As Isla stepped out of her heels, her eyes met mine. Before, I'd had trouble holding her stare, but now that the taste of her pussy lingered on my tongue, I made a point to stroke my dick through my pants. Isla drew in a sharp breath, then reached to unbutton her skirt. I could easily hear the zipper's slow descent. 

When the garment dropped to her feet and she stood completely naked before me and her boss, I was struck by how much smaller she looked without those four-inch heels. She appeared utterly vulnerable with no clothing to hide behind. 

Mr. Carr made a guttural sound while looking her up and down. "You just might keep your job yet," he told her.

Isla's face was full of pleading as she knelt before him. Gazing upon her, Mr. Carr's expression grew surprisingly tender. In that moment, when he extended a hand to caress her cheek, his mask of brutal dominance slipped, giving me a glimpse of his true feelings for Isla. For several fleeting seconds, I was able to see the two of them as they really were: not as an executive and his assistant, but as a man and woman clearly in love.

Then Mr. Carr resumed his role. "Take out my cock," he ordered Isla. While her fingers fumbled at his pants, he flashed me a grin. "Go on and whip out your dick, Bailey. Show Isla what she has to look forward to."

Isla's faint whimper didn't stop me from hurrying to obey Mr. Carr. In seconds, my hard dick was fully on display. Isla now held Mr. Carr's cock in her hand, but she paused her stroking in order to stare at my erection. 

I certainly didn't make a habit of checking out other men's dicks, but as I stood next to Mr. Carr, I couldn't help but compare his with mine. I discovered he was a bit longer, maybe a half inch or so, while I was thicker. Neatly trimmed pubic hair surrounded the base of his cock. I was completely smooth, having shaved earlier. 

Isla's lips parted, and I saw a hint of pink tongue as her stare remained fixed on my cock. Her keen interest caused Mr. Carr to laugh. "You've definitely gotten her attention, Bailey!"

Blushing, Isla returned her attention to her boss. As she stared up at him, the desperation was clear in her eyes. "Please, Mr. Carr, I promise I'll be the best assistant you've ever had. I'll be so good!"

He didn't try to suppress his pleasured moan while she continued jerking him off. "Oh, I know you'll be a good girl for me, sweetheart. But tonight, you're going to be so bad." With those words, he wove his fingers through her hair and guided her to his cock. "Open wide," he demanded. "And while you're sucking my dick, make sure you don't neglect Bailey's."

She took his tip between her lips, making him moan even louder. My own dick pulsed, as if begging for her attention. And my God, she gave it! While sucking off her boss, her hand sought out my erection. I gasped at the feel of her fingers circling my shaft. 

Mr. Carr began gently thrusting his hips, driving himself deeper into Isla's mouth. She made a sound between a gag and a gulp, her hand pumping away at my cock. His hold on her hair tightened as he murmured, "That's a good girl, take a little more! Ah, fuck yes!"

Somehow, she managed to keep jerking me off with a perfect rhythm even while Mr. Carr buried his cock in her throat and held it there. I watched as his head fell back and his eyes fluttered closed. Though he seemed overwhelmed by lust, he readily allowed Isla to pull off when she needed air. 

With tears glistening on her long lashes, she gasped for breath. I was mesmerized by the sight of her breasts rising and falling. Mr. Carr's dick was covered in spit. It throbbed and twitched, clearly ready for more of Isla's mouth. He must have guessed that my own dick was aching for the same treatment, for he now guided Isla to my erection. 

Looking down, I eagerly watched her wrap her lips around me. "Oh, Isla, that's so good!" I groaned.

Instead of releasing Isla, Mr. Carr set the pace of the blowjob she gave me. He moved her head back and forth, making sure she took a little more of my length each time. The pleasure was so intense that I actually whimpered. This woman was incredible at sucking cock!

"Such a dirty girl," Mr. Carr taunted her, "letting us fuck your mouth. You still think this job is worth it?" He pulled her off so she could answer.

"Yes, please," she panted.

He tilted his head, considering her for a moment. Then he looked at me. "Tell me, Bailey, have you jerked off while fantasizing about Isla?"

My face grew hotter as I glanced at the woman kneeling before me. "Plenty of times," I sheepishly admitted.

Mr. Carr positioned Isla at my dick again. She swept her tongue over my tip, gathering up a bead of fresh precum. "And while you were fantasizing about her," my boss continued, "is there something in particular that made you come hard just from imagining it?"

Isla suckled my cockhead, her blue eyes fixed on my face while she awaited my response. "I always shot my load in record time whenever I fantasized about eating her ass," I confessed.

She drew back so abruptly that I feared I'd gone too far; I braced myself to hear her utter the safe word. Instead, she turned her face toward Mr. Carr and squeaked out, "Sir, do you really expect me to do that?" 

In reply, he cupped a hand against the back of her head. My own eyes widened when he simultaneously drew her closer and took hold of his cock with his free hand. Lifting it, he pressed Isla's mouth firmly to his sac. "Suck my balls," he ordered. Witnessing her draw his right nut between her lips sent a fierce shudder through me. "I bet that makes you feel dirty, doesn't it?" he asked her through a grin. 

She only moaned while taking as much of his sac into her mouth as she could. Mr. Carr's breath hitched in his chest, yet he managed to say, "And you'll feel even dirtier when Bailey's rimming you."

I began trembling in anticipation. Could Mr. Carr sense how eager I was? Maybe, for he finally released Isla and moved to join her on the floor. Still standing, I watched as he cupped her face in his hands. The kiss they shared was sensual, with their tongues meeting again and again. 

"Thank you for giving me another chance," Isla said quietly. 

Mr. Carr slid his hands over her bare skin. "You don't have a second chance just yet. You're still earning it." Once he lay down on the carpeted floor, his dick loomed out from him. He ordered Isla to kneel at his side. "Keep sucking my dick and playing with my balls. And make sure you keep that gorgeous ass high in the air so Bailey can enjoy it."

I rushed to kneel behind Isla. When she leaned forward, lowering her mouth to Mr. Carr's cock, I greedily squeezed her buttocks. Though she whined a little, she was quick to resume blowing our boss. Spreading her cheeks apart, I gazed upon her rosebud. My dick started leaking even more precum, and I made a mental note to later clean up whatever mess we made on this floor. 

With a fingertip, I grazed Isla's puckered hole. She moaned, but the sound was muffled by the cock in her mouth. "I'm sorry, baby," I told her in a low voice, "but I just have to do this."

Then I buried my face between her buttocks. She startled beneath my hands, and my lips. I licked and kissed her opening, prompting her to lift her head and mewl, "Oh, my God, Bailey! That's so filthy!"

I only made a sound of agreement while delighting in her forbidden entrance. 

"You little slut," Mr. Carr chided her. "How will you ever look Bailey in the eyes again after letting him tongue your ass?"

I released a guttural groan. My tongue was insistent at her hole, prodding her flesh until she relaxed enough to let me inside.

"Mr. Carr!" she wailed. "Oh fuck, he has his tongue inside me!"

"And you fucking love it, don't you?" our boss shot back. 

Isla let us know just how much by slipping a hand between her thighs and working at her clit. I could hear the sound of fingers against slick skin. Spreading her even wider, I managed to make more progress with my tongue. I reveled in her taste, so different from that of her pussy, but just as arousing. Her ass was primed for this, I realized. While she couldn't have known about my love of rimming, she'd clearly prepared to offer this particular hole for our use tonight. 

She soon began quaking so violently and breathing so fast that it was impossible for her to continue sucking Mr. Carr's dick. He didn't seem to mind in the least. Rather, he sat up and urged her on. "Go on, you naughty little whore, come for us again!"

Those words, combined with my tongue fucking her ass, served to push her over the edge. Her contractions were strong enough to force me out of her hole altogether. When she released a shriek through a series of spasms, Mr. Carr covered her mouth with his hand. 

"Enough of that," he warned, "or I'll keep you quiet with my cock."

She quickly nodded, and after he took his hand away, she let her head fall forward, her body still shuddering. Giving her no time to recover, Mr. Carr drew her into his arms. Effortlessly, he stood and planted her on the edge of his desk. Her face was flushed, and strands of hair clung to her cheeks. Grabbing her legs, Mr. Carr spread them wide.

"Please!" Isla tried to close her legs again.

"Look at her, pretending to be modest now!" Mr. Carr said to me. I only nodded, my stare riveted to Isla's pussy. She was slick and swollen; even her inner thighs were coated with juice. Mr. Carr thrust two fingers inside her, his hand moving so fast that her pussy made wet squelching sounds. Issuing helpless moans, Isla gave me one of her pleading looks, but I simply mouthed, You bad girl.

After withdrawing his fingers, Mr. Carr scooted Isla even closer to him. Then he guided his dick to her entrance. "Tell me how much you want it," he growled. 

"Please, Mr. Carr, give me your cock!" she begged. "I need to feel it inside my pussy!"

He rewarded her with a brutal thrust. With her legs lifted and her ankles resting close to his shoulders, Isla was at his mercy while he fucked her hard and fast. I stared, incredulous as to how he managed to last at that pace. Sweat dotted his brow as his dick claimed her pussy like a relentless machine.

She started crying out, her fingers tugging at her nipples. "She's getting too loud," Mr. Carr told me. "Fill her mouth with your cock."

Isla angled her head closer to the side of the desk, her mouth open and ready for my dick. Gently, I grasped her hair and guided her to me. And then I began fucking her mouth, no longer holding back. The feel of her throat muscles constricting around me made my balls tighten. 

Realizing I might have gotten carried away, I pulled off, both for her sake and mine. She gulped in a lungful of air, her breasts bouncing from the force of Mr. Carr's fucking. Though she opened her mouth wide again, inviting me inside, I merely stroked her cheek. That tender touch prompted her to smile. Locking her eyes with mine, she said, "I want to be a dirty slut, just for you and Mr. Carr."

"Good girl!" our boss said while burying his dick inside her.

Leaning forward, I brought my lips within inches of Isla's. She lifted her head, eager for my kiss, and as my tongue claimed her mouth, I slid a hand between her thighs to rub her clit. 

Almost immediately, she came yet again. Somehow, we managed not to break the kiss even as she screamed from her powerful orgasm. I heard Mr. Carr hiss, for he surely felt those contractions all around his cock. "You won't be satisfied till you have a pussy full of cum, will you?" he panted. Isla whimpered in response, but instead of making good on his words, Mr. Carr pulled out. "Bailey, I want you to fuck her while standing up."

I drew myself upright, more than happy to obey his order. Last week, when he and I were planning tonight's roleplay, he'd made it clear that Isla would be offering me her pussy for the taking. "She'd prefer that you not wear a condom," he revealed. "Is there any reason why you should?"

"No, sir," I'd replied. "My former girlfriend and I got tested before we decided to stop using condoms, and our results came back fine. Since that relationship ended, I've had a couple of hookups, but I always used protection."

It had felt more than a little strange, discussing such intimate details with my boss, yet I was perfectly willing to do so if it meant I could fuck Isla raw.

Now, I was finally getting my chance.

Mr. Carr moved so I could take my place between Isla's legs. I didn't hesitate to enter her with my own hard thrust, and once I was all the way inside, she moaned, "Oh, fuck, you're thick, Bailey!"

"And even after Mr. Carr pounded your pussy," I said in a strained voice, "you're so damn tight!"

As much as I wanted to surrender all control and just rut away, I reached for Isla and drew her into a sitting position. She wrapped her arms and legs around me, keeping us firmly joined. Lifting her off the desk, I cupped her ass in my hands and held her aloft. We shared another fervent kiss before I started taking her with a slow, almost languid rhythm. Unlike Mr. Carr, I wouldn't last if I tried to go faster.

Isla clung to me, holding my stare. "Yes, Bailey, fuck me!" she cried. 

It took little effort to support her petite frame and drive my dick into her pussy. Vaguely, I heard Mr. Carr opening a desk drawer, but I was too caught up in my lust to pay much attention. Again, Isla's lips met mine, and I eagerly returned her kiss. I was dying to be the one to fill her cunt with my cum. 

Mr. Carr moved to stand before me, with Isla's back to him. She let out a surprised squeal, her eyes growing wide. "Mr. Carr, what are you doing?"

"Getting your ass ready for a fucking," he replied simply. It was then that I realized he must have taken some lube from the drawer. "You didn't think we'd leave one of your holes unclaimed, did you?"

A few moments later, my boss ordered me to hold Isla still so he could work his dick inside her ass. Her grip on me tightened, and though she opened her mouth wide as if to scream, she managed to stay quiet.

"That's a good girl," Mr. Carr coaxed, "letting me have your tight little ass!"

When both of us started to slowly, carefully thrust, she moaned from low in her throat. I gritted my teeth, fighting back the urge to come. It didn't take long for me and Mr. Carr to sync the rhythm of our fucking, so we were pumping in and out of Isla's holes at the same pace. I could easily feel the movement of his dick through the thin wall of flesh separating it from my own. 

Isla was completely helpless, held aloft and impaled on our cocks. A sound like a sob escaped her lips, yet she shamelessly begged for our cum. I lasted until she shook in my grip, her pussy tightening even more around my dick with each spasm. Mr. Carr clearly felt it, too, for his thrusts grew shallower, less fluid. 

Finally, I let go, emptying my balls inside of Isla with a groan. I continued shuddering while her muscles milked me dry. "Bailey!" she wailed. "Oh, fuck yes, wreck my pussy!" 

Even after I was spent, I remained fully hard, and I couldn't resist the instinctual urge to keep fucking her. She was slick with sweat, just as I was. When Mr. Carr's eyes met mine over Isla's shoulder, I saw how desperate he was for his own release. Holding Isla tight, he hammered her tender hole, making her slump against me. 

The shout accompanying his orgasm was dangerously loud, but all of us were beyond caring by that point. Lifting her head, Isla wore an expression of sheer rapture. "Mr. Carr! Fill my ass with your cum!" 

"Oh, I am, sweet girl!"

I grew still, my breathing heavy. Once Mr. Carr pulled out, I carried Isla back to his desk and gently set her upon it. My dick slipped free of her pussy, and she looked down at herself, appearing almost dazed. Then a peal of laughter emerged from her lips. "Oh, my God, I have so much cum seeping out of me right now!"

I couldn't hide my triumphant grin, and when Isla held out her arms, I readily entered her embrace. "Bailey, you were amazing!" she exclaimed. 

"You were the amazing one," I whispered.

"And you!" Isla turned to Mr. Carr. Her eyes were bright and full of tenderness as she regarded him. "You had me shaking with trepidation at one point! I hope I never need a real punishment from you."

He laughed, clearly pleased. "Who knows?" he said. "You might enjoy it, baby." 

As I watched them share a deep, lingering kiss, I hoped I would be lucky enough to find a woman as incredible as Isla. If I did, I would shower her with the same adoration Mr. Carr now lavished upon his lover.  

I also hoped I'd be invited to participate in another roleplay session with the two of them, and I might have if Isla hadn't taken a job at another company. While the new position would be a major advancement in her career, her departure surprised me. Yet I learned the real reason she chose to work elsewhere when I received a wedding invitation from her and Mr. Carr several months later. It made sense, both professionally and personally, that she wouldn't want to continue serving as her husband's assistant. 

During that time, a friend introduced me to the woman of my dreams. Like Isla, she was a few years older and stunningly gorgeous. I followed my new girlfriend's advice to take college classes part-time, and she cheered on each of my academic successes.

Together, we attended the wedding the following year. Holding her hand, I watched as Isla and Mr. Carr exchanged vows. Even now, I marveled at the fact that I intimately knew every inch of the bride's body. The smile she gave Mr. Carr was radiant, and my boss had never looked happier. 

Maybe, I told myself, an active fantasy life served to bring a couple closer together. With that thought in mind, I resolved to ask my girlfriend later that night about her deepest desires.

Then I would do my best to fulfill every one of them.