A Cougar’s Conquests Ch. 01: Ollie

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Ch 1: Ollie

Ollie gets more than expected when he knocks on Lisa’s door


It was no accident that Lisa’s townhouse was situated on a narrow ridge of land which opened onto a popular surf beach at the front whilst at the rear overlooked the local football ground and skatepark. In her early 30s Lisa was already a successful professional woman. She worked in IT and mostly from home…so she enjoyed the luxury of arranging her time to suit her needs…business and pleasure. Slim and attractive, Lisa had plenty of admirers…men who would have appreciated a long term relationship, but she remained determinedly single….strategically unavailable in fact in order that she could indulge her self acknowledged predatory behaviour. Lisa felt she was too young to be considered a MILF but she was certainly in the ‘cougar’ category. Lisa loved young guys. Boys who were men….men who were still boys in the eyes of the world. She was under no illusion as to her predilections. She was not after a relationship. She just wanted them for their young hard bodies, for their infectious enthusiasm, for their boundless energy and staying power, and also for their youthful inexperience.

Lisa loved tantalising a young guy who clearly had little, or even no, experience. She loved the thrill of the all too predictable chase. She loved the way a glimpse of slightly too much cleavage or the…accidental brush of hand against thigh would result in instant erection and the self conscious awkwardness which would accompany it. She loved the overwhelming desire which washed over these boys as they realised that this was no dream, that this woman they didn’t even know was about to give them all they had hoped for. Yes, Lisa could not get enough of innocent young flesh. She never tired of those wide puppy dog eyes as their cocks throbbed with anticipation and pre-cum leaked with the copious volume produced only by the inexperienced.

But Lisa also loved, on occasion, chancing on the young man who was already quite experienced. Perhaps at the age of 18, 19 or even early 20s he had already had a longterm girlfiend (or two) and knew his way around a woman’s body. She enjoyed the realisation that, whilst young and firm and smooth, this was a lad who knew how to pump her good and proper, who, turned on by a random encounter with an older woman would rise to the occasion with an ardour unmatched by older men and who would ride her again and again, his pale tight butt pounding her repeatedly. And let’s face it….she’d enjoyed more than a few! Between the delights of the fit young surfers all summer and the delicious footballers in their tiny little shorts all winter, Lisa found plenty to entertain her. And of course the skate park produced year round temptation…..


Lisa was surprised to hear the doorbell. It was Saturday morning and she was not expecting anyone. She glanced at herself in the mirror before going to the door. Peering through the security eyehole she stifled a quick intake of breath. It was one of the boys from the local football club. Not only that but it was a boy she had lusted over all last season. His name was Oliver she had discovered and she had watched more than a few games he was in last year, literally swooning at his gorgeous long legs, smooth face and an enticingly prodigious bulge in his footy shorts. But footy season had not even started yet….it was still late summer. Whatever had brought him to her door…she was eternally grateful, and if Lisa had her way….so would Oliver be.

Pulling her top down ever so slightly so it was tight over her ample tits she swung open the door, smiling radiantly at her unexpected guest. Oliver looked slightly taken aback. He stood a few feet back from the door. He was wearing his football gear; sleeveless jersey tucked into his little white shorts, striped socks pulled up and his training boots. Lisa guessed immediately that he was wearing last year’s gear. As young men of that age often do, he had grown over the summer holiday season and shorts and jersey which last winter had been snug were now distinctly tight. Not only that but clearly he had spent most of the summer at the beach, his head of hair bleached blond by days in the sun and his fair skin deliciously bronzed. And his legs had that stripe of fair skin between the bottom of his little football shorts and where the board shorts he’d clearly been wearing all summer naturally came to. He looked the very figure of a young adonis. Lisa’s eyes surveyed him from head to toe and she consciously allowed her gaze to linger ever so slightly at his crotch which was indeed a sight to behold. His soft cock lay heavily in his tiny shorts, boldly visible almost stretching to his left hip. Lisa permitted a fleeting smile to let him know she approved. Predictably he blushed, partly from knowing what she was admiring and partly because of course in his own mind he couldn’t possibly be right in that assumption. Lisa knew that Ollie, as bahis firmalar─▒ the name stuck to his chest proclaimed him to be, was indeed a prize ready for the taking.

“Well this is a pleasant surprise,” greeted Lisa, “it’s not often I open my door to a lovely young man like you….Ollie..?” she added the name with a slightly quizzical lift of her eyebrows. “What can I do for you? Other than the obvious…?” she added with a quick grin and most fleeting of glances back to his crotch. Lisa knew young guys like this well. She could read them like a book. She knew it was best to start laying the trail early on. The sooner the testosterone kicked in the more likely it was that they would be hers. Ollie, blushing furiously now, opened his mouth but initially no words seemed to form. Lisa could not help but notice that he had the most lusciously full lips, large for a boy and slightly wet. He had that puppy dog look of a young man whose lips were always ever so slightly open. Inviting…

“Umm…good morning Miss….” Ollie started.

“Lisa…please. Miss makes me sound sooo old,” Lisa interrupted with sugary sweetness.

“Umm…,” Ollie stumbled again, “I play for the Southern Football League,” he blurted out. Lisa smiled at him encouragingly. “Umm…and we’ve got a bit of a fundraiser going on for the new season,” he finally got out, “…umm and I’m just wondering if you would like to buy some raffle tickets?” Task accomplished, Ollie relaxed a little, those big brown eyes daring to look at Lisa more directly.

“Oh Ollie I would be delighted,” purred Lisa. “I must confess that I’m a very keen follower of the SFL. I love to watch the guys….err games..” she quickly corrected her deliberate error. “Now in fact I’m almost certain that I watched…saw you last season. Are you playing in the senior league this year perhaps?”

“Ahhh…no. I’m still in the Junior league this year,” said Ollie, ever so slightly bemused by Lisa’s level of observation. “But this will be my last year in the Juniors,” he added as if it was somehow necessary to demonstrate his maturity.

“Lovely!” exclaimed Lisa with genuine enthusiasm. “Well I certainly look forward to following you this season….and next!” she added. “Now….how much are these raffle tickets Ollie?”

“Ummm $2 each or 6 for $10 Miss….err…ah Lisa…”

God how she loved his blushing. And those fingers as he fiddled with the raffle tickets….sooo long and strong. His skin was smooth, his face had certainly never seen a shaver but his physique was all man. He looked back up at her and most certainly registered her attentive stare. Nervously he swept that fop of hair back off his face and as he did so Lisa was blessed with a glimpse of underarm…a truly enticing whisp of hair. She thought she might swoon right there and then.

“Right,” she steadied herself, “well I’m very happy to support the team so I’ll happily buy $100 of tickets.” She was delighted with his predictably excited response.

“Really? Oh my god that’s awesome….really,” he fair bubbled with excitement.

“Absolutely. The club seems to have a terrific family vibe to it,” she added, “and anyway….I do think it’s good that healthy fit young men like you have the opportunity to race around and burn off all that energy.” She smiled sweetly at him once more, her lips parted ever so slightly and the tip of her tongue just visible. “Now,” and she swung the door wide, “come on in while I find my purse.”

She did not give him an opportunity to question the invitation, quickly turning on her heel and walking ahead, conscious that he would be treated to the sight of her ass clad in tight fitting shorts wiggling up the corridor in front of him.

Reaching the kitchen she turned to face him, knowing immediately that she was right. His gaze quickly reverted to her eyes but she knew he feared he’d been caught and that blush swept up his face again. She knew he was ready for the next stage.

“Oh you poor thing,” she said, reaching out to stroke his arm concernedly, “you do look hot. Have you been out there doorknocking all morning? Here….sit at the bench and I’ll get you a cold drink.”

She patted a stool at the end of the bench to show him where to sit. It was all she could do to stop herself from patting his delicious little ass but again she looked him up and down. Was it her imagination or had that bulge actually grown on the trip up the corridor?? She opened the refrigerator and then turned back to face him. Bless him. Perched with one foot on the floor and one on the footrest of the stool his legs were spread wide as young men somehow seem to manage so unselfconsciously and, his little footy shorts riding up high, the bulge of his balls was clearly evident at one side…enticingly framed in stretched tight pale blue undies. It was all she could do not to pounce right then…but she held firm to her strategy. Still, she knew the signs of the hunted, appreciating its fate was upon ka├žak iddaa it, instead of resisting…making the most of it…and Ollie for all his youthful inexperience was at that point.”

“Oh silly me, I was just about to offer you a beer but I don’t suppose that would be….appropriate? Given your age I mean…?” Ollie was possibly a tiny bit too fast to clarify….

“Oh….no that would be great. I’d love a beer I mean.” He stammered slightly. “I mean…no I’m playing in the Juniors because I wasn’t 18 at the beginning of the year. Actually I had my birthday earlier this month so….yeah…I’m legal and everything.” As if to make absolutely sure Lisa appreciated his clarification he added. “Ummm yeah so….yeah a beer would be sick.”

Lisa turned back to the fridge, partly to get Ollie his beer of course, but also because she needed to conceal the grin which she found she could not control, and partly also…in order that she could bend right over, ass in the air in order to reach the bottom shelf….for the beer. It seemed to take quite some time to find and as she turned back to Ollie he appeared distinctly flustered. She passed the beer to him and as he grasped the bottle her other hand encased his.

“Mmmm you have such big strong hands Ollie. I guess they’re good when you’re playing footy.” She looked at him directly. “I’m guessing they’re good for….lots of things…..”

Ollie was at a loss for words. She could see the thoughts running through his brain as if they were projected onto his forehead. Competing emotions, competing expectations, uncertainty….but real hope that every schoolboy’s fantasy was about to become….reality. He lifted the bottle to his lips….those spectacularly luscious lips and again she was treated to a view of that generous sprinkling of pit hair. She noticed his hand shake as he sipped, trying for all the world to appear relaxed….as if he enjoyed a beer with the woman down the street every day. He was hers….she was sure of it.

“Gosh….it’s not just you that’s hot Ollie. Me too,” Lisa said as she peeled off the tight cotton top she was wearing. It wasn’t quite a striptease but it was certainly tantalising. Her full tits bounced in the singlet top she had on underneath, the thin shoulder straps straining to take the weight of her ample bosom, her cleavage at Ollie’s eyelevel as he sat on the stool. Ollie’s beer froze half way to his mouth which hung further open. There was no hiding his stare but he stammered out an attempt at subterfuge.

“Yeah…yeah it’s really hot. Umm….ahem…yeah…umm the beer’s great thanks,” and with a sudden burst of confidence, “what about you…Lisa? Aren’t you having a drink?”

And like the cougar she was, Lisa pounced.

“Well….Ollie….” she drew out each word whilst looking at him overtly seductively. “Well Ollie, I thought I might like a…milk drink,” and she let that sink in for just a few seconds. It was as if Ollie was frozen in time. He had turned slightly away from the bench, his elbows resting on it in a semblance of manly confidence. The beer was gripped in one hand on the bench. His mouth opened as if he was going to speak but no words formed. Lisa continued.

“Yes….Olllie….,” she emphasised each syllable. “Yes Ollie…I really feel in the mood for a milk drink. But you know what?” She looked deep into Ollie’s eyes. Ollie’s brain was feverishly trying to process this but failing utterly.


“Hhhmmm…” she purred, “I like my milk straight from the spout.” And as she said that her hand slid up the inside of Ollie’s hairless thigh. He let out a slight squeak but his legs did what any guy does in such circumstances….they opened wide, inviting her attentions further and instantly her finger tips found the bulge of his balls which she had glimpsed earlier, now more fully revealed. She traced their fullness with her fingers, purring as she went.

Ollie gulped.

With her other finger Lisa traced the length of Ollie’s entrapped erection up the other side of his shorts. “Oh Ollie….you really are a big boy,” she murmured appreciatively. It was true…but Lisa also knew that if there was one thing young guys loved to hear….porn to their little shell like pink ears…it was how big their cocks were….how full of cum their big balls were….how hard they were. A further moan from Ollie in response only reinforced her judgement. Taking his weight on his elbows he lifted his ass off the stool and Lisa, no further encouragement required, peeled his little footy shorts and undies down over his cock and balls, pulling his knees temporarily closed and then down his calves where she left them bunched around his ankles. His knees sprung wide and his cock sprung up fully upright and throbbing against his stomach. Unconsciously Ollie’s spread legs presented his throbbing cock like a gift to Lisa, one she was all too happy to accept!

“Oh fuck….oh fuck….oh……faarckk…” from Ollie.

“Oh ka├žak bahis Ollie!!” Lisa was blown away by his utterly delicious form. Long legs with just a dusting of fine blond hairs led inexorably up to smooth thighs with a gift that would have been impressive on a fully matured man. Lisa had enjoyed more than a few ‘talented’ guys in her time, and truth be told she was something of a size queen, and Ollie would have challenged most of them. With no exaggeration his cock would have been a genuine 8″. It was gently curved and beautifully dimensioned, long and thick though not overly so. It stood straight up, urgent for attention and counter balanced by the most perfect pair of balls she believed she had ever seen. Perched as he was on the edge of the stool, his balls hung loose in their entirely smooth silky sack. They were the size of two ripe plums, heavy and plump and no doubt full of ripe cum just ready to be spent.

“Oh Ollie,” she repeated, “you really ARE a big boy!! Mmmm…I bet you get no complaints about that from the girls…?” And she looked up at him, his face tossed back in a mix of ecstasy and disbelief. “Although….possibly some of them might find it a bit….intimidating..?” she laughed. Ollie looked down at Lisa’s upturned face and blushed some more.

“Umm…well actually I haven’t…ummm…you know….” his voice trailing off.

“What? You haven’t been with a girl??” She looked at him for confirmation and his face said it all. “Oh wow….well Ollie I think maybe it’s you who won the raffle today after all,” she smirked.

Lisa was an expert with young guys. And she knew that the younger and less experienced they were the more hair trigger their cocks were. She knew they didn’t have much time in any case; after all Ollie was supposed to be going door to door selling raffle tickets. But she didn’t want him to cum immediately either so she started with those ripe plums suspended in front of her. First of all, with just the tips of her fingers she kind of raked his golden sack from back to front. Without taking them in her palm just yet she caressed the back of his scrotum feeling how his cum filled balls joggled within, lifting and dropping in response to her attentions. Then she bent forward and opening her mouth wide she plopped just one ball into her warm wet mouth and slurped her tongue around its firm globe. Immediately Ollie lent back further on his elbows and gasped aloud.

“Ohhhh faarrckkkk….” he groaned. And then instantly, “Oh…sorry Mis….Lisa….”

Jesus. Did he just apologise for swearing? Oh my god is this boy/man not the most adorable thing that ever walked the planet??

“Mmmm….” Lisa’s mouth was full. She let go his ball briefly. “Oh Ollie….believe me you have nothing to apologise for!!!

“Ohhhhh…..oh yeah…oh….Lisa…fuck yeah….” and Ollie relaxed into his euphoria fully.

Bending back to her task Lisa determined to get both those big fuckin balls into her mouth at once. For a young guy his balls were not just big but hung really loose. His sack was magnificent and perfect for a major tongue bath. Lisa grasped the base of his sack in her fingers. His plums were tight in the palm of her hand. She licked them expertly, swirling the flat of her tongue around the base of his cock and the sides, eliciting moans of desire from her young partner. And then, opening her mouth as wide as she could she slurped one ball into her mouth and with her fingers she gently but firmly forced the other in as well. Her mouth was completely full but her lips closed as much as possible around the neck of his sack as she breathed gently through her nose.

“Ohhhh fa fucks sake….” Ollie was beside himself with desire….delirium almost. He’d come to sell raffle tickets and in a matter of minutes he was semi naked with his balls in the mouth of a hot chick.

Lisa used just her tongue….the flat of her tongue to slide around Ollie’s swollen balls. They felt amazing in her mouth. Full and smooth. She could sense the urgency of young cum just minutes away from release. There was a subtle saltiness to him….the delicious sweet perspiration of youth. Holding his balls captive Lisa’s hands caressed those gorgeous smooth strong thighs and played with the curve of his tight little butt over the edge of the stool. His massive cock throbbed and bumped against her face. Damn he was big. Lisa’s fingers slid up beneath his footy jumper and found his perfectly ripped teen torso beneath. She was almost overwhelmed by Ollie. He was so fine….so manly and yet so boyish. Smooth with just enough hair where it should be, muscular but not beefy and….oh my god…HUNG!! How his team mates must envy him in the changeroom she thought. Lisa pushed the jumper right up, still with his balls in her mouth she reached above her to caress his tight stomach and chest. He had flat little nipples and as she gave them a quick squeeze he exhaled loudly. Just at that moment Lisa felt a sticky wetness on her forehead. Oh yes….precum…he was leaking….perfect. A low purr…a growl almost escaped her throat as she released his balls with a final lick on the way out of her lips. She sat back on her haunches to survey the scene.

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