The Challenge Pt. 01 – Exhibitionist & Voyeur – Free Sex Story

1 Star2 Stars3 Stars4 Stars5 Stars
Loading...


A slow-burn story of a woman rediscovering herself through taking on a series of dares. This is a standalone story…but there will be dirty dares and a budding Romance to come in at least one follow-on story.

Written in British English. Please take the time to let me know what you think.

The Challenge

The crisp white wine that had been calling her name all afternoon fizzed on Rachel’s tongue as she gulped a mouthful down and sank into her favourite squashy chair in the conservatory, reaching for her iPad. The browser window was still open on the front page of the dating site she’d visited on a whim the other day. She closed it and caught up with the day’s showbiz gossip, taking another sip and another, until her glass was empty and the stresses of the week were slowly starting to fade away.

She padded into the kitchen, topping up her wine, putting a pizza into the oven and making a small side salad, which would obviously make the dinner more healthy. Walking to the bottom of the stairs, she cocked her head, and listened. Silence. Nope, Robbie was definitely out.

She fired a text off to him, letting him know she was back from work and asking if he’d be home that night. It didn’t matter either way, and he was certainly old enough to look after himself at 21, but if she knew he wouldn’t be back, she wouldn’t lie awake later waiting for him to get in.

Sitting back in her chair, she surveyed the garden, the rose bush that needed pruning before summer arrived catching her eye. Friday night and no plans for the whole weekend. She wasn’t sure whether to be thrilled or horrified. Her 21-year-old self would have been horrified; her 47-year-old self was quite content. Well, largely content, if she ignored that nagging feeling at the back of her mind that her lack of social life was slowly chipping away at her overall confidence. Maybe she should get ‘out there’ somehow.

She grabbed the iPad and typed in the name of the dating site again. Wasn’t everyone on Tinder these days? But the thought of seeing her son’s friends, or god forbid, her son, on there, was enough reason to steer clear. But where did the not-ancient-but-not-young people go?

She narrowed her search criteria to men within 20 miles and clicked ‘Find Love‘, mock-heaving at the cheesiness of it all.

Nope. Nope. Nope. Nope. The blare of the oven timer saved her from the horrors of the profiles in front of her and she discarded the tablet in favour of food.

Returning with plate and fork in hand, she thought more about what she wanted. Maybe a more activity based friendship group would be more suitable? Something where they’d walk up a mountain or go for a pub meal. Something with a physical challenge. She googled ‘dating activity challenge’. Oh no, that was a whole heap of date night suggestions for couples. She was about to close the browser when ‘The Challenge: dare you take the date?‘ caught her eye.

A black screen appeared, red writing declaring this was an Adult-orientated dare-based dating site not suitable for under 18s or for those of a sensitive nature. Am I of a sensitive nature? Thinking back to her escapades in her early 20s, before she’d met Robbie’s dad, she grinned. Definitely not. But her 40-something self? Less adventurous and a lot less sure of herself.

She clicked ‘Enter’ anyway. To hell with it.

She joined and purchased a month’s subscription, then a questionnaire popped up. Not the usual ‘what would your ideal date be?’ or ‘what are you looking for in your ideal partner?’ shite, but a bewildering array of questions she had to answer ‘yes’ or ‘no’ and ‘want to/want to again’ or ‘don’t want to/never again’ before she could go any further.

‘Have you orgasmed in public?’

‘If you gave explicit prior consent, can your partner start to have Sex with you before you wake up?’

‘Have you had a three-or-more-some?’

‘Have you walked around the supermarket with a butt plug in?’

And so on.

Another glass of wine was needed to answer these, but Rachel threw herself into the challenge, surprising herself with how much she had done or would be happy to do. Not that she had the means or motivation to actually carry most of these scenarios out, but her thighs were clenching, her knickers getting wet and her nipples aching by the end of thinking through her answers. She’d certainly be thinking about these in a bit when she went to bed.

Her finger hovered over the ‘submit’ button, but refused to press down. No, she didn’t need to do this. The whole idea was ridiculous. She was a divorced woman, in charge of a team at work, capable of presenting to a packed conference room. She didn’t need to rely on a hyped-up dating site to find a partner. She just needed to get out of the bloody house.

But that wasn’t strictly true, was it? She’d spent the last networking event hiding at the back of the room, spending 10 minutes at a time in the toilets to pass the evening, and making small-talk with the people either side of her at dinner. She didn’t actually do anything or actively start any conversations, just sat passively letting the event wash over her.

Somehow, somewhere along the road, she’d stopped taking control, stopped influencing what happened around her, stopped living. This morning’s meeting popped into her head, the board talking about an issue that she was working on. She’d sat politely, waiting for the opportunity to speak, but it never came, and her weasel manager piped up to say his team had recognised the issue and he was working on it with them. She’d felt the eyes of her colleague James, boring into her, encouraging her to speak, but she’d felt paralysed, unsure of when to break the flow of conversation around her without seeming rude. In the end, James had intervened, saying it was Rachel who had the solution and she’d meekly followed his lead to explain what she was doing.

When had she lost her fucking voice? How had that happened to her?

She sat up straight, a prickle of awareness sweeping over her at how invisible she’d become. From the original party-girl, to mum, to…nothing.

Fuck it.

Her finger clicked ‘Submit’ before her mind could shout out ‘no’. The on-screen text told her the algorithms were matching her level of daring with available darers in her region of England, and to start thinking about what her three dares would be. She wasn’t actually going to do any of the dares, so none of this mattered. She just wanted a bit more content for the spank bank, because maybe thinking more confidently would lead to her acting more confidently. Fake it til you make it, baby!

The screen refreshed, stealing her attention, and nine boxes appeared. Her ‘dare-matches’. No profile pictures or details, just a private, public and personal dare for each box with an ‘accept’ button.

She glanced over them. ‘Flash your tits in public’, ‘show me your arse’, ‘stick a cucumber up your Pussy‘…what the fuck? She lost interest and screwed up her face. Nah, this really was a mistake. She closed the browser, shut the iPad and moved into the living room to put the TV on.

***

It wasn’t until she was lying in bed later that she allowed her mind to drift back to The Challenge site. She’d only scanned the dares and none of them had appealed, all being too base – tits and arse and nothing else. But something about the thought of getting naked outside had hooked into her brain. She pulled her knickers off and discarded them, getting up to shut her bedroom door and pulling her cotton nightie off. She didn’t want Robbie suddenly appearing in the doorway to chat to her, even though his text had said he wouldn’t be back until tomorrow.

She lay back down, bunching the duvet to the side of her in case a quick cover up was needed and let her fingers squeeze her left breast, then travelled down over her belly, briefly squeezing the roll of fat to check it hadn’t magically disappeared, then onwards, running her fingers up and down her few-days old shaved pubic hair. It needed doing again, but she quite liked the stabby feel of the stubble against the pad of her finger, enjoying the scraping noise it made.

Down between her legs, deliberately missing her clit, just to tease herself, along her outer lips, sweeping round and back again, then down the middle of her slit, smirking at the river of wetness. No lube needed here.

She sucked her finger clean and twisted sideways, reaching down and into the drawer under her bed, her fingers grasping the smooth rubber of her rose and bringing it up to view. Hopefully it had enough charge, not that it would take her long. She switched it on and moved it to her favourite setting, then positioned it on her clit. The sucking sensation made her lift her hips and groan, her groin instantly trembling.

She pictured being outside, naked, the breeze on her skin, her nipples tightening, someone there, watching but not participating. The shadowy figure was seated, naked as well, stroking his cock. She was making him hard. She was responsible for putting on a show that would make him come. She had the power over his Orgasm!

Her pressure built and she pushed the vibrating rose down harder. He stroked his cock harder in response, and in her vision, she lifted one foot, which was now fishnet-stockinged and clad in a high-heel, and slammed it down onto the edge of his chair between his legs. He sucked in a breath nervously at how close she’d been to catching his balls and shifted in his seat, then tilted his head sideways to peer at her Pussy now open to his gaze.

Real-her and dream-her hurtled towards their release, the rose buzzing and sucking relentlessly, and she slapped down hard on her right tit, the crack of pain travelling from her nipple to her clit. The Orgasm exploded across her entire body and she raised up onto her tiptoes, thrusting her groin upwards.

“Arghhhhhhhhhhhhhh!” she shouted out, grunting as she bore down through clenched teeth and let the sound exhale. Her heart beat a frantic pounding in her chest and a multitude of bright lights fizzed across her eyes.

She chuckled to herself, noting yet again, that no man had ever been able to come close what that little red toy was able to do. Really, did she need a dirty, smelly man messing up her life when she had this? She grabbed the wet wipes and cleaned up, wiping the rose down and putting it on charge for ten minutes, ready for next time, then grabbed her mug of tea. Yep, perfect drinking temperature now that that was done.

***

It was mid-morning on Saturday before Rachel was able to sit down with a custard cream and pick her iPad up.

She’d been telling herself all morning that she was going to logon and cancel her account to that stupid website, and she called up the page with every intention of doing so. A reminder flashed up to set her dares and she paused for a second, thinking what they would be. She didn’t want endless cock pics, but what else would she ask for? She closed the pop-up and looked at her nine boxes again, purely for research about the expected level of requests.

Show me your tits, show me your Pussy, tits and Pussy, oh, a tits and arse request, and back to tits and Pussy. The same requests to see the same body parts made over and over. Come on, guys, you can do better than this.

‘Do something in public that no-one else can see which turns you on but scares you.’ Oh. OH! Wow, finally something different. She clicked on the username for ‘PeepingTom’.

Private dare – PeepingTom dares you to: Show me what you use to masturbate with. Accept?

Public dare – PeepingTom dares you to: Do something in public that no-one else can see which turns you on but scares you. Accept?

Personal dare – PeepingTom dares you to: Show me what you think is your worst feature, the one you hide from everyone…and I’ll tell you what I Love about it. Accept?

Oh, that was easy for the private dare, Rachel knew straight away she’d take a picture of her rose and her fingers. Personal dare, well, that’d be my single roll of belly fat that never seems to go, even when I bother to diet, and the stretch marks from being pregnant with Robbie. Public dare…? Her last fantasy popped into her mind, heels and fishnet stockings were not her usual attire by any means, being stuck in mum-mode for too long. She wasn’t about to go walking around town with nothing else on, but if she wore her long black skirt, no-one would know, and if she sat on the bus by the window and carefully positioned herself with crossed legs, she could pull the skirt up, get a snap of the garter clips. Job’s a good ‘un. Sorted. Or was that too boring? What would other girls be doing? A damn sight more than her, probably. And they’d be younger, and prettier. And thinner. And…stop!

She could maybe go out with no knickers on, but that was it. Nothing more daring than that. It’d have to be enough. And if he didn’t think it was enough, old Mr PeepingTom, then he was a Sex-obsessed seedy twat with no idea of how to keep a woman if he was lucky enough to get one. She sat up straight and nodded. Amazon proved to be her friend, just sneaking into the same day delivery availability for fishnets, a garter belt, and black patent high-heels. She decided to dye her hair with the pack she’d had on the side for three weeks — she’d do it this afternoon and get those grey hairs covered up, not that she was going to show her face in any of her photos but a frisson of excitement invigorating her.

She shook her head at herself with a grin, she’d gone from planning to cancel her account, to maybe wearing fishnets, to considering going out with no underwear on, all in the space of 20 minutes or so.

She clicked on ‘accept’ for PeepingTom’s private dare, but the pop-up message reminded her she needed to submit her dares first. Hmmm. She didn’t want the focus of all of them to be overtly sexual. Yes, this was a dating site, but she wanted more than a random hook-up. Whoever she met with would need to have more about him than whatever he had between his legs and be able to sustain a conversation in a bar or restaurant at least.

She opened the notes app and worked her way through the options, like she’d tackle a problem at work, until she had them drafted and quickly typed them into the website.

Private dare — you dare your matches to: Describe your favourite fantasy.

Public dare – you dare your matches to: Do a random act of kindness (non-sexual).

Personal dare – you dare your matches to: Tell me which fairytale character you are most like and why.

She looked at them. Were they okay? The private dare would reveal…well, she wasn’t quite sure what, but she’d like to read something different, not just a Porn replay of a young, skinny, vacant-looking girl getting railed in the arse by an oiled-up, six-packed, mean-looking man telling her what a slut she was. No thanks. The public dare would weed out those just looking for Sex because they probably wouldn’t bother going to that extent, and the personal dare, well, if they didn’t have a sense of humour then this wasn’t going anywhere. She had a feeling her and PeepingTom might be the oddities in a sea of tit, Pussy, arse and cock requests.

She submitted her dares and the screen took her to her account page. She’d picked a site-generated username when she’d joined, but if she was going to do this, she wanted to do it properly. An idea flashed into her mind, and she updated her name to LadyGodiva, choosing the female counterpart to the PeepingTom myth, not that she had any plans to ride the streets of Coventry naked just yet.

Rachel returned to her home page and clicked on ‘accept’ for PeepingTom’s dares. A clock started counting down next to his username. She now had 24 hours to complete his challenges. Shit, she hadn’t realised it was timed!

The door slammed shut, making her jump, and she closed the iPad guilty. Robbie loomed in view and she stood up to greet him. “Hi Love, you okay?”

“Yeah. Going back to bed. Hey, me and Scott are gonna get a flat together, we decided last night, so I’ll be out of your hair soon enough.” He leaned down to kiss the top of her head and turned to walk through the kitchen, grabbing a pack of crisps from the cupboard on the way.

“Oh good, I can halve my food bill then,” Rachel choked on the words, barely able to get them out at the thought of her only child not being here anymore. “And since when has Scottie been ‘Scott’?”

“Nah, I’ll still come round and take what I want. And yeah, it’s ‘Rob’ and ‘Scott’ from now on. Less babyish when we’re picking girls up.” Her son’s 6ft frame lumbered out of view and the sound of his feet thundering up the stairs filled her head.

“Okay,” she whispered to herself, wrapping her arms around her torso and rubbing her arms, back to feeling more lost than ever.

***

The next morning, Rachel dressed for her dare. She had originally thought a long black skirt, but the thought of no underwear at all had been playing on her mind all night, her body alert and wanting it. She chose an olive green maxi dress, fingers fumbling to pull on the fishnet stockings and to do up each clasp from the garter belt. It took a few times to get the material level all the way around, but she strapped on the new high heels and stood, hands on hips, appraising her new look in the mirror.

Her legs looked good. Her soft belly looked…actually pretty damn good with the front of the garter belt holding it in place and covering up the excess mum-tum and stretch marks. Hips defined by the belt too. She looked alright! She had a strapless bra at the ready, her full breasts needing one really. Could she go out without one? She debated it, but it felt too much for this first time. Maybe next time. She put the bra on then brushed her fingers across her exposed Pussy, the skin soft and hair-Free after her pamper session last night, before pulling her dress on.

Smoothing her now auburn-coloured hair without so-much-as-a-hint of grey thanks to a bunch of chemicals, applying a dash of mascara and eye liner to make her green eyes stand out, a swipe of pink lip gloss, she checked herself over and nodded once. She was done.

She’d checked the bus times from her house into the park in the centre of town and she was on track for the one in five minutes. The nerves were jangling now. Can I really do this? Go out in broad daylight, with no knickers on, without even a drink for Dutch courage? What if the bus knocks me over and I get took to hospital? Shit. Why am I doing this?

She knew why. She knew she felt more alive than she had in such a long time. Yes it was because of the dare, but she was the one doing it. She need never show anyone the photos if she changed her mind, but she would always know she’d done it. The exhilaration was thrilling, pulsing through her clit and making her ache to come. She checked the time, four minutes. Could she knock a quick one out? She put her right leg up onto the bed and watched herself in the mirror, hitching the dress up and exposing her Pussy, pressing directly on her clit, slowly at first and then building the pace. She imagined knowing she was walking around naked under her dress and someone found her — no, if she’d agreed that PeepingTom — would find her, and push her against a tree, stick his hand up her dress, and touch her bare skin. He’d-

She checked her phone, shit, she was out of time and needed to go.

Pulling her jacket on, Rachel grabbed her handbag and locked the door behind her, walking the short distance to the bus stop. An elderly gentleman was there and she greeted him with a bright, “Hello.”

error: Content is protected due to Copyright law !