Anniversary Fling Pt. 05

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Jill takes her final slut-wife exam.
9.5k words
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Part 5 of the 5 part series

Updated 08/26/2023
Created 04/24/2023
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CaseyBea
CaseyBea
1,360 Followers

[All characters are 18 years or older.]

Anniversary Fling - Part-4

A sexy wife gets a free pass as an anniversary gift

Erotic Fiction

by

Casey Bea

Part-5

Jill takes her final slut-wife exam

(A short recap from part-4)

"I've taken the liberty of setting up a little fantasy scenario to test your willingness to support your husband in any way that you can," Sandy went on. "We'll call it your final exam before earning your slut-wife master's degree."

"What kind of scenario?" Jill asked as her pussy tingled.

"Jay has an annual review coming up at work, and you decide to go in and see if you can influence his boss to give him a big raise," Sandy explained. "The resort is used to accommodating fantasy requests so I've arranged an office setting and someone from the resort staff to play your hubby's boss."

"Not you two?" Jill replied. She knew that she would be more comfortable, more relaxed with Sandy and Reed, but the thought of engaging in Sandy's final-exam fantasy with a perfect stranger made her pussy leak. She was really getting into this slut-wife stuff!

"We'll be watching," Sandy answered. "And grading you," she added with a chuckle. "In fact, anyone at the resort who cares to cough up the pay-per-view charge will be watching you. Doing fantasies like this with the help of the staff isn't part of the regular package, but if the participants are willing to have their fantasy broadcast over the resort's closed-circuit system, then the resort will waive the fee. Are you willing?"

Over the past day and a half, Jill had gone from being embarrassed to show her privates in public to being comfortable with strangers watching her give a blowjob to being a full-fledged exhibitionist and getting more aroused with the more people who were watching. It made her pussy buzz when a woman stopped by at the pool, and told her, "My boyfriend and I were outside your bungalow earlier and watched you fuck your friend's ass, then get yours fucked. Both of us jerked off and we're getting a strap-on for later on so I can fuck his ass tonight. Thank you for the great show!"

"Hell, yes, I'm willing!" Jill answered Sandy.

(Part-5)

Sandy sorted through the clothes that Jill had brought with her and had her dress the part of a loving, supportive wife wearing slacks and a v-neck pullover blouse. Jill was a little surprised at her mentor's choice of conservative clothing; after all, she was pretending to be going to her husband's workplace to use her slut training to get him a raise.

Sandy gave her a tight hug and a warm kiss before sending her on her way. "Good luck!" she said. She crooked her thumb toward the big-screen TV and added, "We'll be watching; make us proud! And make everyone else who's watching horny!"

Jill walked to the resort's administration building and as Sandy had instructed her, she told the curvy black woman at the reception desk, "Hi, I'm Jill Smith. I have an appointment with Mr. Holden."

The woman pressed a button on her intercom, and said, "Mrs. Smith is here for you."

"Ah, yes," a male voice replied. "Show her in please."

The woman stood up and Jill saw that her curviness continued below her chest. She had a narrow waist and wore a tight, short skirt that hugged her bubble butt and her thighs. Jill wished that she was playing the part of her husband's boss!

"Hello, Jill," Mr. Holden said as she entered his office and he came around from behind his desk. "Come in, come in."

Jill was a little surprised that the room appeared to be an actual working office, not a set to act out a fantasy. Then she noticed what looked like security cameras in the corners near the ceiling and it made perfect sense to her that the resort would use their existing facilities to do double-duty.

In fact, there were eight cameras around the office, some less obvious than others but all being monitored and controlled by a video technician in another room. He could zoom, tilt, and pan any of the cameras and switch their feeds to the closed-circuit pay-per-view system throughout the resort producing a live-action porn movie on the fly. It was also being recorded for Jill to take with her.

Mr. Holden offered Jill a seat in an upholstered guest chair, and as she sat, he said, "It's nice to see you again, Jill. You might remember that we met at the Christmas party last year. That gown you were wearing was stunning!"

Jill was surprised at Mr. Holden's level of acting. She hoped that she could do as well.

"Thank you!" she replied. "That was a fun evening. I enjoyed dancing with you."

He smiled at her ability to ad-lib, and asked, "So, what is it that brings you here today?"

"Well, Mr. Holden..."

"Call me Ron," he interrupted her. "Please."

"Well, Ron, my husband, Jay, has a review coming up, and I thought that... well, maybe if I dropped by and talked to you in private that... well, maybe I could ensure that he got the big raise that he deserves."

"I see," he said he said as he moved to lean against his desk directly in front of her. "I've always been a believer in direct negotiations, but you realize, of course, that actions speak far louder than words."

She leaned forward in her chair, took hold of his fly, and slowly pulled it down as she replied, "You mean actions like this?"

"Exactly!" he replied.

He wore pleated-front dress slacks and no underwear so it was easy for Jill to reach in and take hold of his dick. She was surprised that it was completely flaccid while her pussy was tingling and wet at the prospect of what she was about to do with a total stranger. That was certainly a blow to her ego. As a fantasy-fulfilling actor with the resort perhaps he had had so many gorgeous and buxom women that her mousy, plane-Pattye looks and petite figure didn't arouse him. Well, screw that! she said to herself, confident that her newly-acquired talents would more than make up for her small boobs and taking it as a challenge.

She used both hands to work his flexible penis and his testicles out through his fly, and then as she gently massaged his balls she took his pecker in her mouth all the way down to its root and pushed it around with her tongue. She liked the playful feel of a squishy, flaccid dick in her mouth but with Jay, it had always come after having sex; she had never had to do anything more than give him a sexy smile to get him hard. Despite the slap to her ego, she was finding this challenge to be fun.

With her lips tightened snuggly around his shaven root, she drew a hard suction and then pulled back, sliding her lips along his squishy shaft while she tickled his knob with her tongue. She withdrew until her lips were locked around his dick's neck and she had his pecker pulled out straight. Almost immediately, the unimpressive penis began to inflate, and in a matter of seconds it was a very respectable full-fledged cock. It was a wonderful stroke to her ego, but she wasn't done yet.

She swirled her tongue over his cock-head making sure it was wet and slippery, and then with a snug grip on his balls, she leaned forward and shoved his cock down her throat in one push. She nuzzled her lips against his root and then stuck out her tongue and licked his balls as she pushed them up.

"Holy shit!" he groaned, and Jill was quite sure it wasn't acting. That was what her ego was looking for!

She pulled back until his glistening knob was just touching her lips, flicked its pee-hole with her tongue, and then drove forward giving him another deep-throat. This time he groaned and put his hand on the back of her head, forcing her face into his open fly and holding her there. "Well, well, Mrs. Smith," he said as he rocked his hips getting another half-inch of his cock down her throat, "you certainly are a devoted wife, aren't you? Jay is a very lucky man." He let go of her head, and added, "Please continue with your negotiations on his behalf."

As she fondled his balls she began giving him a sucking, bobbing blowjob interspersed with slippery jerk-offs lubricated with her throat-slime. His moans and groans were very rewarding and had her pussy humming and leaking to the point where she was about to suggest that he fuck her.

But just before she spoke, he reached back and picked up his phone from the desk. With one hand on her head, he kept her bobbing up and down his cock while he spoke into the phone.

"Hi, Patty. Hey, I'm in the middle of negotiating a raise for Jay Smith, and it occurs to me that somebody from HR should be in on this, too. Do you have time to step in here and join us?"

As Ron pulled on her head, spearing his cock down her throat again, Jill suddenly recalled the nameplate on the desk of the curvy black woman who had shown her in. It read Patty Moore, HR Director. Her pussy began tingling so much that she wanted to reach between her legs and rub it through her pants but she forced herself to resist.

Ron listened at the phone for a moment, and then replied, "You're right. His supervisor and his shift manager should probably be involved, too. See if they're available to join us."

Jill let out a moan around the boner that was filling her throat. She had fully expected that this fantasy that Sandy had concocted was going to be only with her "husband's boss." The thought of negotiating his raise with four people--at least one of whom was another woman--lit her pussy on fire.

A few moments later, Patty walked into the office and stood next to Ron as he bobbed Jill's mouth up and down his dick. He pulled her all the way in for a full-depth throat-fuck, and Patty said, "My, my! Jay's little wifey appears to be quite the negotiator."

With her lips pressed inside Ron's fly, Jill rotated her eyes toward Patty as best she could and could see that she was unbuttoning her blouse. When Ron pulled her head back, leaving just his dick-head in her mouth, she was able to get a better look and watched as the HR Director pulled open her blouse to reveal a set of big, black boobs supported by a shelf-bra that left their massive nipples fully exposed.

Patty's skin color was dark, but her nipples were almost jet-black. They were at least two inches in diameter and had swollen nubs protruding that were at least the size of Jill's little finger down to the first knuckle... maybe even her ring finger!

Jill sucked and tongued Ron's knob as she watched Patty reach behind herself and pull down the zipper of her tight skirt. She swiveled her wide hips and she pushed it down to reveal that she wasn't wearing any underwear and that she had a dense patch of tightly curled black hair covering her pussy-mound. As she lifted her skirt with the toe of one high-heeled foot and began to fold it, she said, "I wonder if wifey is as good at negotiating with a cunt as she seems to be with a cock."

Jill found the term "wifey" to be slightly demeaning, and being talked about in foul language in the third-person like she wasn't there added to it. The subservient feeling made her pussy leak!

Patty reached down and put both hands on the sides of Jill's head, popped her mouth off of Ron's knob, and then pulled her to her feet and kissed her hard.

As she returned the kiss, licking and sucking on Patty's wide, full lips, she raised her hands to caress her big nearly-naked tits. She traced her fingers across the smooth flesh and then drew them together over the massive nipples. She played with the fat nubs, pinching them lightly and rubbing her thumbs across the tips.

Patty broke their kiss after a long, hard suck on Jill's tongue, and then moved her head down to her left nipple. "Let's see if you can suck a tit like you suck cock!" she said.

Jill opened her mouth to engulf the whole nipple and as she pulled a light suction she ran her tongue in a circle over its coarse surface. Every wrinkle and every little bump that the tip of her tongue encountered made Jill's pussy tingle even more. She swirled her tongue around the big protruding nub and then as she flicked its tip with the point of her tongue she increased her suction as much as she could, pulling the black cone of flesh into her mouth.

Patty moaned and said, "Oh, fuck yeah; wifey knows how to handle a tit!" As Jill sucked and swirled, and even lightly bit, Patty held her head and gently ran her fingers through her hair.

With her mouth firmly attached to a fat black nipple and as she listened to the woman's contented hums, Jill wanted to shove her hand into her pants and finger her pussy to an orgasm--which she was sure would have taken all of ten seconds. But again she managed to resist. Earlier, she had hoped to orgasm around Ron's fat cock as he fucked her, but now she was imagining cumming while this curvaceous black woman sucked and tongued her cunt. Envisioning both of those scenarios she was going to be lucky if she didn't blow her orgasm into her pants!

Patty moved Jill's head to her other tit, and as she latched on, Ron moved around behind her and lifted her blouse to expose her own braless tits. He cupped them and squeezed them, bulging her already swollen nipples, and then slid his fingers and thumbs out until he was pinching her nubs and stretching her tits. He pushed his body closer to hers and when she felt his boner nuzzle into the crack of her ass it was more than she could take and her pussy erupted. She groaned and her whole body shuddered and she sucked even harder on Patty's tit.

Recognizing the signs, Patty held Jill's face mashed against her big tit with one hand while she reached down and cupped her other hand into Jill's crotch. She pushed hard and rubbed her palm up and down.

The rough treatment and having her pants and panties ground into her erupting pussy made the second wave of her orgasm even harder and her legs shook while she moaned loudly around the tit that filled her mouth.

Suddenly, Patty removed her hand from Jill's crotch, pulled her mouth from her tit, and Ron let go of her tits and backed away from her. She stood there with her pants soaked with her own cum and her tits exposed below her pulled-up shirt and wondered if that was it. Was the fantasy concluded once she had an orgasm? If she'd known that, she'd have made sure she got fucked first. But then Patty relieved her concerns.

"Take her pants off," she said to Ron. "I think her hubby's raise is a sure thing; now we just need to see how big it is." As Ron pulled her pants and panties down, Patty pulled her top off over her head. As she stepped out of her pants she caught a glimpse of Ron and saw that he had stripped off his clothes while she had been sucking Patty's tits.

Patty took her face between her hands and kissed her with her big luscious lips and then said, "Have you ever eaten a black pussy before, sweet-thing?"

"Uh, uh," Jill answered with a shake of her head. "But... but if it will help with Jay's raise, I'm... I'm willing to." In fact, she was dying to! But she was having fun playing the meek wife being forced to be a sexual plaything to help her hubby get ahead.

Patty pushed a few things aside on Ron's desk then sat her naked ass near the edge and spread her legs. "Bend over and let's see if Jay's loving wifey is as good at eating cunt as she is at sucking cock." She then leaned back, resting on her elbows, giving Jill full access to her pussy.

As she had learned with Sandy, Jill wanted to appreciate Patty's pussy with her eyes before experiencing it with her mouth. It was so unlike Sandy's and she loved the differences!

The brown of Patty's skin became nearly as black as her nipples in the wide V that framed her pussy-mound. The lips of her pussy were full and appeared soft as they closed lightly against the dark, wavy flesh of her labia. The lips were clean-shaven up over the pronounced divot where her clit would be hiding, but then became a tangled nest of tightly curled, jet-black hair.

Jill first put her face into that nest of coarse hair and nuzzled into it, enjoying its scratchiness against her lips, her nose, and even her cheeks. She then slowly moved down, searching out Patty's clit-divot with her tongue. She found it but she didn't poke into it. Instead, she traced its teardrop shape with the tip of her tongue and then continued moving, lightly touching Patty's exposed labia all the way down.

Patty let out a little hum that told Jill that she was enjoying the tease. She didn't think it was acting, and it boosted Jill's self-confidence to think that she was able to please and excite this experienced woman.

She lifted her face and reached up with both hands to caress the dark bulge of Patty's vulva before gently pulling the lips apart. The moist, bright pink of Patty's inner pussy lips surprised Jill a little bit. Against the contrast of her nearly-black outer lips, her cunt seemed far more pink than Sandy's was. That somehow made it all the more exotic and erotic, and it made Jill's pussy leak.

Jill moved her fingers up and spread Patty's lips enough so that she could see her clit. Again, the contrast fascinated her. Its hood was nearly as black as her outer lips, but her clit itself was rosy pink.

When she bent down and flicked its glistening little head with the tip of her tongue, Patty groaned, "Okay, you fucking little tease! Get in there and eat my cunt!" She pushed on the back of her head, mashing Jill's face into her gash, and spread her legs even wider.

Jill chuckled to herself that she had been able to push this pro over the edge, and dutifully stuck her tongue out, sinking it deep into the pink cunt-hole she had just been looking at. Patty held her head tightly and used her face like a sex toy, rubbing it up and down through her slit, bobbing her head to get a tongue-fuck, and using Jill's nose to grind into her clit. Jill's whole face was smeared with cunt-juice and she loved it! In fact, she was so focused on the wonderful taste and warm, wet feel of Patty's cunt in her face that she had forgotten about Ron until he laid his boner into her ass-crack.

With her face spreading Patty's pussy wide open and her tongue shoved as deep into her cunt-hole as she could get it, Jill moaned, "Mmm!" and wiggled her ass in what she hoped was an inviting gesture.

Holding Jill's hips, Ron humped her ass-crack a few times, and then, holding his stiff dick with one hand, he backed away while pressing his drooling knob into the crack. He nuzzled his cock-head against her tight little asshole, but he didn't try to push it in. The outline that he'd gotten on the fantasy (which Sandy had written) said that Jill "would be receptive to anal sex," but he knew it would be better for her to save that until a little later.

He continued dragging his cock-head across her taint and then slid it up and down through her drenched pussy-lips. He lined up and leaned in, popping his fat knob into her cunt, but going no deeper. With his fist around his hard cock he squashed his cock-head around in her cunt-hole entrance, stimulating the million nerve endings that were concentrated there. She moaned, "Oh, shit!" deep into Patty's pussy and widened her stance enjoying his pre-fuck of her cunt.

With both hands back on her hips, he pushed another couple of inches into her cunt and then pulled back until his knob was spreading her pussy-lips. He then rocked forward and buried an additional inch or two before withdrawing. It wasn't until his fourth push that he had his entire cock stuffed up Jill's cunt. He then began long, slow fucks.

Jill felt her orgasm building and she wanted to bring Patty off at the same time. She reached up and pushed two fingers deep into the woman's cunt and began aggressively licking and sucking on her clit. Half a minute later, she got her wish as Patty let out a deep growl and her pussy erupted. Jill quickly moved her face so she could replace her fingers with her tongue in Patty's cunt-hole, and she sucked and swallowed as much of the hot pussy-juice as she could.

CaseyBea
CaseyBea
1,360 Followers