Eager to Please

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

Chapter 2

The computer screen lit up the dark room, a low hum emanated from the CPU. Oliver was sprawled on the bed, staring at the ceiling. It turned out that even the distraction video games provided for him were not enough to take his mind off what transpired between him and his landlady. It had been a few days since then, and thoughts of her still dominated his fantasies.

Things had been a little tense around the house. The first morning after it happened was awkward to say the least. Oliver tried to avoid his mother while she tried to do the opposite. Debbie suddenly wanted to spend even more time with him, asking probing questions which Oliver tried his hardest to side-step.

As the boy lay in bed, he tried to rationalize Donna's actions that day, but each time it played in his head, he ended up getting aroused and touching himself, imagining what could have happened if she hadn't stopped. Afterward, he would be overcome with a sense of shame, mentally scolding himself for thinking of Mrs. Donna that way.

His internal torment was interrupted by the pinging of his phone; someone had sent him a text. Wondering who it might be at this hour, he picked it up. His heart dropped as he saw who the sender was.

"Hey, handyman, I need help moving some boxes around the house. Come over this morning so we can get started early. - Mrs. Donna"

He stared at the message for what felt like hours, a mix of fear and arousal spread across his body. It looked so casual, almost like nothing happened.

'Maybe I'm overthinking this, it probably was how she treated her daughter too, right?' he thought, almost convincing himself that was the case. He decided to pretend it never happened and do an honest job for an honest pay. With his new resolve, he got off his bed and headed for the bathroom.

While Debbie slept, fragmented images assaulted her from all sides: Oliver working on Donna's sink, but she's watching from the doorway. Donna sees her, smiles, and pulls Oliver's face to her chest. Debbie wakes up in a cold sweat, chest heaving, and confused. The same familiar heat running down her lower abdomen. Running her hands on her inner thigh, she was horrified to feel her wetness.

'I'm sure it's nothing, don't think about it too much,' she thought, as she got up to wash her shame with a long bath.

At the breakfast table, the tension between mother and son was thick. They tried making small talk as they ate, attempting to bring back some semblance of what they had before.

"Mrs. Donna needs my help again today," Oliver said, trying to sound as casual as he could.

The breakfast table went silent. Debbie's fork hovered halfway to her mouth, eggs dripping.

"Again?" The word came out too sharp, too fast.

Oliver's shoulders tensed. "Yeah. Moving boxes or something. She texted me directly." He said the last part like a confession, like he did something wrong.

Debbie set her fork down carefully, her dream still clinging to her like sweat. She could almost smell Donna's perfume in her nose, could feel the shameful wetness from earlier that hadn't fully faded. And now he was going back.

"She could hire actual movers," Debbie heard herself say. "Professional ones. With insurance."

"Come on, Mom." Oliver said with a nervous chuckle, believing she was making a joke, "It's nothing so serious, just some boxes she needs help with. She pays well, too."

Debbie sighed as she continued her food. This wasn't fair to him. She didn't know what was going on with her, but she shouldn't push that onto her son or to Donna; she was her best friend after all.

"All right, Mr. 'handyman'. don't stay out too late, okay?" she relented, rolling her eyes before putting on her signature smile.

Oliver's expression brightened, but only for a second. His phone buzzed in his pocket. He didn't check it, but they both knew.

"I'll be back for dinner," he said, standing. "Promise."

He kissed her cheek -- leaving it warm and tingly -- and was gone before she could grab him, could hold him, could say she wanted him to stay after all.

-

The cool weather helped Oliver clear his mind as he walked. Mrs. Donna was just being friendly. She was just happy to finally get her faucet fixed so quickly, that's all. The blond almost laughed at himself for being so silly about this whole ordeal. He just had to do his job and get paid.

The garage door was open when Oliver arrived, morning sun spilling across the concrete. Donna stood inside sorting boxes, and Oliver's mouth went dry.

She wore a white tank top that clung to her torso, thin enough to show the faint outline of her bra underneath, and denim shorts cut high on her thighs. Her dark hair was pulled back in a messy bun, exposing her neck. She looked nothing like the businesswoman from before -- she looked like a woman who worked with her hands.

"There's my handyman," she called out, not turning around. "Just in time."

Oliver swallowed, his palms already sweating. "Hey, Mrs. Donna." He shuffled inside and stood next to her. "You're doing it yourself? Isn't Meg helping?" he said, looking around.

Donna finally turned to face him. "Megan's at a friend's house all day today, " she said with an innocent smile. "Looks like it's just the two of us."

Oliver couldn't control the blush from appearing on his freckled face; her comment brought back memories. Memories he was trying to suppress.

The attic stairs were narrow and steep. Donna led the way, carrying nothing, just pointing at which boxes to take. Oliver followed with his arms full, his eyes level with her calves, her thighs, and despite his best efforts, noticed the way her shorts rode up with each step. She knew. She moved more slowly on the stairs, letting him look, letting him stumble once so his face nearly pressed into the back of her leg.

"Careful," she said, not turning around. "These old steps are tricky."

They worked in silence for an hour, the attic filling with heat and dust with constant movement. Donna found reasons to be close -- reaching past him to steady a box, her chest brushing his shoulder, her hand lingering on his back to "guide" him through the narrow doorway. The constant physical contact between them was slowly building something within Oliver that he desperately was trying to deny.

"That was the last one, let's take a load off," Donna announced, wiping her forehead with the back of her hand. "I made lemonade."

They made their way to the kitchen, sitting on stools in front of the counter beside each other. The cold lemonade was refreshing to the soul after carrying so many boxes.

"So," she said, stretching her legs out, her thigh pressing against his. "You never told me. Do you have a girlfriend?"

Oliver choked on his drink. "No. I mean-- no."

Donna smiled, slow and predatory. She set her glass down and turned to face him, eyeing his features. "Little Olie, so innocent. But we both know that's not true now"

Donna stood up, slyly went towards him like he was prey, and he was. She settled behind him, waiting for his reaction. Oliver dared not move; he was stuck in place like a deer.

"I saw those eyes, the way they looked at me, at my clothing of choice for today," she whispered into his ear, hands already moving from his shoulders down to his waist. "You're such a bad boy, you need to be punished."

Oliver was beet red at this point as he sat there on the kitchen stool. He did not resist her; he couldn't. He let her explore his body, moaning into her touch.

"Mrs. Donna-"

"Shh, don't say anything." Without warning, her hands moved under his shorts, past his boxers, and landed squarely on his hardened member.

A gasp escaped the blonde's throat; he was overwhelmed by the assault of new sensations. He knew this was wrong; he knew he shouldn't let her do this to him.

"Hmm, so naughty. You were hiding this from me all day, right?" Donna said as she held his cock and slowly started pumping. She could feel him trembling in her grasp; seeing him like this sent tremors down her spine. Suddenly, the freckled boy's neck looked delicious. Donna ran her tongue all over the side of his neck, sucking the soft skin like a woman possessed.

Too aroused to even worry about leaving a mark on his neck, she kept at it, tasting the salt that had accumulated. Her hand stroked faster beneath his shorts.

"Mrs. Donna, I- I'm.." Oliver suddenly went rigid as the landlady felt something wet coat her hand. She came out of her trance as she watched the boy hunch over, gasping for breath. Fuck, she was so turned on right now.

Donna looked at her cum covered hand, bringing it closer to have a taste of him. That might have been a bad idea because it only made her more hot and bothered.

"You did so well today, Olie" she said, still licking her hand. "I could pay you now, or you could earn a bonus for doing one more job for me"

Oliver looked up at her. He couldn't speak; all he could do was nod

"So eager to please..." the taller woman said, biting her lips. "Take off those shorts, I'll have them washed and dried later. Wouldn't want your mom to worry now, would we?"

After complying with her order, he stood there in the kitchen, bottomless. Not knowing what would happen to him next made him flustered, but was already making his dick hard again.

Donna, after putting his clothes in the machine, stood in front of his semi-naked form. "Now to earn that bonus," she placed her hands on his shoulders. "Get on your knees."

-

The front door clicked open hours later than Oliver had promised. Debbie was on the couch, pretending to read, her eyes glued to the clock since five.

"Hey, Mom, sorry I'm late," Oliver called out, his voice too high, too casual. He made a beeline for the hallway, avoiding the living room entirely.

"Oliver." Debbie stood, book falling to the side. "Dinner's cold. I was worried."

"Sorry, took longer than--" He turned, and the kitchen light hit his neck.

Debbie's breath stopped.

Three dark marks, clustered just above his collar. Not red like fresh bites, but purple-edged, unmistakable. Sucking marks. She'd given hickeys before, back in the day. She knew what it looked like.

Oliver's hand flew to his neck, too late. "Mosquitoes," he said, fast and brittle. "Got me good in the garage. Swollen, you know?"

"Sure," Debbie heard herself say, her voice almost betraying her, chest beating at the possible implication. "Mosquitoes."

She watched him nod, relief flickering across his face, watched him escape to his room. She stood in the kitchen for ten minutes, staring at the space where he'd been, a million thoughts racing through her mind.

The brunette was a mixed bag of emotions, not wanting to confront that now-familiar heat running through her body, she opted to settle her nerves by clearing the dining table and putting the uneaten food in the fridge.

The next day was pretty uneventful. Debbie decided not to look too deeply into what could have transpired at their landlady's house; she found it was easier to stay in limbo. There was nothing concrete to go off from after all. She made a point to spend much more time with her cute son. Oliver agreed to it with little convincing; he was such a mama's boy.

Day easily turned to night, and after a day of mother-son shopping, they both retired to their rooms after a quick dinner. Debbie was mindlessly scrolling on her phone in the dark, looking for some new recipes to try. She suddenly received a text, coming from the last person she wanted to think about right now.

Donna: Hey, bestie, check it out. Sent you a vid.

Debbie's thumb hovered. She almost didn't open it. Some part of her was still mad at her. She lay on her bed in silence for a few more seconds before curiosity got the best of her.

The video loaded. POV shot, shaky, looking down. A woman's torso, Donna's torso, her tank top pushed up, her breasts heavy and swaying, dripping in a sheen of sweat that caught the dim light. Between her legs -- kneeling -- a head of dirty blond hair. Freckled shoulders. A familiar gray shirt, now wrinkled, bunched at the collar.

The boy's face was turned away, buried in her, but Debbie saw the ear. The shape of it. The small scar from when he was six and fell off his bike. She saw the way his hands gripped Donna's thick thighs, his knuckles white.

Donna's hand entered the frame,  her manicured nails looking like claws as she fisted that dirty blond hair, not gently, but possessively. She guided him, forcing him deeper, and her voice -- breathy, cruel -- said: "That's it, baby. Just like that. So fucking eager-."

The camera angle shifted slightly, giving a horrifyingly clear view of the boy's jaw working, his tongue lapping, the slick, obscene sounds of his submission mixed with the strained moans of her best friend drowning out the silence.

"Fuck- keep going. Such a good boy."

The video cut off. Thirty seconds. Enough.

Debbie's phone almost slipped from her hand as she stared at it. She was wet -- soaking -- her body betraying her before her mind could catch up. She pressed her thighs together, gasping, hating herself, hating Donna, hating the way her hand drifted down without permission.

"That bitch," she whispered to the dark room, overcome with a sense of betrayal and... arousal. She didn't know when her thumb tapped the play button again. She bit her lip, trying to break the spell that had come over her. It was futile; her legs were already spread wide as she fucked herself with her fingers. Playing the video over and over as he pumped with increased intensity, still biting her lip but this time to stifle her moans, her breathing becoming ragged.

The room was filled with the sound her wet cunt made, sweating from her intense activity. Debbie gritted her teeth as the knot in her came undone. Her orgasm hit her like a train, eyes rolling into her skull, squeezing her thighs together as she jerked involuntarily.

She recovered not long after, and it dawned on her what she had just done. Putting away her phone, the brunette held her pillow as the shame hit her. She had just jerked off to her best friend with someone who was almost definitely her son, and she had never came so hard in her life. The fact scared her, taunted her, made her question herself over and over again. After what felt like hours, sleep finally found her.