Jack Gets Caught by His Boss

Jack's work phone rang. Jack liked to keep "Church and State" matters separate and usually turned his work phone off on weekends. Somehow he forgot this weekend to turn it off.


"Jack?"


"Yes. Oh. Amanda. How are you, what's up?"

"Jack, sorry to disturb you on Saturday, I know you just got in from the road but I really need you to meet me immediately."

"Sure Amanda, but where? I can be in the office in about 30 minutes."

"No. Meet me at my condo. Can you leave now?" As usual, right to the point, all business. Probably her whole life.

"Sure. Of course, Amanda, but why the drama - is this serious?"

"Very. See you in 30 minutes." She disconnected.

Jack was now concerned. His 28-year-old boss had not earned the nickname The Terminator for nothing. Jack quickly reviewed his recent performance in his head and as far as he was concerned he was in the clear.

Although unusual and despite their age difference, Jack was 52, Jack and Amanda got along quite well. He had considered himself to be Amanda's right-hand man so to speak. Jack smoothed over the lumps that were sometimes caused by Amanda's very practical direct approach.

Jack and Amanda had worked together now for a couple of years. As VP, Jack understood that she was his boss and unlike some men of his generation who bristled at working for someone younger, a woman no less, Jack was OK with that. He'd risen in the firm as far as he wanted. Maybe, as far as he was able. He was very good at what he did and appreciated Amanda recognized his talents.

On the other hand, Amanda was still rising. Late twenties now, very confident, very smart and, ok, frankly very hot. At 5' 8" she used her looks to her advantage. Typically she wore a business suits with the skirt about mid thigh. The jackets and blouses always tailored. Her lingerie was always discrete but from what did show one got the impression it was very sexy and very expensive.

Actually, she was scintillatingly beautiful. She was also very ruthless, didn't, beat around the bush and did not suffer sycophants or fools well.

Some of the men in the office arrived at their demise wasting time speculating on whether or not she's definitely bald down there or sucks cock or likes anal or otherwise speculated ad nauseam about her peccadilloes and such. Curious how a man's mind could run riot like that. Silly boys. Jack realized very early upon Amanda's arrival that her sole interest was on driving the business forward.

Some found her gruff, severe, stern, aka, a bitch, Jack just respected her. She had a tough job, she was in-charge and frankly, she got the job done. Jack's ambition was behind him so he was quite happy to support her.

Their business was challenged recently but, thanks to Amanda's strong leadership the company had managed to sail to calmer waters. This despite, the hurt feelings and broken wings left in her wake.

Jack checked her address on the private company directory. Amanda lived in one of the downtown condo towers that had popped up in recent years in the city core and headed directly there.

Jack arrived at the condo in record time and parked easily in the guest parking.

He intercomed up, "Jack? Come on," and was buzzed through the door.

When she opened the door, Jack noted that Amanda was dressed like a typical "Friday" workday in a delightfully pleated burberry plaid short skirt and fitted white blouse ensemble. The skirt and blouse were nicely complemented by fashionable pumps. As usual her makeup was perfect, her lipstick a deep sensual red. Though Jack thought it odd for an early Saturday morning he realized this was not entirely out of character for Amanda - she never did casual. Jack now felt underdressed with his kakis, unbuttoned collared shirt and sandals

"Jack, thanks for coming over on such short notice on the weekend," she ushered me in, "You're probably wondering why I asked you over."

"Well, yes. It's a bit unusual", he said, "but I figured it must be serious."

"It is." She closed the door behind them. "Let's sit in the living room," and led the way.

As she led him on, Jack focused on her fantastic 36 24 37 figure that commanded his attention as it had done a thousand times before. He snapped to attention when she turned and smiled at him. Did she notice?

She sat on a chair across from the sofa and crossed her legs. Immediately, he was drawn to her long wonderful legs. Her skirt had drawn up slightly, now slightly higher on her thigh, the drape of the pleats revealed a bit more leg than the tight pencil skirts she normally wore at the office. Was that a hint of lace top he thought? Never mind! They were here on serious business.

"Jack, please have a seat, " pointing to the sofa directly across from her. She smiled.

Jack was oblivious to the trap that was now sprung.

"Jack," she leant in, uncrossing her legs, her arms crossed on her knees., "I'll be plain: I've respected your council, advice, loyalty. Frankly, you've saved my ass," she shifted subtly to tilt her pelvis toward him, "more times than I can count with the board, but frankly - I don't know how to put this other than straight out." She stood up suddenly looking at him coldly, "Jack, I feel your eyes on my ass and tits all the time and it's fucking annoying!"

Amanda was like a laser getting to the point. Jack was stunned. Not in a million years, would he have bet a million dollars before he heard "ass", "tits" utter from his bosses lips. What next "cunt"?!

Small beads of sweat emerged on his brow. Ok, he thought, this was very serious.

"Jack, there's no point in denying. I'm a woman. We know." She sat down again directly in front of him. She shifted her legs and crossed them, maybe a nanosecond slower than needed and like a shiny light reflection, Jack was again drawn to looking at her crotch. Were they white? Lace? Sheer? Were there any panties?

"Aha!" she yelled, shocking him out of distraction, "Caught you! Jeez! You pervs, you really can't help it.

"What?"

"You were trying to look up my skirt!"

"No! ABSOLUTELY NOT!"

"Tell me, Jack, are you a beaver hunter?"

"Sorry, I don't understand?" Fuck! Jack realized now he was totally caught! Well and truly screwed. Without benefits.

"Oh Jack," she said, "Don't you dare fuck with me!" She leaned forward. "Yes, you do. Remember when you were in high school? You and your perv buddies were probably always looking up girl's skirts for that flash of white panties. You were one of them - weren't you?"

"Of course not," Jack blurted. He stood up abruptly, trying as best he could to sound and look indignant but to be truthful he was not sure where he was going. His reaction was a pure "manmalian" flight response.

"Sit down Jack, your play on indignity might have worked were it not you were sporting some wood," Amanda was now looking at his groin.

Jack sat down, his hand in his lap now. His heart was thumping like a rabbit.

"Yes, you were one of those pervs. You know it. I know it now, so let's not beat around the bush, so to speak." Smiling, she uncrossed her legs and spread them wide exposing all her charms before him. She looked at him directly, noting his reaction. Poor man, she thought.

Immediately, he was drawn like a moth to a light. That light, in this case, was an exquisite pair of white lace briefs. Jack could discern by the width of the gusset and rise that they were in fact briefs she was wearing.

Briefs were Jack's favourite style of women's underwear. Probably it was his old school early sexual experience. Bikini briefs were what all the hot girls wore. Jack also noted that Amanda's pair was completely sheer, including the gusset. He thought: God they must be a mess by the end of the day. As he stared, he could clearly make out the form of his boss's labia and from the subtle sheen could tell she was just a little excited by her presentation. Jack also satisfied himself that his boss was indeed completely bald.

"Jack? Jack? Have you heard a word I said? See. You can't help yourself!" As quickly as she revealed her treasure, she closed and recrossed her legs.

Jack snapped out of his spell.

"The evidence is plain." Her eyes again on the bulge in Jack's kakis, "Well now, we have established that you are a pervert. More than that - you are a panty perv. Clearly, Jack, we need to get this straightened out between us. We have to come to an understanding, otherwise, I don't see how we can continue to work together." A slow smirk crossed her lips as Amanda rose and moved toward him.

She sat beside Jack, leaned close and before he could react, kissed him full on the lips. At first surprised, Jack responded, as she expected, enthusiastically and Amanda engaged him more aggressively. First a lip nibble then a little deeper, harder. As their ardour rose, Jack could smell her perfume, her hot breath, he felt the slick of her glossed lips on his. Her hand dropped to Jack's pant front and brushed his hard cock, stiffening it further.

"So Jack," she whispered in his ear, "can we agree that I'm in charge of this project"

Jack nodded.

"Good. So, this is how we are going to settle this matter," She continued to speak between earnest light and deep kisses. "We can deal with your abhorrent behaviour at work on Monday with our HR department or we can see what kind of arrangement we can pound out, sorry I meant, negotiate between us so we can move forward. What do you want?"

"Here please. PPPPPound..." It was all he could muster.

"Good. Then, let's get started. While we're playing you may call me Mandy - OK?"

Jack felt her tugging at his belt and pants to undo them but then paused, "Jack. Sorry. I barged ahead. Before we begin, we should be clear on the ground rules - you know how I love contracts," She smiled. "First: Girls cum first. So don't blow your load in the first minute 'cause I'm kinda hot and, mind you, it's happened with some of the other former execs."

She chuckled, remembering.

"'Where was I, Oh yea. After I cum - First: I might be inclined to suck your cock dry and then ride you like a cheap dildo and fuck you till you beg me to stop or I cum again. Rembember: This is not a quid pro quo arrangement. This is a quid cum Mandy arrangement. You get it? I'm the boss. Are we aligned on this mission?"

She laughed, stood and started to unzip her skirt, drawing it down across her ass, at the same time pulling the sheer panties lower. She looked over her shoulder, "So, Jack, are you up for the fuck of your life?

Jack nodded meekly. His mouth watering.

"OK, then: Let's get this party started."

The skirt dropped on the floor and she stepped out of the entanglement heading for her bedroom.

"Come'on big boy. the bedroom is more suited to play and this ass ain't gonna fuck itself," she smiled spanking her left cheek.

Jack stepped out of his pants, dropped his underwear and peeled off his shirt as he followed her.

By the time Jack arrived in the bedroom, Mandy was sitting on the corner of the bed, her thighs spread.

"So Jack. One more thing, before we begin to play. I almost forgot; Do you like eating pussy? My experience is, I think you do. Panty lookers are panty lovers; panty lovers are panty sniffers and panty sniffers love eating cunt. Am I right?

OMG though Jack. This was gonna be the best time ever, "You got me pegged Boss."

She beckoned him closer with a wry smile and wavering finger.

"Hmmm, Nice cock, Jack." Most of Jack's blood was now locked in his very rigid cock.

Mandy beckoned him toward him, directing him down toward her spread thighs.

Jack knelt as directed. Though still wrapped in sheer panties, Jack could clearly discern beneath that transparent veil Mandy's pussy was as bare and smooth as silk. Her eyes covered his every move, Jack leaned forward and gently kissed her just above her mound, sucking into savour a taste. He moved further down extending his tongue in advance, desperate for a taste of other than fabric and then reached the well where his tongue was rewarded with her sweet liquor. Jack broke away now and kissed and licked her smooth and soft inner thighs and proceeded to pull off her panties.

She tasted wonderful and he heard Mandy moan deeply in response to his actions.

Mandy raised her hips and pushed forward to his mouth. In response Jack's tongue moved around her pussy and lapped playfully against her sensitive lips, teasing her but not yet touching her clit. He could see that her pearl was still hooded.

Jack pulled back a moment to catch a glimpse of Mandy's beautiful face in bliss before diving in on her pussy again. He rolled his tongue through her labia folds. He softly teased her clit. Mandy groaned in response: she arched her back pushing herself against him but Jack pulled back as she tried to push her pussy against his mouth to get more stimulation. In response, he pushed her long sexy legs further apart and began to tongue wash the full landscape of her vulva left to right, top to bottom, savouring the increasing volume of sweet juices that flowed forth.

"Oh my fucking God, Jack," she moaned. "Oh Fuck! Yes! Please eat me! Please eat my cunt. Don't you fucking dare stop licking me"

Jack pressed on, tempering his pace and pushed his tongue further into the creases of her labia, savouring the differences in texture, scent and flavour. Again, he deliberately avoided her pearl and moved his hands to the inside of her thighs, placing them on either side of her pussy. With his thumbs, he gently pulled apart her pussy lips to reveal her beautifully pink and wet inner folds.

"OHHH fuck Jack, Yesssss!"

Jack now sucked her engorged pussy lips into his mouth and pulled at them, stretching them until they slipped sloppily from his mouth. Mandy let out another long low groan gripping his head with renewed vigour.

"Fuckkkkk yes. Don't stop..."

Again, Jack slurped her delightful meaty oyster up for another fresh assault.

He licked her again and again in this fashion. His tongue circled her pussy, and then he moved his assault from her frothy fuck hole to her pearl. Gently he flicked his tongue over her engorged button. Mandy trembled and moaned, delighted at this new attention. "Fuck yes, Jack. There. There!

Jack sucked up her wetness. Mandy whimpered in response and arched her back, pushing her cunt harder still against his mouth. Jack flattened his tongue against her splayed vulva and she cried out. "OWWWW FUCKKKK!" Her thighs clamped around his head, holding him tight as she flooded his mouth with her sauce, her whole body trembled as waves of pleasure washed over her again.

Distantly he heard her cry out, "Oh, my fuckin' God. I'm cumming! You're making me cum! Oh fuck yes, yes, yes!"

Jack flicked the tip of his tongue delicately against her clit several more times as she continued to spasm fiercely against his mouth.

Mandy moaned and groaned and collapsed back on the bed. Feeling her relaxing after her climax, Jack moved beside her.

"Fuck, Jack if I knew you had skills like that we'd a had this talk a long time ago. Jack trailed his hand now over her hip and up her inner thighs. "Oh no, Jack," she tried to push away his hand, "No. No. Seriously, I can't take any more...you're killing me!"

"Relax boss," he said lightly, kissing her softly on the lips, jaw and neck. Very softly, very slowly Jack slid his index finger into her slit. He stroked her softly, careful to avoid her sensitive clit.

"Fuck Jack, I don't know if I can take much more," Mandy groaned breathlessly, as he slowly strummed her vulva. She reached for his wrist to try to control the pace but didn't push him away.

Soon all she could do was moan as Jack continued his finger assault. One finger dipped inside her, slowly circulating the entrance. One finger was soon followed by another. Mandy's breath quickened.

"Oh yes, yes, yes," was all Mandy could manage to say asJack increased the pace and fucked her faster with his fingers. He directed his thumb to circle her clit. He leaned into her face, licking her lips, she grabbed his head and slid her tongue into his mouth, moaning soulfully. Returning his kiss fiercely. Jack's cock strained in reaction.

Shortly, he felt her pussy flood his fingers. Jack fucked her even faster now, pushing another finger deep into her hot wet cunt. Mandy grabbed his wrist tighter to restrain his assault and then screamed in ecstasy as she came again, her pussy clenching fiercely around Jack's fingers while they kissed and tore at one another's lips.

"Oh fuck yes!" Mandy called out and her pussy slowly stopped contracting around his fingers. Jack brought his hand to his mouth and licked the sweet juices, giving Mandy a taste of herself.

She was sprawled back on the bed, her legs wide apart, her pussy lips swollen and glistening and dripping with her sweet juices.

"Oh MY Fucking God! I've never cum that hard before," she gasped in deep recovery breaths. "A talented hand you've got there Mister." She rolled and placed her thigh across his legs.

Smiling at him, "So you wanna fuck?" She pulled him to her face and kissed him sloppily, savouring again her taste on his lips and beard, "I need to fuck. I need to feel your cock inside me."

Reenergized, Mandy straddled him and positioned his engorged cock at her soft pussy lips. She pushed back slowly and Jack watched as his cock spread and slide into her sopping cunt. He gave himself over as her furnace gripped him.

Mandy's eyes rolled back, "Oh my fucking God," she gasped, "your cock feels so big inside me."

He gazed deeply into her topaz eyes as she started to fuck him slowly, First grinding her pelvis against his as she bit her lower lip. Then lifting up and sliding his cock in and out of her slippery pussy. He loved the feel of his cock parting her pussy lips and then sliding up inside her.

Mandy moaned as Jack joined in thrusting upward to match her movements. Now she reached around her back and undid her bra, pulling it away from her breasts and flinging it aside. Jack could believe the sight of her pert breasts. Mandy pulled hard on her nipples and moaned. Leaning, she places her breast at Jack's mouth. "Suck my tits Jack, suck them hard!" Jack didn't need to be told twice and took them into his mouth softly nibbling at her taut nipples. "Harder, Jack, I'm so close." Jack sucked harder, exciting Mandy further.

She ground against his cock faster, moaning deeply,.eager to get more of him into her tight body.

She bore in on his eyes, her face bound in a fuck grimace.

"Oh yes, yes, your cock feels so good, fill me with your cum. I want to feel your hot load explode inside me."

Jack judged by her breaths and pace the she was going to come again. He grabbed her hips and held her steady. At the same time he pistoned his cock faster into her slim body again and again. Mandy grabbed her breasts fiercely and tugged on her nipples.

"Fuckkkkk Yes. I'm cumming! Cum with me Jack!! Yes, yes, YES!" she cried out loudly and Jack felt her hot pussy clamp around his cock and her body collapsed against him as she convulsed again in orgasm.

With a groan and his cock buried deep inside her, Jack exploded. Shot after shot of his thick warm cum sprayed into her as his cock pulsed inside her.

"Oh yes, baby, I can feel your cum. Fill me, fill me."

Jack's eruption seemed to go on for minutes.

Mandy collapsed on top of him. They were both soaked in sweat, both basked in the glow of their ebbing fires. Soon they both started to laugh. Mandy spilled off him, cuddling up beside him. Jack's huge load dribbled from her pussy.

"That was some load, Mister," she said laughing, drawing her finger across his chest.

"That was some fucking boss."

"Hmmmm, yes it was," she nuzzled him closer, "I think we may have to arrange for more of these conferences, what do you think?"