Do what she says

I pour a generous amount of lube on the butt plug, it looks like enough so I try to push it in her asshole. There is definitely a lot of resistance to the plug. "Um, Cassidy. It's not going in." I say puzzled.

She pushes her ass onto the plug to try to squeeze it in. "Fuck, why is my ass sooooo tight all of the sudden?" She reaches around with her right hand and grabs the plug out of my hand and tries pushing it in. She managed to put just the very tip in. "Fuck, well can you try to use a finger and work your way up to it? If your okay with that that is." She awkwardly smirks at me.

"Yeah I guess that works." I squeeze as much lube that will stay on my finger and put more directly on her asshole. I have to really push just to get the fingernail in. "I'm not sure if this is going to work either." I apply more pressure but it doesn't budge. "Yeah I don't think this is going to work."

Cassidy is getting frustrated now. "Ugh, Why is none of this working?!?! I've been using for what feels like ever." She takes a deep breath and pauses. "Okay what if you finger my pussy with your other hand to loosen me up."

Without saying a word I slip a finger from my left hand into her pussy, she is pretty wet already. I go slow to start with but then quickly pick up the pace.

Cassidy moans. "Ohhhhh. That feels good. Try pushing in my ass more."

Using my other hand I push my finger in, and I actually make the whole finger go in. "There we go."

"Fucking finally!" Cassidy relieves. "I'm going to need you to put in another finger in both holes though."

My left hand is cramping because of the weird angle it's at. "My left hand is cramping so bad right now."

"Well you could always use your dick instead." Cassidy clenches her ass and pussy around my fingers.

I pull out my finger from her pussy and use my hand to line up my dick to her pussy, I line up the second finger for her ass as well. I give her one big thrust into her pussy and when I start pulling out I slip the second finger in her ass.

"AAAaa, fuck!" Cassidy grabs the butt plug off the floor. "Take your fingers out now." As I'm taking out my fingers she slides the plug in her. "Ooooo. So tight." Cassidy takes a moment before standing up. "Ah, thank you so much." She gives you a peck on the cheek, Gets up and leaves the room.