unsure, wondering just what Jack had been saying. She had no idea of the razing that Mark had been subjecting Jack to. She suddenly wondered what Jack had been saying about her, and she started to pull away.

It was a pivotal moment. Jack could sense it. Dana was uncertain and afraid. On impulse, He leaned towards Dana without thought or hesitation. She turned just a little, her eyes wide and questioning, but she didn't back away. He cupped her cheek in his hand and pressed his lips to hers, softly this time. It was a tender, but clearly not platonic kiss.

When he drew back, his voice was calm and steady, "Yes, that's right."

Dana's blush deepened and her eyes blinked rapidly. Something in her gaze told him she wasn't upset.

Mark didn't have a snarky response for once. With an awkward laugh, his grin faltering, he said, "Uh, okay, well, I'll... catch you later,". Mark backed away, quite clearly flustered.

Mark was swallowed into the tide of humans in an instant. Jack gave his mom a sheepish grin, then they both burst out laughing.

She was his girlfriend. It wasn't just an off-color office joke anymore. It was wrong. He knew it was wrong, and he didn't care. It was wrong, but undeniable. She loved him as he loved her. Standing there, surrounded by the laughter of strangers, Jack turned to her, and he pulled her close.

Putting his mouth close to her ears, he asked, "Would you like to get out of here?" his voice pitched just for her ears.

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Dana nodded. "Take me to your place."

Jack smiled, studied her face a moment, and kissed her again.

The second Jack made the turn into the well-known parking area of his apartment, his heart skittered. She had been here a million times. Between dinner visits, afternoons spent helping him set up furniture, even a few nights when she stayed over after a long day, but this was different.

Only when they were outside his front door did he look at her, unsure. His confidence suddenly was replaced by a new fear. What if he was misunderstanding? She clutched his hand in hers as they walked and gave him a reassuring smile.

His heart was thundering. He could still feel the softness of her lips. Her taste lingered in his mouth. She tasted like cherries and cotton candy.

Jack brought his date through his apartment door, tenderly holding her hand. He closed the door firmly behind them, then pulled her against him, and kissed her.

It started slow, tentative. Their lips softly exploring one another, their arms pulling them tightly together. Gradually, the kiss gained passion, their tongues dancing. Jack could taste her again. His excitement pressed into her belly. Their hands exploring as their kiss continued. Jack wondered idly what she tasted.

Somehow, they made it to the bedroom. She had been in here before, but never in this context. The clothes were quickly shed, the kiss seemingly uninterrupted as they found themselves naked together on the bed.

Jack's lips moved from hers down to her neck, where he licked and sucked eagerly. He was sure that he left a few hickies, but they could worry about that later. His kisses moved downwards. Briefly, he nibbled and suckled on her nipples. They were his. They had always been his, and it filled him with joy to have them in his mouth again.

Slowly he kissed, sucked, and nibbled his down her belly towards her holy of holies. Unsurprisingly, it didn't look like she had been expecting this outcome to the date, as she hadn't groomed or trimmed her pubic region at all. Jack didn't care. He found her bright pink lower lips and tenderly licked them from bottom to top, slipping his tongue into her just a bit. She shuddered under him, moaning.

After another few slow, teasing strokes of his tongue Jack finally attacked her pussy with gusto. He made his tongue swim through her, stroking and licking her labia and clit, causing her moans and cries to increase in intensity. Her noises inspired him, encouraged him, and filled him with even more desire.

As he licked and sucked her clit, he slipped a couple fingers inside and tenderly rubbed the special spot just beneath her clit. The resulting orgasm caused her body to shudder and shake, and her screams were so loud that Jack worried that someone might call the police.

Her hands pushed him away for a few moments as she caught her breath. Jack crawled back up her body, giving her more kisses as he moved upwards. Her eyes were closed as his lips met hers again. His cock was as hard as it had ever been, and it was brushing eagerly against her wet heat.

Her eyes opened, and their eyes met. "Are you sure that you want this?" She asked in a quiet voice. Her shy demeanor in stark contrast to the scent in the room and the sweat covering her naked body.

"Yes, Mom. More than anything." he told her.

She smiled her shy smile. Then she tenderly bit her bottom lip with the most adorable expression of all time and nodded. "Me too." She told him.

Jack felt his mother's hand guiding his cock inside her, he pressed slowly into the birth canal from which he had originally emerged. He entered his mother slowly, both savoring the sensation, the joy of the moment. It was only moments before he was fully inside his mother sexually for the first time. The significance of the moment wasn't lost on either of them.

Her arms wrapped up under his, pulling his chest against her breasts. Their lips met again, hungrily, as he began stroking his cock in and out of his mother's sweet cunt. Their sweat covered bodies slid together, the skin of their crotches slapping together loudly as he began fucking her with purpose.

As his fucking intensified, her legs wrapped around his ass, pulling him deeper. She disengaged the kiss and she began to pant and moan. Her voice rising in tone and volume. She cried out in pleasure as he slammed deep inside her.

Jack was afraid that one of his neighbors would hear her, but also hoping that they might. The sounds that she was making were obviously sexual in nature, filled with her pleasure. He was proud to be inspiring this reaction from his mother.

As his arousal intensified his strokes became more intense, more primal.

Jack felt his mother shudder under him and around his cock as another orgasm rocked her. She screamed her joy and pleasure as she called his name, and he emptied his balls into his mother's willing womb.

The morning sun filtered delicately between the blinds. Dana blinked into wakefulness. The warmth of her body was cocooned in the cozy bed. Familiar city sounds stirred just outside. She was confused for a moment, caught between sleep and wakefulness. But with insistent gentleness, memories of the night before began to surface.

Dana looked down at herself. She was naked beneath the sheets. Her heart beat a slow steady beat. She hadn't felt this way in so long. She felt content, relaxed, and somehow whole. She turned her head to see Jack lying beside her, his body half-covered, his chest rising and falling with the rhythm of sleep.

A tide of feelings, warmth, satisfaction, and quiet happiness filled her. The tension and confusion that had clouded her mind the night before had gone. A soft smile overspread her face as her heart swelled.

She had expected to feel guilt. Maybe disgust or regret. She felt none of those things.

The night had been wonderful. There was simply no other word for it. Whatever lines had been crossed, whatever boundaries blurred, no longer seemed to matter. There had been no hesitation, no second-guessing. Just the two of them, moving together like it was the most natural thing in the world.

She hadn't known just how much she had needed that, the feeling of being wanted, cherished, and desired, until it had happened. She had been so empty. Jack had filled her, in so many ways, she thought with a quiet chuckle.

She watched the angle of Jack's jaw, the way his hair lay in tangled disarray across his forehead. He seemed so peaceful, so much the boy she had raised, yet so very different. He was no longer just her son. Jack was her man now. The man who had held her through the night, who kissed her and loved her as she had so desperately needed.

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