Work Text:
Summer Vacation.
The two most tantalizing words in a high schooler’s lexicon, especially when the thick snows of December were still falling. All throughout school, young mouths swore up a storm about the piled-up snow they were forced to march through, rubbing runny noses and shaking ice off boots. As they grumbled and slipped on wet tile floors, their minds all wandered to summer- when they could cast off the chains of education for three months, and party it up with each other until the next two semesters of drudgery.
Anna Mavis, long-time high school student and recent legal adult, was no different. As the howling winds outside carried a new layer of powder to the ground, her face was staring straight ahead at her school laptop, grinning as she typed in more figures into a spreadsheet- smiling dreamily as she let a happy sigh leave her lips.
“Hey Anna, what’cha got there? A project?”
She started a bit at being addressed- only to look back up into the face of her friend, Mark Sheppard. Giving him a quick, radiant smile (which had him redder than a cherry) she put on her most important airs, gently prodding her screen.
“Of a sort, Marky!” She grinned, jabbing the title of her spreadsheet. “You are currently looking at my master plan for the rest of the school year- and the summer, too! Behold~!”
Mark leaned over her shoulder and hummed- eyes scanning the page. It looked like a budget, amateurish in the extreme- but what caught his eye was the title at the top.
“The Great American Road Trip, Anna Mavis Style Budget Plan?” He asked- getting a squirm in response.
“The title could use some work, I’ll admit, but that’s the idea! I save up a buncha money, rent a car for a couple weeks, and drive it all around these beautiful states of ours, setting up on beaches, mountains, and glorious vistas- just me, my gumption, maybe some truck stop showers…It’ll be my rite of passage into adulthood!”
Mark snickered as Anna flourished- gloating over her master plan with stars in her eyes- looking over the spreadsheet and whistling at the final figure.
“Eeesh, seven kay, Anna? Sure you aren’t setting your sights a little high?” He asked- only getting a shrug in response.
“Well, it would be five…but I really wanna be driving a Corvette around. They’re expensive, ya know.” She mumbled- clicking over to the rental car site and showing him personally. “It’ll be tight, but doable- I have January through the end of August to earn it up, and I made sure to leave a little bit for job hunting. I may have to shave off a day or two- or even a week- but I think I can get it done.” She said with a smile- which was reciprocated by her friend…
Who promptly stopped smiling when he remembered something.
“Hang on- do you even have a job?”
Anna just waved him off.
“Oh, please, that’s the easy part. Young go-getter like me? I’m sure there’s a buncha places dying to hire me!”
Mark could only squirm- tugging his collar as he tried to help his friend face reality.
“Anna, I really think you should start looking right now. Places are wicked competitive these days.”
Anna could only scoff- folding her arms triumphantly, already thinking of sailing across Route 66 in her Corvette.
“Oh please. How hard can it be to get a job?”
“We’re sorry, but we’ve already picked a candidate for the job. Thank you for your interest, though.”
Really.
“Sorry, we’ve hit our hiring quota for the next couple’a months now. Maybe try again in a few.”
Freaking!
“Still in high school? Sorry, I need someone who can work nights.”
HARD!
Anna let a defeated groan leave her lips as she banged her head against her locker- moaning as students hustled around her. Job hunting, she was beginning to learn, was a soul-sucking experience that not only left her feeling like there was a yawning pit where her heart should be, but had also been completely fruitless. It was almost February, and the only thing she had to show for her work were a couple of interviews that went nowhere- if she got contacted at all.
She lifted her head from her locker as she gently rubbed at the bridge of her nose. She had allowed for a few weeks of no progress in her budget, but at this rate, she was going to spend all of February hunting. If that happened, she’d need to get hired in March, and would have to somehow snag a job paying at least nineteen an hour, working the maximum amount of hours she could as a student. She needed a job- and she needed one as soon as possible. She had asked around, talking to her relatives, friends, begging on social media- everywhere that she could think of to find a decent place to work had either rejected her, or just didn’t have anything for her.
At this rate, she was going to spend her last summer break before college just sitting around playing video games and working. Her grand glorious plan- burning before it got off the ground.
“I take it the Great American Road Trip, Anna Mavis Style isn’t going well?”
An aggravated grunt left her lips as Mark opened his locker beside her- putting everything he’d taken out that morning back in. Anna, still despairing, slowly began to open hers to do the same.
“Still working on the name.” She mumbled miserably. “I just don’t understand…! Everyone’s got a damn banner saying they’re hiring, so why not me…?!” She whined- only receiving a shrug in response.
“Places like that are pretty much staffed already. They just put up those banners to make it seem like they’re hiring and look more inviting.” He grunted- earning a shocked look.
“What?! That should be illegal!”
“It might be, but do you think anyone’s gonna bring suit against them?”
An anguished groan left her- as she hung her head again.
“Stupid bullshit job…if I had gotten one, I could be saving up right now…”
Mark reached over to pat her on the shoulder- offering her a smile.
“Well, so long as you’re free tonight, how about stopping over at my place? My Dad’ll be home, we’ll play some games, have a pizza- make a night of it.”
Anna slowly looked over at him- favoring him with a more muted smile of her own.
“Yeah…yeah, I think I’d like that. Thanks, Mark. I’ll get settled here and get on the bus. You ride number thirty-four, right?”
Mark grinned- as she began to put her stuff up with a little more pep in her step.
“That’s the one- seventh stop.” He smiled, putting his things away. “Join you there- I need to nab my stuff from orchestra. See you soon!”
Anna grinned- giving him a little wave.
“See you soon!” She chirped- sending him away on cloud nine. Anna’s plan may not be getting off the ground- but his plan to spend as much time with her as possible- that one was taking off, and nothing was going to hold him back!
Well, nothing, except, for the orchestra in the band room, somewhat testily informing him that they had a mandatory practice that day.
And his phone being dead so he couldn’t tell Anna to wait up.
And Anna getting trapped on his bus home, taking her miles away from her home in a picking-up snowstorm.
“Shit.” Both of them sighed- miles away, but united in the ashes of ruined plans.
“A-and th-that’s the situation…”
Anna shivered as she hovered next to the roaring fire, clutching a fluffy bathrobe closer to her frame, recounting her tale of woe to Mark’s father. Having no choice but to go to Mark’s house, she trudged through the deepening snow, feeling the cold seep into her bones. When she arrived, she was a sniffling, shivering mess- her clothes had been soaked through by the wet January snows, and she, to put it mildly, was in desperate need of warmth.
So, Alan Sheppard stood aside, let her rush into the heated foyer, and take his ex-wife’s bathrobe while she let her clothes tumble in the dryer.
Mr. Sheppard could only whistle as she finished her tale- slipping a cup of hot cocoa into her hands.
“Damn, kid. Sounds like you’ve been through the wringer today.” He hummed- giving her a comforting pat on the shoulder as she shivered- gratefully drinking the hot drink in her hands. As Anna took the cup away from her mouth, she could only sigh in response.
“Tell me about it. It feels like the universe is going out of its way to kick me in the a…in the butt lately.” She grumbled- blushing as Mr. Sheppard scoffed at her attempt not to swear.
“You can say ass here, kid. We’re not at the firm. You talking about that ‘Great American Road Trip, Anna Mavis Style?’” He grinned- making her splutter a little.
“I…I’m still working on the name…” She sulked- as Mr. Sheppard laughed. “And yeah. No place is willing to hire me. I need seven thousand before mid-August, but that…”
“…Is looking pretty out of reach.” Mr. Sheppard finished- Anna flinching in response- but could only nod as reality set in. “I hear ya- job hunting is rough. I got real lucky when I was hired onto the Law Firm- my old man swung me the position.”
Anna groaned as she leaned back in her seat- sighing as a bit of her robe fell open, exposing her collar to the heat of the fireplace.
“Friggin’ hell…if I want my summer plans to go through, I gotta get hired soon. I’ll do anything, at this point.”
Her eyelids fluttered closed as she turned away from him and to the fire- as Mr. Sheppard stood silent at her side. He hummed softly, letting his eyes fall from her face- trailing down her figure as she relaxed in the heat. His hand gently rubbed her shoulder as she let a low, soft moan leave her lips…
“…Well, I wish you luck.” Mr. Sheppard smiled- before turning about. “Take as long as you need by the fire, and feel free to make yourself more cocoa if you need it. I’ll be up in my office, catching up on paperwork. Buzz me if you need me.”
Anna’s eyes snapped open- smiling back at him.
“Sure thing, Mr. Sheppard! Thanks for the cocoa!” She grinned- taking another drink with a low purr of delight.
Alan swallowed around the lump in his throat- and swiftly turned away, feeling a tightness in his trousers…
“No, thank you…” He murmured- completely inaudible as he climbed up the stairs to his office.
Alan Sheppard had lied to Anna. He wasn’t going to his office to file, look over, or fill out any little bit of paperwork.
The minute he stepped over the threshold, he locked the door, massaging the bulge in his pants as he walked over to the armchair in the corner- where he unzipped, tugged his cock out, and started to slowly stroke himself to the thought of the young woman downstairs- wrapped in nothing but a fluffy bathrobe to protect her modesty. His phone rested in his other hand, looking over the pictures he had taken discreetly- of the show Anna had unwittingly put on for him.
He bit his lip, moaning softly as his hand sped up, eyes burning every detail of her into his memory. She had only turned 18 five months ago, but she already had a body that co-eds would kill for. Fat ass, thick thighs, huge tits, and a cute face framed by a bob of golden blonde hair. His thumb flicked across his phone, showing a picture of her in her soaked clothes, clinging to every curve- zooming on her breasts as she unzipped her hoodie. Grunting, he moved to the next picture, where she was shivering next to the fire- bent over and straining the seams of her pants with that bubbly butt of hers. The next picture had been taken a little later- of her, with her shirt riding up- showing the white lace trim of her panties, digging into her sides…
And then he moved to the video- the video he took through the crack in his bedroom door- thanking whoever was listening that Anna didn’t close it fully.
Panting now, his hand gripped his cock tight as he watched Anna peel away her wet clothes-stripping away her shirt, pants- and the soaked sunshine yellow bra and panties, leaving every last inch of her bare…stretching gratefully in the heat of the room. He paused, outright drooling as he froze the video on her, back arched- arms to the sky- mouth open in a low, lingering moan- letting the phone in his hand slip from his grasp as his eyes fluttered shut- slipping into a fantasy…
She opened the door, wanting to ask him a question- only to gasp and cover her mouth as she watched him moan his name, pumping out thick, white ropes of cum as he finished. Before he could hope to explain himself, the little minx just smiled, and crossed the distance. Before he knew it, her lips were between his thighs, sucking cum out of the stains on his pants, before that warm, juicy tongue started to clear the cum on his cock…
“Mmmm, Alan…are you this worked up over me?” She breathed, her voice coming out in the low, husky moan of a pornstar. Her fingers gently stroked his spit-stained member as those soft, soft lips brushed against the tip- causing him to arch his back like a bolt of lightning had hit it. “Poor boy, working in here all day…just sit back and relax…I’ll do anything you want~”
As Alan felt a tightness in his core, a jolt crossed his mind- tearing him out of the fantasy and back to reality.
“I’ll do anything you want~”
He had heard that. His imagined voice had been knocked away, and instead had sounded like her actual voice- so much so he was worried that she had gotten in. But no- the door was still bolted, and she was still downstairs- presumably…
“I’ll do anything, at this point.”
His throat ran dry as he thought about her words- what she had said to him…she was…
Desperate.
Slowly, he rose- stuffing his stiff cock back into his pants. Shakily, he crossed the room and opened a door- pulling back the false spines of a few legal briefs to expose his safe. Punching the combination with shaking hands, he opened it- and withdrew a bulging pouch of money from the depths. He had taken great pains to keep this stash private, untraceable, away from prying eyes…
Thoughts began to form in his head- of waving the stack of money around in front of the barely-legal woman, coaxing her to sell her body to him. His fantasies came roaring back, of him pounding her into the walls, the beds, and every last surface in the Sheppard household…
He could have it- if he played his cards right…
His cock ached in his trousers. Ever since his wife had left, he hadn’t had a date in months. Hadn’t had sex in almost a year. He had sated himself with his hand and a few raunchy videos at night, but he remembered just how good it had felt- and how desperately he wanted it…and now, he had a chance…all he had to do was offer…and maybe offer her some money if she refused. His breathing picked up again- and his now-steady hand pushed down the intercom button.
“Anna- can you come up here for a moment? I need to talk to you about something.”
He chuckled briefly at the squawk of surprise- only for her to collect herself quickly.
“Uh-sure thing, Mr. Sheppard! Be right up!” She chirped.
When Anna crossed over the threshold, Alan fought to keep his expression neutral, and his heartrate down. The sight of her in his ex-wife’s robe, the robe that had tumbled off her shoulders so many times- only pumped more blood, his desire starting to burn in his chest…
“You, uh, you wanted to see me, Mr. Sheppard?” She asked- fiddling with her hands as those beautiful blue-green eyes stared up at him.
Alan tried to calm down- relaxing in his seat and nodding as he gestured to the chair across from him. Anna slid into without a word of complaint which brought a smile to his face- at her obedience.
“Yes, actually- I was thinking about it in my office, and I think I have a solution to your little money problem.” He said- grinning as Anna’s face burst into a wide smile.
“R-really? You can get me a job?!” She asked. “Yes! Yes, I’ll do it! I’ll do anything you ask, Mr. Sheppard- I’m ready!”
He scoffed a little bit at her blind enthusiasm- waving a bit and trying to ignore the throb down below as she said those words again.
“Settle down, Anna- I haven’t even told you what you’ll be doing yet.” He smiled- standing up as she settled back down. With no preamble, he immediately set a stack of one-hundred dollar bills on his desk. Anna’s complete and utter shock was written clear on her face at the figure on the band- ten thousand dollars. As Anna stared, gobsmacked- Alan circled around to her back, placing a hand on her shoulder.
“This is a bit of money from my stash. I keep it on hand for more…private matters that I don’t want traced back to me.”
Anna stiffened in his grip- as his other hand took her other shoulder, gently rubbing circles as he leaned over her.
“You see, Anna- you need money…and I need something that money usually can’t buy.” He purred- leaning down to Anna’s ear to whisper. She shuddered in his grasp, her eyes never straying far from the stack of bills on the table. Her hands clenched- hiking up the hem of the robe slightly, as her breathing picked up.
“I need you.” He murmured- startling Anna out of her reverie- causing her to violently shake out of his grip- turning around and thumping against the table.
“M-Mister Sheppard!” She shouted- face bright as she clutched the robe tightly to her body- suddenly aware of just how vulnerable she was. “A-are you crazy!?”
Alan hummed- shrugging at the turn of events, mind moving a mile a minute on how best to convince her.
“Nope. I’m one-hundred percent in my right mind.” He lied- some part of him knowing that there was no way he’d be offering this if he were in his right mind. “I have money, you want money- and I think we can help each other. What, is there a problem with that?”
“Y-YES!?” She yelled- disbelief clear on her face. “You’re asking me to- you’re soliciting- you’re old enough to be my Dad! I-I’ve only known you for like- three hours!”
Alan bit down on his cheek- leaning over her, causing her to try and stumble back. Gasping, her left hand hit the money, grabbing instinctively- and sliding, landing with a thud on his desk- flat on her back. When she stumbled, her robe had fallen open again, showing cleavage down to her stomach as she looked up at him- wide-eyed and panting.
Trembling. Vulnerable.
Alan’s passions flared- planting his hands on the table, pressing the bulge in his trousers against the strip of bare thigh that the robe was revealing. Anna gasped, squirming- but she had no way to get up again, not with Alan trapping her…
“Anna…” He breathed- voice low and husky. “I want you. I’ll pay for you. Hundreds. Thousands.”
Anna shuddered as her grip tightened- holding the massive wad of bills in her hand. Her mind began to swim, thinking about the money he was offering- just how much would he be willing to part with? She could have it all, if she played her cards right-
She shook her head- what was she thinking?! She wasn’t going to whore herself out to her friend’s father just for a road trip! She wouldn’t- she wouldn’t!
But then, she felt something hit her hand. Opening her eyes, she saw that Alan had now placed another stack of hundreds into her right hand- leaving her holding, in her hands right now, twenty thousand dollars.
“Well? I’m waiting on an answer.”
Anna looked between her hands- biting her lip. Mr. Sheppard had offered her way more than her road trip at this point- this was college money! A free semester wherever she wanted to go- more, if she wanted to go to community college!
Her breathing came to her in low, deep gasps as she wrestled with herself- feeling her face flush with heat as she felt her willpower melt away…
She…
She wouldn’t. No. It’d be betraying Mark, on one hand, and just…inappropriate on the other.
‘Just say no.’ The rational part of her pleaded. ‘Just say no!’
“…I…” She breathed- squirming on his desk. “I…I need to think about it. May I- use your bathroom?”
Alan sighed- getting up- and gesturing out the door.
“…To your right, first door on the left.”
Bolting upright, she left the room- slamming the door behind her.
Anna shuddered as a splash of cold water hit her face- shocking her back to reality. Shivering, she held the robe tight to herself as she sat on the lip of the tub. Her hand slid into her pocket, fishing out her phone- pulling up the contacts list- her thumb hovering over the green button to call home. Just one tap, and she’d be on her way back- and Alan Sheppard would be on the six-o’clock news. One tap, and she’d be back home, safe and sound.
Only, when she tried, she found she couldn’t do it. The feeling of the money in her hands flashed into her mind as her thumb descended- and to her shame, she couldn’t bring herself to call. Cruising down the highways in a Corvette- her Corvette! With how much money he was offering, she could totally put a down-payment on a new car- not a rental, her car!
‘But…’
She shuddered again- thinking of just what she’d have to do for that. That was a lot of money to give a hooker, and she got the feeling that meant it wouldn’t be a one-night obligation. No…he wanted her. And he was willing to throw money at her to have her. Was she really going to do that? Be at the beck and call of a man old enough to have fathered a child her age? Do…things to him? She didn’t even know how to do things! The one time she had tried to fluster a boy with a banana, she had nearly choked on the damn thing! She couldn’t- she didn’t have the ability! Unless…he didn’t care about that?
Her mind flashed to a scene she had watched- some porn that she pulled up on the family computer to help her get off. A woman, tied to the bedposts while a large, burly man pounded her pussy. Was that what he wanted? A young, nubile body…to use?
Anna gasped, shuddering in her seat as the thought sent an unexpected thrill through her body. She wasn’t- she wasn’t entertaining this, was she?
Her hand dipped between her thighs, sliding up between the folds of her pussy- blushing as they came away wet, slick with precum.
Not only was she entertaining it- it looked like her body was sold on the idea. The blush spread down to her neck, and she began to pant- rushing back over to the sink to douse her face with water again.
Looking back up at her reflection, she stared. Stared at the face that had captivated a man, at the body that had her friend’s father burning with lust. She stared at the rise and fall of her shoulders, at a bead of water trailing down between her breasts, down to her stomach…
Her knuckles gripped the edge of the sink as she breathed.
In.
Out.
Slowly.
Her breathing steadied, as she looked away from her own eyes- twisting the knob, and stepping out into the hallway. She could either walk back into the office, and accept his offer- or walk right on by, down to the laundry room. She’d nab her dry clothes, calling a ride, and that would be the end of it.
One foot padded in front of the other, quietly stepping in front of the doorway. She felt his eyes on her, roaming up and down, hungrily taking in every curve…
She looked forward- seeing the stairs to the foyer. Her grip on her robe tightened…as she fought the urge to look to her left…
Her eyes betrayed her though- as they looked at Mr. Sheppard, sitting on the desk. A gasp left her lips as she realized he had taken his cock out- slowly dragging his hand up and down the large shaft, the lust in his eyes naked as she bit her lip…
…And turned towards him, moving forward.
‘I’m sorry, Mark…’ She thought- walking in the room, and closing the door behind her- letting it fall shut with a click.
“…I want to know more.” She breathed- holding the robe tight around her- slowly approaching Mr. Sheppard.
He nodded, still rubbing himself as he nodded towards the twenty thousand on the table.
“Deal’s simple. Ten thousand for the rest of the school year- two point five kay a month- for you to be…on call to me.” He growled- sending a shudder down her spine. “Course, I won’t contact you during school, and never when you’re around Mark. Couple nights a week, at most.”
She nodded.
“And for summer?” She asked- swallowing as he grinned.
“Ten thousand…per month.” He grinned, Anna gasping in shock. “Only, I expect you to be a lot more responsive, Anna…”
She was starting to sweat. Her blush was back in full force as she gripped her robe tight. That was thirty thousand- maybe forty, depending on how long he wanted it for…
Shit. With that, she could buy a car outright, drive it around, and have enough money for several semesters at the local community college. Her will was crumbling- and Alan knew it. He began to walk towards her- letting his pants fall around his ankles, stepping out as he began to strip. Soon, the only thing left on Alan’s fit body was an open button-up- which he shrugged off- circling around to her back to rub her shoulders.
“…And…” He purred- leaning forward. “If you impress me enough…I might find work for you next summer…”
Anna went still at that, looking down at the floor as she thought. She bit her lip, wrestling with her own emotions, trying to find it in her heart to refuse…
But she didn’t.
“…I accept.” She breathed, shuddering as his grip tightened. He pulled her into him, letting her back rest against his chest. His hands slowly slid down her arms- moving forward, and cupping her breasts, dragging a gasp from her lips.
“…A wise decision. Now then…shall we seal the deal?”
She gave a shaky nod- looking back up at him- feeling her heart pound as she felt the lust burning in his brown eyes.
“…Y…es…”
With one, swift movement, he captured her lips in a kiss- moaning into her mouth.
“Mmmm…you’re just as soft as I thought you’d be~” He murmured against her…as he eagerly collected what he had paid for. He pressed his lips firmly against hers- causing her to squirm lightly in his grip, hands unsure where they should go-eventually folding in front of her as she let him have his way. Alan began to knead at her chest- panting as he relished in the softness of her bosom. Tugging away the folds of her robe, his rough hands touched her bare breast, fingers rolling her stiff nipples in his grip as he chuckled.
“Already eager?” He teased, causing her to blush.
“They…They’re still cold…” She protested, only to squeak as he pinched them.
“Uh huh.” He grinned, rolling his eyes as he kept groping her. He began to squeeze and play, taking his time and relishing in every squeak, squeal, and moan that sent Anna’s breath ghosting against his lips. Her smell was intoxicating, her moans music…
Every last bit he got from her was worth every penny he put in. And he’d have it all.
Slowly, one hand trailed down, gently tugging at the soft, plush belt of her robe. With very little effort, it slid undone, allowing it to fall open- and around her body. Anna gasped, instinctively trying to cover herself- only for Alan to gently take her wrists, and tug them away from his prize.
“Come on…it’s just us here.” He crooned- nuzzling against her. “The only person who’s here to see is the one who’s paid for it.”
Anna panted, feeling warm and dizzy as he handled her. The older man had him in her grasp, and he was strong enough to do whatever he wanted to her…
She shuddered in pleasure- and promptly surrendered. Her hands fell limp at her sides as his hands roamed her figure, fingers digging gently into her flesh. He was eager, with a frantic energy highlighting his every action- as if he were afraid she’d vanish in smoke. Eventually, however, his hands settled- his left cupping a hefty breast, and the other…
Settling between her thighs.
The first touch at her lower lips sent a thunderbolt through her spine. A squeak left her lips as her face lit up in a furious blush, melting into his finger sliding along her soaked pussy- leaning back against him as her cum began to dribble down her thighs. She had touched herself before, of course- but the feeling of a stranger’s hands sent a rush through her- igniting the need locked away within her. A chuckle hit her ears as Alan played with her- his fingers sliding deeper, deeper- coaxing higher and higher moans from the younger woman, breathing picking up in need…
Alan grinned, taking a nipple between his fingers and starting to tug- as two fingers slipped inside her. Anna’s figure went rigid briefly, as she gave a shocked gasp- but was soon fighting to stay upright, leaning heavily on him for support.
“O…Oh fuck…~!”
His smile only widened at her whispered swear. It may have been a few months since he last pleased a woman, but it was clear he hadn’t lost his touch. The fingers inside her began to gently twist- poking and prodding against her walls as he gently pumped his fingers inside. With every thrust, he seemed to find a new weakness, a new spot that made Anna squeal in the most amazing way. The younger woman was putty in his experienced hands, at the mercy of his agonizingly slow touch. She started to squirm- moving her hips so he’d probe deeper, faster- she could feel herself start to rise up, a familiar tightness in her core starting to build…but knowing he was going too slow to really get her off.
“Muh-Mister-Sheppard…” She whispered- feeling him quake briefly at the sultry purr of his name. “P…Please…faster…!”
She heard his breathing pick up- as he leaned down to whisper, teeth grazing her ear…
“Of course, my pet…”
‘Oh, FUCK!’
Anna’s wish was granted immediately- as his fingers began to pick up speed, soon becoming audible in the quiet of his office. Every time his fingers slid into her pussy, more cum seemed to gush out, soon coating her legs- and a bit of the carpet- in the stuff. She was soon relying on him to keep her upright completely- reduced to a panting mess, quivering at the sudden onslaught of pleasure, quaking with desire as she cried out…
“Ohyes! F-Fuck! YES! Gods yes! YES- YES~!”
With each ragged breath, he was spurred on- to go harder and faster, face buried in the nape of her neck as he tugged and pulled at her tits. One hand squeezed hard, the hand between her legs almost frantic, desperate to get her off…
“Yes!” She squealed- hips pumping into his hand, riding as much as her legs would allow.
“YES!” She screamed- one shaking hand of her own fanning her clit with a burning need.
“YES! YES! OH MY FUCKING GODS, YES! AAAAAAAAAAAAHHN~!”
Stars danced in her vision as she gushed- a long, tapering scream tearing its way from her throat as she coated his hand in a thick, wet layer of cum. Her shuddering figure leaned against his, quivering as she whispered a desperate, begging mantra- as he fingered her through her orgasm- only stopping when she was an overwhelmed wreck, barely able to stand.
The pair stood there for a while- Anna grinning in her post-orgasm haze, while Alan’s fingers began to lazily stroke her soaked cunt.
“Enjoy yourself, pet?” He smiled- receiving a low moan of pleasure in response.
“F…Fuck…that…” She breathed- panting as she slowly reached a hand up to mop the sweat from her brow. “I…I’m still catching my breath. You…you’re really good…at this…”
“I’ll take that as a compliment.” He laughed- humming as he leaned into her touch. “Mmmm, you were good, too.”
“R-really? I uh…haven’t really done anything…yet?” She stuttered- looking at the head perched on her shoulder- and swallowing when she saw his lusty grin.
“Hm? Well then- why don’t we change that?” He purred- as she felt him poking her thigh with his cock.
Any questions died in her throat as his arms wrapped around her- hoisting her up in the air. A shocked squeak left her as she was lifted- looking down in shock as she saw his length sandwiched between her thighs.
“Mmmf…” He grunted- grinning at her surprise. “Keep those thighs together. I need you for a bit.”
Anna nodded shakily, clenching her thighs together around him, hearing a satisfied moan from behind. After she did, he started to thrust, helping himself to a thighjob from the helpless woman.
“H-ah!” She squealed, watching him slide between her, soon slick with her cum. “M-my thighs?! Y-you’re not gonna-“
“Later.” He grunted, panting as he pumped back and forth, soaking himself in her juices. “I just need…to be a little lubed up…for the next bit…”
“T-the next-“ She began- only to be cut off by suddenly being planted back down on her feet. “W-wha-“
“On your knees.”
Any question she might have asked were silent on her lips- as she immediately, obediently, sank to the ground.
“…Holy shit.” He chuckled- circling around to the front- and bringing his cock to Anna’s face. “I wasn’t expecting that to work- not immediately, at least. That last orgasm took a bit outta your brain, didn’t it?”
Anna could only swallow in response- too transfixed to even attempt an intelligent reply. “I…I mean…it was pretty good…haven’t, uh…gods, how…how big is-?”
Alan hummed in response- as his cock twitched in need, a bead of Anna’s cum slowly dribbling slowly from its tip.
“Hmmm. Nine inches, I think? I dunno, never really measured…but nine sounds about right.” He shrugged- amused by the effect it was having on her. “What’s the matter, never seen one before?”
She jolted back- blushing as she stared at the ground.
“U…Um…well…” She stammered- suddenly feeling quite bashful. “I…I’ve never really…uh…I mean, with a dildo, sure, but…”
“…Oh, shit.” He breathed. “This is your first?”
“Well, uh…the first flesh one, yes. I mean…in person?”
He almost scoffed in disbelief. She had agreed, with very little convincing, to let herself be bought by him, and was quivering in his touch not minutes ago. And now here she was- a blushing…
“Oh hell.” He reeled- rubbing the back of his head. “Well, uh…here it is.” He said- rather lamely, compared to the smooth dominator that had been there a few moments prior. Still, it worked- Anna’s eyes moved back to his cock, swallowing as she watched it twitch in place.
“…It…it sure is.” She gulped- her throat suddenly feeling very dry. “D-did you want me to…uh…suck it?”
“…Fuck.” He whispered- blinking at how…oddly cute her hesitance was. “I mean, if you want to…but get used to it, first. Use your hands.”
She nodded- words failing her as she gently reached up, wrapping her fingers around his cock. It was warm to the touch, still slick with her cum- and seemed to get even firmer as she grasped him. Gently, she started to drag her hand back and forth, looking up at him to gauge his reaction. His half-lidded gaze met her inquisitive stare, bringing laughter to his lips…and a blush to her face.
“Use the other one too…and try to stick to the tip.”
Nodding, she took his suggestion, both hands now wrapped around his pulsing length. She slid them up and down, face on fire as Mr. Sheppard moaned openly. Her eyes darted around, noting his buckling knees, the precum dripping down the curved shaft…
She swallowed, licking her lips as she gathered her wits. She shuffled closer and closer- slowing slightly as she watched it throb in her hands…
“F-fuck, it’s been too long…” He whispered, a hand reaching down to rest on her head. “Should have finished before I called you up. I’m already about to blow.”
“A-already?” Anna whimpered- looking at his dick like it was going to spurt at any moment. “I-I haven’t been doing much…”
“It’s different when it’s someone else’s hands…and you’re too fuckin’ cute.” He breathed- smiling as she squeaked- then moaning as her grip reflexively tightened, only barely saved from making a mess through the strength of his will alone. “S-see? Like that.”
“T-thank you.” She whispered- licking her lips again, because it seemed like they were drying out fast. “Um, do you want to finish inside…or-“
The hand gripping her head suddenly went from gentle stroking to an iron grip- as the tip of his cock was lined up with her lips. Her eyes widened to the limit as she felt the heat against her mouth- reflexively opening up to gape slightly…
And that was the only opening he needed. Before she knew it, he had slid the tip inside- and his free hand replaced hers on his cock.
“I think I will.” He smiled- “Sit back and enjoy. Just get ready.”
Her hands fell to her sides as Mr. Sheppard began to stroke- much faster than she had dared, clearly desperate in his movements. Her head was kept firmly in place, wide eyes watching every pulse of his throbbing cock, slick with spit, cum, and pre- he was about to finish, and he was about to finish inside…
She tried to talk- but it only came out as a moan, which brought a gasp from the older man’s lips as her purr vibrated along his cock. He sped up further- spurred on by her attentions- however accidental. He began to gently thrust his hips- sliding an inch of his cock in and out of her, pressing it against her tongue, forcing the younger woman into a hurried, shallow blowjob…
And then…release.
Anna’s eyes couldn’t get any wider as cum flooded her waiting mouth. Alan let out a feral growl of triumph- pushing in as much as he dared while his seed poured from his cock. She soon ran out of room in her cheeks for the backed-up man’s release, cum splattering out of the seal her lips had made. She tried to swallow and make more room- but the taste was so alien on her tongue that she drew back, coughing…and he still wasn’t done. His length let a few more ropes out, draping her breasts with a pearl necklace, as the both of them fell back- Alan landing with a heavy thud as they both panted.
“Holy shit.” They both breathed- staring at one another- eyes taking in different views.
For Anna, her eyes went wandering down to his cock. She stared at the pulsing rod, slick with cum and her own spit, marveling at how Alan was still so hard. With everything he had done to her, and considering his age, she was amazed he still had fuel in the tank- but as she marveled at his firm physique, she realized that for a man that was in-shape as he was, going longer was trivial.
For Alan, going soft just wasn’t possible- not with the view he had. Anna’s front had been splattered with his cum, dribbling down her bosom in thick, pearlescent globs. Her whole body was shaking- waiting- eager! For more! And as his gaze trailed south to her splayed legs, he let a moan leave him- as he realized just what he still had to claim as a reward…as his eyes took in her soaked pussy, practically quivering for him…
With a view like that- it didn’t take him long to get back on his feet. Feral strength flooding his limbs, he hoisted her on her feet- backing her up into the room. Anna could only gasp- squealing when her ass hit his desk. He reached around her- sweeping the papers off with a broad swing of his arm, and then pushing her flat on her back.
Gods, the sight of her. Alan licked his lips hungrily- seeing the desire in her eyes, her chest covered in his cum, pussy slick with need. It was almost enough to have him dive in right then and there…
Almost. His sense hadn’t left him yet.
Plucking his shirt up off the ground, he quickly wiped his cock dry and rummaged through a drawer of supplies…withdrawing a condom.
“H-huh? Why-why do…”
“Hm?” He hummed- looking over at Anna as he tore open the package- quickly slipping the rubber on. “Wife used to get randy in the office sometimes. Pills made her bloated, so we stuck to condoms.”
“Are they still good?” She asked- leaning up a little as he came back- only to be pushed roughly onto her back again.
“Still before the expiration date. Barely. Now then. No more stalling.” He murmured- spreading her legs and making her straddle him- holding onto her thick hips. “No more foreplay. I’m gonna take what’s mine. What I’ve paid for.”
The reminder sent a shocked gasp through Anna’s frame, making her bite her lip. She settled against the desk, breathing heavily- making her cum-covered chest rise and fall in short, breathless gasps…
“Y…Yes, Mister Sheppard. J…just be gentle. I haven’t…done this with something…that’s not silicone…”
Oh, hell yes. He had paid well. First crack at her pussy before any other man had gotten to her…
With a grin, he lined up- pressing the tip of his cock against her waiting folds, making sure he was ready to slide in…
And then he thrust- slamming his hips into hers, causing Anna’s loudest scream yet.
“FUCK~!” Anna cried- knuckles white against the edge of the desk. “F-fuck- ohgods! Y-you’re big! S…So big!”
Alan, for his part, was fighting not to swoon as Anna’s tight walls clamped around him. “And y…you’re tight…!” He gasped- as the both of them adjusted to feeling the other. Neither of them were prepared for the sudden rush of pleasure, the heat that seemed to flare to life in the room as they were joined together- closer than either of them would have dared dream. The both of them were suddenly struck dumb- eyes burning as they roved over each other’s bodies-
And with a shared smile…they started.
Alan’s grip tightened around Anna’s waist as he began to thrust, pumping every last inch inside her in a quick, desperate frenzy. His hips, now slick with her cum and the lube on the condom, pounded against hers, causing a loud, rhythmic clapping to sound around them in the office. It rang in their ears, primal and resonating, dulling their senses and sending them spiraling into lust. Slowly, the world around them was reduced to just the room they occupied- and then, just the pair of them.
Alan’s eyes were aflame with lust as he watched her- watching the waves of force rippling up her curves. Watching her cum-covered breasts bounce with every thrust. Watching her face set itself in an obscene mask of pure pleasure. Her mouth was hanging open, eyes half lidded and staring straight at him, the flush on her face spreading to her neck. He felt his heart hammer even harder as he shifted his grip- now focusing on thrusting faster and faster.
Anna’s cunt grew even tighter as he carried on, her moans only punctured by the staccato of their hips meeting. Her knuckles tightened the grip she had on his desk, trying her best to stay near him as he controlled everything. Every pump inside her seemed to hit a weak spot, causing the heat inside her to start building again in that familiar way…
“M…Mister…Shepparrrd…!” She moaned- managing to slur out the words through the thick haze of lust. “I…think I’m…gunna cum- again…!”
Alan nodded jerkily- the only sign that he would give that he had heard her. Her words spurred him on, desperate to feel her walls cinching around him, to hear her screams again- and know that the woman below him had been driven wild from his frenzied actions. He hunched slightly- clenching his muscles taut as his treatment grew rougher- trying to stave off his inevitable orgasm as long as he could. His eyes closed, sweat shaking off his form, using his arms to start pulling Anna into him in time with his thrusts. He was hitting harder, faster, deeper…
And soon, it was far too much for the blushing virgin to bear. Thrashing in place, she cried out- as her next orgasm ripped through her body. Cum poured from her slick snatch, soaking the desk beneath them as her cunt gripped him tightly- the sounds of their fucking drowned out by the long, lingering scream. At the sensation of her sealing around him, some switch in Alan flipped. Rather than slow to a stop to collect himself, he kept on hammering at her hips- pounding her pussy relentlessly through her orgasm, keeping her at her lusty high- caught in a fever pitch of lust.
He relished in the sounds- hearing her screams flood his ears, feeling the tightness of her walls around him, the sound of her pussy taking his cock, the loud, echoing claps from every union of their hips. It was a bliss he hadn’t known for a while- and he’d savor every second. He huffed- leaning forward fully as he pressed his chest flush against Anna’s nubile form, rutting into her like an animal as Anna’s mind fogged. The waves of pleasure crashing into her were too much to bear- more than she had ever experienced before. Alan’s clear experience was showing through this feral lovemaking- even after succumbing to his own instincts, it all felt so good that she couldn’t stand it. Eventually, after several back-arching moments, she could bear no more.
Anna went limp- letting the strength flee her limbs as her pussy gushed around him, crying out in a long, sustained squeal of pleasure. He kept hammering her, slamming his cock in and out, heedless of the cum covering his hips, her release dribbling down his legs. She had no more energy left in her after that, but Alan had paid for her, and he was going to have her…even if that meant using her limp body like a sex doll.
The thought only made her tighter-which finally pushed Alan over the brink. Only a few short thrusts after she exhausted herself, he hilted his cock inside her- and throwing back his head with a roar, finally came inside her.
Anna was shocked into silence at the sensation- feeling a burning warmth fill her loins as cum filled the condom. Her screams died down into a long, shocked gasp of breath as the heat between them became unbearable- her wide eyes unfocused, staring up at the ceiling as her vision swam…
The both of them stayed there- Alan’s cock still throbbing in Anna’s pussy, pumping out more and more cum- as Anna twitched, too weak to do anything but take it- some feral part of her wishing that the barrier would vanish and take his seed. They remained there for a full minute while they caught their breath- before Alan finally stood up. Anna couldn’t stop the whine that left her lips as his cock slid out of her cunt, the condom slipped halfway down him, with a massive glob of his release at the tip.
Anna wasn’t ashamed to admit that she stared- something that did not escape the notice of her new owner. With a laugh, he pulled it off- lifting the rim up to her lips- and tilting it back…
This time, she swallowed everything. No order was given- and there wasn’t a need for one in the first place.
“Good girl.” He purred- sending a shudder down his figure. “You’ve picked up what I want from you quick.”
She managed a shaky laugh as she pushed herself up onto her elbows- looking up at him with an amused expression.
“W-wasn’t hard to figure out. Besides- I wanted it too.” She breathed- managing to rise to her feet- only to promptly lose her balance. Before she could so much as yelp, though, his arms wrapped around her, holding her steady as her head rested against his chest…
Sighing, she melted into the embrace, going limp in his grasp as he held her tight.
“I take it you had fun?” He said with a smile- gently rocking her as she nuzzled into his embrace.
“Mmmm.” She hummed affirmatively, managing to look up at him. “Best first time ever. It’s going to be a while before that gets topped.”
Alan laughed- and cheekily replied-
“Give me a few minutes.”
Anna couldn’t help the laugh that left her- as the pair shared in each other’s warmth, feeling the gentle heat bloom in their chests…
“Haaah…still. That was a helluva first go. I can’t imagine what next time’ll be like-“
“Next time? Oh, you think we’re done?”
A bolt of lightning couldn’t have made her straighten up faster- as she felt a familiar heat down by her thighs, and a grin crossed Mr. Sheppard’s face.
“Hate to break it to you, babe…but I paid for the whole night.”
She yelped as he scooped her up- humming a tune as he carried her out of the room, quickly crossing the distance to the master bedroom. With a grunt of exertion, he dumped her on the bed, still quivering from last time as he moved around her. Anna’s eyes widened as he pulled another box of condoms from the nightstand, fresh and unopened- tearing into the it, and pulling out a long roll of fresh, shiny packages. Ripping one open, he slid a new rubber on his hardening cock- and quickly took up a position above the teen tramp.
“I hope you’re ready, Anna- that was just the first few hours in a long line of months.” He breathed- already sliding in for the next round. Anna, for her part, could only cry out in joy as she seized fistfuls of sheets- already bracing herself for another marathon session…
That night, for the first time in a long time, Alan Sheppard’s room was filled with the sounds of a moaning woman, begging him for more- and his own howls of pleasure as he took her…
“Hey Dad! Sorry I’m late calling- phone died.”
“Oh, don’t worry about it, kid. I’m just happy to hear from you. How’re you doing?”
“Oh, doing fine. Orchestra let out a little early- I think we finally talked the director into letting us go home. I don’t think I’ll be able to make it home tonight, though. One of the cellists is letting me stay at her place. Uh, her parents are home, though, so, nothing funny is going to happen. I swear.”
“Come on, kid- I know you’re responsible. Have fun over with, ah…what was her name?”
“Uh, Sarah. Speaking of, uh, girls, um, is Anna there?”
“Hm? That girl you’re sweet on? Yeah. She’s here.”
“D-DAD!”
“Just teasing, kid- you need to lighten up.”
“Hm? Hey, Dad, are you all right? You’re breathing a little funny…”
“Oh, just got off the exercise bike. Gotta stay in shape. Did you want me to pass on a message to her?”
“Oh, uh- no. Just…just wanted to make sure she got there safe. Uh, hey- Sarah’s calling me to her car…”
“Heh. I getcha, kiddo. Have fun. Sensibly.”
“Dad…!”
“Hey, as long as you’re safe, you can do whatever you want! Just have fun, yeah? You’ll only be in high school for a few more months. Make a new memory.”
“Sure, Dad. I gotta go- love you.”
“Love you too, kiddo. See you!”
With a click, the call disconnected- the display on Alan’s cell phone going dark. Rolling his shoulders, he spared a glance backwards- smothering whatever guilt he felt with the satisfaction the view brought him. Anna, splayed on the sheets, chest heaving- tied off condoms discarded carelessly on her body. Sweat rolling down her fit figure, a massive dark spot staining the light fabrics below her pussy.
Smiling, he rolled back over her- pressing his chest against hers, staring into her eyes…burning with lust for him, and him alone.
“Hear that, Anna? We’ve got the rest of the night to ourselves.” He breathed- cupping her chin, and pressing a kiss to her lips as a low, lusty moan made them quiver…
“Now…let’s see if we can finish this box of condoms, hm?”
“Y…yes…p-please…Mister…Sheppard…”
Smiling, he reached for the box on the nightstand…ready to continue.
This was just the first time of many…and he was already aching for more.