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Penny’s Predicament

Penny’s Predicament

by Roleplayliterate
19 min read
4.54 (12500 views)
spring breacheatingcucolding
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Friday Afternoon

Penelope's blonde hair whipped in the wind, hand outside the window feeling the rushing breeze as Ben drove through the flat landscape of northwestern Texas. "Are you sure he's going to like me?" She looked over at her boyfriend, one hand on the steering wheel and the other clasping her hand tightly.

"Babe, he's gonna love you. I mean, what's not to like?" Ben gave her a wink and lifted her hand to his lips, giving it a quick kiss before returning his attention to the road.

Penny sighed, even with Ben's reassurance, she still felt nervous. She had a right to be a little nervous. Ben's dad was intimidating. Built like a lumberjack with a stoic temperament and a rough outer shell that was near impossible to crack, he was the poster boy for detached manliness. Having worked with the local fire department for the better part of thirty years, he was as hard as they came. Ben assured her that his dad, Spencer, had a soft side. He was a good dad. Even after the divorce seven years ago, his dad was always involved. Not one birthday was ever forgotten. He called twice a week, like clockwork. He sent Ben money sometimes, just because. He was a good man, and Ben was positive Spencer was going to love Penelope. If for no other reason than because Ben loved her.

They continued driving in silence for a while before Penny spoke. "Sorry, I'm just nervous. I just..." She turned to Ben with a genuine smile. "I kinda like you." She gave him a wink that made Ben laugh.

"That's good. 'Cause I like you too." He leaned over quickly to give her a kiss on the lips.

"Alright. If you say he's gonna like me, I'll believe it." Penny leaned back in her seat, relaxing just a fraction. She crossed her legs, her jean skirt riding up along her thighs, drawing Ben's attention.

"Eyes on the road, perv." Penny chuckled, but didn't make any effort to pull her skirt down. In fact, she wiggled her butt in the seat making her skirt ride up a more so that when she uncrossed her legs, she flashed her pink panties, sheer enough to give a glimpse of her smooth slit.

Ben cleared his throat and adjusted himself, one hand still on the steering wheel. Penny giggled and turned back to watching the scenery fly by.

-- --

Spencer's home was a large, ranch-style house that encompassed several acres of flat, empty land. It was built of solid, dark stone and a dark red shingled roof. It had a rustic feel to it, with the comically traditional decor of large stars signifying, if people didn't already know, that they were in Texas. And Texas had pride.

From what Ben had told Penny, Spencer Galloway was one of those very 'traditionally' tough men. Believed in hunting and fishing. Tough love. Emotions, though important, weren't really supposed to be shared, at least by men, and a quick fist fight or some beer and a ball game could solve most problems. But, even with all of that, which sounded somewhat like red flags to Penny, Ben talked fondly about his dad. The divorce had been difficult for everyone involved, and though his dad was that stoic statue of emotionless stone, he'd mentioned that right before Ben and his mother had moved out, he'd caught his dad crying in his bedroom. As tough as some people were, they still had soft spots.

They pulled into the curved, gravel driveway, Penny admiring the well-maintained yard and hedges. It was clear Ben's dad was the Hank Hill kinda man, meticulously taking care of everything outdoorsy. It was admirable. Also, a sign of him being anal retentive. Uptight. Which just made Penny even more nervous about meeting him. She really, really wanted Ben's dad to like her. She'd met his mom, and she was nice, pleasant, but seemed to be the sort of woman that likes everyone. Spencer was going to be a whole different animal.

When it came to Emily, Ben's mom, Penny hadn't really had to try. She knew this weekend was going to test her. But Ben was worth it. She hadn't met anyone like him and really wanted things to work. The idea of a future with him was very possible, and she didn't want to see it all vanish just because his dad didn't like her. She'd do whatever it took to make a good impression.

Ben got out, leaving Penny alone for a second as she took a few deep breaths, pulled her skirt a little lower, silently cursing herself that she'd dressed comfortably but somewhat revealing. The last thing she wanted was to come across to this man as a hussy. She pushed open the door and stepped out, straightening her t-shirt and for the second time in as many seconds, wishing maybe she'd dressed a little nicer than a Hello Kitty t-shirt to meet her boyfriend's dad for the first time. Ben had told her it wouldn't matter. His dad was uptight, gruff, but he wasn't going to judge someone on the clothes they wore. It was all about character for him. And Penny had plenty of character.

The door to the house opened and a large man came into view, taking up the entire open frame. Scrubbing his hands in a towel as if he'd been doing the dishes, he was a solid man, wide chest, easily six foot, light gray hair and scruffy facial hair that was trimmed tight. As rough and tumble as he seemed, he was well groomed, his dark eyes were firm and unwavering.

Penny had seen some pictures, but for whatever reason, his appearance in those images hadn't triggered the recollection that his presence did now. Her eyes widened as she watched Ben walk up to his dad, arms wide, and gave him a hug. The man hugged back, the grin on his face said he was happy to see his son. A couple hard pats on Ben's back and then he was releasing him and Ben was ushering his dad down the walkway to meet Penny, who was rooted to the ground next to the car door.

There was no doubt about it. Penny had met Ben's dad before. That wouldn't have been such a big deal, people meet people all the time. As large as the world is, it's also very small. The problem, the absolute gut sinking terror that she was experiencing now, was because of where and how she'd met Spencer. She'd tucked those memories away, like the special little keepsakes people collect and put into a shoe box and hide up in their closet. But now that box had fallen out and those memories were tumbling everywhere... explicit and just as vivid as when they'd happened...

-- --

TWO YEARS AGO

"Go ooooonnnn!" Chelsey prodded, almost shoving Penny off the stool towards the older man at the end of the bar.

"What? No! He's old enough to be my dad, Chels!" Penny laughed, shoving her friend right back, then grabbing her fancy, fruity drink that probably had more alcohol than was necessary and took another sip. Her eyes drifted back to the man again.

He was at the end of the bar, elbows on the table, enjoying a fancy beer and watching the television that was hanging at the back, behind the counter. There was a game on, but Penny wasn't paying any attention to it.

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It was the middle of spring break and Penny and a few of her friends had made the rash and somewhat adventurous decision to head down to Dayton Beach and spend the week at the beach and in bars and just being wild. Freshman year in college was supposed to be that time where you let loose, ran away from all those old rules and partied. The other three years were supposed to be for buckling down and getting that degree. Penny wasn't going to argue, especially when one of her friends offered to foot the bill for the hotel rooms. Yay for Daddy's money.

The past couple days had been just that, beach and bars and bouncing from party to party. She'd danced and drank and just β€Œ been wild like never before. Some of her friends had already hooked up with some guys here and there, but Penny had kept herself chaste. Not because she was a prude, but because none of the dude-bro college boys had caught her eye or kept her attention. Let alone get the fire going between her legs.

Now, however, after a couple hours in this new bar, its name long forgotten if she ever knew it in the first place, her eye had landed on this barrel of a man. He was solid and large and his hair was quickly turning from dark to gray, leaving him with that salt and pepper look that she found very distinguished. With all the chaos around the bar, the man had a singular focus on his drink and the television. Nothing seemed to distract him. Which made Penny feel like he was a challenge to be won.

Chelsey shoved Penny again. "Go ahead, girl. You've been eye fucking him for like an hour. Why not go and actually fuck him?" Her friend brushed back her blue dyed locks and picked up her cheap beer, downing the last of it in a single swig.

Penny rolled her eyes, sipping her drink a bit longer, cheeks turning rosy, and looked back over at the man. This time, his eyes found hers. She blinked, unable to look away.

That hard, firm gaze was like a hook, sinking deep inside her and all he needed to do was give a single pull and she'd be reeled in.

Chelsey leaned in and whispered, her breath smelling like beer and spearmint gum, "Well, look at that. Daddy has eyes for little Penelope Winters. Maybe you should go see if he can melt your winter snow."

Penny looked back at her friend incredulously. "Okay, someone's drunk."

"Hardly. I'm two beers away from drunk." Chelsey laughed and once more gave Penny a shove. "Just go! Geez, live some this week."

With a deep sigh, a roll of her eyes, Penny took her drink and made her way to the end of the bar, the man following her with his eyes. She weaved in and out, feeling people bump and brush against her exposed midriff, wearing only a pair of ripped jean shorts and a purple bikini top since they'd gone to the beach earlier in the afternoon. The top bounced along with her breasts, not doing that great at bracing them. But she hadn't chosen this suit for its fortitude. It was flattering, and she liked the looks she got. Especially the look she was getting from this man.

Penny slipped onto the stool next to the gentleman, making sure to push her bottom out a little as she did so. Leaning her elbow on the bar, chin in her hand, she gave him a very flirty smile. "Hi." She batted her pretty green eyes and brushed back some of her blonde hair behind her ear. "How's your evening?"

The man gave a small but charming smile and finished his beer. "Well... it was a bit boring. But, just got a bit more interesting."

Their eyes stayed on each other with a deep, burning eagerness...

-- --

Penny could barely remember how it all happened. One moment she was flirting with a man old enough to be her father, the next she was walking down the block with him to his hotel. She made sure to text her friends where she was going, took a quick selfie with the man because she may have been tipsy, but she wasn't stupid. And now...

The man leaned back in his chair, Penny riding his massive cock hard and eager. Top untied and hanging around her waist, breasts bouncing in hypnotic circles. Jean shorts tossed to the side along with her bikini bottoms. Her blonde, fuzzy pussy stretched wider than she even thought possible on the massive member the man had presented to her when they'd gotten into the room.

"Fuck! Fuck!" She gasped, already sweating. It was hot and the air conditioning in the room wasn't able to keep up. But she didn't care. Neither did the man. They didn't bother with names. It seemed better that way. Safer? More kinky? Or maybe just... fun. Penny would come up with a reason later. Right now the only thing that mattered was how deep he was inside her, the condom straining, and his balls slapping her tight little behind.

His large hands gripped her hips, helping her ride more firmly. "Like that baby girl. Fuck you're tight!"

"You're...just...not used to... teen cunt!" She laughed and breathed as she bounced up and down. His playful, firm grin made her lean forward and kiss him hard, pushing her tongue into his mouth. The smell and taste of beer mixed with their saliva as she made the kiss messy and eager, little drops of spit bubbling and dripping when their lips parted and falling on her tits as she rubbed them against his hairy chest.

Nipples rubbing against his, sweat mingling as she bounced her ass on his strong thighs, they kissed, and fucked. His hands gripped her ass and spanked her firmly at intervals. His grunts were so manly. Fuck. She was quickly realizing she might have a thing for older men. Not that she didn't have crushes or attractions to other men back at school. There was this one boy, in her General Psych class, very cute, light brown hair, sweet grin, kinda boyish. Not like this burly man who was ramming his cock so deep in her little cunt that she wanted to scream. But something about him was... interesting. But that didn't matter right now.

"That's right, darlin'." The man grunted. "Fucking take it. All of it. Fuck yes!"

Penny let out a scream, not caring if the thin walls of the motel let everyone hear her. Let them know she was fucking cumming on a massive cock. Who fucking cared. This week was about fun.

And that's how the rest of the week went. She came back to this man's hotel multiple times. She never knew his name, and he never knew hers. A simple knock. The door would open, and in she walked. Moments later...

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She was upside down, back against the bed, head and shoulders against the rough carpet of the room, her legs hanging open wide and pussy completely exposed. The man towering over her and plunging his massive dick into her tiny little cunt, straight down over and over, grunting like he was trying to mine for gold. She was crying in utter pain and pleasure. His hands covering her perky ass, pulling the cheeks open and spitting on her pink asshole. "Fucking cunt! Yes... fucking take every inch!" He'd gotten rougher and more confident with every visit. And Penny, not necessarily a girl that liked it rough, was absolutely loving letting go of every inhibition.

She would scream, looking up, watching him plunge down over and over, making her orgasm again and again. Then juices would cream around him and drip down her stomach. Pulling his cock out, ripping off the condom and aiming his cock down at her face and open screaming mouth, shooting his massive, thick load all over her face and onto her tongue.

Another day she was under him, her legs around his hips as he thrust hard and fast. Almost a vanilla position, considering the other things they had done and were doing. But it was intense. Deep. Taking every inch of her tunnel and swallowing every inch of his massive dick.

Another day they were in the shower and she was up against the wall, legs around his waist and impaled over and over on him as the water splashed and ran down their bodies.

Other times, she worshiped his cock. Licking, spitting, sucking, nibbling, kissing all over every inch. She was fucking in love with his cock. Stroking it hard and fast, making him grunt. Like they were in a competition to see how far either of them could go with their rough treatment to see who would fold first. She drank his pre-cum and swallowed the thick shots of his ejaculation when he roared in orgasm.

Once she was on his bed, on her back, legs open, his hand between her thighs thrusting three fingers deep and fast. Rubbing her g-spot relentlessly. She held tight to his other arm, the hand around her neck squeezing just enough to make it a struggle to breathe. It only took her minutes to cum and squirt all over his bed. Then he flipped her over, pushed her face into the wetness she'd just made, and rammed his cock into her when she had her ass up in the air and fucked her to another orgasm, quick and dirty.

The entire rest of the weekend was a sexfest. Penny came innumerable times. She drank so much cum and got so much painted all over her skin she was afraid she'd get pregnant just by it soaking into her body even though he'd never cum inside her. And then...

Then it was over. She was on her way back to school. No names. No numbers. Not even a goodbye. They had just been fuck buddies for a few days and that was it. It was exhilarating. Freeing. She took that memory, packaged it up and set it aside for late nights when she needed a little help to masturbate. Otherwise, they were put away as a fond memory. Nothing more.

-- --

PRESENT

If Spencer recognized Penny, he didn't show it. He followed Ben and stuck out his hand with an emotionless gaze. Penny took it and shook. "Um..." She cleared her throat, trying to push past her surprise and embarrassment. Maybe she'd changed over the last couple years so he didn't recognize her. She was wearing her hair longer now. "Hi. It's so good to meet you. I'm Penelope." Penny gave him a bright smile.

"Nice to finally meet you, Penelope. My son has told me a lot about you."

"All good, I promise." Ben chuckled and gave Penny a quick kiss on her cheek. "I'll get the bags, you go inside. Dad's just started cooking some burgers." He walked past Penny to the trunk of the car.

"Uh. Okay." Penny bit her lip. Spencer motioned for her to follow and she took up step next to him as they went into the house.

"Thanks for having me this weekend." Penny managed, hoping beyond hope that Spencer didn't remember her or, even better, maybe she was wrong. Maybe this man wasn't the one she'd met on spring break her freshman year and fucked for days.

"No problem at all. It's usually pretty boring around here." He ushered Penny through the house and out onto the back patio that opened to a large backyard with a sizable pool and a built-in grill that had fresh burgers already beginning to sizzle. "But..." Spencer went to the grill, putting on a worn apron and picked up a spatula, then settled his gaze back on Penny as she stood under the canopy of the patio, "Now that you're here, I think things will be a bit more interesting."

Penny's heart skipped. Her eyes widened. Spencer didn't smirk or give any other indication that he recognized Penny, but she knew in that second, Ben's dad remembered her. Remembered everything. And to her mixture of embarrassment and horror, she felt her panties become damp.

-- --

Even though the evening was coming on quick, Spencer insisted they use the pool while he cooked. It was heated and lit well by hanging lights and underwater lighting. He'd built the whole thing himself last year. A project to keep himself busy.

"Semi retirement is almost like full retirement." He told Ben gruffly when asked if he'd been picking up any shifts at the firehouse. "Pretty much nothing to do unless they come up short handed. Thankfully, they haven't had any emergencies that needed to call in us old guys. But... I'm here and ready to go."

Penny was still trying to come to terms with the revelation of who Ben's dad was, but she couldn't let Ben see her in distress. The best thing to do would be to pretend like they didn't know each other. It was two years ago. Ancient history. Just a fling. A hit it and quit it sort of season. Nothing more. No need to bring it up. Just... pretend like it wasn't a thing.

So she went inside to the room Spencer had made up for her and Ben. It was sort of progressive of him to assume they'd be sleeping together. No old school values in this house, it seemed. Of course, considering what Spencer had done to her that week.... No! No. She wasn't going to think about that.

Pushing all the memories that desperately wanted to come lunging back into her life, she unpacked a few items and found her bathing suits. She'd brought two. A cute purple one piece racing suit and a much more skimpy, gold halter style triangle bikini. Mostly string and a few triangles of fabric that would just barely cover her intimates. She'd packed that one for more of a tease for Ben. Maybe if they'd gotten some alone time at the pool, she was gonna whip it out and give him a little... Well, now that didn't seem like a good idea, considering who was outside...

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