Yes

Smiling she said, "Well, I think you want me again!"

"You are a gorgeous woman!", I said, as I stood next to her.

"I feel something in my ass. Would you mind looking for me? Maybe you can get it out!" She said, grinning widely, and turned to bend over, spreading her legs even farther apart. Dropping down on my knees, I carefully inspected her ass.

"Huh? Nothing I can see", I said, but added, "I did find a very cute little place!"

And I placed my finger just inside the crack of her ass, slightly below her rectum, marking the spot.

"Really!" She quipped.

"I'll look a little closer!" I chided her.

Gently, I grabbed her cheeks and spread them wider, taking a much closer look. Before I knew it I had slid my finger into her rectum and began probing her ass. I heard her gasp, and then raise up just slightly, allowing me a better angle to get farther inside.

"Wow, you really know how to inspect asses, don't you?" She sighed, her breath starting to come in small pants, as I probed her rectum.

"I'd really like you to go a little deeper. I don't suppose you have a bigger tool you could use, do you?", the babysitter asked huskily, looking over her shoulder and tracing her lips with her tongue.

"I think you're in luck", I responded.