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.
***
I gave Annalisa back her panties, but that was it. It was mostly because I didn’t any of my fat jizzy cum load leaving a trail, or plopping out should we meet a neighbor (we didn’t). The whole way from the parking garage I had my arm round her or mostly groping her ass, and I hope security cameras caught it.
Yep, she was most definitely into it, squeezing my cock thru my pants as we made our way there. Once inside, I tore the coat off Annalisa. After the ass fucking she’d just gotten, I figured she be mad at me. But, to my surprise, she started to kiss me back, and fumble for my belt.
“Sir! I want you! I want that dick inside me!’
My pants were down and she was on her knees, and in a flash she had my rock hard member in her mouth and was bobbing up and down quickly. I had cum twice, but she was well on her way to making me shoot number three. But I wasn’t going to have it this way. I grabbed her hair on the back of her head and guided her up. She pointed and I led her to a really elegant bedroom.
After we stripped, I gave her a gentle push, and she went back onto the bed. Annalisa’s large breasts gave a satisfying shimmy back and forth as she landed. I grabbed both her ankles, pull her halfway off the bed, threw her legs over my shoulders and buried myself in her pussy, balls deep/all in, & in one thrust. She let out a groan of pleasure and I started to pump that twat as fast & as hard as I could.
“Oh, YES! she yelled. “Fuck me! Fuck me hard!”
“Hands behind your head, and keep them there” I said as she lay on the bed, now helpless to my pummel-fucking.
I slowed down and began to bring myself down a notch. I reached up between her legs and grabbed each nipple with my forefinger and thumb and puffed up the nipple as I continued to pump her. I alternated between working her two erasures and torturing each breast, never breaking rhythm.
Annalisa moaned loudly and squirmed, calling out & moaning thru her gritted teeth.
“Ummmmmm. I’m close! Don’t stop. Please don’t stop!”
I did stop, and she looked like I had just stabbed her. I pulled out, stepped out from between her legs and flipped her over.
“On your knees and get that ass in the air!” She complied instantly
“Reach back and rub yourself woman, and tell me what you’re doing.”
“Ohhh – I…I’m rubbing my c-cl-clit-t…”
She did as she was told, closing her eyes and enjoying the feeling. With one good push I was right back in her pussy, plugging away, happily balls deep. I could do this for a very long time, as this was my third load. So I just pumped merrily away, watching this MILF (GILF?) groan and squirm under my pounding.
When I had turned her over I had gotten a bit of KY, and now I squeezed some onto my thumb. Rubbing her starfish made her eyes pop open wide. “Keep rubbing that clit.” I said, as I could feel my own pressure building.
“Ok sir….Your dick feels AMAZING, and I want to…to….ahhh…”
Annalisa’s face was flushed red like she was angry, and her fingers were working like lightning, all while I pump-thrusted mercilessly into her. She was frowning, her eyes were closed, and she was totally tensed – so close! When I eased my thumb into her anus, the moan moved quickly to wail, and Annalisa Sherrill began an incredible gyrating orgasm. The pulsing on my cock was too much, & I proceeded to empty what I had remaining inside her womb with a mighty roar.
The rest of the eve was a bit of a surreal experience, as Annalisa first licked me clean, then curled up around me in her silk sheets, and we both slept a deep sleep. I was supposed to stay the night, which was fine, although the looks I got from the morning housekeeper, who also made a wonderful breakfast were quite something.
***
I had barely gotten home when I got a text from Brianna. “Great news Bae! Be at my place at 6.” The fucking in this “deal” had been incredible but getting out from under Twisted-Bitches’ thumb was paramount at the moment, and I drifted off for a few hours of blissful sleep.