Training the Sales Guy

Again this story has some edgier, more extreme oral play, with each chapter going a little further.

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It was crazy hot seeing my straight bro of a coworker get into more extreme oral sex.

We had only two accidents. It was inevitable, I guess. The first one killed the mood. 

Carson and I had been doing the Countdown Game, modeled after that video I'd sent him. The first two times we'd done it had been crazy hot, and Carson loved the challenge of it. I'd have him deep throat me and then I'd count off the seconds. The first swallow would go for one second, then Carson would back off, take a one-second pause and a deep breath, then I'd instruct him back on my hard cock. Swallow Two would go for two seconds, the third for three, etc. 

Carson worked up to 5 seconds without too much difficulty. He was getting even better at deep throating my big dick, and his excitement fed off the game to drive him to do it with even more enthusiastic. 

Rounds 6 and 7 were tougher for him, but I assured the straight-ish sales guy he could tap out at any time. I'd push his limits, but he had the ultimate say. By the time he did, we were both so worked up, I was able to do some quick face fucking to blast off straight into Carson Wells' stomach. The sight of that heavy mucus on my dong when I pulled off was just the cherry on the sundae.

The third time we played the Countdown Game, Carson went for more, and fuck, I was so turned on watching him struggle to fight that gag as he held himself pressed into my pubes. Carson wore an old, beat-up T-shirt that he didn't mind getting messy. Usually that meant that thick mucus that dripped from my cock when I pulled out or ran down his chin. But when I urged him to go for round 8, his ragged breath muttered a cry and when he took me in again, poor Carson didn't make it three seconds before he lost it.

I felt bad, and yeah I lost my hardon as I got an extra towel and a wet washcloth to help clean up. Worst was, Wells seemed pretty distraught. 

"I think I'm done, Bill," he said. "Sorry." He was still hyperventilating some, trying to steady himself. 

So much for the Countdown Game. 

I went into full buddy mode, though. Finding him a spare T-shirt and offering to get him an Uber home. Telling him it was OK and thanking him for being a trooper. Everything in the tone of my voice told him I was OK if we stopped the more extreme throat training from here on out, and I meant it.

Thankfully Carson reached out to me next Saturday. I was glad as hell. I was getting used to my time with the guy and didn't want to get cut off cold turkey. Maybe I'd get back into doing hookups or even going on a date, but Wells was tapping into my deep fantasies and I was going to ride this suck buddy arrangement we had. 

I let Carson do the work next time. Hands off, classic standing while he sat and sucked position. He was great at it, and I think the sales bro was showing me that this was as good as me taking charge of his throat.

It almost was. The slower pace did wonders for me, as I let Carson work me up gradually to a heavy cum, alternating deep throating with some more vigorous sucking. 

"FUCK!" I cried. Sometimes I liked being vocal to let Carson know how deep of an orgasm he was giving me. I didn't have to play up anything that day. I reached behind his ear to massage his soft hair as he nursed the dribbles from my boner and worked toward his own big O.

"Thanks, Boss," he muttered when he finally pulled back. I could tell he appreciated that I'd let him do something less intense.

"I told you, Wells, your blowjobs are incredible."

He had a proud look. There was some kind of straight-dude competitive thing that meant Carson gave cocksucking his all. I didn't fully get it, but I loved every hookup we had.

***

All of November it was business as usual. Me acting professional with Carson at work, then Saturday meetups for a BJ from the guy. Once was on his 31st birthday and before he swallowed my cock, he muttered, "You gonna give me my present, Boss?" The more Carson and I did this, the more relaxed we got around each other, fitting into complementary roles. I played up the big bro, encouraging type, and Carson was the eager beaver into how much he got me off - and still riding that taboo that he was into having a dick in his mouth. 

The guy made no move for anything else, either. No kissing, no touching. I checked in from once again to see if he wanted reciprocation. After all, Carson hadn't told me he was dating anyone. But he just assured me he didn't like the idea of a guy doing anything for him. That was the last time I'd make the offer.

We were back to a new normal. Carson had perfected his deep throating and loved to show it off for me, but otherwise our pairings were vanilla again. 

I gave him a wide berth at the office, but not avoiding him so much it looked suspicious. And for the time being we were paired with other people on sales visits, so no business trips together. The "Dream Team" would have to wait.

Still, when our annual holiday office party rolled around, I found myself talking to Carson. First with a few of the younger guys around, then just us two, alone. He was trying to keep his poker face on, but he had a naughty smile as he looked around the bar area. He was drunk, and I was getting there myself. 

"So Boss," he leaned in to say. "I got a Christmas present to give you at some point."

"Yeah, Wells?" I replied with a grin. Maybe he had an actual, physical present, but that would be weird, and I had an idea of what he was getting at.

He nodded. Then he said in a deep fratty whisper, "It's been a while since we've done the Countdown Game."

Holy fuck. I'd have to will myself to keep from throwing hard in my suit trousers. I was gonna chub big time as it was. I looked to read his face. "It has," I said. Then, "We don't gotta, you know."

"I know," Carson nodded. "But I keep thinking about it. I figure I know the worst that can happen." He paused to read my expression. "But if it freaked you, Boss, I get that."

"It didn't," I assured him. "Um, stuff happens."

Carson nodded and that naughty look on his handsome face returned. It blew my mind that he was so into a guy using his mouth. "So you wanna, Boss?"

I nodded, taking a sip of my drink. "My place or yours, Carson?"

"Mine," he said. "Give me a ten minute head start?"

"Yeah," I replied, blushing and feeling my heart pound. We were really going to do this.

I went over to make small talk with two of the client service people in our department. I tried not to be obvious, but out of the corner of my eye, I watched Carson rejoin some of the younger people before finally taking leave. It took me longer than ten minutes to extricate myself from the conversation I was having with a couple of married coworkers, but soon I was giving my good night and texting Carson as I hailed a cab.

The guy had a big playful smile as he showed me into his condo. I saw a couple of towels laid out on the floor, and I gathered that Carson wanted the head start not only to keep us from being connected by our coworkers but to set up. 

"Hey," I said, feeling a good deal of naughtiness myself. It wasn't quite like that first time in the Denver hotel room, but it still blew my mind that I was having a suck buddy affair with Wells. "I thought you would have changed out of the suit."

I almost regretted saying it. Carson's had an incredible body that filled out his suit pretty damn well. He had a muscle build that you wouldn't think would be in a slimmer cut suit, but the combo was incredible. 

Carson just grinned and replied, "It reminds me of our first time in Denver, Boss." Damn, he was on the same wavelength all right. He tugged at the knot in tie. "This is a new tie, though," he added, starting to remove it. "The rest I can get dry cleaned if I need to."

I was getting hard. I hoped Carson wouldn't have any real issues today, but the idea that he didn't seem afraid of the possibility was kind of hot.

He draped his tie over a chair then knelt down on a folded towel, his body looking both bigger and smaller beneath me as he got in cocksucking position in his suit. As I stepped up, he ran his hands up my own suit trousers, not feeling me up really, more just going right for my cock. "OK if I suck a little to get started, Boss?" he asked, already unzipping me and reaching in to fish out my boner. "You know, prime the pump?"

"Have at it, Wells," I assured him, feeling my erection throb in his touch, which paled to the wonderful sensation of his mouth slowly going down on me.

Carson was worked up and more than a little relaxed from the booze, and he got into it. I almost thought he'd chicken out of the Countdown Game and just suck me off the old fashioned way. But finally he pulled back and licked his lips. Carson took a deep breath and looked up at me, green eyes looking excited. "All right, Boss, I'm ready."

My dick was wet with his spit and rock hard. "You sure, Wells?" I teased, but also giving him an out if he wanted.

"Yeah," he replied. "Go for it."

"All right," I said. "Go...."

Carson leaned forward and gave a soft grunt as he swallowed me to the hilt. The first couple were always tough for him, as he retrained his throat to accept my thickness. Still, he knew he had this, and I knew he did, too, sucking me all the way down to the pubes. It was hot as fuck to watch. 

"One..." I counted, and just as gradually, Wells pulled back. There was a soft plop when he pulled off.

"Hot..." Carson muttered.

"All right," I said, in implicit instruction for him to go down on me again. He nodded and once again took my dick into his mouth. He was still working me slow, and once he was there, I counted. "One... two...."

He backed off, eager for air. I was getting a little nervous how this was going to go this time. It had been a couple of months since we'd done this, and the last time it hadn't gone well. I didn't know for sure what was going on in Carson's head, but the fear of retching might be a problem in itself. 

"Just remember, you can tap out any time, Carson," I assured him. 

"I know, Boss," he replied. "I've got this." He didn't wait for my instruction. Already he was going for another round.

"Fuck!" I muttered, then remembered my job. His nose was already mashed in my crotch fur so he'd been getting an extra second out of this one. "One... two.... three..."

Wells had a proud grin when he pulled off. He was more composed and focused now. I didn't countdown when he was off my cock, but in my head I gave as much time off as on. So, once I hit three seconds in my head, I nodded. 

"All right, Wells," I said. 

Carson licked his lips then went down on me, faster this time. He was getting used to deep throating now, and within a second he was all the way down to the base.

"One... two..." I slowed the count just a little, getting off on Carson's self-control. "three... four..." 

"Fuck," the guy said after he came up and took a breath.

"Too much?" I asked, checking in.

"Nope," he assured me, though not taking his eyes off my cock. He was getting ready for round five.

"Have at it," I said finally.

Now that he'd tamed his gag reflex, it was a quick descent. I realized Carson was working on a faster deep throat so he'd have more breath for the countdown. I don't know why I hadn't thought of suggesting that in my training. 

My voice was getting a horny edge now. "One... two... three... four... five..." I didn't stretch out the count this time. I figured poor Wells had more ahead of him.

He pulled off, face flushed. I looked down to see him in his youthful handsomeness, trimmed beard soaked in his spit, his chest puffing out his dress shirt and spreading the lapels of his suit coat.

"Go..." I said again.

This time was even faster. Carson practically speared his own throat with my hard cock.

"One... two... three... four... five... six..."

He was feeling it now, but when he pulled back he gave a satisfied nod, even as some saliva dripped down his bearded chin. He started to wipe it off, but I urged, "Leave it." He looked up at me, green eyes twinkling. "You're a kinky fucker, Boss," he laughed. 

"Pretty much," I laughed in agreement. The moment broke the spell a little, but that was a good thing, since it gave Wells more recovery time. 

I let him take the initiative to get on me again. Descent number seven was slower, which made the countdown tougher for him. By the time I got to six he was struggling some, face going red and tear running down his cheek. "Easy..." I assured him, between counts six and seven. But he made it to the end and pulled off quickly, sucking in some air. I was realizing the deep breaths were less about air than about Carson reestablishing his own sense of bodily control.

Silently, in my head I counted to seven, then gave a stern but reassuring, "All right..."

He'd learned his lesson too well. He speared his throat with my dick once more, only that was the wrong move. "One..." I started and then Carson's gag reflex kicked in. I expected him to pull off, in defeat. I didn't think it was a full on retch gag, but it threatened to be. 

Only the guy mustered his willpower and swallowed it all back, keeping himself fully buried in my pubes. "Holy fuck!" I gasped, then realizing Carson was going to keep going, I resumed my count. I gave him the benefit of the seconds he'd been down on me. "... four... five... six..." Wells was entering his zen state. Having suppressed his gagging once, he was keeping calm and steady with my cock lodged deep in his throat. "seven... EIGHT!" I emphasized the last number to acknowledge the achievement Wells had done. 

He pulled off not fast, not slow. It was like he was afraid anything sudden would trigger something. I watched in excitement as big string of mucus connected my cock head and his lips, till it broke from my dick and landed on Carson's dress shirt, instantly darkening the pale blue cotton. 

I hadn't been close to cumming, and the alcohol I'd had that evening would probably insure I wouldn't real soon. But this was the first time I felt that telltale tingle in my nuts. I'd been so focused on Carson's progress, but now I was getting really fucking turned on. 

He started to wipe off his chin but remembered my preference to see it all dripping and stopped himself. He took a few deep breaths and steadied himself. 

"Another," I said. I didn't let him get to eight seconds off.

He had a real determined look on his face as he swallowed me again. I think the mucus-y spit helped lube the descent and very soon he was deep throating me. "One... two... three... four... five..." Carson was quivering, face turning red again. "You got this buddy," I assured him, then resumed, "seven...  eight.... nine!"

"Fuck!" Wells muttered when he came up again. His eyes were watering but he was real fucking into this. In every way Carson was testing his limits this time and doing really well at it. "God, I love your dick, Boss," he added, his voice thick with his own mucus. 

"Gonna go for ten, Wells?" I asked. 

"Yeah, I wanna," he said. "Been thinking about this."

Damn. "All right," I urged. "Swallow me."

He did, again perfecting the fast but not too fast swallow. For the first four, he held perfectly still. "Five..." Carson's eyes watered now and I could see him fight himself. "six.. seven..." The guy started gagging, but as I counted he swallowed it down. "eight... nine..." Then came a deeper grunt from him as he fought to hold it. "Ten!"

When Wells pulled off that string of slime was real thick, milky in color and frothy as it plopped off my cock. Some landed on my suit trousers and some splattered on the towel below, but a good half landed on Carson's dress shirt.

"Damn, Boss," he gasped, overwhelmed by all of the sensations and emotions of this act. It was a lot for Carson to deal with. 

I paused and felt my prick jerk in excitement. This was crazy hot. I no longer counted in my head but just gave Carson a beat to recover before saying. "Let's do this buddy," I urged. 

He nodded gamely but I could sense his apprehension. "OK," he muttered then went down on me. I could see from his eyes that he realized he was descending too slow and a fear swept over him that he'd messed up this round. 

I ran my fingers through his silky blond-ish hair. "You're good Wells," I assured him. "Come on, you've been a real trooper so far.... just one more round..." Then softly, but with a regular count I spoke. "two... three...." A slight gag came but nothing big. ".... four... five..." My own voice was getting excited now, seeing Wells push his limits. Count five after going multiple rounds was a LOT harder than round five the first time. And even as he grunted and wiggled his body some to fight his own body, Wells kept at it. "...six... seven...." Wells gagged and pulled off. I thought that was it for round eleven, but after with drawing an inch, he gulped down and was back at it, pushing into the hilt once more. "We good?" I asked, then taking Carson's stillness as a response, I continued. "... nine.... ten...." I could see his eyes really tearing. This was tough on Wells. But he was almost there. "ELEVEN!"

Wells wasn't slow in getting off this time. He practically spit out my dick and with it a heavy rope of his own slime, which mostly clung to his beard. His eyes were tearing up as he looked up at me. "Damn, Boss!"

"Fuck, man," I hissed, running my fingers along Carson's hair. I hoped this wasn't too gay, touching him like this, but I wanted to let him know how appreciative I was of what he'd just done. I tried reading his mood. "You up for another Wells?" I asked.

"Tapping out, Boss," he replied. 

I nodded. "You did great, Carson," I said. "Incredible." 

"Give me a second, and I can take care of you," he offered. "Like you like."

"You mean...?" I had an idea of what he was getting out. 

The guy had a big grin. "Merry fucking Christmas, boss," he chuckled. "I know you like it a little messy...."

"You're already a mess, Wells," I said looking down on the vision of his knelt body. He didn't seem to have any spit or slime on his suit but his shirt was soaked with it and some still clung to his beard.

Carson smirked. Maybe if he hadn't been a little tipsy himself he would have felt more self-conscious. "Just ease up if I give the signal, OK?"

"Oh yeah," I agreed. "Tap my leg anytime and I'll ease up."

I gave him another second to recover, but I was real turned on. I guided my dick back to his wet lips and pressed in. I held on to the back of his head and gave slow, gentle thrusts into his skull. 

"Fuck yes," I hissed. I had a pretty good read of Wells' response and what he could take but I was starting off cautious. 

Then Carson deep throated me and I held his head against my crotch. I felt his body hunch a little and heard a soft gag. "Gonna make some slime for me, buddy?" I heard another soft gag, then I pulled back to see my handiwork. There it was, all of that beautiful mucus, frothed up and clinging to my cock. 

Carson was teary eyed but actually turned on too. "Damn, Boss," he muttered as I pulled back to show it off to him. 

"So good, Wells." My dick was wet and the viscous throat spit clung to me rather than drip off. "Spit some more on me, buddy."

He got a lewd grin and gathered the spare spit in his mouth to slobber it on my dick. It wasn't as thick, but was a combo of regular saliva with the leftover slime. 

"Fuck yes," I muttered. Then, "I gotta get off, buddy. Bad."

He nodded his agreement and I gripped his head again to steady it for a final face fuck. I didn't go hard charging with the deep throat. Instead I got off on working that slime, which got looser the more it combined with Carson's new saliva. It began making squishy sounds and was now running freely from his chin and all over my crotch. I'd regret putting my suit through this abuse, but I was turned on this all. The nastiness of it, and the physical sensations. The slickness made Carson's mouth turn into a real fleshjack feel on my prick. I started cumming. 

"Shit!" I gasped as the pusles of cum shot out into Carson's sucking mouth. The whole scene had worked me up big time and I had about eight solid jets to that ejaculation. I was feeling sensitive at last.

I pulled back, hyperventilating as Carson unzipped for his own release. It took like three tugs and he was cumming too. He finally pulled up a towel to wipe off. 

"I'm afraid I didn't get you a Christmas present, Wells," I quipped. 

He smiled, those green eyes meeting mine. "It's OK, Boss. I think I got my present right there."

I swear my cock jerked when he said that. But I had a pressing matter on my hand. "OK if I go clean off?"

He nodded, and I went to the bathroom to wipe off the mess from our my crotch. Lessoned learned. 

When I got back, Carson was gathering up the towels and getting back to normal. 

"I wasn't sure you'd go for that, Carson," I said. "But that was incredible."

He gave me a knowing grin. "I guess I got freaked out last time," he explained. "But I want this too. You know, the training," he added with a blush.

I thought for a second. "How about this, Wells? You find a video you like, that turns you on. Send it to me."

He smiled. "I can do that, Boss." Then he seemed more pensive. "You think anyone at work suspects anything?"

I didn't have to think about it, because I was always keenly aware of that possibility and nervous about it. "I'm pretty sure they don't," I said. Then, I added, "I think we're playing it right. But if you wanna cool it..." I offered.

"We'll see," Carson said. "But I'm good for now. Like I say, I wanna go further... explore this."

It was a little awkward after that. With a gay fuck buddy, there would be a goodnight kiss, or at least a hug or something. And with Carson before I'd slip back into buddy mode. I didn't always know how to adapt to ex-frat-boy ways, but in finance I knew how to well enough. 

Only after I abused Carson's throat and tested his limits, that felt weird now, too, giving him a fist bump and telling him I'd see him around. 

Still, I felt alive and excited as I got out in the cold night air and made my way home. I hadn't told Carson this, but hands down this had been the most exciting sex I'd ever had.