The Dare, Book 2 - Cover

The Dare, Book 2

Copyright© 2026 by TailWeaver

Chapter 2: Playing Dress Up

True Story Sex Story: Chapter 2: Playing Dress Up - It had been a few months since Talia had stopped letting Peter give her any dares. She could not seem to get him to recreate the feelings she had with Chuck helping her along. Maybe it just wasn't possible. Or maybe she just needed to try again. To say that things were never going to be the same would be the understatement of the year.

Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Consensual   Reluctant   True Story   Incest   Brother   Sister   Group Sex   Anal Sex   Exhibitionism   Masturbation   Oral Sex  

A couple of days passed before Talia wore her bracelet again. She had exchanged a couple of emails with her new writing partner, giving them details, and even told Peter she was doing so. She had started wanting there to be no more secrets between them, hoping to avoid a crash-and-burn like the time before. Again and again, she would read what they wrote, considering their suggestions and thinking about ways to incorporate their dares into what she might do or suggest to Peter. She still wasn’t sure about that side of things. She spent a lot of time trying to figure out which, if any, of these dares really could be done with the way things were.

Saturday had been a quiet morning, Talia sleeping late, but when she had slid her bracelet on after breakfast, knowing Peter would eventually notice, she hoped that more games might be afoot. She had not found any more of Mason’s that seemed doable, but his suggestions did keep her imagination going, and she could feel how pent up she was. She really hoped Peter was getting better and reading her obvious (the bracelet) and not-so-obvious signals.

Peter had not waited too long, hoping that Talia was not already following a dare, before he spoke up. “Since you don’t seem to be in the middle of something, I have an idea for you,” he said, popping his head into her room, watching her typing away on her laptop.

Talia nodded. Of course, the bracelet was the real indication that she was in a game-playing sort of mind.

“Since you told me you wrote all about what had happened before, and you know that I read it too, I want you to come sit on the couch and reread your story - skipping to the parts you love the most if you want. But here’s the dare. If you make a peep, you have to take something off, like the other day during the basketball game. But you are not stopping at your panties this time. And I think buttons can count too, like before. That can draw it out ... assuming you are going to enjoy it as much as I think you are.”

Now, on the one hand, Talia knew she could easily be stubborn and not say a word, but she also knew, before she even agreed to the dare, that she would not. Be stubborn. She wanted to enjoy herself. She wanted an excuse to be looked at. And she loved that he had come up with something that would give her what she wanted. Talia knew she would let herself enjoy the story, and make a noise as often as she dared ... until perhaps she could not help it anymore.

So Talia said ok, went out to the couch, flipped open her laptop, went to her story library, and began reading ‘The Dare’ for what was probably the twentieth time. She was getting engrossed, finding the spot she wanted to read the most, when she heard Peter interrupt her thoughts.

“You are humming. That counts.”

Talia had not even realized it, but true to the letter of the dare, it did count. So she undid a couple of buttons, since she had probably made more than one noise, and felt that delicious tingle that she always felt when she was playing a game or doing a little dare. It was the simplest of things, undoing a button. But doing it, because she was dared to do it, just made it so ... so ... something. She didn’t know what to call it, but it made it delicious and fun.

That seemed to get her going, faster and quicker than the story alone would have, and before much longer she felt like moaning a little as a pulse raced through her hidden sex. She knew she could play this off and be stubbornly quiet, but she knew she wanted this game as much as Peter did. Besides, having someone look at her was so deliciously naughty. She knew part of it was that she felt completely safe with Peter, safe to be daring, to be a little bit naughty.

So another button, and another soon followed, until it was time for her shirt. Talia knew she could switch to her jeans, but she wanted something more first. As she took it off, her shoulders coming free, followed by the rest of her, he spoke up again.

“Oh, and bring me each piece as you take it off. Just to make sure you don’t cheat!”

Smiling, Talia stood up to take her shirt over to him, certain that he just wanted a closer look each time she took something off. It was more than ok with her, as the exposure was as enjoyable to her as the game itself.

Over the next few minutes, more and more ‘oops’ were heard as Talia accidentally made a noise and had to pop a button or undo a snap. She flushed, standing to lower her jeans, glancing at Peter as he watched her remove her pants. Walking over to him, handing him her jeans, she could feel her nipples poking into her bra and almost hurting from her arousal. She knew she was wet, how could she not be, and she did not dare to look and see if it was obvious; she did not want to know if her panties had gotten darkened by her arousal. It would be too much.

She only had two things left to remove, and as she went back to the story, reading about where she had been forced to get seen masturbating, she didn’t even last a minute before she was once again walking over to him, handing him her bra, standing, and letting him look at her rock-hard nipples for a minute.

Now that the only item left was just her panties, Talia could feel him watching her like a hawk the whole time, and she kinda drew it out, being very quiet, but she was in the last chapter, reading some of her absolute most favorite parts, and eventually she had to make a noise. She was wet, so fucking wet, Talia was ready to just play with herself in front of him again, but she stopped, and just stood up slowly and slid her damp panties down.

Talia stood for a moment, quivering, her arousal coursing through her like a raging river. She had been naked in the shower, but this was different. This had been a slow removal of every stitch she had on while reading a naughty story. She had been horny for an hour, it felt like, and she longed to just finish it and get off; she knew it was going to be a good one. Completely naked, she walked over and handed Peter her obviously damp panties. Holding still, she could feel her heart pounding as he looked at her body, knowing by his stare that he was not put off. Knowing that he was enjoying this as much as she was.

“Don’t go yet, read another chapter or something before you, um, turn in,” he said, and Talia just quivered in repressed need as she sat back down, moving the blanket so she could sit on it. At least she could wash the blanket later, she thought, her body quaking on the edge of release, the need to touch herself almost overpowering.


After a most satisfying release, her mouth muffled by her pillow, Talia had felt a bit restless. She went to her laptop, not bothering to get dressed. After the long, slow strip game, she was feeling more and more comfortable being completely naked. She perused what her reader had written, smiling to see that they had come up with another dress-up dare, of sorts, and as she began to think about the specifics and how she might want to execute it, she paused her reading and just thought about everything. Struck by inspiration, Talia opened a new file and began writing.

Saturday Musings Number 1

I want to write things down before I forget exactly how I am feeling. The games are so thrilling, but the awkwardness and pain from when things fell apart before really scare me. I thought if I wrote things down, I guess like a little diary - only a, hmmm, Saturday Diary, well, things might be better. And if nothing else, I can look back and remember why I did what I did.

So, am I really doing this? Playing these games again - with my brother!? It was one thing with Chuck, online and stuff. That was definitely fun. And when the lines blurred, and he forced - well, dared me to act out in front of Peter, the pleasure had been intense. In fact, you know that I’ve never felt ANYTHING like that before. I don’t know if it’s the dares or the wrongness of it all. Something makes my mind and body scream with pleasure like never before. After yesterday’s game and yet another totally satisfying release, I am remembering just how much more alive I felt when I was playing before. And even these simpler dares right now are doing the same thing. I mean ... damn ... I coulda screamed just a few minutes ago, it was so good.

Yes, I am doing this. I want this. So much. I have no idea why this affects me like this. I lived for years with nothing like this happening. Why now? I don’t know. Something got unlocked when ChuckBC blurred the lines between Niki and me. Something woke up, I guess.


It was not an hour after she finished eating that Talia went to her room and laid out what she would wear tomorrow, or maybe Tuesday if it was raining or something. Thinking about the new dare and how she wanted to go, she got everything ready. Considering her choices carefully, already feeling that tingle of anticipation, Talia picked out a rather normal set of undies, and one that was a bit prettier, knowing that Peter would be seeing them, and choosing. She left a space between them and the dress for the invisible third set of underwear, and just stood there for a minute before turning and grabbing her bracelet and putting it on. This dare was not about her clothes. It was to have him choose which set of undies she should wear under her dress.

Talia took a shower and didn’t dry off much. Something about walking around all damp in a towel was hitting the fun center of her mind. She was more than a little damp when she opened the door, and the cool air immediately sent tingles up and down her skin as she adjusted her bracelet (it was sticking a little on her damp skin) and went to look for Peter, finding him in his room reading.

His eyes lit up when he saw his sister in a towel with damp hair. She noticed his gaze on her bracelet and back before smiling at him and simply saying, “So, what’s up?”

She could see him almost smirk, knowing she was playing again, and obviously eager to help. Again. She explained that he needed to help her pick out clothes again, wriggling her bracelet in answer to his questioning look.

Getting to her room and seeing what was laid out, Talia had to explain. “Not the dress, I’m going to wear that. Um, you need to pick out the underwear.” Talia said, holding off on the rest for a second.

He nodded and said, “That’s it? Just pick between those two sets of underwear?”

Talia had to say no, of course. “Um, and I have to put them on and have you make sure it all looks good for work.” She paused again, enjoying the way she was tingling at the idea, drawing it out for her own pleasure. ‘And, um, there’s three sets of underwear to choose from.

He looked again, then back, confused. “Um, where?”

Talia held her breath for a second and nodded at the blank space. “There, um, I guess you could call it an invisible set...”

“Oh ... oh!” he said, looking at her and her flushed face before looking things over again. “I see. And you are...”

Talia twisted her bracelet, nodding, silently telling him she was totally fine with all of this.

“Well, um, and you have to model them to be sure, right?

Talia nodded, certain that he was going to pick the invisible set, but was proven wrong.

 
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