Molly’s Obsession – Anal –


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Molly held her own gaze in the mirror, straightened up, adjusted her clothes some more, twisted left and right. The prospect loomed in her mind once more, and a short surge of adrenaline sent her heart rate up and a faint blush bloomed on her cheeks. She had every reason to think she could pretend there was nothing going on, act nonchalantly, and he’d most likely play along. It was just texts. Nobody had done anything wrong. The guilt pulsed in her stomach at that wondered: she couldn’t undo what had already been said. She had crossed a line.

She straightened up again. 19 years old, her body was soft and curvaceous, her hips the width of her shoulders, roundly framing the adorable smooth pouch of her tummy with her waist coming to a gorgeous cinch. Unclothed, her breasts would naturally swoop outwards just a little, and each would fill one of her hands. Her butt, though… she’d need four hands to grasp all of it. There was a reason she avoided jeans, and lived in gym clothes and shapeless skirts. The giant peach. Devourer of underwear.

Today, she’d dressed a little more smartly: a spruce coloured knitted t-shirt with a white Peter Pan collar, and a pair of high waisted pleated tweed shorts that actually fitted, and she loved too much to risk wearing them out. Her neck-length dark brown curls surrounded her head like a halo. Gentle green eyes, and matte pink lips. She turned her head a little and admired her jawline against the curve of her neck.

Adam would be stopping by in 15 minutes, officially to collect the last of his things. He and Molly’s mother had only dated for a month, but it had been an intensely passionate month, and the last week that he’d essentially lived there had brought with it an accumulation of possessions. It was at the beginning of that week that she’d begun to knowingly court his attention. Adam was 50, sporting the last flecks of jet-black on a head of lustrous silver hair. Tall, tanned, and square-shouldered, the sort of man her mother craved. Adam was a Senior Engineer with a solar energy business. He had money and knowledge. He was nice to her mother, and to her.

The sound of them fucking at night had made her uncomfortable at first. It wasn’t particularly graphic; the occasional moan, and the unmistakable thumping sound that she did her best to drown out with her headphones and complained about to her friends on Discord. Molly didn’t consider herself excessively sexual. She played Stardew and listened to History podcasts and read classic literature. She also got herself off as much as any young woman, and had her crushes and curiosities, but didn’t possess the pornographic inner sex life that some of her peers did.

When they’d been dating for around two weeks, Molly had been coming home from a friend’s house and had been forced to sneak past the usual din on the way to her room. She had heard their sex life in explicit detail for the first time in the form of her mother’s strained moans: “fuck my ass, Adam.”

The words shot through her with shock and panic. Words unintended for her ears; an aspect of her mother she had never been supposed to see. Darting back to her room in long, careful steps, she’d sat cross-legged on her bed, sitting with the discomfort and embarrassment. She’d tried to move past it, and, not unenlightened herself, reasoned that everyone was entitled to their private lives. She had hopped into a group channel and started her Switch. No need to give it any further wondered.

Except that she did think about it. Fuck my ass, Adam. The raw ineloquence of it. The straightest, most graphic demand, delivered in the most yearning tones. She squirmed upright on her bed, sensing her increasing wetness as the wondered she tried most to ignore intruded at every minute. Though she tried her best to dismiss it, she empathised with those enraptured tones too readily, and her anus tightened and relaxed with the fidgeting shuffle of her hips. She fixed her gaze on the screen, keeping her hands busy with the buttons, her face bright red with arousal as she refused to give in.

The next few days had been no easier. Adam was around the house at all times, warm and affable, taking a sincere interest in her life and hobbies. At the sound of his deep timbre, her pussy and ass would both clench; Molly quickly learned to perfect her poker face, the connection in her mind between this handsome middle-aged man and euphoric anal sex consolidating with every minute of small talk.

She began getting herself off more often, seeking out close-up anal penetration images, her eyes poring over every detail, every stretched membrane, the greased, glistening skin of hard cocks mid-thrust into tight, full holes. She could have marked the moment she inwardly admitted to her desires down to the second: she had closed her eyes and allowed the impression of his intoxicating smile to dominate her mind while she imagined him erupting inside her tightest hole. She came so hard that a humiliating yelp made its way past her gritted teeth, and both Adam and her mother had called up the stairs to ask if she was okay.

That last week he was there, she began to do things she knew, She KNEW she shouldn’t do. She avoided wearing underwear when he was in the house, opting for tight gym shorts and loose t-shirts. She smiled more eagerly, and gave him more eye contact. She’d slouch on the sofa more, in a way that made her curves more prominent when the three watched television. And to her forbidden delight, she caught him looking. Several times. And when she caught him looking, she’d stretch, or shift position, anything to give him a better view, to let him watch her move. Her mother didn’t seem to notice, or at least, didn’t mention it. She would cosy into Adam’s chest, apparently uninterested in her daughter’s shameless and uncharacteristic seduction.

One day, she got up early and waited in just her underwear with a cup of coffee, so that he could “accidentally” see her as he came downstairs. She had watched with glee as he turned red and did his best to keep looking at her face while she chatted idly to him, until embarrassment overwhelmed her, too, and she retreated once more to her room.

And later that very day, it ended. Her mother didn’t go into detail – “that arrogant asshole” – was the most she divulged. Molly drafted a text:

hey dude, sorry it didn’t work out, i’ll miss you round here

She laboured over the words for an hour, and left it unsent. Two days later, with two fingers of her left hand plunged deep inside her pussy and out of her mind with arousal, she said “fuck it” out loud and pressed send. The rush of the act pushed her into another surging orgasm, followed by immediate humiliating regret. As she navigated to “unsend”, one tick turned to two, and she saw he was already typing his response.

Adam: Hey, that’s really nice of you to say. I liked getting to know you a lot. It is a shame, but we’ll all live. But I’ll miss our morning talks.

She wiped her fingers on her inner thigh while she composed her follow up.

Molly: me too!! my coffee buddy

Molly: where am i going to discover a replacement

Adam: Just wear what you wore to our last coffee date and you’ll have plenty of candidates.

She held the phone a little further from her face and tried to keep her breathing steady. She knew a boundary was being crossed.

Adam: Sorry. I shouldn’t have said that. it was disrespectful.

Molly: lol no no its fine

Molly: you liked my outfit?

Adam: Isn’t it an overstatement to call it an outfit?

Molly: are you avoiding the question

Adam: It’s my favourite of all the outfits I’ve seen you wear.

Molly clenched her teeth and drew breath, fresh moisture glistening on her swollen pussy, the adrenaline of guilty pleasure surging through her.

Molly: what did you like about it?

Adam: …

Adam: Please don’t make me say, I feel like a creep already.

She moved her left hand back to her pussy, the length of her middle finger gliding back and forth across the throbbing nub of her clit.

Molly: then be one

Adam: Fine LOL

Adam: I liked looking at your body.

Molly: yeah?

Adam: I was staring at your ass when you walked away.

Molly slid a finger inside herself with an audible moist sucking sound.

Molly: yeah i know about you and asses

Adam: What do you mean?

She slouched further down fucked herself so urgently with her middle finger that she had to correct her spelling several times.

Molly: i heard you fucking her ass

She couldn’t bring herself to say “my mother”.

A week of illicit texting followed, Molly hiding her phone whenever her mother entered the room. She commiserated about the breakup while communicating relentlessly with her ex about one thing: her untouched asshole. She fucked herself whenever she was alone with her phone and his presence, and knew he must be jerking himself off as he explained to her his love of the act, his deep enthusiasm for worshipping a woman’s anus with his hands, his mouth, his cock. She’d slyly ask when she’d get to experience this; he’d reassure her that she deserved it, that the right guy would come along sooner or later. But the seal was broken on their propriety; they both knew how badly she wanted him to initiate her into this experience, both of them convincing themselves that it wasn’t real as long as it was just messages. Just talk.

It was only at the last minute that her mother had decided she’d prefer to be out of the house for the handover. Molly had assumed she could hide and save herself the indignity of being in the same house as the two of them after a week of exposing her fixation to him. But her mother had let her know that she was gonna hang out with a couple of friends all day and spare herself the annoyance of speaking to “that pompous piece of shit”. And Molly realised that she would have several hours to herself, alone with him.

She’d washed. Twice. She had studiously researched the process of preparing herself for anal sex and made sure she was as clean and clear as could be, down there. She trimmed her pubic hair into a neat and tidy patch, and, pausing several times to stop and remind herself that she and he would both probably chicken out of actually doing anything, dressed herself in the same attractive white lace underwear she’d surprised him in the kitchen with that morning. Split between reality and fantasy, dreaming about letting him enjoy her but aware that it would likely go unfulfilled; consumed with depraved guilt at the mere desire to betray her mother like this, not to mention how old he was, god, she wondered, he’s more than twice my age… this was her mindset when conducting her final outfit check in the mirror.

The doorbell rang and she was suddenly shamefully aware that she’d dressed up for a man to come and collect a few boxes.

She answered the door to see his face for the first time since that morning she’d exposed herself to him. The fact of his physical presence was a small reality check: there had been a human at the other end of that long text exchange. They exchanged bashful smiles and greetings, their sexually-charged conversations hanging in the air between them. He shut the door behind him and stood in front of her, wearing that faint smile of uncertainty.

“You look really nice.”

She smiled warmly back. “Thank you. You look handsome.”

Another pause.

“Listen,” he said. “I know… we’ve talked about some things. A lot, and… it feels so inappropriate. But I wanted to tell you to your face that it meant a lot, to connect with you like that. I hope you haven’t felt uncomfortable or pressured.”

Molly’s smile became a grin. “No, I haven’t… I’ve enjoyed it. I do know what you mean though. I’ve been thinking about you a lot.”

Adam took in the sight of her curves, her bare legs, the hopeful smile on her face, and mirrored her expression.

“How long are we alone here for?”

“A few hours” she spoke very gently. “If you want to… I’d like to…”

She trailed off, and he did exactly as she hoped. He took a step forward, their size difference imposing on her and she had to suppress the feeling of being vaguely threatened by it as he loomed, urging herself to crane her neck and meet his lips. She felt his breath hot on her face, and was intoxicated by the musk he’d cultivated during the drive over. They kissed again, and again, her excitement peaking with each wet touch of the lips, the exhilaration of their shared trespass causing her to make short, shocked moans, which he returned deeply. Her hands flattened against his chest and her fingertips scored down his ribcage, his waist, his broad, warm back. He, too, groped at her clothing, both his hands sliding down the small of her back in unison and grasping the fat of her plump buttocks through the woven texture of her shorts.

“Fuck” they both breathed in unison, and together they stifled laughter, and his tongue penetrated her mouth once more. His hands didn’t leave her ass — massaging, squeezing, groping. Supplying, amply, the attention she’d been craving from him specifically, precisely where she’d been craving it. She wiggled her hips a little, pushing back into his hands, but pushing forward with her upper body, wanting to feel as closely as feasible the hardening of his cock against her soft belly.

She pulled back to speak, and she couldn’t modulate her tone at all; it came out in a hoarse, high-pitched whisper. “You know what I want you to do” she managed. “I need it, I’m ready, please.”

She led him upstairs, by the hand, to her bedroom, and they both stole a glance into the room where she’d overheard him fucking her mother. To both of them, it felt like they shouldn’t be there. That they were somehow trespassing in a house where they were both, for now, welcome.

She kissed him again, shutting her bedroom door behind her. She had fantasized about ceremoniously presenting herself to him — offering up her backside for his indulgence. He unbuttoned her shorts and let them drop to the floor. She stepped out of them and turned, crawling up on the bed on all fours, her knees wide, her back arched a little to raise her lace-swaddled hindquarters in the air. She turned bright red again at the realisation that she was waving her ass at her mother’s ex-boyfriend, displaying herself to invite him in. She couldn’t bring herself to look behind her.

She felt him grasp the waistband of her panties and pull, peeling them down, and her blush expanded down her chest as she felt air on her ample backside. She lifted her knees in turn in order for him to thread the garment down to her ankles and off entirely, so that she knelt, hands flat on the bed, her left cheek resting on her fingers, naked from the waist down, while a grey haired 50 year-old man began to caress her round, soft cheeks, and the backs of her legs. As if he was searching for something. For a way in. Searching her skin. She felt pressure from both his thumbs, and they pulled outwards, spreading her open. Her eyes closed, she tried to imagine his point of view. Her young pussy glistening with moisture, and above it, her anus, tight, soft, and undisturbed. She had never given in to the temptation to touch herself there when masturbating. She had wanted it to be him, all him, who gave her her first taste of that particular pleasure.

She felt his breath against her anus, a steady stream of hot air that rescinded and cooled as he inhaled, before it once again blew across her hole. It quivered and tightened involuntarily. Her blush was now accompanied by a sweat of excruciating, arousing embarrassment. He was scrutinising her hole. Staring at it. She couldn’t control her own breathing; as she anticipated his first contact she inhaled and exhaled in stuttering breaths. She wanted to speak, but the tension in her body forbade it.

And then a warm, wet sensation, and she drew air in a gasp. He had smothered her hole in a breathy kiss, letting his saliva coat it. More kisses followed, slow, adoring. His grip on her buttocks tightened as he kept her spread, a dirty, grateful pleasure radiating upwards through her from his lips. She felt the wrongness of it in the pit of her stomach in a deep, shameful euphoria. Her mouth emitted moan after moan of its own accord. She didn’t move at all; she stayed perfectly still, keeping herself in position for him. She let out a deeper, longer moan, and with each smothering, spit-laden kiss against her asshole, her heart pounded with filthy joy. She was his.

She felt him press his face deeper, and she had to apply opposing force to keep from being pushed forward. He opened his mouth over her anus and she moaned at a higher, more urgent pitch as he applied his tongue. Licking at it. Sweeping, circling, wet, warm strokes. Staying still was getting more difficult now as her body began to scream for more pleasure, and she squirmed against him, wriggling her backside against his face while he hungrily chewed at her ass, his jaw moving as urgently as his tongue. She could feel how soaked she was, as the crevice between her cheeks became slick and slippery with drool. She finally managed words: “yes… yes, fuck yes… oh my god–” before succumbing to uncontrollable moans once more. She felt his tongue harden and force itself into her trembling hole, pushing it open just a little, swirling inside of her, and she screwed her eyes shut and howled with disgusted delight as her anus was penetrated for the first time.

She kept on squirming, moaning and squealing, unable to open her eyes, immersed in the pleasure of being fucked by his tongue. Her fingers clawed at the bedsheets. She imagined herself from outside her body, looking down at her spread-open ass being eaten shamelessly on her bed.

And then something made her catch her breath, and her entire body seized up with sudden tension. He had slid his middle finger inside. She couldn’t tell how deep, only that it wasn’t in all the way, and that it hurt, and felt wonderful, and ached, and felt incredible, and that as he twisted and slowly penetrated in and out, the pleasure outweighed the pain, and she craved more. She managed to relax her body, but her anus remained tight, clamped defensively around his finger, and she directed her willpower to relax it. If she broke focus, it would tighten again. She felt an unusual, tense aching emotion as she tried to steady herself and let him in. With every fresh push she felt herself tighten up again, and once again had to learn to relax, to accommodate him.

His finger filled her to the knuckle, and after a while he was able to maintain a steady thrust, with Molly consistently relaxed around him and moaning softly, her eyes still shut, but more gently, now. For the first time since they entered the room, he spoke, with a soft, caring manner.

“Let me know when you want to try two.”

“I…” she wanted to beg him for all of it, now, but she somehow knew better. “I think… okay. I will. Soon.” She continued to moan under her breath, easing her hips back into him in time with his thrusts. “Um… you could fuck me harder if you wanted.”

He accelerated to a medium rhythm, his finger sliding in and out of her ass freely with the suckling squelching sound of his drool. She howled again, punctuated with “yes yes yes” sounds, rocking backwards and forwards to accelerate his penetrations. “Yes oh my god yes, please can I have two please please please–“

He withdrew, sucked his index finger to slather it in saliva, and pressed the tips of both fingers together, re-entering her gradually. She wailed again, clamping her jaw shut, her ass once more tightening around him. “Fffffuck”. She once again directed all of her focus to relaxing her ass, panicked gasps interrupting her spoken words. “Please… keep… going…” he fucked her with the same speed as before, the deep, dirty ache shooting up through her stomach and making her feel panicked, slutty, filthy; inwardly, she was fighting the impulse that she should reject this intrusion, force him out and get away. But that conflict brought fresh euphoria, further pleasure, and by concentrating on that feeling she was able to relax herself around him, taking the thrusts of his fingers without hesitation, lurching backwards into him needily and whispering his name under her breath.

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