The Challenge Pt. 01 by BritStories,BritStories

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.

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