Slip a finger in her ass

While I licked her pussy, I sliped a finger into her slit ostensibly to stimulate her, but I wanted to make sure it was lubed up for what I wanted to do next. I figured this was a low-stakes way of seeing if she would be into anal.

Once I had my finger lubed up, I began to sloppily eat her pussy, moving lower on her until my tongue brushed her asshole. I heard her gasp as my rough tongue swept over her crevice. I slathered my tongue over her ass again, eliciting the same response: a shocked gasp. I decided to really see what she would stand so I started to finger her pussy, and pushed my tongue into her asshole. She gasped and moaned at he dual stimulation.

Once I had her ass well lubricated with my tongue, I swapped back to her pussy and started to push my index finger into her ass.

"Uhhh...What are you doing?" Jennifer asked. Her asshole was so tight I couldn't get my finger in. I didn't want to press too hard and risk hurting her though.

"Just relax," I said in-between laps on her clit.

"Please don't," She moaned. "I've never done that before." Although she was telling me to stop, her hands cradled my head and pulled me closer to her pussy. Maybe she really liked anal but the coy role-play made it hotter for her. There was a way to find out. I pushed my finger into her ass. Just a little. Just up to the first knuckle. She gasped loudly, and seemed to hold her breath. I went back to nibbling on her clit to help ease her into the anal penetration.

"Oh...My...Fucking...God..." Jennifer squeaked as I slid my finger in up to the second knuckle. I had eased back on my tongue fucking her pussy. I was just lightly flicking her clit, and allowing her to get used to my finger in her asshole. After a few minutes I began to slowly fuck her asshole with my finger.

"No...no...oh please..." She gasped. My erection was hard as steel, and I really wanted to be inside of her now.