The Dare
Copyright© 2026 by TailWeaver
Chapter 5: It’s more than a dare now
True Story Sex Story: Chapter 5: It’s more than a dare now - Talia had no idea what kinds of games she would get into as she talked more and more with one of her co-writing role-playing partners. She soon discovered she was more like Niki than she had ever realized.
Caution: This True Story Sex Story contains strong sexual content, including Fa Reluctant True Story Exhibitionism Masturbation Voyeurism Small Breasts
Friday
Logging in as soon as she got home from work, Talia was not surprised to see another note, even though Chuck was also online. Almost immediately, he sent her a text
> >: “Check the note, then let me know when you are ready.”
Talia shook her head, a little amused at his eagerness. And obviously intent to keep things going. Not that she minded. It was all she could do not to drive like crazy on her way home.
Slut.
You did very well yesterday, and I’m sure you had plenty of nice orgasms reliving it all. Time to see if you really are a slut, or just pretending. Strip down to just your bra again, making your nice clothing display, and sit down at your desk with the door wide open. Get some headphones on and wear them, though you don’t need any music (unless you want). Place something reflective near your monitor or laptop so you can see your open door without turning around
Talia took off her clothes almost on autopilot, grabbed her headphones and put them on, then rummaged around for a mirror that would work. She had something in the bathroom that would be perfect, but it would look too obvious. Finally, she found a chrome picture frame that was reflective enough for her to see. As she put it in place, she sat down and began to wonder if she could really do this.
“Ok, I did what you said, headphones and stuff on”.
> >: “Great. I wrote a bunch based on Niki being in the middle of the table surrounded by five hungry guys, so sit back and enjoy this for a bit, let me know when you are done.”
Suddenly, her screen was filled with what looked like 7 or 8, maybe more, paragraphs of roleplay, all told from the various boys’ point of view. As she sat back and read just how slutty Niki was being, she was almost instantly as wet as yesterday, and when she remembered to keep her fingers ‘busy’, she could feel her body aching in response to her touch.
“God, you wrote a lot!”
> >: “What can I say, you inspire me. Both You/Niki, and You/You!”
“I dunno if this is smart, what if they get mad. I mean, I know I’m in my room, but some people are weird about privacy
> >: “You said they’d seen you already, right? Like coming out of the shower or bathroom once or twice?
“Yeah, Talia lied, not wanting to contradict herself. There was no way she could tell him that it was her brother he was threatening to have her flash and not just a roommate.
> >: “Besides, you are going to have your headset on and not turn around. I want to see if they say anything. I am willing to bet they just look in, see that you are listening to music, and either turn away in shock - if nudity REALLY bothers them. Or, more likely, I think they will look for a moment. That’s why you are going to have that mirror. I want to know what they do. OK?”
“Ok, but I swear, if you lose me a roommate!”
> >: “No, I don’t think so, and I can help you get out of being in trouble, that’s why the headphones, etc., deniability.”
“If you’re sure.”
> >: ‘Hmmm, I think part of you likes the thrill. Tell the truth now.”
“Yes.”
> >: “And...?”
“And I’m wet, damn you.”
> >: “Perfect. We will make you a slut yet! Now, tell me what Niki does next and let me know when they arrive, and what happens, ok?”
“Ok.”
The constant nervous tingle that ran through her kept Talia on edge the whole time they returned to their roleplay, culminating in her hearing the front door open.
“Oh, god, they are here. I gotta just pretend to be typing away. SO, don’t pay attention to what I’m saying, ok? OK”
Talia could hear Peter coming down the hall, calling to her, but she pretended her music was on loud and she half-chair-danced as she typed furiously, sending mostly nonsense words over the internet to her captive audience.
She saw Peter’s head duck around the edge of the doorway briefly before disappearing quickly, and she was almost sure that he was going to be an upset, rather than a happy observer. She was about to give up and tell Chuck this was all a big mistake when she saw Peter peeking ever so slowly around the edge of the doorway again, as if unsure if he should be looking. She could see his head, watching her for the longest time, before moving on past her doorway and going to his room.
“OMG, they watched. At first, I mean. I thought they freaked as they ducked away and stuff, but then I could see their head peeking around. Like they didn’t know what to make of me. But they watched me sitting here typing.”
> >: “Perfect, fucking perfect. You are going to be such a happy slut. Now. One more thing, and then we are done for today. Spread your knees wide again so it’s clear you’re not wearing pants, and wait for them to go by, hopefully checking you out again. And if you are really a slut, and not just a pretender, have your hand between your legs at the same time. Not that they could see what you are doing, but they could probably guess where your hand was.
“OH god, you can’t, I mean, shit.”
Talia was torn. She parted her legs a bit, showing off her bare thighs and knees to the doorway, but she couldn’t make herself even pretend to masturbate, not when it was her brother who could be watching. Still, when she saw him watching her for more than a quick second again, she could feel herself getting wetter and wetter the longer he looked at her barely clad body. She knew he could see one bra cup and the side of her bare thigh, but that was probably about it. The fact that her jeans, panties, and shirt were splayed out across her bed had to have let him know she was barely dressed, though. Steeling her nerves, she began to move her hand between her legs, only to see that he had left.
“Oh god. They watched again. For a long time.”
> >: “And did you play with your wet slutty cunt?”
“I was going to, but they left before I could. I swear”
> >: “Too bad, and here I thought you were going to be the best.”
“God, you are such a prick!”
> >: “Yes, I know! But I can also be nice. Hurry up and come, and we can be done. I’m sure you are close.
“God, right now? Like this?”
> >: “Yep, better hope they don’t come back by. Or just be quick!”
“Oh god, I am fucking close. God ... I can’t believe you are making me do this!!!”
Talia worked herself over feverishly, her orgasm so close that it did not take her more than a minute at the most. As she shuddered and came, she glanced at the door in the chrome mirror, unsure if she had seen any movement. There was no one there now, that was for sure.
Saturday
The next day, Talia was a bit surprised not to find a note. But Chuck was there again, eager as always.
> >: “Sorry, no note for you slut, I needed to talk to you first.”
“Oh, ok, um ... what?”
> >: “Are you still ok with this? You know what’s coming next, right? I just wanted to be sure, one last time. You do enjoy being my slut, right?”
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