Q:

When pleasuring another dude’s cock, when should I stop riding/sucking/stroking after he’s cum? I know how sensitive my cock gets after cumming, but I also feel like some of the sweetest and most intimate moments can be what I do with his cock as it subsides and softens, not to mention that there can still be intense, intense pleasure in those early post-cum moments.
Go for it, while adapting to his needs!

[I] agree with you that the sweetest and most intense pleasurable sensations can be had soon after ejaculation. I personally call this post-ejaculatory penile massage post-orgasmic goading (but that’s a personal terminology as I’ve never seen an official terminology for this) because this deliberate teasing is done at a time where we all know the penis to be extremely sensitive.

Post-orgasmic goading is not something we men tend to do instinctively for ourselves, as a consequence of the additive impact of three phenomena happening quickly after ejaculation:

1. The powerful and overwhelming sensation of fatigue that numbs us after ejaculation
2. The almost instantaneous disappearance of all interest for sex that follows ejaculation
3. The excruciating sensitiveness of the penis — of the glans in particular — following ejaculation

Acting synergistically, these phenomena trained us very early into avoiding any stimulation to our penis after ejaculation. In fact, this is something most of us were driven to understand only a few weeks after our first ejaculation. As a result, most men will have little to no experience with (and, for some, even the knowledge of) the powerful sensations that can be squeezed out from the penis after ejaculation.

Does that mean that post-orgasmic goading should be avoided? Not at all: on the contrary, it should be encouraged.

What it means however, is that you have to be mindful when initially introducing a partner to post-orgasmic masturbation.

• Begin by announcing your intent. I don’t mean writing down a contract in triplicates, but after the guy has cum and you continue to masturbate him, tell him that you do. Something like “seeing you cum was wonderful, I want to see you squirm and hear you moan longer”. Eventually, you won’t need to ask his permission to go on with the post-orgasmic goading, but at first you’ll need to, so that your partner doesn’t feel apprehensive. Indeed, when unexpected, post-orgasmic goading will bring forth a feeling of loss of control (and it is, to a point). And most men don’t live well with that feeling, as it is not part of the male psyche.
• Be clear that you’ll stop if he asks to, and indeed stop when he does asks you to… but with a slight delay. The delay is important as the intensity of the caresses are very likely to make him utter you to stop way too soon. So you should playfully continue a bit longer, yet without going overboard so that he’ll know that you can be trusted. At first, you might not continue for long after ejaculation, but as he learns both that you can be trusted and to let go, you’ll be able to give him long minutes of quasi-orgasmic pleasures…
• Finally, be considerate. While you can continue to caress the shaft with a relatively strong grip (yet toned down compared to how you held his cock as you sent him through orgasm), you must handle the glans with extreme care. Using his semen(1) as lube, rub the glans slightly and delicately with your fingertips. You’re better off beginning too delicately than the other way around because if you begin the cockhead’s caresses too harshly, it will hurt and that will be the end of it. To evaluate your accomplishment, watch his abs for sudden contractions, watch his shoulders dance around, watch his head moving back and forth, watch also for his hand(s) that may attempt to grip you (surprisingly) strongly in an attempt to immobilize you. Listen to his moans also. Embolden him to move and moan…
• When introducing a man to post-orgasmic goading, one has to be initially very mindful and open to the needs of the other. When done correctly, it opens a new world of sensations and it is totally fun and addictive(2) ! After some time, you’ll be able to make him dance, squirm and whimper for a surprisingly long time. He will even be looking for it.

While semen is a hassle to deal with after ejaculation, we all like to be reminded that we ejaculated and how much we came. Playing with our semen and smearing it all over helps drive the point that we came and helps us registering that we impregnated the world with our DNA. It makes us feel manly. It’s important to fool around with cum, and doing so won’t change the fact that a clean up is needed after orgasm.

This article is written with a partner in mind as this is the question, but the same applies to you too. Every man should use post-orgasmic goading on their own cock. The same careful and delicate approach applies, especially since it is so difficult to persevere at first, as the glans’ exquisite sensitivity tends to make us spineless. Yet, going against the post orgasmic fatigue and the transient disinterest in sex, on one side, and learning to exploit instead of steering clear from the penis’ post orgasmic sensitiveness, on the other side, allows us to milk even more pleasure from our penis. Something no one can be averse to, right? As it goes so much against our instinctual behavior however, it has to be learned and practiced. Practice makes perfect, though. So practice my lad, practice !