The Bully & the Brat: Envy

"Good evening, ladies."

"Uh, Hi, um...."

Anna swallowed her crush, but the gorgeous man had indeed caught her off guard. He was a young professional and looked stylish in a navy blue suit. His blonde shaggy hair was an alluring addition that made him appear less stuffy than most suit-clad men.

"Um, I'll be with you in a moment....."

Anna looked toward the post to see if Marsha would be willing to help the cute guy, but she wasn't in place. She looked back to see his pale blue eyes roaming her body.

"You can take a look around. Are you looking for anything specific?" She nervously bit her lip.

"I wasn't looking to buy anything, pretty girl," He said in a mild southern drawl that made her blush and sparked her curiosity, "I was hoping to speak with the owner. Is he around this afternoon?"

"Oh, sorry, mm, I think he's in the back," Anna nervously giggled, holding her hand to her heart, "If you change your mind about buying something, let me know, we are running a sale. No credit check."

The stranger beamed, toying with the neat blonde hairs that teased his chin. Licking his lips, he shook his head.

"I think I'll be okay, sweetheart. I apologize for interrupting," he said, his eyes flickered toward the customer and then back down to her.

Anna watched his stroll to the back. He broke for a second glance at her, and his sparkling stare made her heart race. Suddenly remembering she would tie the knot soon, she turned around to confirm the sale.

A few minutes later, Marsha interrupted the sale again by informing her she would leave early. Anna was happy about her exchange, knowing the money would be hers, and she could care less about being abandoned yet again. She finished the customer's paperwork and then called Marty to inform him he had a delivery to make. The rest of the day ran smoothly, with a few people coming in to look around.

Anna hadn't seen Jeff all day until he emerged from his office at 6 pm.

"Anna, close up and come here," he called out.

His voice dampened her mood a bit. She could only imagine what he wanted and took her sweet time finishing up her work.

Anna walked into the office with a frown but perked up, noticing the handsome stranger was still there. His face was hard to read, but he gave her a quick, polite smile. He was boyishly handsome, perhaps a few years older than her. As he rose from the couch to walk over, he extended his hand.

"Anna, it's nice to meet you," he smiled, "I'm Raymond-"

"Little Ray," Jeff tauntingly chuckled, wanting to forgo revealing his last name and damped his half-brother's charm.

Ray smirked, knowing his brother was intimidated by him. He had something Jeff had lost years ago, his youth. Although the brothers were far in age, they were close and freaky enough to swap women. Looking at his future sister-in-law, he smiled, taking in her voluptuous frame.

"Damn," he whistled, "You didn't tell me about all this," he spoke out with interest, reaching down to claw at her plump ass.

Shifting, Anna frowned at his unauthorized touch and backed up into Jeff.

"My apologies, but you've got a nice ass on you, sweet girl," he winked.

Anna creased her brows and placed her hand on her hip. This stranger was just as crude as her soon-to-be husband.

"You want to ride on this cock, baby girl?" Ray asked, patting his growing erection.

"No." Anna scoffed.

Ray arched his brow while Jeff hid a chuckle.

"Kate didn't tell you? My little girl is a prude, little Princess," Jeff remarked.

"She told me she was homely." Ray chuckled, "Should have known that was a lie. She's adorable, take that ugly uniform off, and you got yourself a little cam girl."

Offended, Anna turned to him with a frown, but before she could give a snarky reply, Jeff seized her, lifting her body to his chest.

"Stop!" Anna squealed, kicking her legs out.

"Hush that fuss, little lady."

Smiling at this half-brother, Jeff quickly pushed her further and parted her legs. Her feet dangled on his large arms, exposing her crotch to the stranger.

"Put me down!" She shrieked, twisting her hips to get loose.

Ray positioned his hand on the seam of her uniform pants, and she wiggled to remove it. He rubbed softly around the thick fabric.

"Don't fucking touch me!"

"She's not very friendly," Ray frowned at Jeff.

"She likes to fight," Jeff responded with a chuckle, then whispered in her ear, "You wanted that 50 thousand, right?"

"You are a fucking liar!" Anna yelled.

"Hush, girl," Jeff warned

Ignoring their back and forth, Ray continued rubbing her private area, "You need to be tamed, don't you, sweetheart?"

Anna took deep breaths. Surely Jeff wouldn't let this man truly touch her, as envious as he pretended to be. She screamed, noticing a knife in his hand.

"He won't cut you." Jeff explained, "She's afraid of her own shadow," he taunted, causing the stranger to chuckle.

Anna took ragged breaths as he slowly used the knife to cut away the fabric of her pants. He teased her skin with the blade before slicing through her panties. He ripped the material further, uncovering everything for his viewing, and in moments, her bare pussy was brought to light.

Anna whimpered, rocking from Jeff's tight hold, "Please, don't...."

Ray examined her folds, nodding in approval at his lucky brother. Her pussy was plump and pretty, and his cock pressed hard against his suit pants. Had she not been his brother's, he would have kissed the charmed clit perched in the middle of her warm slit. He smiled, plunging his finger inside her warmth.

"Umm, stop, stop, " she groaned, clenching her muscles to keep him out.

"Tight little pussy," he remarked, licking his lips.

"I told you," Jeff chuckled.

The stranger slid deeper and crept out. In moments sticky cream covered his finger.

"Damn," Ray smiled, "Do you get this wet for Daddy, sweet girl?"

Anna whimpered, and Ray continued to please her with his finger alternating between rubbing the wetness to the rim of her asshole and sliding up to her slowly growing clit. Her cunt doubled crossed her and spewed cream as he sought deeper, explicitly nudging at her A-spot.

"Mmm," she sighed, blinking back the craving to plunge into this minor pleasure.

"Should I use another finger? You've loosened up quite a bit for me, sweetheart," Ray asked.

Anna stayed silent, biting her lip in uncertainty. Her cream had come unwillingly, slathering down her ass crack. His second finger provided her pussy nurture, and she gasped in delight. Her pussy gripped his fingers, spitting out more hot cream.

"Uh, ooh..."

"You like to be fingered? Advise me, how many fingers can I use," he asked, removing his fingers and bringing them to her mouth.

"Come on, clean up your mess, dirty girl," Ray smiled.

Shaking her head, Anna kept her mouth closed. She had no problem tasting herself, but she did not want to suck his alien fingers.

Jeff hushedly weaved in her ear, "You want that 50 thousand, don't you?"

Money, this was all for money, she told herself as she opened her mouth to let the strange fingers in. She allowed him to push and survey her mouth, sliding his fingers against her tongue.

"Lick it up, pretty girl," Ray ordered with a dazzling smile, "How many fingers do you need to cum?"

"Answer him," Jeff urged with a kiss on her arm.

"Two," she whispered against his fingertips.

"That's a good girl." Ray inserted the two back in, rolling around for a while before circling the rim of her taut asshole.

"How many fingers can you take in your ass?" He asked.

"None."

"That's the wrong answer, Anna."

Ray smashed his thumb against her clit. It was satisfying, but she didn't want to moan in pleasure. Ray noted the involuntary movement. He could sense the oncoming orgasm about to slash through Anna's core.

Ray paused again.

Forgoing the pressure that had built up, Anna shook her head. She had been so close. She jerked when his wet fingers roamed over her stern, revealed clitoris. Each swab on her hard dot caused her now aching thighs to twitch around Jeff's stronghold.

Ray halted and grinned, "Do you need something in your ass, now?"

"Uh, No," Her sexual frustration caused her to blurt out the demand, with a ragged breath, "Just rub it."

Ray smiled as he rubbed her swollen, aroused lips, gradually moving up. Before he got to the engorged nub, he trailed back down to her tight back hole.

Anna grunted and jerked as she tried to shift her body down so his unskilful hand could scrape her clit. She nor her dripping cunt knew he was doing it on purpose.

Ray returned to teasing the hood of her clit, circling in a tease, "You like that, don't you, little Brat?"

Anna shook her head, feeling his fingertips bordering her rear. Ray's face turned grim before he reached up to grab her cheeks firmly.

"Now, I know you don't have marbles in your pretty head," he mocked, wiggling her face back and forth playfully, "Use your words. Or do you want me to stick this cock in your ass?"

"Mmm, no, ah," she moaned, her thighs shaking with anticipation as his fingers returned to her clit. "Don't stop, please. Please. Please."

"Is she begging for a cock in her ass?" Ray tauntingly asked Jeff.

"No!" Anna shouted.

Jeff chuckled while Ray popped his palm against her slit a few times, encouraging more moisture to spew from her creamy opening.

"God damnit, girl, you're a waterfall."

"Ahhm, uhm!" Anna blubbered as his fingers dug into her depth, searching for the switch to her fountain.

"You want to come on my fingers?"

"Ah, mmm hmm...."

"Use your words, dammit. Tell me what you want."

"Ah, yes, oh hmm, please. I want to cum, please."

Ray removed his fingers; his only reaction was the same smile that had once been attractive to Anna currently filled her with contempt. He chuckled, walking to the desk and returning with a small buttplug. He brought it to her lips. Inexperienced by the device, Anna willingly stuck it in her mouth with hopes it would fill her sticky cunt.

"I'm going to put this in your ass," Ray explained, "Then I'll rub that little clit."

Anna could care less about anything going into her ass, but her ears perked at the mention of reliving this agonizing tension. Eagerly she nodded.

Ray arched his brow, staring at her for a vocal reply.

"Come on, brat," he swatted her aroused clit twice, causing her breath to catch in her throat, "Use your words, little slut. Daddy hasn't taught you that by now?"

Jeff started his excuse, but Anna interrupted with a plea to end the tension, "Do it, please, please."

"Do what?" Ray asked, a taunting smile appearing on his handsome face.

"What you said," Anna urged.

"I can't recall what I said." Ray chuckled, holding the plug to her face, "Where do you want me to put this?"

"My ass...." Being vocal heightened her desire. She felt dirty as sin as she whispered the notion to the strange man.

Ray pretended to be confused, "So I need to put this...." He broke to orbit the device around her clit, "Where?"

Anna quaked with need while Jeff laughed at his brother's mock.

Ray pulled back onto her slippery folds. She now knew they were both playing her. She grew more angry and sexually frustrated.

"Stick it in my ass because I want to cum," she quickly snapped, causing the men to chuckle.

"Well, I'll be damn, the brat can form a sentence." Ray chuckled to his brother.

Ray slid the plug around her wet sticky slit. The silky motion caused the nerve ending to spasm with threat, but he shifted toward her sealed asshole. Her face twisted into a pout, "Do it. Please, do it."

"It?"

"Ugh, fuck you. Just make me cum," she aggressively ordered.

"Do not get snappy with me, Anna," he warned, "You need to learn discipline."

Anna furrowed her brows, "Fuck you."

They laughed, making her face turn beet red. She was humiliated at engaging so hard in her molestation. She wiggled her body in frustration.

"I hate you both," she whined.

"Be nice," Jeff whispered, dropping her to kiss her cheek.

The man paused in thought, but his thumb soon continued to gratify her swollen clit while he utilized his other hand to forcefully shove the tip of the thick plug into her ass. Her high-pitched whine echoed throughout the small office.

"No, Ow! No, It hurts."

"A little more," Ray soothed, brushing his fingers against her sensitive clit.

"Oh, God!" Anna wanted to stop, but the pain and pleasure duo was hard to battle. She braced herself as her asshole stretched to invite the alien object. Her nipples hardened to aching peaks while chill bumps formed on her arms. The tingles were unfamiliar, and the sensations were becoming too powerful.

"Ah, Oooh, ow...."

With one final push, her rectum pulled taut, clenching the small plug at the base.

"Ugh, I don't like it. Take it out," Anna whipped her head back and forth, but suddenly the initial discomfort settled, and Ray's thumb was back strumming against her clit. She moaned from the pleasure of her full ass and his thumbs' aggressive assault.

"Oh, aghh.." Eyes closed tight. Anna focused on the tingling feeling, then, in a flash, the pleasure ceased, and her anxiety increased.

"No, No, No, No, please, please," she begged, "Rub it, please."

Jeff snickered at her torture, his cock growing stiff against his suit pants.

"My little girl wants to cum," he laughed.

"Of course she does." Ray scoffed, then looked toward her, "You are a greedy little girl who wants pleasure with a little discipline. I want to see how well this little pussy can take cock," he smirked, brushing his sticky fingers against her chin.

Jeff lowered Anna to her feet, and her hands went down to relieve herself. She felt like crying when Ray popped her jaw.

"Get your ass over there."

Her legs were sore from the tension and uncomfortable position. She wobbled to the couch to take a seat.

"Bend over," Ray ruled, rolling a condom onto his long shaft and carefully adjusting the rubber. He planned to take his brother's girl hard. Upon hearing she was a hard-to-tame brat, he assured Jeff he was the best tamer he knew.

"No, I don't want to," Anna whispered, sitting awkwardly and reminded again of her full ass. She didn't know how to remove it and feared the earlier pain.

Ray roughly handled her petite body, twisting and jerking her around."You might pull that shit with him, but not me," he barked.

Anna felt powerless, and her eyes watered from the humiliation.

"Spread those cheeks and show me that full ass," he ordered with a hard spank.

"Go easy on her. She's tender-hearted," Jeff explained, sitting at his desk.

"Spoiled," Ray chuckled, then looked toward her trembling frame, "You've got your Daddy pussy whipped."

"Fuck you," Jeff rolled his eyes but wouldn't and couldn't deny his statement was correct.

Ray sat beside her on the couch, pulling her onto his lap to straddle with slight hostility. She was saddened, and he was delighted by her vulnerable state. Ray slowly pulled down the ripped uniform pants, exposing her sweeping hips and ass.

"This dick will make you feel better," he urged, kissing her forehead, "I know you want to cum."

Ray moved her hair out of her flushed face. It was hot to the touch. Her icy glare softened a bit when he kissed her warm cheeks. He massaged each cheek reverently while Anna gazed at him with uneasiness. She felt sick from his touches and sniffed at her running nose.

"Are you going to be a good girl for me?"

'No," Anna replied.

"I told you, she's a hard one to crack," Jeff commented.

The handsome stranger laughed, "No such thing."

He smiled and positioned her on his long cock.

"Oh, damn, let me in tight pussy," Ray mumbled, modifying her legs to push into the cushions, "Take it all. I know it's big."

Ray broke in gradually, having an appreciation for his earlier toying. His cock effortlessly found its way inside her wet inviting slit. He pushed up, filling her cavity with all of his length, and reared his head back in delight.

"Fuck. Hmm, come on, sweetheart," he instructed, kneading her ass cheeks in his strong hands, "Bounce that pretty brown ass on this white cock."

Anna remained still, and he grew angry at her unwillingness to submit. Snarling his lip, Ray rushed inside her, slapping her ass simultaneously. The sharp pain sent further apprehension to run throughout her body. His cock felt foreign while her clit scrubbed against his thick pubic hair. His hand reached around to remove the plug. She stayed still, sensing the stretching of her once-tight hole.

"Oww...."

Anna was fixed and unable to move from the foreign pressure, "Ooh, stoppp..." she grunted, digging her nails into his shoulder.

Ray attempted to move in and out, enjoying the pained expression donning her fresh face. With her hole repeatedly stretched, Anna squinted her eyes. He continued his semi-invasion of her ass, feeling the stream of creaminess that covered his dick.

"ow, stop," Anna whimpered, afraid to move and cause more pain. She couldn't understand why her pussy was leaking so much, but the pain outweighed the fullness of his cock.

"Does it feel good?" Ray asked with a grunt, pushing faster inside her dripping folds.

Anna could only whimper as the pain grew past her level of pleasure, "Uhm, stop.."

Ray grabbed her face, "Say yes, or I'll shove a bigger one in your ass."

"Uhh, hmm..."

"Stop playing with the plug and hurry up," Jeff ordered with annoyance from his office chair. He swore her whimpers may have been those of agony and stood up to investigate.

Jeff pulled her shoulder back and scanned her troubled expression as Ray bounced her up and down on his cock. His fingers hooked the back of her neck to look up at him.

"Tell Daddy how good my cock feels," Ray panted.

"Mm, Daddy," she whimpered.

"You are okay, little girl," His reassuring countenance calmed her.

Donning an adorable pout, Anna winced as his cock hit a particular zone. It felt good now that the ass play was over, but she felt nasty and used.

"Milk his cock, baby," Jeff smiled, leaning closer to her face, "Show him how you work those muscles for Daddy."

Under his protection and the spell of his eyes, Anna ground into his lap. Jeff's fingers grazed against her cheek. He had a thawing effect that the stranger lacked. In need to make it end, Anna held his shoulders, making her ass jump.

"Hmm...." she moaned, concentrating on utilizing her pussy.

Ray widened his eyes as she bounced hard, glaring at him with a temper. He tried to reach out to slow her, but his cock was being yanked by her tight cunt.

"Ah, Shit, slow...."

Jeff chuckled as he watched his brother succumb to his little girl's nature.

"Hm," Ray gave a ragged breath. His seed loaded the condom, and his confidence was gone.

"Finished already?" Jeff smirked.

Ray rubbed his face, "I won't lie. That is a good shot of pussy."

Slightly embarrassed by her stunt, Ray used both hands to smack her fleshy ass. His swats were so fierce Anna let out choppy breaths as the tears welled in her eyes.

"Stop being a crybaby," he teased with another swat to her ass.

"Stop. Get up," Jeff snorted toward Ray.

Anna stood, wiping the falling tears. Quickly Jeff sat down, pulling her toward him. She pouted while his arm encircled her waist, bringing her into his lap and piercing his lips against her cheek.

"Did he hurt you?"

Anna nodded, hoping to receive comfort, but instead, he lightly chuckled at her misery and veered his cock into her pussy.

"You're going to be okay, baby."

Letting her head fall, she adjusted to the thicker and more familiar cock inside her. She pictured herself on a tropical island, spending money she didn't have yet to ward off the negative emotions.

Jeff delighted in her tightness before clamping his fingers on her waist, "Ride me."