Jolene's First Double Penetration

Started by Kendra Massive · 0 Replies
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Kendra Massive


12 months ago

Posted: 3 months ago
Jolene's petite body stiffened as she heard the knock on her door. What had started as a shared fantasy between and her boyfriend was suddenly becoming very real. Her ex, Matt, was outside, and she and Craig were snuggled up on the couch.

"Aren't you going to answer it?" he asked. Jolene stood up, pulled her dress down and readjusted the bra over her recently augmented C-cup breasts. At barely 5' tall and just over 100 gym-toned pounds, the brunette's small frame left no doubt as to their lack of authenticity. Even at 54 years old, many men half her age were keen to gain carnal knowledge, and she seldom had to buy her own drinks when she was out dancing with her girlfriends.

Jolene hesitated before approaching her front door. She and Craig had been dating for almost a year, and they had often playfully discussed the fantasy of a threesome. Their favorite bedroom activity consisted of anal sex and a toy in her pussy while passionately discussing the many group sex porns they had watched together. Only two men had ever been in her ass, and both were about to be in her living room.

Craig was a tall, blonde distinguished older gentleman who frequented the same gym as Jolene. What started as casual conversation and an invitation for drinks, had led to a few dates and eventually a long-term relationship. He was a secure business owner while Matt was an unstable musician who did odd jobs while pursuing his dream. The sex with her ex was amazing and her current boyfriend knew it.

"Hi, Matt," she greeted, and invited him in. Their esteemed guest had shown up in skinny jeans, Chuck Taylors, and a concert t shirt. Matt grinned as he admired her attire for the evening. Jolene wore a tight, black, one-piece dress which ended scandalously high above her knees. While admiring her from top down, he paused at her ample cleavage before moving down past her flat tummy, and delighting in her black, thigh-high stockings and high heels. They hugged briefly before he followed her into the living room.

The three exchanged pleasantries before Jolene sauntered off into the kitchen to prepare drinks. Upon returning with three vodka and sodas, she was startled to see that Matt had emptied a sizable pile of cocaine on her coffee table, and the two men were busying themselves chopping up lines.

"Ladies first," Matt suggested as he handed her a rolled-up bill. Jolene reluctantly accepted. The suggestively dressed brunette sat between them, leaned forward and snorted the first of many lines that evening. After a few rounds of bumps, they sat back, casually conversed, enjoying their drinks. The hosts had consumed several cocktails before their guest arrived, and Jolene's head was spinning in pleasant, euphoric anticipation.

Matt's escalated the erotic tension by placing his hand on her inner thigh. Craig observed this, brushed her hair back, and pressed his lips against the nape of her neck. Matt's hand slid higher up under her dress, and he was pleased to discover that she had decided against wearing panties. Jolene moaned as his finger probed her shaved pussy before sliding inside her. She leaned to her left and opened her mouth to meet Craig's. Their tongues intertwined as he squeezed her beautiful fake tits. Matt slid a second finger inside her.

Jolene's thoughts were blurring as the two men's hands and mouths became more aggressive in their exploration of her body. Her little black dress afforded little defense as they reached inside and underneath to fondle her breasts and squeeze her engorged nipples. Her legs spread subconsciously to allow more access to her pussy as she alternated kissing the men on either side of her.

"Another line?" Matt suggested as he broke their passionate embrace. He handed the dollar to her which she readily accepted, and a line shot up each nostril. Afterwards, Jolene broke free and went back to the kitchen to replenish their drinks. Matt and Craig exchanged sinister glances as they imbibed at the table.

When she returned and placed their glasses on the table, Matt stood up and pulled her to him. As she surrendered to his embrace, his hands slid up the back of her stocking-clad thighs and under her dress, squeezing her firm, naked ass. His tongue met hers as Craig took his place behind her, wrapping his arms around her delicate waist. In her drug and alcohol fueled state, she was vaguely aware of her dress being pulled upward, exposing her pussy and ass.

"Uhhhhhhhhmmmm," she moaned as Matt's fingers reached between her legs and massaged her throbbing clitoris. Her arms instinctively rose as her flimsy dress was pulled over her head. Craig unhooked the clasp of her lacey black bra, allowing it to fall over her arms to the floor. Jolene was now completely exposed, wearing only stockings and high heels as her lovers mauled her naked body. Hands, lips, tongues, and teeth sampled her flesh.

Suddenly aware of her lone nakedness, she reached down and pulled at Matt's belt, button, and zipper. Once his pants and underwear were pushed down, Jolene watched as his magnificent, thick, nine-inch cock sprang upwards. Her eyes met his as she gripped it and started stroking. She heard pants being undone and removed behind her before Craig's strong hands pressed against her shoulders and directed her to her knees. Two thick, hard cocks were now inches from her face.

"Which one you gonna suck first, bitch?" Matt always knew what she liked to hear. Jolene wrapped her fingers around both of their cocks.

"Who wants it first?" she asked, looking upwards and seductively smiling.

"Well, Matt's our guest," Craig answered. Jolene accepted this gesture of hospitality, leaned towards Matt's cock, and circled the head with her tongue.

"You remember my mouth?" she teased. Matt responded by grabbing two fistfuls of her hair and shoving his thick shaft to the back of her throat. Jolene gagged and attempted to pull away, but Matt held her head in place, relishing in her discomfort, before he began to aggressively fuck her face. Thick globs of saliva dripped out of her mouth, down her chin, and coated his balls.

"You remember my cock?" he hissed, increasing the intensity of his thrusts while Craig looked on. Jolene could only grunt in affirmation. After several moments of loud, sloppy throat fucking, she pushed her hands against his thighs and he finally released her. Craig saw his opportunity, pulled her head towards his cock, and mimicked Matt's actions. Jolene endured until a lack of oxygen gave her the panicked strength to break away. She was allowed a few breaths before her ex yanked her hair and pulled her face back to his crotch. The men took turns fucking her mouth, increasing their intensity, and becoming more vocal in their degradation.

"Suck it, bitch!"

"Choke that whore!"

"Fuck her in the ass yet?" Matt asked.

"This slut loves it," was the reply. The men laughed out loud at this shared knowledge. Jolene came to the realization that her expectation of a passionate threesome where she was to be the exalted center of attention was unlikely to occur. Matt and Craig viewed her as a filthy slut, and they were bonding over their shared humiliation of her.

The drugs, alcohol, and asphyxiation were causing her mind to drift from the reality of the current situation and to the realm of fantasy. Jolene was a unique female in that she truly enjoyed pornography, whether by herself or with a lover. Her favorite scenes usually involved a delicate young starlet and two or more sadistic men treating her like a worthless slut. She especially loved when they would have the girl sandwiched between them, driving their gigantic cocks into her pussy and ass, while the camera zoomed in on her face's pained expression as she was undoubtedly regretting her life's decisions.

Jolene's pussy dripped with the realization that she was that girl while Matt and Craig continued to take turns forcing their cocks down her throat. Mascara was running down her cheeks, and her hair, which she had meticulously styled for the evening, was a tangled mess. Her flawless tits were becoming increasingly bruised and her perky little ass was bright red. Thick streams of drool had accumulated on her torso and thighs, running down to her brush-burned knees. Matt grabbed her hair, and instead of using her mouth, had her crawl on her hands and knees to the coffee table and the waiting narcotics.

Jolene heard pants being removed behind her as she leaned down to inhale another line. Her already racing heart accelerated when she felt a pair of hands grab her hips and a cock pressed at the opening of her dripping cunt. She sniffed and then let out an animalistic grunt as the entire shaft was driven into her body. Looking back, she saw that Matt was the one fucking her. Turning her head, she observed Craig seated on the couch stroking his erection.

"Do another one," Matt commanded as he briefly paused his thrusting. Jolene's pussy was still adjusting to his cock as she obeyed his order. Her thoughts were blurring with depraved lust, as she welcomed her situation. While she had had several partners since her divorce five years ago, including a few one-night stands, nothing would compare to what awaited her tonight. Even her vacation in Vegas, where through the course of a week, she ended up in the rooms of four separate gentlemen wasn't as filthy as this. Jolene's mind wandered as she remembered how she had irresponsibly insisted against condoms. Four strangers gleefully unloaded their seed into her welcoming pussy that that week. She had even, during a trip to Jamaica, invited a local man half her age back to her room. Jolene's lust intensified as she thought back to his enormous black cock driving into her little white pussy before dumping his load in her. Still, nothing in her sexual past compared to this.

Matt resumed his thrusting, his pelvis smacking against her ass with increasing force. Jolene was in ecstasy as she felt the drugs and booze circulate through her bloodstream while her favorite cock drove deeper into her pussy. The tingling in her belly rapidly spread to the rest of her body. Every muscle contracted as she erupted in orgasmic bliss.

Her moans of satisfaction confirmed her consent for the evening's activities, and both men knew that she was theirs to be used. Eventually the two men lifted her onto the couch with her head positioned at Craig's cock, and Matt behind her. Jolene struggled to keep her mouth on her current boyfriend's dick as she was pounded from behind. Craig assisted by grabbing two fistfuls of hair and keeping her head in place. The abused MILF submitted as they manhandled her into different positions and took turns fucking her pussy and mouth.

Jolene loved that they were in control of her, and that her petite body was theirs. While she was in a relationship with Craig, she preferred being a whore. Whether it was a business trip, vacation, or a night out with the girls, her ultimate desire was to find a handsome stranger to fuck. Sadly, most weren't intuitive enough to realize that she didn't want to be treated like a lady. She wanted to be abused like a fucking slut! Craig, and especially Matt, knew this, and continued to escalate their delightful mistreatment of her, smacking, spanking, choking, biting, and degrading her.

"I think the coke slut wants another line before we fuck her ass," said Matt. Craig smiled in agreement before withdrawing from her pussy and motioning towards the coffee table. Jolene struggled to position herself in a seated position on the couch. Multiple orgasms, intoxication, and abuse had diminished her mobility. As she reached for the dollar, Matt snatched it away.

"What are you doing?" she slurred, and then watched as he kneeled down and pressed the tip of his cock, glistening with her spit and pussy juice, onto a line, encrusting his glans with white powder. He proceeded to slide the table away before grabbing her hair and forcing her to her knees before sitting back on the couch and pulling her to face him.

"You want more blow? Then suck it off my cock, bitch," he demanded. Naked and bruised, she wrapped her fingers around Matt's garnished dick, brought her tongue to the head, and made sensual eye contact as she licked. Craig, inspired by this, wandered over to the table to affix a line to his cock before returning to the couch. Jolene reached for her drink before sliding over to her boyfriend and repeating the vile act.

Jolene's mouth went numb as this foul method of ingestion polluted her bloodstream. A new rush of arousal and chemical euphoria took over with this depravity. Her pussy began to overflow, and juices began trickling down her inner thighs at the realization that she was on her knees, wearing only stockings and heels, and eagerly sucking cocaine off their dicks.

Jolene giggled as she felt Matt's tongue swirl around her ticklish asshole and continued sucking Craig as her ex positioned himself behind her, placing his cock against her anus. His slippery dick missed its target on the first few attempts, but once the head made penetration, he grabbed her hips and drove his full length inside her.

Jolene cried out at his cruelty and tried to pull away, but four hands held her in place as her mouth and ass were filled. Craig's fingers were intertwined in her hair as Matt's dug into her hips. They laughed and jeered as her tiny body hopelessly struggled against the combined strength of two men. Matt withdrew all but the head of his cock and then slammed his hips against her. Jolene shrieked and tears ran down her cheeks. Craig yanked her head back as he leaned down to face her.

"Where's his cock, bitch?"

"In my ass," she managed to reply. Her boyfriend, satisfied with her reply, sloppily kissed her before pushing her head back into his crotch. Jolene cries of agony gradually subsided and became moans of pleasure as her soft inner tissue stretched to accommodate the cock buried in her ass.

Her belly burned with lust as she hazily began to embrace the moment. What had begun as dirty fantasy was now coming to fruition. Here she was, drunk, out of her mind on blow, getting fucked in the ass while giving head. Involuntarily, she pushed her body back to meet the advances of her sodomizer. Jolene moaned with pleasure with every slap on her ass or harsh twist of her nipples.

"I want you both inside of me," she managed to gasp. Both men were happy to oblige. Matt withdrew, and Craig pulled her on top of him. Jolene reached between her legs and directed his cock toward her obscenely wet pussy. Her former boyfriend watched as she lowered herself onto Craig's lap, engulfing him.

After doing another line, Matt took his place behind Jolene's bruised and crimson ass and configured his legs amongst theirs. His left hand pressed against her tailbone to stop her motion as his other hand guided the tip of his cock to her asshole. Craig reached behind her to spread her ass as Matt applied pressure. Jolene's petite body offered resistance as the two cocks fought to occupy her tight little holes.

"AAAAARRRRGGGGHHHHUUUUUNNNNGGGGHHH!" screamed Jolene as she felt her ass give way. Her body writhed and her legs kicked as she tried to squirm away, but the two strong men held her little body in place. Jolene began to panic as her holes stretched to accommodate the two thick cocks in her crotch. Matt grunted as he forced the last inch inside of her.

"How's that, you dirty bitch?" he taunted.

"I can't do it! Please!" she begged.

"You'll do what I want," commanded Craig as he looked up at her disheveled face. Both men laughed as they began to thrust in and out of her; Slowly at first but increasing in intensity as they tore through the piece of meat between them. Her pleas for mercy were met with increasing ferocity as they drove deeper and deeper inside of her.

In her state of agony and intoxication, she began to imagine herself on the set of a pornographic movie. She was dressed for the part, after all, wasn't she? Black lace stockings and heels complimented by a bouncing set of fake tits. Jolene envisioned a camera man zooming in on her crotch as two dicks fucked her pussy and asshole. Maybe she could be a hopeful actress who had moved to California, but got addicted to drugs, and turned to porn?

"That's it guys. Fuck her good," she could hear the director saying, despite her howls of pain.

"Please stop! It hurts! I can't do it!" she heard herself begging.

"You need the money, don't you, bitch?" the director would ask. She would only nod and whimper in affirmation, knowing how low she had sunk, and imagining what her friends and family will think when they find out.

"Then smile at the camera and tell me what a filthy slut you are. Next week's scene you're gonna get gangbanged by TEN guys," he'd jeer, eliciting mocking laughter from everyone on the set. With a sense of hopelessness, she'd follow his direction, let her body be used, and hope it'd be over soon.

This fantasy caused her to smile as Craig and Matt abused her soft inner tissue. Vitriol flowed from their mouths while they pulled her hair, mauled her breasts, and smacked her ass. Jolene felt a familiar sensation in her belly building causing her to push back to as they pounded her. The room was filled with animalistic grunts and the obscene sounds of slick penetration. Harder and harder they went until her body went rigid with spasms of orgasmic bliss.

Matt was quick to respond to her climax, increasing the ferocity of his thrusts. Jolene felt his cock begin to swell, stretching her hole even further and achieving greater depths. Sobbing, she buried her face in Craig's shoulder. Her boyfriend responded with taunting laughter and pushed her hips downward until he was pressing against her cervix. Jolene went limp as they fought for space in her crotch.

Faster and faster he went until he groaned with delight, drove forward one last time, and emptied spurt after spurt of white hot cum deep inside her bowels.

Jolene whimpered as her ex collapsed on her back. Once his breathing slowed, he whispered in her ear.

"You are a filthy nasty whore, aren't you?" Jolene nodded in agreement as his shrinking cock mercifully slipped out of her ravaged asshole and a stream of cum dripped down onto the rigid shaft still in her pussy. Matt stood up and Craig pushed her off, leaving her kneeling on the floor in front of him.

"Clean me off," her boyfriend ordered. Jolene grimaced at the glistening cock standing inches from her face. Regret creeped into her psyche as her drug-fueled mind attempted to grasp the situation. Jolene looked up him pleadingly and shook her head back and forth. Craig sneered at her and grabbed two handfuls of her hair. She yelped as Matt landed a hard slap on her bruised ass.

"Do as he says!" he commanded.

Jolene submitted and allowed her head to be pulled downwards. She had never sucked a cock after fucking her ass, but now she was expected to taste cum that had **** out of it. Reluctantly, she stuck out her tongue and lapped at the base of her boyfriend's shaft.

Matt kneeled at the opposite side of the coffee table, snorted another line, and leaned back to enjoy the show. He especially enjoyed the sight of her crimson ass, distended asshole, and the stream of cum leaking over her pussy and running down her inner thighs. His cocked twitched and began to harden again.

Craig gradually became more aggressive while fucking Jolene's mouth, causing her to gag and drool. A stream of obscenities accompanied this abuse. She struggled to breath and her hands pushed against his thighs. Then suddenly he stood up, pushed her face into the couch and took his place behind her. The intoxicated fuck toy reached her hand back between her legs and spread her pussy. Instead, he placed the head of his cock against her swollen and cum-filled anus.

"No! Please!" she begged, reaching back with her other hand and pushing against his hip. Craig grabbed her wrist, twisted her arm behind her back, held her in place, and pushed forward. Jolene cried out as her anus gave way and continued to plead as he forced the entire length into her cum-lubricated rectum. Matt laughed from his vantage point while stroking his growing cock.

Craig increased his pace as his hips pounded against his disgraced girlfriend. Jolene looked back over her shoulder and was startled by the twisted look of aggression on her boyfriend's face. Another look further back revealed the offensive grin of her ex. Jolene's entire body tensed with each cruel thrust, yet her free hand was still between her legs, playing with her pussy. The fingers in her cunt felt his cock through the thin membrane.

"Is that all you got?" she jeered. This elicited surprised laughter from their observer, and an increasingly angry intensity from Craig. One hand released her wrist and dug into her hip. The other grabber her hair, arching her backwards while he sadistically drove deeper and more forcefully inside her.

"Harder!" she ordered, feeling an orgasm building. Craig responded, savagely fucking her ass with all the force he could deliver. Sweat dripped off their bodies as they locked into this sexual battle of wills. Matt sipped his drink with one hand. The other jerked his fully erect cock while he looked on at the perverse spectacle.

A low groan began emanating from Craig that transformed into a howl of ecstasy. He drove forward one last time, and Jolene felt his cock spasm as he emptied his balls, pumping the second gooey load of the evening deep in her ass. Craig collapsed backward and proceeded to lay gasping on the floor. Jolene, frustrated by the closeness of her orgasm, looked back at her previous lover and his hard cock.

"You got something left for me, baby?" she cooed. Matt needed no further encouragement, and quickly took his place behind her. Craig could only look on as Jolene's ex-boyfriend playfully alternated between pressing his cock against her pussy and her ruined and leaking asshole.

"Ass," she directed. Matt complied and sank his cock into her well-fucked and cum-filled anus. Jolene moaned in ecstasy and reached between her legs to play with her engorged clitoris. Sloppy sounds of penetration filled the room as a steady rhythm developed. Cum coated his cock and **** down over her pussy, fingers, and inner thighs.

"I always loved your cock in my ass," she confessed, as Craig looked on with jealousy and anguish. These feeling increased with the pitch of her moans, and he knew her orgasm was close. Matt's groans increased with hers, and suddenly, Craig was witness as the two came in unison. Jolene thrashed and screamed as Matt grunted and filled her ass with the third load of the night.

The three sat silently for a few minutes before Jolene excused herself to go to the bathroom. Matt searched for his discarded clothes and began dressing. Craig got up and walked to the kitchen sink to clean up. Jolene returned wearing a bathrobe, and the trio conversed while they finished their drinks and snorted the remaining cocaine on the table.

Eventually, Matt announced his intentions to leave. He and a still-naked Craig exchanged an uncomfortable handshake before he turned his attention to Jolene. They engaged in an amorous kiss while her boyfriend looked on. Soon after, the door closed behind him.

"I think I need another drink," announced Jolene. "Do you want another?" Craig nodded in affirmation. Upon returning, she placed the drinks on the table. Her boyfriend stood before her, pushed her robe off her shoulder, and watched it fall to the floor. Her naked body spoke to the events of the evening. Bite marks and bruises covered her tits. Her tangled hair reached down towards her red and purple ass cheeks. Her cursory attempts at clean up hadn't completely removed her running eye liner or smeared lipstick. The sight of his beautiful, but now ruined and discarded girlfriend aroused him. He motioned down to his hardening cock.

"You wanna take these drinks to bed?" he asked.

Jolene smiled in agreement, took his hand, and the two walked towards their bedroom.

"Not my ass though..."
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