Fisting With A Craigslist Milf free porn video

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This story happened about a 3 months before my last story, its the summer of 2010, Im miserable, lonesome, and feeling down about just about everything. That means its time to hunt some strange on craigslist.

An add appears in women for men, its title reads something like "seeking man who likes anal play." I like anal play, though I had never done it with anyone else, so why not give her a shot?

I send her a message with a pic of me using some of my toys, I fully expect her to: 1. be ugly, 2. be a man, 3. never respond to me, or 4. be a real live woman.

Well she was #4, and she was a 40 year old cougar with an amazing body (pics are in my profile under old craigslist hookup). After driving out to meet her we kicked back, had a few beers and exchanged some small talk. Then she made her move, she scooted up next to me and slid her hand between my legs saying "I want this." She opened my button down shirt, licking the center of my chest, working her way down, unfastening my pants, unzipping me, then she slipped my cock into her mouth. She sucked me until I was hard then leaned back looked up at me while stroking my cock and said "Nice."

She stripped, laid back on the couch and presented herself to me saying "I want you to eat out, make me cum!" So I fell to my knees, sucked her clit into my mouth, began flicking it with my tongue as I worked her in and out of my mouth. She moaned like a filthy whore, bucking into my face covering my chin with her wetness. I slipped a finger into her and immediately she said "More!" so I slipped another finger, then another, soon I was using all four of my fingers in her cunt, she was growling with pleasure, scratching my shoulders and neck as I brought her to orgasm. When she finally came, she told me to bend over.

As I bent over I thought "This is it, the first time someone does something to my ass!" She takes my butt plug, lubes it up, and works it into me ever so slowly. "That feel good baby?" she asks, I moan out "Oh god yes!" She's working it in and out of me, stretching my hole, then she pulls out the plug and starts working me with her fingers. She fits 4 in with ease, she says "I've never fisted a guy before, I might be able to get all of my hand in!"

She keeps stretching my wider and wider, working her hand back in forth, until finally she slips her whole hand in. "Holy shit!" she says, "That's fucking cool!" My eyes are rolling back in my head, I've never been this stretched and full at the same time, I'm leaking cum and I don't care, this is amazing! She grabs her cell phone and takes a picture of her hand in me, I hand her mine so that she can do the same but she tosses it aside.

Now she grabs my massive black dildo, "I want you to use this on me like you want me to use it on you." She spreads herself open and I slide the huge cock into her waiting hole. I start working her harder and faster "Yeah, is that how you want me to fuck you!?" I keep fucking her, she screams out in ecstasy as she cums on the huge rubber dick. I pull out the toy and start fingering her again, all four fingers, I begin working my thumb into her. "It wont fit!" she cries as I continue working my hand into her, "Oh my god, its so much!" she exclaims as I near the largest part of my hand. Then my hand slips fully into her up to my wrist, she cums instantly and growls with furious pleasure. I clench my fist inside her, start pumping my hand back in forth in small strokes, clenching and unclenching my fingers, I can feel her pussy gripping my hand as she cums once more.

She says "My turn, you're going to get it." She spins me around, bends me over, and slams the dildo into my ass. She rams me hard, fast, and deep making me cum, then she keeps going until I get hard again. Once I'm hard again she slips my cock inside her and starts grinding me while railing my ass with her dildo. I cum almost instantly, the pleasure is mind blowing, she pulls out the dildo and leans back smiling

"I want you to fuck my hole and fill me with your load" she says, gazing into my eyes while stroking my cock. She leans back, and I slide into her with ease, then she clamps down on my cock, tightening her cunt to the point where I can barely get inside her. I ram her clenched pussy as hard and as fast as I can, the sound of her groaning under me, her nails digging into my back, her heels spurring me to fuck her harder and harder. I shudder and grunt, cumming what little I have left deep inside her, she grabs the back of my head and shoves her tongue into my mouth, kissing me wildly.

"We should do this again sometime."

And we did, 2 more times...

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Damn, you really feel like you're getting into some special kind of shit when you look up a website, and it seems that the page has "vip" as the domain name. It gives off a spooky feeling, especially when the main thing with the website is the fact that it is all about girls and guys fisting each other. Well, so far I have not seen dudes getting fists up their asses on Fisting.vip, rather, they were the ones who were shoving their hands up inside people's butt holes and their vagina's. Does...

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1 year ago
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HQporner MILF

Why do MILFs give me such a rock hard johnson? Is it because they're so stressed they always need a good pounding to get the kids off the mind? I have no idea since I'm not a fucking woman and no goddamn parent. No, I think that MILFs are fucking sexy, refined, know what they want and because they're such good parents… goddamnit, they deserve a fucking that they can finger themselves to for years to come, okay?Show me a MILF that's too busy making shit work, and I'll show you one that's ready...

Mature Porn Sites
1 year ago
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SxyPrn MILF

What is it about hot fucking MILFs that makes your dick stop whatever it's thinking about and turn its attention to these refined, sex beasts? I know I'm not alone, either! These little pricks you see around college campuses wearing their stupid fucking hats and chasing young freshmen with fuck-all pick-ups lines can keep the inexperienced teens whining that they, 'have to put their mouth on that.' Give me the goddamn cougar that, 'yes please,' and, 'how deep you want me to blow it?'...

Mature Porn Sites
3 years ago
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Fisting Cheryl

First impressions whether they be online or in person are not always accurate. I had posted online a thoroughly debauched tale of fisting and stretching – one of many. It is always good to get feedback and I often get asked if the stories are real or 100% fiction. The answer is a mix of the two. One of the stories elicited a response along those lines from a reasonably new user from the particular site I posted too. It is easy to become dubious of new posters that have profiles with very...

2 years ago
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The Branded MILF

The Do-gooder MILF The Do-gooder MILF -2 The Do-gooder MILF -3 MILF Meat The Do-gooder MILF -4 BASTARDS The Do-gooder MILF -5 She is Mine Oh this is so sweet, my Tommy has her tits in his hands and I am grabbing them too. Oh shit, we are working together. I can actually feel him throbbing inside her. I can feel him cumming. Ah the Bitch is moaning. She likes it. Tommy shot his load in Joan’s ass. Come on, one of you guys, fuck my ass. It was hard to tell if she really...

4 years ago
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Doing A MILF

"Hey, Amy," I said, walking into her room."Hey, Ben," she responded, turning to me. "How have you been?" she pondered before kissing me.I failed to answer and just checked her out for a moment in silence."Does that mean you like the top, Ben? Is it all the colors?""And the black pants too, they perfectly match your hair," I answered, feeling a few strands. 'I just want to see it off you though, with me not wearing anything either.'"You're staring again, dude, what's going on, and...

MILF
2 years ago
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Doing A MILF

"Hey, Amy," I said, walking into her room. "Hey, Ben," she responded, turning to me. "How have you been?" she pondered before kissing me. I failed to answer and just checked her out for a moment in silence. "Does that mean you like the top, Ben? Is it all the colors?" "And the black pants too, they perfectly match your hair," I answered, feeling a few strands. 'I just want to see it off you though, with me not wearing anything either.' "You're staring again, dude, what's going on, and please...

MILF
3 years ago
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MindControlled Blowjob Bliss Chapter 6 Blown by the Fertile MILF

Chapter Six: Blown by the Fertile MILF A Belt Buckle Mind-Control Story By mypenname3000 Copyright 2020 Notes: Thanks to WRC264 for beta reading this! Things changed at school rather quickly. With my older sister's help, I started dividing the girls up into different categories. Some became whores. Literal prostitutes. These were the hottest girls that I would sell to the boys who attended my college. The twins, Rosalita, Janet the lesbian, and others were sold to the boys for $50 for a...

4 years ago
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Incestuous Flesh Massage Chapter 7 Sisters Tease the MILF

(An Incestuous Harem Story) Chapter Seven: Sisters Tease the MILF By mypenname3000 Copyright 2019 Note: Thanks to wrc264 for beta reading this! The Armstrongs would be here in an hour for their second lesson from my brother, Clint. It was two weeks since that wonderful Saturday morning when my brother showed Mr. Armstrong what sort of wife he had. Two weeks since she was spanked and fucked and shown to be a cuckold. Clint was having fun teaching Mr. Armstrong to control his wife. The...

1 year ago
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YesPornPlease MILF

There is a thing with mature women that I am sure we can all agree with. They are all grown in a ridiculously sexy way, and they fucking know what ticks for them as well as how to get it ticking. In fact, I must admit that those who are into the MILF kind of porn are mostly freaky assholes who want something close to real. Also, there is the fun in seeing some massive load of porn experience thrown into the mix.From the handjobs, blowjobs all the way to lengthy cock rides. It'sIt's almost as if...

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2 years ago
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Futa Daughters Naughty Temptation 10 FutaMommy and the Hot MILF

Chapter Ten: Futa-Mommy and the Hot MILF By mypenname3000 Copyright 2020 Note: Thanks to Alex for beta reading this! Madeline Marlow I stared in shock at Lupita Reyes, the math professor, staring with horror and disgust at us. She had caught me getting ass-fucked by my futa-daughter while I licked out Aoi's pussy, making the student cum on my face. Her cream dripped down my chin. “Madeline Marlow!” Lupita gasped in shock. “You're fucking the students. What is wrong with you? And one of...

2 years ago
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Craigslist Encounter with Busty Mature Woman

This was the first time I had actually met with someone from Craigslist. I had put an ad up saying that I was looking for a busty woman to give me a blowjob and let me cum on her tits in my car. A few days went by with the typical spammers and scammers until I got an email from this big titted cougar. She replied "hey, saw your ad and Im very interested in meeting up with you. I think it'd be hot to suck your dick in your car...while parked in my driveway." She sent a pic of her body, no face...

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