In His Dark Side

Chapter One

"Mrs. Miller?" Derek blurted out in stunned surprise. "Oh, Derek, how are you? It's been too long. Amy is doing good but she never gives me updates on how you are doing! I've never liked how things ended between you two. You guys were such a cute couple!"

This was how it was with the Miller family. Both Amy Miller, Derek's ex-girlfriend, and her mother, Ashley Miller, were talkative ladies who believed the world revolved around whatever they thought about at that particular moment. Which, to some extent, it did. The Millers were the second richest family in Austin, Texas. Which meant they were one of the richest in the country.

"Mrs. Miller--um, hi, how are you?" he stammered and looked around as if there might be cue cards somewhere to read. Derek was on his lunch break. Sitting in his car with the radio turned down and a half-eaten sandwich in his lap, he looked around to make sure none of his supervisors were near his vehicle. He was a recent hire at an enormous law firm which meant he was one level above pond scum there, but he was starting to build his reputation. "Sorry, I'm just a little surprised. Is--is everything alright? Is Amy--"

"Oh, she's fine! She's fine! Sweet of you to worry. No, she still is quite sad, though, from your guys' break-up. I don't hold it against you. The heart wants what the heart wants."

Derek didn't know how rich Amy was or how influential her family was when he first started dating her in law school. He knew she had a lot of expensive toys and a nice car, but he didn't expect just how rich she was until she met her family. He only met her father once, but he was nice enough, though distant. He worked in the oil business and was gone more days of the year than present. Both Amy and Ashley Miller adored Derek for the year and a half they dated, and talks of marriage happened--between the women, mostly. Though Derek considered proposing briefly, Amy's... darker side got the better of their relationship, which ultimately ended their relationship two months ago, just before graduation. It was quite a messy breakup, too. Clingy and stalker didn't begin to describe the girl. This was only one of the many reasons why Derek was apprehensive about her mother calling him now.

"Yes, yes," he said awkwardly. "So, Mrs. Miller, was there a particular reason--"

"Oh! Yes, forgive me. I know you're quite busy with the new job and all. Congratulations, by the way..."

"Thank you," Derek smiled but wondered how she knew about his new job. He got the job after breaking up with Amy, he didn't tell anyone who would have told Amy, and he was such a low hire it wouldn't have been announced.

"Well, Amy had a box of your things that you never picked up after your break up. I figure she meant to get them to you but forgot about it. Anyways, I found them today and wondered if you still wanted them?"

"Ah, yes, I almost forgot about them," Derek said suppressing his sarcastic tone. He had not forgotten about them. One item was his personal laptop that Amy had lorded over his head as a poker chip to get back together with her. He was forced to buy a new one during his poorest time between passing the bar and starting at his current job.

Well, late is better than never, he thought.

"Thank you, Mrs. Miller. I'd be happy to come by to pick it up. I'm working late tonight. Is eight o'clock too late?" he asked.

"That will be fine, dear, I'm here all night," she replied. Derek thanked her again and hung up. He scarfed down the remainder of his sandwich before heading back into his office.

Well, selling my old laptop will at least put a dent in the cost for the new one, he shrugged. He was making decent money now, but nothing to write home about. He still lived in a one bedroom apartment because housing prices were too high in Austin. A couple more years of saving and raises and he would be in a financially good place. Perhaps, then he would attempt dating again.

This time it would be with a woman who was different than Amy. Someone who didn't... feed into my darker pleasures.

Chapter Two

There was an eerie ache in his belly as he drove the familiar streets to Mrs. Miller's house. It felt like he was the main character in a horror movie and walking into a trap where the killer was waiting with a knife. His paranoia probably sounded ridiculous to anyone who didn't know what kind of breakup he had with Amy. He drove up the long winding driveway in the darkness of the night and followed the garden lights to the front door to knock, even though he knew they didn't use that door. It felt wrong to approach the back door. Knocking, he was greeted at the door with a leaping hug that was more familiar than he expected.

"Oh, Derek! It's been so long!" Mrs. Miller's large breasts smashed into his chest, and her hands latched onto the back of her shoulder blades.

"Hi, Mrs. Miller, nice to see you again," he said through a nervous smile. He knew Amy wasn't there because he did a search for her vehicle before putting his in park. Plus, he knew from facebook stalking her earlier that she now lived and worked at a law firm in Houston.

"Come in, come in!" she said breaking the hug just to usher him deeper into the house. He followed her with a grin lingering on his lips and feeling a familiar itch on the back of his neck. Derek was a confident man, tall, and good looking so girlfriends and relationships had never been hard to find. This chosen celebesy for the past two month had been the longest he had gone without sex in years. Hell, he had been so busy with his new job, he hadn't even masturbated since graduating. The result being him now noticing the eye-popping curves of Mrs. Miller for the first time.

Mrs. Miller had long dirty blonde hair that flowed over her shoulders. The white and blue sundress she wore hugged her thick ass cheeks. He watched them swish from side to side as he followed her. When she turned into the house library his eyes followed the long dark line of cleavage her large breasts produced. The luscious body of his ex-girlfriend's mother was exquisite. Her soft-featured face showed the beautiful resemblance between the two. Like mother like daughter.

Derek felt his mind drifting someplace he didn't want it to go and shook it back from oblivion.

"Come in here; we can talk in the library," Mrs. Miller said as they walked the maze of her house to a rich library. She closed the door, and they sat on the brown leather couch. The room was decorated in maroon, gold, and deep browns of mahogany. Derek didn't know if this house was big enough to be considered a mansion, but it definitely was big enough to get lost in. Derek doubted if this library was ever used by anyone other than the house cleaning staff.

"Would you like something to drink?" she asked.

Derek had to focus on not looking down at the great view of her breasts as she bent over the bar. That's it. When I get home, I'm jerking off. A few more days of this level of deprivation and I might end up doing something stupid like fucking an ex's mom...

"No, thank you," he said, but sat to be polite.

She sat beside him, took a sip of her vodka tonic, and set it down on the coaster on the table. "You know, I've always admired you. When you dated my daughter, I thought you were the one. You were a sexy man with a good head on your shoulders; oh, I wish you two worked out."

"Yeah, yeah, how is Amy?" he asked filling the void.

"She's good. Works in Houston for a movie studio. Not sure what she does," Mrs. Miller's hand rubbed over his knee. "Although maybe its better things didn't work out between you two. It poses opportunities."

Derek was so distracted by his ex-girlfriend's mother's hand rubbing up his thigh to his crotch that he almost missed the last words she spoke.

"Opportunities?" he asked with raised eyebrows.

"For your careers, of course," she shrugged innocently but beamed a smile that said otherwise. "Your degrees took you both in different directions. Different places. Sometimes letting go is best for everyone."

"Hm, yes," he said and began eyeing the room for his box of things.

"You know," she said with a devious grin as she took another drink. "She did tell me about the real reason you broke up with her. The 'dark side.'"

A flush of pink hue warmed his cheek, and he felt a twist in his gut. Despite his discomfort, there was another side to him that was irritated. Upset that she thought she had the ability to hold this over him without consequences.

"Ooooo, I think I can see the dark side appearing in your eyes now," Mrs. Miller joked as she giggled. Playfully, she patted his leg. "Derek, this dark side business is nonsense. There is absolutely nothing wrong with enjoying being a little dominant in the sack. Just look at my daughter, for heaven's sake. She didn't mind. She loves a rougher man in the sheets. Sure is better than those tender boys who barely touch you. She gets that from her mother."

Mrs. Miller gave a wink to Derek as she finished off her drink and he only glared back. The older woman's cheeks were growing pink as well, but he suspected it was from the booze and not embarrassment.

Setting the glass down, she scooted closer to him. She brushed her hair over her shoulder as she leaned near him, her breasts nearly touching his shoulder.

"You know, if what you're worried about is going too far, I think you just need the right partner to find your way with," she said rubbing her palm over his chest and down to his lap. "Maybe a used, older woman who needs to be put in her place."

Mrs. Miller rubbed his crotch through his pants, up and down. His firm cock pressed back in a silent communication. Turning to face her, the woman was taken back by the man who looked at her. The set jaw, the glared eyes. He could see the worried excitement hidden in her eyes.

Without warning, he snatched the back of Mrs. Miller's neck and pulled her lips to his. They kiss long and they kissed deep and he felt her body melt like molten chocolate in under his touch. Derek tasted the cool bite of the remaining vodka on her lips and tongue and bit her lip, making the woman coo in agreement. Taking her small, tender hand in his, he guided it down to his crotch and pressed her fingers onto his bulging shaft.

"Mmmm..." Mrs. Miller whined as she broke the kiss. One hand stroked his cock through his suit pants in an exploratory way. The other slowly undid his belt. "You know Amy and I are far closer than most mother-daughters... especially considering she's technically my stepdaughter, but we don't call ourselves steps. Oooooo... someone's happy to see me!" Mrs. Miller purred and giggled as she gripped the flexing shaft through Derek's pants.

"We talk, we tell each other everything, mmmm..." Mrs. Miller continued. She had Derek's pants unzipped and was admiring the pre-cum stain on the front of his boxers as she half lay on him. "She always told me how good you were at fucking her silly. How wonderful that cock of yours was... God, you don't know how many times I slipped a hand under my covers when you and Amy visited and stayed the night, just wishing that you would sneak into my room and have your way with me..."

She peeled his stained boxers down over his cock and began to lower her lips to his shaft.

Chapter Three

Derek snarled down at Mrs. Miller as he gripped the back of her head and forced his cock deeper inside her ever-widening mouth. Her lips, mouth, and throat made a wet gurgling, almost gagging sound as she deep-throated his shaft. Her entire head bobbed on his shaft as her saliva poured over his cock and drowned his dick and balls.

Mrs. Miller needily grabbed at his hips and forced his cock to touch the back of her throat. He grabbed a lock of her hair and pulled her up and down on his shaft like she was a sexy toy. Derek moaned and released her hair when he felt himself nearing the edge.

"Oh, fuck yes, Derek, cum in my mouth. Cum all over your whore's mouth!" Mrs. Miller removed his cock from his throat long enough to speak. Her eyes were watery, and her makeup already started to run. Lines of drool clung between the tip of his cock and her lips. "You like these tits? I've seen you stare at them many times before. I bet they'd feel wonderful wrapped around your cock."

Mrs. Miller peeled the straps to her dress off her shoulders and let the weight of her dress fall to the side, revealing her massive breasts. Scooping up the sides and underneath her breasts, Mrs. Miller pushed her chest forward and slid his wet shaft between her tits. As she masturbated his shaft with her tits, Mrs. Miller wrapped her lips around the head of his cock again, and this time, the pressure was immense. Derek felt the head of his cock flex continuously as her tongue lapped circles around his head. probing the tip, she took a long lap at the base of his shaft before bobbing her head. the entire time her breasts strangle the meat of his shaft.

When Derek came, he saw white flashes in the corner of his vision, and his eyes rolled backward. Mrs. Miller didn't relent when the backup of warm salty sperm splashed into her mouth; in fact, she pressed further down. Her lips slurped and slopped down his shaft as his flexing continued and the pleasure overwhelmed him. Even after he finished, she would stop. Her lips were like a vacuum cleaner, and they sucked him even as he finally went limp. After ten minutes of that and after she had licked and sucked every inch of his shaft she finally relented, popping her lips off of him.

"Mmmm you're as tasty as I hoped," Mrs. Miller hummed a smile and slid up his front, looking for a kiss.

Derek leaned back and put his hands on her chest to stop; she changed tactics and licked his palm, then seductively began to suck his finger as if it was a cock. Her eyes lingered on his.

"Mmmm... sorry baby, I'm orally fixated. Just like my daughter," Mrs. Miller said with a mischievous grin and a wink.

Derek fought the distraction and pressed forward. "Did Amy put you up to this?"

A playfully naughty grin beamed on Mrs. Miller's lips as she giggled and teethed on his thumb before shaking her head from side to side. "Ah ah ahhh. We don't kiss and tell. Fuck and tell maybe, but not kiss..."

Mrs. Miller's brushed down his front and found his soft cock. Like a witch casting a spell, her fingers circled his entire shaft before gripping it and slowly pumping it to life. His cock responded and woke like a zombie from the dead, slowly stiffening in her palm. Derek did a fast calculation and figured whatever drama he might create by fucking his ex-girlfriend's mom he already created by cumming in her mouth.

Derek leaned forward and pushed Mrs. Miller's chest, making her fall backward to her side of the couch. She tried to sit back up, but he was already on her. His hand slid up her silky-smooth thighs and disappeared under the skirt of her dress.

"Oh, Derek... yes... yes... take me... take me!" Mrs. Miller groaned as his fingers found her pussy. It was lightly shaved and already a mess of juices as she must have really loved giving him that blowjob. His middle finger slid inside her pussy like it was cutting into warm butter. Then he added his ring finger. "Oh, god! Yes. Yes! Fuck me just like I fantasized. Take me. Make me you whore!"

One of her hands snatched my other hand and jerked it to her throat. His hand wrapped around her neck and gave firm pressure on her throat that made her gasp and groan. Derek's arm flexed as he pumped the fingers in and out of her hole and made her entire body rock as he finger-banged her. The woman's thick thigh parted impressively wide, causing her sundress to fall to her belly exposing her dripping wet pussy and pale inner thighs.

"Yes, baby... choke me. Choke your fuckin whore!" Mrs. Miller cried as he gripped held her down by her neck and stuffed her with his other hand. He arched his thumb so the pad of it jabbed her clit with every thrust. A swiping motion turned the move into a fast rub as he fingered her pussy and circled her clit. The octave and immediacy of her moans changed when he started hooking up his fingers and pressing on her G-spot with every thrust.

"Ahhhh! Oh god! Fuck! Fuck me! Fuck me!" she squealed and pushed away from him while holding onto his arm like the pleasure of the fuck was too much for her body but yet she needed it. "You're gonna make me cum... oh god, you're going to make me cum... I'm cumming... I'm cumming... ahhh ahhh ahhhh!"

A tremor vibrated through her hips as her eyes rolled to the back of her head and her large tits clapped and circled on her chest. A dollop of juices squirted from her pussy and splashed on his hand and wrist before wetting the couch. Immediately, Derek jabbed his fingers back inside the woman and repeated the same fingering motion but this time more roughly and fast.

"Oh fuck fuck fuck fuck! Ugh!" Mrs. Miller screamed through gritted teeth as he finger fucked her. Her back arched and his forearm was swallowed by her massive breasts on either side as he kept a hold of her tender throat. "Oh god! Again--I'm cumming agai--ugh!"

Derek pulled his fingers out just as her thighs flexed closed for a brief moment and she squirted again. This time her body went limp to the couch as she panted and moaned in exhaustion after.

"Ohh god... oh my god..." she sighed between breaths.

Derek kicked off his pants and underwear and positioned his hips closer to hers. His hard cock rested against her crotch. When the girth of his shaft rested on her tender pussy lips, Mrs. Miller looked down at it like it was a gun pointed at her.

"Oh, god. It's so big... Jesus," she groaned and began to worm her hips around expectantly. "Oh please, fuck me, master. Fuck me. Put it in me, master."

The words seemed to pour out of her mouth seamlessly as if she had been waiting years to say them.

"Tell me about Amy," Derek said as he dragged his palms up and down the face of her bare breasts. Her hard nipple cut into his hands as he did. "Did she put you up to this? Was this her plan?"

"Ooooo I can't, I can't. I just ca--god. Please, sir, just put that thing in me!" she begged.

The meat of his shaft flexed and pressed down on her slit. When he leaned over her it ground on her clit making her teeth chatter and her voice high-pitched and squealing. He fed the tip of his thick cock into her pussy and felt how easily it went in. It begged for him to enter but he didn't give it.

"Oooo come on! Please please, please! I'll be your free-use toy! I'll be your fuck doll MILF to use whenever you want! Just give it to me!" she begged.

He was lost in thought when he jammed his long hard cock into her pussy. Her soaking wet wall squeezed around his shaft as he filled her up and she screamed.

"Ahhhhh gahh! Yes!"

Holding his cock inside her, he felt pressure on all sides. Her small, tight cunt choked his cock like it was trying to hold onto it as Mrs. Miller squinted and panted in near hyperventilation.

"Ohhh, fuck me. Fuck me, master--ahhh!"

Bucking his hips, he pulled out and slammed his cock back inside her. Mrs. Miller's eyes went wide her face looked pained, but her moans were high and full of pleasure. Pressing on her thighs, he widened her legs to near splits with one foot almost touching the floor and the other straight in the air. Each buck of his hips fucked her into the corner cushions of the couch. Her hands switched from cupping over her mouth to muffle her excessive screams to gripping at her thighs to spread her legs just a little wider to fit a little more of his massive cock inside her.

"Oh fuck yes! Fuck your bitch! Fuck your bitch! Fuck me into this fucking couch like the needy whore that I am--oh fuck!"

Mrs. Miller's tits bounced forward and back on her chest like waves through a wave pool. Her heavy breasts looked like thick doey pancakes floating on her chest. Her body was folded inward so that her drooling pussy and his penetrating cock almost folded on top of her face that was stuffed into the couch.