May the Best Twin Win

*****

A few days later Tessa was due to meet up with her friend Maya at a nearby mall. She didn't have to leave until midday so she spent the morning lying in bed with her laptop perched on her knees, adding the finishing touches to a story she'd been writing. She'd decided to start documenting her adventures and upload them to Literotica for other people to enjoy, and whilst she knew that most people would assume that all the tales were made up she'd still enjoy the knowledge that every word was in fact totally true. With her first ever submission uploaded for review she got up, got changed, and then set off in her car. She was already half way through the twenty minute drive to pick up her friend when Maya rang with bad news.

'Hey Tess, you're not already in the car are you?'

'Err yeah, I'm like ten minutes away, are you ok?'

'No, so bad news...'

Maya apologetically explained that her little brother had managed to fall off his bike and hurt his arm, so she was currently on her way with him and her mum to the hospital, and would have to cancel their day trip. Tessa said it was no problem and wished them all the best, and then decided to go into town for an hour and pick up some books from the library, and then head home.

'Huh?' As Tessa rolled up to the house she was surprised to see a strange car sitting on the driveway, one she'd never seen before. She parked on the roadside instead and switched off the engine as she wondered who's it could be. For some reason her instincts told her to tread carefully, so she silently let herself in and listened intently as she paused in the corridor. A men's pair of trainers were sitting on the shoe rack, and from the floor above she could hear the unmistakable sound of bedsprings creaking. It wasn't Chester's Audi outside though, and her parents were definitely still at work, so what was going on? Tessa tiptoed up the stairs and along the corridor until she was at Jasmine's bedroom, and sure enough it was there that the squeaking and moaning were coming from. The door was slightly ajar, so Tessa very carefully nudged it further open, and then peered inside.

'Oh Jaz, no...' Sure enough there on the bed was her sister, thankfully hidden by the duvet, and thrusting on top of her was a burly man with a large afro. Tessa didn't loiter, she had no desire in hearing Jasmine's sex noises, but the distinctive hair and muscular physique was enough to tell her that the mystery guy was none other than Patrick, Chester's fellow wrestling partner, and more importantly his best friend. Tessa pulled the door shut again, then leant against the wall and groaned. Damn, this was really, really bad...

*****

For a few hours Tessa hid out in her room, wondering what she should do. As mentioned earlier she and Chester had been quite friendly before Jasmine had got involved, and so she did feel a sense of duty to tell him what was going on, he deserved to know. As late afternoon approached she heard Patrick and her sister heading downstairs and she watched from her window as his car drive off down the road, presumably there were headed back to his house for the evening, probably for some more illicit sex. That made Tessa's mind up for her, so she pulled out her phone and messaged Chester.

'Hey Chester, it's Tessa. Bit of a weird one, but are you free right now? I need to talk to you about something.'

His reply came quickly. 'Yeah sure, what's up?'

'Just come over, please? I think this should be done in person.'

'Umm ok, if you want. I can be at yours in twenty?'

'Ok, see you soon.'

Tessa waited until Chester turned up at her doorstep, then invited him into the living room and proceeded to fill him in. They sat on the sofa as she told him what she'd seen earlier that day, and as expected he wasn't exactly thrilled by the news.

'Fuck man... fuck! I can't believe that she'd do that to me... or that he would, either! I don't know who I feel more betrayed by... those fuckers man...'

Tessa could only nod sympathetically, she'd been cheated on once before too and knew that it wasn't much fun. Chester kept ranting, getting up and pacing the room as he vented to her.

'Like really, what the hell was Jaz thinking? She knows Patrick's my best friend, why would she go for him of all people?'

Tessa shook her head sadly.

'I don't know, she isn't the nicest person sometimes.'

Chester balled his fists angrily.

'It kind of makes other stuff make sense now... like she kept cancelling on me last minute, and only gave really weak excuses. Like today we were meant to be going to a waterpark together, but she messaged this morning saying she was ill... when really she was screwing Patrick. Man, I'm going to fucking kill that guy...'

Tessa just stayed silent as he carried on thinking out loud.

'Also... do you remember Alex?'

Ohhh, Tessa thought, now she knew who that pizza deliver chick was... of course, Alex, a girl she'd gone to college with.

'Oh, vaguely, why?' She tried her best to act casual, even though she feared she knew what was coming.

Chester elaborated.

'So we're still mates and the other day at a party she was trying to convince me that she'd made a pizza delivery here recently, to your house. And when she'd opened the door Jaz had answered it, and she'd been completely naked for some reason. I assumed Alex was just drunk and being stupid and making it up, but now who knows? I don't even know Jasmine anymore, maybe that is the sort of thing Patrick gets her to do...'

Tessa sighed. 'No, she wasn't making it up...'

For the first time Chester's train of thought was interrupted, and he looked down at her questioningly.

'What?'

'Umm...' Tessa bit her lip nervously as she debated whether or not she should do this. She didn't know why but contrary to all rational thought she had a really strong gut feeling that she should be honest right now, come what may. Finally she made her decision.

'Ok, err Chester? Can I show you something?'

Chester was confused, and didn't see what this had to do with Jasmine or Patrick, but agreed regardless.

'Yeah?'

Tessa frowned.

'No but before I do, you have to swear that you won't tell anyone.'

'Ok, I swear.'

'No but really though, literally not another soul...'

'Tess I promise, ok? Now, what is it?' Chester stopped walking up and down the room and turned to stare at her quizzically.

'Ok... wait here.' Two minutes later Tessa reappeared through the doorway in her fully disguised form. She'd swapped her clothes with an outfit from Jasmine's wardrobe so her transformation was uncannily accurate, even Tessa thought that it was a little spooky just how much like her sister she looked. Chester looked like he'd seen a ghost as he saw her walk in, he clearly thought that his unfaithful girlfriend had just unexpectedly appeared, and he took a step back in surprise.

'Jaz? What are you-'

Tessa giggled and shook her head.

'No you idiot, it's still me.'

Chester gasped with relief and then burst out laughing.

'Oh my God, Tess? What the hell, that's so freaky! I was so sure that you were Jasmine...'

Tessa struck a pose as she watched him eyeing her up and down.

'It's pretty good right?'

Chester walked around her slowly as he studied her.

'It's insane... I assume this is a wig? It really sells the look... and then the nose ring, also fake I'm guessing... and then the glasses, nice touch. And the outfit too... so simple but so effective.'

Tessa was proud of her work and all the appreciation it was receiving.

'Think you'd be able to tell us apart? If she walked in right now, I mean?'

Chester exhaled ruefully.

'I mean it would be close, but the devil horns sticking out of her forehead might be a bit of a giveaway... wait, hold on.' A switch in his brain seemed to have flicked on and he groaned slightly as he put two and two together. 'So when Alex said she saw Jaz, naked...'

Tessa blushed bashfully, this was the moment where finally her secret was about to be exposed.

'Yeah... so Alex was only kind of wrong, she didn't see Jaz, but she did see me... dressed as her... well not dressed, but you know...'

Chester stared at her in obvious confusion, he knew what she meant but still didn't see how that could possibly be true.

'You did what?'

Tessa sighed and bounced down onto the sofa, then patted the cushion next to her.

'Oh God, you're going to think I'm insane... ok come here, sit down. So, it all started a few weeks ago when Jaz stole my towel...'

*****

It took Tessa half an hour to tell Chester about how ridiculous her life had becoming in the last couple of weeks, especially as he kept interrupting her with endless questions or general remarks of disbelief. Eventually she made him understand though, that she'd been indulging her exhibitionist desires risk free by pretending to be her twin sister, and by the end of it she actually felt pretty good, despite the obvious embarrassment. It was actually a relief to get everything off her chest, and to share her story with another human being. Chester nodded slowly as Tessa finished up with her description of her naked streak from the police car.

'Ok... I get it now. Like I don't understand you or anything, or why you do any of it, but I do get how you do it.'

Tessa thought that was good enough, for now at least.

'Ok... good. So, do you still think I'm a freak?'

Chester rubbed his eyes and laughed quietly.

'Well yeah... but in a good way though. Like a sexy freak, I guess.'

Tessa batted her eyelids suggestively, she still very much had a crush on this boy and that one little compliment was all she needed to hear.

'Well in that case, Chester... would you like to go for a walk? With "Jasmine", I mean...?'

Chester grinned as he realised what she meant.

'Oh yeah, of course. Lead the way, "Jaz".'

*****

'Are you sure you won't be cold?'

The pair strolled along the road, breathing in the cool evening air, and admiring the last remnants of the sunset which was fast dissolving away into the blackening sky. Tessa hadn't bothered to put anything extra on for their walk, and she looked pretty underdressed compared to Chester in his warm thick coat. She shrugged cheerfully at his concern.

'Nah... like I say, I think my body has started to adapt to not wearing much.'

Chester smirked.

'Not wearing much?'

'Ok... much, or anything at all...' Tessa glanced up at him flirtatiously, she was enjoying chatting to him again, even under these very weird circumstances. 'So what, you never just walk around the house naked? Just for fun?'

Chester laughed at the idea.

'Not when I'm at home I don't, I've got two older sisters to think about. At my place at uni I might just walk around in boxers, but only because it's an all boys flat. I definitely wouldn't go around nude though, or answer a pizza delivery like that, I think I'd get arrested.'

Tessa laughed too.

'Yeah... I guess it's easier for girls.'

Chester smiled as he looked down at her.

'Definitely, no one's complaining when it's a body like yours on show...' He trailed off, but now there was definitely a bit of a spark developing between them. 'So how did you come up with the pool idea, or flashing the office workers?'

Tessa had to think for a moment, she'd never really thought about it.

'I don't know, mostly they're just impulsive decisions I make on the spot, they're not planned out or anything.'

'So when you have an idea you just challenge yourself to see if you can do it?'

Tessa agreed.

'Yeah kind of. It's like a dare I guess, a self dare.'

'Ok, ok. Well, in that case I dare you to...' Chester looked around as he searched for inspiration and tried to think of something interesting to make her do. 'Umm, I dare you to walk from here to the traffic lights on the corner, but with your top pulled up.'

A warm tingly feeling swept through Tessa's body, did he really just say that, was this actually happening? After so long reading about these kinds of moments on Literotica was it finally her turn to have a hot guy giving her naughty dares in to complete in public? Because honestly, that was kind of the dream...

'Those ones down there?' They were on quite a long road, and although the streets were generally quiet in Tessa's area there were still plenty of cars driving around.

Chester shrugged, after all the stories he'd just heard he didn't think the idea was too insane.

'Yep.'

'Ok...' Tessa took in a deep breath and nervously glanced behind them, but the coast was clear. She pulled her sister's crop top up over her boobs, flashing her nipples to Chester for the second time, and let the top rest up high on her cleavage. Chester's eyes nearly popped out of his skull when he saw her bare tits as he hadn't banked on her going without underwear.

'Oh shit, Tess! You're not wearing a bra!'

Tessa giggled as she looked down at her unrestrained boobs swaying from side to side as they continued walking.

'Yeah, nah... to be honest I've kind of given up wearing them entirely. It's just comfier, you know?'

Even though Chester had seen them before, and seen Jaz's a hundred times, he still couldn't tear his eyes away, which Tessa took as a compliment.

'Sorry, I wouldn't have asked you to lift your top up if I'd known that you didn't have anything on underneath...'

Now it was Tessa's turn to shrug cheekily.

'Why not? A dare is a dare, right?'

Chester pondered.

'I guess, but I don't know many girls who'd have the balls to do this...'

They kept chatting as a few cars passed by and made Tessa instinctively flinch every time, but to be fair to her she never once tried to cover up as she let everyone get a look at boobs. Chester was very impressed by her bravery as she completed the task when they reached the junction before turning left, heading towards the center of town, but even then Tessa showed no signs of embarrassment.

'So, what next?' Tessa knew that she'd passed the first challenge and could cover up again, but she didn't want to, and Chester noticed her confidence with amusement.

'Err ok... right, you see the row of shops down there?' Again he pointed to a spot a couple of minutes walk away, where the risk of meeting other pedestrians was even greater.

'Yup.'

'Ok, until we get there how about you flash the cars behind us too?'

'Ok, you're the boss.' Without any hesitation Tessa tugged down the waistband of her skirt at the back, revealing her bare butt cheeks which wobbled from side to side as they were pushed up by the elastic hem. Chester laughed when he saw her mooning the entire neighborhood.

'For God's sake Tess! So what, you don't wear any underwear now, at all?'

Tessa smiled cheerfully.

'Nope. Come on though, seriously, what's the point of wearing a skirt if you don't go commando...'

'Hey, I'm not complaining...'

Tessa easily completed the next leg of the dare, even though a couple of trucks gave her appreciative blasts on the horn as they swept past her from behind. They reached a pedestrian crossing by the shops and again Tessa didn't worry about covering up again, instead she just calmly looked up the road and waited for a gap in the traffic.

'Ah!' As she waited for the lights to turn green Tessa gasped as her already low hanging skirt was violently yanked down from around her hips and in an instant was lying crumpled around her feet. She looked back accusingly at Chester who just chuckled as he looked down at the practically naked girl standing in front of him, with only the thin line of her top around her neck giving her any cover, and he was clearly pleased with his successful prank. The lights on the road turned red and suddenly to Tessa's left and right there were two rows of cars waiting for her to cross. She calmly stepped out of her skirt and walked bottomless across the road, Jaz's top still hiked up over her boobs, as she boldly strode confidently with her hands at her sides.

'Holy shit...' Chester picked up Tessa's discarded skirt and jogged after her, glancing at the shocked drivers' faces who were also staring after her bare behind as she reached the other side. Tessa went straight over the opposite pavement and headed down a small alleyway which led to the town's river, and had a couple of paths lining it on both banks. It provided a quieter route into the city center's shops and cafe's than the main road, and seeing as there was no one around Tessa felt bold enough stayed undressed, mainly just to show that Chester hadn't managed to outdo her. Her new partner in crime caught up with her and slapped her on the butt playfully, which startled and pleased her in equal measure.

'Hey, you can look but you can't touch, mister,' she joked.

Chester sarcastically apologised and then held up the bundle of material in his hand.

'Ok ok, sorry. Hey, these are Jasmine's clothes right? I think I recognize this skirt.'

Tessa looked over at him suspiciously as she strode along and tried to pretend that everything was normal.

'Err yeah, they are. Why?'

Chester smiled as he rubbed the fabric ruefully between his fingers.

'Well, that bitch did just cheat on me with, my best friend, so I feel like I deserve a little bit of revenge... and I know she likes this outfit.' He bunched up the skirt in his fist and threw it into the river, where it was quickly swept away by the current.

'Umm...' Tessa watched dumbfounded as half of her clothing floated away out of view, never to be seen again. 'Well... did that make you feel any better at least?'

Chester nodded thoughtfully.

'You know what? It really did, now I see why people key their ex's cars or smash up their phones, this does feel therapeutic. I kind of want to do it again...'

Tessa saw where this was going and wasn't entirely sure that she liked it, flashing in public was one thing but getting rid of all her clothes entirely seemed a bit extreme, even for her. She looked down at her top with concern.

'Wait a second, maybe we should-'

Chester came to a stop on the path as he stepped across her path and interrupted her.

'Tessa?'

'Yeah?' Tessa gulped as she got a sudden and very intense flashback to her time with Dwight the fictional rugby captain.

'Arms up. Now.'

'Damn...' Tessa had never been ordered to strip naked before, and definitely not when stood out wide in the open, but the quiet confidence and firmness in Chester's voice sent a tingle down her spine. She obediently raised her arms as she looked up at the wrestler with large, trusting eyes, and he grinned down at her as he gently peeled her crop top off her body. For the second time in two days Tessa found herself standing completely nude miles away from her home, and she absolutely loved it.

'Yeah... I know Jasmine really likes this top as well... shame.' Chester lobbed Tessa's last piece of clothing into the river too, and they both watched it flow downstream. Tessa rolled her eyes at Chester's foolhardiness, but they both knew she wasn't really mad and actually she was trying her best not to explode with a mix of excitement and worry. So instead she coolly extended her hand out to his, and together they continued their evening walk down the river path as if nothing was out of the ordinary. For the next five minutes they enjoyed the ducks quacking, the summer birds tweeting, and the idyllic evening peace. But then, away in the distance, Tessa saw a big problem.

'Chester! Up ahead!' She nervously cupped a boob with one hand as she saw a large group of joggers, maybe twenty or so middle aged men and women, running towards them on the parallel path across the water.

Chester just shrugged.

'So?'

Tessa blinked incredulously.

'What do you mean, so? I'm naked here!'

'Yeah, but they're on the other side of the river, they can't hurt you.' Chester was right but it wasn't a huge source of comfort for the very apprehensive Tessa.