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“Fuck…” I squeeze my eyes shut and try to unclench. Whatever I do is enough that his finger slides in. I shout like he just shoved a torch up my ass. “God,” I yell, the guttural boom so deep, I’m surprised the windows don’t rattle.
I hear him chuckle and then moan a soft, low, “Mmm…” His finger moves back and forth, in and out, and I attempt to adjust to the invasive feeling. I don’t take any pleasure from it—it feels like a cavity search—but I like that he likes it. His obvious excitement, which is telegraphed by all the satisfied sounds he’s making, keeps me very, very hard.
“Good?” he asks.
“Sure,” I lie. What am I supposed to say? No? That it feels like a dirty version of a prostate exam?
“It’s crazy,” he says, words soft and entranced. “It’s like you’re sucking me inside. Swallowing me up. I’ve never felt anything like it.” With that, he adds a second finger, and I react violently.
My ass clenches tight, and I shout again. “Fuck!” I’m stuffed and stretched and so uncomfortable with how it makes me feel, I’m sweating from the suppressed urge to get away.
He fucks me slowly with those two fingers three or four times before asking, “Do you want me to stop?”
“No,” I grunt. I can take it. Might as well. I’m here, aren’t I? I put myself here.
“So tight… Drew…fuck.” He’s breathing heavy and stretching me with spreading fingers. My asshole feels like a ring of fire. “I wish you could see this. It’s so hot. So fucking hot…”
I don’t want to see it. It’s hard enough to bear it—the suffocating sense of how far I’ve fallen that I would let this man debase me like this. Defile me. And yet, my dick doesn’t seem to mind. It’s so hard it’s stretched to its own limits, thick and pulsing on my abs, precum wetting me while I pant with the effort it takes to accommodate this finger fucking, wondering why people enjoy this—wondering if there’s something I’m missing or not allowing myself to feel.
When he slides those two slick fingers down the seam of my taint and cups my balls a moment before pushing back in, though, my cock throbs hard. Something different happens. Something I don’t hate quite so much, and a groan issues from my mouth, because while the burn is still there, it now feels like it’s supposed to be. When he stuffs me full, I don’t feel quite as empty.
I’m not going to say it feels good, but it stops feeling bad.
I guess I’d say it feels exactly how I thought it would when I strip all my preconceived notions surrounding what it means away.
Which I take to mean I’m ready for the rest.
“Fuck me,” I tell him. “Just do it.”
Silently, with only our heavy breaths filling the air, he slides his fingers out and replaces them with the smooth, slick head of his cock. The silk of it against my burning hole reminds me it’s about twice as thick as what was just inside me, and I could barely take that without wanting to wrestle him off me.
I seriously don’t know how I’m going to do this.
He meets resistance on his first press forward. I’m clenched tight again, not on purpose, but because my ass is clearly terrified. But as he continues to nudge, I spill more precum. He’s not being too forceful. He’s waiting for me. He’s got his hand on my hips, and his tip is knocking gently on the door, asking me to open up and let him in.
I hold my breath, straining. With his next nudge, and with the help of an ungodly amount of lube, his cock breaches my stinging outer ring. I grunt loudly—very loudly. It’s brutally uncomfortable, but the sound he makes is a shuddering gasp. A breath that catches a dozen times on its way in. “Oh Jesus,” he moans. “Fuck it’s so tight… Oh my fucking God. I’m not gonna last Drew,” he says to me as if in apology.
I bite the meat of my hand between my thumb and wrist to try and stifle the scream my throat strangles on the way out. A sound I’ve never heard comes out of me instead. Like a wounded animal. Like someone begging for their life.
“Fuck,” he hisses, and he slides in deeper. “Oh shit, I’m sorry—you’re fucking swallowing me.” He makes an attempt to pull back, but he comes right back in, deeper. So deep, I swear if I touched my belly, I’d feel the tip of him there. “Shit. Drew. Fuck. I’ve never been this deep.”
His thrusts feel purposeless. Out of his control. Instinctual. “This is so fucking good.” One of his hands smooths down my spine, sending electric pulses across the surface of my skin, over-sensitized and sweating. His words have a persuasive effect, at least on my cock.
It’s convinced it likes this. I’m hard as a rock and ready to blow even though the rest of my body and my mind continue to focus on all the bad—the overwhelming pressure. The utter intrusion, the sense of wrongness.
But then he’s letting out soft whimpers. Like it feels so good to him, he’s on the verge of weeping. And when he digs his nails into my shoulder blades and his thrusts tighten up, all my resistance shatters.
“Fuck,” I grunt, finally lifting my head from the safety of my hands so I can turn to the side and breathe. I reach down to fist my cock, and that’s when everything changes.
It’s like all at once my mind and body align, and as I pump my dick to the thudding rhythm he’s found in my ass, sensation floods me, and very little of it is bad. And what bad there is of it is bad in the best way. Filthy. “Goddamnit,” I groan. “Just like that.”
“Mmph.” He sounds like he’s on the edge of insanity—moan pitched high and helpless.
I wouldn’t go so far as to say I read the pain as pleasure. It’s still uncomfortable. It’s still the same violating sense of having a foreign object shoved deeper and deeper into my body, but the pain and the intrusion themselves become—pleasurable isn’t the right word—arousing is too mild, too. What I’m feeling as we both get closer to climax might be something there’s not a word for. Except that it’s dirty and obscene as fuck, and it’s going to make me come ridiculously hard.
“Fuck, I’m too close… your ass is breaking my dick. I’m about to come. Oh, God, I’m gonna fucking come…” His words are barely out before heat burns deep in my gut, and between his pulsing cock, the warmth of his balls on mine, and the groans he’s unleashing, I’m covering my own cock so I don’t destroy his comforter with the amount of jizz I spray, my own jagged groan long and low as tears spring to my eyes with how close to death I feel—like my life has been brought to the very edge of existence and then spared, but not before this wave of gut-wrenching ecstasy courses through me. And then another, and another as we both continue to spill our releases and try our best to survive them.
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