Page 105 of The Tryout

I pull my finger out again, not aiming for depth, but instead focusing on soothing and stretching his ring. When it seems to relax, I add a second finger, cueing an inhale from Avery. I gently swirl them and rotate them, moving in and out only slightly. I move my mouth to his thigh, sucking on the skin there as I focus my eyes on his hole.

The suction seems to excite something in Avery, and he moans loudly while pushing down on my fingers, trying to bring them more deeply into him. As he does, I scissor them open and closed while rotating my hand, stretching the muscle in as many directions as I am able.

“More, Finn. Please.”

I bring my ring finger up to his hole, not yet pushing in, but rather tracing around it while my first two fingers continue their job. Finally, his eager hole opens enough for the third finger. I look up at his face, noticing a sheen of sweat across his chest.

“You good, Ave? Let me know what you need, okay?”

He opens his eyes, though they remain hooded with pleasure.

“Feels so good, Finn. I just need you, okay?”

Not quite as convinced of his readiness as he is, I continue to work at him. I bring my mouth back to the head of his dick as I do, licking up the precome I find there. My fingers are deeper now, and every now and then, they seem to hit the angle just right to make a little more flood my mouth.

“Oh my God, Finn, please. Please.”

I’ve never heard Avery beg before, but it’s a sound I could get used to. I finally decide to give him what he’s asking for, pulling my fingers out so I can fumble with the condom. As I do, his hole winks at me, opening and closing of its own accord.

“How do you want this? I know some people say it’s easier on top or on your knees.”

He shakes his head, grabbing one of the pillows from the head of the bed and shoving it under his hips.

“I want it just like this, okay? I wanna watch you.”

Slicking up my covered cock with the lube, I nod, unable to decipher my thoughts enough to put them into words.

Yes. Want.

I line my cock up to his entrance, pushing forward gently. It’s stretching him a bit more, and I make a point to go slowly, no matter how good it feels.

And it feels amazing. The heat, the warmth, he’s hugging my cock so tight and the sensation is all I can think about. I bring one hand up to his dick, wanting to make sure he’s still feeling good.

Little by little, I keep pushing in, stroking him as I do. He’s quiet, which has me concerned. Pausing where I am, I bring a hand to his hair, swiping a thumb across cheek.

“You with me, Ave?”

His eyes drift open, soft and unfocused. He nods, still not forming words.

“You’ve got me a little worried here, buddy. Want me to stop?”

He shakes his head, clearing his throat.

“I’m just feeling a lot right now. But it’s good, okay?”

His voice is hoarse, breaking over the words. I bite my lip, unsure whether I believe him, whether I should stop.

“Is there anything I can do?”

His eyes attempt to focus on mine.

“Can you kiss me?”

Gladly. I lean down, bringing my mouth to his. He brings a hand to the back of my head, pulling me closer. I feel his legs rise to wrap around my hips and I suddenly find myself fully surrounded by Avery. The new position urges my dick forward, and before I know it, I’m fully seated inside him.

I pull back from our kiss, just a bit.

“Still ok?”