How It Took Me Over A Year To Bang Maureen The MILF

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It was late spring of sophomore year and I needed money. I was working as a mason’s apprentice, same as I’d done in the past. It was a really solid gig. My boss, Jack, owned the company and I was his sole employee. We received most of our work from an insurance restoration company whenever a fire, flood or some other earthly disaster decided to wreak havoc upon someone’s house. We worked on anything and everything within the scope of masonry; chimneys, retaining walls, patios, you name it.

One Monday morning, as we loaded up the truck for a chimney fire job, we kicked the shit about the weekend and traded stories. My boss told me that the lady whose house we were going to was a friend of his from back in the day. Her and his wife had roomed together in college, but they haven’t seen each other in twenty years. He also told me that she was a stone cold fox and that he banged her just days before meeting his wife. I wasn’t surprised.

When we arrived at her million-dollar home, Maureen came out and greeted us at the door. She was wearing an oversized night shirt down to her knees, no bra, and light pink panties. She was in her late forties, divorced with two grown kids. Her husband cheated on her and she took him for all his shit. Despite being nearly half a century old, she had the body of a 25-year-old active girl.

The next four days, as we worked on the fireplace in her bedroom, she hung out, made us lunch and made playful remarks to both Jack and me. Neither of us took it seriously because Jack had already described her as always being playful and flirty. On the last day, Jack dropped me off to finish some minor stuff and clean up while he went out to do a few estimates.

I got up to her bedroom and she was in the shower, so I just minded my own business and got to work. After I heard the water stop, she peered out the door in a towel, said hi, and went back to her post-shower regiment — but she left the door open. I was confused. I wasn’t sure if this was a sign, a simple miscalculation on her part, or an all-out invitation to watch her lotion up in front of the mirror. I peeked a few times out of curiosity and was not disappointed. Regardless, I continued to work.

I told Jack about it on the ride home and, nonchalantly, he made it appear as if she was giving me a green light to make a move. But even if I did set aside my high standard of professionalism and try to make something happen, I would have had no idea how to proceed. This bothered me for weeks and then months. The “what if” lingered like a protein fart.

A year and a half later, as I’m killing a pitcher over some wings with a buddy at a local bar, Maureen walks through the door. No longer being employed by Jack, I abandoned my friend, summoned up the courage, and joined her for a drink. After a few neat singles, I brought up the events of that Thursday morning. Turns out Jack was right. She wanted me to look, and I missed the window of opportunity because I was too much of a pussy to try to slip into hers. Anguish overtook my whole body and I went pale. I know she could smell the stench of regret that was being exhaled through my pores because, in a weird yet exciting motherly way, she placed her hand on my my forearm and said “It’s okay honey, the past is the past… but the night is still young.”

My buddy was my ride home. I had largely been ignoring him since Maureen caught my attention and, after a while, he said he was taking off with some rando he talked up. I turned to Maureen and she said, “Don’t worry, I can give you a ride.”

It was at this point that my life changed forever. It was no accident that we ended up in the same bar on the same night. The heavens were giving me a second chance. Once my buddy left, Maureen and I continued to drink. With every margarita, she became less talky and more feely. We closed out the tab and, being a gentleman, I let her pay because “equality” and shit, but mostly because having my card declined was not exactly the move to get her clock ticking again.

We started making out on the bar patio and quickly moved to her Cadillac. She was a cougar, without a doubt, in every way imaginable. She tore off my clothes and dragged me into the backseat right in the bar parking lot. She may have had a few miles on her, but those miles gave her experience and expertise no twenty-year-old bimbo could even fathom. I came quick, no shame, but for her pleasure I kept going for another couple minutes with an empty chamber. This wasn’t like any other sex I’ve ever had. For every one of my fumbles, she had a save, and I was just glad to be off the bench.

Afterwards, we split a cigarette as we lay in the trunk area of her Escalade peering out the back window back at the bar. It was one of those extra skinny Capri cigarettes, but I didn’t mind. I had just made good on a regret that had haunted me for a long time, and that was a really satisfying feeling.

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