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Team Player (Part 1 of 2)

"Bailey finds himself in the middle of some after-hours roleplay with the boss and his gorgeous assistant."

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Though my mouth felt parched, my palms were clammy as I made my way toward Mr. Carr's office. The scenario about to unfold seemed too surreal even for a dream.

Yet it was happening.

His door was open, just as he'd said it would be. Light spilled out onto the hallway carpet, and as I approached, I heard his low voice. Then I heard Isla's, even softer.

The offices all around us on this floor of the building were deserted. I was usually here till late in the evening; as the janitor, I cleaned up the white-collar detritus left behind on a daily basis. I didn't mind the quiet, or the rows of darkened doorways, and since plenty of company employees tended to put in long hours, I'd gotten to know some of them fairly well.

It was only last week, at around this same time, that Mr. Carr had beckoned me into his office. While he wasn't at the very top of the company's food chain, he was pretty damn close. At first, I worried I might be in trouble. Maybe someone had complained that my cleaning wasn't up to their satisfaction. 

But no. Mr. Carr's smile was friendly as he clapped me on the back. "Bailey, how have you been?"

"Ah, can't complain." Standing awkwardly in his office, I waited for him to close the door. 

"Please, have a seat." He gestured toward one of the chairs in front of his desk. After we'd both sat down, he flashed another winning smile. The smile I returned was genuine, because as different as Mr. Carr and I were, he'd never once looked down on me. Whenever we passed each other in the hall, or I knocked on his door for permission to enter so I could empty the trash, he spoke to me the same way he addressed his peers. Some of the other executives wouldn't even acknowledge my existence. 

I guessed Mr. Carr was in his mid-forties, about twenty years my senior. His light brown hair was neat and short, his face clean-shaven. I'd noticed long ago that he was always impeccably dressed. While my muscular build reflected all the time I spent at the gym, Mr. Carr had a wirier frame, and he was a little taller. 

As I sat in his office that evening, he and I made small talk for a few minutes. Then his expression grew serious. "I'd like to discuss something of a personal nature with you, Bailey, but first, I must emphasize the need for absolute discretion."

"Of course," I immediately replied, sitting up straighter in my chair. I admired Mr. Carr and all his accomplishments, so I wanted to make a good impression when he was about to confide in me. 

Seemingly out of the blue, he asked, "You like Isla, don't you?"

Isla was Mr. Carr's assistant. She was also breathtakingly gorgeous. Though she was only a few years older than me, it was obvious she was going places. With wavy blonde hair and blue eyes, she received lots of attention from the men in the office. And from a few of the women, too. I was definitely guilty of sneaking glances at her ass. 

Like Mr. Carr, Isla was always friendly to me. No matter how busy she might be, she took the time to ask how my day was going. I'd overheard whispers about her and Mr. Carr being far more than mere colleagues, but they were unfailingly professional in my presence. 

"Yeah, Isla's really nice," I said to Mr. Carr. All the while, I wondered why the hell he was asking me how I felt about his assistant. My growing nervousness made me run a hand through my hair, which was darker than Mr. Carr's. Had Isla made a complaint about me? I couldn't imagine her doing something like that, but then again, I didn't really know her.

Over the next half hour, Mr. Carr made it clear Isla had done nothing of the sort. I often had to remind myself to pick my jaw up off the floor, because I found myself gaping at the man while he explained that he and Isla were in fact romantically involved. And not only that, but she also had a roleplaying fantasy she wanted to fulfill. Here in the office, long after regular working hours had ended.

I thought I understood then. "Oh, so you want me to take a night off to give you two privacy? I can definitely do that."

Mr. Carr clasped his hands on the desk before him. "That's not quite what she has in mind." For the first time ever, he seemed a little unsure of himself, even uncomfortable. "The thing is, Isla wants you to be part of this roleplay."

My jaw dropped again. "Me?"

He nodded firmly. "And while this isn't exactly a fantasy she and I share, I'm willing to go along with it because I'm crazy about her. She turns me on in a way no other woman ever has. Not even my ex-wife when we first fell in love. So..." Placing his hands on the desktop, he narrowed his dark green eyes slightly. "Are you still with me, Bailey?"

Through my shock, I managed to say, "Uh, yeah, Mr. Carr. But what exactly does Isla's fantasy involve?"

He proceeded to explain that Isla wanted to be treated like a "bad girl" who was in major trouble and risked losing her job. In order to keep it, she had to agree to let Mr. Carr have his way with her.

And she wanted me to show up and then join in as our boss "punished" her.

"You can understand why I emphasized discretion," Mr. Carr said, and I quickly nodded. "I know I'm taking a huge risk, both professionally and personally, as is Isla. At first, she and I considered keeping this roleplay between us. But she goes wild at the thought of another man being involved, someone she's never been intimate with. And of course, he has to be someone she's attracted to, and whom we both trust." His smile held a hint of slyness. "You fit the bill."

Opening my mouth to respond, I could only stammer, "I... I..."

Mr. Carr held up a hand. "If you agree, and you subsequently keep your mouth shut, I'll ensure that your end-of-year bonus is doubled."

Jesus, the man thought I was trying to drive some kind of hard bargain! How did he not realize that I would have given my left nut simply to watch Isla fuck? And to know she wanted to fuck me? That was my fantasy come true!

"I'm happy to help in any way I can," I said, somehow hiding my excitement. Merely hearing about Isla's forbidden desires had me hard. 

"I'm glad to hear that. I always knew you'd be a team player." Leaning back in his chair, Mr. Carr rubbed his chin while regarding me. "You do understand that Isla will act as if she's unwilling and being coerced. That's a large part of what turns her on about this." Again, I nodded. "But if you or I do something she's truly not comfortable with, her safe word is lilac. If you hear that, we stop immediately. Understand?"

"Absolutely, sir."

After going over a few more details, we rose from our chairs, and Mr. Carr shook my hand as though I were a respected business associate. "I look forward to seeing you next week, Bailey."

And that was how I found myself here tonight, standing in his office doorway. At my sudden appearance, both he and Isla looked over at me. She was leaning against his desk, her arms crossed tightly over her chest. Mr. Carr had planted his hands against the desktop on either side of her, so his arms served to prevent her from moving away. He'd shed his suit coat and tie, and his shirtsleeves were rolled up his forearms. Since Isla had taken off her blazer, I could easily make out the straps of a red bra through the fabric of her white blouse. I knew she never would have worn something like that during normal office hours. She must have changed her bra after work. 

As for me, I was in my usual janitor's uniform of dark blue pants and a pale blue button-down shirt. I'd taken extra care with the outfit, just as I had with the rest of my appearance. Freshly showered and shaved, I'd made every effort to look my best.

Mr. Carr smiled at me, but there was no warmth in his expression. I had to remind myself it was merely a part he was playing, because the man appeared downright menacing. His eyes were cold and calculating as they met mine.

Isla, meanwhile, seemed utterly distraught. The unease in my voice was genuine when I said, "I'm sorry for interrupting. I'll come back later"

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"No, Bailey. Stay." Mr. Carr's tone bordered on stern. After pushing off the desk, he turned to me and added, "Close the door behind you."

Swallowing hard, I did as he commanded. It was difficult to meet Isla's gaze, so I looked around the large room instead. Its huge windows normally offered a spectacular view of the city, but the blinds were now lowered and closed.

Isla's plaintive voice drew my attention back to her. "You don't need to involve Bailey in this," she told Mr. Carr.

Seizing her chin with a swiftness that made my eyes widen, he growled, "You don't have a say in the matter!"

Holy shit, the man should have been a famous actor, because right now, he had me terrified! "Sir," I began.

Mr. Carr released Isla but kept his contemptuous glare fixed on her. "Do you know what she's done?" He turned that stare in my direction, prompting me to quickly shake my head. "She behaved so egregiously today that I lost a crucial client as a result!"

That served to bring me back to reality, if only a bit, for I knew Isla would never do such a thing. But her lips quivered as she cried out, "Please don't fire me! I'll do anything you want."

The calculating gleam returned to Mr. Carr's eyes, and he actually smiled. "Anything?"

"Anything," she repeated, her tone vehement.

His stare dropped to her breasts. Now that she'd uncrossed her arms, I could easily see the red bra she wore. Mr. Carr toyed with the top button of her blouse, twisting until it fell into his palm. "Take this off," he demanded.

Isla's eyes widened in alarm. "Sir!"

"You said you'd do anything," he reminded her. "Did you mean it, or was that just another of your fucking lies?"

She lowered her head so that her hair shielded her face. Though I couldn't see her expression, I easily discerned her trembling while she unbuttoned her blouse. "Sir," I tried again, my voice pathetically weak. "This isn't appropriate."

Mr. Carr's eyes flashed a warning at me. "Do you want to lose your job?"

"No, I absolutely do not."

"Then get over here." His grin turned sinister. "I know you'd love to have a nice, long look at Isla's tits. And you're in luck, my friend, because she's going to show them to you."

Isla made a whimpering sound while shrugging out of her blouse. The bra she wore pushed up her breasts in an enticing way, offering them like forbidden fruit. Mr. Carr slid a fingertip along her cheek. "Come on, baby," he murmured. "If you want to keep your job, you'll show us those titties."

This felt so wrong; it went against everything I'd learned about how to treat a woman. But I couldn't deny the fact that I was rock-hard. When Isla gave me a pleading look, I remained quiet. The only sound I heard was my own rapid breathing. 

Slowly, she unclasped her bra and then lowered the straps from her shoulders. She appeared reluctant to let the undergarment fall from her breasts, so Mr. Carr gave it a fierce tug. As soon as her gorgeous tits were exposed, my cock pulsed. My boss licked his lips while gazing upon those firm mounds capped with rose-hued nipples. 

He cupped them in his hands, giving each one a gentle squeeze. "Oh, these are nice! I've jerked off plenty of times imagining these beauties." Looking over at me, he said, "Get your feel of them, Bailey."

Biting my lower lip, I again obeyed. Isla stared down at us, her face stricken while we fondled her tits. My mind still reeled in disbelief that she'd chosen me for this, and that she was risking her joball our jobsfor such a taboo fantasy.

But I'd be damned if I could stop myself from lowering my mouth to her left nipple.

"Bailey, please!" she begged.

I extended my tongue and gave that stiff peak a lick. "I'm sorry, Isla, but I can't lose my job."

Mr. Carr began hungrily suckling her right breast. Dropping my gaze, I watched as he slipped a hand under her gray skirt. At some point before my arrival, she'd removed her pantyhose, and I ached to discover what she might still be wearing. 

Mr. Carr satisfied my curiosity when he allowed Isla's nipple to escape his lips and groaned, "Oh, you are a naughty little slut, aren't you? No panties, and your pussy is soaking wet!"

As if to prove his words, he withdrew his hand from between her thighs, then held it up for me to see. His fingers were covered in Isla's juices. She let out a choked sob when he brought those fingers to his face and inhaled deeply to draw in her scent. My mouth watered as I watched him lick her juices from his skin. 

Without warning, Mr. Carr grabbed Isla's hair and drew her head back. She didn't fight when he worked two fingers between her lips. "That's it, show me what a dirty girl you are," he coaxed. The sight of her sucking his fingers made my cock painfully hard. I was dying to take it out and stroke. 

Mr. Carr removed his fingers from Isla's mouth and gave her a fierce kiss. As he drew a whimper from her throat, I again sucked at her tit. My hands busied themselves yanking up her skirt until it was bunched around her waist. 

Isla broke the kiss in order to beg again. Her breasts rose and fell with each heavy breath, inviting Mr. Carr to pinch her nipple. The pain of his touch made her gasp, but my tongue proved soothing as it swept over her right breast, and then her left.

"Mr. Carr, I'm sorry," Isla said in a tremulous voice.

"I know that, but you still need to be punished."

I sank to my knees so I was almost eye-level with Isla's pussy. It was completely smooth, and her fleshy inner folds peeked from between her outer lips. Mr. Carr took a step back to watch me spread Isla's labia apart. "You're rightshe's dripping wet," I said. By this point, my erection was straining against my pants. 

"Find out for yourself just how good she tastes," Mr. Carr urged me.

I lost all self-control, devouring Isla's pussy with utter abandon. Almost immediately, her juices coated my face. I heard her draw in a shuddering breath just before she wove her fingers through my hair. "Bailey, oh God! Oh, we shouldn't!"

Isla's clit was quite large, practically begging to be sucked. As I readily did so, her whimpers turned to moans, and her grip on my hair tightened. Out of the corner of my eye, I saw Mr. Carr stroking himself through his pants. 

With my mouth and my fingers, I lavished attention on Isla's swollen bud until she began grinding against me. "This makes me feel so dirty!" she wailed. Already, she'd begun shaking. 

"You should have considered the consequences you'd face for causing me to lose a valuable client!" Mr. Carr scolded.

My tongue flicked mercilessly against Isla's clit. When she wriggled in my grasp, I strengthened my hold on her. Another helpless wail escaped her lips, but Mr. Carr only laughed. "You're going to come, aren't you?" he taunted. "What a bad girl you are, so wet and horny even when you know two men will claim that sweet cunt of yours tonight."

"I'm not!" she managed to cry before the first orgasmic shudders rippled through her body, rendering her speechless. Almost doubled over, she clung to me as my tongue inflicted its own form of punishment.

"Bailey, ah fuck!" she finally rasped out. Though I felt her muscles tighten beneath my hands, I was reluctant to stop. I wished I could spin her around and bury my face between her ass cheeks. 

Once Isla's orgasm had subsided and she was able to stand upright without holding on to me, I lifted my head to meet her eyes. She gazed upon me as if I were a stranger she both feared and desired. 

After I released her and climbed to my feet, Mr. Carr gave her another hard, punishing kiss. "Still willing to do anything to keep your job?" he whispered against her swollen lips.

Isla hesitated only a moment. "Yes," she whispered back. "Anything."

Lifting an eyebrow, Mr. Carr smiled. "Good. Then take off that skirt and get on your knees."

Published 
Written by Obsolete_Fox
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