Beck knelt in front of her and cupped her face. “Say the words to him, Kitten. Tell him what you want him to be the first to do.”
My cock leaked even more as I watched her swallow and then meet my gaze. She licked her lips and I felt the motion everywhere.
“I want you to be the first man to…” She hesitated and dropped her head an inch.
“Say the words, Kitten. Show us how naughty you are.”
“I want you to fuck my ass.” Her words were quiet, but they had a massive impact. Her sweet voice speaking such a dirty thing made my head spin.
Beck nodded at me and dropped his eyes to my hand, telling me to get on with it. He was giving me this moment with Winnie, but he still needed to be inside her, too.
When I started pumping my fingers deeper, Beck held Winnie’s face and held her gaze. “Say it louder, Kitten.”
I groaned and eased a third finger inside her tight ass. She needed to be stretched enough that my dick wouldn’t hurt her. I was almost at the end of my ability to hold out, and I didn’t want to hurt her if her ass wasn’t ready for my girth.
“I want you to fuck my ass, Jack.”
Beck growled. “Louder.”
Winnie pushed her hips back into my hand, just as turned on as we were. “I want you to fuck my ass, Jack! Please!”
I lost my clothes in a blink and then slid my cock deep into her core to make sure it was wet before I lined my tip up with her tiny asshole and started pushing inside. As I got the head inside, I stroked Winnie’s ass and then reached around to stroke her clit. “Fuck, baby. You’re so tight.”
Winnie panted and threw her head back as she orgasmed. Her body pulsed around me, and I could feel her heartbeat in her ass. It was wild and unexpected, so much so that I was frozen while experiencing it. I nearly choked when she pushed her ass back, taking more of my length on her own. Her scream of pleasure mixed with my growl.
I slid the rest of my length deep and stayed there, giving her a chance to adjust to my size and myself a chance not to blow right then and there. I looked over her head and saw that Beck was just as shocked as me. Sawyer had the same look of surprise on his face when I glanced at him. None of us had expected her to orgasm while getting fucked in the ass for the first time. Our sweet little Winnie kept surprising us.
“Don’t stop, Jack. Fuck me!”
My dick throbbed. “Ask me nicely.”
She moaned and reached back to find my hand. When I gripped hers and held it against her back, she looked back at me. “Please fuck me, Jack.”
I flashed her my teeth before pulling out of her ass and sliding back in deep. I watched her face and saw nothing but pleasure, so I gave her what she wanted. I stroked in and out faster and faster until the sound of our flesh slapping together filled the room and there was a nonstop symphony of Winnie’s shouts and cries mixing with my own.
Beck laid back on the bed next to us, and I read his mind. I pulled out of Winnie and picked her up to set her down on top of Beck. He wrapped his arms around her and pulled her against his chest as he kissed her. He eased back and looked her over. “Do you think you can take both of us?”
Winnie lifted her hips and slowly sank down on Beck’s dick. She groaned as she finally took him all inside and then looked back at me. “I want to try. I need it. I feel like I’m on fire.”
I moved behind her and stroked her ass. From that close, seeing her pussy stretching around Beck, I wasn’t sure she’d be able to take both of us, but I needed to try. My dick was ready to explode, and I wasn’t doing it anywhere but her ass. “This is a first for me, too, baby.”
Beck nodded. “For me, too, Kitten. No one else could do this for us. It’s only you.”
Sawyer knelt beside us and turned Winnie’s face to him. “You’re so fucking beautiful, Win. Like this, though, you look like a goddess. You deserve to be worshipped. Let Jack into your ass.”
She reached back to spread herself as I nudged her opening. She held Sawyer’s gaze and then surprised us even farther by gripping his dick and stroking it. “I want all three of you. Please, Sawyer.”
I slipped the head of my dick into her ass and swore at the how much tighter it was with Beck inside her. Winnie’s cries of pleasure were soon muffled by Sawyer’s dick sliding deep into her mouth. With her body twisted and filled in every way possible, she braced herself with one hand on Sawyer’s thigh and the other on Beck’s chest.
Forcing the rest of my length into her ass, I gripped her hips hard and tipped my head back. Beck and I found a rhythm almost instantly, like we’d been fucking Winnie together for years. He thrust into her while I pulled out, and I thrust deep while he pulled out. Sawyer tangled his hands in her hair and fucked her mouth while watching everything happening below him.
It didn’t take long for me to reach a boiling point. It seemed to all happen at once. Winnie’s entire body grew tight and flushed bright red as she started to orgasm. Her core tightened like a vise, and Beck shouted. Our thrusts grew uneven until we were driving deep at the same time, fucking Winnie like there was no tomorrow. She screamed around Sawyer’s cock, and her orgasm slammed through her. I shouted her name as I came deep in her ass, pumping my come deep and marking her as mine.
I was barely coherent as I came, but I heard Beck and then Sawyer both come just as hard while Winnie’s orgasm drenched us and the bed below. The way we would make her squirt was fucking hot, and I would fully appreciate it once my brain started firing properly again.
Sawyer sank to the bed next to us, and I eased out of Winnie and collapsed on the other side of Beck. She sank on top of Beck, and we all panted wildly as we came down from what had just happened.
Somehow, we’d crossed even more boundaries than the first time, but it didn’t feel weird. I felt closer to my best friends in that moment and even more connected to Winnie. It was like nothing else would ever feel as good. Or as right.