Training the Sales Guy

Heads up that this chapter goes even deeper into more hardcore oral sex. The next ones will get even more intense.

I considered my weird fuckbuddy affair with Carson Wells to be done. I kicked myself a little bit for pushing too far and freaking him out. Then I was glad it happened. It was an inappropriate thing from the start and had no good end. 

I hooked up with one guy a couple of times. I actually enjoyed fucking again. And kissing and making out. And the fun flirty vibe with another gay dude. As hot as Carson's blowjobs had been and as much as I'd enjoyed the naughty thrill of a finance bro who liked to suck dick, it wasn't a completely rewarding connection. 

Maybe I should have gotten out there to date again, but I still wasn't ready for that. I still saw Rob, my ex. We'd run into each other in the neighborhood and decided to have lunch, to try out the civilized adult thing. It was good and not good at the same time. We promised to do it again, but I worried that I needed more time. 

I was enjoying making a couple new friends. Some of my long-standing friends were more settled down now or had moved, while the mutual friends Rob and I had took his side mostly. But my social life was picking up and I was doing my best to squash my workaholic ways. I was never an athletic guy but joined one of the gay sports leagues in the city. It was a perfect mix of younger guys and older, single and coupled. I even got invited along on a beach trip in Mexico. 

It was a Saturday night I got back from that trip in fact when I got a text from Carson Wells. 

"Hey Bill sorry to bug you. Can we talk?"

"Yeah, when?" I typed back. 

"Now?"

It was like 10:30. I'd had a long day, and while my dick liked the idea of a booty call, this just felt like a strange way for Carson to start things back up. I knew the self-respecting thing would be to set boundaries and tell him I'd talk to him tomorrow.

"Sure," I wrote back, instead. "Come over?" I was already settled in for the evening and not in the mood to go out. If Carson was so urgent, he could come over.

"All right," he replied.

He looked distraught when he finally showed up. He had almost that tech-bro attire... black joggers, designer sneakers, gray hoodie with some logo on it. "Hey," he said softly as I let him in. 

I showed him into the living area and had him sit on the sofa. I sat down too, though not right next to him. "What's up, Carson?" I asked. 

He have me a wistful look. Gone was that perfect smile, but those green eyes were sexy as fuck. "Emily and I broke up tonight."

I felt bad, but also I was thinking, what the fuck? I didn't fucking know Emily. "Sorry, man," I said. But I couldn't be the guy to unload on. "But don't you have any buddies you can talk about this with?"

He nodded. "Yeah, I've been out with them." His voice got a little quieter. "But, fuck, Bill I need to suck a dick." He scooted closer to me and put his hand on my leg, running quickly up the bare leg and toward the him of my casual gym shorts.

"I don't know, Carson," I said, stopping his hand.

He looked hurt. "Oh. You seeing someone? I shoulda asked."

I shook my head. "Not seeing anyone. But well... you're pretty upset right now. I don't wanna..."

I was trying to respect him and not take advantage of his emotional state, but Carson laughed. There came thought pearly whites again. "What, Boss? You don't want your dick sucked?"

My dick was liking that idea all right. "When you put it that way," I replied, with a chuckle.

Carson placed his hand back on my leg, now teasingly running his fingers along my leg hair and my thigh muscle. I'd never seen this side of the guy. He still wasn't making the move to kiss or anything, but the sensuality of the touch was great. "I've been watching those videos you sent me... a lot actually."

"Yeah?" I asked. This was a surprise, all right. I spread my legs and let his hand travel up toward my crotch. 

He nodded. He had a strange emotional vibe. Definitely distraught and wound up. Maybe I was taking advantage of his state. "They're wild as fuck, Boss. But keep thinking what it would be like to try that."

"Which one?" I asked.

"Both," he admitted. "The training one... and that other one... I've watched some others like it, too."

I was completely hard now. I pulled Carson's hand away only now so I could pull down my shorts and briefs. I let my dong ride up fully rigid and throbbing. And here I thought I was too tired even for a stroke session before bed. 

The man grinned as he eyed up my phallus. "That's a great dick, Boss." He looked up at me, lust adding to the emotions on his phase. "Just go a little easier on me," he asked. "I've not done anything like that those videos."

I nodded and grinned, pushing up my erection for his gaze. "Will do, Wells... though don't sell yourself short. You've done a lot of training already."

I reached up and ran my fingers along the side of his hair, moving further back on his head. Carson got the hint and leaned forward. 

We'd never actually done it like this before, with me sitting down and Carson leaning over. But it was hot to see this hunk bend over to service me. I let him start, licking me and then sucking me in. Wells was great at this and his mood made him hungrier. He practically scarfed my hardon down to the root in three gos. 

"Fuck yes, buddy," I growled. "Eat my fucking boner." I didn't want to go too Dom on Wells. Partly because he was the kind of cocksucker who'd easily spook if you didn't respect him. And partly because trash talking wasn't the biggest turn on for me. That deep throat action was. 

I watched him work that deep spot in his throat with my cock, wildly bobbing on me and grunting deep sex grunts. He'd been thinking about this a lot, I know. Carson Wells was ready.

I held his neck tight and just started fucking his skull. Hard steady jabs. I'd only been with three guys who'd been up for this treatment before. 

It took maybe six thrusts before I hit pay dirt. Carson's gullet seized up and he gagged. I stopped my thrusts but I held him so he couldn't easily lift up. He was gonna retch but I talked him through it. "Swallow it back down, buddy... easy, man.... there ya go." I could see the tear stream from his eye and his face go red, but Carson did it. And the second he got himself under control I pulled him up.

"FUCK!" he cried, eyes watery. But damned if the guy didn't have a wild, excited look on his face. "That was intense," he hissed, his mouth thick with mucus. 

But not as thick as my cock was. Its length was covered with a good amount of Carson Wells' throat slime. 

"That's some perfect slime, buddy!" I hissed, encouraging him or at least thanking him. This is the kind of extreme oral that turned me on all right. "How you feeling?"

He looked up. "Not as bad as I thought," he answered. "I think I was more scared of it to happen than anything."

"You up for another go?" I asked. Hopeful as hell, but I'd respect his boundaries. 

He nodded. "I think so, yeah... So, Boss... how do you keep from, you know....?"

I knew the answer, but only as an oral top, not a cocksucker. Carson would have to find his own answer. But I did my best to explain. "You gotta know your body and learn how to control it. Lean into just the right amount of gag, then turn it off."

He took it all in. "What if I don't turn it off in time?" I could see the concern and knew where he was coming from.

I shrugged. "If it happens, it happens. But don't fear that. Tell yourself it's gonna be fine."

"All right," he said. Jesus, he clearly had been thinking about this a lot.

I applied some pressure on his neck again and I watched as Carson took me into his mouth again. I did the driving this time, using the residual thick saliva to ease my way into a slow steady deep throat fuck. After the previous activity, Carson was able to take me like a pro. One deep push after another. Six months ago this would have been enough to get me off big. It would be enough now, too, but I wanted more. I started a series of hard thrusts again. 

Carson, to his credit, did better this time around. But pretty soon the gag kicked in, and the guy knew what to do. He let it happen, only to swallow it back down. 

"Fuck yes," I hissed. I didn't have to go hard and deep now. I just let Carson do the sucking. Up and down on my bone, as that thick slime spilled out of his mouth and onto my balls. He was excited, maybe because of how thrilled I was. But this was hands down one the hottest things I'd seen. My hot business-bro coworker giving me some insanely sloppy head. 

"Fuck, Cars... I'm gonna cum!" I growled. I could hear the slickness of the sticky spittle on his chin and lips and he worked me with steady mouth strokes. "FUUCK!" I grunted as I gave up a super heavy load. 

Carson now moaned excitedly. He always liked when I came, but he seemed even needier now. 

He finally pulled back when my dick had enough. Even after a few months' break, the guy seemed to remember just how much stimulation I could take after a good nut. 

"Goddamn," he growled as he pulled off. He looked up at me, his mind in some new state of head fuck but definitely turned on. "Damn, you're one kinky fucker," he gasped. The slime and spit was on his chin and all over his beard. It was crazy hot. My dick wasn't gonna go down soon.

I lifted my hand up and wiped some of the wetness of his beard. "You may be a little kinky, too, Wells," I said. Then I nodded down at his crotch. "Need to get off?"

He sat up, showing that indeed he had an erection in his joggers. He slipped them over his boner and reached down. "I went soft but my hardon came back," he explained. I watched him started a stroke, then I stood up, letting my wet dong sway some in front of him.

"Too messy for ya?" I asked.

He shook his head no, and had that unmistakable look of need on his face. I stepped up and put my dick near his mouth. Carson leaned forward and started sucking me in again. A few strokes and the guy was cumming, hard.

I went to fetch some washcloths. We'd both need it. 

I expected Carson to have some doubts now, but he seemed quiet in a relaxed way. "Thanks for helping me out, Bill. I needed that."

I found my shorts and slipped them back on. "I won't lie, Carson," I said. "I haven't had a scene that hot in, like, forever."

He gave me a sly grin. "I'm glad, Boss. It was kinda crazy hot for me, too." He looked at his phone, where I gathered he had some messages. "Look, I'm gonna go meet some buddies now. Talk to you later?"

"Anytime, Wells," I said. 

And I meant it.