Meeting over a cup of coffee [MF] | 2016

She had responded to a Craigslist ad that I’d posted. “M4W - Dominant Male Seeks Deviant Fem” with a little vignette describing a scene I’d enjoy.

She was about 40, divorced, two kids and following her divorce, or perhaps precipitating it, she was now a lesbian with a partner. Except she still missed a good hard cock now and again. She was tallish, prettyish, nice rack, worked hard to get her figure back after two kids. Pretty typical Southern California suburban MILF. All this I learned in a few emails back and forth.

We decided to meet for coffee at a Starbucks that was not too inconvenient for me and on her way to work. She was a high school guidance counselor, so we met pretty early, 5:30am. I got there first, got a coffee and sat at a two top. She arrived, recognized me right off and smiled big. Clearly she liked what she saw. Awkward hug and she goes to get her coffee. When she gets back we talk, just easy get to know you small talk. We both have to go to work so its not like anything is going to happen this morning, but after about 20 minutes I say “Let’s go outside, I want to find a place where I can kiss you.” She smiles and follows me out.

It’s still kinda dark out, the Starbucks is in a strip mall and nothing else is open but there are still a decent number of people coming and going with their coffee. A little too crowded for either of our comfort. I tell her to get in her car and follow me. She does. I drive across the parking lot and park along the side of a Vons (large grocery store). In view of the main parking lot but on one is around over here. She parks next to me. I get out and meet her as she’s getting out of her car.

I push her against her car and kiss her. I start with both hands holding her head, wrapped in her hair while we kiss but before long my hands are moving down, feeling her. She kisses me back urgently. Her hands all over me. She moans as my hands rove.

I spin her around and push her against her car with one hand. The other lifts her skirt up around her waist revealing white cotton panties with pink hearts covering a slightly sagging but generally shapely ass for a 40 year old. The panties are not typically my cup of tea but on a woman of her age they are out of place enough to be a little deviant, which I do appreciate. I spank her ass. Hard. She lets out a deep moan. Repressed things lurk inside this one. I spank her again and again. I forget how many times. Then spin her back around, kiss her and grab the front of her crotch. She responds aggressively, grabbing my crotch and immediately feeling my hard cock. Feeling how hard I am and knowing we’re in public with people all around she takes on a teasing, withholding tone and asks “Don’t you wish that was in my mouth right now?” She’s emboldened, knowing it can’t be.

I pause a moment, look at her, asses her arrogance and the ache in balls (it’s been two days since I’ve cum). And I call her bluff. With one hard shove I push her to her knees (skinned them both, I’d later find out), whipped my belt and fly open, pulled my cock out with one hand and pushed her head down on it with the other.

WIth both my hands holding her head in place I then administered what can only be described as a relentless facefuck. She did manage to get one hand around the base of my cock and thus spare the back of her throat from the worst of it. Which, though frustrating to me at the time, was probably for the best. She couldn’t deepthroat and probably would have puked if she hadn’t been able to keep my cock from hammering her throat unimpeded. As it was she took it well.

It didn’t take me long, two minutes I’m guessing, before I could feel the orgasm building up from deep inside. I didn’t hold back. I went for the kill, faster and faster until it burst out of me like fucking freight train. Both my hands held her head as tight and deep on my cock as I could while I came. A magnificent, cathartic full body orgasm. I held her head firmly in place, pinned against my body through each forceful spurt of cum. She tensed and squirmed. I could feel her fighting her body, fighting so hard not to gag, not to puke as my cum flooded and overwhelmed are already strained mouth and throat. And you what? She did it. She conquered it. She didn’t puke, she didn’t spit up. A little leaked out, a few dribbles out the corner of her mouth but that’s all. She swallowed the rest. Two gulps, maybe three. I released her.

She looked up at me as I tucked my cock back into my pants. Her jaw hung down, my cum still on her chin, a look of stunned disbelief across her face. But in her eyes, deep in her eyes there’s something more… an excitement, a recognition of something lost, somewhere deep inside she felt more alive than she had in a long, long time.

True story.