The Best MILF Story You’ve Ever Read

jtrain9 years ago

Sometimes I’ll read a story on this website about some guy and his amazing MILF story. None of them sound like a reach at all. I mean, why wouldn’t a woman of a certain age want to be a guy’s fifth time? Right. She HAS to want that. The issue is that the stories leave me, how do I put this, hard without cumming. They never live up to the hype. Reading them makes me feel like one of these MILFs riding a boy with his eyes closed who cums after thirty seconds. And it’s not that I’m some sort of MILF story connoisseur. I just have a better one.

Like any other Wednesday night, I’m hanging with the boys at Chuck E. Cheese’s. We go for the MILFs, but we hang for the skeeball. Skeeball is a lot like golf — you don’t play enough to be good at it but your friend with the least talent is considered the worst at sex. We’re mid-discussing how our skeeball scores reflect our penis size when all the sudden this MILF strolls up to our game. And oh man, what a MILF. Think about the type of woman who got on the executive track with a marketing company. She worked long hours and didn’t really have time to date or commit to a real relationship. All the sudden she’s forty and still single. The men her age want someone younger and the men who will date her can barely walk. She decides that she had the strength to create a great career, so she knows she can be a single parent. She visits a doctor and he tells her in-vitro is an option but, due to her age and the medication used to have a baby, there are risks. THAT’S the type of MILF I’m talking about; Had a kid later in life, in her fifties, never been married, wears pantsuits, high-risk pregnancy, HOT AS FUCK, MILF.

And this MILF is just standing there. Her hair was flaming red and looked like it was just done at the salon. She was tall. Almost too tall. Like an oak tree you’d want to climb. She was the perfect combination of Rebecca Lobo and Estelle Costanza. She was five feet away, staring with her arms crossed like we didn’t do our homework. Probably just sopping wet from our bulging biceps throwing skee, the Chuck E. Cheese’s pizza grease glistening off our cheeks. When all the sudden, in a “principal telling you recess was over five minutes ago”-like tone she says, “You guys are pretty good with those balls.” I looked at my buddies. No words were even said. I just nodded like a general telling his troops to fall back. I walk towards the large woman and confidently say, “You should see what I can do with this dick.” At this point, all the kids had stopped playing in the ball pit. All eyes were on us. Estelle Lobo and I stood across from one another. We were close. Like too close for normal conversation. She leaned in and whispered into my ear, “It’s my son’s birthday, why don’t you come over for some cake.” I knew I was in for a night. I mean, she didn’t say “cake” like she meant actual cake. It sounded like she had other ideas.

We go over to the section of Chuck E. Cheese’s with the tables and the animatronic puppets that sing happy birthday. There are about twenty seven-year-old kids sitting at the table. She sits me down next to her son. She puts a plate in front of me. She gives me a hat and a juice box and a package of Dunkaroos and serves me a piece of cake just like I was one of the other kids. I can’t explain how hard I was at this moment. I mean, this was the full-on mom experience we all want. I was about to dig into the cake when MILF looks at me angrily and asks, “Have you washed your hands?!” I hadn’t been spoken to like that since my actual mom. So dirty. So hot. So MILF. I get up to wash my hands and as I walk past her she whispers, “I hope you ate your vegetables.” And now I’m just too hard to be at a Chuck E. Cheese’s. I tell her to meet me outside.

I’m in the parking lot. MILF struts out of Chuck E. Cheese’s like she’s on a mission to take a dump. It’s like Rob Gronkowski wearing a Ronald McDonald wig is hunting me down. She grunts, “Come on” as she leads the way towards a mini van. The back door slides open. There’s birthday stuff all over the back. There’s only one seat and it’s covered by a toddler-sized car seat. She tells me to strap in. I sit in the car seat and she starts strapping on the belt. It was like I was getting onto a MILF roller coaster. She straddles me as she tells me to cry like a baby. I cry. I actually cry. She starts cooing, “Oh baby, it’s ok. It’s ok. Mommy’s here.” I came immediately. I don’t know if it was the angle of the car seat or the sound of her voice. I just couldn’t keep it going. It was too hot. But she was angry. She unbuckled the chair. Basically threw me out. As I’m next to the minivan, her kid comes outside holding a single “Happy Birthday” balloon. MILF screams, “Let’s go Atticus!!” And then she turns to me, sneering. I thought steam would come out of her ears as she growled, “Do your fucking homework next time.”

I walk away. Fully erect..

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