Chapter 31 Ivan #4
He tries again, not going as deep this time, using his hand on what he can't fit in his mouth—the base of my shaft, stroking in rhythm with his sucks, twisting slickly.
It's messy and imperfect, saliva dripping down to my balls, his lips red and swollen around me, and the best thing I've ever felt in my life, heat coiling tight in my gut.
"Your mouth," I gasp, my hips wanting to move but I'm holding them still, not wanting to choke him. "Jay, your mouth is—I can't— so hot and tight, sucking my cock like you were made for it."
He hums around me, the vibration shooting straight through my length, and I almost lose it right there, pre-cum flooding his tongue.
But then he pulls back slightly, his hand still stroking, and his other hand trails lower, cupping my balls again before dipping further—fingers brushing over my taint, then circling my hole tentatively.
"Can I touch you here too? Finger your ass while I suck you?
I want to make it intense for you—your first time getting rimmed like this, but with my finger, exploring inside. "
My breath catches, a mix of nerves and excitement surging through me. "Yeah—fuck, yes. I've never... no one's ever touched me there. Be gentle, but... do it. Finger me."
He grins, eyes dark with promise, and sucks the tip of my cock back into his mouth while his finger—slicked with saliva from his own mouth—presses against my entrance, circling the tight ring of muscle slowly, teasing.
The sensation is foreign, electric, making my hole clench instinctively, but he doesn't push, just rubs gently, massaging until I relax.
"Relax for me," he murmurs around my cock, the words muffled but clear. "Gonna slide in slow—feel how tight you are? Gonna open you up."
He pushes the tip of his finger in, just breaching me, and I gasp at the stretch—burning at first, but then blooming into something deeper, fuller, as he sinks to the first knuckle, crooking it slightly to search.
His mouth works my cock harder now, bobbing faster, tongue lashing the head, while his finger thrusts shallowly, exploring the velvet heat inside me.
"Fuck—Jay, that's—your finger in my ass, so deep—" I moan, hips rocking between his mouth and hand, the dual sensations overwhelming.
He finds it then—my prostate, that sensitive bundle—and presses firmly, rubbing in circles, and pleasure explodes through me, white-hot, making my cock leak copiously into his sucking mouth. "There—right there—fuck."
He hums again, finger fucking me deeper now, adding a second one after slicking it more, the stretch fuller, tighter, scissoring gently to open me while his mouth takes me as deep as he can, throat working around my girth.
The rim of my hole clenches around his fingers, the intrusion turning to pure bliss as he strokes inside, milking my prostate with precise presses.
"I'm not going to last," I warn him, the pressure already building at the base of my spine, balls tightening under his touch. "If you keep doing that—if you don't stop—fingering my ass like that, sucking my thick cock—I'm going to—"
He doesn't stop. He sucks harder, strokes faster with his hand at my base, fingers curling insistently against my prostate, rubbing relentlessly, and I can feel the orgasm building, tightening, ready to break—intensified by the ass play, like nothing I've ever felt.
"Jay—I'm going to come—you should—"
He doesn't pull off, just moans around me, fingers thrusting deep one last time, pressing hard on that spot, and I shatter with a roar, my cock swelling in his mouth before pulsing thick ropes of cum down his throat—hot spurts that he swallows greedily, milking every jet with his tongue and lips, his fingers still rubbing inside me to prolong the waves, aftershocks ripping through my clenching hole.
When I finally come back to myself, when my vision clears and my heart stops trying to beat out of my chest, spent cock softening in his mouth as he pulls off with a wet pop, fingers slipping free gently, he's looking at me with a smug, satisfied expression, lips shiny with my release.
"How was that?" he asks, and he knows the answer, licking his lips to chase the taste—salty, musky, mine.
"I think I died. I think I'm dead and this is heaven. That... your mouth on my cock, fingers in my ass—first time anyone's done that. Felt like you were touching my soul."
"You didn't die. You just came really hard—filled my mouth with that hot cum, tasted so fucking good.
" He grabs the corner of the sheet and wipes my stomach clean where a bit overflowed, gentle and careful, then cleans his fingers casually.
Then he crawls up my body and settles his weight on me, his head on my chest. "I liked that.
Making you lose control. Watching you fall apart—feeling your ass clench around my fingers while you came. "
"I liked it too." I wrap my arms around him, holding him close, my heart still racing, body humming with satisfaction. "I liked everything about it. Especially that... the fingering. Fuck, we need to do more of that. Just wait, you're gonna love it too."
We lie there for a few minutes, catching our breath, just holding each other. I feel completely content. Happy in a way I'm not sure I've ever been, in a way I didn't know was possible.
Jay props himself up on his elbow, looking down at me with a curious expression, something almost shy.
"Mind if I ask you a question?" he says.
"You just had my cock in your mouth. I think we're way past the point of asking permission for questions."
He laughs. "Fair point. Very fair point." He traces a finger along my collarbone, watching the path it makes. "What do you actually know about guys fucking each other? Like, the mechanics of it?"
I snort at his bluntness. "Smooth transition. Real smooth."
"I'm serious. What do you know? Because I want to know what we're working with here and how much research we should do."
"Uh." I think about it, trying to remember anything I might have heard or read. "Not much, honestly. I know there's penetration involved. Obviously. And lube. Probably a lot of lube. And I think there's some kind of preparation that has to happen first?"
"That's it? That's all you know?"
"That's it. I never exactly had time to research gay sex. I was too busy working twelve-hour days." I look at him. "What about you? What do you know?"
"About the same. Maybe less." He's quiet for a moment. "I know there's prep involved. Like, you can't just—" He makes a vague gesture. "You have to get ready first. Stretch things out. Use fingers, I think. Work up to it."
"That sounds uncomfortable. Or painful."
"I think it can be. If you don't do it right. If you rush it. I want to do it right when we get there. I don't want either of us to have a bad experience that ruins it."
"Me too. I never want to hurt you. You said I have a big cock. Is that going to be a problem?"
Jay snorts. "No, I love your cock. You can stretch me out good first, okay? You'll never hear me complaining about the size of your cock."
"Okay, but I'm not in a hurry to fuck you that way. I mean, I'm dying to, but I can wait."
"Have you ever been with anyone else?" Jay asks. "Like, at all? Kissing, touching, anything?" He seems nervous asking, like he's afraid of the answer.
"No one. Ever." I meet his eyes, hold his gaze. "You're my first everything. First kiss, first time touching someone like this, first time being touched. First orgasm that wasn't my own hand. There's never been anyone else. Not even close."
"Same here." He nods slowly, and I can see relief in his eyes. "So, we don't need to worry about getting tested or anything. Right? I mean, if we're both virgins, if neither of us has been with anyone—"
"I don't think so? There's nothing to test for if neither of us has done anything with anyone." I stroke his hair. "But we can if you want to. If it would make you feel safer."
"No, I just—I wanted to make sure we were on the same page." He reaches out and takes my hand, threads our fingers together. "And there's not going to be anyone else. For me, I mean. Just you. I want you to know that. I want you to know I'm all in."
"Same. Just you." I squeeze his fingers. "I'm not interested in anyone else. I never have been. It's only ever been you, even when I didn't understand what that meant."
He brings my hand to his lips, kisses my knuckles softly. "Then we're exclusive. Monogamous. Whatever you want to call it. We're together. Just us."
"Just us. I like the sound of that. I like it a lot."