Courtesan's Charity Work
A prostitute gives a novice nerd his first time, but he defies expectations when it comes down to the deed.
Arthur adjusted, and readjusted his bowtie. He'd fretted over the color before making the final choice on this red one. It stood out a bit too much against the white dress shirt. Not that he had the fashion sense to notice. And, Claire's services included a lot but not help dressing. He was more than a little nervous. It was, technically, a crime. Crime was something he just didn't do. Not once had he jumped a turnstile. And he had not even smoked marijuana before. And now, courting a misdemeanor.
But, the fact was, Arthur had a difficult time with girls. They were a little mean, a little scary, and they didn't exactly lust over the poindexter archetype. In his mind, why not cheat a little and get some experience using a resource other than charm? Money. And a pretty penny at that. This way, maybe he could shake off a bit of the anxiety and nerves.
He smiled to himself in the mirror, brushing back his hair and adjusting his glasses one final time. They sat a little unevenly against his canine snout, but he thought the tortoise shell frames went wonderfully with his light brown fur. And, of course, the big white patch that fell over his left eye. A prototypical border collie boy. If a little on the short side. Scrawny.
Arthur was meeting his lovely date Claire at the restaurant itself. Nothing too fancy, but nice enough for the experience. He'd seen pictures of her, of course, but he didn't recognize her at first.
Standing outside, waiting, like a hooker on the corner, was Claire. She was dressed like she'd waltzed out of the Red Light district. Her tits were practically out. The top that held her breasts had no bra underneath, of course, and slats from which her cleavage could be gawked at. A mini-shirt with similar slats exposing her hips nearly gave Arthur a nose bleed. From the car window, as he fights the steering wheel to not ram into someone else, he thought he got a peek at her panties.
The poindexter parked his car, gathered himself, and approached Claire. With a rough clearing of his throat, and his eyes unable to meet hers, he spoke. “Good evening, my lady. You are looking, er, rather comely!"
“No," Claire said with a firm, pointed hammer's force to her tone. “Do not call me your lady. First things first, the money."
He adjusted his glasses and dived into his pocket to produce an envelope. Sixteen hundred dollars for a full evening and 'sleep-over'. Lots of savings being handed over to Claire for what amounted to Arthur being able to participate in a very successful date.
The envelope was too thin. Claire knew immediately something was up. She rubbed it between her fingers, her heels clacking the pavement below impatience. “What is this?"
“It is the agreed upon stipend for your time! Nyeh, ahem. If you look inside you'll see–"
“No. I know what $1600 feels like, this ain't it."
“O-of course it is. I wouldn't cheat you of your wages. If you look inside you'll find a money order valued to that amount."
Claire felt her eyes widen, and her mind expand to new depths of naivety. Before she could even begin to broach that subject, Arthur continued.
“Originally I had intended to give you a cashier's check, but I realized that they maintain my bank account number and identifying information. Ahem, this money order is completely anonymized." The john's lips curled into a far too feline smile. Clearly pleased with himself, he pointed at the envelope. “If you look inside, you can see that I made use of a false name!"
The nerd, in his gesture, found his eyes falling upon her supple and impressive breasts. Her nipples, even at rest, prodded the fabric forward in a way that made his blood run hot. The very notion that she was all dressed up like this, for him, was dizzying.
With her face slack in disbelief and incredulity, she ran a claw across the envelope's edge, ripping it open cleanly. There it was, the agreed upon price. And the return address was made out to one Robert Steele. She felt her eyes close slowly in a single blink of pain.
Claire folded the item, stuffed it in her handbag, and grabbed Arthur's bicep. “Let's go, I'm hungry."
While side-eyeing him and doing all the talking to get them a table, Claire couldn't help but wonder if Arthur had forgotten his propeller beanie. He was dressed like a doofus. Clean and proper but, far too uptight. Her looks got them a decent table, and all she had to do was lean back and let her boob window do the convincing.
They were given a table with a hemi-circle booth. Despite being seated on opposite ends, Claire was already concocting some way to snake next to him later. Best case she got him to pop his cork under the table with a handy, and the rest of the evening would be that much easier.
“Did I say how, erm, beautiful you look? Nyehe."
Claire batted her eyes. What a killer line. “You did, but you're so charming I don't mind hearing it again." The delivery of her words came with such dryness she'd put shredded wheat to shame.
Completely unable to detect her tone, Arthur took it as a compliment. “W-why thank you! Ahem. So, what do you do? You know, for work?" He asked, nervously.
She squinted at him. Not just because of his idiotic question, but because she swore he took a peek down at some notes in his palm before asking that. “For a smart guy you aren't too perceptive."
“Ahem. Well I had thought that perhaps, you did something else–er, in addition to being a, how can I say?"
“Whore?"
“Ehm, lady of the night?"
Claire snorted a laugh, having to interrupt herself from fully enjoying that title. The waiter arrived, a fluffy ewe who stole more than an eyeful of Claire's body as he took their orders.
Arthur put in a very conservative request for his meal, but seeing as he was paying, Claire went all out. The most expensive thing that seemed appealing. It was worth it, if only for the gulp Arthur made when she did.
They were once more tossed into awkward silence when the waiter left. Arthur's eyes shiftily looked here and there as he tried to come up with something to say. The crinkle of loose leaf paper accompanied him checking down at his lap.
“What do you do for work?" Claire finally asked, done watching her client squirm like an ant under a magnifying glass.
Arthur merrily adjusted his bow tie and leapt into a proud and happy explanation of his employment as a systems administrator. He could only meet Claire's eyes for a second or two before becoming too sheepish to maintain it, but he has no issues explaining his daily duties with excruciating detail.
Claire, eyes sleepy and fluttering, propped her slack head up by the hands on her cheeks. Arthur sighed, and finally finished.
“So yeah, pretty cool huh?"
“I'm floored by the prestige of your current employment." Claire's words were muffled by her posture, leading to them being growled out with deadpan intonation.
Dinner went on much like this. Arthur blithering obliviously through Claire's sarcastic jabs, while chewing at her ear with the most inane nerdiness. The discussion of how deep and lore-filled a recent video game release was made Claire have an out of body experience. Why her John thought it was a good idea to be talking about which ending was the best outcome for the Mojave baffled her.
The meal was excellent, but adviseably light. They were going to smash genitals together later, Claire didn't want either of them to be sloshing around with food while it happened.
As dessert was ordered and they were left alone, Claire scooched closer and closer to Arthur. The collie froze up, his shoulders hiking up as if he'd gotten splashed with ice water. His glasses slid down his snout as he looked over them at her.
“What are ya doing?" He asked with a geeky chuckle.
The fox didn't reveal her plans until she was shoulder to shoulder with him. She put on her best bedroom look. Her eyes were half-lidded, lips parted just enough to reveal her wet tongue. For a virgin, like Arthur, he was drawn in entirely.
He mimicked her parted lips, his eyes were dazzled when meeting hers. “H-hey there."
“Hush. Follow my lead and shut up." She made sure to put a sultry lilt to her command, the sort of tone that makes boys like Arthur tingle. Claire slipped her right arm around his shoulder and squeezed him close. He collapsed between her chest, cuddled between her soft vixen fur and plush breasts.
Her free arm traced up and down the inner thigh of his suit pants. Arthur shivered like a cold breeze had just cut through him, nervously looking between her and the rest of the eatery.
“Relax. Focus on me."
“But we're–"
“Buh buh buh, hush." Her hand cupped and began to more vigorously brush his thigh, verging closer to her crotch. The slight bump of his zipper had steadily been expanding. And it stopped. Pretty small. Figures.
A knowing smirk came across her lips. Small, probably a quick shot. If she got the poison out here the rest of the evening might be a lot easier. Happened before that her clients couldn't manage a second round. Especially ones like this dork. So nervous he was chewing his lips.
“I'm really stiff, it's getting uncomfortable," the collie calculator hissed in a whisper.
“Could hardly tell," Claire prodded from under her breath, confident she was dealing with a dweeb dicklet.
So, with her mental estimation so small, she was certain she'd be able to hide him under the table while jerking him off. Deftly she unbuttoned his pants one handed, and tugged down his zipper.
Springing free from the lip of his boxers like a jack-in-the-box was a fat, pre-drooling virgin's dick. Long, that was her immediate thought. Long enough it almost passed the table's lip.
“What the fuck?"
Arthur murmured in worry. “O-oh no, is there something wrong with it? Is it too small?" His eyes squinted with the feeling of oncoming tears. All his worst fears come to fruition, and in public no less! The humanity!
Claire had no time to respond to him being a weenie what with the possibilities running through her head. She had seen a lot of cocks, a lot. And immediately she knew it wasn't the largest she'd seen. Not the largest she'd fucked either. But the size and shape, especially on Arthur's small and boyish frame, made it look extra juicy.
She held it by the base, and even that clutch made him coo in desire. The sweat droplets began gathering on his brow in nervousness. But Claire knew they were okay, the staff was busy busing. She'd need to double fist this thing to give it a proper handjob.
But for now, she used one. Pump-pump-pump. She tugged Arthur's dick under the table, aiming it down.
“Whh-wowsers!" He squeed.
“You were hiding this hog the whole time, you four-eyed geek?"
He looked at her past his glasses and didn't know how to reply. The cutting words and her firm handjob making his lower lip tremble. His mind was racing with that feeling. Of course he'd jerked himself off. But this was different, a completely new angle, a new grip. And it was a girl doing it! A girl with big boobs who was really hot.
It took all his will to not drool on his own shirt and fall into the deep sticky soup of the pleasure between his legs. Pre-cum spat at the table's bottom from his cocktip with the urgent warning of an orgasm arriving too soon.
“Don't you dare cum," she growled like a cheetah rushing a gazelle. She grasped the base of his cock with a tight, restricting grip.
“Yes." His voice came with rapid nodding, high pitched and breathless.
“Put that thing back in your pants, we're going to your place."
“Yh-yes ma'am!" He dizzily stuffed his sausage back in his trousers, Claire watching it the whole way. Now that it was fully hard, it had no recourse other than to expand down his thigh. The bulge it made was stupendous.
Was she wet? It almost came with a bit of surprise. She didn't need to check, but she could feel her thong sticking closer to her pussy lips with the layer of arousal gluing them together.
“Waiter!" She called, snapping rapidly.
Claire made him drive like she was holding a gun to his ribs. She needed that dork dick, and statim, as Arthur might say. He was just as eager to know what pussy actually felt like. He hadn't even the most remote conception of what it would be like between Claire's legs, but the giddy thoughts in his head made driving a lot more difficult than it had to be.
The slutwalk from his car up the stairs to his apartment was accented by his bowlegged attempt to hide his erection. She could hardly believe him, packing that anaconda and still hunched over like a dweeb.
She slapped his upper back. “Straighten up!"
And Arthur did, keys rattling as he sprung to his full, 'confident' height. The collie's apartment was clean and trim, but sparse of anything Claire found appealing. Posters of action-y video game and movie characters lined the walls. A shelf held a variety of statues both of nude or scantily clad women and heroic men. She felt like she was in a comic book shop, geek paraphilia taken to an extreme.
The contents on display's value was easily four, if not ten, times what she was extracting tonight. After leading her in, and closing the door behind them, he stood awkwardly by her side.
Claire held her handbag by its strap in both hands, waiting a moment. Then she tilted her head, realizing he was waiting on her. “Your bedroom, let's go."
“Oh right!" He snickered and scampered off, dashing with the same energy of a rat exposed by a flashlight.
She made a small prayer that he didn't have any novelty comforter. Huge meat or no she wasn't fucking him atop Spongebob's face. Her invocation was answered, nothing but a plain and deep blue.
He sat on the edge of his bed, eyes wide and starry, kicking his feet a bit. Then he gulped and composed himself. “This is the first time a girl has been in my bedroom."
“You don't say," she gave a scan to the room. The RGBs from his desktop played across the dim walls and dark ceiling. She tossed her bag over the back of his tall gamer chair and wasted no time in slipping her top off.
Up and over her head she pulled it. Nonchalant and unimpressive to her, but for Arthur, a life goal. He leaned forward so far his glasses nearly fell from his nose, quickly pushing them back on as to not blur his ogling of her breasts.
With all the joyful anticipation of waiting for the New Year's ball dropping, Arthur committed to memory the bounce of Claire's tits finally being free from their bondage. The fabric had concealed precious little, but even so, seeing those delicately pink nipples be liberated sent him soaring.
His tail swiped across the comforter rapidly as she shook free her hair and threw aside the top finally. With a bounce of her chest and groping of her underboob, so too came a smile. There was something endearing about just how novice Arthur was, she had to admit.
When he got himself together, he mimicked her action. She did help him along with an expressive gesture. He undid his bow tie and shirt with haphazard and nervous abandon, as well as unbuttoning his pants. “It was getting a little too tight."
His form was scrawny and his fur soft, not a single mark of hard labor. When her stern gaze didn't object to his pants being unbuttoned, he weaseled out of them entirely. Past his knees and paws they went, his big dick slipping out of one of his boxers' legs. But, he looked all the more relieved that he wasn't being squeezed by his trousers.
“Well, you showed me yours. Now I've got to show you mine, isn't that how it goes?" She offered, just a hint of sultry desire mixing into her otherwise aloof tone.
Arthur licked at his lips unconsciously as the molly fox bent forward to conceal her action. Her hands went to her hips, fingers slipping past the waist of both her skirt and undergarments. Her john got a full view of her hanging chest as she did, but the rest of her goods were concealed.
He felt a great need rise in his bosom when he saw and heard her skirt and panties drop. It was really happening! A girl, naked in his room! And they were going to have sex. He nearly felt like he was going to have a heart attack.
Taking it slow, Claire stood back up to her full posture after stepping out of her skirt. Nothing but gloves and her heels adorned her now, and Arthur got a full and plain look at her pussy.
Although he trembled with anticipation the manner in which he bent forward to examine her made Claire snicker. He clasped at the rim of his specs and blinked at her snatch like a historian examining an ancient text. Clearly something about this translation was mind bending.
“Gee," he whispered. His snout flexed a few twitches as he sniffed at her, getting his muzzle closer between her thighs. He was just about to brush his tongue across her blonde fur and exposed labia when she pushed his face aside.
“Hold your horses. I'm not even out of my heels yet."
“W-w-well you don't have to. You could wear your heels, it'd be alright. Just so long as you don't step on me, or on the bed sheets. They might rip I suppose but–" he rambled, blustery with the need to talk his nerves to calmness.
“Then they'll stay." Claire didn't keep her gloves on though, quickly stripping those and revealing the natural ochre of her fur glove markings.
Her next maneuver was a grave mistake, but hindsight is twenty-twenty. She mounted the bed, crawling across it and captivating Arthur's attention. He twisted his neck as far as it would go when his body reminded him he wasn't an owl. All to follow the feminine, sensual prowl onto his bed.
Claire had lured plenty of men to arousal with this simple gesture. Her back arched just enough to make her ass really pop, her tail swishing a bit to brush against her target's shoulder. But on Arthur, it was like using dynamite to fish. It just wasn't sporting. By the time she'd rolled on his back, resting her head on her hand and spreading her legs open to invite him in, the nerd looked like he was going to have a nosebleed or go comatose.
“Well, get those underoos off and get to it, I'll guide you in. Don't worry."
“Right-o!"
Arthur nearly tripped out of his underwear and, falling snout first onto the bed as he got the final bit of fabric over his paws. Claire had to just roll her eyes up to the ceiling and wait as he goofballed himself between her legs.
Pressing between her thighs, grinding against her wet and waiting lips, he couldn't help himself from moving his hips urgently. "Golly!" He gasped, mind spazzed with the feeling and look of his dick against her pussy. Another person's warmth, for the first time, together with his own. It was soul soothing in a way, a great sigh of relief came over him. And a fierce need to orgasm.
"Okay, just follow my lead and take it slow now, alright?" Claire instructed, like a professor to a student. He surely did well at school, maybe he could take orders this way too.
She couldn't help but be a little dazzled when handling his shaft. She grasped him around the middle point, spreading her labia with her other hand to make this as easy as possible. Earlier in the night she was thinking she'd have to use tweezers. Now she was wondering if she'd actually get to cum. With his size came heft, naturally, and the weight of it as he brushed against her box had a smirk daring to cross her lips.
Arthur finally got it in. Guided by the hooker he bought and his own base instincts, he thrust himself forward into her. Fireworks! The feeling was unlike anything else he'd experienced so far. The pressure of her form clasping his shaft, the sense of her spreading around him as he penetrated further. And she seemed bottomless! He thrust forward until he was flush against her thighs.
"Wow, geez, woof, ghh!" He sputtered, batting his eyes.
"Easy, just take it easy and go slow."
"Oh sure, right yep!" Arthur's breathless blustering told her it was all in one ear and out the other.
And his action's proved it. With a maddened, feral and irregular pace the inexperienced lad began humping at her. Claire gasped and grunted, flashes of pleasure spiking from the pure brute force of his inordinately large dick. But his technique was trash! The nerdy collie had no risk of slipping out with his size, but he couldn't find a pace aside from the one his own ecstasy demanded of him.
For him, it felt like a straight hour of sex. Back in reality a solid thirty seconds had passed before he was shouting, "Cumming!" And emptying his marbles.
Claire groaned, throwing her head back at the pillow and covering her eyes with her hands. Arthur's head floated off into space as the divine, extraordinary pleasure of fulfilling the ultimate biological demand coursed through him. He couldn't go back to his hand, no way! Not after that.
"Oh my fucking god," Claire whispered to herself. Those fantasies of a decent fuck dashed on the rocks.
Arthur fell to her side, withdrawing himself and laying flat on his back. His chest rose and fell with panting, gasping for air. "Did you finish?" He asked innocently and excitedly. "That was so awesome! I can't believe that's like the real thing and all that stuff. Wow. Nothing like a warm watermelon."
She spread her fingers and shot him a dagger-filled look upon hearing that. Her desire to confirm her suspicions made her look between his legs. Cum-slick and sloppy, there was his dick. But not deflated like a balloon. Twitchy, hard and excited. That was his first time, the blood was probably pumping ferociously in him. Could he manage another? His fat hog sagged slightly like a willow under its own impressive size.
Wasting no time, Claire sprung into action.
"W-what are you doing?"
"Shut," she said, squatting over him with her heels.
Her seed-dripping honeypot oozing his cum back down on his shaft.
"Ah, sensitive!" He cried in protest, as she stroked his meat a few times and aimed it up. He didn't know how to use this fucklog, but she did. She'd ridden enough men to know just how she liked it.
Arthur hissed sharply, the feeling of overstimulation getting to him. But he was in no position or mind to tell her to stop! A hot vixen was trying to fuck him. He wouldn't pass up on round two. He moaned like the air was being drawn from him as she hilted herself entirely down on him. The weight of her was padded serenely by her plump ass.
Claire leaned down, pressing her chest to his, nearly getting completely parallel with the dork. "Brace yourself," she whispered. "You may want to hold onto something."
Taking her advice to heart, he wrapped her up in a far too gentle and innocent hug for what she was about to do. They were nearly cheek to cheek. It was almost sensual.
But Claire broke that illusion nearly immediately when she jackhammered her cunt down on him. All her force and strength went to her hips and thighs, forcing him to bone her directly and evenly. A rapid but even and skilled pace had the two knocking nethers together unlike anything Arthur could muster.
"Holy crackers!"
His body answered her call, face twisting in pleasure, trying to thrust up at her. His feeble attempts at replying were battered down by her butt. Wet, sloppy plapping filled the walls of his bedroom. A sound that had never been produced here rang out, the breathy moans of a woman in pleasure. The bed sheets soaked with the evidence of their colliding, as did their thighs.
Claire and Arthur became ragged as she continued. Soreness set into her hips as she felt his long dick plunge her depths, dragging itself across her snuggly welcoming slot. She clutched at his shoulders, and in a moment of unprofessionalism, kissed him.
Arthur's little 'mmpff' didn't stop her, but it was hardly a complaint. The vulpine's hair lay across the sides of his cheeks, curtaining him from the world as his lips pressed to hers, and his tongue naively searched for a partner. Down below something far more naughty continued. But up top, the signals of pleasure, togetherness, warmth, all mingled for the nerd.
He felt like he could die happy just then. Glasses askew, fur dripping sweat, the air heavy with the scent of their sex and oh-so salaciously fulfilled.
Claire broke their kiss and nearly howled, having been pounding his dick against her cervix for lord knows how long. An orgasm had finally been reached. She banged out the last few strokes needed, pushing herself over the edge by riding him like a stiff and warm dildo. Growling, shuddering exultations of her dopamine release were delivered through shuttered teeth.
Arthur was stunned to silence by the feeling and sight of her twitching and cumming on him. His dick flush with the cyprine reward of her ejaculation. Mixed with the cum from his previous fuck and the pre-jizz of this one, he felt his own orgasm - despite the immense pleasure - surprisingly distant.
Claireslowed, and now it was her with the greenhorn lack of coordination. Her plapping down never reached a halt, but fatigue had really set in. But she wasn't quite done. She couldn't force a simultaneous orgasm, but for all his hard work laying there, Arthur deserved another.
She wrapped her arm around his neck, and lay the other with his - clasping their hands together. "You're going to cum for me." She whispered to his ear, licking across the edge of it.
The thought seemed impossible a second ago, but that diabolically seductive tone, coming from such a lusty vixen, got Arthur where he needed to be very quickly. He gave himself over to it all, letting her take him away and before he knew it an edge demanded an orgasm and he was spurting inside her again. The load was lesser, but the pleasure was just as mind-blowing.
He had a nap, she had a cigarette. And she looked over his cashier's check with an amused look of incredulity. She'd leave it on his nightstand with a note to bring cash next time. She expected he'd call next week, hoped he did. A few more times maybe she could whip him up into something useful. He certainly had the size and stamina for it.