First Date

The restaurant buzzed with evening chatter, ambient lighting casting a warm glow over the white tablecloths. Craig fidgeted with his watch, checking the time again as he scanned the entrance. His dating profile hadn't prepared him for the woman who walked through the door.

Heather moved with deliberate grace, her burgundy dress clinging to curves that drew every male eye in the establishment. Her dark hair cascaded past her shoulders, framing features that balanced between innocent and knowing. Craig stood awkwardly as she approached.

"You must be Craig." Heather extended her hand, her grip firmer than he expected. "I hope I haven't kept you waiting too long."

"Not at all." His voice cracked slightly. "I just got here myself."

A lie they both recognized.

Heather slid into her seat, crossing her legs slowly enough to draw his gaze. "I made reservations at three different restaurants tonight." Her crimson lips curved into a smile. "I like to keep my options open."

Craig signaled the waiter, desperate for a drink. "And what made you choose this one?"

"I wanted somewhere... intimate." Heather leaned forward, her neckline revealing just enough to make imagination necessary. "Somewhere we could really get to know each other."

Throughout appetizers, she maintained eye contact that bordered on inappropriate, occasionally biting her lower lip when he spoke. Her questions probed beyond first-date territory, inquiring about his fantasies, his preferences.

"You seem tense," Heather observed halfway through their entrées. She shifted her chair closer, their knees touching beneath the table. "You should relax."

Her hand found his thigh, fingers tracing idle patterns that moved steadily upward. Craig nearly choked on his wine.

"Problem?" Heather's expression was innocence perfected while her hand continued its exploration. Her thumb brushed dangerously close to his growing hardness. "Oh my," she whispered, eyes widening with mock surprise. "Is that for me already?"

Craig struggled to maintain composure as her fingers traced the outline through his pants. The waiter approached with dessert menus, completely unaware of the activity beneath the tablecloth.

"Two glasses of wine," Heather ordered without consultation. When the waiter departed, she squeezed gently. "Looks like someone's excited to get to know me better."

"Heather, we're in public--"

"And you're hard as a rock." Her voice dropped to a husky whisper. "Did that happen the moment I walked in, or did it take until my hand found your thigh?" Her fingers continued their torturous exploration. "I bet you're aching in those tight pants, aren't you?"

Heather's fingertips traced the rigid outline of Craig's cock through his jeans, the pressure light enough to be maddening. She maintained unwavering eye contact while her thumb circled the sensitive head, already detecting a small damp spot forming beneath the denim.

"I love how hard you are," she whispered, leaning closer. Her breath tickled his ear.

Craig's breathing quickened as her palm pressed firmly against his length, sliding up and down with deliberate slowness. The fabric created a tantalizing friction that made his hips instinctively push upward.

"Stay still," Heather commanded softly, her free hand reaching for her wine glass. "Don't make it obvious what I'm doing to you."

Her fingers curled around his shaft, squeezing rhythmically while maintaining the appearance of casual dinner conversation. Craig's cheeks flushed crimson as her hand worked faster, the outline of his erection straining visibly against his jeans.

"God, you're so hard," she purred. "I can feel every inch of you through these pants."

A young waitress approached their table, blonde ponytail bouncing with each step. Her name tag read "Tiffany."

"Are you ready to order your main courses?" Tiffany asked brightly, pen poised over her notepad.

Heather's hand never stopped its rhythmic stroking. "I'll have the filet mignon," she said smoothly. "Medium rare."

Craig opened his mouth to speak just as Heather's thumb pressed firmly against the sensitive underside of his cock head. His voice caught in his throat.

"Sir? What would you like?" Tiffany's cheerful smile never faltered.

"He'll have the..." Heather began, increasing her pace beneath the table.

"I can order for myself," Craig managed, his voice strained. He gripped the edge of the table as Heather's fingers traced his length with exquisite pressure. "The, um, salmon please."

Tiffany scribbled on her pad. "How would you like that cooked?"

Heather's palm pressed harder, moving in tight circles over the head of his cock. Craig's thighs tensed as pleasure surged through him.

"Medium," he choked out. "Medium is fine."

"Perfect! I'll be back with your orders soon." Tiffany collected their menus and departed, completely oblivious to Craig's predicament.

"You handled that well," Heather whispered, her hand now rubbing his entire length with firm, determined strokes. "But I felt you throb when she was looking at you. Did that turn you on, being touched while she watched?"

Craig's eyes widened and he shook his head slightly. "That's not--I wasn't--"

"Shh." Heather leaned closer, her lips brushing against his earlobe while her hand maintained its torturous rhythm beneath the table. "It's okay to admit it. The thrill of almost getting caught is... intense."

Craig swallowed hard, his cock twitching against her palm as she squeezed harder. His attempted denial dissolved into a suppressed groan.

"I have a confession to make," Heather whispered, her voice dropping to a husky purr. Her fingers traced the swollen head of his cock through his pants, feeling the growing dampness there. "I absolutely love making men cum in their pants. It's my biggest turn-on."

Her hand increased its pace, working his shaft with deliberate, skilled movements.

"So I really hope you have some stamina, Craig," she continued, her eyes glittering with mischief. "Because I'm not going to stop until our food arrives."

Craig's breathing quickened. "Heather, I can't--"

"Even if you're close," she interrupted, her thumb circling the sensitive head. "I won't stop. So unless you want to spend the entire meal with your underwear filled with warm cum, you'd better show some restraint."

The wicked smile playing on her lips betrayed her true intentions. Her fingers worked faster, squeezing and stroking with precision. She wanted to feel him lose control, to watch his face as he fought--and failed--to maintain his composure in public.

"The kitchen seems backed up tonight," she observed innocently, glancing toward the kitchen doors. "Might be a while before our food comes out."

Heather glanced around the restaurant, noting the dimmed lighting and strategic positioning of their corner table. With a predatory smile, her fingers moved to Craig's belt buckle.

"What are you--" Craig's eyes widened in alarm.

"Shh," she whispered, deftly unfastening his belt. "Nobody can see under the tablecloth."

Her nimble fingers worked his button open and slowly dragged his zipper down, the sound nearly imperceptible beneath the restaurant's ambient noise. Craig's breathing quickened as cool air hit the thin fabric of his underwear.

"Heather, this is too much," he hissed, but made no move to stop her.

"Poor thing," she cooed, sliding her warm hand beneath the waistband of his boxers. Her fingers wrapped around his bare cock, already slick with precum. "Oh my, you're absolutely dripping."

Craig bit his lower lip as her hand established a slow, torturous rhythm, her palm gliding over his sensitive head before stroking down his full length. The direct skin-to-skin contact sent jolts of pleasure through his body..

"I've been thinking," she murmured, her lips brushing against his ear while her hand continued its relentless stroking. "Our little waitress Tiffany should be back with our food soon."

Her grip tightened slightly, her rhythm deliberate and measured.

"I might just keep you right on the edge until she arrives," Heather continued, her eyes dancing with wicked delight. "Then I'll make you cum while she's standing right here."

Craig's eyes widened in horror. "Heather, please don't."

"Just imagine her watching your face," she whispered, her hand speeding up. "The way your expression will change when you're cumming. The way your eyes will roll back, the little gasp you'll make."

"Please," Craig begged, his voice strained and desperate. "Not like that. Not in front of her."

Heather's smile only grew more predatory as her hand worked his cock with increasing urgency.

"Heather, I'm serious," Craig pleaded, his face flushed with equal parts arousal and embarrassment. "Please don't."

Heather's pace quickened dramatically, her hand becoming a blur of motion beneath the tablecloth. The wet sounds of her palm sliding over his precum-slickened shaft were thankfully masked by the restaurant's ambient noise.

"Look at you," she whispered, her eyes alight with mischievous delight. "Meeting me for the first time tonight, and already I've got my hand wrapped around your cock under a restaurant table."

Craig's knuckles turned white as he gripped the edge of the table. His breath came in short, shallow gasps.

"What would people think if they knew?" Heather giggled, her voice playful yet laced with erotic menace. "Proper, buttoned-up Craig, getting jerked off by a woman he's known for all of forty-five minutes."

Her wrist twisted on the upstroke, and Craig's thighs began to tremble uncontrollably.

"Ohhh," she cooed, feeling his cock twitch against her palm. "Is someone getting close already?"

Craig bit his lower lip, eyes darting nervously around the restaurant. "Heather, don't--"

"Don't what?" She giggled again, the sound innocent yet utterly devious. "Don't stop? Don't go faster?" Her hand maintained its relentless rhythm. "Remember what I said, Craig. I'm not stopping."

His cock pulsed visibly in her grip, and she felt another surge of precum coat her fingers.

"So unless you want to cum in your pants on our very first date," she teased, her voice lilting with amusement, "you'd better find some self-control."

Her free hand reached for her wine glass, taking a casual sip while her other hand continued its merciless stroking beneath the table.

"Though I have to say," Heather added with another light, bubbly giggle, "the thought of you sitting through dinner with cum-soaked underwear is absolutely delicious."

Craig's breath hitched as a particular twist of her wrist sent a shockwave of pleasure through him.

"Oh! Did you like that?" Heather's eyes widened with mock innocence, her giggles growing more frequent. "Your cock just got even harder! I can feel every little twitch."

Heather's hand worked mercilessly beneath the tablecloth, her fingers slick with Craig's precum as they glided along his shaft. The unmistakable click of heels against tile announced Tiffany's approach, and Craig's eyes widened in panic.

"Heather, please--" he whispered urgently.

Heather's response was a wicked grin and a sudden change in technique--her wrist rotating in tight, rapid circles while her fingers maintained their vise-like grip on his cock. The sensation was overwhelming.

"Here we are!" Tiffany announced cheerfully, arriving with their plates balanced expertly along her arm. "The filet mignon for you, ma'am, and the salmon for--"

Craig's back arched involuntarily as Heather's hand delivered a particularly devastating twist. The pressure that had been building in his balls suddenly exploded. His cock pulsed violently in Heather's grip as the first thick rope of cum erupted, soaking the front of his boxers.

"Sir? Are you alright?" Tiffany asked, though her innocent tone didn't match the knowing look in her eyes.

"He's fine," Heather answered smoothly, never ceasing the frantic twisting motion of her hand. "Just... excited about the food."

Craig's face contorted as another powerful pulse sent more hot cum flooding into his underwear. The warm stickiness spread across his groin as rope after rope pumped out, completely beyond his control. He bit his lip to stifle a groan as his hips jerked slightly beneath the table.

Tiffany set the plates down and glanced between them, her ponytail bouncing as she tilted her head. A smile spread across her face as she addressed Heather.

"Big sis, are you doing the thing again?"

Heather's eyes sparkled with mischief. "Of course."

Craig's jaw dropped in shock, even as another pulse of cum surged from his cock, creating a visible wet spot that began to seep through his pants.

Tiffany leaned in, lowering her voice conspiratorially. "Is he cumming right now?"

"So much," Heather confirmed, her hand still working beneath the tablecloth as Craig's entire body trembled. "He's making quite a mess."

Tiffany's giggle was light and musical as she turned her attention directly to Craig, whose face burned with embarrassment.

"So tell me," she asked, her innocent server persona completely abandoned, "how frustrating is it having my big sister make you cum in your pants like that?"

Craig couldn't answer. His underwear was now thoroughly soaked with what felt like an endless flow of cum, the warm stickiness clinging to his skin as Heather's relentless hand continued to milk every last drop from him.

Heather slowly withdrew her hand from beneath the tablecloth, her fingers glistening with thick, pearly cum. Instead of reaching for a napkin, she held it up between herself and Tiffany, displaying the sticky evidence of her handiwork.

"Look at the mess he made," she said with a triumphant smile.

Tiffany's eyes widened as she stared at her sister's cum-covered fingers. "Oh my god, Heather!"

Craig wished he could disappear into the floor as Heather brought her fingers to her lips and slowly, deliberately licked a streak of cum from her index finger. Her tongue swirled around each digit, collecting every drop while maintaining eye contact with him.

"Mmm," she hummed appreciatively, sucking her middle finger clean. "Not bad at all."

Tiffany shook her head, her ponytail swinging. "You are so mean, Heather! Look at his face! He's mortified!"

Craig sat frozen, still reeling from his intense orgasm and the humiliating realization that both women were fully aware of what had just happened. The warm wetness in his underwear was quickly cooling, becoming an uncomfortable reminder of his lack of control.

"That's what makes it fun," Heather replied, licking the last traces from her thumb.

Tiffany gave Craig a sympathetic yet amused look. "Enjoy your dinner," she said with a barely suppressed laugh, then turned and walked away, her hips swaying as she disappeared among the tables.

Heather leaned back in her chair, regarding Craig with undisguised satisfaction. The corners of her mouth turned up in a predatory smirk.

"That," she declared, "was one of the biggest cumshots I have ever seen. Your poor underwear must be absolutely soaked." She picked up her fork and knife, cutting into her steak. "And just so we're clear, you're not allowed to go clean yourself up."

Craig's eyes widened. "What? But I can't--"

"You can and you will," Heather interrupted firmly. "You're going to sit there in your pool of cum for the entire meal." She took a bite of her steak, chewing slowly before swallowing. "Consider it part of our date experience."

Craig shifted uncomfortably, the sticky wetness clinging to his skin. His pants had a visible damp patch that he desperately hoped wouldn't be noticed by other diners.

"I'm done for," he muttered, reaching for his water glass with a shaky hand.