Nah, while she is okay with it....

I know it's her first time and I said I wouldn't ruin her first anal experience. It wouldn't be right just to hammer down on her ass like this.

Still we hadn't prepared her anus even a little. So any kind of penetration would be a pain in the ass for her, literally.

I stood there thinking if I would be a dick and just shove my dick her butt or if I would reign in my horney devil speaking in my ear and give her a proper warmup.

As I stood there with my dick in hand holding it at the root and moving it in circles, making up my mind.

Maisie at first just sat there and clenched down hard as she feared what to come next, but then nothing happened. She looked over her shoulder and saw me staring down at her ass circling my cock around as I was deep in though.

She interrupts me "Eeeeh what are you doing?"

I look up at her, not sure of what to say "Eeeeh..."

She starts laughing "Haha what's wrong, anal master?" She says this last part ironically "You don't know what to do? I think it's pretty straight forward..." She pauses and looks at my cock and gulps "... You're supposed to get that, thing, up my butt."

Now it's my turn to laugh "Hahaha yeah it doesn't seems so easy now does it? Don't worry it'll work just fine. It's just about how..." I stop as I probably shouldn't speak my mind.

"Huh?" She looks back up at me "What did you say??"

Mmmh fuck! I guess I have to tell her "Eeeh I was thinking... Eeeh... It's about how much you... Mmmh... Can... Well..."

She starts bursting out laughing "Hahaha I get it, haha... You are thinking about how much I can take."

Wow I'm so relieved that she take it this way "Mmmh yes maisie, that's it."

"Haha..." She stops laughing and get a little bit more serious "Don't worry too much about it okay? Just try to shove in as much as you can. I'll probably regret saying that later but I'll be fine, I promise."