On his hands and knees

"On your hands and knees," you command him, "I need to prep you properly."

He eagerly complies, fully engaged in this new dynamic of yours.

Once Benz was in position, you grab the lube and liberally coat your fingers with it. Without warning, you plunge one finger into his hole, teasing and probing its depths. Benz is incredibly tight and warm, you shudder just thinking about how it would be like to be in him.

“Relax, Benji,” you tell him as you try and push the finger past his sphincter, “Relax and push out.”

Benz does as you tell him and you feel your finger slowly inch inside his tight channel. With a couple of deep breaths, you finally find yourself knuckle deep in his ass.

“I have a finger inside of you, Benji,” you tell him, “I need you to squeeze tightly on it, like you’re trying to stop a poop.”

Benji nods at you and you start feeling pressure against your finger.

“That’s it. Keep that up. Hold that squeeze as long as you can. Let me know one you can’t hold it anymore.”

Benz’s face flushes red as he struggled to do as you asked him to. He warns you that he can no longer hold on and you use that moment to plunge a second finger, surprising Benz. The second finger goes in easily without much resistance.

“How does that feel?”

“It feels weird. I feel full but not really.”

“Is it painful?”

"No. Just full."

With reassurance from Benz that he's okay, you start shuffling your fingers around in search for his prostate. You find it quickly enough, much to Benz' shock and confusion, as waves of new, intense pleasure racked his newly sexually-awakened body.