Daddy Issues

Story Info
An older man and a younger co-worker.
4.6k words
4.72
36.3k
43
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Jenny has 'Daddy Issues.'" Bart had been informed of this on the very first day at his new job. It was kind of an open secret related to him by the co-worker conducting his orientation.

"She's, like, 26, and she has a thing for older guys, 'cause her father left the family about 10 years ago," the co-worker told him.

Bart, being -- literally -- twice Jenny's age, tried to concentrate on learning his job. He could not, however, help admiring Jenny. She was beautiful; there was no denying that. Her deep brown eyes were hypnotic. Her pink lips tantalizing. Her shoulder-length, peroxide blonde hair enchanting. Her figure perfect. She possessed C-cup breasts. And, her ass was simply spectacular. Jenny's only flaw -- if it could be called that -- was a slightly -- barely -- crooked tooth. Bart found it endearing; as if it proved imperfection's perfection.

On top of all that, she was ridiculously smart, funny, free-spirited, and open-minded. And, she possessed an almost encyclopedic knowledge of 1980s music -- the music of Bart's teenage years.

As months passed, they worked together regularly, and grew more comfortable with each other.

"I like being paired up with you," she'd told him one day. "You make me feel safe."

"I... uh... thank you," he said; not knowing how to respond.

Jenny hugged him; his heavy, 6'3" frame dwarfing her petite 5'6".

"You're one of my people," he managed to say. "I always try to protect my people.

Occasionally, when partnered, they'd remark on various women coming through their station. It seemed they both had a "thing" for women wearing wet-look, pleather leggings, and each time the subject came up, Jenny commented that she needed a pair... soon.

Due to the large difference in their ages, Bart -- believing discretion the better part of valor -- avoided pushing the conversation too far, or becoming too explicit. Eventually, though, as they spent more and more time together, they would tease with double entendre, even sexually graphic comments, related to their conversations. And, Jenny would even mention her plans to go shopping, and buy some leggings.

One Saturday evening, while working together, she playfully responded to something he'd said with "Yes, Daddy." Initially, he rejected the response, telling her he would never let a woman call him "Daddy" or "Sir." Later that night, however, he changed his mind, telling her she would be the first, and only, woman allowed to do so. Bart tried to remind himself not to take things too far. It wasn't working.

On Monday -- his Saturday -- Bart had errands to run; multiple stops to make before he could relax and enjoy his weekend. He walked into a store specializing in products for the bedroom, bath room, and other rooms, seeking a picture frame. He was browsing the shelves when he heard a familiar voice.

"Hey, Bart."

He turned to see Jenny standing before him. She had no make-up on, and Bart thought she was more attractive than she ever was at work. She wore a white t-shirt; loose, orange nylon running shorts, and sneakers. He could see the faint outline of her nipples through the thin fabric of her shirt.

"Hey," he answered; trying to focus on her eyes.

"What are you doing here?" she asked.

"Just looking around," he answered. "You?"

"Searching for a wedding gift for some friends," she told him.

He could feel himself hardening in his sweatpants.

"Any idea what they need?" he inquired, hoping she wouldn't notice.

"None," she admitted, with an exaggerated frown.

"Well, I could help you look around," he offered.

"Thanks," she replied, smiling. "I appreciate that."

She whirled around to lead him on their quest, and he realized the bottom of her ass cheeks were visible below the hem of her shorts.

"Jesus fuckin' Christ," he whispered to himself.

They made their way through several aisles, finding little that piqued her interest. While Bart barely noticed the products on the shelves -- his attention was fixated on Jenny -- she lingered here and there, inspecting a few items.

The two reached the back of the store. As they attempted to step around the racks of hanging area rugs, Bart put his right hand on Jenny's lower back, to steady her. She jumped at his touch, but his hand remained on her.

"Are you OK?" he asked.

"Are you?" she scoffed, looking down at the front of his sweatpants.

She reached out to touch the fabric.

"Holy shit, Bart," she exhaled, quietly, when her hand found his hard shaft.

Quickly, he glanced around the store. He saw no one. Though he knew there had to be cameras on them, at this moment, he didn't care.

"Are we done teasing each other?" he challenged.

Before she could answer, his hand fell to her ass, and he pulled her body against his. Looking up into his eyes, she stroked him through his pants. His left hand slid between her legs, and he pressed his fingers against her clit.

"Fuuuuuck," she cooed.

"I'll take that as a yes," he growled.

He kissed the side of her neck.

"We need to go somewhere," she urged. "Now!"

"My place, or yours?" he grumbled, briefly taking his lips from her. "Yours is closer."

"Ami is home," she whined; referring to her roommate, a co-worker of theirs.

"OK," he proposed. "My place."

"I can't wait that long," she panted. "Someplace closer."

"Come with me," Bart ordered.

Taking her hand, he led her out of the store. He walked her to her car and told her to follow him. Climbing in his SUV, he led her to the far end of the strip mall's parking lot. She parked beside him and jumped out of her car.

"Back seat," he called out as she approached.

Sliding from the driver's seat, he joined her; suddenly thankful for the tinting on the side and rear windows. She straddled him even before his door slammed shut. Their mouths mashed together, their tongues danced, and they tore at each other's clothes. Bart lifted her shirt and tilted his head to take her left nipple in his mouth. She gasped and wrapped her arms around his head, pulling him to her chest.

"Yes, Daddy," she cried, as he sucked hard, flicking it with his tongue.

He slipped his hands inside the bottom of her shorts and pinched her ass. She yelped and raked her fingers through his short hair.

"No panties, either," he observed. "Dirty little girl."

Bart flipped her over, awkwardly maneuvering Jenny to place her on the seat, reclining against the door. Kneeling on the seat, crouched down in the small space, he grabbed the waistband of her shorts and pulled them downward. She lifted her ass, then her feet, allowing them to slide off. Bart dropped them to the floor. She stripped off her shirt; tossing it atop her shorts. Now nude, except for her sneakers, Bart took a few moments to admire her body. His eyes lingered on her shaved pubic area.

Jenny reached down, slowly tracing a finger along her lips. Bart kissed her inner thigh; gently at first, then harder; before nibbling on her incandescent skin. He could smell her sex, and it intoxicated him. Bart trailed his tongue to her; pressing it against her pussy; tasting her for the first time.

"Yessss," she hissed.

Once more, her hands clutched at the back of his head, and she pulled him into her.

"Mmmm," he muttered.

He brought his right hand up, and a finger joined his tongue in pleasing her. Lightly, he brushed it over her flesh, getting it wet with her juices; then slid it inside her while his tongue concentrated on her clit.

"That's it, Daddy," she mewled, squirming. "Eat my pussy."

Her legs slipped over his shoulders as he increased the speed and intensity of his efforts. Bart added a second finger to her pussy -- working them in and out, hard and fast.

"Shit!" Jenny shouted.

His left hand traveled up to her breasts, after fondling them briefly, he continued to her throat. Squeezing, he limited the flow of blood to her brain.

"Yes," she rasped, barely having the breath to form the words.

He hummed in response, sending vibrations through her -- from head to toe, and Jenny plunged into ecstasy; writhing under Bart's touch.

"I'm cumming," she cried. "I'm cumming!"

Bart didn't stop, or even lessen, his carnal assault. He continued licking, sucking, and fingering Jenny, determined to make her cum again before her first orgasm faded away. He succeeded, and then some. As Jenny's first climax blended into her second, Bart slipped from between her legs and clumsily crawled up to kiss her. Her arms encircled his neck, and she hugged him tightly as she tasted herself on his mouth.

Bart removed his sticky fingers from her cunt and turned his hand to rub her slippery clit. Jenny jerked violently, and she moaned into his mouth as she came again, and again; her second orgasm rolled into a third; which rolled into a fourth.

Escaping her grasp, Bart straightened himself -- as much as he could in the cramped confines of the back seat. He watched Jenny shake as he manipulated her clit, intending to make her cum a fifth time.

"No, please..." Jenny begged. "Please, I need to breathe."

Looking down, he surveyed her quivering body bathed in sweat -- a combination of their exertions, and the rapidly rising temperature in the closed car -- her hair tangled from thrashing around, and her chest rising and falling as she took in large gulps of air.

"You've been a good little girl; cumming four times," he said, whispering in her ear.

"You didn't give me a choice," she whimpered.

"Guilty," he admitted.

"You have magic fingers," she complimented.

"One of my many talents," he bragged.

"If you ever do that to me again," she murmured, "you can be my Daddy forever."

Bart kissed her chest, then began kissing his way down across her stomach. His fingers trailed up her inner thigh toward her pussy. She shoved him away and struggled to wiggle out from under him.

"Shit! Not right now," she shrieked. "You'll give me a heart attack!"

"I'd bet I could make you cum another half dozen times before that happened," he joked.

Curling up, Jenny slouched against the passenger's side door. Bart spun to sit on the opposite side.

"Are you OK?" she asked, pointing to the bulge in his sweatpants.

Rocking side to side, he worked his pants and boxer-briefs down to his ankles, freeing his cock. Above average in length and girth, it stood up between his legs.

"Oh, my God, Bart," she sighed, staring at it.

Not taking her eyes off his cock, she crawled over, turned, and straddled him. Raising her eyes to his, she began rolling her hips; grinding herself against him. He pulled off his t-shirt, and she pressed her sweaty body against his.

"I thought you needed to recover," he taunted.

"I'm feeling much better," she assured him, with a smile.

"Good," he noted.

Reaching up, he grabbed a handful of her hair, and tugged; forcing her to lean back. Again, he took her left nipple in his mouth. Tasting the salt of her perspiration, he sucked hard, and flicked it with his tongue. She wrapped her arms around his head; pulling him to her.

His hands cupped her ass. He could feel her hot cunt rubbing against the shaft of his cock. Her juices ran down to his balls, and Bart groaned as he licked her.

"You like that?" she goaded. "Feeling my wet pussy against you?"

Jenny rose up, and Bart slid his hand between them. Gripping his cock, he guided the tip to her.

"I want to fuck you," he said, looking up.

"Do you have a condom?" she asked.

"No," he admitted.

She hesitated; but she wanted the same thing.

"Just don't cum inside me," she insisted. "I'm on the pill, but we have to be careful."

"I won't," he affirmed. "I promise."

Lowering herself, she took the head inside.

"Jesus, Bart," she sobbed.

Gradually, she took him deeper; gliding up and down; further lubricating his shaft with her juices. Her breathing quickened as she fully enveloped him. For a moment, she stopped, resting; adjusting to him.

"I've wanted this for so long," she confessed.

"Me, too," Bart told her, his fingertips trailing along her spine.

She trembled under his touch, and began moving her hips back and forth, shifting his cock inside her.

"It feels so good," she purred.

Placing her hands on his shoulders, Jenny began rising and falling; riding Bart.

"That's it, Baby," he thundered. "Fuck me!"

Steadily, she increased the speed and intensity of her efforts, until she was slamming herself down on him. She cried out each time her ass smacked against Bart's lap. He seized her hips -- his fingers digging into her torrid flesh -- trying to ram her down on his cock with that much more force.

Jenny's cries turned into grunting the word "yes" each time she impaled herself. Bart could feel the familiar ache growing in his balls; he knew he couldn't last much longer. They were both fighting for breath when Jenny suddenly slowed her bouncing. She stiffened, and moaned loudly -- the sound filling the vehicle.

"I'm gonna cum again," she announced, through gritted teeth. "I'm gonna cummm..."

She descended upon him one last time and stopped. Her pussy constricted around his cock, and she convulsed as she came yet again. Her orgasm pushed Bart over the edge.

As the ability to form coherent thoughts quickly faded, Bart battled to slip his hand downward to wrest his cock from her -- honoring her request that he not cum inside her. Instead, his cock trapped between them, he shuddered and fired stream after stream of cum that mixed with the sweat pouring off them both. The car rocked as they came together.

Jenny buried her face in Bart's shoulder; her anatomy all but fused with his. They remained there, hugging each other's damp bodies, as they recovered. It took nearly five minutes for their breathing and heart rates to return to normal.

"Are you OK?" he asked, finally.

She didn't answer. He waited a few moments, then shook her gently.

"Are you still alive?" he questioned.

"I'm cum-drunk," she rasped, turning her head just enough to look at him. "You made me cum so many times my brain is scrambled."

"What's your excuse the rest of the time?" he quipped.

"Hey!" she protested, giving him a soft punch in the side. "Be nice."

"I'm sorry," he chuckled, then kissed her shoulder.

"Thank you for pulling out," she said. "I was too busy going crazy to make sure you did."

"Of course," he commented. "I promised you."

"Don't do that," she groused, as his lips drifted to her neck. "You'll get me started again."

"That's the idea," he murmured, continuing.

"I do want more. But, not here. I'm literally melting in this car," she lamented. "Do you want to go to my place?"

"Absolutely," he responded, without delay.

"We have one problem," she pointed out. "I think our sweat, and your cum, have glued us together."

"You might be right," he agreed.

They relaxed for a few more minutes, before gingerly peeling themselves apart. Each used their t-shirt to clean themselves as best they could, then dressed inside the car. Opening the door, they nearly tumbled out of the back seat, and then paused to take great gulps of the cooler air. Revived, Bart agreed to follow Jenny to her house, provided they make one stop along the way.

Walking into a drug store the two were a spectacle -- their shirts soaked in sweat and sticky cum; Jenny's was almost completely see-though, and her hair disheveled -- they appeared as if they'd just been mugged by a gang of kids armed with Super Soakers. The cashier gave them the side-eye the entire time she spent ringing up their liter bottles of water and a box of condoms.

Bart paid, and the two resumed their journey. He rehydrated as he drove -- all four windows down to help his back seats dry. Only minutes later, they arrived at their destination.

Jenny took his hand and led him to the front door. She unlocked it and they slipped inside. As she closed the door, he picked her up. She wrapped her legs around him and he carried her up a set of steps to the main level of the house.

"Hi, Ami," Jenny sang out, looking to her left, into the living room.

"Hey, Ami," Bart echoed, still holding Jenny, his hands cupping her ass.

"Uh, hi..." the brunette returned from the couch; a confused look on her face. "What are you doing here?"

"Me," Jenny hooted, giggling.

"I..." Bart began, "we... ummm..."

"We ran into each other at the store," Jenny told her.

"Well, it's about time you two 'ran into each other,'" Ami opined.

"Should we go to the bedroom?" Bart whispered in Jenny's ear. "Or, should I fuck you right here?"

"This way, Daddy," she instructed, pointing down a hallway.

Bart proceeded in the direction Jenny indicated.

"Have fun, you crazy kids," Ami encouraged.

After entering Jenny's room, he set her on her feet, and turned to close the door. When he again faced her, she was removing her clothing. He did the same. Once naked, she picked up a pair of fluffy towels.

"Come on; we need a shower," she insisted.

"We certainly do," he echoed.

She led him to the bathroom. He focused on her ass as she leaned in the shower to turn on the water. She caught him staring, and smiled as she wiggled her butt for him.

Jenny stepped into the stall, turned, and crooked a finger at him. He joined her. The water was cool, and -- after the heat of the car -- refreshing. Rotating in the spray, they caressed each other, rinsing off the sweat and cum. Jenny snatched up a bottle of body wash, and dribbled a generous portion of the green goo into his hands. He rubbed them together, then reached out to soap her chest. Slipping his hands around her, he hugged her tightly as he scrubbed her back. She squirmed against him, cleansing him as she did so.

Bart turned enough to slip one hand between her legs from the front, and the other behind. She rose to her tip-toes as he manipulated her clit and nudged a fingertip against her asshole.

"Fuuuuck," Jenny yelped.

"We will," he assured her, chuckling, "when we're done in here."

"You're teasing me," she whined, her bottom lip sticking out in a mock pout.

"Let's go to bed," he suggested.

Jenny and Bart twirled deliberately, flushing away the soap. As the suds circled the drain, he kissed her hard and they groped each other desperately. Eventually, she pushed him back half a step, and reached out to shut off the water. For a minute, they remained in the stall as water dripped to the floor, then Bart grabbed a towel and began drying her.

"My hair is a mess," she groused.

"You are bewitching," he countered.

"I look like a witch?" she sniffed.

"No," he argued. "You're beautiful."

"You're a liar," she disagreed, even as she smiled at the compliment.

Putting the damp towel around his shoulders, he picked up the dry one and draped it over Jenny's shoulders.

"Such a gentleman," she crooned.

"Ladies first," he said, standing aside to let her exit the shower stall.

"You know, we know guys only do that so they can stare at our asses," she revealed.

"Can you blame us?" he challenged.

Jenny wiped her feet on the bath mat, then scampered into the bedroom. Bart followed at a leisurely pace. Entering, he saw her turning on a small fan aimed at the bed. Tossing her towel toward a hamper, she crawled on the bed. After retrieving the box of condoms from his sweatpants, Bart did the same. Lying beside her, he tore open the box and poured out the contents.

"Ribbed for her pleasure," Jenny observed.

"I'm all about your pleasure," Bart explained.

"Only three?" she teased. "Not very ambitious."

"I seem to remember someone who looks a lot like me making you cum five times in the back seat... without a single condom," he scolded. "Maybe, I'll just keep my magic fingers to myself next time."

"Nooooo...," she objected. "I'm sorry."

Jenny placed a hand on his inner thigh.

"I'll make it up to you, Daddy," she offered, with a wink.

12