#this is rough

Not to the point of total ruin or prolapsing, but so it's loose enough for you to just sliiide right in without a snag until you're balls deep and he swears he can feel it in his throat; loose enough for you to fuck into him in long smooth strokes that has him shaking and whimpering into the sheets; so loose yet it still tries to suck you in deeper, uselessly trying to clench to keep you inside every time you pull back to thrust into him again.

I like the type of gape that his hole stays open when you pull out, the type of gape that no matter how much the poor man whines and tries to clench he can't keep your cum from slowly trickling out down his taint and balls. But the silly thing doesn't need to worry his pretty little head, it's not his fault his hole is so sloppy and loose. You're there to trail your fingers along the small rivulet of cum, gathering it on the pads of your fingers so you can stuff it back into his hole. And he's so content now that he's not empty, his puffy rim fluttering around your knuckles as you spread his already stretched hole with your fingers until you can see your cum pooled in his soft body.

I also love getting to that point.

I'd love to lay him down on the bed and oil him up, make sure he's so relaxed and pliant he's almost asleep by the time you even near his intimate parts. All he could do is turn his head to catch your gaze, skin flushing with goosebumps as you fondle and massage his ass, your thumbs circling his virgin tight hole before going down, caressing his balls and lazily stroking his cock just as it's starting to twitch with interest. And I'd keep my hands moving slowly, up and down, up and down, until he's sighing and panting against the pillow, thighs trembling with how he tries to keep them open for you, cock hard and his rim twitching whenever you press your thumb against it without trying to penetrate.

Only then would I lean in to lick around his hole, your teeth gently nibbling and sucking on his rim. A full body shiver trails up his spine and the prettiest sounds leave his breathless lips when you breach him with your tongue. And he's so tight it takes you ages of slowly eating him out to stretch him out enough for him to be able to take one of your fingers. It's heaven for you but hell for him, the movement of your tongue against his fluttering slow and lazy sensation keeping him teetering on the edge of that pleasure without it being enough.

And stretching him open slowly is the fun part, taking all the time in the world to get him used to the sensation of your finger wiggling inside him, stretching him open bit by bit so your tongue can lap at his sensitive walls as he moans and groans into the pillow, desperately trying to rut his ass into your face and his cock into the sheets. But he can cum as much as he wants, doesn't mean I'll stop until I can fit three fingers inside and his hole is begging for a fourth.

And damn the sight of his hole when you finally pull your fingers out is priceless; the small gape of his hole, the way his puffy rim continues to flutter and try to clench around nothing is as adorable as the small wiggle of his hips that he does and the soft spoken pleas to just "put it in" that has you finally giving him some relief.