Another First Date Ch. 02

Story Info
Things warm up as they have their first "official" date.
4.1k words
4.67
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Part 2 of the 2 part series

Updated 06/10/2023
Created 06/06/2021
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As promised, things heat up in this chapter. Thank you so much for reading through my first story. It's nerve wracking to take the plunge with publishing on here!

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The week passed uneventfully for Cassandra. Work was fortunately slow as she found herself distracted by texting Javier in the spare time. They talked about everything from where they grew up, to local restaurant recommendations, and favorite movies. The safest of topics.

They made plans to get dinner again on Friday and she was looking forward to it. After all their talking, and the sexual tension of that first kiss, Cassandra found herself trepidatiously excited to see him again.

As Friday finally arrived, Cassandra stood in front of the closet that morning, debating what to wear. She planned to meet him right after work. That meant a balancing act of tasteful yet attractive. Lingerie was the easy choice: simple black lace set. Classy and timeless.

Admiring the contrast of black against creamy ivory flesh, she ran a lacquered red nail along her hip, tracing the fabric edge of the black lace panties. The intensity of the kiss was still fresh enough to stir a heat in her body. Glancing at her watch, she made a last minute decision to ditch coffee and make time for morning masturbation.

Cassandra turned from the mirror to her bed and climbed on top, getting on all fours. She licked her middle finger and reached back between her legs, pushing aside the fabric of the thong. There was a glint of moisture already sparked from thoughts of the kiss. She gently rubbed the pad of her finger over that sensitive nub of flesh, alternating between caressing over the clitoral hood and under to the almost too-fragile clitoris.

Her opening contracted and flexed with the stimulation of the clit. Not leaving it unattended, Cassandra dipped back further, slipping a single finger inside for a few strokes before returning to her clit.

She fantasized not only of the kiss the other night, but if it had gone farther. If she hadn't stopped him. If he took her right there in the hallway against the wall. If they moved from the wall to the couch. If he had bent her over the sofa and fucked her with her skirt pulled up to her hips, panties torn away.

Cassandra's motions became more frantic with the thoughts and she moaned into a pillow, face buried. She imagined him taking her in this exact position: on her hands and knees, ass arched into the air. The thought of him roughly pounding into her was too much as an orgasm took her by surprise. Usually, she could feel one building up, but this took her breath away as she spasmed. Cassandra's body shook as she continued to fervently attack her clit for a solid twenty seconds after, thoroughly milking the orgasm out of her. No drop of ecstasy was left behind. The sensation finally turned to painfully sensitive and she let up.

With a peek at her watch, she bounded off the bed, pulling panties up as went. Cassandra ran to the bathroom with a sense of urgency to wash her hands. Just as quickly, she darted back to the bedroom to finish dressing. She was now on a time crunch after her little detour.

The first time Javier had seen her, Cassandra was wearing a casual dress and she wanted to impress him with something a bit more provocative. Finally, she settled on a grey pencil skirt that hugged the swell of her hips and ripe ass, with a black button-up flowy blouse. She made a mental note to undo the top two buttons to flash a hint of cleavage to spice things up after work. A simple black blazer and pumps completed the outfit.

Cassandra reached into the dresser and grabbed a black lace thong as a back-up fresh pair, should the evening head in a more sensual direction.

Heading out the door, she felt a thrill in her chest, excited for what the night might bring.

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Cassandra arrived a few minutes early to the restaurant and made her way to the bar for a little liquid courage. It was warm enough that she ditched the blazer, draping it on the bartop. Even in heels, she was short enough that as she leaned against the bar top, breasts pressed together and strained against the fabric. She flashed a sliver of exposed flesh and cleavage towards the bartender, catching his attention.

"Hey there, can I get a gin martini on the rocks? Olive, please?" Cassandra ordered.

The bartender gave a quick nod of his head. An unfamiliar voice spoke beside her, "I don't know if I've ever witnessed a woman order gin."

Cassandra tilted her raven head, bright blue eyes flashing on the older well-dressed man to her left, "Is that a compliment?" Her voice held a coy yet challenging tone.

"It's just unusual. Most younger women order something fruitier like a lemon drop martini or a cosmopolitan," the stranger replied, a little too obvious as he gave her a once over.

"Then perhaps you spend too much time around girls rather than women," Cassandra responded, not usually this quick witted, but in rare form.

"Touché. Is that an invitation?" The stranger smirked, steely blue eyes twinkling with mischief.

Cassandra shook her head, wondering where the bartender was with her drink. She was careful with her body language, only turning her head and not full body towards the businessman, "No, no thank you."

"You aren't drinking alone, are you?" The stranger asked, undeterred.

A hand touched her shoulder and she jumped, startling.

"I'm a minute late and you're already making a new friend?" Javier spoke from her right, relief washing over her.

Cassandra's eyes were a little wide when she turned to Javier, hugging him instinctively, whispering into his ear as he leaned down to clasp her, "Thanks for saving me."

"I highly doubt you need saving. You look like you can handle your own." A touch of mirth in that smile, dimples twinkled as perfect white teeth peeked out.

Cassandra left a hand on his bicep as she spoke, "Oh, I can, but this is far more preferable."

Javier took in her features, commenting, "You look great. Very different from last time... but different is good."

"Don't worry, you clean up well too," she quipped, smoothing her hand over the fabric of his shirt. He had dressed up for the date, a departure from that first meeting in basketball shorts. "Your belt even matches your shoes."

"Thanks, I like this belt. Quite a bit actually. Do those sorts of things matter to you?"

Cassandra paused, considering the question, "It's less about what you are wearing, but the intentionality behind it. It means you're detail oriented."

"Are you always analyzing things?" Javier raised an eyebrow.

"It's hard to turn my brain off," she said with a shrug, breaking eye contact.

Javier leaned down, speaking softly into her ear, "I'm sure there are ways to distract that mind of yours." The deeper tone, usually reserved by men for darker inclinations, caused something deep inside of her to tighten. A healthy flush rose up her cheeks as her date turned to place his order with the bartender.

Javier's magnetic brown eyes turned back to Cassandra. She held his gaze, letting the unadulterated chemistry hang thick between them.

He broke the silence first, "How was work today?" Cassandra shared her day as they moved from the bar to table, catching up on their week over dinner, despite having been in touch.

It was the spring blossom of a relationship, when there is still so much unknown between two individuals, other than an undeniable sexual attraction. Dinner naturally progressed to a slow walk to her car. The conversation seamlessly continued while bodies drew close, hips brushing.

"This was an enjoyable evening, even if I found you already moving on to older pastures," he gently ribbed, that boyish smile lighting up his features.

Cassandra groaned, rolling her eyes, "This is me." They drew up to her car as she added playfully, "I can't help it if I'm a corporate bigwig magnet."

"Oh really, is that the case? You telling me you have a waitlist going on at work?" He teased, sliding an arm around her waist as he drew her in close.

"Now you're just putting words in my mouth," she quipped defiantly.

Javier wasted no time, murmuring as he leaned in for a kiss, "I can think of other things to put in that pretty little mouth." He kissed her thoroughly and deeply; her body responded in proper form, melting into his grasp. Bringing his massive hand up to cup the nape of her neck, his fingers accidentally caught in her dark hair.

"Oh, no, I'm so sorry," she blurted, pulling her mouth away. Javier didn't let up on his grasp on her, but merely untwined his hand from her raven locks.

Faces inches apart, Javier's eyes held something dark, although he smiled, "Why do I have a feeling you like having your hair pulled?"

Cassandra laughed nervously out of instant reflex, at loss of words. She managed another apology, not acknowledging the words. "I'm so sorry again."

Testing the waters, his fingers cautiously pulled a handful of her hair at the nape of her neck. He watched her face for a reaction, "I'm not wrong, am I?"

Cassandra didn't doubt he knew exactly what he was doing as an involuntary gasp escaped her throat. It was all the prompting Javier needed. He went in for another kiss, pinning her body against the car. Grinding his hips into her, she could feel him firm through his pants. The sensation elicited another soft sound from her.

She drank from his lips like there was no other moisture left in the world as he continued to grip her firmly by her long black locks. Bodies pressed tight, Cassandra reciprocated the motion of his hips with her own, an active recipient.

Voices broke their concentration as a group approached, looking for their car. "Maybe we should go somewhere more private," she suggested while he eased his body off of her.

"Yours or mine?"

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They pulled up into her parking lot at the same time. Butterflies danced in her stomach as he met her at the car door, chivalrously helping her exit the vehicle. It had been both a short and incredibly long drive full of anticipation. Distracted, she forgot her blazer in the car.

"Nice not having to fight for parking at the coffee shop," he joked while they made their way to the apartment door.

"Having parking is worth its weight in gold in this city," Cassandra agreed, unlocking her front door. She beckoned him in with a gesture, glancing back over her shoulder.

Javier waited at the doorway, propped on one elbow against the door frame. His gaze was unwavering as he spoke, "I would never make untoward advances, but if you invite me in, I plan on fucking your brains out."

Bright blue eyes froze in surprise. "I... " she stammered, "Yes, please."

"That's what I wanted to hear," he spoke as he bridged the distance with two strides, door slamming shut behind him. Javier scooped Cassandra into his arms and planted a kiss not on her lips, but on the edge of her jaw, and then down her neck. The sensitive flesh of her throat was almost too much to bear for Cassandra as she sharply moaned, fingers digging into his back.

His large hands roamed over her curves, sliding down and over full hips, grabbing handfuls of her ass. Cassandra went on tiptoes in her heels, lifting with his touch, to meet his body. She let him take the lead and turned her body over to the uncontrollable intensity of his desire.

Javier brought his lips back to hers and began walking them back towards the darkened bedroom, not allowing the kiss to break.

He sat down on the bed, nearly equal height to her petite stature. They watched each other's faces as he ran his hands over Cassandra's exaggerated hourglass curves. Still a little nervous, attraction won over trepidation as she reached out to unbutton his shirt. Javier groaned softly at the sight of her creamy mounds pressed against black lace.

"Do you mind if I turn a light on?" Cassandra asked. "I.. I like being able to see what I'm doing."

"Of course," he replied, not wasting time in shedding both his shirt, undershirt and shoes in the time it took Cassandra to make her way across the room for a table lamp on her dresser. It had a lower wattage bulb that gave off enough light without the interrogation effect of an overhead.

She turned back to find him standing in socks, unbuckling his belt. Surprise washed over her face at the unexpected sight of endless amounts of tattoos across his bronze torso, shoulders, and biceps. It caught her off guard. Recovering herself, Cassandra walked to him and placed small palms on his chest, tracing nails over his pecs.

Javier had stopped undressing to watch her reaction. He smirked, "I was a bit of a knucklehead as a kid and wear the memories of it."

"You'll have to tell me stories one day," she responded, going back on heeled tiptoe to kiss him deeply again. His hands were quick to unclasp her bra as they kissed, slipping the straps off her shoulders. Cassandra let the bra fall to the floor, leaning into him. His hands came up to cup and knead the soft flesh of her breasts.

Feeling bold, Cassandra finished what Javier had started with his pants, unzipping them and tugging gently. She broke the kiss and slowly dropped to her knees as she pulled his pants down with her.

Topless and clad only in pencil skirt and heels, Cassandra rubbed her face against the material of the boxer briefs that held Javier's manhood back from her. She licked a long line of flesh along the edge of the waistband, peeking up to catch a glimpse of his expression. Javier's countenance was heavy with need as he watched her, a sight to behold on her knees.

Returning to the task at hand, Cassandra gently ran the tips of her nails along the waist band before slowly edging it down, hitting resistance with his firm cock. She kissed his flesh as she went, finally pulling the fabric over his manhood, delighted as it sprung free. His uncircumcised cock was slightly above average and straight as an arrow. He was completely hard as she laid a kiss along the head, drawing a small groan from above. She gripped the base of his shaft with her nondominant hand, slightly pulling back on his foreskin as she did so.

Cassandra took the exposed sensitive flesh of his head in her mouth, flicking her tongue over and around. Continuing her descent, she took him in her mouth inch by inch, tongue and saliva moistening the path forward. She finally stopped as lips met her fingers firmly holding him in place. It wasn't until then that she withdrew and began working his cock with her mouth.

Moans of her own reverberated along his cock as she threw herself into the act, enjoying the control over his body. Cassandra introduced a second hand along his slippery shaft, using a corkscrew motion in tandem with her mouth.

Javier broke her rhythm with hands on her shoulders. "This is incredible. I promise I'll come all over those glorious tits another day, but right now, I want you on that bed." A tingle shot through her body with his words. He offered a hand up and Cassandra accepted, while she wiped at her mouth with the other.

Back on her feet, Javier grasped her hands as he commanded, "Step out of those." She did as he requested, kicking off high heels and dropping a few inches in height. His assertive nature caused things low inside to pull tight.

He leaned down and whispered in her ear, "Do you want this?"

"Yes, please," she answered without hesitation, the sensation of his lips close to her ears sending shivers through her body.

He growled, "Fuck, I love it when you say that."

He kissed her deeply again, pushing her back on the bed as he did so. Javier buried her shorter frame under his, continuing to probe her mouth with his as hands came to her skirt and began peeling it down. He didn't waste with leaving the panties on, pulling both layers off in the same go. His lips travelled down her body to her breasts as he continued working the skirt down those creamy thighs.

A pert nipple was completely engulfed by his mouth and Cassandra sharply moaned in turn. Pleasure rippled through her body as he suckled on her nipple, hands massaging her calves as he had her completely unwrapped.

Javier's lips kept traveling south, over the soft flesh of her stomach and to the closely trimmed hair of her sex. It was shorn so close to the skin, that it was almost smooth to the naked eye. As he laid kisses, he began to touch her most intimate of parts, testing the waters. Cassandra took in ragged breaths, gasping at the simultaneous sensations.

Javier grew harder as he felt how wet she was, a single finger gliding over her clit to her opening. He slowly dipped his finger into her, surprised by how taut she was. Cassandra was moaning at this point, penetration her achille's heel. Turned on from all of the foreplay, she knew she would have her first climax in no time.

Encouraged, Javier withdrew his finger and glided his tongue over her satin lips. While she left the barest of hair on top, beneath was absolutely smooth.

Cassandra rose up on her elbows, blue eyes peering down with need in her eyes and voice, "Please, I... I want to feel you inside of me." Javier's cock twitched with her words. He took one long swipe of his thick tongue along her exposed sex, drawing a cry from her. She tasted like water with a hint of lime, light and slightly acidic.

Complying with her wishes, Javier made his way back up her body, laying kisses as he went until he reached her mouth. They kissed as he reached one handed for his pants. Fishing out a condom, he broke away to slide it on.

Javier lowered himself back over her body again, watching her reaction as he rubbed his cock against her wetness. Cassandra held her breath with anticipation, falling into the deep brown of his eyes.

She felt him tease at her opening, thick and hard against her slit. Slowly, he parted her open, stretching her small hole to take all of his head. A brief ripple of discomfort, bordering on pain, flashed across her face. She closed her eyes in concentration. It had been too long since she had been with anyone and her body involuntarily protested against the invasion. Undeterred, Javier continued to bury himself, stopping as he was just nearly able to fit all himself inside before hitting resistance.

Cassandra let out a breath she didn't know she was holding and opened her eyes. Her sex relaxed slightly as it grew accustomed. Javier slowly pulled out a few inches and back in; a moan from Cassandra greeting him. Pleasure replaced the fleeting pain. Javier began to work himself in and out slowly, methodically.

Between the lead up after the restaurant and their foreplay in the bedroom, she found an orgasm building fast and quick. "Fuck, I think I'm going to come already," she whispered, warning him.

Javier went up on to his arms and put all of himself into her, bottoming out. The feeling of him hitting her deepest parts was all it took to send her over the edge, moans pouring out of her. Cassandra gripped his shoulders tightly, buckling her hips against his. She tilted her dark head back, blue eyes rolled back in turn, arching her body off the bed.

Javier slipped a hand under the hollow of her back as he began to thoroughly fuck her, giving in to the way he truely wanted her. He drove the length of himself into her over and over at a steady pace, "You feel amazing, Cassandra. God you feel so good."

"I want all of you inside me, all of me," she cried out, not quite aware of the words that came tumbling out of her mouth during the throes of ecstasy.

He leaned his head down low, roughly whispering into her ear, "I'm going use all of you tonight."

His words drove her over the edge again with a scream, her vaginal muscles sharply constricting, "Yes, please, Javier... please."

"Please, what?" he teased, pinning her hands back over her head as he roughly drove his cock into her. Still climaxing, she couldn't respond, completely overwhelmed. He thrusted until he knew the moment had passed, her body no longer buckling.

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