It was Friday evening, and Cassandra sat in her makeup chair, fresh out of the shower. She dried her hair with a towel and thought about her outfit for the night. Getting ready for dates had become a chore. It was something that no longer excited her. After her divorce, she looked forward to child-free weekends and potential romantic trysts. Back then, she was full of hope and optimism. But now, she felt disillusioned. Nonetheless, she plugged away in search of a meaningful connection. Whatever that meant, she wasn't sure anymore.

Mirrors surrounded her. To her right, three large panels of closet doors cast back a reflection. Middle-aged; she didn't want to recognize that woman. Her bathroom lighting was terrible. It was too bright; she saw every flaw. Like the new wrinkle that appeared along her mouth. Where the hell did that come from? Disappointed, she stood up and walked pointedly toward the closet. Enough with the self-pity already, she needed to turn the night around.

After confining her breasts to her chest, with the cleanest bra she could find, she decided on a dress. The low-cut black one would do. She wiggled her hips and wrestled it down the length of her body. Finally, in place, the dress rested mid-thigh. She bent over to check herself in the mirror and poked out her butt. Should she wear underwear? A slight peek at her freshly shaved pussy confirmed, she probably should wear a thong.

Cassandra walked over to her dresser and dug through the tangled mess. There were many colors and sizes to choose from. She had a specific one in mind. She searched for a few seconds; getting frustrated, but finally found it. It was one of her favorites. The material was minimal, essentially a red silk string. The cool fabric felt smooth and luxurious against her clean soft lips. It sat sweetly between her butt cheeks. She felt sexy in it. Her pussy pulsed; she felt horny for the night.

She was excited. Clint seemed different than the others. He wasn’t a financial advisor or accountant. He was a car mechanic. He owned his shop. She didn't know much about him, but he was complimentary and polite. He was a divorced dad of two adult children and said he’d been casually dating for a few years. He mentioned he was looking for a connection with someone “Special,” and she cringed at that. He was tall though, so she was willing to give him a chance.

She put on the four-inch strappy heels, that showed off her thin, muscular legs and poured a glass of wine. She glanced at the clock. It was almost seven; she was running behind.

***

Cassandra arrived at the bar five minutes late. It was 7:35. She wasn’t nervous. After several months of dating, her expectations had dropped tremendously. She was happy for her date to resemble their pictures. If the conversation went okay, and they offered to pay, it was a win for her. When she thought about it, her hopes were raised for guys who waved red flags like clowns at a circus. How embarrassing! she thought, and resolved to keep a level head.

“Here,” she texted Clint.

“Great! I’m at the bar. You can’t miss me,” he replied.

Cassandra got out of her car, pulled down her dress, and fixed her hair. She was a little surprised that this was what Clint chose. He didn’t seem like the upscale type. She thought, perhaps, he was trying to impress her.

Her dress inched up with each step. The viscose fabric blend shrunk in the dryer, and she had to pull it back down every third or fourth stride.

The doorman stared at her. “Good evening, Miss!”

“Thank you, Sir!” she said and walked directly inside.

The maître d’ stood in front of her and said, “Good evening, Madam.”

Her eyes searched for the bar. “Good evening. I’m meeting someone at the bar.”

She took a few steps past the partition and spotted the bar towards the back of the building. She liked the look of the place. She thought she knew all the best spots, but had never heard of this restaurant before. She was surprised, it wasn’t far from her house. How could she have missed it? She was intrigued. Clint may have a few tricks up his sleeve.

As she continued toward the bar, people spoke in hushed tones. She kept her eyes forward and looked for Clint. She wanted to avoid the awkwardness of not spotting him, that was the worst. But then, she caught sight of him, at the back of the bar.

He spotted her too, and was eager. Put his drink down, and stood to greet her.

He was tall. Taller than she had imagined. She misjudged what 6'4 looked like. He still had a few inches on her in heels. His broad shoulders hunched forward a bit, apparently a consequence of his height. Her eyes beamed. He was handsome in real life.

“Wow! Smoking hot!” he said, “My O’ My, Cassandra, it is a pleasure to meet you!” and he hugged her.

"Thanks, Clint," she said coyly and blushed. “You aren’t too bad yourself.”

Her nerves were kicking up. She sat down and looked for a place to put her purse.

“What would you like to drink?” he asked.

“I’ll do a double vodka, house is fine, neat please.”

“Sure, no problem.” He lifted a finger to get the bartender’s attention.

Cassandra adjusted herself and settled into her seat. She made a point to pull down her dress several times and caught him as he stared at her breasts, then quickly shifted his gaze.

She took the opportunity to check him out. Clint was attractive, conventionally so. He had a lovely full head of hair and silvery gray highlights. He was sexy. She wondered what it would be like to hold a handful of his hair while he pumped her pussy full of cum.

She caught herself. Such a horny little slut, she thought. What hadn’t she masturbated before the date?  Now, she couldn’t concentrate.

The lack of regular sex since her divorce had been frustrating. They led a healthy, albeit boring, sex life. Steamy encounters with strangers were what she fantasized about now. The possibilities felt endless. Unfortunately, post-divorce sex hadn’t been all that it was cracked up to be. There were too many selfish and unskilled lovers out there. Where were all the top-notch gentlemen? she wondered. Focus! she told herself and returned her attention to him.

“What’s up?” He wondered what she was thinking.

“Oh, nothing.” She was afraid her face had given her away.

The bartender sat down her drink and she caught his eye. He was much younger, very fit, and very handsome. He might have been an aspiring model.

He shot her a bright white grin.

Clint shifted in his chair, "Thanks, mate.”

The sexy bartender disappeared.

“Handsome guy,” Clint said, and looked at her, meeting her eye.

“Yeah, he’s cute. So young though!” Cassandra said and took a big gulp of her drink. It burned the back of her throat. There was no chaser. She’d forgotten to order one, and the hot bartender hadn’t poured her water yet. She coughed. “Sorry,” she said and tried to play it cool.

Clint laughed, and watched her chest; her breasts jiggled. He enjoyed them as they bounced. “You’re cute,” he declared and nodded at them in recognition.

She coughed and looked down. Her gaze veered toward his hand, it rested on his thigh. It was giant and matched his 6’4 frame. She thought for a moment how sexy he was. He was different than the others. They were boring, self-important, and selfish. Clint was mysterious, and rough around the edges. She would fall for that any day.

Cassandra wondered if he would give her a full maintenance check. His fingers caught her eye. They were thick, rigid, and noticeably dry.  His nails were trimmed. She couldn’t help but notice the black stains that ran along the edges of his nail beds. The neatly primed lines of oil juxtaposed against his thick, scaley skin, made her pussy wet. She imagined him thrusting one of those greasy fingers inside her, and what other tools might he have in his shop?

Cassandra snapped back to reality. "Thank you.” She felt uneasy at her dirty thoughts. She shifted and pointed her legs toward him.

He looked down and noticed her dress had risen another inch.

“My pleasure,” he said, and met her stare. His fiery blue eyes surveyed her body with expectant desire as he peered down the length of her legs, unashamed.

Cassandra took another sip of her drink, fully aware that she was being evaluated.

“I like your heels.”

He attempted to lift her foot to inspect.

“What are you doing?” Cassandra said but didn’t resist.

“Let me see.”

“Okay fine.” She sighed and leaned back in her barstool.

“Did I tell you; I have a thing for girls with pretty feet?”

“No. Doesn’t every guy, though?”

She released the tension in her inner thigh and allowed him to do as he pleased.

He lifted her leg and laid it across his lap, and admired her toes. “Cute!” he said, “I like the color, and your legs are amazing!” and ran his dry scratchy fingers along her. He stopped to rest his hand on her thigh.

The bottom of her dress scrunched up around her butt. A man walked by. He looked at them and winked. Had he seen her pussy?

Clint looked at Cassandra, “Do you like this?”

She nodded. She was tipsy and had already finished her drink.

Clint caught the attention of the sexy bartender, who finished making a drink. He made his way over to them. “Another round?”

“Yes,” Clint said and leaned back in his chair. He pulled Cassandra’s leg open to give him a peak.

The bartender looked at them and laughed, “Okay then,” he said.

Cassandra was tipsy with desire. Clint caressed her inner thigh. His fingers were rough, there was no mistaking his touch. Each time he moved them further up. She was turned on as she felt a slight breeze between her thighs. The silk string thong was lodged deep in her fold. She longed for Clint to sweep his finger in and relieve the pressure of it from her slit. She shifted her weight in the seat. Clint brushed the back of his hand against the breadth of her vagina.

“Oh wow! You’re soaking wet," he whispered, thrilled at the discovery.

“I know. You’re turning me on.”

“Oh really?” he asked, “Well, we’ve only just begun.”

Without warning, he slid his forefinger past her thong and moved it deep inside her hole. His thick dry finger gave the perfect amount of friction, spreading her sloppy wet pussy lips open. Unable to control herself, she gasped, and let out a moan. The bartender and a few others poked their heads up. Clint pulled out his finger deliberately and slowly; it was soaking wet from her juices. He raised his hand and waved to acknowledge them.

She pulled her leg off his lap and straightened her dress, embarrassed. But damn, that felt amazing!

He admired her and put the glistening thick rugged finger to his nose, “You smell lovely Cassandra. What do you say we move to a booth?”

“That’s a great idea,” she said, “I’m hungry.”

***

They sat with their drinks but didn’t bother to look at the menu. Cassandra noticed Clint had requested a specific booth in the back, by the bar. It was large, circular, and dome-shaped; which provided a sense of privacy.

“You like oysters?” Clint asked her, “What about lobster?”

“Yes, and yes,” she said.

“Good,” he continued, “Now let me see those pretty feet again.”

She smirked and raised her foot to his lap, “If you must.”

He held her foot in its heel, staring at it in admiration. "Perfect toes," he said, "these heels are sexy." He lifted her foot to his nose and inhaled dramatically.

“What are you doing?” She asked she was shocked.

He looked at her as if he wanted to devour her.

The food runner appeared with their seafood tower and stared.

Cassandra took her foot back. She was tipsy and knew she needed to eat something before things got out of hand.

The food looked delicious. She selected a langoustine and a few oysters from the tower and carefully showered them with accouterments. She loved oysters but didn't think they needed any aphrodisiacs. They had plenty of chemistry after all.

"These are good! The best I've had in a while. Quite earthy, with a salty brine, don’t you think?” Clint asked.

“They’re great!” she said and slurped one down.

“I’m enjoying watching you eat them.”

Clint graciously offered the last oyster to Cassandra. Normally, she wouldn’t accept, but these were so good, she couldn’t resist. She placed the shellfish on her plate and noticed a round lump. She knew what it was straight away.

“Look Clint, a pearl!”

“Oh cool!” He picked it up to inspect.

Her attention was drawn once again, to his manly hands and then to his fingers that held the oyster shell. She felt a rush of desire.

He rubbed the pearl through the slime in a circular motion.

“Feels like a clit,” he said.

Cassandra laughed at him. “Let me feel.” She rubbed her finger on it. “Hmm. I don’t think so.”

“No?” he questioned. “Hmmm. Well, can I feel yours to compare?”

“You’re quite cheeky, aren’t you?”

“Sometimes.” He placed the oyster on the plate in front of him, “Come here.”

She hesitated for a moment and scooted closer.

He pulled her in so that she was right next time him. He lifted her knee, and laid it across his leg, and spread her legs open again. Her dress was twisted around her hips and her thong dug deep in her swampy pussy.

“Let me see what we have here.” He moved his hand down in between her legs.

She stiffened with anticipation. “Um, my thong is riding up inside me. Can you please pull it out?”

“Of course. My pleasure.”

She felt the scratchiness of his hands on her soft skin and remembered his oil-stained fingertips. Why wasn’t she grossed out? It turned her on. His fingers were big and knobby. She craved them inside her again.

His finger started at the top of her slit and moved down between her thong and skin. He used the massive digit to slowly lift the garment from inside her. Her pussy swelled as he released the tension.

“Is that better?”

She nodded. 

"Good,” he continued, “Now, about that clit. Let me feel that little pearl.”

Cassandra spread her legs wider for him.

He lifted the last bit of her dress, her lower half was completely naked, except for the red thong that lay against her leg.

He placed his lumpy index finger on her clit, and rubbed it in a circular motion. “You are wet. My finger slides so easily.”

“Well, what do you think? Does it?” She teased, eager for him to continue.

“Hmm not sure, let me inspect further.” He spread her lips with his first and third fingers and searched inside her. He pushed out her clit, and flicked it with his middle finger repeatedly.

She loved every bit of it.

The waiter approached the table. “Are we all done here? Can I offer you guys some, desert?” He noticed something was off.

Clint stopped banging her clit. "No, thank you. I think I have my dessert right here. Can we get another round of drinks though, please?” and focused his attention on Cassandra. "It doesn't feel exactly like a pearl but your clit is so smooth and pretty.”  His hand was soaked; and he smiled at her and then, shoved his middle finger deep into her pussy.

Cassandra’s body jolted, and she groaned with the forceful motion. His knobby finger felt so good inside of her. The ridges of it ran against her velvety lips. He held it there and allowed her to adjust to its size. She’d been pleased many times by just one finger, but he was so thick. She felt satisfied.

“Your pussy is so tight,” he said, “It feels warm and gushy in there. I could do this all night.”

She wiggled a little and clenched her vagina around his knobby finger, and hoped it encouraged him to continue.

"You would like that, wouldn't you? You want me to finger fuck you all night." He pushed and pulled his finger in and out of her. He was firm and steady and continued to build up the tension inside of her.

She thought she might have an orgasm right then and there.

The waiter came to the table with their drinks. “Sorry to interrupt, guys. Here you go.”

Clint pulled his finger out of her pussy and took a sip of his drink.

“How are you doing?” he asked her.

“I uh, I’m good.”

“What’s wrong?”

“Um…” she trailed, “I was just about to cum.”

He rimmed his glass of whiskey with his wet pussy finger, “Don’t worry, my dear, I’ll be sure to take care of that.”

She took a huge sip of her vodka and felt a little embarrassed. His filthy fingers felt like magic in her cunt, and she didn’t want him to stop.

***

Her pussy yearned for more as they finished their drinks, and Clint paid the tab. He followed her to the restroom. Her thong was out of place and felt uncomfortable wrapped around the side of her leg. She needed to readjust herself and decided it had been a poor choice for the evening. It got in the way more than anything. Next time, no panties, she thought.

Clint waited for her outside the ladies’ room. When she walked out, he pulled her into a room across the hall. There was no light on, only what shone through the large glass doors that faced the dining area. The doors were closed and had curtains pulled in front of them. The room was mostly empty, with two large tables pushed to the side. There were chairs stacked up against the wall next to them.

“What do you say? Ready for some more fun?” His eyes twinkled.

Cassandra was all in. He was so tall and masculine. His hair, his rough hands, she wanted every inch of him. “Uh… sure? Here?” she asked.

“Get up on that table, I’m ready for dessert!”

She couldn't resist his command. It was fun and light-hearted.

He walked her to the table, picked her up by the waist, and sat her down in front of him. He stood in between her legs and looked down as he cupped her face in his hands. She felt innocent. He was tender and sweet. “Do you like getting finger fucked?” he asked.

“Yes, I do. Especially by you.”

“Oh yeah? Why is that?”

“Well, uh, it’s weird to say, but I like your hands. They're so masculine!" she continued, "And your fingers have been turning me on all night. They are so thick and, don't take this the wrong way, but your knuckles are lumpy." She was drunk and rambling and said more than she normally would. “Something about the oil stains, it just seems you know what you’re doing. I bet you are a great mechanic.” She knew the last part didn't make sense.

“I wasn’t expecting you to say that.” He looked down to inspect his hands and turned them over. “So, you want my thick, dirty, fingers in your pretty little cunt?”

 “Yes,” she whispered, not sure how to answer his question.

He walked over lifted a chair from a stack and placed it in front of her. He took one of her feet, unfastened the strap to her heel, and let it fall to the ground. He placed the pad of her foot firmly against his nose and took a deep breath. He held it for a moment and exhaled with a giant grin.

“How long have you had a foot fetish?” she asked.

“All of my life. I used to smell my mother's shoes when she got home from work when I was a kid.”

“Oh my God! You’re kidding me?” She giggled at him.

He pulled up her dress and past her hips, which left her bare from the waist down, with only her thong. “Let’s take this off too. It is soaking wet,” he said and stripped it off. “Can I have it?” he asked and pushed it in is his pocket.

He sat there with Cassandra’s completely bare pussy at his chest. The noise had died down in the dining area. There were slight murmurs and clanks from the few guests that remained.

He rubbed his thumb against her soaked wet lips, and admired how thick they were.

She wiggled with anticipation as she felt the texture of his skin. He spread her lips with his forefinger and thumb and tried to get a better look at her hole. The light was dim, all he could see was a pink gushy mess. He let her lips close. He pointed his finger toward her and shoved it directly in.

“Ah!” she let out a small scream.

“Shh,” he said “I’m going to give you what you want. Relax and enjoy it, unless you want to get caught?” he teased her. “Don’t you want to see my filthy fingers defile you? Slut.”

Cassandra looked down. His large finger was jammed directly in her slit. Her pussy juices flowed freely around it. He continued moving his knobby finger in and out of her. The dryness of his finger was completely gone. It was soaked in her thick mucus-like lubrication. He slid it in, each knuckle rubbed her insides. He moved his finger and twisted it, it hit her G-spot. Had it been earlier, in the booth, she would have cum right then. But she was drunk, and an orgasm wouldn’t be that easy anymore.

She moaned as he increased his speed, and she pushed her hips back at him.

“Do you want my dirty fuck finger in your butt?” he asked.

That was unexpected, she thought and considered his question. “I think so,” she said and whimpered with delight.

“Turn over.”

He turned her over face down on the table and moved her legs to hang down on either side of him. Her ass was bare in the air, and she laughed at the thought of someone walking in on them. She didn’t mind giving people a show and that would be quite the sight, she imagined.

He lightly drummed on each butt cheeks.

“Hey!” She laughed at him.

With his index finger, he started at her clit. He drew his thick nubby finger slowly up her slit and collected the liquid from inside her. He scooped out what he could from her cunt, and rubbed the juice around her butthole. The sensation of his rough finger was new to that area. She shuttered, eager for more.

“Please!” she pleaded.

He placed the tip of his finger against the entrance of her squinched butt hole.

“Go easy on me though,” she said. She was a little scared and craved what was to come.

He pushed his distal phalange into her but stopped to gauge her reaction.

“Oh wow! Okay, let me settle in here,” she said and rocked on his digit a bit.

He tickled her in her anus and tried to expand it. Then pushed through the muscle and inserted his medial phalange with force.

“Oh! Shit that feels good!” she said.

He wiggled his finger back and forth, and then finally inserted the proximal phalange entirely inside her anal cavity.

She clenched her sphincter around his finger. Her pussy dripped.

He wiggled the finger out of her ass as she gripped it.

“You’re such a dirty little slut,” he whispered and dragged his crusty finger out of her rectum.

“I know,” she said and yearned for him to do it again.

He collected more of her pussy juice with his finger and caressed her clit.

She squirmed in delight. She could feel it. She was on the verge of a huge orgasm.

He teased her butthole some more. It opened and clenched with anticipation. He wasn’t gentle this time. He slammed his index finger deep into her ass, inserting all of it with one quick motion. He pushed it in fast and then fucked her rapidly. She felt the ridges of each lumpy knuckle’s force contract the muscle in her ass, over and over again.

Cassandra moaned, “Oh fuck, oh fuck,” she said. She felt helpless. Her pussy engorged. She craved another one of his raggedy fingers in her cunt.

Faster and faster, he fucked her ass and then, he slowed down for a minute. She felt a second finger search for her vaginal opening. He lined his two fingers up. One with her ass, and one with her pussy. He pushed them in and filled her holes up. She was overwhelmed with sensation. With his second stroke, her body clenched tightly. Her ass and pussy gripped him for dear life.

“I’m cumming!” she said, and her body quivered.

He jiggled his fingers and pulled them from her cavities. She slumped. A small stream of liquid shot from her cunt as his fingers exited her orifices. Did she just squirt? she wondered. Her entire body relaxed with the orgasm, and she lay there for a moment, taking it all in.

“I uh, I don’t know what to say,” she hesitated, “That felt so good. You lubed me up!”

***

They hadn’t realized how late it had gotten. The restaurant was about to close.

Cassandra noticed an odd look from the maître d’ on the way out. What had he heard? She realized she probably wouldn’t go back there again.

She was soaked between her thighs and heard a swish sound in her butt, as Clint walked her to her car.

“What?” Clint asked.

“Oh, it’s just that I, I feel bad.”

“Why?” He was concerned.

“Well, I got off. It was so hot! But you,” she wasn’t sure what to say, “didn’t get anything.”

“Ha! Don’t worry about that, Cassandra. I had a great time pleasing you.”  He dragged his soiled fingers across her face. “The scent of your luscious cunt, paired with the lingering fragrance from your anus, is plenty for me tonight.” He looked down at her, “Plus, my sexy red souvenir.” He pulled her thong out of his pocket and dangled it in front of her face. “Thanks for this.”

But, at that moment, she felt appreciative of him. It had been an amazing night. She wondered where things with Clint might go. At the very least, she’d found a sexy mechanic who could drain her fluids and replace spark plugs. Maybe she could check his dipstick? Take him for a test drive…

“You’re welcome,” she said, “You can fill me up, anytime.”