Confessions of a Cougar Chaser

[joinus]

Hello everyone,

I’m a guy in my early thirties, currently embracing a new chapter in life. A few years back, I came out of a long-term relationship that had defined much of my twenties. The breakup gave me space to reset—to realign my focus, enjoy life more freely, and build a sustainable income doing what I love.

Along the way, I’ve also reconnected with some of the deeper parts of myself—desires, fantasies, and curiosities that I hadn’t fully explored before.

Since I was younger, I’ve always had a soft spot (and a hard one) for mature women. I still vividly remember the first porn series I got hooked on: My Friend’s Hot Mom. Something about confidence, experience, and that delicious sense of the forbidden has stuck with me ever since.

This series is my way of diving into those fantasies and sharing them with anyone who finds them just as irresistible. All stories are written in the first person—some inspired by imagination, others sparked by memories I probably shouldn't admit to. Either way, I hope they stir something in you the same way they do in me.

Thanks for reading—and welcome to my world.

P.S. One of the main reasons I decided to write this series is because of the taboo nature of the characters involved. It’s not something I can openly share with people in my real life. At the same time, I’d love to connect with others who share a similar interest—and hopefully learn a few tips and tricks along the way when it comes to meeting more mature women.

[joinus]

Part 1: The Diamond in the Rough

I joined the company a few years back—a sizeable multinational with a headcount well over a thousand. My role sits within the business development team, client-facing, fast-paced, and constantly keeping me on my toes. There were a few women in the team, but the one this story is about—let’s call her KF—always stood out, though not in the way you’d expect.

KF is in her early forties, with a sweet, quietly charismatic presence. She has an adorable daughter, and from what I’d gathered through office gossip and quiet observations, her marriage hasn’t been the same since her child was born. It’s one of those "still-living-under-the-same-roof" arrangements—technically together, but emotionally long separated.

When I first met her, to be honest, she looked tired. Worn down. Like someone who had quietly resigned herself to the background. She wore outdated office attire that aged her unnecessarily—muted colors, boxy cuts, zero intention to flatter her natural figure. Even outside the office, she was always wrapped in baggy, shapeless clothes that covered her from neck to ankle, like she was trying to disappear. Her face was bare, her complexion dull with fatigue, framed by dark eye bags that told stories of late nights and stress.

But underneath all of that… I saw something.

She wasn’t a hag—not even close. She was a hidden gem. A woman who’d forgotten how beautiful she could be. And I couldn’t help but be drawn to that—drawn to her. I found myself studying her, slowly piecing together what she could be with a little care, a little confidence… a little attention.

I didn’t want to just admire her from afar.

I wanted to be the one to bring her back to life.

And maybe, just maybe, make her mine in the process.

[Spymaster2]

Originally Posted by joinus

Part 1: The Diamond in the Rough

I joined the company a few years back—a sizeable multinational with a headcount well over a thousand. My role sits within the business development team, client-facing, fast-paced, and constantly keeping me on my toes. There were a few women in the team, but the one this story is about—let’s call her KF—always stood out, though not in the way you’d expect.

KF is in her early forties, with a sweet, quietly charismatic presence. She has an adorable daughter, and from what I’d gathered through office gossip and quiet observations, her marriage hasn’t been the same since her child was born. It’s one of those "still-living-under-the-same-roof" arrangements—technically together, but emotionally long separated.

When I first met her, to be honest, she looked tired. Worn down. Like someone who had quietly resigned herself to the background. She wore outdated office attire that aged her unnecessarily—muted colors, boxy cuts, zero intention to flatter her natural figure. Even outside the office, she was always wrapped in baggy, shapeless clothes that covered her from neck to ankle, like she was trying to disappear. Her face was bare, her complexion dull with fatigue, framed by dark eye bags that told stories of late nights and stress.

But underneath all of that… I saw something.

She wasn’t a hag—not even close. She was a hidden gem. A woman who’d forgotten how beautiful she could be. And I couldn’t help but be drawn to that—drawn to her. I found myself studying her, slowly piecing together what she could be with a little care, a little confidence… a little attention.

I didn’t want to just admire her from afar.

I wanted to be the one to bring her back to life.

And maybe, just maybe, make her mine in the process.

Good start bro, you write well. I like mature women too. There’s something so alluring about them that the SYTs do not possess. Think Sharon Stone, Diane Lane, etc. When I was a kid, I was already drawn by one particular mature woman - my neighbour. She’s Taiwanese and married to a local. She’s fair and has beautiful features. Once when I was at her house playing with her children, I accidentally saw her in her bedroom in her dark blue plain bra and panties. OMG that image will forever stay with me.

[Convolvulus]

Good start bro TS, please continue

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Part 2: Before the Transformation – KF's Original Look

This is how KF used to look when I first met her—before I started to subtly polish her up. She dressed in outdated office wear. Completely barefaced, always reserved, and with an air of someone who had long stopped investing in herself.

Back then, most people barely noticed her. But I saw something else—a quiet elegance buried under years of neglect. I knew she was a hidden gem, and I was drawn to the idea of helping her rediscover her glow.

Here’s a glimpse of KF back then, just as she was.




Let me know if you still wants me to continue after seeing how KF was.

[funfox]

Do continue TS. Some points to encourage you ✌️😃

[joyopo2]

I’m a guy in my early thirties, currently embracing a new chapter in life. A few years back, I came out of a long-term relationship that had defined much of my twenties. The breakup gave me space to reset—to realign my focus, enjoy life more freely, and build a sustainable income doing what I love.

[joinus]

Part 3: The Woman Beneath the Routine

After weeks of casual chats and shared moments over coffee breaks, our conversations started to deepen. KF wasn’t just a colleague anymore—she became someone I genuinely wanted to understand.

She eventually opened up to me about her life. The picture became clearer.

Her days were consumed by responsibilities. Between her demanding role at work and raising her daughter practically on her own—thanks to a cold, distant marriage—she had no time left for herself. Everything she did was either for her job or for her child. There was no space left for KF, the woman.

Interestingly, in spite of the frosty state of her relationship, she never once mentioned her husband. Not directly. Not even a casual complaint. It was as if he simply didn’t exist in her personal narrative—just an invisible wall she had quietly learned to live around.

That silence told me everything.

I took my time with her. I didn’t push, but I did offer gentle nudges—reminding her that life isn’t just about fulfilling roles and responsibilities. I told her it was okay to recalibrate. That neglecting herself wasn’t noble—it was just self-abandonment. I suggested that maybe, just maybe, dressing up, taking care of herself, and investing in her own happiness wasn’t selfish... it was necessary.

At first, she brushed it off with polite smiles. But I stayed patient. Persistent.

Eventually, after a fair bit of convincing, I managed to get her to join a small group of us for an after-work dinner. It wasn’t a big occasion, but to me, it felt important. I wanted to see what she would be like outside of work—how she carried herself, how she dressed when she didn’t have to stick to corporate uniforms. More importantly, I wanted to see how she responded when someone—I—gave her the kind of attention she’d long been deprived of.

That dinner would be the first small shift in a slow, steady unraveling of the old KF.

And I couldn’t wait to see it.

[joinus]

Originally Posted by Spymaster2

Good start bro, you write well. I like mature women too. There’s something so alluring about them that the SYTs do not possess. Think Sharon Stone, Diane Lane, etc. When I was a kid, I was already drawn by one particular mature woman - my neighbour. She’s Taiwanese and married to a local. She’s fair and has beautiful features. Once when I was at her house playing with her children, I accidentally saw her in her bedroom in her dark blue plain bra and panties. OMG that image will forever stay with me.

u wait till I share my story with a mid fifties, she's amazing

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Part 4: Wrapped in Silence

I was absolutely shocked when I saw KF that evening.

After all the time we’d spent talking… after all the gentle encouragement… after everything I thought we’d been building—this was how she showed up? I thought there might be a shift, even a small one. And to be fair, there was.

Her appearance was a tad better than the first time I met her. Her hair was neater, her posture a little more deliberate. There was a faint trace of effort—subtle, but noticeable. Still, what she wore made it clear that she wasn’t ready to fully reemerge just yet.

She wore a long-sleeve black turtleneck that hung loose around her frame and a pair of equally baggy pants that completely erased her shape. The only skin visible was her face, her ears, and her hands. That was it.

No makeup. No jewelry. No trace of intention—just layers and silence.

It was as if she was still in hiding, still afraid of being seen. For a brief moment, I was stunned. But more than that, I was reminded just how far she’d retreated from herself. This wasn’t just a matter of outdated fashion. This was armor.

Still, she showed up. And that meant something. It was a first step—even if it came wrapped in fabric and distance.

I didn’t say a word about her outfit. I just smiled, welcomed her, and let her be. Because sometimes the first step back to yourself is simply showing up—even when you're still trying not to be noticed.

Below is a photo of KF in the outfit she wore that night.

[joinus]

Part 5: The Spark Returns

Of course, the dinner itself went uneventfully. But even that small glimpse of change in KF reaffirmed my belief—she was a diamond in the rough. She just needed someone to remind her.

We continued to chat regularly, squeezing conversations between packed schedules and deadlines. Sometimes just work stuff, sometimes deeper. There was a quiet rhythm growing between us.

Then, out of the blue, came the perfect opportunity.

Our company was sponsoring a local running event, and employees were encouraged to participate. KF casually mentioned she used to run a lot to keep in shape, but life—especially motherhood—had pulled her away from it. She said she wanted to start again, and since I’m relatively athletic, she asked if I’d run with her—help pace her, keep her motivated. Then she laughed and added, "In case I faint, you can do CPR." Her eyes sparkled just a little when she said it.

This would be the second time I saw her in a casual setting since that dinner months ago. After last time, I kept my expectations low.

She asked me to meet her at a park near her home. I arrived a few minutes early and waited near the trail entrance. When I finally spotted her approaching, I did a double-take.

I wasn’t prepared.

KF wore a cross crossbacked running singlet and shorts—shorter than anything I had ever imagined she’d wear. They were light, breezy, and sat high on her thighs, revealing toned legs and just enough curve to stop me mid-thought.

Her hair was tied back into a clean ponytail, swaying as she jogged toward me with a smile I hadn’t seen in years.

All I could think was—Damn. She's waking up. She's definitely making me hard to run.

Here is photo I secretly took of KF. Don't you think she is a gem?

[megafortress]

please continue the story bro!

[clawhammer]

Thank you for your story! Please continue