My old friend Judy gets her butthole punished one

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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Categories: AnalHardcore
Posted by badnewzsho
2 years ago    Views: 940
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1 year ago
Ed = were. Typo.
1 year ago
She actually did not tell him that we fucked twice. I told him, and that is when he went from being mad at me, to being mad at her. Particularly when I told him that the anal sex occurred on the first time we ever fucked, not the second time. Then he knew that things Ed not as she was leading him to believe. I don't know why she would think I was not going to tell him about the second time after her accusation .
1 year ago
She was super religious and believed her man is fully in charge. I think that's why she told him. She felt guilty, for sinning. He already knew he was biting off more than he could chew, do to our first run in at a local restaurant, so smacking me was not an option for him either. Plus, by this time we were friends. Those two were breaking up every other week, and he knew she was seeing me in between. It was a strange triangle. We all remained friends for another two years until they moved to California, and lost touch. The timeline is a bit fuzzy, but it was some time after the buttfucking incident that she told him. I had already gone through at least two other girlfriends and was working on the next one when she showed up at my place to tell me. I managed to sort it out before my future ex wife showed up for sex. I was only half listening to her as she was telling me this crap. I wanted her to not be there when Aileen showed up, so I could get laid. Writing this down reminds me of just how shallow and morally bankrupt I used to be.
She was a good person, and I used her for sex. In my defense though, I was upfront with her, that I was not interested in a relationship.
I bet you would like to hear about my Chinese ex girlfriend, Wu Chang E. I went to Shenzhen China to meet her.
1 year ago
I understand where you're coming from. Not politically correct to say this but I agree, women don't always mean no when they say no. I've also had a lot of experience of that. What I don't get though was why she told her boyfriend. Just to get back at you for fucking her in the ass? But surely she would lose out even more by doing it. Assuming she was never going to tell the police, all the boyfriend could do was smack you. He was going to persecute her for a long time knowing that you'd fucked more than once.
1 year ago
Today I would agree with you. My thinking at the time was that if she didn't want it, she would have made some effort to resist physically instead of just saying no. The second time we had sex, I rolled her onto her stomach and as soon as she felt my cock touch her asshole she rolled over onto her back saying "no!", and that was that. We fucked for a few hours and I never tried to put it in her butt again.

My fiancee tells me all the time that I can't fuck her ass, and the last thing she wants is for me to stop giving her anal sex. She loves it in her asshole! I've been with more than sixty five women in my life, and my experience has been that "no" is not always as simple as it sounds. Sometimes it absolutely means "NO!" but more often it means something else. Judy meant "NO!". I made a mistake, but she forgave me.
One thing I do remember though, is after I finally pulled out of her ass, she grabbed my cock and licked the cum off and sucked me until I was completely soft. She couldn't have been that mad at me if she did that. She also fucked me again two weeks later. That is why I was so confused by her later claim.

What do you think?
1 year ago
Sounds like you dodged a bullet there!
2 years ago
Unfortunately it happened a long time ago, and that is the best of my recollection. Glad you liked it. :-)
2 years ago
Good story,I wished it was a little longer. Thanks