She attempts to handle the massive dildo

Elaine uses her hands to spread her ass cheeks and slowly lowers her rear down toward the monstrous faux cock. I move the thick head of the dildo to line up with her ass hole and she gasps when she feels it push against her entrance. I move the tip around a little, spreading the lube all throughout her crack and around her tight hole, and then apply more pressure. She lowers her body a little further until the head of the dildo is inside of her.

“How is it, baby?” I ask her, stroking her cheek.

“It’s okay so far.” She replies.

“You’re doing great.” I smile at her. “But you still have a lot more to go, probably another foot at least, baby.”

I watch her eyes fill with fear, but also with a hint of determination. She takes a deep breath and lowers her body down further. Her ass hole stretches to swallow about another inch more of the rubber dick, and then then another.

“Harrrrry....” she whimpers and reaches out to grab my hand. I squeeze her small hand in mine, and we look each other straight in the eyes.

“It hurts.” Elaine squeaks, her face strained.

“You can take it, Elaine. I’m here. Keep going.” I say and kiss her on the cheek.

Her face tightens and she grips my hand even harder. She lifts her ass up a bit, then quickly pushes it back down. She screams as the giant dildo forces itself even further into her tightest hole and her eyes well up with tears.

“Fuck, Harry. It’s too big. I can’t.” Elaine whimpers.

I know she’s in pain, but good God does she look sexy with nearly half of this enormous dildo inside of her, stretching her ass hole to its limits. It might be painful now but I know once it’s the whole way in she’ll feel so good. I want her to take the rest of it. I want to make her ass cum.

“Harry... please... no more.” Elaine whimpers as a lone tear runs down her cheek.