Page 69 of Bossing My Holiday

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“That’s it,” I praise as my finger slips fully inside. “You’re doing such a good job, Princess.”

Braxton leans up to kiss her, swallowing her moans as I add a second finger, stretching her carefully just as he did. “You’re so incredible. So perfect. God, Waverly, you don’t even know how wild I am for you,” he breathes against her lips. “So perfect for us.”

I work patiently, adding a third finger only when I’m certain she’s ready. All the while, Braxton maintains a slow, shallow rhythm inside her, keeping her on the edge of pleasure without pushing her over.

When I’m satisfied her ass is ready, I squeeze more lube than I likely need, coat my dick in it, and position the head of my cock against her rear entrance.

“Breathe,” I remind her, and feel her take a deep breath. “Now bear down slightly as I push in.”

The pressure is intense as I begin to enter her, the tight ring of muscle resisting before gradually yielding. I go slowly, giving her time to adjust to each new sensation, watching Braxton watch her face for any sign of discomfort.

“Where are we?” I check.

“Tight. Full. Oh my fucking full,” she gasps. “Don’t stop.”

Jesus. I’m goddamn winded, and I’m not even fully inside of her yet. Brax adjusts her, pulling partially out so it’s easier for her to take, and with that, I press forward until I’m fully seated inside her ass, feeling Braxton’s cock through the thin wall separating us. The sensation is overwhelming—tight, hot, forbidden.

Then Brax slides back in slowly, and we stay still, both inside her.

“Oh my god,” Waverly breathes, her head thrown back against my shoulder. “You’re both... I can feel you both.”

“Does it hurt?”

“A little. But I’m okay.”

I reach down to place the vibrator against her clit again, turning it to its lowest setting. “Now we’re going to fuck you properly.”

We start moving in tandem, finding a rhythm that works for all three of us. When I pull back, Braxton pushes in, ensuring she’s always filled completely. The vibrator adds another layer of sensation, making her cry out with each coordinated thrust. Making us feel it too. It’s unlike anything else I’ve ever experienced. Not in any of the other times we’ve done this.

Or maybe it’s the girl.

“You’re taking us so well,” I praise, watching where our bodies join, the obscene beauty of it. “Such a good girl, taking both your bosses’ cocks at once.”

“Yes,” she moans, her hands planted into Brax’s chest, her dark hair sweaty and draped over her shoulders. “Yes, please, more.”

Braxton groans beneath her, his hands gripping her hips, helping to control our movements. I shut the vibrator off because I can tell by the tense look on his face he’s barely hanging on, and I don’t want him to come. Not yet. It’s too soon.

“Does it feel good?” I demand, though I know the answer. “Tell us how it feels to be filled by both of us.”

I thrust up into the tight, hot, clenching heat of her ass, pumping until my pelvis meets the globes of her cheeks. I give her a smack, and both she and Braxton groan as she clenches. Sweat clings to my forehead, and I push her down so she’s chest to chest with Braxton, her full tits crushing into him. He kisses her, cupping her face and devouring her mouth as his hips piston up into her.

I pull back so I can watch both our cocks sliding in and out of her. So I can see the lewd display and burn it in my memory forever. Her cunt and ass are stretched around our cocks and she’s so wet with it. Not just from the lube. But fucking wet withhow much she loves this. Brax picks up his pace, pumping up into her, his eyes closed and his expression blissed-out.

“Fuck,” he pants, his cheeks flushed and his face sweaty. “Fuck.”

I shift my position and my hands so I can pummel in deeper and faster and harder. So there’s no space between us. It’s messy and loud and dirty as fuck but nothing as ever felt as good as this.

She bounces and moves between us, taking but also fucking us in return.

I bend forward, my chest against her back so I can whisper in her ear. “Is this what our little cock whore wanted? To be dirtied up by her bosses?”

“Yes! So good... I can’t... I’m going to...”

That’s the only warning before she starts to spasm and shake. Her orgasm is spectacular, her body convulsing between us, her inner muscles clenching rhythmically around our cocks. The sensation pushes me toward the edge, my control slipping as her pleasure peaks.

Braxton comes first, his grip on her hips tightening as he thrusts upward, pounding hard three more times, and then with one final thrust, he spills inside her with a guttural groan. The feeling of his release, the pulsing of his cock so close to mine, sends me over the edge as well. I thrust deep, holding myself there as pleasure tears through me, emptying myself inside her with an intensity that leaves me breathless.

For a long moment, none of us moves, joined and sated and panting in the firelight. Then, carefully, I withdraw from her body, helping her lift off of Braxton as well.