24 Jack/Chase -"delicate": Worth the pain
He really can’t tell how he’s gotten there, everything’s been going fast. One moment they’ve been talking, just talking (sure, the tension has been there all evening) and the next moment he is being pressed up against the kitchen counter with Jack standing between his legs, his tongue chasing his own in a kiss that effectively shuts up the tiny voice of reason in the back of his head. He doesn’t care that he shouldn’t even be there in the first place, he doesn’t care that the erection pressing against his own is his boss’s and he really doesn’t car that when he’s woken up that morning to find his naked body entangled with the just as naked body of that very boss’s daughter. All he can think of is Jack kissing him like he’s never been kissed before, his hands roaming over his chest and sending shivers down his spine that alternate with waves of heat when Jack brings their hips in closer contact.

And the last remains of coherent thought are gone when Jack pulls out of the kiss and looks at him with an unbelievably sexy smirk, his eyes hazy with lust. He leans forward and slowly licks his way up his partner’s neck to his earlobe which he pulls between his teeth, biting down careful enough not be breaking the skin but thoroughly enough to make Chase dizzy.

“You now, I’d really like to fuck you” Jack’s breath is hot against his ear and his low voice sends a flash of heat to his groin. Yet he doesn’t know what to reply and feels the blood rush to his cheeks when he finds himself stammering, in a mixture of embarrassment and confusion and barely containable desire. “I haven’t…” He swallows not able to actually say the words, not now, and he feels himself break into a sweat.
Jack’s lips seek their way from his ear to his mouth and he nips at his lip to get him to meet his gaze.
“You haven’t been with a man before” Jack says, agonizingly slow trailing his hands down his chest and towards his navel, his nails raking his skin.
He licks his suddenly dry lips and there is an almost undetectable shake of his head. “No.” His eyes dart away from Jack’s. But Jack lifts up his hand and runs it over his cheek and gently turns his head back so that blue once more meets green. He looks at him steadily for a long moment, the only sound their racing hearts and the sharp little breaths that witness of the tension between them and tickle the other man’s skin. Jack’s expression has softened but the raw need is still there, clear, unmasked, unreined.
“Don’t worry. Let me take the lead. And I’m sure we’ll find something to do for those long delicate fingers of yours.” His hand slides around Chase’s hip, cupping one of his cheeks and pulling him closer, at the same time once more capturing his lips with his in a kiss almost bruising in its ferocity. When he pulls back their breathing is laboured.
“But I’m not going to lie to” Jack pulls him even closer, grinding his erection against him. “It’s going to hurt. So the question is: Does the thought turn you on of my dick up your ass, stretching you, moving inside of you?"
Chase closes his eyes for a moment and tries to control his breathing. He’s too far gone to worry about pain. Or consequences. All he sees is the picture of Jack sliding into him and he nods, vigorously. “It does.” His voice is hoarse.
"You sure?" Jack sinks his eyes into Chase’s.
He nods again.
“Good.” Jack presses his lips to his in a quick, hard kiss. “Come on." He pulls Chase towards him and starts unbuttoning his shirt while he maneuvers them to his bedroom. He stops in front of the bed and admiringly lets his eyes sweep over Chase’s now naked chest. Slowly trailing his fingers down his chest he lets them slide over the front of his trousers, too tight now, and cups him through the fabric, causing Chase to moan. He smirks and starts unbuttoning his trousers: “I promise I’ll make it worth the pain.”