The Weekend Pt. 02

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A middle-aged widow opens her mind to life as a Cougar.
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Part 2 of the 5 part series

Updated 06/07/2023
Created 12/22/2014
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Before reading this little adventure, please read The Weekend (Part I) which was originally intended as a stand-alone story and I have changed slightly at the suggestion of several readers in order to extend and complete the tale of our heroine.

There is not a great deal of graphic sexual shenanigans in this absolute figment of my imagination, so if you are looking for a 'stroke' story, please give it a miss if you feel you may be disappointed.

As always. Any similarities in these stories with persons either living or dead are purely coincidental and not intended to cause offence.

The copyright for the following story is owned by the author and it may not be republished without his express permission.

Here's hoping you enjoy,

Oldie

*****

Summer 2008 - June

Chapter 1

"No Emma... No way... It would be like you are my pimp or something."

"What about if I bring James again? You had a great night with him that weekend didn't you?"

"I said NO... That night should never have happened, you know that. You both caught me in a weak moment."

"For fuck's sake mum, you're just being silly. I only offered to help you out that's all."

"Well I don't need your help to find men, so just drop it... Okay?... And stop swearing."

The 22yr old daughter stomped off to her bedroom in frustration, muttering to herself about the stubbornness of the repressed older generation her mother belonged to. She couldn't see any problem with what she had proposed. After all, all she'd done was suggest that she knew some fit young men who would love to fuck her mum if she really wanted to be a sexy Cougar and have the kind of uncomplicated sex- life Emma had herself. She was sure many of her male friends at college would be more than happy to sleep with an incredibly sexy mature woman like her mother. As usual, her embarrassed parent had gone off the deep end. Full of shame-filled denial of her innermost desires and trying to banish any thoughts of what she had willingly allowed to happen to her, her infuriated mother had dismissed her daughter's well-meaning suggestion with an infuriating outburst of moral indignation.

Barbara grimaced as she heard the bedroom door slam. Outwardly, she was visibly annoyed at her daughter's temerity for even suggesting such a thing. How on earth did the young girl think it would be okay for her to mother to have casual sex with boys she hardly knew? Boys who were half her age, perhaps even boys her daughter had slept with herself? Inwardly though, deep inside her previously inhibited psyche, she thrilled at the lurid images flashing through her brain. Images of James' muscular young body as he lay on top of her and pounded his thick penis deep into her loins. Wonderful memories of how he had taken her from behind, his strong hands gripping her soft hips as he thrust himself into her. Yes, Barbara thought to herself, she would love to be taken aggressively like that again - and again, and again. As many times as it took to satisfy her lusts. Yes, she wanted to be fucked, wanted to be used as a sexual goddess. But how? How could she meet those young men without the whole world knowing about it and disapproving?...

* * *

It had been more than six weeks since Barbara had spent that wild, lascivious weekend having sex with her daughter's some-time boyfriend. Six weeks since she had been fucked - not made love to, that had been years. Not since her husband David had been so cruelly taken from her had she known the tenderness of being intimate with the person she loved. She reluctantly admitted to herself that she was grateful for that weekend. Happy now in the knowledge that she could in fact enjoy having sex without any emotional attachment to the person she was sharing her body with. All the inner doubts she had been having were well and truly banished to the back of her mind, leaving her primed for any sexual activity that may become available to her healthy, horny, mature body.

How to meet suitable men though? How to meet unattached young men who weren't the kind of sleaze-balls she'd always imagined would searching for lonely, middle-aged women to have sex with. That was the problem for a single woman of her age who very rarely ventured out socially. Certainly, she never went to any place where there might be a selection of potentially available young studs who were on the prowl for an older woman to ravish. In truth, when she thought about it, she had absolutely no idea where those sort of places may even be located.

Sadly, all of the possible partners her friends had introduced her to were not in the least bit suitable for participation in the kind of sexual exploits she had in mind. Yes, some of them had been pleasant enough to talk to, but not one of them had stirred her loins as young James had. The hard body of an athlete; the stamina and enthusiasm only a man of his tender years could possess; the penis that seemed to be permanently erect whenever she needed it. All those qualities had, she had to grudgingly admit, raised her expectations and completely ruined her for the sort of genteel, steady lovemaking on offer from men of her own age. Emma and James had indeed coined the phrase that identified what she wanted to become. Cougar - an older woman who sought out young men for the sole purpose of sexual fun and satisfaction - that was what she wanted, no, that is what she needed to be...

Having firmly rejected Emma's outrageous suggestion of bringing friends from college back with her whenever she came to stay, Barbara was in a quandary. She wanted to meet someone, but knew she wouldn't feel safe going into a bar or a club alone. She didn't have any 'single' girlfriends to go out with either, all her female friends were married and she wouldn't feel right asking any of them to go with her when she went looking for a man. Consequently then, her chances of meeting a young man face to face would more or less be left to luck, hoping a fit young Lothario would be tempted enough to approach her whilst she was out and about shopping or whatever - something that seemed to happen frequently in the trashy romantic novels she loved to read, but undoubtedly hardly ever happened in real life. Fortunately, despite all Barbara's misgivings and the two diverse women's disagreements, her daughter did eventually come to her rescue with what seemed to be a reasonable suggestion.

Emma had been reading several women's magazines searching for ideas on how single and lonely mature women could meet men. They all seemed to be of the same opinion - the most convenient and frequently successful approach to meeting someone for a shy or busy woman, was on one of the many internet dating sites that had sprung up over the last few years. The problem was, her mother hated computers. She'd never had one, very rarely used one, and certainly didn't trust them. Reluctantly then, one Monday afternoon in May, an eager, but strangely nervous Barbara found herself in a branch of a major electronics retailer being patronised by a spotty-faced, greasy-haired arrogant young boy who was making little effort to disguise his contempt of all people above the age of 16. Despite the condescending attitude of the extremely irritating and impatient young man, she managed to purchase a top of the range Dell laptop and, with it tucked under her arm, almost ran out of the store before she completely lost it and slapped the cocky little prick across his acne-riddled chops.

The day after she bought the laptop, Barbara had eagerly waited for her appointment with the broadband company recommended by Gerald. She'd fortunately calmed down overnight, admittedly with the help of several large glasses of white wine, when an engineer arrived to install a complete wireless system in her apartment. The type of system any modern, young single woman needed - according that is, to what the extremely competent telephone salesperson told the mature but gullible Barbara - one that would enable her to connect to the internet wherever she was in the flat. The helpful young engineer, after installing all the relevant cabling and equipment, had showed her how to 'login' and how to set up a security password so that only she would be able to use the network, explaining everything to her thoroughly and completely earning the large tip she insisted he take.

Almost inevitably of course, left to her own devices, the totally bemused and inexperienced new user didn't take long to completely cock everything up, locking herself out of the system and preventing herself, or anyone else for that matter, from connecting to the internet.

At a loss as to what to do, Barbara tried ringing her daughter, only to find that the young girl had her mobile phone switched off and was unavailable to help. Impatient to begin exploring the 'net', she tried a couple of friends, both of who were unable to help her, being as they were around the same age as her and had about the same knowledge she had when it came to computers. Eventually, she came across her architect friend Gerald's name in her phone contact list. As a habitual computer user through his work, her only single, male friend was certain he would be able to get her going again and told her he would be round in about half an hour, telling her to make sure she had a bottle of good Chablis chilling in the fridge.

* * *

As promised, Gerald arrived 35 minutes later and immediately began gently ribbing her about her apparent 'elderly person' computer problems, pointing out that maybe, just maybe, she might have been better reading the instruction booklet before attempting to use the laptop. Amidst much good-humoured banter back and forth, he quickly re-booted the system and logged her onto the internet once again.

"And what made you finally decide to enter the twenty-first century then?" Gerald laughingly enquired, leaning back on the comfortable sofa and sipping at the glass of cold wine he'd been offered when he arrived.

"Oh, you know... I thought I should get up to date and join the rest of the world. Although if I'd have known I'd have to put up with you extracting the urine like that, I wouldn't have bothered."

The two good friends chatted happily together, finishing the wine and eating the Chinese takeaway they'd decided to order when they discovered neither of them had had dinner. Slightly tipsy - she'd drunk far more wine than her friend, who'd insisted he had to drive back home after he'd sorted her out - Barbara found herself telling him all about her lecherous weekend with her daughter's boyfriend, eventually confessing that the real reason she wanted the computer was to go online and find herself some more young men to have wild, passionate sex with.

"Bloody hell Barb... You little slut, you... I had no idea you were into boys young enough to be your son... You naughty old slapper." Gerald laughed, pushing her gently before hugging her to him in a warm embrace.

"Oh please don't... I know I'm a dirty old trollop, you don't have to tell me... I just happened to find it exciting, being shagged like that... So hard... You know, so energetically."

"Oh I do know sweetheart. I love younger men myself... Their young firm bodies and all that stamina... So damned hard to resist."

"Yes, but you're just an old perve." She teased, "But I do love you dearly..." Their laughter filled the room as the good friends collapsed on the sofa in a fit of giggling, hugging and crushing one another in a warm display of mutual affection.

A short while later, Barbara was leant against her gay friend's chest, almost asleep due to effect of the wine and his hand gently caressing the back of her neck. "Where were you going to look? You know... On the net. What sites were you going to?" Gerald queried, extracting himself from her embrace and re-opening the laptop on the coffee table in front of them.

"I've got no idea, Emma just read in some magazine or other that the 'net' was the best place to find dates nowadays, so I thought I'd give it a go."

"Oh, Okay... Would you like me to suggest some suitable sites?"

Barbara sat up and gazed quizzically into his eyes, her eyebrow raised in a silent question.

"What?... So I use those sort of sites myself... Okay?" He laughed, mock indignation in his voice.

"But what would I want with a gay man?... I don't want ANYTHING up my bottom, thank you very much... Well not a gay man's thingy anyway."

"Don't knock it until you try it, you naughty old bigot. You never know what you might enjoy until you give it a go." Gerald mocked, dragging her slim body over his knees and slapping her backside hard enough to sting and send warm sexy feelings flashing through her loins.

"GERALD... You big, bloody tease... Stop it... God, it's such a shame you're gay, you kinky old fart. We could really make some happy music together if we ever did the dirty deed." She chuckled, all remaining semblance of her dignity disappearing as she rolled away from his grasp and rested on her hands and knees for a breathless second before inelegantly attempting to rise from the floor.

"In your dreams girl, in your dreams." He laughed, logging onto the internet as she clumsily pulled herself from the floor and sat next to him again, "There are dating sites that have all sorts of people on them. Men and women looking for anything you could think of. Gay, straight, bi... Anything you might fancy really."

"Really?... Wow! I had no idea... I absolutely must get out more, as my daughter keeps telling me."

"I thought that was the idea." Gerald laughed, earning himself a gentle punch in the ribs.

* * *

The two unfortunately sexually-incompatible friends soon discovered they actually had similar tastes when it came to prospective sex-partners. Both of them liked young, fit men; muscular and good-looking with a nice smile. To Barbara's amusement, they also both agreed that they preferred a good-sized, nothing out-of-the-ordinary, normal-looking, penis. Of course, their conversation rapidly became competitive - each of them trying to beat the other when it came to putting 'dibs' onto any particularly attractive specimen of nude masculinity.

Barbara had quickly realised during their exploration of the internet, just how naive and innocent she had been previously. She'd ultimately concluded, the more and more kinky, even sometimes bizarre, details of other peoples sex-lives they'd uncovered, that all her naughty dreams, all the sexy fantasies she and her late husband David had shared, were nowhere near as perverted as she had once thought. Feeling her sex moisten as they looked at the advertisements, many containing explicit nude photographs, she'd finally had to admit to herself that she found all this extremely exciting.

Browsing through the provocative messages with Gerald, she'd seen propositions and offers to participate in things that absolutely amazed her. She'd been especially shocked by some of the invitations from the couples on there. - "How on earth can they supposedly love each other and yet want to have kinky sex with other people?" She'd asked of Gerald - Even just a few months ago, Barbara would have been appalled at such suggestions. Yes, she'd had fantasies before, dreams of sharing her body with David and another man. But that's all they were, just fantasies to be kept private and used to enhance their already deeply pleasurable love-life. After what she'd seen in those advertisements though, she'd soon accepted that her own fantasies had been mild in comparison to some of the desires expressed by people on those websites. Yes, she admitted restlessly, those audacious, hopeful sexual-playmates were kinky; some of them even downright filthy; but as she'd excitedly realised when she felt her sex heating up and moistening, she found many of them very arousing and tempting.

Eventually, Gerald left her apartment to go to his own home, reluctantly declining her offer of the use of her spare bedroom as he had to be on a building site early the following morning. Barbara had then drunkenly fallen into her bed and, amidst dreams of hard six-packs and large, throbbing penises, had brought herself to two particularly satisfying orgasms using her fingers and then her favourite 'Rampant Rabbit' vibrator...

* * *

The following morning, a slightly hungover Barbara sat nursing her second mug of black coffee of the day. Her new laptop lay open in front of her on the kitchen table as she studied the short list of websites Gerald had left for her to investigate. She chuckled to herself, remembering how he'd tried to show her how to look at them without committing herself to any form of membership - tried and failed miserably, their conversation rapidly sinking to a bawdy level of lewdness and giggling as they compared some of the people who were advertising for participants in all manner of degenerate sexual activities.

Many confused thoughts were running through her mind as she stared at the blank screen, unsure of whether to continue with her explorations or not as she turned the list over and over in her hands.. Could she actually do this?... Is this what she genuinely wanted?... Could she REALLY meet a perfect stranger, knowing that, probably within the hour, she would be having vigorous, no-strings-attached sex with him?

Finally, giggling nervously to herself, she logged onto the internet and began searching the websites on Gerald's list, "C'mon girl... You can do this. Go out and get yourself a good seeing to. You know you want to." she chastised herself, chuckling nervously as she logged onto the first site on the list, "Just put it out there and go get yourself FUCKED..."

Chapter 2

Over the next couple of weeks, Barbara investigated the full list of sites given to her by Gerald. On several occasions her friend came round to her apartment and helped her search for what she was looking for. Occasions which invariably ended up with them both in hysterics, much the worse for wear with drink due to amount of wine they'd consumed, but also most definitely horny because of the content of their searches. Barbara was astonished at the blatant exhibitionism of many of the people who's advertisements they looked at. Lots of men, quite a few women, and many, many couples searching for extra excitement in their otherwise mundane lives, had placed very explicit photos of themselves. Men had pictures of their erect penises, women had their legs spread showing their wide open genitals, and nearly every couple had photos of them both together in various stages of undress.

Barbara gasped loudly at seeing a particularly explicit image of an easy-recognisable, attractive, middle-aged couple having anal sex. "My God!... I could never do that. Show myself to the whole world like that I mean. Bloody hell, I'd be petrified anyone who knows me would see them... I mean... They're shameless, for fuck's sake..."

"Me too. I never put public photos on. I only send them some if they ask for them privately and have some of their own... Although... If you do need someone to take photos of you like that, I do have a really good camera..."

"You really are an old pervert." Barbara laughed, missing when attempting to slap her cheeky friend around the ear as he ducked away from her reach before grabbing her and hugging her tightly as they collapsed giggling like a pair of school-kids once again.

"Seriously though Barb. Are you going to sign up for membership of one of the sites then?"