Eager to Please Ch. 03

Disclaimer: This is a work of fiction. All characters are 18+

Chapter 3

THREE MONTHS AGO

The wine was cheap, and the company was good. Debbie kicked her feet up on Donna's leather ottoman, feeling the tension of the week drain out of her shoulders.

"I swear," Debbie laughed, swirling her glass, "if Mr. Henderson asks me to stay late one more time, I'm going to scream."

"Just tell him to fuck off," Donna suggested, grinning over her own glass. "Or I will. These rich old men think they own the world."

"Easy for you to say. You actually own things."

"Thats because I stopped letting men tell me what I couldn't do." Donna stood, moving to the window to adjust the curtains. The motion was casual, but Debbie noticed her friend pause, gaze lingering outside.

"What are you looking at?" Debbie asked, raising an eyebrow.

"Nothing." Donna turned back, smile easy. "Just noticed Oliver trying to reach the gutters. Poor thing, he's stretching so hard."

Debbie joined her at the window, watching her son bounce on his toes, rake in hand, still several inches short of the lowest leaves. Even at his age, he barely reached Debbie's chin, slight and narrow-shouldered.

"He's small for his age," Debbie sighed, familiar worry creeping in. "He probably would have another growth spurt, at least; that's what he keeps telling people"

"He's perfect," Donna said softly. "Delicate. Like you."

"Delicate," Debbie snorted. "Boys don't want to be delicate."

"They should." Donna's eyes tracked Oliver as he gave up on the gutters and moved to weeding instead, kneeling in the grass, arms barely filling his sleeves. "He's got such soft skin. Freckles like cinnamon."

"You're weird," Debbie laughed, bumping her friend's shoulder. "Most people don't notice that kind of stuff."

"I notice everything." Donna turned from the window, refilling both glasses. "You know, I could use some help around here. Light stuff -- organizing the garage, sorting files, walking the dog. Pay him proper. Lord knows Megan wouldn't do it."

"Donna, you don't have to--"

"I want to." Donna's hand covered Debbie's on the couch cushion, warm and firm. "You're my best friend, Deb. I see you killing yourself to give him everything. Let me help. Let me give him a place where he feels... capable."

Debbie let out a genuine smile, full of appreciation. "You're too good to us."

"That's what friends are for." Donna squeezed her hand, then let go, her eyes drifting back to the window where Oliver was still kneeling in the grass, small and unguarded, the afternoon sun turning his hair golden. "I'll take good care of him," she said softly. "I promise."

"I know you will," Debbie said, blind with gratitude, raising her glass. "To friendship."

"To friendship," Donna echoed, clinking against hers, her smile not quite reaching her eyes.

THE PRESENT

The clashing of music, sound effects, and mashing of buttons was soothing in a manner Oliver couldn't explain. The Arcade was like a second home for him, a place to relax, but also where to prove he was better than others, which didn't happen as often as he'd like.

It was a day like any other, surrounded by a wall of digital noise and flashing lights that the blond could lose himself in. But today was a bit different; it felt a little hollow. As he went in on a machine, frantically tapping on the controls, he's mind would always wonder to Donna's kitchen, the cold tiles on his knees, the scent of her perfume and sweat, her hands in his hair, pressing his head deeper into her hairy-.

"Yo, Oliver"

His friend, Aaron, said, bringing him out of his trance. "You alright? You're kinda ass today."

Oliver, coming back to Earth, stared as his character lay on the ground in defeat. Aaron was right; he had been on a generational losing streak today, but only he knew why.

"Uh, hello? It could be that I'm just that good," Chester, Oliver's other friend, uttered while pushing out his chest.

His declaration was met with silence. Aaron and Oliver just stared blankly at him before turning back to each other, leaving Chester's boast hanging in the air unanswered.

"Fuck you guys"

The three boys shared a laugh as Aaron placed a hand on Oliver's shoulder

"But seriously, what's got you so distracted?"

"It's nothing really-"

"I bet it's that girl, Megan." Chester interrupted. "Man, she's hot. But isn't she like your cousin or something?"

"Dude, Shut up!" Oliver retorted, almost blushing. "And she's not my cousin. Our moms are just really close"

"Oh, in any case, she's mad pretty but like super mean"

"Dude, she's mean to you because you're an ass," said Aaron, hands looking for coins in his pockets. "Just like the other girls"

"Hey, I am what I like," Chester claimed with a satisfied smile. "And at least I can actually talk to girls"

Both Aaron and Oliver deflated at his comment, opting to continue the game as Chester chuckled in victory. The three stayed at the Arcade for another 30 minutes before Oliver decided to call it a day.

"Later, guys," he mumbled, grabbing his small bag and pushing out into the cool afternoon air. The city was a blur of motion, but he felt adrift, untethered. He walked without a real destination, hands shoved in his pockets, replaying the events with his landlady over and over again in his head, the guilt he felt from keeping it from his mother and Megan, his not-so-secret crush. The shame was a physical weight, but so was the thrill, a terrifying, hidden current pulling him under.

He was so lost in thought he almost walked right past them. "Yo, little dude, watch where you're going!"

Oliver froze, his head snapping up. Megan. Her fiery red hair was pulled back in a messy ponytail, and she was grinning that same sharp, knowing grin. Beside her, looking effortlessly elegant in a simple cream-colored blouse and dark slacks, was Donna.

"Oh! Uh, hey," Oliver stammered, his face flushing instantly. He couldn't meet Donna's eyes, his sight always slightly to the side.

Megan looked at Oliver's blushing form, up and down, smiling ear to ear. "Hmm, what's got you turning red? See something you like?"

In her teasing nature, the redhead leaned down to meet his face, almost invading his personal space as she lightly tugged at the low collar of her top, slightly exposing her cleavage.

The boy almost jumped out of his skin as he tried to put some distance between them. He turned his now crimson face away but not before getting a glimpse of a mole located on the swell of her left breast.

"Now, now, Megan. That's enough," Donna chided gently at her giggling daughter, but her eyes were on Oliver, a warm, heavy gaze that made his skin prickle.

"I'm just joshing," Megan said, raising both hands. "He's reactions are just too good, can't help it."

'Oh, how right you are,' Donna thought to herself as she turned to face Oliver. "It's good to see you, Oliver. You're out and about."

"Yeah, I was just taking a walk," The freckled boy said, scratching his cheek, still evading her gaze. "What are you two up to?"

"We're on a mission of great importance," Megan declared dramatically, hefting a couple of designer shopping bags. "Mom's trying to single-handedly keep the mall in business. Here's an idea. Why don't you help carry stuff? Come on."

It wasn't really a question. Before he knew it, Oliver was trailing behind them, his arms soon laden with boxes and bags bearing logos of expensive brands he only knew from window displays. He felt like a pack mule, but when Donna's hand would occasionally "accidentally" brush against his as she adjusted the bags, a jolt would shoot through him, making the burden feel a little lighter.

Their last stop was a high-end electronics store. While Megan debated between two different phone cases, Donna guided Oliver toward the gaming section. She stopped in front of a display for the latest gaming headset, a sleek piece of tech he'd only ever seen in magazines.

"Your mom had mentioned you were into this stuff," Donna said casually, her voice low. "This one's supposed to be one of the best. Complete immersion."

Oliver just stared, his mouth slightly agape. The price tag was more than his mom made in two weeks. "Wow. Yeah, that's... really something."

Without another word, Donna flagged down a salesperson. "We'll take this one," she said, tapping the glass case. The transaction was quick, impersonal. Donna didn't even blink at the total. She just took the sleek box and handed it to Oliver.

His arms trembled under the weight. "Mrs. Donna... I can't... This is too much."

"Nonsense. I want to," she said, her smile softening. "Consider it a little something for being such a reliable young man." She leaned in close, her lips brushing against his ear, her voice dropping to a sultry whisper that made his whole body tense. "And a down payment for what comes next. I think you'll... really enjoy it. I know I will."

The walk to Donna's house was a blur. The box felt like a beacon, broadcasting his secret sin to every passerby. As they got into the house, Megan, saying a few words of appreciation at no one in particular, went straight to her room, leaving the duty of putting away the bags to Oliver.

Both Donna and Oliver shared a look with an exhausted smile. Not being totally surprised at the redhead's antics. The more they worked in silence, the more the sexual tension grew. At that point, he begged internally for any distraction at all.

Just then, Megan popped back out, cutting the tension. She was wearing more comfortable clothes, holding up a case as she grinned at Oliver.

"Yo, Oliver. Check it out," She said as she wagged the game case side to side. "Lookie what I have."

The blond's eyes nearly shot out of their sockets as he recognized the title. "Is- Is that the new 'Avenue Combatants'?"

"That's right. So what do you say? Wanna get beaten by girl?"

"Heh, you wish" Oliver grinned. "But as much as I would LOVE to destroy you, its getting pretty late. I really should-"

"Why not stay over tonight?" Donna suddenly interjected. "I don't mind, and I'm sure Debbie won't either."

"Really, is it okay?"

"Sure, I'll call your Mom to let her know." Donna pulled out her phone, internally smiling. She loved it when a plan came together perfectly.

-

Debbie sat on her couch, the apartment was quiet. She hated that, she hated that the silence made her thoughts go places, places that she tried not to go to. Hoping to drown the silence, she switched on the TV to watch one of her shows, to keep her mind from wandering to places it shouldn't. It wouldn't be long before Oliver came back anyway.

When the phone rang, the shrill sound made her jump. The screen flashed with Donna's name, and Debbie's breath caught. For a wild second, she considered letting it go to voicemail, letting the machine be the barrier between them. But her thumb, traitorous and desperate, swiped to accept.

"Hey, Deb," Donna's voice came through, bright and breezy, as if she had never sent a video that had shattered Debbie's world. "Hope this isn't a bad time."

Debbie's throat was tight. "No," she managed, as she adjusted herself in her seat. "What's up?"

"I was calling to ask your permission. Oliver's over here, and Megan just dug out a new game he's been wanting to try. I was thinking it'd be nice for him to stay over, give them a chance to hang out. He's been such a huge help today, he deserves a bit of fun."

Stay over. The words hit Debbie like a physical blow. Her son, under her roof. All night. The image of him on his knees flashed behind her eyes, so vivid she almost moaned.

"I don't know, Donna," she said, her voice strained.

"Oh, come on," Donna coaxed, and Debbie could hear the smile in her voice. "When was the last time those two hung out? Besides..." Donna's voice dropped, becoming a husky, intimate whisper that slid right under Debbie's defenses. "... I'll make sure he's very well taken care of. I promise."

The promise was a threat. It was a key turning in a lock, opening a door to a room Debbie knew she shouldn't enter but desperately wanted to. A low, throbbing ache started between her legs, a treacherous response to her best friend's predatory tone.

"Okay," she whispered, the word a surrender. "Fine. But he'd better call me in the morning."

"Of course," Donna purred. "You know, Deb... he's such a sweet boy. A woman could get the urge to 'swallow' him up whole, having a boy like that around the house."

"Donna," Debbie breathed, the name a warning and a plea. Her free hand drifted to her stomach, pressing down against the building heat. She hated how her body was responding, how her mind was supplying the images to go with Donna's words.

"Just teasing, Deb," Donna chuckled, a low, triumphant sound that vibrated through the phone. "Alright, talk to you later."

The line went dead.

Debbie sat frozen, the phone still pressed to her ear. She slowly lowered it, her hand shaking. She was wet. Again. Just from a phone call. The shame was suffocating, but it was tangled with a dark, sickening thrill.

-

An hour later, the sounds of punching and kicking from the TV filled Megan's bedroom. "Ha! Take that, you little mushroom-top!" Megan yelled, her character landing a final, devastating combo on Oliver's.

"Aw, man!" Oliver groaned, tossing his controller onto the bed. "How are you already this good? The game just came out."

"That's a secret, dude," Megan grinned, stretching her arms over her head. "Best two out of three?"

Oliver was just about to agree when his phone buzzed on the floor beside him. He glanced down. A text from an unknown number, but he knew exactly who it was.

"Bathroom. Now."

A jolt of electricity shot through him. His mouth went dry. It wasn't a suggestion; it was a command, pure and simple.

"Uh, actually," he said, standing up a little too quickly. "I gotta... you know. Take a leak."

"Oh, alright," Megan remarked, picking her phone up. "Hurry back, I'm on fire tonight."

He forced a weak smile, his legs feeling heavy as he walked down the hall, away from the bedroom. The bathroom door was slightly ajar. He pushed it open and stepped inside, closing it softly behind him.

The click of the lock echoed in the small, tiled room.

He didn't even have time to turn before he was grabbed, spun around, and pressed hard against the door. Donna was on him, her body flush against his, one hand gripping his shoulder while the other fisted in his hair. Her eyes were dark, burning with a predatory hunger that made his blood run cold and his cock ache.

The black-haired woman was donned in her silk nightwear. Shorts that stopped at her upper thighs, hugged her form, leaving little space. Her button-up short-sleeved shirt that was a size too small.

"You really shouldn't keep me waiting," she growled, her voice a low, dangerous rumble. Her lips crashed against his, a bruising, possessive kiss that stole the air from his lungs. This wasn't like last time; there was no pretense of gentleness, only raw, urgent need. Her tongue forced its way into his mouth, claiming him, tasting him. He was trapped, the hard wood of the door at his back and the soft, unyielding weight of Donna at his front.

This wasn't anything like his first kiss a year ago; kisses were supposed to be soft and gentle. This was feral and violent. He had no idea he could lose to just a tongue; the way the muscle explored every corner of his mouth and threatened to go down his throat made his brain melt.

Separating only for a few seconds to catch their breath, strands of saliva bridging their mouths together before colliding again. She couldn't believe how good he tasted; the way his innocent tongue tried to fight back only spurred her more.

Donna's pussy had been crying for attention for a while now, forcing her to move things along. They separated finally with an audible 'pop' as they panted for air. She wordlessly guided the blond over to sit on the WC. She turned around, making sure to wiggle her huge ass, inches from his face.

"Take them off." She commanded, peering back at him.

"Yes, Ma'am." was all Oliver managed before pulling down her shorts, exposing her naked ass-cheeks, bouncing from the sudden movement. Her glistening wetness already running down her inner thighs.

Donna then bent over, exposing more of her wet cunt, along with her brown starfish. The sight was enough to make Oliver salivate with hunger.

Without warning, the boy dove face first as he began lapping at her slit, nose hitting her plump asshole. His hands gripped her thighs for leverage as he pulled himself deeper into her. Inhaling her fumes only spurred his tongue faster. He was getting high off her every scent.

The sensation of his nose and tongue was almost too much. Donna's legs weakened as the pleasure built up; she reached out to hold the towel rack for support while her other hand went to her mouth, trying to stifle her loud moans.

The world had narrowed to the taste of her, the scent of her, the overwhelming need to please. Oliver's own cock was a throbbing, straining against the material of his shorts. With one hand still gripping Donna's thigh, he scrambled to push down the hem, freeing himself. The relief was immediate, a sharp gasp muffled against her flesh as he began to stroke himself in tune with the lapping of his tongue.

He could feel Donna's legs quaking, her body tensing like a woman possessed. Her hand strained as she gripped the towel rack, her other hand pressed harder against her mouth. Her muffled moans grew higher, more desperate, until they finally broke through in a choked cry as her whole body convulsed. Her thighs clamped together as she went cross-eyed in satisfaction. A fresh wave of her slick heat coated his face.

The sight and sound of her orgasm was his undoing. With a muffled groan, Oliver's own climax tore through him, spilling over his fist and onto the tiled floor. He slumped against her, his face still buried in her tanned ass, both of them panting in the steamy, sex-filled air.

For a moment, they stayed like that, both trying to catch their breath. Oliver suddenly perked up, remembering he had someone waiting for him, probably getting madder by the second.

"You should go," Donna commanded, her voice husky but firm as she pushed herself upright. She pulled up her shorts, not bothering to look at him. "Before she comes looking for you."

She watched as Oliver scrambled to get dressed and wash her cum off his face. He mumbled a 'bye' under his breath as he left the bathroom. Poor little Olie, the night was just beginning.

-

"Took you long enough," Megan grumbled as Oliver entered the room, not looking away from the screen. "You fall in?"

"N-no, just... felt a little sick," Oliver mumbled, sinking back onto the floor pillow. He kept his head down, hoping the dim light would hide his flushed face.

The redhead paused the game, turning to look at him. Her eyebrow raised. "Dude, you look wrecked." Her eyes narrowed, scanning his face. Then, her gaze snagged on something just above his lip. A single, dark, curly hair.

"Uhh?," she said, donning a look of slight disgust. "Is that a... pube... on your face?"

Oliver's blood ran cold. His hand flew to his mouth, frantically wiping the spot. His mind raced, searching for an excuse, any excuse. "I-It must have gotten on my face when I bent down to grab something in the bathroom," he blurted out.

Megan stared at him, her expression a mixture of revulsion and confusion. She knew he was lying, but the truth would be even more ridiculous. The only dark-haired person in the house was her mom. Something about his frantic, pathetic energy made her let it go. She shook her head, a small, disbelieving laugh escaping her. "You are so weird, Olie."

She turned back to the game, seemingly ready to move on. Oliver let out a silent breath of relief. But as he picked up his controller, she shot him another sideways glance. She didn't know what had happened in that bathroom, but she knew something had. He smelled different. It made her feel... funny. A little confused, a little curious, and a little annoyed. She didn't know why, but she suddenly saw the freckled, blushing boy in a new, and stranger, light.

-

The night went on as the energy began to die. Megan had passed out on the bed, leaving the blond fully awake, as he recollected what happened earlier. The door suddenly creaked open. Donna stood menacingly at the entrance, half obstructed by the door.

"Follow me"

Oliver slowly stood up to obey, already having an idea of what she wanted from him so late at night. He spared one last look at Megan's sleeping form, knowing he would be different the next time he saw her.

-

Debbie roamed around the empty apartment, doing what could only be considered 'busy work'. The absence of Oliver made the space feel larger than it was. She tried to make it a normal night. The brunette poured herself a glass of wine and settled onto the couch with a book she had been meaning to go back to.

'Megan is there. Megan is right there in the house with them. There's no way anything could happen.' She thought to herself.

And she almost believed it. Her shoulders began slumping down. The wine was doing its work, blurring the memories of that video, and her own traitorous arousal.

Then her phone dinged. A text

Donna: Hey Deb, you up?

Debbie's thumb hovered. She could ignore it. She could pretend to be asleep, let the phone go dark, and get back to her relaxing night.

Debbie: Yeah. Just relaxing. Everything alright?

Donna: Guess who's in my room right now?

The wine turned sour in her stomach. Her hand trembled, thumb hovering over the keyboard. She didn't need to guess, but wanted so desperately to be wrong. Knowing the layout of Donna's house, she knew her room wasn't close to Megan's room.

She was lost in thought when another text came in.

Donna: He really likes it when I'm rough with him.

Debbie's hand flew to her mouth, fingers pressing against her lips. She read the text over and over again, not still believing how direct Donna was being. She should do something other than sit here with her heart hammering against her ribs and heat pooling low in her stomach.

Debbie: You're lying.

The silence stretched--thirty seconds, a minute, two. Debbie stared at the screen, her breathing shallow as her free hand drifted to press against her thigh through her leggings. Her denial was more like a plea; she knew Donna wasn't lying.

Her arousal took over before her conscience could stop it.

Debbie:... show me.

More silence. Debbie watched the three dots come and go, her mouth dry, her whole body rocked with anticipation.

Donna: Say please.

Debbie made a sound--half sob, half moan. She shouldn't. This was her son. Her baby. And Donna--Donna wanted her to plead for it? To watch as she claims him?

Her fingers trembled as she typed.

Debbie: Please

She hit send. The humiliation was immediate and absolute. She had begged her best friend to show her son being taken.

Not long after, a video was sent. With a mix of dread and carnal anticipation, she tapped on it.

Donna's face filled the frame, her eyes looking directly into the lens with a triumphant, predatory gleam. And Oliver--God, Oliver, his head thrown back, his mouth covered by one hand, his other pushing against Donna's shoulders with little strength, almost begging not to be devoured. The motion was violent, possessive. Donna wasn't making love to him; she was consuming him, demonstrating ownership with every rough movement, her throat working around him while Oliver shuddered above her.

Debbie kept watching it. She bit her lips hard, hoping the pain would keep her arousal from exploding. Her hand pushed desperately beneath her waistband. She was soaked--embarrassingly, horrifyingly soaked. Her hand peppering her wet panties.

Another text came.

Donna: Want more?

At this point, Debbie watched as her body acted on its own. She saw herself reply to Donna, shedding all hesitation.

Debbie: Please, more.

The phone felt heavy in Debbie's hand, the screen still glowing with her pathetic plea. She'd sent it. She'd begged for more evidence of her own son's corruption, and she couldn't take it back.

Another video loaded with a soft ping.

POV shot. Donna's perspective looking down. The frame was dominated by Donna's own sweaty body, her hips spread wide, and beneath her--Oliver. Debbie's son lay sprawled on that massive king-size bed, his face buried between Donna's thighs, his eyes glazed over, seeking approval as he worked desperately. She didn't know if he even knew he was being recorded or just didn't care. Donna's hand was visible, fingers tangled tight in his hair, pulling his mouth harder against her, grinding down with a slow, possessive rotation of her hips.

Debbie could see the strain in Oliver's jaw, the way his throat bobbed as he struggled to breathe, to please, to survive the assault of sensation. The way he gripped her heavy thighs as he drank down sweat and juices. He was drowning in her, and Donna was using him like furniture, like a toy she'd purchased along with the bed.

Debbie's free hand crept beneath her waistband again. She tried stopping herself, to close the phone, to throw it across the room. Instead, her fingers found her clit, circling with a feather-light touch she knew would build slowly. She shouldn't. She really shouldn't. But she was already wetter than before, her panties soaked through, her hips lifting involuntarily off the couch cushions.

The third video of the night arrived.

Debbie was past the point of hesitation. No longer in control of her actions, she played the next video, not knowing what to expect. Call it a woman's intuition, but something told her this was a point of no return.

The angle was different. Static shot, positioned beside the bed. The frame captured everything in devastating clarity. Donna in the Amazon position, kneeling over Oliver, his legs thrown up over her shoulders, his feet in the air. They were both drenched in sweat, skin glistening, the expensive sheets beneath them twisted and ruined. The sound was on--flesh slapping against flesh, wet and rhythmic, punctuated by Oliver's broken moans.

"Mrs. Donna," he gasped, his voice high and desperate, cracking like a boy's as his body was being used by his landlady, not far from where her daughter slept.

Donna didn't stop moving. She slammed down harder, her hands gripping his thighs, her face a mask of predatory concentration. "Wrong," she panted, her voice clear as she leaned down, inches from his face. "Call me mommy."

Oliver had a brief moment of consciousness as he hesitated. Seeing this, Donna grabbed both his wrists, pinning them above his head as she went harder. Her cunt swallowing his cock was slow and deliberate. "Do it."

Oliver's head thrashed against the pillow, his eyes rolling back. "Mommy," he whimpered. "Please, mommy- so rough"

A switch flipped in Debbie.

The sounds from the video still filled the empty apartment--slap, slap, slap, Oliver's pathetic moans, Donna's triumphant grunts as she fucked her son. Debbie didn't care anymore. Her restraints had burned away completely, leaving only raw, animal need.

She yanked her leggings down to her knees, spreading her legs wide on the couch. Her fingers plunged inside herself, fucking herself with a violence that matched Donna's rhythm on the screen. She rubbed her clit in furious circles, no longer teasing, no longer pretending this was anything other than what it was.

The bed creaked under their combined weight, getting louder and faster with Donna's movements. The sound only matched by the chorus of their moans as she pounded away, using the blond as a tool to chase her own orgasm.

It was too much, phone sliding off her damp fingers. Debbie came, screaming into her own palm, biting down hard to muffle the sound, her hips bucking off the cushions, her vision whiting out. She kept her eyes open, fixed on the phone screen where her son was calling her best friend "mommy", fully corrupted, where Donna was replacing her in every possible way.