A slow-burn story of a woman rediscovering herself through taking on a series of dares.

Please read The Challenge Pt. 01 if you want more in-depth context, but this follow-on story can be read on its own.

What you’ll need to know: Rachel, 47, has lost herself following motherhood, divorce, and life in general. She signed up to The Challenge dating site under the name LadyGodiva, where potential matches set dares for each other. She accepted the challenges from PeepingTom, increasing her confidence with each completed activity, only to find out he’s her colleague, James. They agree to continue with the dares…

Written in British English. Like the story or got any suggestions to make? Please take the time to vote or comment to let me know what you think.

The Challenge Pt. 02

Rachel waited until all of her colleagues vacated the meeting room, then cleared the table of discarded coffee cups. She absentmindedly registered the whoosh and click of the door opening and shutting before a solid warmth pressed up against her back; two large hands appearing in her vision, cupping her breasts and pulling her into him.

“I’ve been watching you.”

It was their phrase. The words they decided he’d use to let her know it was him when they were playing out a dare, even if she already knew or suspected it. The words that would calm any spike of unease without taking either of them out of the moment, along with ‘Red’ to immediately stop play, no questions asked.

A shiver of recognition shot through her body, excitement at his first time of using them and what he’d do next, but she underplayed her reaction with a scoff, “Took your time.”

He grunted his agreement in her ear, the hands thumbing a nipple each through her clothing, then travelling up, one snaking through her hair and yanking her head back, the other coming up to grasp her exposed throat. “Had stuff to do, beautiful. Like-“

His words were cut off by laughter carrying down the corridor as the next lot of colleagues approached the room for their meeting. Her blouse was grabbed and pulled out at the front, her head pushed to the side as the body behind her peered over her shoulder then stepped away, leaving her craving the return of his warmth.

She gathered the papers and her laptop, clutching them to her chest, then walking out, thanking the influx of people as they parted and held the door open for her. Her heart thudded in her chest, her throat constricting and her mouth dry, wondering what would have happened if they’d arrived a few minutes later and entered the room, assuming it to be empty.

What would they have seen? She pictured her body arched against his, maybe his hand down the waistband of her skirt, her head thrown back against his shoulder as they writhed together…her moans masking the noise of their approach…the look of shock and the gasps of her colleagues as she orgasmed in front of them…

A cup of fresh cold water sat in the centre of her desk and she smiled as she set her things down then drank thirstily.

Her phone pinged. A notification from The Challenge…PeepingTom had replied to her dare to find out what colour bra she was wearing: Bright pink. Shame I didn’t get to check if your nipples matched.

Rachel’s lips quirked, but her colleague sat back down at the desk next to her so she schooled her professional face into place, hoping her cheeks weren’t as flushed as she suspected they were.

“Why’s James getting you drinks?” asked Mandy slyly, looking up at her from those ridiculous false eyelashes. “Are you two…?”

“Don’t be daft,” snapped Rachel. Softening her voice, she clarified, “We’re friends. I needed water and had my hands full so he got me some. That’s all.”

Mandy’s expression told her she didn’t believe Rachel any more than Rachel believed her own words, but an incoming call on her laptop provided a welcome end to the conversation.

***

Ping! The water sloshed against the side of the bath as Rachel sat up to dry her hand and reach for the iPad, her heart speeding up and a smile already on her lips.

Time challenge! As soon as you accept, you have 15 minutes to complete…PeepingTom dares you to: Go to the shops without that pink bra on. Accept?

She wasn’t ready to accept just yet, so ignored the options and sank back into the bath, trailing her hand down her stomach, along her leg, then back up her inner thigh. She circled her clit, but shied away from direct contact to prolong her arousal, humming ‘Don’t Look Back In Anger’ by Oasis as she finished off soaping her legs.

It’d been three days since she discovered James was PeepingTom, and there was something liberating about talking to his online persona at night, swapping fantasies and stories, and then meeting him for lunch at work, swapping knowing glances and smirks, with no worries about judgement and the odd fun dare where they could get away with it. She’d never imagined she’d like him as much as she did, but knew that was more a reflection on her than him. But she’d leave him on the edge a little right now, enjoying the thought of him waiting somewhere, pacing up and down in his kitchen perhaps, checking his phone every few minutes to see if she’d accepted, cursing when he saw she still hadn’t.

Half an hour later and she was ready to leave the house, sans bright pink bra. Clicking accept, she stepped out and pulled the front door shut behind her. The Spring temperature had cooled since she came home from work and the thin mint green blouse did little to hide the swelling of her nipples, already erect in the evening air. Luckily her jacket pulled across her chest maintained her decency as she walked down the street and waved to Mrs Thompson sat in her window, but the weight of the denim rubbed the blouse material against her puckered tips somewhat painfully with each step.

The skinny jeans and new wedge heel boots were working wonders for her legs and arse as she checked out her reflection in the car doors, liking what she saw of herself after years of avoiding mirrors. Jamming her hands into the jacket pockets, she thrust her fists forwards and outwards to Free her breasts to sway and jiggle as they wished.

Oh, yes! I like this!

She peered down at herself, watching the movement under the blouse, fascinated, but the awareness of someone coming towards her made her cover herself back up. As the stranger passed her, she opened her jacket, revealing her curves and poking-out-nipples under her top if only he would look over towards her…but he didn’t. How disappointing!

Another guy, maybe 10 years younger than her, crossed the road heading towards her. Can I do it? The need to be seen was powerful, calling out to her in some deep way she’d buried for so long. He came into her eyeline and she pulled her elbows back, in slow motion it seemed, thrusting her chest forwards, her head held high.

He surely couldn’t fail to notice the bouncing flesh under her blouse, and sure enough, his eyes were fixed on her tits as she strode past him with a huge grin on her face.

Yes!

She turned off the main street to follow the path between two houses. The alleyway was deserted but she checked nervously behind her and in front. All clear and she wasn’t in view from any of the houses. She pulled her jacket back and took a photo of her tits, nipples visible through her thin blouse. Then another, looking down her top. Next, feeling daring, she lifted the hem of her blouse and revealed both breasts, snapping them quickly then lowering the top back down.

Her heart was pounding in her chest, but she felt freer than she had done since mum-life took over. The ache between her legs reminded her she was alive and she wished PeepingTom was here to fuck her now, to ram his cock up into the pool of need, to see her come undone outside. Not that she actually would, but just the thought was enough to turn her on.

She surreptitiously swiped her finger between her legs, along the outside seam of her jeans, teasing herself. Grabbing the zip, she pulled roughly, a small cry escaping her lips as the jeans jerked against her clit, wanting more, needing more; but a woman came into view at the top of the path. Bollocks. She pulled her jacket back around her, disappointed but flooded with the reality of her situation. She chucked nervously at herself, feeling a bit silly now the moment had passed. What if a neighbour saw her acting like that? She’d be the talk of the street. She continued on her journey, uploading the photos to PeepingTom as she went.

A bottle of wine and a chocolate bar purchased, she returned back down the alleyway, pulling her phone out and checking her emails to distract herself.

Her ears pricked at a noise behind her, but two hands grabbed her upper arms and bundled her off the path, pushing her up against a brick wall, thick arms cradling her head against the impact, before she could react. Her bag slithered down to the ground and the unease skittered across her body as she bucked her hips against the pressure on her arse, taking a breath to scream-

“I’ve been watching you.”

The sound died on her lips at his words and her legs trembled as she pushed back into his body, the relief leaving her unsteady. PeepingTom. He’s here! But how did he find me?

A hand crept around her waist, up under her blouse and gently kneaded her left breast. The Horny Rachel instantly sprang back to life inside Sensible Rachel, shoving any internal protests aside. Cool lips pressed against the back of her neck, and she arched her neck, preening for him. He pulled away slightly and she was spun round to face her online-darer. She focused on his eyes, which were staring intently at her, and she raised her knee between his legs to push none-too-gently against his groin. He clamped his thighs shut, trapping her elevated leg, then looked left and right before grabbing the material of her blouse and lifting it up to under her chin.

Rachel gasped, wanting it and hating it. She didn’t really want him to expose her like this! Did she? It was just a fantasy, wasn’t it? Was it a ‘Red’ situation? Her morals teetered on the edge…nah. She looked in either direction nervously and half-heartedly struggled against him, but he held her firm, stepping back to stretch his arm out, his hand on her chest, her blouse bunched up and her tits on display to any passers-by.

“Please,” she whined, not sure what she was asking for.

His eyes left her face to travel down her body slowly, like he was feasting on the sight of her breasts in the fading light. He reached his Free hand up and cupped her breast, shaking it in his palm then letting it bounce back into place, repeating on the other side. The weight of her tits moving freely was a delicious torture and she moaned, sagging against his hand holding her in place.

“So. Fucking. Sexy,” he murmured in awe. He pulled his phone out, holding it up questioningly.

She nodded, biting her lip. “No face though, like we agreed.”

He smiled and darted forwards to kiss her briefly, shooting fire from where their lips brushed to down through her body, then pulled back to take shot after shot of her tits bared to the night.

The cold was seeping in and Rachel’s body starting shivering in protest.

“Sorry,” James grinned, pulling her top down and adjusting her jacket. “I got carried away. Can I walk you back?”

She laughed nervously at the change in pace as she bent to pick her bag up; the eroticism of forced exposure clearly a definite turn on for her, given how wet she was pretty sure her knickers were, but struggling to adjust to the man she knew as her work colleague now in front of her. She took James’s proffered hand and tucked herself into his side as they walked. “How did you find me?” she asked, her mind switching back into practical mode.

“I’d checked your nearest shops on Google Maps and worked out your most likely route. Bit of pot luck really, as you could have gone somewhere else, but I was hoping I’d guess right.”

“And you knew where I lived because…?”

“Ah. Erm. Because I followed you home tonight? Is that a bit weird? Sorry.” She could see him screwing his face up as if berating himself.

She laughed and pulled his arm further into her, settling him down into the valley between her breasts, which bumped into him with each step. “It’s fine.”

They reached her house and stopped on the doorstep, Rachel lifting the bag she was carrying, “Can I tempt you with a glass of wine?”

He hesitated, and the disappointment soured her good mood. Is he gonna go now he’s seen my tits? Is that all he’s after? “Please? I need hugs after doing things like that. I did tell you I would.” She winced a little at the pleading tone in her voice. “This is all new to me. I can’t just snap in and out of it, and what we did was scary in lots of ways. I exposed myself in public. I’m a 47-year old mother, not a young teenager. We’re pushing my boundaries here, but I need you to help me come down afterwards, to let me know it’s okay, otherwise I can’t do this.” Rachel felt the melancholy rush back in again, her arms wrapping around herself protectively and the tears forming out of nowhere.

“Hey. Don’t.” He pulled her to him, rubbing her back. “Sorry. Yes, a glass of wine please, if the offer’s still there?”

She sniffed and wiped the tears on the back of her hand, then nodded and opened the door, stepping inside and gesturing for James to come in. She wasn’t sure where Rob was, but she fervently hoped he’d stay well away for a while.

Glasses full of red wine, Rachel led James into the conservatory and gestured to the twin sofa while she walked around turning the electric heaters on.

Bang! The front door slammed and her heart sank. Fuck! Not now! Give me a break, life.

Rob appeared in the kitchen, Scott behind him, “Hi Mum. What ya- Oh. Hi.” He looked suspiciously at James and Rachel tugged nervously at her jacket, thanking her lucky stars she’d kept it on.

“Hi Love. This is James, my colleague. James, this is my son, Rob and his friend, Scott.”

The boys nodded at James, who said hi back, and there was a second or two of awkward pause while no-one knew quite what to say, and then Rob decided they were going to Scott’s house but that he’d be back tomorrow, said with a scowl.

Rachel exhaled as the door slammed shut again. “Sorry. I never know when he’s coming or going. Hazard of life around here, I’m afraid.”

“Don’t apologise,” James shrugged, but the moment was slipping even further away again.

Time to be brave. She took a large swig of her drink and set it down. “I still need my hug,” she said expectantly, her heart beating faster in case he rejected her advance.

His arms opened up and she moved forwards into them, her body moulding against his, seeking out his warmth for her chilled bones. They lay a few moments, rubbing each other’s arms and back, then Rachel sat up and shrugged her jacket off.

James’s eyes dipped to the outline of her breasts, reaching out tentatively, “May I?”

The annoyance flooded her brain before she could stop her mouth. “Stop asking. You’ve touched me before.”

“Yeah, as part of a dare. But that’s different to this.” He withdrew from her, shifting back in his seat.

She frowned, crossing her arms over her chest. “No, it’s not. Not to me anyway.”

“It is. The dares, my part in them, it’s like acting, taking on a persona of someone you want to be, rather than the person you are. On a dare, I have your permission, your consent, to do what I want within the boundary of the dare. Here, it’s all undefined. It makes me uneasy and it’s why I’ve stuck to online interaction for the longest time, safe behind my computer screen instead of this. I’m tying myself up in knots trying to think and act like he would, rather than just being me. Because it’s him anyone would want, isn’t it? PeepingTom? Not me.”

“What a load of bullshit! That last bit, I mean,” she exclaimed. “I noticed you, James, before I realise who else you were. I felt the draw to you when we had lunch. Lunch that I asked you to, by the way.”

“Only because PeepingTom got to you first. You’ve known me for years at work and I barely even got a glance from you,” he said heatedly.

Rachel felt the anger sweep over her. “Being a mum consumes you, James. The worry, the guilt, the fears, the happiness, the panic that you haven’t done your best for them. Then add an actual job on top of that, and a husband, then a divorce, and parents, and friends, and the list goes on. There’s no space left for you as a person and then suddenly you realise you’ve disappeared somewhere along the line, only to be spat out once everyone else has moved on with their lives. Don’t be so bloody arrogant to think everyone else’s reactions are because of you. Me not having the energy and capacity to see you was nothing to do with you and everything to do with me.”

The anger left her and the sadness flooded in, deflating her. She was tired now. Tired of all this. It was only meant to be a bit of fun. “I’d like you to go now. You’re both sides of the same coin to me. Kind, supportive Work-James encouraging me to stand up for myself, and confident, pushing-my-boundaries PeepingTom. One and the same. And I like the package they come wrapped up in, the one that’s standing in front of me now. But I don’t have the energy for this.” She circled her hand between them, then gestured towards the door. “I don’t want you to be in control all of the time, because I wanna be in control some of the time too, but just stop apologising for being you. Because you’ve got more going for you than you think.”

James gave a curt nod and stood, leaning in to kiss her cheek. “I’m not going to say sorry for ruining the evening because I don’t want to risk pissing you off even more, but you were amazing tonight. I’ll do better next time in real life, I promise. If you’ll give me another chance.”

And then he was gone, closing the door behind him.

She sat in silence, the clock ticking on a distant shelf, yet the noise filling her ears. She couldn’t imagine the awkwardness of doing this again, of there being another ‘next time’.

But…sometimes people just need a supportive nudge, rather than the whole grand gesture of a pressurised, over-hyped, new opportunity. Just a small sign that someone believes in them can make a huge difference, like how he’d nudged her at work to make her voice heard. If she’d needed a nudge then, maybe he did now.

Maybe she wasn’t quite ready to give up on him yet.

She put the door on the latch so it would open, grabbed her phone, her fingers flying over the keys, then took the wine and glasses from the conservatory, heading upstairs. She whipped the blouse over her head, unzipped the jeans and shimmied out of them along with her new instrument of torture, a lacy thong. She’d liked the way it felt, for all of five minutes before it got annoying and bloody painful. A quick squirt of perfume and she pulled her body moisturiser out, putting it on the bedside table, then lying face down on the bed.

Will he accept the dare?

She listened carefully, the blood pumping in her ears.

She thought she heard the front door coming off the latch and locking shut.

She thought she heard the creak of the third stair up.

The squeak of her bedroom door being closed had her breath hitching in anticipation, fighting the urge to turn around and look.

Ragged exhaled breaths filled the room and she imagined him gazing at her naked body. Imagined his eyes trailing over her back, lingering on her arse, checking if there was a hint of Pussy exposed between her closed legs, following the curve of her legs down, and then back up again.