Ass Hysteria Ch. 01: First Case

One of the most stories fantasies of the last fifty years is that of the husband and the babysitter. Because it's an easy premise to work from, we'll start there...

1. Incognito Beauty

Ellen took a deep breath as she stood before the full length mirror on the back of her bedroom door and let the towel drop. Almost immediately her shoulders fell and a frown consumed her pretty face at her reflection.

She was only satisfied from the neck up having always thought her visage was pleasant, validated by a lifetime of compliments. Sparkling deep blue eyes above a light dusting of freckles gave way to a thin, straight nose and full, pouty lips. Even her noticeably chubby cheeks did little to detract from the image given the sheer beauty of the rest. Framing it all was her almost waist-length, jet-black hair which provided stark contrast to her pale white skin.

Disappointment kicked in as soon as her eyes moved south.

Ellen had been one of the first girls in her class to sprout breasts back in middle school. Now nineteen, she had dueling softball-sized orbs that visibly sagged although not excessively, her nipples low as a result. Her slightly rounded belly was soft and devoid of definition with minor 'love handles' on both sides but much closer to being 'baby fat' than sheer flab. Her legs were just on the heavy side also but her thighs were still shapely and ideally proportional with her body.

After a resigned sigh, she turned to inspect the side view and wrinkled her nose at the first sight of her prominent behind. Seeing the robust flesh drooping down in the same manner and mild degree of her tits made her wince as she completed the turn and looked over her shoulder. 'Just like a bowling pin' she thought to herself when she laid eyes on the wide globes of her ass in relation to her waist.

To an even greater extent then her thighs, the cheeks of Ellen's backside had an exquisite shape. This despite the excess meat and more than a few dimples of cellulite. Soft and supple, her ass bounced with a clear ripple through the flesh for a full second after she stopped moving.

With a shrug she vowed once again to start jogging if not go to the gym.

Not that her current physical condition interfered at all with attracting mates of both sexes.

The 5'4" brunette had a few erotic trysts with other girls in highschool but didn't have sex with a male until her eighteenth birthday. This had nothing to do with her own desire or attractiveness but was more a result of her innate ability to be invisible.

Shy and demure by nature with a wardrobe that was generally over sized and leaned towards a poor-man's goth, Ellen simply blended into her surroundings. In a school with over 1,500 students she was easily overlooked. After graduation, making an effort to be more social landed her in smaller groups, her gifts recognized and to her delight, exploited.

In just the past year since losing her conventional virginity she'd had sex with nine different guys, altogether unwilling to say no to any reasonable advance. From the very first second of having a cock at her disposal after years of desire, she was insatiable. Seven of her partners were young men she'd barely or hadn't known, hooking up at parties. Led away to vacant bedrooms, the petite (if pudgy) beauty willingly opened her mouth and spread her legs as often as asked.

Due to the ease of entry and her increasing proficiency, there were many repeat engagements.

The final frontier for Ellen to cover with a man was anal sex and it was all she could think about.

Oddly enough when she was with a woman she regularly requested digital penetration of her diminutive asshole. Her first partner had driven her to an absolutely shattering climax when sneaking a finger into her rosebud while 69'ing. From that point on she couldn't get enough, even making a habit of doing herself when masturbating. Her most powerful orgasms came from holding a vibrator to her clitoris with a thin six-inch dildo stuck in her ass.

To date, she was reluctant to ask any of her male suitors for her first sodomy despite a ravenous ache for the experience.

As luck would have it, experience came knocking at her backdoor...

*****

2. Red-handed Rendezvous

Ellen used to have a very steady income from babysitting jobs when she was still in highschool. After a year at the community college (and a lot of time on her knees and back) though, she was hired on at the huge Frost Shipping facility and looking after children was no longer a necessity.

Except when it came to David Jones.

She'd been tending to Jones' kids for years and was her sole remaining client because he was an executive at the plant. Ellen wasn't bold enough to call in any favors but she knew it couldn't hurt her chances of being granted one to answer his calls. After all, janitorial was a good-paying entry level position but she had aspirations far beyond that for the future.

The nineteen year-old also had a longstanding crush on the single father a full quarter century her senior.

This was the main catalyst that led to her being in the living room with the lights dimmed an hour after getting the children to sleep. Already horny when she'd arrived, seeing him had aroused her to the point of needing (rather than just wanting) release.

Choosing her location over the privacy of the bathroom for fear of not hearing the children, Ellen sat on the couch. Dropping one hand down the front of her shorts, she slobbered urgently over the middle finger of the other before it joined the first. By then she had two digits in her slippery cunt and lifting her hips, she pressed the saliva-coated finger against her anus. Aching to come and in the interest of doing it fast, she poked against the warm, pliant circle forcefully. Mildly uncomfortable without genuine lube, she kept wiggling her way in until it was to the last knuckle.

Within seconds she was bucking her hips as the three digits were driven roughly into her smoldering holes. Her eyes became mere slits as lust rolled over her, ravaging her body with rising intensity. In just a few minutes she was approaching orgasm and biting her lip to keep from crying out.

She stuffed herself deep and rocked furiously just as she noticed a shift in the shadows of the room. Freezing instantly, her eyes snapped open wide as she took in the image of Mr. Jones staring at her from the foyer. Sinking into the couch with her head spinning from a combination of utter dismay and anguished longing, Ellen absently, slowly withdrew her hands. Overcome with the sense of falling, her mind racing, she started to cry and after a pause, the older man entered the room.

Fifteen minutes later he was still holding her, as she shivered uncontrollably, tears still streaming down her face. After half an hour he adjusted his position and gently stroked her hair. This led to her taking a deep breath and looking in his direction without making eye contact. With her slumped but still, Jones took a finger and swept away the moisture from her eyes and face. Acting on impulse, he leaned down and kissed her gently, reciprocated immediately by the even more stunned young female.

Swept away with the whirlwind of emotions, Ellen cradled his cheeks in her hands, her tongue probing his mouth hungrily. The act pushed the 45 year old man over the edge; her voracity at first but the scent on her fingers still more. The flowery aroma of her pussy mixed with the bitter musk of her asshole confirmed what his eyes thought they had seen. Any restraint that he might have called on was gone at the latter.

'I've got something for that fat ass Ellen,' he thought.

Delirious at the thought of anal sex with this young woman that he'd watched evolve into the voluptuous creature in his arms caused his dick to throb. Without pausing their embrace he swept her into his arms and swung her into his lap before standing. At a brisk pace, he carried her to his bedroom, closing and locking the door behind them before they fell onto the bed.

Ellen was kicking off her sneakers as soon as her back touched the mattress and after turning the lamp on, he stripped her naked in seconds. He stood back for a second to drink in her smooth, milky skin stretched across her curvaceous figure, salivating at the sight. Meanwhile she blushed furiously fully at being exposed in the light, still parting her thighs unconsciously.

Absently at first and then frantically, he tore at his clothes, still stepping out of his slacks when he virtually leaped onto her. A hand went to each of her floppy tits, his mouth sucking one of her ultra-sensitive nipples inside. Arching her back, she bit down on her lip once more and grinded her pelvis against him, nectar pouring from her snatch into the crack of her ass.

He performed an oral pyramid of motion, kissing her, sucking her tits for a few minutes before sliding a hand over her soft belly and onto her clean shaven pussy. The fragrance of her now sopping snatch making him drunk with passion, he abruptly shuffled down. Hands prying her thighs apart he slithered his tongue deep between her yawning labia and she gasped, her torso twisting. Lapping ferociously up and down the decadent slit he eased a thumb smoothly inside her to his palm. In the same motion it was pulled out only to reappear at her anus, pushing insistently against the pliable opening.

So very close to release when her play was aborted, her longtime fantasy now being realized, Ellen started to orgasm simply from the anal contact. Feeling her body contort, flooded under the increased flow of juices, he began sucking her engorged clit while jamming his thumb inward. Past her clamping sphincter and into the humid channel, she curved her spine in ecstasy, gnawing her lip painfully to avoid screams.

The thumb was soon drilling back and forth as he resumed his up and down sweep of her pussy, flicking her clit on the upstroke while she came. Even as her orgasm faded and sensitivity set in, he continued fervently eating her out, fingering her rectum while she squirmed with delight. Several minutes later the blissful satisfaction was repeated for the buxom teen and this time unable to stand anymore, she squirmed away.

Allowing her time to recover, Jones grazed his fingers over her luscious body and then when her chest stopped heaving, he straddled her torso. Laying eyes on his stiff 7 1/2" for the first time brought a smile to the brunette's face even as she gripped the base and pulled it towards her. Lifting her head she took it between her lips and sucked the head and a few inches into her mouth.

It wasn't lost on Jones that without so much as a word shared between them that she was giving him head. He'd already witnessed her diddling both holes and had breached her rectum himself without so much as a peep. Just twenty minutes into their initial May/November tryst he had already figured out that he could use her in any way that he pleased.

Sucking cock was not Ellen's greatest skill but she did always perform with earnest effort. Bobbing her head furiously back and forth from the start she took him to her gagging point just past her uvula with each insertion. All the while, she stroked the base of his shaft, twirling her tongue around the turgid staff. Radically turned on, he started to pump against her face, forcing her to take even more of his cock. With him trying to pierce her throat, she pulled back, choking and her eyes watering from the depth that he did manage.

She sucked him off for nearly ten minutes before he groaned, cradled her ears and went stiff as a board. Jism spurted out in thick wads, splashing against her cheeks, along her tongue and spraying down her neck. The lovely teen gulped the slimy lumps down with practiced ease, not necessarily enjoying the taste or texture but relishing the act.

Laying next to each other in silence with him fondling her body, they kissed and he rolled her on to her stomach. Looking at the magnificent expanse of her behind made him lick his lips, his limp dick bouncing at the sight. Reaching over, he squeezed a handful of the satiny flesh and in seconds was stroking and caressing the plump globes. Pulling the cheeks apart, Jones leered at her pinkish-brown asshole, the symmetrical ridges sprouting from the dark center making his cock harder.

Ellen lay still, her face going crimson again as she realized what he was inspecting. Her embarrassment soon gave way to expectation as she remembered his thumb roughly driving away in her rosebud.

'Ohgod, please fuck me up the ass. I want it so bad! Please!' she thought.

Feeling a finger tip poking against her anus even as she begged to be sodomized in her head, she lifted her backside. The older man smirked at her movement of invitation, pressing against the rubbery circle. Even with the orifice moist from run-off out of her pussy, she jerked when it was pushed and he stopped.

Knowing the answer and not overly concerned if it was a negative response, Jones spoke the first words of the night.

"I'm sure neither of us want to risk the chance of you getting pregnant, so I was thinking about putting it back here. You've had anal sex before haven't you?"

"Oh yeah," she lied, "Lotsa times."

Her heart racing, she parted her legs in anticipation to clear the path.

*****

3. Generational Gape

For just a second he contemplated taking her ass dry just to see if she would stop him. Having seen how ridiculously tight the opening was, though, he wasn't sure he'd be able to and was certain it would be excruciating for her. It was one thing to use her for sex but quite another to bring her pain so he rolled off the bed.

Ellen held her exact position while he was gone, looking over her shoulder with a grateful smirk seeing him return with a tube of K-Y jelly. She had been wondering how to word a request for lubrication after the shallow probe with his finger.

'Oh thank god! Relax Ellen, he knows what he's doing.'

The small, brand new tube was exhausted in the next couple of minutes. He first applied a thick coating to his once again erect dick, smearing the goop down to the base. A heavy dollop was then squirted onto her puckering hole as he held her pudgy cheeks open with one hand. Then using the index finger of the other, he started pushing it inside the vice of her anus. So very tight, it was a process working the lube into the jaws of her sphincter and she was sighing with lust at the time expended. Jones was also affected, his glans leaking pre-cum.

Swinging his legs over her, Ellen's nerves superseded her aching desire.

"Please be gentle," she whispered.

"Of course. You're sure you've had this done to you before, right?'

"Oh yes, it's just, well, you're...big."

"I'll go very slow. I want both of us to enjoy this because I'm hoping this won't be the only time."

Grabbing a pillow, he had her raise up to set it beneath her, improving the angle. Then placing his knees just outside of her thighs, Jones held his raging boner, again spreading her cheeks until her entire crack was exposed. Centering the head against her asshole, he pushed with restrained force, listening for and looking at any reaction.

For her part, Ellen did her best to stay calm, her breathing deep and steady, a tactic she'd learned from her dildo play. Feeling his knob stretch her elastic opening wide made her gasp softly, a look of sheer elation on her face. Without pause his dick sank into her sweltering rectum, a grunt of exertion from him as he tried to clear her powerful sphincter. Slipping through, the staff slid smoothly into her slick, muggy channel in one patient stroke.

Deeper than her well used toy had ever reached and thicker to boot, was a simply ecstatic sensation for the desirable teen. She moaned with blinding delight and squirmed, bouncing lightly trying to get even more dick into her hungry ass.

Meanwhile David Jones clenched his eyes shut, the sleek heat of her behind making him dizzy with pleasure. He was still for a full minute to savor the mild ripples of suction pulling at his rod and then he began to ease back. Looking down with just the head out of sight, he watched intently as his shaft disappeared into her bowels once more. He retracted his cock immediately then and began fucking the dark-haired beauty up the ass.

Ellen responded instantly, years of practice leaving her body well prepared for this moment, as turned on as she'd ever been. She tossed her ample behind upwards with a yearning frenzy, using her forearms against the mattress for leverage. With her bucking and his drilling, their bodies were soon slamming against each other loudly, both moaning and grunting in time.

His cock hummed greasily in and out of her with increasing velocity, met sooner with each thrust by the frenzied teen. Her cheeks wobbled furiously, more as he squeezed her thighs closer, his staff now encased inside her rectum and out. The modified position collapsed her asshole just enough to make the cavern even tighter and her pleasure impossibly grew.

Lost fully in the euphoria of two fantasies (sex with Jones and her initial reaming) realized at once, Ellen climaxed without the slightest buildup. Her sphincter clamped down and flexed in rapid spasms, matching the convulsions in her pussy. The slick constriction applied to his cock as a result caused a second orgasm without warning as Jones started to ejaculate in mid-thrust. Feeling the warm strands of jizz squirting into her rectum enhanced her climax, as did his grinding every centimeter of his cock into her bowels as he did.

Pulling out as her still pulsing asshole forced the issue with him going limp, the single dad flopped onto his back. With jism leaking from her distended anus she rolled to her side and clenched the supple cheeks of her behind before excusing herself. As she released the gooey fluid in the bathroom, Ellen couldn't suppress her absolute glee, giggling with joy.

Back in the bedroom, trying in vain to cover her luscious, pudgy body, she lay down on the bed.

"Um, you said something before about wanting to do it again," she murmured to his hearty chuckle.

"Well, I was thinking long term but sure, if you want to do it again now, we can. Maybe not right this second, of course," he said, gesturing at his flaccid dick.

She reached for him instantly and started to lightly jerk him off before leaning closer and taking his greasy, pungent cock into her mouth and sucking eagerly.

'Wow, right from her ass,' he thought, 'I'm going to have so much fun with you.'

*****

Chapter 2 preview:

"Great, another big wig coming by to talk shit to us," said Greg nodding in the direction of the door.

Ellen glanced up and then did a double take as she saw David Jones enter the mailroom. She smiled sheepishly and started to blush, the puffy lips of her cunt getting moist, her anus puckering.

A week ago to the day, the corporate executive had caught her fingering herself front and back while babysitting his kids. A rapid chain of events followed that led to the beautiful teen losing her anal virginity and taking it up the ass twice more.

He greeted Greg, introducing himself and then approached the brunette and did the same as if they'd never met.

"David Jones, you are Ellen Smith correct?"

"Y-yes, I am."

"You're the young lady I was sent to find. Greg, can you manage if I steal your coworker for a little while? Good."

Standing the broom in her hands against the closest wall, she looked at Jones quizzically. Following his lead, the covert lovers went into the department supervisor's empty office in the corner and Jones locked the door behind them.

"I hope you're okay with this but I've been thinking about your ass all morning," he started, unzipping his slacks, "Well, actually since that night. I was going to see if you could come by the house after work but I can't wait that long. Would you mind dropping your pants and bending over the desk here? I've got lube."