Colleen, Becoming a Cougar
written by:
Naughty Miranda

So this is fifty. Devouring doughnuts delivered by Derek from Accounting, while my workmates... having run out of ways in which to ask me how I intend to celebrate the day... are discussing their own weekend plans instead. Not that I blame them for that. There's only so much "that sounds fun" you can squeeze out of my "maybe I'll watch a movie."

And there's only so much fun you can derive from doing so.

Not that I'm feeling sorry for myself. No, maybe I never did expect to be widowed before I hit forty; nor did I really consider how difficult it might be to meet someone else in the years that followed. But it was my decision to downsize from the house to the apartment; and mine to fill at least a few of the hours by taking a little job. Frank (my late husband)'s life insurance pay-off was generous enough that I was able to live debt free, but it didn't fill the time that yawned between dawn and dusk, and it didn't fill the silence of the place, either.

It didn't send me a birthday card, either. Home that evening, pizza'd and wine-glassed, I was already halfway to switching the television off, bored out of my boots by the movies I'd started, when I realized I was almost out of cigarettes too. Well, that decided it. No way was I going to sit through another hour of George Clooney flapping his jaw, if I couldn't view it through a fug of cigarette smoke too.

Down to the street level, out to Eighth Avenue. It was late on a wet January evening, but you'd not have known it from the crowds that still milled around the stores, bars and eateries... mainly eateries, I suddenly noticed. As if every other retailer had themselves been eaten, and all that remained were a succession of cutely-titled boutique snack bars. Hummus, cupcakes, falafels, cookies... you couldn't actually buy a proper meal here. But there was an eternity of fancy snacking on display.

I swerved out into the street to avoid a gaggle of especially obnoxious looking students gathered outside a bar that advertised banana-flavored beer, then back onto the sidewalk as a cyclist swerved to avoid me. Then into the deli where I bought most of my groceries, and my morning and evening coffee too. Mehmet, the owner, raised his eyebrows as he saw me. "Seven AM already?"

I laughed, although I don't know how he did it. He was behind the counter when I came in in the morning, and he was still at night, no matter what time I came by. I wondered if he ever slept, but I joined the one for the check out that was longer than I'd seen it before, casting my eyes round the grocery shelves to see if there was anything else I could pick up while I was here.

"Hey, we ride the same bus." A voice at my ear.

I turned. "Sorry."

Nineteen, twenty years old? Bright eyed and bushy tailed despite the hour and the weather and all of the other reasons we adults can conjure to blame for the fact that we look and feel like shit. A student judging from the books in the bag slung over his shoulder. An out-of-towner, judging from his accent.

"Yeah, I've seen you," I smiled. I hadn't, but there's no point in being confrontational. He smiled back and joined me in the line. He didn't have a basket; I guessed he was waiting for cigarettes too. I felt a flash of affection for him. I don't care that it's a disgusting habit, or lethal or smelly or any of those things. The tide has turned so strongly against it, I now feel nothing but admiration for the people who still smoked. Something about standing proud and strong in the face of the enemy.

"You live round here?" He was speaking.

I nodded. "Yeah. You?"

"Right around the corner. I was so lucky..." and then he was off, a convoluted saga of father's friends who had careers in the city, owning apartments that they rarely even used, and allowing him to crash there while he looked for accommodation of his own, and then he mentioned the street and I couldn't help but whistle. Serious money, serious luxury, serious security. So serious that he'd not actually dared invite any of his college friends round, in case they were turned away at the entrance. The doorman had enough qualms about letting him in every day, and he'd lived there three months now.

"Any intention of finding some place else?" I asked, and he grinned wickedly. "What do you think?"

The line was moving fast. Three, four people in front of us. I already had my "nice to meet you, see you around" balanced on my lip when he asked... or, rather, stammered, the words falling nervously over and under one another, as though he couldn't believe he was even speaking... "there's a quite good bar around the corner. Do you fancy getting a drink?"

I knew the bar, and "quite good" was not a term I'd use. But what else was I doing this evening? The prospect of returning to George Clooney felt even more unappetizing than before, and I doubted there was more than half a glass of wine left in the place. I should at least toast my birthday with something better than that... although I doubted I'd be sharing that fact with my companion. "Okay," I said, and off we went.

He bought the drinks and his ID passed unchallenged, although later he confessed that he was a little surprised... it was the first time he'd used it outside of the usual student circuit. I almost said something, but remembered my own years of fake IDs, and the fact that this place was a lot classier than any of those I ever spent time in, so I let it drop.

Besides, I was actually enjoying myself... it's surprising, but if you actually forget the fact there was thirty years between us, and we had absolutely nothing in common beyond maybe a shared sense of humor, this was shaping up to be one of the most relaxed evenings of laughter and chat I'd enjoyed since... well, in a long time. So, when a party of loud and already drunk businessmen descended on the place, and it became impossible to actually hear one another speak... and Terry (I'm sorry; I completely forgot to introduce you! And I'm Colleen, although you probably knew that) asked if I wanted to see his apartment... "well, so long as you think the doorman will let me up."

He nodded. "You should be okay."

And I was, although the apartment wasn't simply everything I expected it to be, it was all of that and more. I couldn't believe anybody lived in this kind of luxury... no, scrub that. I knew people lived like this. I couldn't imagine that they simply owned it, and didn't live in it. The view across the city alone was enough to hold me enthralled... so much so that, as I stood on the balcony gazing out at the lights, and Terry, behind me, placed his hands on my waist, I didn't step away, I didn't move aside. I just held myself still for a moment; then allowed myself to relax in his grip. Which tightened as his hands moved to meet around my waist, and I tipped my head back a little, as his face moved forward to nuzzle my neck.

I closed my eyes, and a hand was on my breast.

So this is fifty.

I'm not in bad shape for my age. I'm not going to say I'd pass for much younger... there's gray in my hair, and - let's be gentle, and say a few lines in various places. I don't tip the scale at the weight I did twenty years ago, but I don't sit and glare angrily at pictures of super models either. Between my gym membership and a generous metabolism, I'm doing okay. For my age.

Which doesn't mean I didn't nurse just a hint of trepidation as our kisses on the balcony were carried back into the apartment, and became more than kisses too, and while I'm not 100% certain who initiated the mutual undressing that followed, I was grateful that the lighting was as low as it was. Just in case.

Besides, even standing in the half light... I don't know what he thought of his side of the bargain as I wriggled out of the last of my garments. But I'd unwrapped a birthday present like I'd not seen since I was his age, and had all but forgotten even existed. Thin. Firm. Muscled. Hairs on his chest that had not yet become a forest. And a cock that I knew had been standing to attention ever since that first touch out on the balcony, because even before he pressed himself against me (and Christ, I almost came when he did!), I could feel the heart radiating off him. Feel it, and want it.

How is this going to work? The experienced older cowgirl leading the gawky young stallion to water? The wild enthusiasm of carefree youth simply thrusting caution, wisdom and just a little self-consciousness to one side?

Or a combination of both, as I took his hand in mine, as I sat down on the bed; and he - I'm still not sure whether he misinterpreted my gesture, and the position I was in; or if he interpreted it more accurately than even I was aware. But my head was at cock level, he just needed to turn... and...

And.

One work Christmas Party ago, or maybe it was two, one of the women in my office was bitching, after a few drinks too many, that she spent longer sucking her husband to hardness than he did fucking her once he'd got there. The rest of us laughed, and clucked sympathetically, and I don't know. Maybe I was the only one among us who didn't think that was such a terrible thing, or maybe I was because one of the others murmured, quite appalled at the thought, that she'd rather go without than have to do that, and a few more clucked sympathetically at that, too.

Me... when boys were just an alien race with whom I doubted I'd ever have a close encounter, I used to practice on bananas. I don't know how, or where, or even if I first learned that cocks were made for sucking. I know I'd never seen one, not a hard one, anyway. In those days before the Internet stripped all the secrets and mysteries from life, and Playgirl was as raunchy as our reading matter went, penises were soft, plump appendages that wouldn't say boo to a goose. It was in the restrooms at school that we learned what they did, and what could be done to them too, and in bed with my dreams and my 70s pop star posters that I figured out I'd like to do myself.

I was never an expert, never a whore, and never the sort of girl who you heard about in senior year, giving head to every guy she talked to. I could count on one hand, literally, the number of boys or men whose cocks I had sucked. One, my long time boyfriend and prom date, on the night I graduated High School. Two at college, one whom I married, and one shall we say who I probably shouldn't have, when my husband was on a business trip and I was at the gym. Five.

Six.

There was no subtlety, and I wouldn't have wanted it. I sat, he turned, and one hand was on my scalp, the other on his dick, and ... okay, this was all in one movement. One moment. His cock was at my lips, my mouth opened, he pushed in. He came, I swallowed, I came...

Fuck!

I've never done that before.

Never done either of those things. 
 Never swallowed, and never had someone come in my mouth before... well, not intentionally, anyway. I've often wondered about it, and thought I'd try, but guys get impatient too, wanting to stick the thing every place else, so I never had the chance. And I've never come just from sucking on a cock... not that I really got to suck on it before he was crying out in absolute glory, and I had completely forgotten how much come a teenaged boy carries around in his ball bag.

I wasn't swallowing, I was wallowing, drinking him down as he pumped and humped me, my hands clasping his ass so he couldn't get away; so he'd know how much I wanted this moment.

He wasn't huge. He was just right. My jaw stretched around him, but it was a good stretch, a welcome stretch, the kind that left you know you were doing something amazing, and "no pain, no gain" sort of flickered around the back of your mind, and breathing seemed horribly over-rated as well. His fist balled in my hair, his prick bucked and fucked my mouth. And I was coming so hard that every nerve end was screaming, to make up for the fact that my mouth was jammed silent.

Of course he apologized once it was over, collapsing alongside me with his dick still stiffer than I ever imagined it could be, because every guy has to say sorry if they come before whatever arbitrary milestone has been reached in the proceedings. But I couldn't help blurting out an incredulous "are you kidding?" Followed by, "tasting you was the best birthday present I've ever had."

Which let him know what day it was, although his was the guesstimate that shaved more than a few years (seventeen, to be precise) off my actual age, because... okay, maybe a fourteen year age gap is still a little shocking for some folk. But it's exciting for others, and he was one of them. Particularly after I made up for that lie by telling him a truth, that he was the first man (yes, I used that word deliberately) ever to shoot his load down my throat. To which he responded that I was the first girl (and yes, he used that word too. Bless him) who had ever sucked him off to begin with!

The first to ride him reverse cowgirl too, and the first to stick her cum-dripping pussy into his face and orgasm three times while he sucked at her. Probably not the first to refuse his offer to stay the night, even though it was Friday, but the first to promise that next time I saw him - well, maybe that's another story, which I'll tell another time.

But I will say one thing before I go. So this is fifty. Wow.