Read Story: SEASON 1 EPISODE 22

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! I slapped her on the side of her ass with my hand and told her to relax. After a few in and out strokes of the syringe, I pushed the plunger and shot most of it into her anal canal. She felt the coldish liquid and started to quiver a bit, both from the chill and the anticipation of what was coming. I used the rest of the lube on my cock, which was fucking rock hard, and touched the head to her tight little hole. She instinctively tightened.

“Annalisa, we can do it the easy way or the hard way. It’s your choice”

She held up a hand, took a few deep breaths, & nodded. I pushed & could feel the head begin to breach her hole. I kept a steady pressure and the head popped in. She jumped a bit, and it made me laugh.

“It hurts. Please that’s enough for the first time, OK?”

“I know better than to buy that. Admit you – oof – like this” I said as I pushed a little deeper and feeling her tighten around me.

“Ahhhh – I do like this” she said

And I pushed all the way in. She gasped and sputtered to get the words out

“Slow! that hurts. Please.” I raised a hand to strike her and panting she said “OK…OK…you feel good Billy, I like this. Please fuck my ass.”

I was buried will my balls resting on her cunt. So I pulled back and started to pump her ass slowly. She resisted at first, but then relaxed some. Annalisa Sherrill grunted and moaned. She apparently had not done this much, because she was tight, but after admitting that she liked it again, she began to push back into me.

There was no way I was going to last long. I mean, I WAS ass-fucking a gorgeous socialite in a Rolls Royce. So I grabbed both hips and picked up the pace. I pulled almost out & back in, and with each thrust Annalisa would stifle a cry and turn it into a groan. Soon she was pushing back as hard as I was fucking her wonderful anus. I reached under and grabbed both breasts, found the nipples, and twisted them. She buried her head into the backseat and let out a scream as I dumped my full load into her ass.

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