Training the Sales Guy

I kept waiting for the other shoe to drop.

I'd had sex with my coworker. And not just any coworker. Carson Fucking Wells. Straight bro who apparently had a thing for sucking dick. My dick included. He wasn't my direct report, at least, but still...

I spent the next week after our sales visit, I was waiting for a visit from HR. In my more dramatic, worried mind, I imagined being told to leave immediately and they'd send me my personal stuff later. 

But pretty quickly, I realized Wells wasn't gonna blab. He didn't want word getting out about this either. He had even more reason to keep it private, and once the fear and fog cleared from my brain, I realized he was keeping more distance from me at the office. No more stopping into my office to shoot the breeze, no more "Boss" nickname. I was Bill again. 

I was glad, really. I'd had a hot, very hot no-strings experience with a kind of hetero dude and was able to relive those memories now. I even thought about Carson during my next hookup BJ. 30 year old jocky gay guy from Grindr. Not a dead ringer or anything, but I closed my eyes while the Grindr cocksucker deep throated me and let myself be transported back to that Denver Marriott. I even grabbed Grindr guy's head like I did Carson's and start thrusting. 

"You should give a guy some warning," he said when he finally came up from air, admiringly stroking my dong. "You got a big fucking dick."

"Sorry man," I apologized, stroking his dark brown hair. I kind of wished his hair coloring matched Carson's more, which was kind of fucked up. This guy was way cure and way hot. "You got a great mouth."

The flattery worked for him. "OK if I just milk that load out of you?" he asked. 

I knew he'd do a good job, so I nodded. "More than OK. Have at it..."

I was out of the Carson Wells headspace, and I began to enjoy this blowjob for what it was. Some guys on Grindr overpromise their oral skills. This guy wasn't one of the bullshitters. He knew how to go gradual to work up a big of steam, then really go wild and deep on my dong to make me blast. It was awesome.

In our DMs we'd established a no-recip vibe, and indeed I didn't offer to get him off. But I did thank him and praise his ability. It was may be a one off but we both said we'd hit each other up again sometime. 

***

A man can go through phases. In my 20s I tried it all. Well, not every perverted kinky thing under the sun, but when it came to regular vanilla sex, I sucked, got sucked, fucked, got fucked. I tried rimming and frot, though those didn't appeal to me as much. By my 30s, I realized I was much more into topping than bottoming. It was half physical, since bottoming didn't feel fun or pleasurable to me like it did to a lot of guys. But it was that feel of being in control, of doing the penetrating, that got me going. And with the coming of online hookup sites and eventually the apps, I found identifying as a top attracted total bottoms. I thought I'd miss the vers side. Turns out, I didn't. 

My 40s were about being in a relationship. Not a six month thing, or a two year thing, but marriage. I was still processing what had gone wrong with me and Rob. Maybe we fucked up a good thing, or maybe we never should have been together so long. The sex was great, but not perfect. But we'd drifted apart in emotional ways, which was tough. 

Maybe that's why I was getting into the no-strings thing so much. Not being a man whore or anything, but once or twice a month, I found a guy to service me. And truth be told, the temptation was getting stronger. Grindr and Scruff had some dedicated cocksuckers, and I had the kind of dick those guys often went for. 

Maybe that's why I was scrolling through the apps for the second time in a week. Work had been getting me stressed, and maybe seeing Carson had my mind wandering all afternoon. Hell, there were a number of the other younger bros around the office I wouldn't mind sucking my dick either...

"NO GAG REFLEX" came the boast of one. I took this guy's profile with a grain of salt. Like I said, there were a lot of bullshitters on Grindr. But if he was offering...

"Hi man," I messaged. "Fucking hot profile." I was massaging the cock in my sweats. Maybe a quiet evening in wasn't gonna be so quiet.

Up till that point I'd met two men I could really let loose with orally. Rob gave pretty good head, but he wasn't one of them. One was a trick who deep throated me greedily, kind of choking/gagging on my cock, but in a hungry pig kind of way. It was before all the porn videos of that kind of thing, and it seemed crazy and nasty and hot. The other was a guy I went out with for a few month, Steve. He was really into servicing me, and was very open to having his face fucked. So we did that, a lot. He wouldn't do anal, and I think I ended up calling things off with him for that reason. 

Like I say, men go through phases. Now I thought of Steve as the one who got away.

I told No-gag-reflex guy about that now. About my ex-boyfriend who used to do that and how I missed it. 

He boasted how he could really handle some rough throat treatment. "I'll make you forget that ex," came the reply. 

Maybe he thought I was referring to someone more recent and that I was still carrying a torch. It was a hot thing to say though. 

"Hell yes," I typed back. 

"My place or yours?" he asked.

"Either works," I wrote. I looked down at my sweatpants and beat up T-shirt. I didn't feel like going out. "But how bout mine?" I sent him my address.

"Cool," he said. "Can be there in twenty." Then "You might wanna have a towel handy. I've not had any accidents in years, but you're a big boy."

He was probably laying it on thick. I mean, I'm hung big but not like fucking Rocco Steele or anything. Still, I got an old towel and set it out for the ready.

Turns out No Gag didn't need the towel. The dude was a pro. I'll admit he wasn't my normal type physically, but I was glad I'd gone beyond my normal type. He had a fun, horny energy as he walked in and practically begged for me to whip it out. 

I did. 

"Fuuuuckk..." he hissed as he reached down to slowly stroke up the length. "I'm gonna love have this fucker buried down my throat." No Gag had a way of making me feel like a porn king, which I was loving. He looked up with a flirty. "Where ya wanna do this?" he asked.

I tilted my head to direct him into the living room, where two towels were set out. One folded for his knees, the other... well...

He knelt down as I peeled down my sweats. And then he was on me. Nice, hungry sword-swallowing act. He was skilled all right, but part of me was still a little nervous going wild, since I didn't really know the guy and never had done anything before him. I did have one bad Grindr experience with a dude who swore he could deep throat me. He most decidedly could not.

"I'm going in, man," I announced. "Just tap my leg if it gets to be too much."

He mumbled around my cock in a way that communicated he didn't plan on tapping anything. So I held on to his skull and started riding. I didn't go hard at first but I gave myself some deep, slow, and steady throat action. Working in deeper... deeper... till my my nuts pressed against his chin. 

"Holy fuck," I gasped. This felt awesome, amazing in a way I'd forgotten a tight throat could feel. No Gag really didn't seem to have any reflex kicking in. "Hold another second?" I asked, my cock buried deep. He didn't answer, but he didn't tap out. He just held himself calm and still and nursed my dick with his throat. I honestly I think I pulled out just so I wouldn't cum. 

No Gag let out a sound that was a combo of groan and deep intake of air. "Ugh... fuck that's hot," he said. 

I held my dick up, rigid and very wet. "Think we can go for some of the stuff we talked about?" I asked. In our chat, No Gag had messaged some specific things his oral tops often enjoyed doing. 

"Go for it," he growled. 

I nodded, then pushed back in. I gave him a second with my cock buried full in him, then I held his skull and just fucking. Not slow this time, I just pumped his mouth and throat like a fleshjack, getting off on the clutching wetness on my thrusting cock and the slick suction noises. I slowed down just a little and compensated with harder thrusts. 

Turns out he did have a gag reflex after all. Nothing bad happened, but the sucker gagged around my cock a half second, then swallowed around me while I stopped. I pulled out and saw the thicker mucus on my dong. I was turned on as fuck.

"Slower?" I asked. 

He had a determined look. "At first. Then you can go hard again."

I slid my hardon back between his spit wet lips and now felt the drool wet my ball sac with each inward thrust. I tried to maintain something between the fast and the hard rhythms as I pumped his face and looked down in disbelief at the man's feat in taking me. And wouldn't you know? I thought of Carson Wells and that fucking did it. My hips gave a hard jab and caused more gagging sounds. I was already cumming, though, and thankfully the sucker knew how to take me, and let me ride out my O. I relaxed and let go of my grip on his head.

Tears were streaming down his cheek when he finally pulled off, but he looked happy as a clam. "You were horny," he observed.

I looked down and patted him playfully on the cheek as way of thanks. "You made me horny... goddamn, that was incredible."

He stood up, spit on the top part of his sweatshirt, but otherwise not looking worse for the wear. I had an extra towel and handed it to him to wipe off. 

"You do that a lot," he observed as he set the towel down.

I shook my head. "I haven't in years. Thanks for reminding me how much I love it."

No gag grinned. "Pleasure was mine, man. Some guys... well, they can go too hard or too easy. You were just right. "

"Any chance we could do this again?" I asked. 

I was expecting a noncommittal Grindr sure-maybe response, but No Gag shook his head. "Nah, man. My husband gives me a hall pass, but not for repeats."

"Well thanks for using your hall pass on me," I replied. "Seriously, I'm gonna think about that for a while."

***

At first I thought Carson Wells had major misgivings about sucking my dick. It turns out he just didn't want anyone suspecting. 

"Hey Boss," he said as we rode the elevator down one Friday afternoon. If you're familiar with the financial district in summer, you know it clears out each Friday midday. Carson and I were the dumb saps working the full day. 

I was caught off guard by the return of the nickname, but welcomed that Carson and I were on friendly terms again. "Hey Wells, I thought you'd be hitting the links by now."

He shot me his goofy frat-boy smile that worked a little too well on me. "I wish, man. I have a big camping trip with my buddies in a couple weeks, and can't really use up the half day now."

"Well, I guess it's good to put in some face time," I replied. "With Cal in and all." Calvin was the Senior VP and divided his time between the major locations of our firm. 

Carson smirked, like he was pleased to hear me be cynical about corporate politics. "I like this side of you, Boss," he said.

The elevator dinged at the ground floor. At least I could make a getaway. But Carson leaned in before the doors opened. "You've gotten head lately, haven't you?"

I blushed, which made the dude laugh. The doors open and we strutted our way through the lobby and out on to the street. 

Carson pulled out his phone to get an Uber. I was going to do the same but he looked up and shot me an impish look. "You think maybe you can get my weekend started off right?" he asked. 

I knew what he was asking. God, he was hot in his business casual. Golf shirt polo that stretched over his gym-built muscle, lightweight wool slacks, and tan dress shoes. He knew he looked hot, too, the perfect bait for a gay dude like me. 

"Come on, Bill," he urged, his voice a little softed. "No fucking strings.. it'll be fun."

"Yeah," I agreed. Blushing as I did but feeling a surge of horniness that was already making me chub up in my own trousers. 

It was weird as hell going to Carson's condo. Smallish one bedroom, but clean and neat. Very much had that city-dude bachelor pad feel. Just the right amount of sports memorabilia, but decorated like he'd hired somebody for the job. He set down his keys and wallet and phone on the kitchen island and turned to me, his playfulness and easy confidence giving way to some more urgent horniness. I could read it in his face and in those amazing green eyes. 

"OK if we take our time, Boss?" he asked. He was actually a little nervous, which was the thing that put me at ease. And turned me on. "Last time we were a little rushed."

"We were drunk," I reminded him.

"Well, we're not drunk now," Carson reminded. "I wanna enjoy this."

I felt my dick really firming up into a hard ridge. I couldn't believe Wells was gonna give me head again. I'd been thinking about the possibility a lot, but the reality of it was really sinking in. "What are you thinking, Wells?" I asked.

He shrugged. 

"It's a real taboo to suck another man's dick, isn't it?" I prompted, throwing back something he'd admitted to me in Denver. 

He blushed. "Yeah, it is. Big time. No one knows I'm into this shit."

"I do, Carson." I didn't mean to make him uncomfortable or anything. I was glad as hell he'd felt like he could share this sexual side with me. "I gotta warn you... it's been a couple days since I've gotten off. But if I cum quick, I'm pretty sure I could go again."

"For real?" Wells asked, excitedly. That excitement fed my own horns.

"For real, Wells. If you're up for a longer session."

"God, man, yeah, I am." Then. "I can't believe we're fucking doing this, but it's crazy hot," he admitted, and I loved that he admitted it. 

We didn't have the alcohol this time. In some way that made what was about to happen even hotter, but it also lent an awkwardness about how this was going to go down.

"Um.... you prefer to get head standing?" Carson asked. Just hearing that in his bro voice was enough to get me goin.

"I prefer it anyway you wanna give it, Wells," I smiled. This wasn't a Grindr trick, but it wasn't boyfriend/husband sex. Intuitively, I knew to keep up the buddy vibe with Carson, to keep him at ease. 

"Why don't you stand, Bill," he said after thinking a second. "It'll be easier for me."

I followed his lead, watching as his gym built body got settled in on his sofa. I undid my belt and got into the look of anticipation on his face as he watched me unzip. 

"Niiicee," he said as he watched my hard dong poke out. His eyes didn't leave my crotch. "You got a nice dick, Boss," he added.

"Help yourself," I encouraged. I'd really never fooled around with straight or even straight-ish dudes like Carson, so I didn't know how much I should talk or not talk, but the guy seemed to be into an easy rapport. I didn't do anything but put my hands on my hips and let him explore at his own pace.

Carson started with the licking, like he was measuring the hill he was gonna climb. Long swipes up my thick tool, wetting me down in the process. His trimmed beard made him look both younger and older than his 30 years. I imagined him doing this in whatever fraternity house he live in during college. 

I let out a soft gasp when the sales guy finally parted his lips and began going down on me. I didn't know what made Carson Wells tick and maybe I never would, but I couldn't fault his enthusiasm for sucking dick. The guy made love to my cock. There was no other way to put it. Alternating long, wet strokes of his mouth with some suction action, then pulling off to kiss and lick my cock.

"Nice, man," I encouraged. Not wanting to break the spell, but feeling Wells needed some positive feedback for what he was doing. 

He didn't suck me too fast, but I was hornier than I realized and had to think of a million things to keep from coming right away. If Wells wanted to take his time, I was gonna let him.

"You might want to pull off, man," I urged quietly, that gonna-cum tension in my voice.

Carson backed off, giving my dick head a little kiss as it pulled out. A string of spittle connected it with his lips and then broke, landing on his beard. For some reason I found that very hot and my dick spurted out some pre. 

"Fuck," he laughed and leaned in to swoop it with his tongue. "I got you worked up," he stated, not even a question.

"You have," I replied. "I hope you don't mind me saying this Wells, but you're really good at this."

Carson knew what I was getting at. He had a quiet serious expression as he put his hand on his thighs and stared at my prick. "I don't mind, Boss. Thanks." He looked up at me finally. "So... what do you like when you get head?"

"What do I like?" I asked. I wasn't sure exactly what he was asking. 

"Yeah," he said with a grin. "What's your favorite approach... the thing that will get you off hardest."

I let out a heavy breath. "Honestly, Carson... I don't think you wanna know my favorite thing."

He seemed surprised. "Why not?" 

There was something about the sincerity of his response that almost had me telling him. "It's a little more, I don't know... extreme."

He let out a little laugh. "Damn, Boss, I didn't picture you as the kinky type."

I shrugged. "Well, I am... at least when it comes to oral," I replied. "But for real, Carson, I love it all. Just love getting head. You had me real close just now."

That seemed to satisfy the guy. He turned his attention back to my dick. "You into deep throat, Boss?"

"Hell yes, I am," I assured him. 

He was measuring me with his eyes. "It's been a long time since I've sucked one as big as you," he said, matter of factly. "The length but also the thickness."

"Just do what you feel like, Wells," I said. This wasn't some Grindr cockslut, and I wanted him to feel at ease. "But I'd love to see you try."

He nodded. "Yeah, I wanna," he said. Then Carson started taking me in again, going down on me steadily. He reached about the five inch mark, which was the maximum he'd taken so far. Wells paused at that spot, giving some shallow bobs to test out his throat. Then like a swimmer taking that last jump into cool ocean water, the dude just went for it. 

I watched excitedly as Wells buried his nose in my pubes, with a deep grunt stifled in his throat. 

"Fuck yes!" I cried. Then, "Oh fuck, that's hot."

It was too. Because it was this hot finance bro, the coworker I had only professional relationship with. A younger, fit dude who I didn't know, not really. And he was now showing off that deep throat. 

Until he needed air, or a break. He pulled back to suck in some quick air, breathing out a soft "fuck" as he eyed up my spit wet dong. He took a little breather, then went back to it. He now was giving me some genuine deepthroat head. Up and down, about three inches at a time, swallowing to the root on each go. His throat felt snug as hell and the visuals were only adding to my pleasure.

"I'm gonna cum, Carson!" I hissed. This time I hoped he wouldn't pull off. I really wanted to nut right down his cocksucking throat. 

He didn't stop, but rather kept at it. If anything his pace grew a little faster. The sounds got sloppier and I could feel wet spit drip down my balls. That did it. "FUCk!" I cried. I wasn't always a screaming in bed, but I liked to let loose with when a guy sucks me, to give him that feedback. 

Carson pulled off, riding out my ejaculation by sucking the top three inches. Apparently he liked tasting a guy's cum too. Or maybe his throat needed a break. 

He had a proud smile when he pulled off. He knew he'd done a hell of a job, but I also think I was more dick than he'd deep throated before. 

"That was incredible, Bill."

I was catching my breath. "Hell yes, it was," I said. I looked down at my dong which was quickly softening. "I don't know, Carson... you may have completely drained me with that one."

He chuckled, and I think he liked that he'd gotten me off so well. "That's cool, Boss. But maybe we can do this again soon? Sorry if I've been standoffish lately. It's just a little weird... you know, the work thing."

"You know my lips are sealed, Wells," I assured him. "Fuck, I can't let this get out either."

He flashed me that frat-boy smile then broke the postcoital glow. "Listen, Bill. I should probably get ready for the evening. I'm meeting some buddies in a bit." 

"Oh yeah," I muttered as I tucked back in and made myself presentable again. "Well, thank you for getting my weekend off to an incredible start."

Carson stood up to walk me out. I could tell he was still hard in his trousers. I wondered if he was going to jerk off when I was gone or get off later. I thought of asking him, but didn't.

"Just to be clear, Boss," he said before showing me out. "I don't date guys. At all."

"No worries, Wells," I replied. "I'm not looking for a boyfriend. And I get it."

"Cool," was all he said. I got the sense he had some of that straight-dude second thoughts creeping in now. Or maybe coworker second thoughts. 

I tried to downplay anything overly affectionate at that moment. I didn't want to be brusque, but I thought being all business would help him. "See you next week, Carson," I said when he opened the door.

He nodded, then as I walked out, he shut the door behind me.