In His Dark Side Ch. 02

Chapter One

Derek's memory of his sex life with his ex-girlfriend was not a dull affair. By far, sexually speaking, Derek grew the most during his stint as Amy's boyfriend. The strait-laced, quiet, and unassuming girl was shockingly slutty, loud, and horny in bed. Her desire to be dominated loomed almost to a fault on the extreme side of things. Every week, it seemed she was buying different contraptions and toys for him to use and abuse her with. The reason why he broke up with her definitely wasn't sexual. It leaned more toward the reason of her being on the obsessive/stalker side of psychotic.

Every female she saw him talking to would turn into a crying fit because she thought He was cheating; every place he went, she wanted to come, and everything he did or thought she wanted to know. Like everything in life, it had some perks. When Derek finally realized on their third date that not only did Amy want him to fuck her constantly and in every which way, but she also was okay with giving him a blow job anywhere--literally, anywhere. Humiliation was one of Amy's collections of kinks, and being observed sucking Derek's cock at the school library, in class, in the theater, and at a bar would get her off.

It was terrific for the first couple of weeks, but then Derek was struggling to pass classes because she was trying to get caught while getting him to fuck her in public. Amy might have been a rich girl in college to fuck around, but Derek wasn't rich; he couldn't afford to fail a class. The breakup was the worst of it. They literally broke up six times. Six times, they had the conversation. Six times he had to fight through her tears and begging to suck his dick to make it up to him. Then, the thousands of texts, emails, direct messages, handwritten letters, and phone calls followed him for weeks.

So when Derek felt the clutch of panic in his chest when he heard Amy knocking on the library door with Amy's naked mother straddling his lap, he meant a panic he never felt before in his life.

"Mom? Are you in there?" Amy asked.

"Oop, yes, dear," Mrs. Miller said as she slowly straightened on her knees, shoving her breasts in Derek's face.

"What are you doing in the library?" Amy asked with confusion in her voice.

Derek grabbed Mrs. Miller's plump ass cheeks to help speed her getting off of him, but he felt resistance and then her hand back around his cock.

"Give me just a few minutes, honey. I'll be right out to explain-ahmm!" Mrs. Miller gasped as she sat herself down on his cock. Derek's thick head split her moist pussy lips open as he pierced her. Derek gasped as the sudden warmth and wetness squeezed around his member. Mrs. Miller pressed her lips together as almost tears glittered in her eyes. Like his cock felt so good inside her, it almost hurt to keep quiet.

"I won't do this!" Derek mouthed without saying a word. He let his raised eyebrows and enunciated lips send the message.

"Oh, fuck me... oh, fuck me... fuck me... fuck mmmm..." Mrs. Miller mouthed at first but then began to whisper as she rocked back and forth on his cock. When she started to get louder, Derek clamped his palm over her mouth and shushed her. "Ughhhmmmmmm!"

Mrs. Miller growled when he held her mouth shut, and she began to ride him harder, growling and panting into the safety of his tightly gripped hand.

Apparently, Amy isn't the only one with a laundry list of kinks, and I just walked right into satisfying this one. Like mother like daughter.

In the heat of the moment, he thought back to a similar situation when he fucked Mrs.

Thompson, and the solution he imposed, was to fuck her hard and fast and get it over it with rather than let the risky moment drag on. Bucking his hips up to meet hers, Mrs. Miller's eyes went wide as he stuffed her. She smacked her ass down on his lap harder and faster until his cock was thumping inside her pussy like a jackhammer.

The depraved sounds that gargled out of her mouth and were barely muffled by my hand sounded more primal and animalistic than anything a human could make. Her giant tits clapped together and smashed down on her chest and bumped into his forearm with every bounce. He could feel just how wet she was by the slick mess that formed on my crotch and inside of her thighs. Only then, when inspecting the pool of moisture forming in his lap, he realized Mrs. Miller had been orgasming for the past several minutes non-stop while muzzled by his hand. Another orgasm came when her eyes rolled back again, and a growing moan hummed beneath his palm as her body spasmed on his.

"Um, Mom?" Amy said with concern in her voice. Her words were inches from the unlocked library door. "Are you alright in there?"

Holding Mrs. Miller's hips down on his cock by gripping her hips so she couldn't bounce anymore, Derek nodded his head encouragingly as he lowered his hand from the cum drunk MILF twitching on his lap.

"Ohhh, yes dear. I'm, mmm, I'm just, uh, not feel too good," Mrs. Miller mumbled as she tried to regain her composure. "Just, uh, be right out."

She leaned forward, cupping his cheeks in her hands as she smiled down at the man. Her dirty blond hair fell around his face, creating a tunnel for just her eyes to meet his momentarily.

"Do you need a doctor? This is weird. Can I just come in?" Amy replied impatiently.

Derek's eyes went wide and then narrowed on Mrs. Miller forcefully. She bit her lip and hid a grin.

"No, no, honey. Not yet," she said, then whispered almost soundlessly to Derek. "I need your cum."

Derek knitted his eyebrows and mouthed the word, "No."

He tried to tell her to get off him, but she wouldn't listen. Instead, her eyes narrowed, and her lips parted as she hung her pink tongue like a dog. She rocked back and forth on his cock--as much as she could with him restraining her--and he could feel her pussy lips tightening and loosening on his cock as she worked.

Pressing her warm cheek against his, she whispered in his ear, "No, sir. I won't get off of you. I can't. Not until you fill me up with your seed. I need to make it up to you."

Derek moved his hands under her hips to lift her off him, but she wormed away and huffed as she started humping him again.

"Oh god," she muttered almost above a whisper.

"Shhh," he whispered.

"Just fuck me, oh my god," she whispered breathlessly in his ear as she continued to try to hump him. "Just fuck me, daddy. Fill me with your cum, and I'll be quiet. Oh, god, I promise I'll be a good cum slut. I'll keep my mouth closed and legs open. You can fill me up. You can take me. You can make me yours. Just--just cum inside my pussy."

Each word seemed to flirt with the edge of being too loud, and in Derek's head, he imagined Amy still standing on the other side of the library door behind him. He weighed the pros and cons and realized if he didn't do what Mrs. Miller asked, she could still tell Amy what happened even if she didn't catch them in the act. The safest course for now was just to give the woman what she wanted.

"Okay," he whispered and stopped trying to restrain her movements. She brightened with glee and leaned down to kiss him long and deep as she started riding him just the same way.

Shoving his cock inside her, she leaned back, and a pained looked bloomed on Mrs. Miller's face as the corner of one of her lips rose, and her eyes squinted.

"Oh my god, master. That's it... oh fuck. Fuck your slut. Take her. Use her. Use me," Mrs. Miller whined in a muted whisper. She took his hands and brought them to her plump and heavy breasts. Derek squeezed them and felt his cock flex inside her at the same time. "Mmmmm!"

The high-pitched squeal she released was just a bit too loud, but Derek didn't hear Amy through the door, so he assumed she had gone elsewhere in the house.

Good, let's get this done.

Pinching her nipples, he saw Mrs. Miller's eyes roll backward and whimper escape her lips. He forced his cock inside her.

"Oh, god, master... make me your cum slut, Make me your whore, make me your filthy fucking cum rag... oh, oh, oh god," she cried, fighting to keep her voice down as Derek pounded into her. Her tits clapping against her chest was nearly as loud as his cock smashing into her pussy.

"Mmm!" Derek gritted his teeth and grunted as he felt the orgasm strike. Spurts of cum exited his cock and filled her pussy as she clapped both of her hands over her mouth to stifle another orgasm. Her body was a jittery wet mess on him, and her clenching pussy on his still-spasming head felt almost too good.

It was then he heard Amy's voice from behind him, but it wasn't muffled from a door.

"Derek?"

Chapter Two

To say Derek's luck had run out would be an understatement of the century. Derek would have rather been caught naked in Mrs. Thompson's closet by his mother's entire book weeks ago than to have been caught cumming inside his ex-girlfriend's mother by his ex-girlfriend.

"Mom!?!" Amy yelled in an exasperated and, rightfully so, shocked tone of voice.

It was unbelievable that even then, after Derek had given into all of Mrs. Miller's conditions, including pumping her full of his seed, she still was resisting getting off of his lap. With her tits waggling back and forth as she rode Derek's attempts to escape like a bucking pony, Mrs. Miller spoke through her panted breaths.

"Now, honey. I know this is a shock, but it can't be that much of a surprise," Mrs. Miller said. "Why don't you come around here and have a seat, and we can talk about this."

Oh, screw this! I'm done being polite.

Scooping Mrs. Miller's ass and thighs in his palms, Derek stood, flexing his muscles as he lifted the mature woman as he did.

"Woop!" Mrs. Miller yelped and quickly clasped her hands around his neck. She protested and made demands, all of which literally fell on deaf ears as the ringing of shame blared in his eardrums.

Derek turned, and half dropped her back onto the couch. He saw Amy for the first time in years. She looked beautiful as ever. She had the same dyed dirty blonde hair as her stepmother, but Amy had poutier lips, a narrower face and waist, and a tattoo of a flock of hummingbirds flying down her arm. And Derek chagrinned at her wide-eyed expression with her hands cupped over her nose and mouth. After a pregnant pause full of awkward eye contact, her eyes dropped to see his messy half limp cock and slick hips and thighs from her mother's squirts.

Tasks I need to do: Apologize to Amy, put on clothes, and run very very far away.

While Derek struggled to figure out what to do first, his face brightened to a shade of red somewhere about a ripe tomato. He ended up doing a combination of all three at the same time, which didn't go well. He hopped toward the door while stuffing a leg into his pants and realized that he put his underwear on backward and inside out. Mrs. Miller followed him, still naked and attempting to pull the clothes back off while verbally sparring with her stepdaughter.

"We're all adults!"

"I told you he was attractive!"

"Maybe you guys can get back together because of me..." were all defenses offered by Mrs. Miller, and all were shot down by Amy as they should have been.

On the other hand, Amy didn't have much to say to her mother. Derek was the target in her crosshairs.

"You fuck my mother behind my back!"

"I sent you all those texts, those emails, and you can't respond to one of them, and then you do this years later!"

"What the fuck is wrong with you!?" Amy screamed as he stumbled out the front door. All her questions were statements, and questions were valid, and he had no response, so instead, he kept repeating 'I'm sorry,' and 'it shouldn't have happened,' as if he had just slipped and landed inside her mother.

Derek had gotten his car door open when he heard a downshift in the high-pitched screeching.

"Mom, mom! You're naked; go back inside. Mom! Go, I'll handle this," Amy said, bringing her tone down an octave to normalcy. "Derek, stop. Stop. You can't just leave. Do me the courtesy of at least coming inside and explaining this to me."

Derek hesitated half in his car. He hated the way she phrased her statement. He did feel he owed her an explanation.

"I apologize for the way you found us," Derek sighed. "That was... disrespectful. I let... I let my dark side take control when I shouldn't have had."

Amy shifted her weight, and he saw something different in her expression. Something behind her anger. "Well, come inside. Let's talk."

The hesitation lingered another minute before he agreed, but the darkness inside him reveled what that meant even before he knew.

He sat with Amy. This time in the large living room area with multiple oversized couches. Her mother disappeared upstairs to put on clothes for a time, and the two awkwardly caught up while they waited. It was a strange but familiar conversation, surprisingly. As if they just ran into each other at the bar rather than with his cock in her mother's vagina. She updated him on her job at a record label, the administrative side. And how she was just here to visit her mother when she caught them.

Mrs. Miller came downstairs and fetched coffee for everyone as it was growing late. She sipped her coffee, listening. She had cleaned up, redone her makeup, and now wore a white and blue sundress that hung to her knees.

"So glad you came back," she said.

"Look, I don't know all of why you were fucking my mom," Amy said with a shallow sigh and tilted her head. "But I know you didn't initiate it. My mom called you here and seduced you. I get it. I get my sex drive from her, so we can be hard to turn down."

"Yeah, that's for sure," Derek said, and they both laughed. Derek couldn't help but steal a peek at Amy's amazing breasts. They were barely tucked into a tube top that showed ample cleavage, and she wore a tight pencil skirt that hugged her round ass. Large gold hoop earrings dangled from her ears and jingled against her face when she turned.

If she was just coming to visit her mom, why is she dressed as if she was going to a club?

"I also know you've got a big and important job now; congratulations," Amy said and sat back in her seat and crossed her legs, apparently reveling in the eyeful Derek had stolen.

"Thanks," he replied. "I know we didn't end things great when we broke up, and we didn't start things off great now, but I came back here to apologize to the both of you. I also felt I owed it to you," he nodded to Amy.

"Well, how about you make it up to me then," Amy replied with a grin.

Amy scooted closer to his left, her breasts already brushing his shoulder as she turned to him. Mrs. Miller slipped into the couch seat to his right and crossed her legs as she observed with an amused smile. It was when Amy took Derek's hand in hers, moving it to her lap while leaning in to kiss him, that he realized all his suspicions were true.

Amy's palm pressed on his chest and caressed his rippling muscles as it lowered on him. Derek stretched his neck, feeling a spike of anger inside him. She leaned forward and pecked a kiss on his neck, her hot breath teasing him as she planted a second kiss on his jugular beneath his chin. The anger awoke the dormant darkness. A dark place he kept buried that enjoyed tormenting. The part of him that took advantage of those weaker than him meant that he took advantage of almost everyone.

Amy's lips pressed to Derek's mouth when Derek snatched the back of Amy's hair and yanked her backward. She cried out a whimper, something between pleasure and pain.

"This was you," he said matter-of-factly. "You created this entire situation. Manipulated me here," he nodded to Amy's stepmother, who sat on the opposite side of him, "offered up your mother all to get me right here. This was what you wanted."

He could see and feel Amy slowly shrink under the darkness that he imposed upon her. The innocence of her eyes mixed with the fear of her posture and the hooked seductive smirk in the corner of her lips. "Are you going to punish me?"

Derek sighed and stared, snarling at the floor before him. The anger he felt was like an awakening volcano. The dried husks of his exterior fell away as the rush of fiery lava and magama splashed to the surface. He knew it was what she wanted, but he would just have to enjoy it more than she did.

Pulling her by her throat, Derek kissed Amy's tender lips hard. They had a familiar feel to them as he bit her lip, making her squeal and shove his tongue down her throat and made her suck on it. The fruity taste of her cherry ChapStick brought him back to their relentless sex life all those years ago. Their kiss was just heating up when he felt the warm presence of her stepmother nearing his right. Derek shoved his ex-girlfriend away, making her fall back into the couch.

Slipping his hand behind Mrs. Miller's neck, his fingers cut through her long hair and pulled her lips to his. Unlike her stepdaughter, Mrs. Miller melted to Derek. Their kiss was wet and passionate as she wrapped her arms around his neck, pressing her huge breasts into his chest as their tongues circled each other.

"My mom's been a baaad girl," Amy slapped her mother's ass and spiked a high-pitched hum out of her while she kissed him through her tongue pressed deeper into his mouth, lapping at the roof as she purred.

Amy's fingers were busy unclicking Derek's belt and yanking his pants and boxers away. At the same time, Mrs. Miller's desperate fingers did the same with his shirt and broke the kiss long enough to rip it over his head before returning. Somewhere in the back of his head, Derek thought this was a perfect example of life over the past month for him. He was a victim of his circumstances. Constantly reacting.

Always having things done to me but never feel like I have a choice.

Was this the rest of my life? Being pushed around from one decision to the next? Having sex with women who demand it when they demand it? Taking cases at work, I'm ordered to. Shoveling other people's messes and becoming a criminal just because I'm afraid of the social consequences being loitered over my head?

"Mmmm... I've missed this cock more than you could ever know..." Amy purred as her delicate hand closed around his member and slowly stroked up and down.

Mrs. Miller slipped her hand down Derek's bare inner thigh and back up. Just as her daughter's lips closed around the head of his cock, Mrs. Miller's warm palm gently cupped his balls. Her middle finger gently massaged the loose skin between his scrotum and his two testicles as her middle finger carefully rubbed the pad of her thumb over the left ball for a few seconds, then the right. Amy's lips explored deeper down his shaft as he hardened and flexed. Her dainty mouth was stretched and filled with his thick meat as she had to push her ass out along the couch to get a better angle to bob her head along the length of his dick.

Derek released an extended growl into Amy's mother as they kissed, and the mature woman swallowed it just as her daughter swallowed his cock. Reaching out with his left, Derek rubbed down Amy's narrow back to her taut, tight ass and groped it through the fitting black pencil skirt. Without prompting, Amy continued sucking his cock but reached behind her with one hand, unzipped her skirt, and scooted out of it. While she did that, Derek slipped his right hand up between the loose sundress Mrs. Miller now wore and immediately felt the heat radiating from her sex. His right hand's fingers found her messing pussy lips just as his left hand found her daughter's slick twat.

"Mmm mmm, oh god, yes. Finger fuck me," Mrs. Miller said in a high pitch between kisses as his middle finger entered her.