Cheating Boss

Story Info
Forced to pose as boyfriend of his boss's beautiful mistress.
8.1k words
4.6
182.6k
273
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
GeorgeTasker
GeorgeTasker
4,733 Followers

Steven Harper groaned as he slammed his hand down on the snooze button of his alarm clock. Another day had begun.

The twenty two year old climbed reluctantly out of bed and headed for the bathroom to get ready for work. Steven was average in almost every way. Average looking, average height (if you were generous) and average personality. He worked for a construction company as the personal secretary to the boss and owner. It was a slightly unusual job for a male, and Steven regularly got a hard time from the other workers there, but in these tough times he was just glad to have a job full stop.

He got out of the shower, dried off, brushed his teeth and hair, clipped a couple of loose nostril hairs from his nose, sprayed on some deodorant and then got dressed. As usual he wore a pair of black suit pants and a bright red polo shirt with the construction company logo on the breast.

Steven considered his reflection in the bathroom mirror for a moment. His hairline was definitely receding too much for a twenty two year old, and his almost non-existent chin made him look weak. At least he had nice eyes, or so his ex-girlfriend Sally had always told him. Right up until she'd dumped him six weeks ago.

With a sigh, he left the bathroom, heading for the front door. Steven never bothered with breakfast, and usually grabbed a Starbucks coffee on his way to work.

In the lounge there was a rather busty young blonde woman tied to a chair wearing a set of lacy white lingerie. Her ankles and knees were tied with rope and her hands were handcuffed tightly behind her back. She was gagged with a black ball-gag and had a slightly wild eyed expression of alarm on her face when she saw Steven enter the room.

Steven paused, looking over at her. She was prettier than the models Angus usually used, and she had a decent sized rack on her. Steven's room-mate Angus used their apartment for his work -- photographing bondage models for some dodgy website.

Steven approached the tied up blonde and regarded her thoughtfully for a moment. Then he reached down and cupped her large, bra-clad breasts with both hands, giving the ample orbs an exploratory squeeze.

The girl gave a muffled moan of protest, the ball-gag doing its job and keeping her complaints hushed.

Steven groped her boobs for a moment more and then gave her a pat on the head before departing. She'd probably complain to Angus when he got back, but by the time Steven got home from work she'd be long gone.

Opportunities like that was the main reason Steven put up with his rather strange room-mate.

Following his typical daily routine, Steven took the number 16 bus to work, stopping at the Starbucks just down the street from the office to grab a coffee. As usual, he tried to hit on the pretty redheaded barista, and as usual, she shot him down.

He got to the office a few minutes early and printed off his boss's diary for the day. Steven's boss, Trevor Mason, owned Mason Construction. Steven had worked for Trevor for just over three years, and in general, he got on well with the middle aged, ex-builder.

In fact, aside from the jokes about male secretaries from the other workers, Steven really liked his job. The only thing he felt a little guilty about was when he had to cover for Mr Mason's extra-curricular activities.

Trevor Mason had an absolutely drop-dead gorgeous wife called Lucy. Steven had met her only a couple of times, but each time he'd been stunned at how beautiful she was. However, despite his ridiculously attractive young wife, Trevor had, at last count, three girlfriends.

Unlike his rather average secretary, Trevor Mason was a remarkably handsome man, not to mention a rich one, which probably explained his constant success with the ladies. If anything, he was too successful for his own good, or at least the good of his marriage.

Steven himself couldn't understand why Trevor would want to cheat when he had such a sexy wife, but he seemed to be unable to stop himself. The number of different women that Steven had seen come to visit Trevor over the past three years was astounding, each one more beautiful than the last, although, in Steven's opinion, none quite as lovely as Trevor's actual wife, Lucy.

Trevor had even asked Steven to rent an apartment for one of his current mistresses; a tall, leggy brunette called Mandy. Not only had Steven arranged the rental, he'd also had to hide the costs in the company books so that Trevor's wife Lucy wouldn't spot the money coming out of Trevor's personal account.

When Trevor had made the request, it had made Steven feel quite uncomfortable, but with the economy in such a bad state, Steven couldn't risk losing his job. Plus, knowing his boss's dirty secrets had to help his job security right?

Steven was just getting to the bottom of his coffee when Mr Mason arrived at the office.

The usually immaculate Trevor Mason looked somewhat dishevelled this morning. He was unshaven and his rumpled shirt looked like the same one he'd had on the previous day. And, most unusually, he wasn't wearing a tie. He always wore a tie.

"Steve. In my office. We need to speak," he snapped as he breezed past.

Steven frowned, quickly gulping down the last dregs of his coffee and following Trevor into his office.

"What's up boss?" he asked.

"Shut the door Steve," instructed Trevor, running a hand through his short brown hair with obvious anxiety.

Steven pushed the door shut, feeling a little anxious himself.

Trevor glanced at his watch. "In the next hour or so you're probably going to get a call from my wife," began the handsome manager. "When she asks, I need you to tell her that Mandy is your girlfriend."

Steven was startled, that was the last thing he'd been expecting. "My girlfriend?"

Trevor nodded. "This is very important Steve. You need to tell my wife that Mandy is with you."

Steven frowned. "But why?"

Trevor sighed in frustration. "Shit Steve, you know how this goes. Lucy caught us."

"You and Mandy? But what..."

"She got a photo. I don't know how, but she did," explained Trevor, he sounded a little frantic.

Steven was still a little lost. "How does me being Mandy's girlfriend help?"

"It was just a photo of us going into Mandy's apartment, nothing too incriminating. I told Lucy that it was your place. It was the first thing I could think of."

"Oh... okay," replied Steven doubtfully. He actually thought that with Trevor's womanising ways, he might be glad to break up with his wife. Then he'd presumably be free to bang all the sluts he wanted to without having to sneak around.

"Worst case, you and Mandy might have to come to dinner with us. You know, pretend to be a couple and all that."

Steven's frown deepened. "I dunno. I'm not sure I'm too comfortable with that."

"Damn it Steve!" snapped Trevor in irritation. "This isn't up for debate. You're telling her that Mandy is your girlfriend!"

Steven fidgeted a little, he wasn't sure he was happy about lying straight to Lucy's face, that was taking things a little too far. "Maybe you should just tell her the truth, or get one of the guys to be Mandy's boyfriend."

"Damn it Steve!" repeated Trevor, getting even angrier. "I've already told her that you and Mandy are together. There's no going back here buddy. If you don't do this, you're fired."

Steven's eyes went wide. "I'm fired?" he asked incredulously.

Trevor nodded, his expression stern and determined.

"Okay," Steven relented. "I'll do it. I'll tell her." Steven figured that he'd already made plenty of excuses about Trevor's activities in the past, telling Lucy that Trevor was at a meeting when he'd actually been humping the salesgirl from the office supply company in his office, or that he'd gone to Chicago on a work trip for the weekend when he was actually shacking up with Mandy in her apartment. Surely one more lie wouldn't hurt.

"Good," replied Trevor, clearly relieved. "Good. We can get through this."

Trevor started pacing back and forth behind his desk. Steven had to admit he was somewhat surprised by his boss's reaction. He always thought that Trevor didn't care much for his wife, but apparently that was not the case. Or maybe he just didn't want to go through a costly and messy divorce.

Trevor waved Steven out of his office. "Get back to work then, I'm going to get out of here. I've got a date with that hot little redhead from the coffee shop down the road."

Steven's mouth dropped open in surprise. The lucky bastard. Did he really even need a fourth girlfriend?

"Oh, and if you do have to pose as Mandy's boyfriend in front of my wife, make sure you keep your hands to yourself. I don't want you coping a feel."

"Yes sir," replied Steven sullenly as he went back to his desk. He couldn't believe that Trevor had actually threatened his job like that.

Steven went back to work, coding up a bunch of invoices that had come in to get them ready for Trevor's sign off. Trevor left the office about ten minutes later, once again reminding Steven what he was expected to do.

"If my wife suspects you're lying, you're fired," were Trevor's last words.

"Asshole," muttered Steven once he heard his boss's car pull away and he was certain Trevor was gone.

The twenty two year old male secretary stared at his phone for a few minutes, trying to mentally rehearse what he would say to Trevor's wife Lucy.

Mandy was a beautiful girl, tall like a model, with the longest legs that Steven had ever seen. He remembered when he'd shown her around the apartment he'd leased for her and she had worn a tiny pair of cut-off jeans. Mandy's long tanned legs had looked incredible in those skimpy little shorts, and when Steven had walked behind her up the stairs, they were so short he could almost see the lower slopes of her buttocks. He'd gone home feeling very jealous of his overly fortunate boss. It felt very weird that he was now going to be telling people she was his girlfriend.

Sure, Trevor had warned Steven that he wouldn't get to cop a feel, but faking being a couple in front of Trevor and his wife could still be a bit of fun. He was sure he could wrangle a leg touch, maybe a quick kiss, or even a squeeze of that perfect ass of Mandy's. He could just chalk it up as acting if Trevor got pissed at him. Besides, he deserved to get something out of all this, right? Other than keeping his job of course.

Steven's musings were interrupted when the office door opened. He turned, expected to see that Trevor had left something behind (probably condoms or a dildo) and had returned, but to his surprise it was Trevor's wife Lucy.

The sight of Lucy Mason took Steven's breath away.

The stunning blonde was dressed in a dark grey business skirt, that was quite short, coming midway down her sleek, tanned thighs, but not so short to look slutty. The skirt clung tightly to her toned thighs and firm, round ass. Lucy's white blouse was quite loose fitting, well everywhere other than across her expansive bosom were it was stretched taut. The gorgeous blonde looked even bustier than Steven remembered, there was a hint of her deep cleavage visible above the neckline of her blouse as she'd left the top button of her blouse unfastened and she looked sexy as hell.

"Is Trevor here?" she asked, coolly regarding Steven. Lucy Mason had never been particularly warm or friendly towards Steven, and today she seemed even more aloof than ever. But it was probably understandable, given what she'd just found out about her husband.

Steven swallowed. He knew he wasn't a good liar, so having to lie right to Lucy's face rather than over the phone was potentially disastrous. "Ah, no. He's out at a meeting."

Lucy nodded, walking across the room towards her husband's office. "Come with me, I need to speak to you."

Steven nodded nervously. He saw that she was carrying an envelope in right hand. Presumably that was the photo Trevor had mentioned.

He followed his boss's wife into the office, unable to resist a lingering look at her sexy ass in her tight grey skirt. There was no obvious panty-line, and given the tightness of her skirt that meant she was presumably wearing a thong, or maybe even no panties at all. Steven's mouth watered at the mental image of what he imagined Lucy Mason's perfect ass would look like in a skimpy g-string.

"It's Scott right?" she asked him as they entered the office. She closed the door behind him, not helping his nerves at all.

"Steven," he corrected. You'd think she would know his name. He'd been working for her husband for over three years.

"Take a seat Steven," she instructed.

As Steven sat down, Lucy perched herself on the edge of Trevor's desk, crossing her long legs in front of her. The pose caused her short skirt to ride up even higher, displaying an ample portion of her elegant long legs. Steven noticed that she was wearing strappy, black high heeled shoes, and he could see her delicate toes and painted toenails poking from the end of them. Fuck, she was just insanely hot.

Lucy took a deep breath, the motion causing her ample chest to swell out, the buttons on the front of her blouse straining to contain her bosom. "I've got something terrible to show you," she solemnly told him, starting to open the envelope she'd brought with her.

Steven took a deep breath himself, steeling himself for what was going to happen next. He wasn't sure how he should react to the revelation of the photos, but whatever he did, it had to be convincing.

Lucy leant forward, handing Steven a large A4 sized photograph. As Steven took the photo, he couldn't help but notice that as she leant towards him he got a great view down the front of her blouse at her impressive cleavage. He could even see a lacy white hint of her bra.

Steven tore his eyes away from the stimulating sight and looked at the photo. As expected, it showed Mandy and Trevor outside the apartment that Steven had arranged for her to rent. Trevor had one hand on the small of Mandy's back, but nothing too incriminating as far as Steven could tell.

"I..I don't understand," he told her, trying to look confused.

Lucy nodded towards the photograph. "That's your girlfriend right?"

Steven glanced down. Mandy looked gorgeous, not as beautiful as Lucy though. It was crazy that Trevor would cheat on his sexy wife.

"Yes, that's Mandy. My girlfriend." It felt peculiar to say out loud, and he prayed that he hid the weird feeling from his facial expression. Surely anyone could see that Many was way out of his league?

Lucy nodded. She looked almost determined now. Had she actually believed his lie?

To Steven's surprise she pulled a second photo out of the envelope and handed it to him. This one depicted Trevor and Mandy kissing. It looked like it had been taken from outside, through the window of the apartment.

"W-what is this?" Steven's surprise and confusion didn't need to be feigned this time. Trevor hadn't mentioned anything about a photo of them kissing, how was he supposed to explain that without making his boss look bad?

"There's more," said Lucy sombrely, handing him another three photos.

In the next one Mandy had her top off and Trevor's face was buried in her cleavage. Then Mandy was on her knees sucking his cock, and finally they were both naked and Trevor was fucking her doggy style in the middle of the apartment's lounge.

Steven went pale. His boss was screwed now. There was nothing Steven could say to talk Trevor's way out of this.

He looked away from the photos back at Lucy. She was looking at him expectantly for his reaction.

"I...I can't believe it," he stammered, trying his best to look dismayed. He was feeling genuinely dismayed. Would he lose his job?

"The bastards," said Lucy. "They're cheating on us!"

Steven blinked. Had she said 'us'? Then he remembered. Lucy still thought that Mandy was his girlfriend, despite the fact that she'd confirmed Trevor was fucking her.

"I can't believe Mandy did this to me," said Steven after a moment's pause. There was no helping Trevor, but at least Lucy wouldn't think he was trying to lie to cover up for her husband. All he could do now was to stick to his story.

"I'm so sorry," Lucy reached forward to comfortingly touch Steven's shoulder. It was the first sign of any warmth that he'd seen from Lucy ever. "My husband is such an asshole."

"It takes two to tango." Steven wasn't sure if he was trying to shift some of the blame off Trevor, or if that would help him keep his job at all. Probably not.

Lucy sat back and gave a frustrated sigh. "I know. I'm so angry at him I could kill him."

Steven decided to remain silent this time. He looked back down at the photo of Trevor and Mandy fucking, taking the chance to admire Mandy's naked body. Damn Trevor was a lucky bastard.

"I bet you feel the same way," Lucy continued.

Steven nodded. "The cheating bitch," he growled, deciding to go with it. Maybe if he could get Lucy's trust he could somehow help his boss out, and therefore improve his chances of continuing to get a paycheck.

"I've suspected Trevor of cheating on me for months now," admitted Lucy. "But to see it like this... and with your girlfriend."

"It's a betrayal," agreed Steven.

"They're assholes!" snapped Lucy. "He's going to pay for this. I'm going to take him for everything he's got."

Steven paused, that wasn't good. He wasn't sure what he could say to that without looking suspiciously on Trevor's side.

Lucy continued. "I'm going to get him back for this," she announced, her tone sounding dangerous. "He's going to regret the day he cheated on me."

Steven nodded. "Revenge," he added, trying to go along with her.

"We should get revenge," nodded Lucy in agreement, clutching on to Steven's choice of word.

Steven nodded, starting to feel a little uncomfortable. She wasn't going to ask him to help cut up Trevor's clothes, or spray paint his car or something was she? He wasn't sure how that would help his job prospects.

Lucy's eyes narrowed as she looked thoughtfully straight at Steven. The nervous twenty two year old squirmed slightly under her scrutiny. Was she on to him?

"I know exactly what we'll do," declared the sexy blonde at last.

"What?" asked Steven, a slightly sick feeling in the bottom of his gut. This might not end well.

"We give them a taste of their own medicine." Lucy had an wicked looking grin on her face.

Steven frowned. "I'm not sure I understand."

Lucy nodded towards the photographs. "We make some photos of our own."

Steven looked down at the photos in his hands, seeing Mandy on her hands and knees and Trevor behind her, both of them naked. Suddenly Steven realised what Lucy was suggesting, or at least he thought he did.

"You...you mean me and you...?" his question trailed off as he looked back up at Lucy. She was nodding resolutely. Steven swallowed.

Lucy glanced around the office. "Trevor keeps a camera around her somewhere right?"

"Uh, yeah... for photographing worksites." Steven got up and went over to the cupboard on the side of the office, opening it up and taking a digital camera from the shelf.

Lucy still had her wicked grin. "Does that thing record movies as well."

Steven frowned down at the camera, trying to keep his hand from shaking. "Yeah, it does."

"Perfect," whispered Lucy.

"Um...Mrs Mason?"

"Call me Lucy," she replied.

"Yeah, um... Lucy, I'm not sure this is such a good idea," he lamely tried to protest.

Lucy was determined though. "Of course it's a good idea. It's a least of what those two deserve for cheating on us."

"I know, but, my job..."

Lucy sighed. "Don't you worry about that. I'll make sure Trevor doesn't fire you. He wouldn't dare cross me after this."

Steven swallowed, he wasn't completely convinced, but at this point he didn't really have the courage to argue with her. Plus, he was more than a little curious about how far she was planning to go with this revenge.

GeorgeTasker
GeorgeTasker
4,733 Followers