SOLD!!! – Pt.11

Annalisa Sherrill lived in a really nice set of condominiums along the edge of East Bay. They were double-decker and arranged in groups of three, with each group having a connected parking garage. She parked in her marked space near a wall, and at my direction she walked around to the passenger side. This vehicle had the extended rear so the doors opened very wide. Perfect.

“Step back here, and lose the coat.”

“Here? Someone will see.” Always the games.

“So is that a No?”

Without another word she did as instructed, swiveling her neck constantly looking to see if someone was watching.

“Are you planning to do me in the butt?

“Good girl” I responded. “Very smart. Now bend over into the backseat so I can fuck that ass”

Annalisa genuinely hesitated, looked around, and realized I had planned better than I was letting on. So she slipped back into character. “Please. No. Someone will see. It will hurt”

“I’m giving you what you have asked for, and per you, you paid well. Don’t you want your money’s worth? As to Pain? Maybe Yes. Maybe No. Only one way to find out.”

I grabbed her by the shoulders and spun her so she faced the backseat. She obediently leaned over, and wow was it ever a sight. 50’s or not, Annalisa Sherrill had an incredible body. I put one knee between her legs and gave her a bit of a nudge, as I leaned around her and kneaded her nipples, feeling them harden. I got behind her and began to position myself, rubbing my thumb on that butthole.

“Please. Not dry. You’ll kill me”. Again the game, but this had some truth to it, one I was fully expecting

“So you’ve done this before. Then you know to relax or it will hurt even worse.” I relied with a tiny laugh. Then added, “No worries, Doctor Billy has juuuuust the thing.” I fumbled a moment, finding it in my pants, and pulled out a veterinary syringe I had filled with Astroglide, and after shooting a small amount on my finger to lube it up, I started working it into her ass.”

“OH…SIR! What’s that!?” she exclaimed as she also tightened her ass.

Whack!