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Chapter 17
by
Funtimes
What my dear?
I up the ante
The handoff caught me off-guard, but I recovered. “Truth or dare, Wiley.”
“Truth,” he said, spitting out the answer before I’d even finished the question. He did not trust me with anything else.
I tried to keep my expression innocent. “Did you like seeing my girlfriend’s tits?” The question hit him like a bucket of cold water, and for a moment I thought he was going to throw his drink at me, or at least at the expensive area rug Sarah’s mom had given us for Christmas.
Wiley’s eyes darted wildly, looking for a loophole, but Sarah—always the quick study—beat him to it. She leaned over, and her hair swept the side of his cheek. In the barest whisper, she said, “If you don’t want to answer, your punishment is to tell us the answer anyway.” She grinned at me with her secret weapon smile, the one she used when she wanted to break all the rules at once.
Wiley groaned, burying his face in his hands. “Fuck me,” he muttered. He looked up, squinting at me through his fingers. “Fine. Okay. Yes. I did. Just don’t shoot me.”
I laughed out loud, releasing some tension in the room. “I won’t.” I caught Sarah’s eye, and she rewarded me with a mock salute.
“Liam, it’s your turn again,” Sarah said, as if she were a game show host on speed.
Wiley looked up, his cheeks a dull red. “Wait. It’s supposed to be my turn.”
Sarah patted his knee with a breezy, dismissive gesture. “No, you lost your turn because you had to do a punishment. That’s how the game works.”
Wiley glared at her, but then relented with a grudging, “Fine. Whatever.”
I turned to Sarah, pitch-perfect in my best ‘serious boyfriend’ voice: “Truth or dare, Sarah?”
Sarah rolled her eyes with practiced theatricality. “You better dare me to do what I’m thinking of,” she said, and that made Wiley snap his gaze over to her, interest piqued despite himself.
I played along. “I dare you to take your shirt off.”
Wiley sputtered. “Wait, what?”
Sarah reached for her buttons, but I caught her wrist with my fingertips, just to draw out the moment and watch Wiley’s brain overload with anticipation. “For speaking out of turn,” I said, “I think he loses his next turn, don’t you?”
Sarah’s eyes glittered with mischief. She pulled her blouse loose in one practiced movement, the fabric slipping over her shoulders, her bra the only thing left between us and bare skin. She didn’t hesitate, not even for decency’s sake, just unclipped and let it fall to the floor.
Her nipples were instantly taut, the cool air raising goosebumps along her arms and across her chest. She didn’t cover herself; she didn’t even blink. She just met Wiley’s gaze head-on, daring him to make a joke or a complaint or even a sound. For all his bluster, Wiley was silent.
Sarah leaned back, stretching as if she were on the cover of a swimsuit catalog, then settled in, perfectly composed, wine glass raised. “Yes, of course,” she said, her voice the picture of satisfaction.
If the silence had a temperature, it would have been absolute zero. Wiley tried not to stare. He failed. He stared.
I didn’t bother hiding my own reaction either. This was, after all, the point of the exercise.
Wiley finally managed, “I don’t see how that’s fair.”
Sarah’s lips curled in a wry smile. “Welcome to adulthood, Wiley. Nothing’s fair.”
He coughed, searching for leverage. “Then what’s next? You want me to drop my pants in front of both of you?” There was a note of challenge in his voice, but also the defensive air of a man who knows he’s three moves behind.
Sarah considered this, tapping her finger on her chin. “Maybe. In fact I dare you to do just that!”
Wiley “Wait I wanted to pick truth.”
Sarah “My tits are out, I think we are well past picking truth.”
He does as he ask and quickly cross his legs so no one could she is small hard cock.
She exhaled, content, and turned to me. “Your move,” she said.
Wiley groaned. “You skipped me again!”
“Punishments take precedence over turns,” Sarah replied, swirling her wine. “You agreed to the rules.”
She was right. He had.
For a second, Wiley was frozen, pants bunched at his knees, eyes flickering between my face and Sarah's bare skin, as if by staring too long at either he might combust. Even then, he tried for dignity: he drew himself up, plucked his glass from the table and sipped, only to sputter as Sarah shifted beside him, her legs long and pale and completely exposed. It wasn't lost on either of us that the only person here who had yet to truly commit to the game was me—but the way Sarah had elevated the stakes.
“Sarah, I don’t think he should be the only one not wearing anything on his legs, I dare you to take of your skirt.” She does, we both think she was going to leave her thong on, but she step out of it with out hesitation too, so that she was now sitting next to him completely naked.
Sarah made a show of considering her next words, propping her chin on her fist. “Wiley I dare you to tell me if you like what you see?”
He managed a strangled sound, halfway between a laugh and a cough. "Sarah, you’re like family. You know that. And I really don’t want to die" But his voice betrayed him, and the three of us heard it at the same time: that little edge of longing, the truth leaking out despite his best efforts. He looked at me for help, but I was enjoying this far too much to intervene.
Sarah “Fine if you don’t answer, the punishment is for Laim to beat you up until you answer.”
Wiley groan “Fine… fine… just don’t hurt me. Yes Sarah I have fucked you… and you’re the only woman I have ever fucked. SO YES, I LOVE EVERYTHING I SEE!” The room goes silent for a second before he says “Let me just I lost my turn again”
"That wasn't so hard," Sarah said, grinning. She nudged him with her shoulder, and he nearly spilled his drink.
“You assholes.”
Sarah winks at me tell me she was ready for my next dare “If you think we are asshole just wait until hear Liam next dare.”
“Wiley since you love everything you see so much, I dare you to fuck my girlfriend right here and now!”
Wiley froze, his wine glass suspended halfway to his mouth. His eyes darted between Sarah and me, searching for the trap, the punch line, the moment when we'd both start laughing at him.
"You're kidding," he said finally, his voice cracking on the second word.
Sarah shifted beside him, her nakedness suddenly more deliberate, more pointed. She looked at me with a mixture of pride and hunger that made my chest tighten.
"He's not kidding," she said softly. Her hand reached out, fingers brushing against Wiley's trembling knee.
Wiley nervously glance at me as if he was scared to ****, I might kill him “What the punishment if I don’t”
Sarah laughs “First I’ll be insulted, and then he will hold you down as I slide my wet pussy up and down on your cock.”
Wiley's face paled, his mouth hanging open in shock. He looked frantically between us, searching for any hint that this was an elaborate prank.
"I don't understand," he stammered. "Is this some kind of sick joke? Are you trying to humiliate me again?"
I shook my head slowly. "No joke. No humiliation."
Sarah slid closer to him, her naked body now pressed against his side. "Remember how you said I was the only woman you've ever been with? Well, it turns out..." She glanced at me, a silent communication passing between us. "It turns out Liam likes watching us together."
Wiley's eyes widened. "That's... that's fucked up."
"Maybe," I conceded with a shrug. "But it's the truth."
"So, all those times..." Wiley's voice trailed off as realization dawned on him. "You weren't just putting up with it because of your job?"
I leaned forward, elbows on my knees. "The first time, I was angry. The second time, I was confused. By the third time..." I paused, searching for the right words. "By the third time, I knew I wanted it to happen again."
Sarah's hand moved to Wiley's thigh, inching higher. "So what's it going to be, Wiley? Are you going to take the dare, or the punishment?"
Wiley swallowed hard, his Adam's apple bobbing nervously. "But he's right there," he whispered, gesturing toward me.
"That's the point," Sarah replied, her voice low and seductive. She placed her palm against his chest, feeling his rapid heartbeat through the thin fabric of his shirt. "He wants to watch. And I want him to watch."
Wiley nervously stood up, his pants still bunched around his knees. "I need a minute," he said, stumbling slightly as he tried to move. "This is too weird."
Sarah caught his wrist before he could escape. "Weird doesn't mean bad," she said gently. "Sometimes weird can be exactly what everyone needs."
I could see Wiley's resistance crumbling as Sarah's fingers traced patterns on his skin. His breathing had become shallow, his pupils dilated with a mixture of fear and desire.
"What if..." he started, then cleared his throat. "What if this ruins everything between us?"
Sarah smiled, a genuine warmth breaking through the seductive facade. "Hasn't that ship already sailed? We crossed that line weeks ago."
Wiley looked at me again, still seeking permission or perhaps reassurance. I nodded slowly, deliberately, letting him see that this wasn't a trap.
"Okay," he finally whispered, the word barely audible.
Sarah's face lit up with triumph. She rose to her knees on the couch, completely uninhibited in her nakedness, and began unbuttoning Wiley's shirt. Her movements were deliberate, almost ceremonial, as she stripped him bare before both of us.
I watched, transfixed, as Sarah guided Wiley down onto the couch. His body was pale and soft compared to hers, but there was something mesmerizing about the contrast. She straddled him, her back arched like a dancer's, her hands splayed across his chest.
"Look at me," she commanded, and Wiley obeyed, his eyes locked on hers as she lowered herself onto him.
The sound he made—half gasp, half moan—sent electricity through my veins. Sarah began to move, setting a rhythm that was neither rushed nor tentative. She knew exactly what she was doing, performing for both of us now.
"Tell him how it feels," I said, my voice husky with arousal.
Sarah turned to look at me, her eyes glazed with pleasure. "It feels... different," she admitted. "Not better, not worse. Just different."
Wiley's hands found her hips, his fingers digging into her flesh as he tried to guide her movements. Sarah shook her head, placing her palms over his.
"Not like that," she murmured. "Like this." She adjusted the angle, the pace, teaching him without words.
I shifted in my seat, my own arousal becoming uncomfortable. Sarah noticed and smiled, reaching out her hand toward me. I took it, allowing her to pull me closer to them.
"Kiss me," she whispered, and I did, our lips meeting in a passionate exchange while Wiley continued to move beneath her.
When we broke apart, Wiley was watching us with an expression of awe and confusion. "This is the strangest thing that's ever happened to me," he said breathlessly.
Sarah laughed, the sound vibrating through all three of us. "Get used to it," she replied, increasing her tempo. "Because if you keep coming back here, this is going to happen again."
Wiley's eyes rolled back as Sarah's movements became more insistent. His hands clutched at her, **** and needy. "Sara-bear I'm close," he warned.
Sarah looked at me, a silent question in her eyes. I nodded, giving her permission to finish what we'd started.
"Let it go," she told Wiley, her voice commanding despite her **** position. "Let it go while he watches."
Wiley's body tensed, his back arching off the couch as he climaxed with a strangled cry. Sarah continued to move, working him through it, her own pleasure building visibly.
When it was over, the three of us remained frozen in tableau—Sarah still straddling Wiley with his cum dripping from her pussy, me kneeling beside them, all of us breathing hard and adjusting to this new reality we'd created.
What's next?
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Can't we let him stay?
It'll only be for a day or two, right?
Finally moving in with his long time girlfriend, their first night together is interrupted by a familiar face who needs a place to stay...
Updated on Jun 1, 2026
by Decadent Empire
Created on May 29, 2023
by triangletoast
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