My Old Friend Judy Gets Her Butthole Punished One free porn video

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Judy. She was a mostly platonic friend that I used to know. I met her when she started as the hostess at my favorite Mexican place about twenty three years ago. She was a very hot milf. Very hot. She was about 25 with a baby and on again off again boyfriend that I eventually became friends with. She had dark black, wavy hair. A sultry Italian look mixed with a generous dose of Jewish American Princess. She was trim, a petite five foot three and maybe ninty five pounds. Big, pendulous tits, with huge areolas and jumbo sized, pencil eraser nipples. Smooth, soft, white skin. Her ass was a marvel of doughy soft flesh that I swear I could leave finger impressions in. It was very shapely, if small. Her asshole was tinted slightly darker than pink, and was a smooth large muscular ring. She was not interested in having my cock in it, but in it would go.

After licking her pussy to several shuddering orgasms, and fucking it till it was sloppy and gaping open. I rolled her onto her belly and lubed up my cock. She immediately knew what I wanted and said "No! Please not my ass. Anything but that, please." I took that into consideration as I rested the head of my cock on her asshole. I spread her asscheeks with my hands and lodged my cockhead in her butt. She went ridgid, arching her chest off the bed, her mouth open in a silent scream. She gasped and asked "Oh my god, is it all the way in yet?" I replied with a slightly sadistic laugh that only the head was in. I pressed a few inches into her clenching butthole and she gasped loudly and started begging me to "please, I'm begging you, don't go any deeper", "noo, no deeper, pleeeeease". Fuck that, I immediately sank another few inches into her ass. She was sobbing by this time, and begging for me to relent on her abused asshole. I would not. Not for at least fourty five minutes of anal pounding. She suffered under my cock that night. I yarded it out of her butt, and her asshole stayed open. It was gaping open, and flexing. Her asshole was bright red, as was the skin around it. I plunged my cock back into her, as she began to wail and beg me to stop. Her tiny balled fists pulling the sheets off, and pounding the mattress (that never gets old seeing). There were never any tears from her eyes, just vocal crying and pleading for me to stop mauling her sore asshole.

That was the first of two times we fucked. The second time, I started turning her onto her stomach, and she flipped around onto her back. She was not getting assfucked again.

She later told her boyfriend that I ****d her. He and I talked, I explained my side, and he agreed it was not ****. Particularly since she and I had sex again, a few weeks afterwards, at her house. He had not known we fucked on two occasions. She had not mentioned that part.
As I write this though, now I can at least see were she was coming from. It was a strange thing though. She came to my house to try telling me she told her boyfriend, and to warn me. I blew her off though because a new girl was on her way over and I wanted to get laid. I was astonished though, that she would accuse me of ****, since our sex was consentual. I assumed at the time that she said it because she had gotten caught fucking another guy. I was mad at her for years. Now I think she felt I ****d her tiny, tender, pink anus.

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We had a few more afternoons with Miguel that summer. I liked to think of myself as quite the wild girl, along with Judy Chavez, my chunky friend from Panama. After my experience with butt sex with him, I decided that I had proven myself to be every bit the complete woman that Judy was, that it wasn't so necessary to have Miguel's giant penis inhabit my backside. Judy seemed to have a real appetite for having Manuel drive that big boy right up her behind, but for me, the memory of one afternoon...

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Judy and her husband Bob were at a party at Bob's boss's house. About twenty couples were gossiping on the pool patio. Judy didn't want to be at this party, and neither did her husband. Bob was hoping to get promoted to the position of Sales Manager and they're attendance at this party was necessary. Bob had been with Green Enterprises for twenty-five years and felt that he deserved the position. In fact, John Green's father, who recently passed away, had told him that he was giving Bob...

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