Jailer Jack Pt 03

Waking up next to Jack was a new level of anguish. My head was still slow and spinning, but my body responded readily enough. Jack groaned in triumph when he filled my depths, his insidious whispering in my ear as my pussy milked his shaft.

"Fuck yeah baby, suck it right out of me. Deep into your tight little cunt," he growled, flooding me with liquid heat. "I've wanted to fuck you awake like this for so long. But you cumming on my cock? So hot. Because you're not stoned now, are you, Mel? The truth is, you just like fucking me."

I pressed my face into my pillow when he got up and stayed there in my tiny pocket of darkness as I heard the shower start, and groaned in frustration when I realized that my bed and pillows smelled like him now. Sandalwood and rum. And sex.

My woozy head spun. He was wrong. I

was

still a little stoned. And he was wrong about something else too, wasn't he? Body and mind were different things. My body knew he wasn't trying to hurt me, not physically. Surely that's why I was reacting the way I was. And knowing it was Jack whose cum leaked out of me, making my thighs slippery, did

not

make me happy.

And I couldn't stop him anyway.

The water shut off, and the bathroom door opened. He slapped my ass and chucked when I flinched away.

"Come downstairs. You'll need your energy today," he said.

Soon afterward, I was wrapped in my fluffy robe, grateful for the respite from nudity. With my back turned to him as I stuffed bread in the toaster, and aware that my sober-ish thinking on a short timer, I made the conscious decision to play along. There wasn't much choice, but it would be a hell of a lot easier to get through the rest of Jack's games if I pretended he was literally anyone else. Some celebrity, perhaps, or one of the boys I'd crushed on at school.

But maybe...

I sat and watched him over the top of my coffee cup as he made himself breakfast, glancing down at the cookie balanced on the edge of my plate.

"Hey Jack?"

"Yes, baby?"

"Please don't get mad, but isn't that enough? I mean... you can't seriously expect to keep this going all weekend? You got what you wanted."

Jack turned, plate in hand, and sat across from me. The same place he'd sat when my world had shifted sideways. "Mel, I've wanted you for years. I knew you'd never date me, and I went to all this trouble to get here. Why on earth do you think one night would be enough?"

"So what happens afterward? Will you delete the video? All of them?"

"Absolutely not."

"What then?"

Jack bit into his toast and fixed me with his signature stare as he chewed. "Are you under the impression that this weekend is it? No, baby. I'm taking this whole weekend because it's our first time. But this isn't over when I leave Sunday night," he said, slurping his coffee. "Besides, how many times have you cum now? Part of you is enjoying this."

"You got me stoned and made me watch porn, Jack. I won't deny you seem to know what you're doing, but you gave me drugs," I said, trying to control the volume of my voice. "I don't like you, Jack. You scare me."

"You don't need the porn. I could make you sit on my cock right now and I'd get you to cum in less than five minutes."

"Maybe, but it would still be you making me. I wouldn't do it if I had a choice."

Jack went quiet, then shrugged. "Too bad. I have a bunch of videos now. I can just as easily put them on the porn sites too. And to be honest, you would definitely look like you were enjoying yourself."

"Then what do you

want

!?"

"I want

you

. I won't always ask for the entire weekend, or even the whole time your dad is away every week. But I want at least two of those nights. Maybe a couple of hours after game night. Because now I know how good you feel, and I know hard I can make you cum, this isn't enough. Not by a long shot. For now, you're mine."

"So what, I'm your secret sex pet?"

"Would you prefer to go public as my girlfriend? I'd love that."

"NO!" I said, scowling at him as he chuckled.

"Secret sex pet it is," he said. "Also, call Martin. Now. Tell him you've woken up sick and can't work this weekend. Say you shouldn't be around food, he'll be terrified of contamination in the kitchen."

Jack made me sit on his lap when I called so he could hear the conversation, slipping his hand inside my robe to caress my breasts as I spoke. I hoped Martin would deduce something from my voice, would magically figure out what was happening and somehow stop it. But of course he didn't.

When the call was done, I was allowed back in my own seat, though not to close the now-gaping robe. Jack pointed to the weed cookie and told me to eat it while he explained how to 'prepare for him' for the day, sliding a strange-looking device across the table toward me. I obediently chewed and swallowed the chocolatey drugs as I gazed at the weird bulb and detachable nozzle-thing.

When I protested, he reminded me he'd already uploaded all the footage from the laptop to his personal computer back home, and pointed out that all it would take was minimal editing to show every time I'd orgasmed. There was no way it would look like I'd been forced. He pushed the stuff closer toward me from across the table and waited.

"I don't understand. You've got the condoms?" I said, grimacing as I imagined what I would have to do with it.

"Yes, but I don't like them. That stuff will get you clean enough that I can fuck you without a condom. Don't give me that look, Mel. I know what I'm doing," he growled. "By the time I leave on Sunday night, your pussy and ass will be overflowing with my cum."

"Do you, uh, clean off before you fuck anywhere else?" I asked timidly, already exhausted.

"Of course. Now get moving. The cookie will take about half an hour to kick in, and you'll need to focus the first time you try this. Go."

Once alone in the bathroom, the reprieve was a blessing, regardless of the task. I glared at the silicone nozzle and bulb and followed Jack's instructions, trying to hype myself up. He's already fucked my ass once, and it hadn't hurt, not really. At least this way was cleaner. Despite everything, he seemed fairly knowledgeable about it all.

And, as always in this screwed-up situation, there was no choice.

I'd finished everything and was staring listlessly into the mirror when he knocked, his voice muffled behind the door.

"How many times have you rinsed out now?"

"Three."

"Water is running clear?" he asked, and I told him it was. "Good."

I yelped when the door opened and Jack walked in, towel still swathed around his hips. He made me climb up onto the vanity and spread my legs wide. Despite the provocative position, he ignored me as he wandered about, dragging a stool from the corner, gathering soap, washcloth, moisturizer, and snapping a fresh blade on my fancy safety razor. Jack was oddly gentle as he perched on the stool and began shaving away my pubic hair, murmuring about how it would be my job to stay hairless from now on, and suggested some different methods.

"What's this for?" I asked, barely daring to breathe as he ran the razor over my mound. There wasn't much, but slowly, the sparse hair I had disappeared.

"I like it. And I want to have an unimpeded view of your hot little pussy hugging my cock," he said, holding my skin taut and swiping away a little more hair. "You've got no idea how different your pussy looks when you're horny, do you?"

"No?" I frowned, surprised at yet another way my body was betraying me. And that Jack could read it so easily.

"Right now, you're not really aroused at all. Which is fair, especially after the cleanup routine. I imagine that was strange for you," he said, wiping away the soap on my mound with a washcloth and inspecting his work, carefully resoaping and going over areas he missed. "But when you're horny, your clit gets bigger, and hard. The flesh around your pussy gets puffy too. And of course, you get unbelievably wet."

"What?"

"You can't hide that kind of stuff, Mel. And regardless of the weed, you are incredibly responsive. Which is why I know that, despite your protests, your body likes me. It knows I can make you feel good. So you never know, where the body goes, the mind follows."

"I'm not sure that's-"

"And there," he said, smoothing moisturizing oil over my freshly bare skin, and groaned as he spread the slick lips of my pussy wide. "You have no idea how hot this is."

I squeaked as Jack pushed a finger inside me and leaned forward to swipe at my clit with his tongue. It didn't take long before each breath left me in a soft moan, and Jack's thrusting hand made wet sounds as it fucked me. When he sat back up, his lips and chin shone.

"See baby? Your clit gets fat, so fast," he said. "So you really enjoy what I do to you, or you're naturally like this. Either way, it's the same outcome."

"What outcome?" I squeaked, hating that my voice was so breathy.

"Every time you cum, it'll make that link in your mind a little stronger. That

I

mean orgasms. With any luck, it'll only take a few weeks before you start getting wet before I even show up," he said, pulsing his fingers into my g-spot as I squirmed and my legs twitched wider. "So while you're telling yourself that you don't like me, deep down, you'll still be craving everything I do to you. You'll be craving

me

."

I opened my mouth to tell him that Stockholm syndrome wasn't the same thing as liking someone, but he chose that moment to dive back toward my pussy, his tongue slippery and frantic over my clit. My spine curved and tilted my pelvis toward him, and Jack hooked his fingers hard as I exploded. My head fell back, my skin making squeaking noises on the bathroom mirror as I shuddered, and only his hands stopped me from toppling off the vanity. Jack groaned as my pussy clutched, the vibration over my skin setting me off again, searing waves of delirium breaking me a little more.

"There you go, baby. And you know what? I'm fairly sure you're multi-orgasmic. Was that your third or fourth for the day? And you're not even really stoned yet." Jack's grin was triumphant as he stood, gazing down at my languid body, and kissed me with his pussy-stained lips. "Now, have a shower, and I'll be in the living room."

By the time I stumbled downstairs, I was back in the swirling throes of the drugs. Thanks to the link in my mind, well and truly forged the night before, my nipples were already hardening. I fucking hated him. And it was confusing as hell because it felt good.

Jack idly flicked through the channels on TV, giving me a broad smile when I walked in. I hadn't bothered getting dressed. He stood and hooked his arm around my waist, pulling me close in one of his signature stifling hugs.

"You just accidentally fulfilled a fantasy. Walking into a room naked and about to fuck, that's so fucking hot, baby. I have a surprise for you. Come with me," he said. My stomach dropped as he led me downstairs to the basement. Jack had been busy.

There was an exercise mat on the floor, a blanket over the top, and every light was on. I shuddered. There was no hiding in the dark this time. He walked us over to the mirrors, his arms sliding possessively around me from behind. The edges still warped our reflections, but Jack had chosen the least distorted panel to set up his fuckspace in front of. Morbid fascination kept me frozen in place, watching as Jack's hands cupped my breasts, fondling my skin as he groaned.

"Look at us Mel. Fuck, you're sexy. Even though you're pretending to not enjoy this, your nipples are hard, and you're practically panting. I bet you're wet already," he said, skating his hand lower over my mound, his fingers disappearing inside me. They emerged glistening. "See baby? I've barely done anything, and you're already drooling."

My eyes slipped shut, blocking the live porn show Jack had orchestrated as his teeth grazed my neck and his fingers plunged back in. The now-familiar waves of weed were hitting me hard, and my hips undulated with Jack's manipulation.

"No, Mel. You don't get to do that. You're going to watch," he said, his hand sliding from my breast to my throat and squeezing until my eyes flickered open. "You'll watch it all. I want you to see your own reactions to everything. So you understand how right this is. So you can see that it's

me

making you feel good, and exactly how much you want this too."

He released me, and I watched as Jack dragged a chair over, planting it so close to the mirror wall his knees almost touched when he sat down. I took his offered hand, and he sat me on his lap before him, unable to escape the extremely close view. His cock bobbed between my thighs as he draped my arm back and around his neck, forcing my breasts high and heaving. His breath was heavy on my neck, while in the reflection, he pulled my glistening pussy open.

"Look baby, you're soaked. The truth is right in front of your eyes. You love this," he said, pulling my skin taut over my pubic bone so my clit protruded obscenely. With his other hand, he pulled the hood back and rolled the exposed wet bud around as I writhed. "See that? That little button of yours is easily twice the size. That's how I know you're just as horny as I am. And you're literally dripping."

The cockskin closest to my pussy visibly shone with moisture as he continued to tease me. It was so much worse than the night before. There was nowhere for me to hide when he reached under and gripped my thighs, raising me up just enough for his meaty length to almost reach my entrance.

"Put it in, baby," he said, his eyes boring into mine in the reflection, groaning when I complied. The Mel in the mirror arched her back, thrusting her breasts out as she was lowered onto the monstrous cock. But it became impossible to disassociate once it stretched me out. My breath came faster when I was once again seated in Jack's lap, and he groaned and jerked inside me, his gaze glued to where our bodies connected. "Fuck yeah, look at that. I can feel your pussy squeezing me, Mel. Maybe you should quit pretending you don't love being stuffed full of my cock."

I said nothing, my eyes also glued to the obscene tableau before me. He guided my feet to the bars on either side of the chair and wrapped his arms around me. One hand on my breast and the other playing with my clit, and my passage clutched helplessly at the heavy cock splitting my pussy lips.

"Fuck, I could almost cum just from you squeezing me that. And your fat little clitty is so hard. You like seeing yourself sitting on my cock? I think you do, Mel," he whispered in my ear, rolling me with his limited movement on his thick shaft, undeniably glistening with my juices whenever the scant inch or so became visible. My breath came in pants and my spine bowed as his fingers swirled. Low in my belly, a gentle fire burned fiercer, and I let my body take over, flexing my legs to roll with him. "Yes baby, fuck me. Cum on me."

Jack's eyes met mine as he pinched my clit, and I broke apart, slamming him as deep as I could manage as I detonated. I pitched forward as the burning quakes of orgasm raged, and Jack's arms tightened to hold my shuddering body against him. A hoarse keening burst from my throat, and his chuckle vibrated on my back.

"Fuck, that's nice. You're gonna lose count of how many times you cum when I'm inside you this weekend. And we are definitely coming down here again," Jack said, gently urging me to stand as his cock left my body with a slurp. He pushed the chair away and pulled me down onto the blanket, the exercise mat below firm at my back as he kneeled between my legs. With a slap of wet skin, Jack forced his cock flat against my belly, a wicked grin curving his lips. "Look baby. That's how deep I go."

I glanced down and shuddered. I hadn't thought about it, despite how many times Jack had fucked me already. It was difficult to tell from my angle, but his weeping cockhead seemed to almost reach my navel, and was thicker than my wrist. I knew from sucking the meaty shaft that it was wider at the base, the same girth that stretched my body whenever he stuffed me full. A monster cock, better suited for porn, not this strange orgasmic nightmare.

Jack's grin grew as he hitched my legs up over his shoulders, pulling back until his cockhead nudged at my entrance, now raised up invitingly toward him as he leaned over me. He teased me open with the broad head, which even now was a not-quite-painful stretch, and sank the entire length inside as I watched. In this folded, trapped position, my body felt compressed, and Jack's massive presence was overwhelming.

"Fuck yeah baby, look how you're wrapped around my cock," he said, pulling the glistening monster almost all the way out and sinking back in slowly, so I felt every inch of his invasion. "You wouldn't be able to take me so easily if you weren't

really

turned on, Mel. Look how wet it comes out."

I half-expected it to poke out of my belly as he ground into me. Jack bent me almost completely double as he fucked. Long, deep strokes that set my body on fire, making it hard to think about anything but the fat shaft inside me. When he dropped his head and sought my lips, his mouth was as hungry and demanding as his cock.

At least when we were kissing, I could keep my eyes shut. The small darkness didn't help make any more sense of the electric shocks still running through me, the searing high that made my skin blaze, and the utter confusion of it all. I kept catching myself kissing him back. It was easy when I couldn't see. He groaned into my mouth whenever he bottomed out, and my pussy clutched at him hard.

"Look baby," Jack whispered when he came up for air, and I followed his gaze to our reflection. He'd positioned us side-on to the mirror, and as I watched, Jack pulled slowly out until I could feel just the head of his cock nestling slippery and hot between my inner lips. It was even more shocking from that angle. How could something like that fit? But it did, over and over. I imagined it spearing into my depths, pressing up against my cervix, already sodden with his seed. And as he filled me again, that massive slab of flesh stretching my pussy to fit him, the utter depravity of it all smashed into my mind and an orgasm crashed over me out of nowhere.

Jack grunted in surprise as my body grasped and pulsated around him, and held my face steady as my belly went supernova. He refused to let me look away as the waves of orgasm crested, and grinning as muffled moans escaped between my clenched teeth. He thrust into me hard a few times, laughing as I writhed when his deep grinding cock sent fresh crackles of electricity through me, finally dropping his mouth to my breasts to suck my nipples as it faded.

"You nearly made me cum, baby. But I love that you got off from watching how deep my cock fucks you," he murmured as he pulled out, groaning as my hips chased him before slumping to the floor. He sat back and gazed down at my splayed and panting body. "I'll never get enough of this. We fit together so well, and the more you get used to me, the harder you cum."

"It's... the cookies..." I panted.

"You can keep telling yourself that, but that's not how weed works. It relaxes you, maybe even enhances things a bit, but it wouldn't do a damn thing if you weren't horny for real," he said, rolling me over on to my knees and shuffling us around. He ran his cockhead up and down my slit, chuckling as I tried to suppress a shudder. "Put aside the circumstances for a minute, and just concentrate on how your body feels. Weed doesn't cause a reaction like

this

."

Jack slammed his cock in hard, and my head snapped up, a needy shriek escaping my lips as I instinctively bucked toward him. He ground into me for a moment before pulling out slowly and slamming back in again, over and over. Each burning thrust into my hopelessly high, undeniably aroused body made me moan. And even to my ears, it didn't sound like despair.