He Sees You When You’re Sleeping: A Dark and Steamy Holiday Romance of Obsession and Secrets – Where Desire Meets Danger in the Heart of NYC
He Sees You When You’re Sleeping: Chapter 29

What the hell is going on right now? I just had the best sex of my life, blindfolded, only to discover that the mystery man is actually Jack! Jack rocked my world in ways I didn’t think were possible, and as I try to process what just happened, I also feel sick.

How did he know that I was BlackAsChlo? Did he know all along? Was this some crazy coincidence? Or . . .

“Did you see my face when I was filming? I know I got careless one night and—” I look up into his eyes. “Did you realize it was me then?”

Jack’s eyes widen. He runs a hand through his tousled hair, taking a deep breath before answering. “I . . . I did see your face that night,” he admits, his voice low and husky. “But I wasn’t sure at first. I thought maybe my mind was playing tricks on me.”

“And that’s when you became a subscriber. To see for yourself?”

Jack nods slowly, guilt flashing across his face. “I couldn’t believe it might actually be you. I had to know for sure.”

My stomach churns. “So you’ve known this whole time? Every conversation we’ve had since then, every time we hung out . . . you knew?”

He reaches for my hand, but I pull away. “I’m sorry, I should have said something sooner. You have every right to be mad.”

I should be. I should be furious, right? But why am I not?

I close my eyes, trying to sort through the tangle of emotions swirling inside me. Anger, betrayal, confusion . . . but also a strange sense of relief. And underneath it all, a lingering spark of desire that I can’t quite extinguish.

“I don’t know how to feel,” I admit, my voice barely above a whisper. “Part of me wants to scream at you, but another part . . .”

Jack moves closer, his presence both comforting and unsettling. “Another part what?” he prompts.

I look up at him, really seeing him for the first time. Not just sweet Jack. But sexy as hell, dominant Jack. The man who just gave me earth-shattering pleasure. The person who’s known my deepest secret for weeks.

“Another part of me is glad it’s you,” I confess, the words tumbling out before I can stop them. “I was torn between you—Jack, and WinterWatcher.”

“Torn how?”

“Between good and bad,” I admit. I take a deep breath, trying to gather my thoughts. “You were the safe choice, the sweet guy that rescues kittens from trees and shovels my neighbor’s walkway. But WinterWatcher . . . he represented everything exciting and forbidden. I never thought they could be the same person.”

He smiles softly, a hint of that dominant energy flickering in his eyes. “And now that you know they are?”

“I don’t know,” I whisper, my heart racing. “It’s like two worlds colliding. I’m scared, excited, confused . . . everything at once.”

Jack reaches out, his fingers gently brushing my cheek.

I lean into his touch, despite my better judgment. “But why didn’t you tell me sooner? Why go through with this?” I gesture vaguely at the rumpled sheets, the lingering scent of our passion still heavy in the air.

“Being a masked man was a fantasy of yours,” he reminds me. “My goal,” he lifts the red blindfold and dangles it in front of me, “is to grant you every single fantasy you have.”

His words hang in the air between us, heavy with implication. I search his face, looking for any sign of deception, but all I see is sincerity and desire. My breath catches in my throat as I realize the full weight of what he’s offering.

“Every fantasy?” I whisper, my voice cracking slightly. His proximity is addictive, and I replace myself leaning toward him almost unconsciously, never wanting this to end.

Jack nods, his eyes never leaving mine. “Every single one,” he confirms, his voice low and husky. “I’ve seen your videos, Chloe. I know what you like, what you crave. And I want to give it all to you.”

My heart races as I process his words. The rational part of my brain screams that I should be angry, that I should feel violated. But the part of me that craves excitement, that yearns for the forbidden, is thrumming with hunger.

He turns his head toward my computer. If I remember correctly, you promised your subscribers a viewing with a guest.

I gasp, my eyes widening as I follow Jack’s gaze to my computer. The realization hits me like a tidal wave. I had indeed promised my subscribers a special show with a mystery guest. But I wasn’t being serious. Or was I?

“Oh my god,” I breathe.

Jack’s lips curve into a knowing smirk. “Well, we wouldn’t want to disappoint your loyal fans, would we?”

I swallow hard, my mind racing. This is crazy, right? Completely insane. And yet, the thought of performing with Jack, of sharing our passion with my eager audience, makes it impossible to resist this offer.

“I . . . I don’t know,” I stammer, even as heat pools low in my belly. “We can’t show our faces.”

Jack moves closer, his hand cupping my face gently. “We don’t have to. I think you and I can figure out the lighting, the angle, and the shadows perfectly.”

I take a deep breath, weighing my options. The responsible part of me says this is a bad idea, that I should take some time to process everything that’s happened. But the part of me that craves excitement, that yearns for new experiences, is screaming to take the leap.

“Okay,” I whisper, my voice barely audible. “Let’s do it.”

“That’s my good girl.”

Jesus the man knows how to make me melt.

We spend the next few minutes setting up the camera, adjusting the lighting, and making sure our faces will remain hidden. As we work, I can feel the need building, a delicious tension crackling between us.

Finally, everything is ready. Jack stands behind me, his strong arms wrapped around my waist, as I reach for the button that will start the livestream.

“Ready?” he whispers in my ear.

I nod, taking a deep breath. “Ready.”

As I click the button, I feel a rush of adrenaline. The familiar green light blinks on, signaling that we’re live. I can already see the viewer count climbing rapidly.

“Hello, everyone,” I purr, slipping into my BlackAsChlo persona. “I hope you’re ready for a very special show tonight.”

Jack’s hands slide down my sides, his touch igniting sparks across my skin. I lean back against him, feeling his solid chest pressed against me.

“As promised, I have a special guest with me tonight,” I continue, my voice husky with desire. “Say hello, mystery man.”

“Hello, everyone,” Jack’s deep voice rumbles.

“Tell us something about yourself,” I say with a gasp as his hand caresses my belly.

“I like to watch,” is all he says.

The chat explodes with excited messages, our viewers clearly thrilled by this unexpected development. I scan the comments, grinning at their enthusiasm.

“Oh, they’re definitely ready,” I moan, turning my head to look at Jack. “The question is, are you? Time to be watched rather than watch.”

In response, Jack’s hand slides up to cup my breast, his thumb brushing over my nipple. I gasp, arching into his touch.

“I think that answers your question,” he murmurs, his lips brushing my ear.

We begin our dance, a sensual choreography of touches, kisses, and caresses. Jack’s hands explore my body with a familiarity that still thrills me, knowing now that it’s him—sweet, kind Jack—unleashing this passion.

As we move together, I’m acutely aware of the camera, of the hundreds of eyes watching us. But instead of making me nervous, it only heightens my arousal. I feel powerful, desirable, completely in my element.

“BlackAsChlo has been very very naughty,” Jack says to the viewers. “I’ve promised this naughty girl a punishment, and I’m a man of my word.”

My breath catches in my throat at Jack’s words. The dominant energy I’ve only experienced through a screen is now radiating from him in person, and I want more.

“That’s right,” I purr to the camera, playing my part. “I’ve been such a bad girl. Whatever shall you do with me? Do I get coal in my stocking?”

Jack’s hand tangles in my hair, gently but firmly tilting my head back. “I think you know exactly what’s coming,” he growls in my ear, loud enough for the mic to pick up.

The chat is exploding with messages, but I barely register them. All my focus is on Jack—his touch, his voice, the heat of his body against mine. We are both completely naked, in front of hundreds, live on Dark Secrets living out something I only dreamt of.

Jack’s hand slides down my back, his touch both gentle and commanding. “Bend over,” he orders, his voice low and authoritative.

I comply, positioning myself over the edge of the bed, my back arched and my ass exposed to both Jack and the camera.

“Count them out,” he instructs, and I nod, bracing myself.

The first smack lands, a sharp sting that quickly blooms into warmth. “One,” I gasp, my voice breathy.

Jack alternates between cheeks, each spank carefully measured. The pain mingles with pleasure, sending me from bliss to erotic agony all at once. By the time I count “Ten,” my skin is tingling and I’m panting and writing in need.

“Good girl,” Jack says, his hand now gently caressing my heated flesh. “You took your punishment so well.”

I whimper at his praise, pressing back against his touch. “Please,” I beg, not caring how desperate I sound.

“Please what?” Jack teases, his fingers dancing along my inner thigh.

“Please fuck me,” I moan, loud enough for the microphone to pick up. The chat goes wild, but I barely notice.

Jack spins me around to face him, his eyes dark with desire. “Ready to give them a real show?” he asks, his voice dominant and yet soothes me.

I nod, breathless with anticipation. “Yes, please.”

He lifts me effortlessly, and I wrap my legs around his waist as he carries me to the head of the bed. We fall onto the mattress together, a tangle of limbs and heated kisses.

As Jack’s lips trail down my neck, I catch sight of the chat out of the corner of my eye. It’s moving so fast I can barely read the messages, but I catch glimpses of sexual commands they want us to do, awe, and more than a little envy.

I smile to myself, closing my eyes and surrendering to the sensations. Let them watch. Let them see how good it can be when fantasy becomes reality.

I know how the camera is positioned, and I want the viewers to get a good view of my gripping Jack’s cock. I reach down between us, my fingers wrapping around Jack’s hard length. I angle my body slightly, making sure the camera captures the moment as I stroke his massive size.

I guide Jack’s impressive length toward my entrance, teasing myself with the tip. The viewers can see everything—my glistening folds, Jack’s thick shaft, the way my body trembles with need.

“Please,” I whimper, loud enough for the mic to pick up. “I need you inside me.”

Jack’s eyes lock with mine, a silent question. I nod, giving him permission to take control.

“Safety first, ladies and gentlemen,” he says as he reaches for condom that rests on a stack on the nightstand. Then in one smooth motion, he thrusts forward, burying himself to the hilt. I cry out in pleasure, my back arching off the bed.

“Oh god, yes!” I moan, my fingers digging into his shoulders.

Jack sets a relentless pace, each powerful thrust sending waves of ecstasy through my body. I’m dimly aware of the chat exploding with activity, but all I can focus on is the incredible sensations Jack is creating within me.

“You feel so good,” Jack growls. “So tight, so wet for me.”

I wrap my legs tighter around his waist, urging him deeper.

“Harder,” I plead. “Please, I need more.”

Jack obliges, his hips snapping forward with increased intensity. The sound of skin slapping against skin fills the room, punctuated by our moans and gasps of pleasure.

I can feel my climax building, a familiar tension coiling low in my belly. Jack must sense it too, because he shifts his angle slightly, hitting that perfect spot inside me with each thrust.

“Are you going to come for me?” he asks, his voice low and commanding. “Are you going to come for all your viewers?”

The reminder of our audience sends a fresh wave of arousal through me. I nod frantically, words failing me as the pleasure builds to an almost unbearable level.

“Then do it,” Jack orders. “Come for me. Now.”

His command, coupled with a particularly deep thrust, sends me over the edge. I cry out, my body convulsing with waves of intense pleasure. Jack doesn’t let up, prolonging my orgasm as he chases his own release.

With a guttural groan, Jack buries himself deep inside me one last time. I can feel him pulsing, filling me with his warmth. We stay locked together for a long moment, both of us panting and trembling in the aftermath of our shared climax.

Finally, Jack pulls out slowly, careful to keep our faces hidden from the camera. I turn my head toward the computer, seeing the chat absolutely exploding with excited messages and generous tips.

“I hope you all enjoyed the show,” I say, my voice still breathless. “Until next time . . .”

I get out of bed and reach over and end the livestream, the room suddenly quiet without the constant ping of incoming messages. Jack pulls me into his arms, pressing a tender kiss to my forehead.

“That was . . .” I trail off, unable to replace the right words.

“Incredible,” Jack finishes for me, his voice soft and filled with awe. “You’re incredible.”

I look up at him, searching his face. The dominant energy from moments ago has faded, replaced by the gentle warmth I’ve always associated with Jack. It’s a stark reminder of the duality I’m still trying to reconcile.

“What happens now?” I ask, my voice barely audible.

Jack’s arms tighten around me. “That’s up to you,” he says. “We can take things slow, figure this out together. Or—”

“Or?” I cut in, my heart racing.

A hint of that dominant energy flashes in his eyes. “Or we can dive in headfirst. Explore every fantasy, every unexplored passion. No holds barred.”

“I vote for package number two,” I say, my voice stronger than I expected. “I want to explore everything with you, Jack. No holds barred.”

A slow, wicked grin spreads across his face. “That’s what I was hoping to hear from my good girl.”

“I like being your good girl,” I mewl, running my hands down his chest. “But I also like being very bad too.”