Ghosts of Halloween: A Dark Why Choose Romance

“Get down on your hands and knees, angel. I want to see it from up close,” I say while gently fingering one of Jack’s piercings. They make him so much more sensitive on top of being sexy as fuck. I can’t resist touching them.

Harlow does as I say, wiggling her butt in our faces. Jack groans and leans closer, putting his hands on her hips. His eyes keep straying to the colorful toy in her ass, and I admit, I like the look, too. Though I’d much rather it were my cock in there.

Maybe I’ll get to fuck Harlow, too. Hopefully, I’ll have enough stamina. Or maybe there’s another way to have both of them.

“Maybe you can fuck her while I fuck you, puppy?” I ask Jack, squeezing him harder. “What do you say?”

“Nngh.” Jack gives me a pleading look, and I laugh.

“Come on, puppy. Use your words.”

“Don’t think I can… handle it. The first time,” he says, and that sobers me up. I rise to my knees, putting my hand on Harlow’s back, the other cupping Jack’s cheek.

“Some other time, then,” I say, leaning closer to give him a gentle kiss. “I want all three of us to fuck together someday. Either way, I can’t wait to fuck you, love.”

Jack shivers, his eyes widening when I call him “love”. I don’t think I’ve done it before, but I feel so generous tonight. So safe.

“You are, you know. Both of you,” I say. When Harlow sits up, looking at me with uncertainty, I kiss her, too. “My loves.”

The door opens and Caden comes in, still gloriously hard. He takes one look at us and smiles warmly. The beard makes him look like a benevolent, albeit very naked and ripped, Santa Claus, and I shake my head in disgust.

“Take it off. It makes you look eighty years older,” I grumble, though, truth is, I just want to see his face. “You, too, Jack. Unless you want me to fuck you so hard, the mask falls off your face. I can do that.”

Jack gives me a startled look and then grins, shifting the stupid reindeer mask so it sits more securely on his head. I narrow my eyes even as lust pounds through my veins. The little brat.

Caden leaves the beard on, too, giving me a taunting grin. I trap a growl behind clenched teeth. Fucking brats with no respect. Luckily, the idea of fucking Jack’s mask off him lifts my mood at once.

“Let’s get you ready so you can take it,” I say softly, my voice making his cock twitch. “On your hands and knees, puppy. Make sure you watch what Caden does to Harlow.”

He’s already got her sitting between his legs, spread wide open. The black box is by his side, but for now, he just uses his hands. He plucks her nipples slowly, mouth at her ear, whispering filth that makes her squirm. I glimpse the festive plug between her wantonly spread legs.

“Want to be our cumslut tonight?” Caden asks her in a low, gritty voice that makes my balls tingle. “You can get all the cum you want, baby girl. But you gotta earn it. Do you know how good girls earn what they want?”

She shakes her head, moaning when his hand dips to her clit, strumming gently. Caden grins and pushes two fingers inside her. “With orgasms. I’ll make you come so many times, love. Until it hurts. You want that?”

She nods so fast, her hair shakes with it. I swallow, cock throbbing impatiently, and grab the lube. For a moment, I wonder if Jack wouldn’t prefer his first time bottoming to be less crowded. Just the two of us. Fuck. I really want him now, though.

“Puppy, you sure about this?” I ask, trailing my fingers down his tanned, beautifully muscled back. “It doesn’t have to be tonight.”

He turns his head, his sensuous lips slightly parted and wet. “I’m sure,” he says, making my gut twist with pleasure. “I want this. I want you.”

I bend low to kiss him, sucking his lower lip into my mouth until he gasps, his hips flexing. I pull back just enough to end the kiss, my lips still touching his. “Perfect. I want you, too, Jack. It will feel so good. I promise.”

He catches my lips in one more kiss before I pull away. Harlow’s moan makes me look over. Caden’s working to make her come with his fingers, keeping her legs open wide. Jack pants, watching, and fuck, maybe this is actually better for him.

He can share this with us all.

I slick my fingers with the lube and get behind him, reaching around his hip to grip his dick before touching his ass. His breath catches, cock throbbing in my fist, and I run my fingertips over his Jacob’s ladder, making him twitch.

“There’s my good boy,” I murmur, touching his hole with my lubed fingers. Jack gasps, and I stroke him slowly. His breaths rush out of him, faster and faster, and his cock is so wet with precum, soon both my hands are slick.

I can’t help looking at Harlow as I slowly prepare him. Caden still hasn’t taken out the massager. I suspect he wants to make her come on his own as a point of honor. She’s almost there, too. Those gifted fingers can’t be resisted.

As my fingertips slowly run round and round Jack’s rim, both he and I stare at Harlow. Her eyes are dazed, nipples hard, chest heaving. She cranes her neck back when Caden’s hand speeds up between her legs, rubbing the sides of her clit with faint, slick sounds. She gasps, moans, and then her body tenses in pleasure.

He doesn’t stop until she slumps against him with a whimper. Caden looks up, eyes satisfied, mouth smirking, and raises his wet fingers to his mouth. Jack’s hole pulses with his arousal, but it’s softer now, more pliant. In the aftermath of Harlow’s orgasm, I slide my finger inside, making his cock buck in my hand.

“All good, puppy?”

“Yeah,” he breathes, moving his hips until my finger sinks in to the knuckle. “Fuck.”

Harlow mewls in annoyance, too blissed out to speak. When I look up, I see it’s because Caden’s still touching her, one hand teasing her oversensitive clit, the other opening the box. A moment later, he takes out the wand massager. It’s the most powerful one he could get, with several settings he’s actually tested out before tonight to know how to play Harlow just right.

He grunts and reaches over to the wall to plug it in. Harlow eyes the toy with horny unease, and that makes me smirk. She likes riding those edges, challenging her limits, giving up control. Caden picked right.

I slowly fuck Jack’s asshole with my finger, stroking his back and hips with my other hand. Soon, I add a second, his cock jerking in my hand as he gives a muffled moan.

“Wanna see stars, puppy?” I ask, angling my hand to touch his prostate. I find it at once, nice and swollen with arousal, and when I press in, Jack chokes on a breath, a powerful tremor running through his body.

“F-fuck. Silas. Fuck,” he says, shaking harder when I run slow, deep circles over the area. “It feels like… Like I’m gonna…”

I stop at once and just fuck him with two fingers. “Such a good puppy,” I murmur, waiting for him to relax so I can add one more. “So handsome and horny. You feel so good inside, love.”

Jack’s breath shudders out of him, sweat beading down his spine as his chest heaves. The sound of vibration jerks my attention away from his glorious body, and we both look at Harlow and Caden. He holds her between his legs, his forearm an iron bar over her ribs as he slowly trails the wand down her left arm.

“Daddy Santa is a fucking tease,” I say when I catch Harlow’s eye. She’s so horny, she’s shaking, her swollen lips parted as she looks at me. She seems tense with almost pain, her brows drawn together, eyes pleading. “Let’s see how many times you come before I’m done with the puppy, hm? I’m betting it’s fewer than ten.”

Caden’s head jerks up, a lusty grin spreading on his face. Harlow shivers, squirming nervously between his legs, but I see it in his eyes. He took the bait.

“What are we betting?” Caden’s voice is so business-like, I grin. I know he’s as hard as steel and panting with lust, but as soon as it comes to gambling with orgasms, he’s suddenly clear-headed.

“If she doesn’t come ten times or more before both me and Jack finish, you’ll never use paprika in Italian again.”

He scoffs and rolls his eyes. “Fine. And if I make her come ten times or more, you’ll never criticize my spice choices.”

I stare at him for a moment, deliberating. There is a faint chance he might win, and some of his cooking ideas are positively atrocious. Not being able to say anything will be fucking annoying. Then again, it’s always more fun with real stakes on the line.

“Fine. I’d shake on that, but I’m kinda busy,” I say, slowly pumping my fingers in and out of Jack’s ass.

“Understandable,” Caden says. And then he presses the wand to Harlow’s clit, making her come almost at once. When her cry of pleasure dies down, he gives me a smug look. “That’s two. Let the better man win, old sport.”

Jack shoots me an uncertain look over his shoulder when I pull my fingers out of his ass. “Silas… You’re not actually gonna…”

I move to the side and kiss him slowly, interrupting him. I know he’s worried I’ll rush it now, possibly hurting him to win, but that’s not how I do things. I want to enjoy it all: him, the sex, and then winning after we both come, fully sated and satisfied.

“Don’t worry, puppy,” I murmur against his lips. “We’ve got plenty of time, and I already promised I would make you feel good.”

Jack relaxes, and I get behind him, pumping more lube in my hand. It’s his first time, and I definitely won’t rush, even if that means I’ll lose my trolling privileges in the kitchen. I hope Caden shows the same consideration to Harlow. We haven’t exactly forced any orgasms on her before.

“If she cries ‘ghost’, you’ll lose, by the way,” I say casually, looking up when I slide my slick fingers inside Jack, making him moan. “So don’t overdo things, old sport.”

He grunts, eyes glittering as he puts the toy away. Instead of reaching between Harlow’s legs again, he runs his hands up her arms and frames her face, his thumbs caressing her cheeks.

“My beautiful, lovely girl,” he says, his voice low with arousal. Goddamn, it even makes me shiver. Harlow doesn’t stand a chance. “I love seeing you like this. You make me so hard, baby girl. Even better, you make me smile every day. You make me feel young, like I have a full life ahead of me. With you, I can play, joke, and have fun. And I love it so much when you let me take care of you. You have no idea how much pleasure that gives me—to bring you gifts, to renovate the house for you, to cook. You bring so much light into my life. Into all our lives.”

She shakes her head, stomach tensing, and I watch it in disbelief, slowly massaging Jack from the inside. It looks like she might actually come from Caden’s words alone. He’s just touching her face, for fuck’s sake.

I fully expect him to give me a triumphant smirk when she moans, leaning heavily into him, her hips undulating with pleasure. But he doesn’t, and that tells me he means every word. It’s not just a means to an end. He wants her to know all of this, and what better time than now?

Harlow doesn’t take compliments easily. She thanks politely but I can tell she never lets them sink in. Now, with a few orgasms in her system, she’s much more open. Her defenses are down, and every word Caden speaks penetrates deep into her.

“All right, puppy?” I murmur, slowly pressing into Jack’s prostate. His breath hitches and he nods frantically, twisting his neck to look at me.

“Please. Fuck me. I can take it.”

My cock jerks at that, and I drag my fingers out. When I grip my prick in my slick fist, my eyelids flutter shut with pleasure. Fuck, oh, fuck. It won’t take long. Still, I want to give Caden a fighting chance.

“Hey, Harlow,” I say, lining myself against Jack’s slick hole. When she looks up, I grin. “I love you.”

Her eyes widen, Caden’s hands shifting down her throat to her collarbones and shoulders. She cants her hips, like she’s chasing friction, though there’s just air for her to hump.

“I love you, too, little bird,” Caden murmurs, lips almost pressed to her ear.

She cries out, tensing further, her body shaking. I wouldn’t believe it if I didn’t see it with my own eyes, but it seems like she’s about to come. From words alone.

“I love you, princess,” Jack says, his voice hoarse.

That does it. With an abrupt, high-pitched shout, she arches off the mattress, pressing back into Cay, and comes. I see the butt plug inside her working just faintly when her muscles tense around it. God, it’s beautiful.

When she collapses between Caden’s legs, her head lolling back onto his shoulder, he grins at me, his eyes twinkling.

“That would be three.”