Maya Is Dared to Do More on Chat!

Late on Wednesday night, midway through her college's spring break week, Maya was not exactly bored, but definitely felt like she should be doing something more exciting than playing video games with Tyler, her annoying step-brother. Unable, or more accurately, unwilling to burn through her limited supply of money by going to some beach town with her friends, she'd spent much of her vacation working on a paper for her sociology course, helping her Mom around the house and, as much as possible, avoiding Tyler; at 19 he was a full year older than she was, but he was far less mature. Maya was pretty sure he'd been trying to find a way to sneak a look at her when she was taking a shower or getting dressed, one more reason to be looking forward to getting back to school!

Anna, Maya's Mom and Jeff, her stepfather, had returned from their dinner out more than an hour ago. Being early risers, they were already in bed by 11:00 so Maya was more or less stuck hanging out with Tyler. Spending time with him wasn't thrilling, but she actually enjoyed the game they were playing, and it was a rare thing they could do together without arguing. A little after Midnight she reminded him he had to be at work by 7:00 AM. She had meant the reminder as a helpful hint, but he took it as just one more example of her treating him like a child. Despite feeling insulted, he knew she had a point and didn't argue; he went up to his room. His bedroom light was off before 12:45.

Not even slightly sleepy and with nothing better to do, Maya went up to her bedroom and changed into her mismatched but comfortable sleepwear. She picked up her phone and started scrolling through her various social media accounts. It took her less than 15 minutes to tire of seeing photos of her friends having more fun than she was having. Looking to have some conversation without disturbing her sleeping family she switched to a text-based chat website to see if she might find someone to joke with, or argue with, anything but doing more work on the damned paper.

Her randomly matched chat partners soon proved to be a bit too random, providing no interesting conversations and more than a few completely uncommunicative partners. "Maybe they just fell asleep," Maya guessed. She added a few tags to both narrow the pool her matches were drawn from and make them more provocative. The terms "amateur fuck," "threesome," and "forced to strip," predictably enough overshot her goal for slightly spicing up the interests of her matches. She couldn't get the replies off her screen fast enough!

Deciding that manipulating her tags just needed to be done more thoughtfully, she decided to try using a few tags closer to things her circle of friends might actually do, or even had already done. The terms "blowjob" and "teasing" produced matches slightly less porny than the earlier batch, but still mostly returned responses focused on their author's level of hornyness. Her last try to find an entertaining conversation, "dares" showed promise; the first couple of responses actually sounded interesting, but were cut short by her partners. The third response started well, or at least not crudely, "Hi, 19 year old Female here."

Intrigued, Maya responded, "Hi, I'm Female too, 18 year old," quickly adding, "What has you up late?"

"Lol," her partner replied, "not so late here, 10:15 PM. What time do you have there?"

"1:15 AM," Maya answered, "Can I have your name?"

"I'm Reese; about your tag, was telling you my name my first dare?"

"Lol, Just like to be polite. I'm Maya, by the way. Are you actually interested in doing some dares?"

"Well, possibly," Reese replied, "we got matched because I've got my dare tag on too, you know!"

"Great," Maya answered,"It's been a long time since my girlfriends and I have played, do you want to set any limits before we start? What do you and your friends usually do?"

"It's been a while for me too," Reese replied, "I can't say that we have any 'typical' game, it really varies depending on the people involved."

"Gotcha," Maya answered, "What would you say was the craziest dare anyone in your group has done?"

"Oh, that's easy," Reese answered, "One girl was dared to run to the end of her block and back in nothing but her panties, in the middle of the afternoon, and she did!"

"Were you that girl?"

Pausing a moment, Reese finally answered, "We're all anonymous here, so I guess there's no harm in telling you. Yes!"

"Sounds exciting!"

"Have to admit, it was!" Reese replied. "How about your group, how extreme do you all get?"

"Most of the time it's fairly basic stuff," Maya replied, "but one night when no parents were around and we'd had a few White Claws one girl accepted a dare to stand in front of the big window in her living room, stark naked, for five minutes!"

"Wow, completely nude? That's seriously hot," Reese replied. "Pardon my being nosy, was it you in the window?"

Reese's screen didn't change for over two minutes, prompting her to send a query, "Still there?"

"Yeah, I'm here," Maya replied, "and yes, it was me, but the truth is, I bargained with the girl who gave me the dare to cut it down to just two minutes!"

Still, I'm guessing 'just two minutes' must have felt like a lot longer than that?"

"It felt like time was standing still, to be honest." Maya replied, "it was embarrassing, scary, exciting, and some other feelings better left unsaid! I did half the time facing out to the street and the other half with my back to the window. I thought turning my back to the street would be easier, but not even knowing for sure if anyone was out there was actually worse. Fuck, why am I telling you all this?"

"You seem pretty brave," Reese replied, "Have you ever turned down a dare?"

"Yeah, absolutely," Maya answered, "Not about to flash my step-brother!"

Reese asked, "Is he good looking?"

"I guess so, Maya replied, but he's kind of a jerk, so the idea makes my skin crawl! How about you, anyone ever give you an unacceptable dare?"

"Oh, sorry," Reese replied, "Yeah, during my first month in college, we were playing in a mixed gendered game. Everyone was making pretty mild dares, nothing more challenging than kissing someone or flashing a bra. Out of nowhere some guy I'd just met dared me to go outside and pee on the sidewalk! Told him I wasn't that kind of girl and blocked him!"

"Maya replied, Good to know you understand the importance of some limits, lol!"

"Says Miss nude in the window," Reese replied.

"Let's make that particular dare off limits for tonight," Maya proposed.

"Deal," Reese agreed, "but does this mean you're ruling out any and all dares involving nudity?"

"Ummmm, probably," Maya answered, "at least none in anywhere near as bright a space as that other time, and not if I'd be certain of being seen naked! Based on some looks the dad in the family across the street gave me later, I'm pretty sure one guy saw me that night, but I'll never know for certain."

Reese asked, "If you thought nobody had seen you on display in the window, would you have been relieved or disappointed?"

Maya was more glad than ever this chat was text only, she knew her blushing would give her away right now. She replied, "No comment!"

Reese persisted, "Aw, you can tell me!"

Maya gave in, saying, "Ok, ok, relieved. Mostly."

Reese kept probing, asking, "So, like 51% relieved, 49% disappointed, or maybe the reverse?"

"Seriously, no comment," Maya replied.

Sensing further prodding wasn't welcome, Reese apologized, "Sorry, forget I asked. Not judging!"

"LOL," Maya replied, "you're DEFINITELY judging right now! But that's what I get for telling you about my crazy side!"

"Honestly, not SO crazy," Reese said, "You had some fun and weren't harming anyone, and I'd bet most people wouldn't have it in them to be as daring as you!"

"Thanks," Maya typed.

"So," Reese asked, "we've established that you're a good performer of dares other people give you, what's the craziest dare you've given to somebody?"

"To be honest," Maya confessed, "my friends generally opt for a truth because I often choke and give them boring dares."

"Wow," Reese asked, " Wow, you do these wild dares yourself and then go easy on the other players?

Not really intentional on my part, but yeah," Maya replied, "I usually end up giving easy dares because I just ask for another person to do the first thing that pops into my head! Giving weak dares is embarrassing all by itself. One time I dared a girl to kiss the person to her left -- perfectly respectable dare, right?"

"Sure," Reese replied, "I've been on both ends of that exact same dare, what's wrong with that?"

"Well, in this case the person she was supposed to kiss was her boyfriend! Not so daring! A lot of the time I just pass to let the other players keep the game interesting."

"I'm so tempted to give you a dare right now," Reese said, "expecting you to not demand anything too daring in return!"

"Are you as good at giving dares as I am bad," Maya asked, "or just average?"

"I can't claim to be specially skilled at crafting dares," Reese replied, "but I definitely am happier coming up with them than performing them!"

Maya replied, "You seem like a thoughtful enough person, so if you're more comfortable giving me dares than having me give them to you, I can live with that, with a couple of limitations.

"What limitations?" Reese asked, fearing they might make the game so bland it wouldn't be worth playing!

"Nothing involving anyone in my family," Maya insisted, "and I can hide, cover up or hit 'pause' any time I need to!"

"Sure, that almost goes without saying," Is there anything else? I want to be sure you're comfortable."

Maya replied, "But not totally comfortable; I mean, it's no fun if you don't push beyond your comfort zone, at least a little bit, right?"

"As you wish!" Reese answered. "I guess before we start I just need to know what sort of setting you're in, who, if anyone, is nearby, what's the weather like, and of course, what are you wearing?

Feeling a slight chill as she heard Reese's request for information, Maya paused a moment but answered:

"I'm at home with my parents, and the step-brother I mentioned.

It's a two story house in a pretty typical suburban neighborhood.

According to my phone it's 68 degrees out, with a few clouds.

I'm currently wearing a worn out white t-shirt, plain black panties with lace trim at the waistband, white pajama pants with big colored polka dots, pink Adidas sneakers, and white ankle socks!

"Great," Reese replied, "but can I also get at least a basic idea of what you look like?"

"Um, sure, I guess," Maya answered, "I'm 5'-8", with long-ish brown hair, brown eyes, 135 lbs, fairly fit, 36C bra size. Does that matter for giving me dares?"

"Thanks," Reese replied, "and no, a description of your appearance isn't critical, but with just a text chat, I like to be able to visualize how things are going. Don't worry, I won't be perving on the image in my mind! Are you good to go?

"Yes, ready," Maya answered.

Reese issued Maya her first dare: "I dare you to leave your bedroom and go to a different unoccupied room."

Thinking Reese wasn't looking to be any better at giving challenging dares than she was, Maya replied, "as far as I know everyone else is already settled in, maybe asleep already, so any room I go to downstairs will be unoccupied."

"Ground floor sounds good; let me know when you're down there," Reese said.

"Downstairs, sitting on sofa," Maya reported a few seconds later. "Must admit, already a little strange."

"You wouldn't normally be dressed like this down there?" Reese asked.

"If I expected to come downstairs, I'd have put on a more opaque shirt. My nipples like to make themselves known in a shirt like this," Maya explained, "and I'm usually in my room for the night when I'm getting ready for bed."

"Uncomfortable yet?"

"Nah, just a little strange," Maya answered, "normally I wouldn't be doing dares here with family in the house

"Okay, if nobody has noticed you going down there, lets go to the front door."

"Why, oh, wait, shit," Maya replied, "are you making me go outside?"

"Yes, why not" Reese answered, "You're well covered, and I haven't even so much as hinted at daring you to take anything off! Let's go!"

"Okay, okay," Maya stopped protesting but made a request, "since my shirt is so thin, can I put a sweater on before I go out? And some sneakers?" She described to Reese a long cream colored, sweater, coat length with a matching knit belt.

"Sure, whatever," Reese grumbled, "but compared to standing naked in a window, I'd say I've been taking it easy on you so far! Anyway, once you're outside, tell me if you see any houses with all their lights off."

Less than a minute later Reese saw Maya's report on her phone. "Across the street I see five dark houses; two to my left and three to my right. There might be some on my side of the street too, but I can't tell without going out to the street!"

"Then go out to the middle of the street and tell me about what's going on at your side!"

Even fully covered, Maya was self conscious standing in the middle of the road in her odd outfit, but she dutifully did as she was told, reporting back to Reese, "Four more with no lights on to my left, and two more to the right. Can I please go back to my house now?"

"No, not yet," Reese insisted, "If all I have you do is go out in the street and report on your neighbor's lighting usage, well that would be a pretty boring dare session, don't you think?"

Maya had to agree, and asked, "What do you want me to do then?" As soon as she asked, the open-ended nature of her request sent a shiver up her spine, but so far Reese hadn't asked her to do anything extreme, so she wasn't too worried.

"Staying on the street, go to the closest dark house to the right," Reese told Maya, "and tell me when you're right in front of it."

"It took Maya a couple of minutes to reach the quiet Colonial house, the third one down from hers on her side. Once she was standing in front of it, she checked in; "Okay, I'm here, looking at a dark house.

"Okay," Reese replied less than a minute later, "find someplace along the front of the house suitable for hiding a small item, like the size of a shoebox. Let me know when you've found it!"

Maya started looking, working her way from the street in toward the house. Even though the property had a lot of shrubs and small trees, she didn't find anywhere not visible from the street until she was practically at the front door, where she found space behind a low stone wall surrounding a planting bed. The wood chips behind the wall topped out 6 inches or so lower than the top of the stone wall. Eager to get this portion of her dare over with before someone came to the door and asked her what she was doing lurking around his house, she told Reese, "I found a good space, what's next?" She instantly kicked herself for giving yet another open ended opening to Reese, but there was no way to retract the request for her next task.

Reese answered immediately, Take your pajama pants off, fold them neatly and put them in the spot you found. Then go back to the street."

"Ahhh, fuuckk," Maya whispered, "What the fuck am I doing?" She sighed and folded them more neatly than they'd ever be in her dresser drawer, put the pants in the hiding spot, then replied to Reese, "Done."

"Excellent," Reese's reply started. "Now, go to the nearest dark house to your current location on the opposite side of the street and tell me when you're there."

The house meeting Reese's requirements was almost directly across the street, so it took Maya just half a minute to be at the curb in front of it. "I'm here," she told Reese.

"Just like at the last house, find a spot hidden from the street somewhere in front of this house," Reese instructed.

"Okayyyyy," Maya replied, not bothering to correct her increasingly ragged texting. She was relieved that she didn't need to get close to the house, finding a tree with a nice thick trunk in the middle of the yard. "Found a good spot, behind a tree," she reported.

"Okay," Reese replied, "Take off your shirt, fold it up and hide it behind the tree!"

"Ahhh, Jesus, Reese," Maya replied, "you remember I don't have anything on under the shirt, right?". After waiting in vain for at least a minute for Reese to propose a less extreme step, Maya gave in. She tried to wrestle her t-shirt off without having to take her sweater off first, but the shirt was too tight and not stretchy enough to satisfy Reese's direction without removing her sweater first. "Have to take sweater off to get shirt off," she explained to Reese, "I'd be standing in stranger's yard, almost naked!"

Reese's response was succinct, "So?"

Maya stared at her phone blankly for a while, then typed, "okkaay, but wtf?" Since Reese hadn't specified where she was to get her shirt off, Maya picked a spot between the two cars in the driveway. She untied the sweater's belt, slipped the sweater off her shoulders, grabbed it as it slid down her arms and draped it on the roof of one of the cars. She grabbed the hem of the ancient shirt, pulled it up over her head, and off her arms. She started folding it, as instructed, on her way back to the tree, but had to stop folding and start over when she saw that it was inside out. She was so focused on readying the shirt for its hiding place she didn't think at first about how little she was still wearing. Once she noticed her current outfit was just sneakers, socks, and panties she hurried to get back into her sweater!

"Done." Maya replied, not asking for further instructions, half hoping Reese was done with her. "And just so you know, sweater was never meant to be worn without a top!"

"Oh, boobs on view?" Reese replied.

"Noo, Maya replied, "but serious amt of cleavage is!"

Reese replied, "You're doing great, hang in there! Are the mailboxes on this street by the road or on the houses?"

"On the houses, usually next to the front door," Maya answered.

"Good," Reese replied, "Go to the mailbox at the next house and put your sneakers in it!"

"Further from my house?" Maya asked, "If so, could be problem. Lights still on there!"

"Then duck down and be quiet," Reese replied.

She was thankful Reese's latest instruction didn't make her expose any more of her body, but Maya cringed when she was nearing the mailbox and heard voices coming from inside the house! She silently cursed her habit of always tightly double-knotting her shoelaces as she fumbled with untying them. Still working on the second shoe, she looked at the door every so often, and saw a man walking upstairs no more than eight feet from where she was hunched over! Once she deposited her shoes in the mailbox she bolted back away from the house and reported to Reese, "Done!"

"Okay, now go to the next dark house and put your socks in its mailbox," Reese instructed.

"Will do," Maya replied, "FYI after this house only1 left before end of street!"

"Thanks, lights on, or dark?"

"Both dark," Maya answered as soon as she was done slipping her socks off. After she dropped her socks into the mailbox, she strolled back to the street and waited to see what Reese wanted her to do next.

Maya didn't have to wait long. "Go to the next house's garage," Reese instructed her. "Once you're there, take the belt off your sweater, and hang the belt on the garage door's handle!"

"Uhhhm," Maya replied, "without belt, boobs r likely to be visible and panties for sure!"

"Still way less exposed than when you were standing in your window that other time," Reese replied, "I thought you wanted to challenge yourself, possibly test your comfort zone?"

"Yeah, I know, but just feels so...fucking scary dressed like this out on my street, I guess."