Simone's Assfucking Fantasy

Simone's Assfucking Fantasy: The Seduction of Cindy and Ryan

(All persons engaged in sexual activity in this story are over 18 years old. Any similarities between this story and real people are purely coincidental)

*For background to this story, please first read "Helping the Neighbor: Ch. 3."*

Before bed Simone Richards thought she would look through some files her late husband had stored in his study. She poked through the drawers for some time, sipping her nightcap of cognac, before returning to her bedroom down the long hallway. Halfway there, she stopped, hearing a low moan from the bedroom of her two new employees, Cindy and Ryan, who had started working at her small estate earlier that week. She tiptoed to the other side of the hallway until she was just outside their door. It was a big door with a large keyhole, which let sound and light through it. She could see the flicker of candlelight and hear that low moan. She quietly knelt down to put her eye at the keyhole. She drew in her breath at the sight of Ryan crouched behind Cindy, his erect penis sliding in and out of Cindy's asshole.

"Mmm, that's good baby, fuck my ass with that big hard cock," Cindy said softly, grunting as she thrust her ass back to meet Ryan's thick shaft, the sound of his thighs slapping against her asscheeks coming through the keyhole. Simone stared at the two of them fucking, Ryan ramming his cock into Cindy's ass while she rubbed her cunt and ground her tits into the bed.

"I'm going to cum soon," Ryan grunted, his thrusting becoming faster and harder.

Simone's hand snaked between her panties to find her own cunt dripping with moisture. She dipped two fingers into her pussy, fucking herself while she stared at Cindy and Ryan.

"I want you to cum, baby. Shoot your cum all over my ass," Cindy said, herself on the verge of orgasm. "I'm going to cum, too."

Cindy's hand frantically rubbed her clit just as Ryan pulled out and splattered her asshole with his first load, which dripped between her cheeks into her cunt to merge with Cindy's orgasm. With a groan, Ryan put his still spurting cock back into Cindy's ass as she thrust back to take it inside her again and milk it of his second load. He pushed his meat into her ass several more times before collapsing on top of her.

Simone covered her mouth as her own orgasm hit her, her pussy spasming in her hand, two fingers buried inside her. She hurried down the hall to her own bedroom, dizzy with excitement at seeing Cindy's ass fucked by Ryan's thick cock. She had never had anal sex, but had watched porn after her husband died, masturbating to videos of hard cocks reaming tight assholes, cum spurting into women's mouths and onto their tits. Seeing it live, in person, was incredibly exciting to Simone, who drifted off to sleep, thinking of Ryan's cock penetrating her, his cum coating her asshole as she rubbed her cunt to orgasm.

***

Cindy lay in bed, curled around Ryan, who had fallen asleep after a brief shower. Still tingling from her orgasm, from the feeling of getting fucked in the ass, Cindy thought back to how she had arrived at that moment.

She had met Ryan while visiting her best friend Stacy, who, though married, was having an intense sexual affair with Ryan while her husband was on an extended business trip. Stacy had told her that her husband was secretly taping her and Ryan having sex, that he had encouraged Ryan to seduce her in order to keep her from straying from the marriage. The three of them had had sex numerous times, shortly before Stacy's husband returned, each one a different scenario.

The first time she blew Ryan while Stacy licked his balls and asshole before his cum splattered her face and Stacy's tits. Another time Ryan fucked Stacy in the ass from behind while she knelt on the carpeted stairs, her nipples rubbing against the carpet while Ryan fucked her, Cindy licking her cunt to orgasm, Ryan's cum dripping between her asscheeks into her mouth. Then she had taken Stacy's dildo in her ass, bouncing up and down on it while Ryan lapped at her pussy.

Their final sex act convinced her that she loved anal sex. She had knelt on the stairs as Stacy had the night before, rubbing her tits against the carpet. Stacy ate her pussy while Ryan licked her asshole before slowly easing his bulbous head inside her, the first time she'd had a real cock in her ass. She was simultaneously eaten and fucked, an amazing combination that led her to have a series of intense orgasms, the second coming when she felt Ryan's cum splash against her asshole and slide down into her cunt and then his meat reenter her asshole while Stacy ate his cum out of her pussy It was the most exciting sex of her life.

With Stacy's husband returning, Cindy and Ryan decided to stay together. Stacy was happy for them, begging them to visit again as soon as her husband went off on another business trip. Somehow Ryan and Cindy had ended up at Simone Richards' estate, drawn to an ad that promised life in the countryside and an opportunity for them to do things they loved: cooking, gardening, landscaping hiking. Simone paid them a monthly salary and gave them free room and board, giving them a chance to save money for, she hoped, buying a home.

Cindy and Ryan grew to love working at Simone's estate. They got into a good rhythm, Ryan working on the extensive landscaping and gardens while Cindy kept the big house clean and full of fresh flowers Ryan cut for her. They traded off cooking meals for Simone, using vegetables from the garden and provisions they got in the nearby town, about a 5 minute drive. Simone was pretty easy-going and seemed happy with the work they did, especially their meals. The estate was very private, with a long driveway protected by an electronic gate. When Simone was away tending to business or shopping, they had free reign of the place.

Although they had just started working for Simone, they were enjoying their work, and their sex in this big bed. She just missed having another woman to join in. Perhaps they could seduce Simone, she thought, as she drifted off to sleep. Simone was older than they were, in her early 40s, but very fit and attractive. She had installed a gym and treadmill after her husband died and worked out regularly. She was thin, with medium sized breasts, and a really hot ass she had noticed when she was sunning herself at the pool. She found herself drawn to Simone, as she had been to Stacy. She wasn't a lesbian, but she loved eating pussy, and having her pussy eaten, especially with a cock in her ass. She'd talk to Ryan about seducing Mrs. Richards in the morning, perhaps while sucking his morning wood, she thought, as she drifted off to sleep....

***

Ryan woke up the next morning to find Cindy's mouth covering half of his penis, her hand stroking the other half. She was on her knees, her ass in the air, one hand stroking his shaft while she sucked the head of his thick cock, the other hand between her legs rubbing her pussy. She licked his head and trailed her tongue down his long shaft to his balls. Then she licked her way back up to his head, nibbling and gently sucking on it while stroking his meat.

She blew him for five minutes until she felt him stiffen and then release a big load of cum into her throat. She sucked down his first load and then pumped his cock for his second load, which coated her lips and face. He groaned as she swallowed his final stream of cum, moaning as she rubbed her cunt while finishing him off.

She moved up to kiss him on the lips, sharing his orgasm with him, then sat astride his face, planting her wet pussy in front of his mouth. Still recovering from his morning blowjob, Ryan's tongue snaked inside Cindy's juicy cunt, licking her moist hole and then her engorged clitoris. She ground her pussy onto his face while rubbing her tits, close to cumming from blowing him and rubbing her cunt at the same time. Soon she was writhing on top of his face, pressing her cunt harder against his tongue, now buried deep inside her wet hole. She bucked several times, fucking his tongue, then collapsed against him.

Simone woke up incredibly horny, thinking about viewing last night's assfucking through the keyhole, her live porn movie. She got on her hands and knees and imagined Ryan mounting her from behind, first his tongue coating her ass and cunt, then his big cock pressing through her tight asshole until it was buried deep inside her. Her hand snaked between her legs to rub her pussy, feeling its wetness.

She masturbated to the thought of being fucked in the ass while Cindy ate her from below, like she had thought about licking Cindy's cunt while Ryan's cock slid in and out of her ass last night. She had never tasted another woman's pussy, but Cindy's looked yummy last night. Simone rubbed her cunt harder now, imagining Ryan's cock spurting cum all over her asshole then pushing back inside her ass while Cindy ate his cum from her pussy She felt her orgasm build as she pressed two fingers into her wet hole. She moaned into her pillow as she came, her cunt contracting around her thrusting fingers.

She lay in bed for a moment, thinking about how incredible it was to have two orgasms in the space of 24 hours. Her husband had been older than she was, and their sex life had declined to a monthly fuck, hardly enough to satisfy her hunger. She hadn't had any sex for the five months since he died, and her desire had been slowly building. Now, with Cindy and Ryan living in her big house, she felt like she was ready to reclaim her sexual passion, dormant for so many years. How she would get to act on that desire for sex remained to be seen. Perhaps she could walk in on Ryan and Cindy while they were fucking. She would need to come up with a plan.

***

That morning, Cindy noticed Mrs. Richards following her movements as she prepared her breakfast in the kitchen. Simone sat at the table in the breakfast nook, which looked out over the garden. Her gaze shifted from Ryan weeding the garden to Cindy cooking her omelette, her apron covering her small, round ass.

"Did you two have a pleasant evening last night?" Simone finally said, staring at Cindy.

Simone was wearing cut-off shorts and a tight-fitting top, her tits pressing against the thin cotton fabric. She looked unusually sexy, Cindy thought, compared to her typical outfit.

"I did, thanks. Ryan and I just chilled out, watched a Netflix show and went to bed," Cindy responded, giving her boss a big smile. "How about you, Mrs. Richards?"

Simone looked up and down Cindy's body and smiled. "I had a very enjoyable evening, thanks. Call me Simone, please."

"Ok, thanks, I will," Cindy said, turning to finish her omelette. For some reason she imagined Simone staring at her ass as she cooked, aware that Simone had been looking at her in a different way.

Simone returned her gaze to Ryan working in the garden, the sweat already forming on his muscular body, now absent the t-shirt he had started with.

"It looks hot out there. Ryan's already taken off his shirt," Simone said, staring at his chest and biceps.

"Hmmm, you're right, it must be hot," Cindy said, putting the plate on the table.

"Yum, this looks really edible," Simone said, giving Cindy another smile, resisting the urge to lick her lips. "Thank you."

"Any time you want it, Mrs. Richards, I mean Simone," Cindy said, returning the smile before heading to the sink.

Sitting on the patio eating lunch Cindy told Ryan about Simone's odd, almost flirty behavior.

"What's up with that?" she asked.

"Probably nothing," Ryan said. "She's just getting used to having us around, feeling comfortable with us, I'm guessing."

"Maybe. I couldn't help think that she was checking me out. And then she was staring at you working in the garden, noticing that your shirt was off."

"I bet she's just feeling good, getting over her husband's death. Probably feeling a bit horny in the summer heat," Ryan said, rubbing Cindy's inner thigh. "Like I am."

"I guess," Cindy said with a laugh. "Maybe we'll fuck again tonight. I enjoyed that big cock last night. And this morning." Cindy's hand cupped Ryan's crotch, finding a bulge in his shorts.

"It's a date. When Simone goes to bed I'm going to have my way with you," Ryan said, stroking her thigh, his penis beginning to swell from Cindy's touch and the thought of fucking her tight ass again.

They both worked through the sweltering day, looking forward to unwinding after serving Simone her dinner. After cleaning up they said goodnight to Simone and headed upstairs. When they heard Simone's bedroom door close, they ate a gummy and took showers. When Cindy walked out of the bathroom, she saw Ryan sitting on the side of the bed, a pillow on the floor in front of him.

"Hmmm, I think I know what that pillow is for," Cindy said, walking toward Ryan, shedding her bathrobe, her tits swaying as she approached him. She dropped to her knees and took Ryan's penis in her hand. She began stroking it with her right hand while swirling her tongue around his sensitive tip. Her left hand drifted between her thighs, a a finger sliding between the lips of her pussy.

"I think this big cock needs to be inside me," Cindy said, pumping his meat. "I think it needs to be in my cunt right now." Cindy engulfed his cock in one long swallow before releasing it from her mouth. She stood up and lay on the bed, spreading her legs to expose her nearly hairless pussy.

Ryan lay between Cindy's legs and licked her inner thighs before plunging his tongue into her oozing cunt. He fucked her wet hole with his tongue while rubbing her clit with his thumb. Then he licked his way lower, down to her asshole, his tongue swirling around it, getting it ready for his meat. She loved getting fucked in the ass while she rubbed her cunt; she said she had the most intense orgasms that way.

Ryan then knelt next to Cindy's head, giving her access to his bulging cock. She licked the head and then slathered his shaft with her tongue. She sucked his fat pole while he rubbed her cunt.

"I need that big cock inside me," Cindy said again, pushing Ryan onto his back. She sat astride him, facing away from him, and put his throbbing meat into her juicy cunt. She rode him while he grabbed her ass and pulled her onto his cock, her hand rubbing her clit as he fucked her.

Lying in bed, Simone heard muffled sounds from down the hall. She crept down the hallway and lowered her face to the keyhole in Cindy's and Ryan's bedroom door, peering through it as she had the first night. She could see Cindy riding Ryan's cock, bouncing up and down on his big pole while she rubbed her clit. She hurried back to her bedroom to get her dildo and then returned to Cindy and Ryan's door. She took off her panties and eased the dildo into her pussy, sliding down on its thick shaft as she watched Cindy's cunt slide down onto Ryan's big cock. Simone stared at Ryan's cock going in and out of Cindy's wet hole, imagining it sliding in and out of her own cunt.

Ryan rubbed lube into Cindy's asshole, getting it ready for his fat cock. Cindy moaned as she felt Ryan's finger coating her asshole, her cunt still gripping his thick meat as she rode him. Then she placed the head of his penis against her asshole, and eased it past her tight ring. She grunted as she felt Ryan slide another inch into her asshole, and then another until his cock was buried in her ass.

"Yes, fuck me with that big cock," Cindy said, groaning as she began pushing her ass onto Ryan's meat, matching his thrusts, her right hand now rubbing her cunt.

Simone watched Cindy and Ryan fuck, turned on by the sight of Ryan's cock disappearing into Cindy's asshole and at the sight of Cindy's open cunt, glistening with her juices. She wished she was on their bed right now, eating Cindy's juicy hole while she bobbed up and down on Ryan's meat. Simone rubbed saliva on her asshole and then eased the thin dildo into her ass, imagining it was Ryan's cock.

"I'm going to cum," Cindy said softly, loud enough for Simone to hear through the keyhole. She bucked twice on Ryan's cock before collapsing against his chest. Simone watched as Ryan kept sliding his cock in and out of Cindy's asshole before he grunted twice and then pulled his cock out of her hole, his first load reaching her tits, his second showering her stomach. His cum slid between her tits down to her cunt as he put his still spurting cock back into her ass, Cindy's hand still rubbing her cum-covered pussy.

Simone began to furiously rub her cunt as she slid her ass up and down on her fake cock, watching Ryan shoot his cum onto Cindy's tits and then slide his cock back into her asshole to deposit another load. She came in waves, stifling a moan with her left hand as he right hand kept rubbing her clit. She hurried down the hallway to her bedroom. 'Jesus,' Simone thought as she recovered from another intense orgasm. 'They are so fucking horny. I need some of that real cock.' She hatched a plan to get them both in her bed for what she hoped would be her first assfucking.

***

The next afternoon, Cindy looked out the kitchen window to see her boss sitting by the pool rubbing suntan lotion on herself. Thinking about her reverie of getting Mrs. Richards into their bed, and of Ryan's excitement at the idea after she had given him a morning blowjob, she hurried out to the pool with a glass of lemonade.

"Hi Simone, I saw you out here and thought you might like a cool drink," Cindy said, eyeing Simone's tan, lithe body, her breasts swelling against her tight bikini top.

"That's very sweet, thanks Cindy," Mrs. Richards said, noticing Cindy's eyes examining her body.

"Would you mind rubbing some lotion on my back," Simone said, handing her the bottle.

"Of course, any time," Cindy said with a smile, her pussy beginning to tingle at the thought of touching Simone's hot body.

Simone felt her own pussy begin to ache as she stared at Cindy's body, remembering her erotic scenarios that had dominated her thoughts the past two days: eating Cindy while Ryan fucked her in the ass; Cindy eating her while Ryan pounded her cunt. It was a hot day and Cindy was wearing cutoff jeans and a tank top that showed her nipples straining through the thin cotton material.

Simone lay flat on her lounge chair after taking off her bikini top. Cindy began rubbing oil on Simone's neck and back, slowly moving down to her asscheeks.

"Yes, if you don't mind rubbing some on my butt and legs that would be great," Simone said, her mound beginning to rub against the chair as she felt Cindy's hands massage her back.

"So, how did you and Ryan meet," she asked.

Cindy rubbed oil into Simone's back and butt as she told her the story of visiting Stacy and meeting Ryan.

"And we spent a lot of time together, and..." Cindy hesitated halfway through her story.

"And?" Simone asked."And... we had a lot of fun together, the three of us," Cindy said, finally, as her hands roamed over Simone's tight ass, just a sliver of the bikini thong pressed against her asshole, and then down to her thighs.

Simone spread her legs to give Cindy access to her inner thighs, which Cindy rubbed oil into, her fingers an inch from Simone's slit.

"Hmmm, that does sound like fun," Simone said, her nipples now straining against the lounge chair as she imagined Ryan, Cindy, and Stacy together in bed.

"It really was. And then Stacy's husband came home and Ryan and I decided to stay together. And here we are," Cindy said, her hands now rubbing oil into Simone's calves. "And we're very happy to be here, Mrs. Richards, I mean Simone."

"And I'm glad you're here," Simone said, turning over to give Cindy a big smile and get a sip of her drink, exposing her tits to her as she did.

She followed Cindy's eyes to her tits as she turned back onto her stomach. "Thank you for oiling me up, Cindy.""Any time, Simone. Is there anything else I can do for you," Cindy asked, getting up to leave. She stared at Simone's ass one more time, her pussy throbbing at the sight, wanting to rip off her thong and bury her tongue in her ass and cunt.