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Dirty Dealing - Part 1

"Nick is propositioned by his sister's boss."

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I sat at the bar, staring forlornly at the beer in my hand. When the bartender cast me a sympathetic smile, I realized I probably looked like something straight out of a bad country song.

I'd wait five more minutes, I decided. Already, I knew it was no use; I'd been sitting there for half an hour, with no reply to the text I'd sent my date. At least the place wasn't busy on that Wednesday evening. I didn't think I could stand a noisy crowd right then.

Just as I finished the last of my beer, I heard someone call to me. Looking up, I saw a man regarding me with a smile. It took me only a few seconds to recognize him as my sister's boss, but I'd be damned if I could remember his name.

His smile faded a bit. "It is Nick, right?" he asked, sounding a little unsure.

"Yeah, great to see you again!" I stuck out my hand to give his a firm shake. 

Sitting down on the barstool next to mine, he said, "I'm Trey, by the way."

"I knew that," I replied too quickly, then flashed a guilty smile. I'd always been a horrible liar.

"To be fair, we've only met once," he pointed out. While he ordered a Vodka Soda for himself and another beer for me, I thought back to that initial meeting. It was on my sister Denise's birthday two months ago, when I'd stopped by her office to take her out to lunch. She'd insisted I meet Trey, whom I'd already heard plenty about. My sister thought the guy walked on water. At twenty-five, Denise had started at the company with little experience, and Trey had taken on the role of her mentor. 

I'd chatted with him just a few minutes that day, so it surprised me that he now remembered my name. Having shown up at that office straight from my blue-collar job, I'd appreciated him treating me as an equal during our brief conversation. He wasn't at all arrogant; instead, he showed genuine interest in my answers to his polite questions. 

Furtively studying him, I guessed he was in his late thirties, about ten years older than me. Tall and fit, he had dark hair and expressive brown eyes. Though I was happy to sit and chat with him at the bar, I couldn't help but be a little nervous. Last week, Denise had told me she was up for a promotion that would significantly advance her career. It would be Trey who decided whether or not she got it.

I'd have to be careful not to put my foot in my mouth, I told myself. I didn't want to do or say anything that might hurt my sister's chances.

"So," Trey said once our drinks were placed before us, "are you here alone?"

"I am. I got stood up, actually."

"Ah, sorry about that." His smile was similar to the one the bartender gave me a little earlier.

"Wouldn't be the first time," I sighed. "Online dating is fucking brutal." As soon as the words were out of my mouth, I cringed. "Pardon my language."

Trey's smile widened to a grin. "You're fine," he assured me before taking a sip of his drink. "My divorce was finalized earlier this year, but I haven't yet worked up the nerve to get back out there and try meeting someone new."

"I'm sure you'll have an easier time of it than me."

He lifted an eyebrow, his expression curious. "Oh, and why's that?"

Giving him a quick look up and down, I thought the reason was obvious. The man was good-looking and obviously successful, dressed in that tailored suit. As he shrugged out of his suit coat and placed it on the stool beside him, a woman walking by gave him an appreciative stare. 

Still, I couldn't very well blurt out that he was easy on the eyes and looked rich, too. So I simply nodded toward the woman. "You've been here just a couple of minutes, and you're already attracting attention."

Trey gave her a mere glance before redirecting his attention toward me. "How do you know it's not you she's interested in?"

With a snicker, I replied, "Believe me, I know."

"Don't be so sure."

As his gaze swept over my body, I found myself squirming a little. Due to my physically demanding job, I had a muscular build, and I liked to stay active even when I was off the clock. Tonight, I'd worn jeans and a polo shirt. My light brown hair had recently been cut, and I kept my beard neatly trimmed. I thought I was attractive enough, but forging a connection that went beyond a hookup seemed impossible for me. 

When Trey's eyes met mine again, he leaned a little closer and said, "You have plenty to offer."

I wasn't used to compliments, especially from a guy. My friends and coworkers were far more likely to bust my balls. This conversation with my sister's boss had me feeling strangely flustered, but I feared coming off as an asshole if I ended it too quickly. So I simply forced another smile and told Trey, "I appreciate the vote of confidence."

Slowly, he turned his glass around on the bar top, appearing lost in thought. "You know, Denise is up for a promotion."

The sudden change in topic threw me even more off balance. "She mentioned it, yeah." My tone was cautious as I tried to figure out what Trey was getting at.

"She's told me what a good brother you are." Leaning even closer, he dropped his voice to a murmur. "So I think it's only fair to let you know that you could help her advance at the company."

I knew my face revealed my bewilderment. "Me? How in the world could I help Denise with that?"

Trey placed a hand on my back, guiding me toward him, and I offered no resistance. With his lips close to my ear, he whispered, "By letting me suck your dick."

My eyes widened in disbelief. For a long moment, I was so stunned that I didn't move at all. I simply sat there and let him keep his hand on me. It was only when I noticed the bartender giving us a curious stare that I realized how close, how intimate, Trey and I must have seemed.

Quickly, I shrugged off his touch. My laugh sounded shaky. "You're a funny guy."

"Oh, I'm not joking." Holding my stare, Trey added, "If you let me, I promise Denise will get that promotion."

It was difficult to go from being on my best behavior to being visibly outraged. I ended up landing somewhere in the middle of the two extremes. No longer smiling, my voice was steely as I told him, "I'm sorry if I gave you the wrong impression, but I'm not into guys. And furthermore, I think it's very inappropriate for my sister's boss to proposition me."

"It is," Trey readily agreed. "And it's probably inappropriate for me to tell you that I've fantasized about sucking you off since the day we met."

I had to take a deep breath to calm my growing fury. "And if I say no?"

He shrugged. "Then your sister will stay where she is at the company. In a few years, she might be considered for a more lucrative position."

My jaw was painfully tight. It was all I could do not to deck this fucker. His frame was wiry and athletic, but I still could have easily snapped him in two.

It was the thought of Denise, so sweet and hardworking, and the first in our family to really make something of herself, that kept me from indulging my violent impulses. I understood how much this job, and how much the man sitting beside me, meant to her. She'd be heartbroken if she knew what he was really like. 

Would she be even more heartbroken if she knew I had the chance to help her and didn't?

Reluctantly, I inclined my head toward Trey. "So if I let you suck my dick, you swear you'll promote Denise."

His eyes locked with mine. "I give you my word."

"Good, because if you go back on it, I'll beat the shit out of you. Are we clear?"

"Absolutely." Searching my face, he seemed to sense I was about to capitulate. "Do we have a deal, then?" His voice was low, almost coaxing.

I took several large swallows of my beer, then set it down and said, "Let's go."

"Where to?"

"My place." No way in hell was I driving out to whatever ritzy neighborhood this guy called home. The sooner this was done, the better. And afterward, I wanted to go straight to bed and forget the night ever happened.

Once Trey took care of the tab, we left the bar in silence. Only when we were in the parking lot did he say he would follow me to my apartment. I simply nodded in acknowledgement, for I didn't trust myself to speak. My anger still simmered, ready to reach a boil at any moment. 

During the drive, I kept glancing in the rearview mirror, hoping Trey would change his mind and drop out of sight.

But he stayed right behind me.

Ten minutes later, we stood in my living room. Before heading out that evening, I'd tidied up the apartment. I always wanted to make a good impression if I happened to bring a woman home. Now, Trey looked around and said, "You have a nice place."

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I grunted in response. In the lamplight, I took off my shoes, and he did the same. I didn't offer him a drink; the last thing I cared about was making him feel welcome. Instead, I sank onto the couch and said in a flat voice, "Let's get on with it."

When Trey removed his tie and draped it over a nearby chair, I figured he was just getting more comfortable. But then he started unbuttoning his shirt. "What are you doing?" I demanded.

He paused, his eyes meeting mine. "Getting undressed."

"You don't need to get undressed to give me a blowjob."

"But I want to," he said, simple as that. Again, I clenched my jaw while he stripped naked. My stare moved wildly around the room in a desperate attempt to avoid settling on his nude body. 

When he finally approached me, I couldn't help but notice he was semi-hard. I expected him to kneel on the carpeted floor in front of the couch, but he surprised me by sitting down at my side. My throat tightened as he started languidly stroking his dick.

"Do you want to take your cock out?" he asked in that low voice I already found familiar. "Or do you want me to do it for you?"

With a sigh, I unbuttoned and unzipped my jeans, then pulled them down my thighs, along with my boxers. Unlike Trey, who was now fully erect, I remained flaccid. But I'd only agreed to let him suck me off; I made no promises to be hard while he did so.

A glance at his dick let me know he was about six inches long. At my hardest, I was just over seven inches. I'd made sure to take care of the manscaping earlier, so my pubes were trimmed and my balls were smooth. Trey, however, was shaved bare. 

He didn't ask for permission before kneeling on the couch. With his legs folded beneath him, he gently grasped my cock. I tensed at that first touch, waiting for him to begin stroking. 

But Trey leaned forward and buried his face in my crotch. I heard him inhale deeply as he nuzzled me. The moan he released was full of such satisfaction that it made my skin flush. No woman had ever done anything like this to me. 

Finally, he took me in his mouth, seemingly unfazed that I was soft. Leaning back, I stared at the ceiling. When he began sucking my tip, I had to admit it felt good. All the while, he stroked my shaft as leisurely as he'd handled his own. It was clear the man was in no rush.

Despite my lingering resentment, my body responded to his attention. It felt like a betrayal, the way my dick started hardening. Encouraged, Trey slid his tongue from base to tip. When he took more of my length between his lips, his moans grew louder, filled with blatant arousal.

I didn't want to look down and see this guy with a hard-on blowing me, but it was as if I couldn't resist. I expected to be repulsed at the sight of him working his way farther down my shaft until his lips met his hand, which was circled around the base. Instead, I let out a faint groan. It was impossible to deny how incredible his warm, eager mouth felt. In the very back of my mind, I allowed myself to wonder if it was his abject desire for this act, and for me, that made my precum start flowing.

Trey pulled back far enough to swirl his tongue over my cockhead. Enthusiastically, he gathered up a fresh droplet of the clear, thick fluid. Gazing down at him, I watched his eyes close in utter bliss. He paused only long enough to whisper to me, "You taste so good!" Then he went back to coaxing forth more precum. 

I let out a pleasured sigh at the feel of his tongue probing my slit. By this point, I was fully hard, and when Trey fondled my balls, my breathing quickened. 

Lifting his head, he met my stare. "I want you to fuck my face." Seeing my brow furrow in confusion, he was quick to elaborate. "Grab my hair and drive your dick into my throat."

I'd never been the type of guy to get rough during sex. When a woman went down on me, I let her set the pace, and if I placed a hand on her head, it was only to stroke her hair. 

But this guy? This guy had pissed me off with his manipulation. I was still furious at the way he'd used my sister as a bargaining chip. If he wanted it rough, I was definitely in the mood to oblige his request.

Gripping a handful of his hair, I guided him back to my dick, which he'd left coated with spit. When he readily circled his lips around me, I pushed him downward. At first, I moved slowly, listening for a gagging sound as his mouth inched toward the root of my cock.

Holy shit, he took it all! My eyes widened in astonishment. Feeling my cockhead buried deep in his throat made me groan with my own lust. "Ah, fuck, that's good!" I held Trey there for several seconds, reveling in the sensation of his muscles constricting around my girth.

When I reluctantly pulled him off so he could catch his breath, our eyes met. Whatever he saw in my face made him grin in triumph. "More," he said.

So I gave him more. At times, I moved his head up and down while he kept his lips wrapped around my cock. And at other times, I held him firmly so I could buck my hips and thrust deep into his throat. 

"Yes, yes, take it all!" I growled through gritted teeth. He had me so damn hard!

When I pulled Trey back for another short break, I noticed his eyes were watering, and a strand of saliva escaped his mouth to settle on his chin. His lips looked swollen. I felt a rush of remorse for being so brutal, but even as he gasped for breath, he wore that same smile.

Reaching for the hem of my shirt, he slowly lifted it upward until I seized his wrist in a punishing grip. "Let me see you, Nick. Please," he begged.

I didn't know why I released him and then pulled the shirt over my head. Maybe it was residual guilt. I didn't try to stop him from sliding his palm over my chest. As he planted open-mouthed kisses on my belly, a tremor went through me. His mouth traveled lower until it hovered directly over my rock-hard dick.

Trey again took me deep, sucking and moaning. That renewed stimulation drove me closer to orgasm, for as much as I hated to admit it, face-fucking this man had excited the hell out of me. 

"That's it," I said in a guttural voice. "Be a good cocksucker and swallow every inch!"

I heard him struggle to suppress his gag reflex as he obeyed my order. Without thinking, I rested a hand on his back. When he'd undressed earlier, I'd gotten a glimpse of his ass, which put any woman's to shame. No man should have an ass that fine, I told myself. Now, my hand slipped down to caress it.

My touch caused Trey to let out a needy whimper. Of course, the sound was muffled by my cock in his throat. Squeezing his flesh, I warned, "I'm close!"

I was so ready to finish in his mouth. In fact, I was dying to, and Trey had to sense that. He was still fondling my balls, so he must have felt them tighten.

Yet he lifted his head, tilting his face upward. My cock pulsed, as if to draw his attention back to it. Through his heavy breaths, he said, "That promotion Denise is up for..."

My entire body tensed. "What about it?" 

Trey flashed a wicked grin. "I would have made sure she got it regardless of what you decided tonight. In fact, I've already let the higher-ups know. She'll be hearing the good news tomorrow."

I stared at him, stunned into momentary silence. Fresh anger threatened to overwhelm me when I realized I'd been played. Only my desperate horniness kept me from losing my temper. Shaking my head, I actually laughed. "You fucking asshole!"

"I have an asshole you can fuck," Trey replied, his tone seductive. My laughter abruptly stopped. Remaining still, I watched as he moved to straddle me. I felt his hard cock brush against my skin, so close to my own dick. 

I knew I should have shoved him off of me, but I found myself resting my hands on his hips instead. He grasped the couch on either side of my head, then leaned forward. At first, I thought he would try to kiss my mouth, and I quickly prepared to stop him. Maybe he discerned my tension, for he brought his lips close to my ear and whispered, "Tell me you want to fuck me, Nick." He began suckling my earlobe, which sent a current of hot lust directly to my cock. 

I closed my eyes, breathing faster as Trey reached between us to stroke me. His voice was low and persuasive when he spoke again. "If you liked fucking my mouth, you'll love my ass. Don't you want it?"

The feel of his mouth on my neck was enough to obliterate all resistance. "Yeah," I murmured. "I want it, Trey."

Published 
Written by Obsolete_Fox
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