Training the Sales Guy

by Bill Drake

12 Nov 2023 6820 readers Score 9.2 (153 votes) PDF Mobi ePub Txt


Business travel is OK, until it's not. 

Thunderstorms back east had cancelled one flight and seriously delayed another. Even with the time difference, it was almost 9 when we landed in Denver. At least Carson and I had status and were upgraded to business class. We were the first off the plane, rolling our business carry ons behind us through the airport, making our way toward the rental car area.

Carson Wells is one of the sales guys in our group. The dude's young, about 30, but he's good at his job and moreover has a crazy ambition. It's why he was paired with me on a prospect this big.

I'll be honest, I used to hate the folks in Sales. I felt like we did the work, and they cashed in their commission checks. And Carson was the very type who annoyed the crap out of me. Fratty, capable only of small talk, nice almost to the point of seeming fake. But at times like this I was grateful I was paired with him: the guy didn't get stressed out about travel hiccups.

"I love Denver, man," he said in a tone that would sound chipper if it weren't such a masculine bro kind of voice. "Shame we don't have the time to go hiking or anything while we're out here."

For some reason, I was in the mood for Wells' small talk. "You into outdoor sports? I pictured you as more a country club guy," I teased.

"That too," Carson said as he flashed his smile. Pearly white teeth, fucking perfectly formed dimples, well trimmed blondish-brown beard. Yeah, one reason my defenses were down was because Carson Wells was stunningly cute and stunningly hot. 

Down boy, I thought to myself. It's not like my dick was chubbing or anything, but I knew how to be a professional at work, and with colleagues. Even ones as hot as Carson. Besides, the dude was grade-A hetero.

Carson had reserved the car and we strutted right over to pick up the key. Of course, Carson went for an upgraded model. I thought of lecturing him about costs, but figured I'd let his manager deal with that headache. Besides, if we reeled this big fish in, no one would give a fuck how much Carson ran up on his business credit card this trip.

We were both tired from the long day and once we checked into the hotel it was time to go to our respective rooms and call it a night. 

If you've seen one Marriott you've seen them all. At least this one had a good view of the mountains, though it would be morning before I'd have time to appreciate it. For now, I undressed and brushed my teeth and slipped into bed. I didn't even have my daily masturbation time, I was so tired.

***

The presentation the next day went well. Really well. Carson brought the dynamic sales pitch, and I brought the gravitas. Of course we didn't know what they'd decide yet, but you sometimes get a vibe from a prospect, and that vibe was positive.

Carson was getting it too. We stopped at a trendy restaurant near our hotel that was half steak house, half small plate kind of place. Carson joked it was the kind of place he'd take chicks to if he wanted to impress them. Honestly, I didn't care where we ate. I don't eat a lot on the day of a sales call, and now my appetite was catching up with me. 

"I think this calls for the good stuff," Carson announced as he strutted up to the bar, me a couple paces behind. God, he was so sexy in that post-pitch mode, his 5'11" body filling out his trim-cut tailored suit just right, and those thick thighs leading up to an amazing ass...

"Best bourbon you have," he asked the bartender. Then, he flashed those dimples as he turned to me. "Oh I forgot, you gay guys don't drink bourbon, right?"

I rolled my eyes. "It sounds like you're scripting the next HR compliance video, Wells."

He chuckled. "Is that a yes or no, Boss?" I technically wasn't his boss, but I was an officer, and somehow Boss had become his playful nickname for me.

"Sure," I said, adding that the prospect was ultimately gonna pay for this round.

"Damn straight," Carson grinned, his green eyes twinkling.

We sat the bar, sipping some pretty damn amazing whiskey. Carson had his legs spread, effortlessly manspreading. I didn't stare or scope him out or anything, but let's say I enjoyed the view.

Our conversation was all business as our food arrived, and even as we ordered another drink. 

"Maybe grab another back at the hotel bar?" he asked as we nearly finished that round. It was getting dark out but still wasn't too late. "I'm in the mood to celebrate."

I nodded, signalling for the check. "Sounds good. Only we haven't won the client yet."

"We're gonna win 'em, Bill. You know it, too."

I shrugged. "Yeah," I conceded.

Carson laughed. "Didn't think you'd be so superstitious."

I nudged my leg against his. Hopefully more a buddy nudge than a flirty one, but the booze was loosening me up. "I'm surprised you're not, Wells."

We paid up and made our way back to the boring bar at our boring hotel. It felt great to unwind there. I knew Carson was eager to have more than one other drink, and I wouldn't mind getting a little tight myself. It had been a tough week.

"You're buying this time, Boss," he said. "Just don't order me some well-liquor shit."

I was tempted to get him a cheap domestic beer, just for being a smart ass, but ended up splurging on another top-shelf bourbon. 

"Here's to the Dream Team," he toasted as we clinked our glasses. We were just about the only ones in the bar area, seated on one of the couches. 

"You did great, man," I said. 

He smiled again. Fuck, those pearly whites. "Man, that's probably the first time you've ever thrown me a compliment."

"No it isn't..." I objected. Now that I was in a managerial role, I knew it was my job to provide positive feedback to everyone on my team. 

"For real," he said, with a smile that said he wasn't too upset. Or maybe Carson was just being his frat-boy nice. "You're kind of intense, Boss."

"Oh," I said. Not sure what to make of it. Though Carson wasn't the first person with that opinion of me. 

He nodded. "I'm gonna say something that's not HR-approved... but you've mellowed out a lot since you broke up with Rob."

Rob was my ex-husband. I still couldn't tell if it ended amicably or bitterly. But it had been a big shift in my life. "It was a divorce," I corrected Carson.

"Yeah, divorce. Sorry. I know that was an asshole thing to say. It's just, well, you seem happier now. I hope you are, Bill."

Something about his sincerity, combined with the booze, had me opening up unexpectedly. "There's good and bad," I replied in a measured way. "But the freedom is nicer than I expected."

Carson nudged my knee with his, in what I would have guessed was a flirtation, and gave me a "you dog" kind of look. "I bet," he smirked. Then he got an impish look on his cute face. "Maybe I shouldn't admit this to you, man, but I sometimes have fun with guys."

I gulped. This was major HR-inappropriate territory. "Is that right?" I asked with my best poker face.

The man nodded. The sexual part of my brain was just thinking how incredibly fuckable my coworker was. His voice made him even hotter, I thought. "Not the whole nine yards like you gay guys, but yeah..."

"How do you know what I do in bed?" I had to tease.

He laughed and shrugeed. Again, flashing that killer smile. "You got me there, Boss. Guess I shouldn't make assumptions." We paused and, fuck, our eyes met, like really met. I wasn't imagining it: Carson Wells was fucking flirting with me. "Can I trust you with this, man?" he asked.

I gave some motion of my hand that was some combo of crossing my heart and scout's honor. 

He bit his lip nervously, playfully, and then lowered his voice to almost a whisper. "Um, yeah, I'm into sucking a guy's dick." He blushed as he said it, but I had to be impressed by how forthright he was. It was the last thing I expected from Carson's mouth. His nervousness carried him on. "I mean, just the feel of a hard cock in my mouth.... it's wild, kind of a taboo you know for a guy like me."

"I can imagine," I said. Not wanting to either encourage or discourage Carson. My dick was getting rock hard in my suit. And there was no way it was going down soon.

"Yeah," Carson beamed, glad I wasn't judging him or giving him any flak for his bi streak. "I mean it's crazy, I don't even need my dick sucked or anything, just that act is enough to get me going, you know?"

I nodded but replied. "Not exactly, Carson. I guess I'm more a receiving is better than giving kind of guy," I joked.

"Did Rob do that for you?" he asked.

This was definitely inappropriate conversation. But fuck it. "That and more," I replied. "Rob was a big ol' bottom."

"Hot," Carson said. There was something weird about our dynamic now. Buddy-buddy, but also like lusty. Carson took a sip of bourbon, but he was nearing the bottom of his glass. "Another round, Boss?"

I held mine up and swirled the last half centimeter of brown liquid in the rocks glass. "I shouldn't, man." I was already pretty buzzed.

"Come on," he urged. "We're the fucking Dream Team."

I caved and nodded. If my boner was riding a good ridge in my trousers it downright throbbed watching Carson's hot suited body get up and strut over to the bar. I needed to find some self control, in case Wells was actually gonna proposition me. Maybe he just wanted someone to talk to about his bi side. Or maybe he liked teasing me as an ego boost. 

He was all smiles when he came back with two more drinks. We clinked glasses and had our first sips. "To a killer day," he smirked.

"Yep," I said. I wasn't drunk at least. But I was starting to feel really nice.

He looked around. I thought he was just idly checking out our environment, but I realized he was seeing if the coast was clear. His eyes flitted back to my crotch. 

"You look like you're packing a lot down there, Boss," he said. That sexual edge somehow changing his frat-bro voice. 

"Sorry," I muttered. Trying to cross my legs.

"Don't hide it, man," he urged. "No one can see it from a distance, not in those pants."

I blushed as I spread my legs again, manspreading as I faced this hunky sales guy. This was so wild and wrong, but my dick was rock hard. 

"Nice boner, Boss," he smirked.

"Thanks," I said. Maybe I thought if I limited my words there'd be less cause to get me fired.

"How big is it?" he asked.

"How big?" I chuckled. Wells was the last dude I imagined to be asking me for my dick size. "7 and a half," I replied. "I've not measured the width."

"It's pretty thick," Carson put out there, his eyes back on my boner. "But not too fat to suck."

"Jesus," I exhaled. 

Carson's green eyes twinkled. "Am I getting you worked up, Boss?" Jesus, he loved flirting all right.

"You know you are, damnit."

"This is just between us, right?" he clarified.

"It better be," I hissed. "Not how I expected this trip to go..."

"You upset?" he felt me out.

"Depends on if I'm thinking with my brain or my dick," I answered honestly.

That made Carson smile. "How bout your dick?"

"My dick wants to get sucked," I said bluntly.

Carson nodded, almost serious, maybe the reality was making him less chipper. "Let's do this, Bill," he grunted and tossed back of the liquor, like he was building up courage.

I didn't do mine like a frat boy shot, but sipped a good amount of the remainder and set the glass down before standing up, just hoping my erection wasn't too obvious.

I couldn't believe this was actually gonna happen. Carson didn't seem to believe it either. We rode the elevator silently, almost scared to look at one another. Then he followed me to my room. 

My heart pounded, because I didn't know how this was actually going to go down. I didn't want anything messy with my coworker - hell, I'd probably be the senior investment guy brought in for half of Wells's prospects - but it was probably too late for that. 

I tried to think of how this would go down. For a half minute, a part deep in my brain wanted to put a stop to this. But as I walked to where our rooms were, adjacent to one another, I stopped at mine and Carson looked at me with a look of horny expectation behind his straight-bro smile. I tapped the key card and ushered him inside. 

The thing that helped my conscience somehow was that Wells didn't kiss me or make any move to make out with me. Like he'd had some practice, he crouched in front of me, looking incredible in his slim-cut suit and gym-toned build, wasting no time reaching forward ot unbuckle my nelt. This wasn't gonna be a messy office place romance, this was just going to be a blowjob. As no-strings as they get.

"Fuck!" I hissed as the zipper came down and Carson tugged my boxer briefs below my hard prick. My dick jerked to attention, harder than I recall it ever being. This felt naughty and sexual in a way that made me half-glad to be a divorced man. 

"You sold yourself short, Boss," Carson teased as he ran his finger up and down my bone. "You got an amazing cock." 

And like that, the sales guy was taking me into his mouth. 

This wasn't Carson's first dick. It wasn't his fifth. The dude wasn't lying, he loved sucking cock, and it was clear he'd had some practice. I just stood there, hands on my hips and let him do his stuff. I got off on the mind-fuck of co-worker sex and the straight-dude fantasy come to life. I mean, Carson Wells clearly wasn't 100% straight, but he was as close as I'd get to having a hetero guy blow me. 

And the fact he loved this, really loved this, meant I was getting quality head. Regular, half-suction mouth strokes up and down about four or five inches of my cock, with increasing base. 

"It's not gonna take me long," I warned him. If it hadn't been for the bourbon I would have nutted already. Wells was that good. 

He was going for it now, kind of twisting the base of my cock with his fist as he bobbed more frantically. I placed my hand on the top of his skull, and that got an excited, deep moan from the guy. I started small thrusts timed with his sucking. Nothing too intense, I'm not an asshole. But I was getting real close, and my excitement was pushing me over that finish line.

"Oh shit! Oh fuck!" I hissed, trying not to be too loud. My cum was incredible. Maybe because Carson did this sucking thing all through my ejaculation that just added to the pleasure. My knees buckled a little.

I was finally was spent, and Carson gave one final lick at the tip before pulling back. "That was hot, Boss," he hissed, mouth full of cum and saliva. 

"Damn... it was, man." I looked down. "Need me to get you off?" Once I cum I'm usually out of sex mode. But I know how to take care of a guy's needs. 

He shook his head as he stood up. For real, Carson had a hardon riding up his suit pants. Not as big as mine but showing a good tent. "Nah, I'm good... I'm gonna go back to my room now, if that's OK."

It wasn't awkward as it seemed for some reason. Maybe because my swimmers were in Carson's belly now. "Yeah, that's fine... if you're sure." I felt a little guilty for the no-recip thing. But not too guilty, I suppose.

He flashed a grin. "Yeah, I'm sure. See ya bright and early tomorrow?"

"Yeah," I nodded, tucking back in and pulling up my trousers. "Have a good night, Wells. And thanks again." I was tipsy but maybe sobering up some now. 

"My pleasure, Boss," he said. He paused and looked at me, and God I half expected a kiss to come right then. But he patted my arm and then walked past to the door. And left me in my room. 

"Fuck!" I growled, and had to laugh at how crazy it was I just let that happen. I knew I'd made a terrible mistake, but Carson seemed game to make it with me. And I knew if I had that chance, I'd make it again. 

by Bill Drake

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