Could 75 be possible with Shawlong? "cockwarming" reader's *huge* strap on (or oversized cock?) and teasing him because it's too much.
75. “Please, I can’t sit still.”
For the first few seconds, Shawlong is half-certain something is going to tear. Even though you spent an agonizingly long time stretching him open on your fingers, coaxing his body to relax, even the tapered tip of the plastic thing you’re intent on shoving inside of him feels impossibly wide.
He’s straddling your lap, kneeling, with only the tentative support of his unsteady legs keeping him from dropping down on the fake cock lined up to his hole. The position feels ridiculous— he’s too tall for this, all sharp angles and not knowing where to put his hands—, but you’re still happily kissing the edge of his jaw, in between assurance that he’s doing so well.
“...it’s too big,” Shawlong hisses, when the next half-inch sliding in sends a sharp, threatening spasm through his guts.
“You can take it,” is your confident reply. “Just relax, you’re tensing up too much.” How could he not? It feels like he’s going to be split apart.
Your steadying hand on his thigh dips lower, though, and any argument Shawlong could have formed melts away with the sudden shock of your fingertips against the little nub just above where the toy is pushing in.
Just that brush of contact has his limbs twitching and his nails digging into your cloth-covered back. Slick with lubricant and his body’s natural, pathetic attempt at easing penetration, the blunt pads of your fingers slide uselessly over the nub— and yet, the near-frictionless slide still feels like it’s scraping against bare nerves. Painful isn’t quite the right description, and the deep, spasming clench that follows is even more ambiguously awful.
Or at least, that’s what Shawlong thinks right up until, without any warning, his body surrenders to another inch or two of unyielding plastic.
Suddenly, the uncomfortable stretch turns mind-numbingly good.
The next few minutes are a blur of more touching and continued, coaxing encouragement to relax, open up, and take it. It’s not until his full weight is resting in your lap that Shawlong realizes that it worked.
Somehow, it’s inside. And rather than the agony he’d feared, he just feels... full. Stuffed to the farthest limit of what this body can accept.
“There, see? I knew you could do it,” you tell him. The half-teasing, half-praise tone borders on unbearable when he’s already so frazzled. There’s no way for him to respond with any semblance of dignity. “The hard part is over. All you need to do now is stay right here, and stay still.”
As much as Shawlong favors the idea of staying still, at least until he’s had a chance to adjust to the barrage of new, overwhelming sensations, his body has other ideas. Especially, once the light, teasing touches return to his clit, a confusing urge to squirm into the pressure takes over every time his concentration slips. It’s hard to remember why he shouldn’t do that— and every little clench around the toy makes the impulse stronger.
“...I c-can’t sit still,” he tells you, after a few failed moments of fighting to control himself prove it a futile, miserable effort.