The MILF

Nov 16, 2009 • Arrow, Diary •

I was 21, she was 39.

I met her up at a Mexican restaurant over margaritas in Northridge. If only we were the same age and she didn’t have two kids, we could have been a couple.

Our second “date” was at her place. She made me pizza with Trader Joe’s dough, she kicked my ass at Scrabble, I played some piano for her. Then the clock struck twelve and it happened to turn into St. Patrick’s Day. I smiled and jokingly said, “kiss me, I’m Irish.” Under her breath, she went, “finally,” and leaned over.

We made out on the couch, but soon were on the floor. I massaged her back as we kissed and that made her hot (she said so). She took off her shirt, but we soon made our way to her bedroom. She lit candles and I went down on her, writing the alphabet with my tongue, eventually getting deeper, making hips swerve unintentionally.

Soon, that moment came, it was a beautiful moment too. The condom was on and I was on top of her. Outside, I was confident, inside myself, I was ecstatic. I was about to make love to an older woman, a woman who was funny, who looked like Sela Ward combined with Sheryl Crow, a woman of great intellect and adventure — I was her first young guy, as she was my first older woman. The moment I was inside of her, I said to myself, oh my god, this is actually happening. It was amazing.

We danced in bed, against the wall, screaming hard, riding on top. At one point, in a moment of inspiration, I grabbed the candle and spilled the candle wax over her breasts. She yelped, but it was hot, more than literally.

Then we spent an hour on the floor, 69ing, passionately.

After three hours of tantalizing sex, we came to a rest, tired, satisfied and in amaze. She said she was surprised and wasn’t expecting that great of a time and endurance and I was happy I could please.

The only sad part was no morning sex, she had to kick me out that same night. Her ex was coming over early in the morning to drop off the kids and there was no need for this kid to be there when that happened.

I drove home that night on the 101, still hard as a rock, thinking about what happened. That moment, when I first entered her — it was beautiful. Will I ever feel that again?

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Care to chat? Leave a comment below and follow me on Twitter at @Arrow405

  • Jay

    Okay, so, assuming you like them older but aren’t a homewrecker, how do you FIND the single moms? Where? Teach us.

  • Arrow

    Hey Jay. Single moms come from all walks of life. I wouldn’t say there is one place, one way to meet them. Some are met in online dating or social networking sites and some are met via friends. I’ll try to work up a post for you, k?

  • Pingback: 7 Tips On Meeting Older Women (And Where To Find Them) | Sex and the 405()

  • Tyler Knox

    Alphabet with your tongue? Arrow I understand you are a “younger” guy…but most of us move away from that oral technique soon after we get a driver’s license…

    Next time, at least go with the French alphabet…making that cedea under the c will make her go unglued…

  • http://repeatfirsttimeoffender.blogspot.com Alex

    Wow, Jay wants MILFs? Thank you, kindly.

    Tyler, don’t be rude. I’ve met very few guys who have any sort of clue about oral with a woman and are therefore scared of it. Let’s not discourage it, any which way it comes.

    Arrow, this made me grin. Really wide.