I had a thought about the knight making the squire jerk off in front of them, though I'm a little conflicted on which flavour of this I prefer.
Of course, you could go with the caring knight, the sweet knight, murmuring encouragements the entire time. Praising the squire for obeying so well, for tending to themselves with the same diligence they apply to caring for their knight. And of course the squire is eating it up, hazy with it, awash in the pleasure of their knight's approval, almost more than the pleasure of their hand. Moving exactly as their knight tells them, so eager to please, to do a good job, to where the embarrassment is forgotten. The squire is meant to obey the knight, and as long as they follow orders, they will be rewarded. The knight coaxes the squire right to the edge, encouraging the squire to watch their knight as they finish, to breathe their knight's name in that final moan.
However, I think I am partial to the harsh knight, the one who teaches with pain and punishment. The knight who lets their squire get stuck in tight situations and doesn't raise a finger to help, because the squire is perfectly capable of getting themselves out of it, if they use their brain for a change. This is the knight who laughs when their squire gets pinned in a sparring match, who taunts the poor thing until the squire's indignation is strong enough to propel them out of the hold.
This knight is mean when the squire drops to their knees as ordered, when they unlace themselves as ordered, when their hand slips between their legs as ordered. The knight mocks what they see there, laughs at the red flush to the squire's cheeks and the way they glare at anything else in the room, anything to avoid making eye contact with their knight. The squire wishing they had it in them to disobey, but as much as they want to push up against the confines of their knight's control over them, they want to prove themselves even more. So they touch, rub, stroke, shudder at the sensation of the knight's hungry eyes roaming over them.
The squire would normally do this differently, laid back on their bedroll, properly bare, safe from prying eyes; instead, the cold floor bites into their knees, and their hose and braies are bunched hastily around their legs, just far enough out of the way to get a hand on themselves, and it's somehow more indecent for being mostly clothed. The knight orders them to touch too slowly, far different from how the squire usually tends to themselves, hurried and goal-oriented, intent on quick relief. Sometimes the knight makes the squire take their hand off altogether, makes them whine as the throbs of pleasure ache unfulfilled, makes them hold out their hand for the knight to see the shine of their arousal on their skin.
For as soft and slow as the knight is making them touch, there is nothing soft about the knight's words. Harsh laughter and biting degradation drip like honey from the knight's sharp grin. "Is that really the best you can do? Pathetic little thing, so desperate that you'll drop your braies and fuck your hand right in front of me. What exactly are you hoping for here, squire? What do you think will happen when you come? Oh yes, you will be coming, though not any time soon. Are you hoping that I'll praise you for it? Tell you how well you did, following my orders? That's all you want, isn't it? To be told that you're good, that you're useful, that I like what I see." The knight leans closer, and the squire manages to meet their gaze, glaring up into it, defiant even as they obey. "Tell me, runt. Tell me what you want from me."
And the squire does, reluctant and quiet at first, hating every word out of their mouth, hating how easily the knight can reduce them to this, loving it almost as much as they hate it. The knight would laugh as the squire reveals their desires, their hand moving faster of its own accord, their thighs shaking to hold them as the pleasure courses into every corner of their body. But of course, the knight doesn't do any of the things the squire confesses to wanting, doesn't touch them, just eggs them on, ordering them to stop every time they see the squire getting too close, making them squirm and whine for a moment before telling them to continue, keeping their arousal blazing but never able to burst. Telling the squire that they're only allowed to come if they beg for it, and the squire would have once thought that they were too proud to ever do such a thing, certainly not to their cruel, arrogant knight.
The squire holding out as long as they can, cursing and mouthing off while the knight keeps quiet note of how many punishments the squire is racking up, greatly looking forward to doling out those punishments at a later date. "You can beg until I decide to be merciful," the knight purrs, "and you can come all over yourself while you thank me for every drop, or you can put your clothes back on and go to bed wanting. It's your choice." And of course, it's no choice at all.
The squire can hardly keep from welling up with enraged tears as they finally beg their knight, too close to stand it, too aroused to possibly leave this unfinished. And oh, the knight makes them beg for all they're worth, makes them get specific with their begging, and waits until the first tears roll down the squire's burning cheeks before snarling at them to get on with it, then.
The squire breaking halfway through the first "thank you", the words falling into long, loud moans, wordless cries of pleasure pouring from them before collecting back into babbled sobs of thank you, oh god, thank you, for once blissfully unashamed of their dependency on their knight, their cruel, heartless, merciless knight, who currently is drinking in the squire's mindless obedience with a thirst that is far from sated, that will require several more sessions like this to even come close to being enough.
Knight who might be a little addicted to this, to teasing their squire until the walls come down and the squire is laid bare. Knight who will be stuffing the implications of this as far down as they can, taking it out on the squire in sneers and cutting words that only barely veil their growing obsession with making the squire debase themselves for the knight, preferably on their knees.
