Chapter 6: First Date
The air outside the speakeasy was crisp with the faint bite of approaching autumn, the kind of night that made Margot pull her leather jacket a little tighter around herself as she stepped out of the Uber. The doorman, dressed impeccably in a tailored suit, inclined his head in greeting, his expression one of practiced neutrality that bordered on hauteur, as if to say, *Yes, you belong here.* The soft murmur of conversation and the occasional clink of glass from inside the bar wafted out through the open door, wrapping around Margot like a warm, invisible shawl.
The speakeasy’s light spilled onto the sidewalk in a golden rectangle, the glow catching the silver spikes on her heels and making them glint like tiny stars. Margot paused at the entrance, her fingers tightening around the leather strap of her clutch for just a moment. She took a slow breath in through her nose, letting the cool night air settle in her lungs—pine, distant traffic, and the faint metallic tang of the harbor. *
* Inside, the lounge was bathed in a moody amber glow—a mix of candlelight, Edison bulbs, and polished brass. The air smelled of aged whiskey, aged oak, and something faintly erotic, like the subtle musk of skin heated by velvet and desire.
Margot stepped inside, her black leather jacket whispering against the fabric of her dress as she moved. The emerald pendant glinted between her breasts with every step, catching the low light like a beacon.
She scanned the lounge, her green eyes sharp and assessing. The indoor seating area was filled with well-dressed patrons leaning into dim light, their conversations a low hum beneath the murmur of live jazz filtering through hidden speakers. A few eyes flickered toward her—men’s gazes lingering just a second too long on the V of her dress, the flash of her legs beneath the hem. Women’s eyes assessed her with quiet curiosity or mild envy, their own outfits more conservative by comparison.
Margot ignored them all.
If she lingered on anyone’s reaction too long, she might lose her nerve. Instead, she moved with deliberate purpose toward the far end of the bar where a single stool was still unoccupied, its high back upholstered in dark leather that matched the booth banquettes. The bartender, a man with silver-streaked hair and sleeves rolled up to his elbows, paused mid-pour to glance her way—just long enough to confirm her interest before nodding once in acknowledgment.
She settled onto the stool, crossing her legs with a slow deliberation that made the dress ride high enough to hint at what lay beneath. The leather creaked softly under her weight.
She slipped her clutch onto the bar and let her fingers trail along the polished mahogany edge, savoring the slow burn of anticipation simmering in her chest. The emerald pendant glinted between her breasts, a quiet threat to the modesty of her posture.
The bartender approached, his expression smooth but not unkind. "Whiskey, neat," Margot said before he could ask. "Knob Creek."
Her voice carried the kind of certainty that made him nod without hesitation. He turned toward the wall of amber-scented decanters, pouring two fingers of the bourbon into a heavy crystal glass.
She looked toward the door and saw Jake entering the bar. The contrast between his tailored navy suit and the raw magnetism of his presence was jarring in the most delicious way. His jaw was shadowed with stubble, and his dark hair was tousled as if he’d just raked his fingers through it, the way he did when he was thinking deeply. The crisp white shirt strained slightly over his shoulders as he moved, revealing the faintest hint of tattoo ink curling beneath the cuff.
Margot didn’t turn away.
She let her gaze linger—just long enough to be noticed, just long enough to make him feel seen.
A slow, knowing smile tugged at the corner of her mouth.
Jake locked eyes with her across the room. He froze for a minute, and she could see his eyes widen in appreciation as he took in her appearance.
He turned from the host stand and began making his way through the crowd, the amber light of the bar highlighting the sharp angles of his face and the confident stride of his gait. The speakeasy seemed to quiet slightly as he passed, the murmur of conversation dimming just for a second before resuming—like a collective breath held and then released.
Jake moved with the easy grace of a man who was used to being watched but not controlled by it. His navy suit hugged his broad shoulders, the fabric whispering against itself with every step.
Margot didn’t look away as he approached, her fingers tracing the rim of her whiskey glass, the crystal cold against her palm.
The ice cubes clinked softly as she swirled the amber liquid, watching Jake’s reflection in the polished brass rail behind the bar. His gaze didn’t leave hers—intense, assessing, hungry. The kind of look that made her skin prickle with anticipation.
He stopped a few feet away, close enough to invade her personal space but not close enough to touch. Margot tilted her head slightly, her lips curling into a slow, deliberate smile. The emerald pendant swayed between her breasts with the movement, catching the dim light like a warning.
Jake's eyes flickered down for the briefest fraction of a second, drawn to the valley of her cleavage and the faint outlines of her nipples beneath the black dress.
When his gaze lifted back to meet hers, there was no apology in it—just a raw, unapologetic hunger that made Margot's pulse quicken.
"Margot," he said, his voice rough with restraint. "You look absolutely incredible."
The bourbon in her glass caught the hazy light as she lifted it to her lips, taking a slow sip that gave her time to study him before answering. The whiskey burned pleasantly on its way down, grounding her in the moment.
"Jake," she replied, her voice equally steady. "I was beginning to wonder if you were going to make me wait all night."
His lips twitched at the corners, though his eyes remained dark with intent.
Jake stepped closer, the heat of him tangible even before he leaned in. His aftershave was something smoky and spicy, bourbon-soaked into his skin after a long day at the office. "You *know* I wouldn’t keep you waiting."
Margot exhaled a quiet laugh, the sound rich and knowing. She set her glass down with deliberate slowness, the crystal chiming softly against the bar. "Flatterer. I could have been gone by now."
"Yeah?" Jake murmured, leaning in just enough that she could feel the whisper of his breath against the shell of her ear. "And where would you have gone?"
Her pulse jumped.
The tip of his nose grazed the sensitive skin beneath her lobe, the contact feather-light yet electric. Margot tilted her head slightly, inviting more, though she kept her voice even. “Nowhere important.”
Jake hummed, low and satisfied, as if that answer pleased him more than any likely destination. His fingertips grazed her knee where the dress had ridden up, and Margot felt the contact like a brand through the thin fabric. She didn’t pull away. Didn’t flinch. The speakeasy seemed to fade around them—just the two of them, the dark wood bar, the faint hum of conversation holding its breath somewhere beyond the edge of their world.
Jake’s touch on her knee was possessive in the way it lingered, his thumb tracing slow, deliberate circles against her bare skin. Margot let her whiskey glass sit forgotten, her attention fully on the way his breath warmed her neck, on the faint scent of leather and bergamot clinging to his skin.
"You know," Jake murmured, his voice rough with intention, "the first time I saw you in the office, I thought, *She belongs on a stage, not a conference table.*" His lips hovered near the sensitive skin beneath her ear, his breath hot against her pulse point.
Margot arched her neck slightly, giving him better access, her fingers tightening around the edge of the barstool.
"Mmm. And now?" she asked, her voice barely above a whisper, the bourbon still clinging to her tongue.
Jake’s fingers slid higher along her inner thigh, the pressure of his touch deliberate, teasing. The emerald pendant swayed as she shifted, the green stone catching the dim light like a secret. "Now I think you belong in my bed."
A soft laugh escaped her, breathy and knowing. "What if I have other plans?"
His thumb brushed her pubic hair, shocked to find she wasn't wearing any panties. Margot’s breath hitched.
The speakeasy’s low murmur faded entirely, as if the world had narrowed to this single point of contact, this single promise of what came next.
Jake’s fingers curled around the hem of her dress, slowly lifting it inch by inch until the cool air of the bar teased the bare skin of her upper thighs. The fabric pooled at her waist, leaving her exposed in a way that should have been indecent but felt only thrilling. His gaze dropped, drinking her in—the glisten of arousal already slicking her lower lips, the way her thighs tensed in anticipation.
“Fuck,” Jake exhaled, low and rough.
His fingers had stilled against her thigh, his thumb pressed just shy of where she was already wet and wanting. Margot didn’t stop him. Didn’t shift away. She simply let him feel the heat of her through the thin layer of fabric, let him see how badly she needed this—how badly she needed *him*—tonight, in this bar, with the jazz pressing in around them like a secret.
“You’re not wearing anything under that dress,” Jake said, his voice rough with realization.
Margot smirked, tilting her head to meet his eyes.
“I was hoping you’d notice.”
Jake groaned, his fingers flexing against her skin before he finally gave in to the pressure. He slid his hand between her thighs, no longer teasing, no longer asking—*taking*. His fingertips found her slick and ready, already swollen with need. Margot bit her lip as he traced the seam of her, slow and deliberate, savoring every gasp she tried to stifle.
The bar’s dim lighting caught the emerald pendant as she arched slightly, the stone now nestled between her breasts, glinting like a promise. The whiskey glass tipped dangerously on the bar, forgotten, ice melting into nothing. She didn’t care.
The noise of the speakeasy faded completely when Jake’s fingers finally parted her slick folds, exploring her with rough precision. His thumb circled her clit with just the right amount of pressure—wet, deliberate, unrelenting. Margot’s breath came in shallow pants, her nails digging into the barstool’s leather as she struggled to stay quiet.
Jake leaned in close, his lips brushing against her ear. “You’ve been thinking about this for weeks, haven’t you?”
Margot didn’t answer. Instead, she tilted her head back, giving him better access as his fingers worked her with growing urgency. The emerald pendant swayed with the movement, glinting between her breasts like a dark secret.
Margot’s eyelids fluttered shut as Jake’s fingers worked her with relentless precision, his thumb circling her clit in slow, delicious circles that made her thighs tremble. The bourbon glass tipped further, half-empty ice cubes clinking softly against the mahogany. The jazz saxophone’s sultry notes wrapped around them like a second skin, the melody syncing perfectly with the rhythm of Jake’s touch.
Margot’s breath hitched when his fingers suddenly slid lower, two of them pressing inside her with a slow, deliberate thrust. She bit down on her bottom lip to stifle a moan, her knuckles whitening around the edge of the stool.
The emerald pendant swayed between her breasts with every shallow breath she took, the green stone glinting like a tiny beacon in the dim light.
Jake’s mouth hovered just above her ear, his breath hot and ragged against her skin. “You’re so wet for me,” he murmured, his voice rough with satisfaction. His fingers curled inside her, pressing against that sweet spot that made her vision blur at the edges. Margot let out a soft whimper, her hips shifting slightly in invitation, her thighs parting just a little wider.
The high back of the barstool kept her upright, her spine arched, her body on display in ways she had only ever imagined. The emerald pendant dipped lower with her breath, the cool stone brushing against her collarbone as her chest rose and fell in quick, shallow bursts.
Jake’s fingers worked her with agonizing precision—one moment slow and teasing, the next swift and demanding. His wrist twisted slightly, the heel of his palm grinding against her clit with each inward stroke of his fingers. Margot’s free hand flew to his chest, her nails digging into the fabric of his suit jacket, the only anchor in the storm of sensation threatening to drown her.
Margot glanced up and saw the bartender looking at her from across the bar. He caught her eye and winked letting her know he knew what was going on.
Margot’s breath hitched when she saw the acknowledgment in his expression. The emerald pendant swayed as she tilted her head back further, her throat exposed to Jake’s lips. His mouth found the sensitive skin beneath her ear, his teeth grazing gently before his tongue traced a slow, wet path down her neck. The contrast between his rough stubble and the slick heat of his tongue sent shivers down her spine.
Jake’s fingers matched the rhythm of his mouth, pressing deeper inside her with each thrust while his thumb rubbed tight, relentless circles over her clit. The friction was almost unbearable, the sensations building to an unbearable crescendo.
Margot's hips rocked unconsciously against Jake's hand, her free hand gripping his jacket so tightly her knuckles shone white through the fabric. She felt so wanton, so brazen. She was being wild and it added to her excitement.
Jake's breath came in sharp, controlled bursts against her ear, his other hand finally abandoning its teasing on her thigh to grip her hip, holding her steady as his fingers worked her with relentless precision. The jazz saxophone's sultry melody wrapped around them, the slow, sensual notes syncing perfectly with the rhythm of his touch.
"Jake..." Margot's voice was a whisper, a plea, a promise.
She arched her back further, her body a bowstring pulled taut between pleasure and surrender. The emerald pendant dipped low between her breasts, the cool stone brushing against her cleavage as her chest heaved with every ragged breath. Her nipples stood out like eraser tips poking through the think fabric of her dress.
Jake's fingers worked inside her with a slow, deep precision, each thrust drawing a soft whimper from her lips that she tried to swallow back into the sultry jazz humming through the bar's hidden speakers. His thumb circled her clit with infuriating slowness, the pressure building like slow liquid heat through her veins. Margot’s breath hitched when Jake’s fingers curled inside her, pressing against that sensitive spot that made her toes curl inside her spiked heels.
“Fuck, you’re tight,” Jake murmured against her ear, his breath hot and ragged. His free hand slid up to grip the side of her neck, not squeezing hard—just enough to ground her in the moment, enough to remind her who was in control right now. The pressure sent a fresh wave of arousal pooling between her thighs, slicking his fingers as they worked her with relentless precision.
The jazz saxophone’s sultry notes wrapped around them like silk, the melody syncing perfectly with the rhythm of Jake’s touch.
Margot’s hips lifted slightly off the barstool, her body arching against the high back as Jake’s fingers worked her with agonizing precision. His thumb pressed firmly against her clit, circling with slow, deliberate strokes and his forefinger pushed against her g spot causing her to squirm on the stool almost fucking his hand. The fabric of her dress rode up higher, baring more of her thighs to the cool air of the speakeasy. “You’re so responsive,” he murmured, his voice rough with satisfaction.
Jake’s fingers curled inside her while his thumb pressed harder against her clit, the rhythm steady and unrelenting. Margot felt herself come undone feeling her orgasm rip through her body.
She could feel herself squeezing his fingers as she came, clamping down on him as her hips rose off the stool involuntairly. She bit her lip to stop herself from making a sound as she came.
Jake’s mouth was at her ear whispering as she came down from the high, “Good girl, let it out.”
The music played on around them, the world keeping its steady pace even as Margot’s world had tilted. She collapsed back against the stool, her body loose and spent, the emerald pendant glinting weakly between her breasts.
Jake slowly withdrew his fingers, showing them to her. They glistened in the dim light. He brought them to his mouth, his tongue cleaning each digit with deliberate slowness. Margot watched him, her chest heaving, her lips parted.
The bartender walked over and put a fresh whiskey glass in front of her. "It's on the house." he said with a wink. "You look like you need it." Margot took a sip, letting the whiskey warm her throat and ease the last aftershocks of pleasure. Jake stepped back, taking her in with hooded eyes. She watched as he adjusted himself subtly, the bulge in his trousers impossible to miss. Margot raised an eyebrow at him. "We should probably go before I decide to christen this bar stool." Jake chuckled darkly, his fingers flexing at his sides as if he were physically restraining himself from reaching for her again.
"I think you already did." he laughed. "But we should definitely go before I lose control.
Again."
Jake exhaled sharply, the sound somewhere between a laugh and a groan. His fingers flexed at his sides, knuckles whitening, as if he were physically restraining himself from reaching for her again. The shadow of his stubble darkened his jawline, the faint pulse in his throat betraying the effort it cost him to hold back.
Margot tilted her head, her lips curling into a slow, knowing smile. The emerald pendant swayed between her breasts with the movement, catching the dim light like a secret. "Afraid of what might happen if you don’t?"
Jake didn’t answer right away.
Instead, he reached for Margot’s hand, his fingers curling around hers with a possessiveness that sent a fresh pulse of heat through her. His palm was warm against hers, calloused in places that suggested he worked with his hands—maybe not at a desk, maybe not in an office like hers. She let him guide her from the barstool, the high leather cushion brushing against the backs of her thighs as she stood.
The speakeasy seemed to tilt slightly as she rose, the floor solid beneath her heels but the atmosphere charged, electric. Jake’s grip tightened just enough to remind her who was leading now, but not enough to hurt.
Margot let him guide her through the crowd, the warmth of his palm seeping into hers, the rhythmic press of his thumb against the inside of her wrist sending shivers up her arm.
Along the way, she noticed a number of people in the crowd staring at her. The guys closest to them at the bar were staring at her in obvious lust. A couple across the bar were smiling at her knowingly. She also caught several disapproving looks from other nearby women. They must have made a bit of a spectacle, and Margot was a little embarrassed, but Jake guided her calmly and proudly through the crowd.
His presence seemed to ward off any pushback, and Margot relaxed into the warmth of his hand as they exited the speakeasy and stepped into the crisp night air.
Jake gave his ticket to the valet and his car arrived quickly. It was a sleek black convertible sports car with the top down. Jake opened her door and helped her inside, her skirt sliding dangerously high exposing her upper thighs.
Margot bit her lip and settled into the buttery leather seat as Jake walked around the front of the car. The engine growled to life with a rich, throaty purr.
As they pulled away from the curb, Margot watched the Boston skyline in the side mirror blur into soft streaks of gold and neon. The windows were down letting in the cool night air that tousled her hair and chilled her skin.
Jake's hand found her knee again, his touch possessive and warm through the thin fabric of her dress. Margot didn't move away. Instead, she parted her thighs slightly, giving him better access. Jake's fingers traced slow circles higher, his thumb brushing against the damp fabric that covered her sex.
His touch was confident, knowing—like he had already memorized the shape of her arousal.
Margot let her head fall back against the seat, the leather cool against her overheated skin. The convertible’s wind rushed over them, carrying with it the distant hum of the city—car horns, laughter, the rhythmic thrum of a bass line from a club down the block.
Jake’s voice was rough when he spoke, barely rising above the wind and engine. “So, at the risk of ruining things, I have to know. I've been chasing after you for months. What made you decide to meet me tonight?”
Jake’s thumb hovered just shy of her center—just enough to tease, just enough to make her thighs tremble. The question hung between them like the hum of the engine, vibrating through the air that separated them.
Margot turned her head toward him, her lips parted slightly, the taste of bourbon still lingering on her tongue. She watched as the city lights blurred past them, neon reflecting in the dark pools of his eyes. “To be honest, it was something I recently learned about my husband.”
Jake glanced over at her. "If he cheated on you, he's a fool."
Margot laughed. "No, nothing like that. It's more like he wants me to be with other men." Margot's laugh was a little breathless, a little disbelieving even to her own ears.
Jake chuckled. "Oh, he's a cuckold. I understand."
Margot was surprised Jake even knew what a cuckold was.
She looked at him in surprise. "You know about that lifestyle?"
Jake smirked as he navigated the car through the Boston traffic. "I know about a lot of things, Margot. I know that some men get off on watching their wives with other men. I know some women like being watched. I know that sometimes the best sex comes from the most unexpected places. I've actually had a relationship with a cuckold couple before."
Margot felt a shiver run down her spine at his words. "You have? What happened?"
"It went on for a year, and everyone was happy with the situation." Jake replied. "But they moved away to another city, so I don't see them anymore. We're all still friends though."
Margot puzzled over his answer. She had been so afraid of this ruining her marriage, but Jake's description made it sound like everything was just fun. "So, what was it like?" She asked.
Margot’s voice quiet, her thighs still tingling from his touch earlier.
Jake’s grip on the steering wheel tightened for just a second before he relaxed into the movement of the car weaving through the city. The convertible’s top was down, the night air cool against her skin, still carrying the ghost of his fingers between her legs.
He exhaled through his nose, a slow breath out, before answering. “It was fun, like play.” he said finally. "There are many different kinds of cuckold relationships. Some just want to watch, some want to join in for threesomes, sometimes the husband gets off on humiliation and abuse."
"What was it like for you three?" Margot asked with a tremor in her voice.
“The husband, Mark, he was...submissive to her. He would watch, touch himself. She would taunt him and tease him. Sometimes she would make him do things." Jake said tentatively.
His fingers flexed on the steering wheel, knuckles whitening briefly before loosening again. Margot watched the way his jaw tightened at the memory, the faint shadow of stubble catching the passing streetlights like punctuation marks in the dark.
The convertible hummed along Storrow Drive, the river glinting to their left under the moon, a silver ribbon cutting through the city. Margot turned her head slightly, studying Jake’s profile—the strong line of his nose, the slight dent in his chin where a scar might hide beneath the stubble, the way his Adam’s apple bobbed when he swallowed.
"How did that make you feel?" Margot asked.
She wanted to know what was going on in his mind. "Having a submissive husband is such a turn on."
Jake's grip loosened on the steering wheel as he heard her say that. The leather creaked slightly under his palms. He exhaled through his nose, his chest rising and falling with deliberate control.
"It was...intense," he admitted finally, his voice rough. "Not for everyone, but for them, it worked. Mark needed to be reminded who was in charge, and she liked reminding him. He got off on being used, on being hers to command while she took what she wanted from me."
Margot shivered at the raw honesty in his voice.
"We would have wild and crazy sex with him being degraded and abused. Then afterwards, we would all hang out laughing together over a few drinks and some weed. Everyone got what they wanted." Jake said, looking over at her.
He had to force himself to keep his eyes on the road and not just stare at Margot's exposed thigh where her dress rode up. The engine purred in the quiet night.
“That sounds...so much better than I expected.” Margot murmured, her voice having a slightly dreamy quality to it. The conversation about Jake's past experience with cuckolds gave her a sense of relief. She shifted slightly in her seat, the cool leather of the convertible seat brushing against her bare skin. "I've been very nervous about this whole thing. Derek has all these submissive fantasies. I think he needs me to be cruel to him, but I'm concerned about how it will affect our marriage. I also worried that other guys might find the situation a big turn off." She admitted, looking over at Jake for a response.
The trees along Storrow Drive blurred together into soft lines of green and gold under the streetlights, their branches forming a natural canopy over the road. The convertible hummed along beneath them, the engine purring like a satisfied cat. The cool night air rushed past Margot’s arms and neck, making the fine hairs on her skin rise.
Jake exhaled through his nose, his fingers tapping once against the steering wheel like he was thinking. The leather seat creaked slightly under his shifting weight. He glanced over at Margot, the dashboard lights casting sharp shadows across his face. "I think you’re overthinking it," he said, his voice low and certain.
"Most guys wouldn’t think twice. They wouldn’t care if Derek’s into it, as long as they’re the ones getting to play with you." His fingers drummed again—once, twice—on the wheel. "The only thing that matters is how you feel."
Margot exhaled, slow and deliberate, watching the city lights blur into streaks outside the window. The convertible’s engine growled softly beneath them, a steady rhythm that matched the calm spreading through her veins.
"You're right," she admitted quietly. "And how do you feel about all this?" she asked.
Her voice was husky with curiosity, with something that bordered on the desperate edge of innocence, despite the evening’s events. Her fingers traced idle patterns on the car’s leather seat, the emerald pendant swaying between her breasts with each breath she took.
Jake’s eyes flicked toward her for a brief second, the dashboard lights bleeding across his face like liquid gold. His jaw tightened, the faint shadow of stubble catching the pale glow. “Honestly?” he said, voice rough with restraint. “I feel like I just hit the goddamn lottery.”
The words hung in the air between them, thick with implication.
Margot swallowed hard, watching Jake’s strong hands grip the steering wheel, knuckles flexing as they navigated the quiet Boston streets. She could feel the heat of him radiating through the console, the faintest scent of his cologne—warm amber and sandalwood—wrapping around her senses.
Jake exhaled sharply. “I’m not the type to play games, Margot. If I wanted to sleep with someone, I’d just ask. If I didn’t want to, I’d say so. But you? You’re different.” He cast a sidelong glance at her. “You’re reckless. You’re smart.
You’re bold. And I know you’re curious. So am I.” He paused. “But I’m also a gentleman.”
Margot smirked. “Aren’t you the same man who just fingered me to climax in a bar full of strangers?”
Jake let out a low, dark chuckle. “Damn right I am. I’m a gentleman with a healthy appetite. And right now, that appetite is very, *very* single-minded.”
The car purred onto up a quiet, tree-lined suburb where the houses slept behind hedges and lamplight and pulled into Jake's driveway. He lived literally 4 blocks from Derek and Margot's house.
Margot sat up straighter, the leather seat whispering against her bare thighs; the evening air still hummed in her veins and between her legs, a damp reminder of Jake’s touch. The convertible rolled to a stop, its chrome bumper catching the dull glow of the porch light. A single bulb over the garage door flickered once, then steadied.
Margot exhaled through her nose, watching her exhale fog the cool night air.
“You okay?” Jake asked quietly.
"More than ok." she replied, flashing him a smile. "Let's go inside."