Chapter 40 by Transactional
How does Josh begin his first blowjob?
He takes the shaft (cocksucker route)
As the moment of truth faces him, Josh feels time slow down. He feels his heart beating in his chest; the saliva accumulating in his mouth as he forgets to swallow; his bare cock bouncing in the air, still hard from an hour of jerking off; the pulse emanating from Tyler's shaft.
He thinks to the porn that he has just been watching. How do you even start a blowjob? Do you just stick it in?
He pulls Tyler's cock towards his face, then sticks out his saliva-covered tongue, moving his mouth in towards it. This is it, Josh thinks. I'm about to become a cocksucker.
Josh's tongue makes context with Tyler's frenulum, before he pulls it back into his mouth, running it up Josh's cockhead before he feels a hand on the back of his head, and all of a sudden his mouth is completely full of warm, precum-flavored flesh. Pushed off-balance, he releases his fist from Tyler's cock, and catches himself with his palm on his body, thumb and forefinger still wrapped around the shaft.
As Tyler releases the pressure on the back of his head, Josh pulls back until his lips cover only the tip, and it becomes clear that this was only a brief respite. Tyler forces Josh's head down, pushing him a little further down his cock.
"Oh, yeah, suck it Connie," he calls out, ostensibly to the screen. "Suck it hard."
Josh realizes that this instruction might be meant for him, and tightens his lips around the shaft now penetrating his mouth, and beginning to suck. There is a wet slurping sound as his lips tighten to seal around the shiny, saliva-covered cock, but this quickly passes, and soon Josh's tongue, lips, and cheeks are pulled in tight around it, wrapping it tightly in warm, well-lubricated flesh as Tyler again allows Josh to pull back, before forcing his mouth again down his shaft, this time gently thrusting into Josh as well.
This repeats over and over, with Josh unable to do much except to go along with it, eventually managing to keep himself balanced by anticipating the hand on his head and sliding up and down Tyler's erection without further motivation. As he does this, he feels Steve's body trying to squeeze in between Tyler's legs to do his part. He brings his knees together to give him space, raising himself slightly to take Tyler's cock from above, while Steve is spreading his legs to lower himself to the level of the ballsack hanging beneath Tyler's shaft.
"Yeah, suck those balls, you sexy oiled-up slut," he says, clearly not wanting to address Josh and Steve directly. "Work together."
Pressed arm to shoulder, Josh can feel as Steve moves back and forth, and from his viewpoint can see his mouth stretching Tyler's balls away from his body in time with the motion of his mouth down the thick black shaft.
"Don't use your hands," Tyler says. "Connie doesn't need to use more than her mouth to get this guy off. I know you've watched this so many times online, imagine all those videos and try to get into it, jerk yourselves off if it helps to imagine that you're not the ones sucking. "
Josh takes his hands off of Tyler's body, somehow relieved by the reduced physical contact, even as he slides his mouth up and down his cock. He imagines what it must be like getting a double blowjob, trying to imagine two beautiful girls giving him an the sensations that he and Steve are now giving Tyler.
Putting his left hand on his knee, Josh begins stroking his cock with his right hand, trying to focus on the sloppy blowjob in his mind's eye and not the one currently taking place in his mouth. He feels a moment of shame when he realises that he has somehow maintained his erection through this ordeal, forgetting that he was sitting back watching porn only a minute or two ago. But the feeling quickly fades as the minutes pass, his fist pumping up and down his cock, subconsciously synchronized with the motion of his lips up and down the cock in his mouth. The feeling of his fingers running across the bumps and crevices of his own member merges with the sensation of the veins and ridges on Tyler's shaft against Josh's lips, tongue, and cheeks, and he almost forgets what he is doing until Tyler snaps him back to reality.
"Oh fuck, I'm gonna blow soon," Tyler moans. "Time for you to do your job, Dan!"
Feedback greatly appreciated here. Please see chapter comments.
Does Dan take it for the team?
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The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 17, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
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