Note: This story was dynamically reformatted for online reading convenience. ï>¿May The Best Twin Win by ThanksForAllTheFish 'Oh no problem, don't worry about it...' Chester couldn't take his eyes away from her bulging cleavage, and Jasmine noticed his look of lust with disgust. Tessa grinned back at him. 'Actually you know what, if you've already seen hers then you've basically seen mine, right? One of the weird things about being identical twins I guess!' She didn't wait for a response and casually dropped her arm, tingling with excitement as she tried to appear cool when she walked over to their side and squatted down by, knowing that her tight booty shorts were giving Chester a great view of her ass. She unplugged a charger in the corner and then stood up and confidently allowed the astonished pair an unrestricted view of her semi nude body. 'Well I'll leave you two lovebirds to it, goodnight!' She sauntered away from them and made sure to sway her hips provocatively. When she reached the hallway she had to stifle a laugh, she couldn't believe she'd just flashed a hot guy just to annoy her sister! It had definitely worked though, if looks could kill then Jasmine would have knocked her dead on the spot, such was the anger and jealousy that had been burning from her eyes. Tessa chuckled to herself as she walked into the laundry room by the kitchen and pulled off her shorts, adding them into the washer along with her shirt, and although the temptation to head back into the lounge in her birthday suit was alarmingly tempting, she reigned herself in and headed back upstairs in search of her bed and more importantly her vibrator. ***** The next day Tessa was surprised to see a letter addressed to her that was from her insurance company. It was a warning that her monthly fee was going up by fifty percent, in response to the speeding charges that had recently been added to her license. The weird thing was that Tessa had never been stopped by the police in her life, but the letter clearly stated that she'd been pulled over and charged last Tuesday. Last Tuesday, the day she'd been at her friend Maya's house, and hadn't used her car at all... 'You bitch...' Tessa barged into Jasmine's room who peered up at her groggily from beneath her duvet as she was unexpectedly awoken. 'Hey, what the-' Tessa interrupted her aggressively. 'Last Tuesday, you stole my car?' Jasmine sighed and shut her eyes again as she leant back onto her pillows. 'What? Oh, no I didn't steal it, I just borrowed it.' Tessa was raging. 'You still don't even have your license! What did you do, steal mine too?' Jasmine frowned. 'No, of course not... I borrowed that as well.' Tessa gesticulated wildly with the insurance letter. 'And then you were caught doing what, sixty miles an hour in a forty? Are you insane?' 'I was running late!' Jasmine shrugged as if it were her sister that were in the wrong, and not her. 'Fucking unbelievable...' Tessa didn't want to hear anymore, she just slammed the door shut and walked out. ***** Tessa seethed quietly as she worked the rest of the day, but by the afternoon she was tired of revising and she decided to get dressed and go out for a walk to clear her head. On a last minute whim she pulled on the pink wig and put her glasses and nose ring in her pocket, then tugged on her hoodie and pulled it over her head so her parents wouldn't notice her hair. 'I'm leaving for a bit Dad, just going out for some air, see you later.' She called out her goodbyes as she quickly nipped past the kitchen door, then she pulled on some trainers and headed out into the afternoon sunshine. Once she was out of sight of her house she donned the glasses, clipped the nose ring on, pulled down her hood and voila -- she was now Jasmine once more. It was kind of like she'd discovered a new super power, if her sister did anything to piss her off then that gave her enough motivation to get dressed up and do something risky, without feeling any guilt. It was petty, sure, but very fun, and because she was in disguise it was kind of risk free, right? Tessa walked around her neighbourhood for a while as she listened to some music, but after half an hour she groaned as her headphones suddenly ran out of charge and died. 'For fuck's sake...' Tessa wandered aimlessly for another few minutes but now she was bored and ready to return home, until then she decided that she might as well have some fun along the way, seeing as she had got all dressed up. On her route back she approached a street which was lined with high rise office blocks, where every level had floor to ceiling windows which looked straight out over the pavement. It was early evening now and most places where shut, but these buildings still had all their lights on. 'Hmmm...' Tessa walked in front of one of the office blocks and saw that on the ground floor there were still a few sad looking employees hunched infront of their desks typing away, presumably working late to fulfill some deadline. Tessa thought that she could help to brighten up their depressing evening, so she nipped into an alleyway next to the first office and waited for a gap in the traffic so she could quickly unzip her hoodie and strip off her t-shirt. Bras weren't really her thing anymore so she was now topless and shivering as the cool evening air blew over her exposed skin, so she hurriedly pulled her hoodie back on and stuffed her shirt into a pocket, then leisurely strolled back onto the street. 'Come on Tess, you can do this...' She psyched herself up as she slowly walked into view of the row of office windows as doubt started to creep into her mind, but then she reminded herself that with her disguise she could do anything she wanted, and decisively pulled her zip down. Tessa let her top flap open up wide as the two halves fell to hang uselessly at the side, and her bare torso was free to peak out from in between. Her boobs proudly poked out in front of her and she forced herself to keep walking slowly with her back straight and her head held high, even though the temptation to cover up was almost overwhelming. No one was walking down the street towards Tessa but she did glance inside the office to her right, and was half delighted and half humiliated to see a young woman, about her own age and dressed smartly in a business suit, staring open mouthed back at her. The employee reached over to the guy sitting next to her and shook his shoulder, and her colleague did a double take when he too saw Tessa nonchalantly strolling past the window with her tits out. 'Oh my God...' Tessa's nerve held out for a few more seconds as she let the pair get a good view, but then she finally felt too shy and wrapped her hoodie tightly back around her bust, holding it tightly in front as she skipped away out of sight. Laughing hysterically she reached a junction in the road and held her top closed as she nipped across it, determined to increase the risk on the next leg of her journey home. There was no alleyway before the next office block but there was also still no traffic or pedestrians around her, so in a moment of horny madness Tessa glanced around and then giddily tugged down her leggings and underwear in one swift motion. Now standing on a public street completely bottomless with her hoodie fapping open she hoped on one leg as she got her clothes down over her shoes, then balled them up and shoved them into her top's other pocket. The hoodie was just long enough to cover her pussy and the top half of her butt but no more, and the breeze on her bare skin felt incredible as she carried on down the street and into the view of the second office building. Inside it was busier than the first but wasn't open plan, everyone was separated into little work cubicles, and the nearest row were the ones which had a view out onto the pavement. As Tessa walked past them her hoodie rode up her hips and she didn't try to fight it, instead she let it climb until her butt was completely on display. Most of the people inside didn't look up as they stayed glued to their screens but a couple did, and Tessa giggled as she felt their eyes burning into her bare cheeks as she swayed on past. 'Damn...' Tessa's eyes lit up as she spied a ridiculously hot guy sitting infront of his desk, she could see his biceps straining against his short sleeved shirt and his tight trousers left little to the imagination. He was wearing headphones and hadn't noticed Tessa walking by, so she decided to fix that by tapping gently on the glass. He clearly didn't hear that either, so Tessa sighed and turned her back to the window, then hiked up her hoodie and planted her butt against it. She looked over her shoulder and laughed out loud when she saw that she'd finally won his attention, and the man was staring down at her as she wiggled her booty against the glass. 'Shit!' Her flashing and flaunting was interrupted as a lorry turned onto the road and Tessa squealed as she quickly shoved her top back down to cover her up. The truck rolled by and Tessa blew her office voyeur a cheeky kiss goodbye and moved on to the next row of cubicles. She kept her fists clenched in her pockets but allowed her top to fall open again as it fell away down her shoulders and bunched around her waist, so now she was just one slip of the hand away from total nudity. A couple more workers were treated to the sight of her bobbling tits as she smiled perkily back at them, and her confidence had grown so exponentially over the last few minutes that she decided to give the last few cubicles an extra little show. 'Tadaaa...' Tessa grinned through the window as she held her hands out, which were still wedged deep inside her pockets, and displayed her whole pale body as she provocatively shimmied her hips and made her tits dance. This was it, she thought, before she had been able to claim that she was just a girl who didn't like wearing clothes at home, and who might occasionally open the door in the nude. But now she was a full blown flasher, an exhibitionist who got off on displaying herself to strangers, and she didn't think she'd ever be able to go back. Before her luck ran out she pulled her top closed again and turned away, satisfied that she'd given half the office a good topic of conversation for their next coffee break. Tessa strode over another side road and noted with a twinge of disappointment that the next glass fronted office block was the last in the road, and after that there was just a row of shops which had already closed for the night. She was also alarmed to see that in this company there weren't just working late, they were having a full blown staff meeting. A bus rumbled behind Tessa as she nervously loitered by the side of the building and peered through the window and scouted out the place. There was one fat man standing with his back to the street, who appeared to be giving some sort of speech or lecture, and arranged in a semicircle in front of him were thirty or so employees who were pretending to pay attention. Some were leaning back in their office chairs, a few were standing as they tried not to fall asleep, and a couple made eye contact with Tessa as they noticed her peering in at them. The university student had been seen by what, around seven or eight people so far, and even then by at most two at a time, so flashing an entire room full of people at once was obviously going too far... right? 'Fuck it...' Tessa knew that this was getting really stupid, but she also knew that she wouldn't forgive herself if she just bailed and went home now, this opportunity was just too irresistible. And again, she reminded herself, it wasn't her doing this, it was her sister, it was really Jasmine. 'Ok... come on Tess.' She took a few steps back so that she was hidden from view again, and reached down to untie her shoes. She didn't know why but suddenly it felt very important to do this as thoroughly as possible, she wanted the full experience. She tugged the trainers off and her socks soon followed, and she stuffed those into her shoes. The rough tarmac bit into the soles of her feet and it made her feel so much more conscious of her body, and so much more aware of the outside elements interacting with it. She had to awkwardly shift her weight from side to side to stop her toes from freezing as she waited for a guy on a bike to cycle past and disappear down the road, but after that there was nothing left to hold her back. 'Ahh!' So with another nervous shriek of excitement Tessa tugged her hoodie off, peeling the sleeves back off her arms, and then hooked her finger into the hood and slung the top back over her shoulder, letting it hang down her back. She bent her knees to pick up her shoes with her other hand, then straightened and with a huge deep breath took her first step back along the road. She was instantly bathed in the cool glow from the office's lights as she reappeared back into view, now totally naked from head to toe. For her first few paces Tessa couldn't bring herself to look to her right, and instead she kept her head locked in place as she forced herself to walk calmly and slowly past the window. However after a couple more steps her curiosity won over and she found her neck slowly rotating round until she was staring in through the glass. 'Woah...' An involuntary gasp left her mouth as she was greeted with the sight of thirty shell shocked faces gawking back at her as their wide eyes drank in the unexpected sight of her wonderful curves. Every man and woman had their gaze locked firmly on Tessa's body, and she slowed to a stop as she took in the ridiculous situation that she'd created. The boss speaking at the front had finally noticed that no one was paying attention to him anymore and he too turned around, doing a hilarious double take when he noticed the nude university student standing just a few feet behind him. 'Hi...' Tessa smiled bashfully as she turned to stand face on to the office block, allowing everyone to get a better view of her, and she raised her right hand and twiddled her fingers in a shy little wave. No one responded apart from one young woman standing at the back of the crowd, who also waved back as a large smile broke out on her face. Clearly one person at least appreciated the daring confidence that Tessa possessed, and was also grateful to her for making their evening meeting less dull. Suddenly though Tessa was brought back sharply down to earth as she heard a car approaching from down the road, and which sounded like it was accelerating hard. She looked back the way she'd come and her heart stopped when she saw the flashing blue lights of a police car heading down the street directly towards her. 'Shit!' For a second Tessa was frozen to the spot in fear as she her mind refused to do anything but panic, but then her instincts kicked in again and she started to sprint down the pavement. The office workers all flocked to the window and craned their neck as they tried to watch her run away, but soon she had disappeared from view. 'Fuck fuck fuck fuck...' She swore vehemently as she awkwardly tried to clasp her wildly flailing boobs with her arms, but one of her socks fell out of her shoe as she tried to restrain both her tits and the hoodie which was flapping away behind her. She really regretted taking off her trainers as her bare feet pounded against the rough paving stones, and wished she'd spent more time at the gym as she streaked away at a not very impressive pace. She turned off the main road without having time to check if the way ahead was clear, and sure enough walking up the pavement was an elderly man, leading a small dog on a lead behind him. 'Shit, I - err sorry!' Tessa cringed as she ran past the stranger, who turned to watch her go, but she had to keep moving no matter how embarrassed she felt. At the end of the street there was a building site lined with chain linked fences, and as Tessa took a tight right hand turn the zip from her hoodie flicked out and got caught in the wire. 'What the -- oh God, no, no no no...' She forlornly turned and hunched over as she tugged futilely at her top's sleeve, which achieved nothing, and so she instead tried to calm down and unhook it, but her hands were shaking with adrenaline and fear. 'Goddammit Tess!' She cursed her recklessness as she looked back and saw the cop car turn into the road, and rev its engine as the officer saw her standing there naked on the corner. Tessa gave the hoodie one last desperate pull, then finally admitted defeat and frantically tugged her t-shirt and keys from the pocket. 'Fuck!' She scrambled to get at the other side of the hoodie for her leggings but there was no time, she had to keep running, and so with a exasperated cry she picked up her shoes and rushed down the nearest side road. It was a quiet suburban street lined with fancy looking homes, and when Tessa was sure she was out of the police car's line of sight she launched herself over the hedge that bordered one of the house's front gardens, and groaned as she landed with a thump on the cold hard lawn. She rolled onto her back and grimaced as several sharp twigs pierced into her flank, and stared up groggily at the darkening sky as she wondered how on earth she had got herself into this ludicrous situation. When she looked to the side Tessa was relived to see that the windows of the house remained dark, then she instinctively hugged herself as they reflected the blue light of the police car as it rounded the corner and sped past. Luckily her trick had worked and she sighed in relief as she heard the roar of the engine carry on down the street, and then screech of the tyres as they rounded another bend. 'Thank you lord...' Tessa stayed lying there motionless for a few more minutes until she was sure that she was in the clear, then she stiffly got up to her knees and brushed the dirt off her skin. Her heart showed no signs of slowing down and it continued to beat out of her chest as she dusted down her t-shirt and then pulled it on, along with her shoes and socks. She peeked over the hedge to make sure the road was clear, then exited the garden through the front gate this time, and awkwardly hurried down the pavement as she kept her top pulled down in a futile attempt to keep her pussy and butt covered up simultaneously. 'Oh you're kidding...' Tessa got to the fence on which her hoodie, and more importantly her leggings, had been hanging. To her dismay it was no longer there, and she turned to scan up and down the street and peered into the dark, trying to see if anyone was around. There was nobody to turn to though, and no way of knowing whether or not some random passerby had stolen her stuff, or if the police had circled back and picked it up looking for some form of identification. Either way it didn't really matter and Tessa despondently looked down at her bare legs which poked out from below the hem of her shirt, and then started the long walk home. Ultimately the trip back hadn't been too bad, save for the first fifteen minutes. It was literally impossible for Tessa to keep both her front and back covered simultaneously, so whenever she reached a busy junction she just had to accept that she'd be flashing her butt to the waiting drivers as she rushed across the road. Luckily however she'd later come across a cardboard box which was lying discarded on the side of the road. With that held around her waist she was able to pick up the pace significantly as she power walked her way back to her street. After discarding her makeshift cover she'd unlocked the front door and sprinted past the dining room where her family were eating dinner, and she was just fast enough to avoid their gaze as she tore past the doorway. She pulled off her top as she went upstairs and headed straight to the bathroom, and in a few minutes she was busy playing with the shower head as it blasted hot water up between her thighs and made her cry out in sheer ecstasy. Overall, she thought, that had been the quite the evening stroll. ***** 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. 'But they can see me!' 'But isn't that kind of the point?' 'I mean...' Tessa faded into silence as she realised that yes, that was the point. She'd dreamt of being an exhibitionist and now she was living the lifestyle, and that meant getting seen in the nude by random strangers, like it or not. Chester nodded as he saw that she wouldn't offer up any resistance. 'Ok then. Now arms down, by your sides.' 'Jesus...' But Tessa complied and forced herself to take measured strides as she continued to walk by Chester's side, one arm clutching his bicep tightly. The runners didn't stop but they all slowed when they saw her, and Tessa's cheeks began to burn red as she heard them start to laugh and whisper about her. After what felt like an eternity they'd made it past them, although when Tessa looked over her shoulder she saw plenty of the guys still checking her out as they jogged away. 'Holy shit!' Chester squeezed her hand encouragingly. 'See, you could handle that no problem. Very impressive!' They walked on for another ten minutes and Tessa was seen by a few more walkers on the opposite bank, all of whom stopped to get a good look as she passed. They also met two strangers on their side of the river, a couple of young guys who were cycling up the path towards them, and who cheekily got off their bikes to let Chester and Tessa pass, pretending to be helpful when in fact it just meant they got to see her body up close as she squeezed by them. She loved every second though, and was disappointed when she saw that they'd started to reach the busier part of the riverside trail. They'd arrived at the point where the riverside began to become pretty lively, with lots of cafes and bars overlooking the water, and Chester paused as he checked the time on his phone. 'Hey, there's normally one last late showing at the cinema around this time. You want to go and see a movie?' Tessa looked down at herself and sniggered. 'What, like this?' Now Chester rolled his eyes. 'I don't think even "Jasmine" is that crazy... here, put this on.' He shrugged off his jacket and held it open as Tessa fed her arms through, then buttoned it up. It looked huge on her obviously, but it did come down to her knees which was nice given the rapidly cooling evening air, and her lack of any other clothing. Tessa giggled as she flapped the comically long sleeves around. 'I look like a penguin.' 'That's more than ok. Now come on, let's go.' They walked up a path which led to the town's center, and soon they'd reached the local cinema. Tessa felt silly in her new outfit but it was ok, it just looked like a boyfriend had kindly leant his coat to his chilly girlfriend, who had foolishly gone out for the night in a skirt or shorts. The cinema was quiet as there was only one film left for the day, so they bought their tickets and some popcorn and headed to screen four. They chose seats right at the back and munched on their snacks and slurped on their drinks as they watched the endless reels of adverts flash across the screen. There were about twenty other people dotted around the seats infront of them, but luckily no one sat on their row. 'How about another game...' Chester looked over at Tessa with mischief flashing in his eyes. 'For every advert with an animal in it, you undo a button.' Tessa giggled. 'Haha fine, deal.' They shook on it, and over the next ten minutes there were six pet or insurance commercials which featured a dog or a cat, so soon Tessa only had one button which was precariously holding the coat together. However at that point the screen faded to black, and finally the movie began. 'Oh, here we go...' The film was some romantic period piece set on a farm, and looked pretty boring, so Tessa immediately suggested a new game. 'How about every time we see a cow I undo a button?' Chester snorted. 'Yeah, sure.' The next scene immediately showed a large herd of cattle in a field. 'Ah no,' Tessa dryly remarked, sarcastically rolling her eyes in feigned regret, 'looks like I just lost...' She popped open the last button and let the sides of the coat fall away to the sides, revealing her pale body which glowed white under the light of the movie screen. She carefully pulled her arms free from the sleeves so that now she was just sitting completely naked in a public cinema, resting back on Chester's jacket as if it were a makeshift blanket. She folded her arms under her boobs, pushing them up gently so that they were even more outrageously plump than usual, and snickered when she saw Chester gawking at them. 'It's ok, you can touch them if you like...' Chester didn't need any encouragement and reached over to hungrily paw at her tits, groping and grabbing at them as Tessa squirmed ticklishly, trying her best not to laugh out loud. However what had started off as funny soon became more serious, and as Chester massaged her boobs Tessa felt herself getting wetter and more aroused. She reached out her index and forefinger towards Chester's lips, and after a moment of confusion he let her insert them into his mouth. She shivered slightly as his tongue licked her fingers up and down, and when they were suitably damp she pulled them back out and slowly inserted her now lubricated hand into her pussy. Now she was fingering herself in public as Chester fondled her mere feet away from a group of strangers, and it felt incredible. 'Well, what do we have here...' Chester was wearing relatively thin tracksuit bottoms, so when Tessa reached out and rested her hand on his crotch she could immediately feel that her display had achieved the desired result. 'Feels like you could do with some help with that...' Tessa never broke eye contact with Chester as she slowly slipped down off the jacket covered seat, until her bent knees touched the rough carpeted floor. She crawled round, hidden from the rest of the theater by the rows of chairs, until she was in between Chester's legs, which she gently eased apart. She pulled down his trousers just far enough to reveal his underwear, and she was pleased to see the unmistakable outline of his erection straining against the material. Tessa had heard from a friend of a friend that Chester was pretty well endowed, but she'd never asked her sister to confirm or deny that rumor, and now she'd get to find out for herself. 'Damn... I'd heard stories, I guess now I know they were true.' She gently pulled his already rock hard dick through the flap in his boxers, and let it spring free and point rigidly skywards as it was released from its confines. It was the largest she'd encountered in real life, not as ludicrously enormous as Dwight's magical cock from her fantasies, but still big enough to be pretty intimidating to a girl her size. It was also veiny and twitchy and clearly raring to go, and any feelings of nervousness were easily overpowered by her lust and curiosity. 'Oh God...' Chester moaned quietly as Tessa sat up slightly so she could reach him properly, then leant forwards and tentatively took his tip in her mouth, and wrapped her hands around his shaft. The film was relatively loud and the cinema's speakers gave them a decent amount of sound cover, so Tessa didn't have to worry too much about being heard. That meant she was free to suck and slurp away to her heart's content as she simultaneously blew and jerked Chester off, there was a lot of dick for her small hands to work with. 'Tess, oh my God, you're amazing...' Tessa was pleased that her oral skills were being appreciated, but she decided to switch things up regardless by moving on to her signature move, the titty fuck. Most men fantasised about getting wanked off by a girl solely using her boobs, but most women didn't have a deep enough cleavage to successfully give it a go. That wasn't an issue for Tessa though, and so she shifted forwards again and pressed her chest into Chester's crotch, enveloping his dick in between her massive tits. 'Fucking hell...' Normally when she did this the guy's cock would disappear completely into her deep cleavage, but Chester was just long enough so that the head of his dick could just peak out from between her boobs, and Tessa bowed her head to give it a loving kiss on the tip as she began to bounce up and down. 'So, did Jaz ever let you do anything like this?' Tessa whispered, as she continued to press her tits tightly together. 'No, no never...' 'I'm glad...' 'You know what else she never agreed to do?' Chester looked into her eyes with a look of pure lust. 'What?' Tessa was beginning to pant now as she started to tire from her exertions. 'She would never, umm, swallow, if you get what I mean...' Chester glanced up at Tessa nervously, worried that he might have finally pushed his luck too far and broken the spell. Luckily for him Tessa just smiled and bowed her head again as she whispered to him in between mouthfuls. 'Well, I've always said that spitters are quitters...' Tessa wrapped both hands back of her around his shaft, opened her mouth wide, and began to furiously finish him off. ***** The film was barely past the ten minute mark by the time they'd finished up but they didn't care, their work at the cinema was done. Chester had tucked himself back into his trousers and then passed Tessa his coat and she'd reluctantly slipped it back on, sad to be wearing clothes again. It turned out that Chester had the balls to match his large dick, and they'd produced so much semen that despite her best efforts Tessa had been unable to gulp it all down in one go. Her mouth had been full to the point of overflowing and a small dribble of cum had escaped out the side of her lips, and trickled down her chin. Chester helpfully pointed this out but Tessa just shrugged cheerfully and linked her arm through his as they exited the theater. She'd always wanted to do a public cum walk so she proudly thrust out her chin as the shiny sticky residue on her skin glistened under the cinema's lamps, and stunned workers did a double take as they watched her walk past. When they were outside Chester finally wiped up the spare cum with his thumb, then offered his outstretched finger to Tessa who eagerly sucked it clean. They shared another long kiss as Tessa jumped up into his arms and he groped her bare butt cheeks as he gripped them beneath her coat, and then they set out back into the night. They ended up strolling around town for another couple of hours, enjoying each other's company and easy conversation, and eventually they had looped around back around to Tessa's road. 'Well...' Chester slowed to a stop at the bottom of the driveway and smiled, 'that was fun.' Tessa grinned. 'Yeah, it really was. I'd invite you in, but Jaz will be back by now, and...' Chester nodded and shrugged. 'Yeah don't worry, it's fine.' 'Ok, cool. Oh yeah, you need this back.' Tessa glanced at her house to make sure all the windows were still dark as she unbuttoned Chester's coat, and he laughed nervously. 'Don't be silly, you can keep it, you don't need to give it to me right now. I'll come and pick it up from you some other time.' Tessa had finished unfastening the jacket, and without any hesitation she slipped it off her shoulders and held it out for Chester to take. 'No, you'll be cold! I won't let you walk home without it. Seriously, take it.' 'Jesus Tess...' Chester didn't take his eyes off her as he let Tessa's stubbornness win, and reluctantly pulled on his coat and then leant down to her for one final kiss. Tessa wrapped her arms around his back as their lips met, and he reached down to cheekily grab her butt as they made out. Eventually they broke off, and Tessa smiled sadly up at him, she never wanted tonight to end, she could do this forever. At the same time though she felt like they'd had the perfect evening together so far, and ultimately he was still Jasmine's boyfriend for now, so she felt that going any further might be a step too far. 'Goodnight Chester.' She stepped away and sauntered slowly up the path, looking back over her shoulder as she watched him stare lustfully after her. 'Goodnight Tess...' With a heavy heart Chester finally tore his gaze away and headed off into the dark. Tessa fished out the spare set of keys that her family kept hidden in the plant pot by the front door, then headed inside and went straight into the kitchen. She poured out a glass of water and gulped it down, finally washing away the not unwelcome taste of Chester's cum from her mouth with had been lingering on her tongue since the cinema. She yawned as the adrenaline from her evening's exploits began to wear off, so she headed upstairs and accidentally walked straight into her dad. 'Shit!' 'Jesus! Err, Jasmine?' Her father immediately averted his eyes skywards as Tessa awkwardly covered herself up with her hands and stood squirming on the upstairs landing. Luckily she still had her wig on, so her dad had misidentified her as her sister. 'What are you doing?' Tessa blushed, even though her disguise was still working this was still incredibly awkward. 'Sorry dad, I was thirsty and I just went to the kitchen to get a drink, I thought everyone was asleep...' Her father sighed as he continued to study the ceiling. 'Right, well maybe put some clothes on when you're out of your room, ok sweetie? Just incase.' 'Yeah, of course, sorry. Umm, night then. Sorry again.' 'Yes, goodnight Jaz.' Tessa nervously shuffled past him as she headed towards her room. 'And umm, dad? Could you not tell mum about this?' Her father had already turned to walk the down the hall to the bathroom. 'I won't, don't worry. See you tomorrow.' 'Thanks...' The chastened and genuinely mortified Tessa watched him disappear through the doorway and then scampered back to her room, and she collapsed onto her bed with a sigh. She pulled the duvet over her goosebump covered skin, then started to laugh uncontrollably into her pillow as she reflected on how ridiculous that night had been. Even taking that last second embarrassment into consideration, that had still been the best day of her life, by an absolute mile. ***** The next afternoon a very naked Tessa was masturbating again as she read another of ThanksForAllTheFish's magnificent stories, one about a couple who cured their lock down boredom by becoming amateur exhibitionists, when their naughty antics gave her another bad idea. She kept her vibrator working away on her clit as she opened her phone with her free hand and texted Chester. 'Hey, you still haven't confronted Jaz about Patrick right?' He replied quickly. 'No, I still haven't seen her, I think if I even message her I'll just flip and get pissed off.' 'Ok, so you two are still meant to be going to the festival this Friday?' Every year the next town over had a big concert thing in a field, where pretty well known bands from across the county would gather for three days of live music. It was very popular, to the point that sadly Tessa and her friend group hadn't been able to get tickets for this weekend. However she knew Jasmine and her mates had been more lucky, and she was meant to be going with Chester. 'Oh, well I still have the tickets if that's what you mean.' Tessa smiled, this was all she needed to know. 'Nice. In that case I know how we can get back at her.' 'Oh yeah?' 'Yeah... here's the plan.' ***** The next morning the Conolly family were discussing what everyone's plans were for the day, and Jasmine was telling her parents about the festival that she was attending that afternoon. Tessa smiled quietly to herself as she listened to her sister's enthusiasm, and then surprised her with a kind offer. 'Hey Jaz, I'm going to Maya's for the day, so I could drive you to the station on the way if you want?' Jasmine was a bit taken aback, seeing as she had been a total dick to Tessa over the last week or so, but she wasn't about to turn down a free lift. 'Oh that would be great Tess, if you don't mind, thanks!' Tessa smiled. 'Sure, it's no problem.' A few hours later Jasmine, now dressed in her flamboyant festival outfit, was being driven towards the station by Tessa, who swore as they ran over a pot hole in the road. 'Shit...' She pulled over the side and put on the hazard lights. 'Jaz I think that might have just blown out our tire... the steering's gone wonky. Can you check the left wheel, at the back? See if there's a puncture?' 'Err yeah, sure.' Jasmine put her phone on the dashboard and unclipped her seat belt, then climbed out of the car as she went to go and examine the extent of the fabricated damage. As soon as she was standing on the grassy verge Tessa leant over and quickly pulled the passenger door shut, then hit the lock button as Jasmine turned around to look at her with confusion. 'Hey Tess, what the... what are you doing?' She tapped on the glass irritably and Tessa buzzed down the window just enough so that they could hear each other clearly. 'Yeah change of plans, I'm not dropping you off at all, I'm just going to leave you here.' Jasmine didn't know if she was more angry or confused, to her knowledge she had done nothing to deserve this. 'What the hell? Why? Just let me in!' Tessa shook her head gleefully, it turns out that revenge does indeed taste sweet. 'Bye now, enjoy your walk home!' 'Tessa! You have my phone! Hey!' Jasmine's screams faded away as Tessa waved her goodbye and sped off back along the highway towards the station. On the platform she met Chester and they hugged excitedly, so far the plan was going well. It would take Jasmine a couple of hours to trek back to the house, and by then Tessa would be having a great time posing as her replacement at the festival. She held Chester's hand as they boarded the train and took their seats to begin the twenty minute journey to the next town along, where the rest of their group were waiting. As they pulled away from the station Chester turned to look judgingly at Tessa's plain t-shirt and leggings. 'So, is this what you're wearing today? It's not very festivaly...' Tessa slapped his arm playfully. 'No silly, I've got a change of clothes in my bag here. I logged onto Jasmine's amazon account and found out what she'd ordered, so I've got an exact copy of her outfit. You know, just incase she'd already told her girlfriends what she was going to wear already.' Chester was impressed. 'Oh, very sneaky... so what, you need to get changed before you see them at the next stop?' Tessa raised her eyebrows suggestively. 'Yeah...' 'Ok, are you going to go use the bathroom then?' Tessa rolled her eyes. 'Eww, the ones on these trains? No way, they're disgusting. Here should be more than fine, now hold this please....' 'Wait, what are you doing...' Chester looked on dumbfounded as Tessa shoved her bag onto his lap, making him wince slightly, and then with an excited glance around she leant down and started undoing her trainers. She looked up with him as she fiddled with the laces and chuckled. 'Huh? I told you, I'm getting changed.' Their train was absolutely rammed as everyone was heading to the same destination, and every seat was taken up by young festival goers dressed in flamboyant outfit. Around the doors people were having to stand up, but where they were in the middle of the carriage no one was blocking the aisle. However there was still a couple across them to their left, not to mention the people who were sitting behind them, so it really wasn't a safe place to get changed at all. Chester gulped nervously and whispered down to this crazy girl. 'Tess, there's no way you can do this without being seen!' 'Chester relax, it's fine.' Tessa put her shoes under her chair and then quickly stripped off her leggings, peeling them down her legs and balling them up before shoving them into the bag. Chester got a quick glimpse in between her thighs and his eyes widened.