The Helldesk Ch. 04

"Do you think she plays with herself when she gets lonely? She looks pretty ordinary to me - mid brown hair, medium build, probably wishes she could lose a little weight, maybe someone who prefers the feel and efficiency of her own fingers to the fumblings and lack of fulfillment of a one night stand. Maybe living such a mediocre existence she doesn't know the thrill of what it is to submit to another, to know the excitement of relinquishing control and not knowing what is going to happen next. Maybe she's not as brave as you, or as strong as you have obviously grown to be. Maybe she hasn't even dreamed of such things. Maybe she hopes to meet the love of her life, or maybe she once did, and never even noticed.

"Or maybe that plain and unassuming exterior hides a very different and exciting interior. Maybe she works the phones and talks to truckers and bankers and car mechanics and talks them through her dirtiest fantasies." My hands paused, just outside the crease of her thighs, my fingers, still 'walking', slowly bunching the fabric of her dress under my palms as the hem gradually climbed her thighs. Her body shifted momentarily, and I wondered if she was going to resist, but instead the hem continued its inexorable progress towards her pussy without interruption and as it reached my fingertips, I lightly slid my fingers down the warm smooth flesh I had just exposed, reveling in how deliciously soft it felt to my touch.

"Maybe she also has a hidden Domme persona, one she wields ruthlessly on those who are brave enough to call her." My fingers started to explore a little further afield, first dipping down towards her knees and turning to float up the inside towards that traitorous pussy, just slipping to one side before I made contact. "Maybe she specializes in humiliation and degradation, telling them how weak and pitiful they are, how they could never truly please a woman with the meager equipment they were 'blessed' with." My fingers traced back down the front of her thighs again, turning outwards this time, feeling the sweep of her hamstrings and the swell of her cheeks.

"Perhaps she tells complex stories, woven with intricate details about the punishments she would inflict, the details of the floggers, canes, and whips she would use, bringing these toys to perfect and exquisite life in the minds of her subjects. The marks they would almost visible to see in the minds of those who crave her power to crash down upon their flesh." My fingers edged back down her thigh, the muscles shifting as she moved slightly, their return back up the inside of her thigh causing a small sigh as one makes the briefest of contact with one outer lip. "Maybe she is a real Domina, not just a virtual one. If she was, I think her favorite toy would be a rattan cane, its light weight suitable for her weak, average frame, the speed, the noise of its flight and the devastating crack it makes upon impact as exciting to her as the hapless victim. Swish... crack! Swish... crack! Swish... CRACK! She always keeps them guessing, varying her timing and strength of impact, never giving them time to settle. But just when they get into a rhythm, she stops, leaving them to feel the burn, leg muscles trembling slightly, skin on fire, wondering whether she has drawn blood because she went a little harder that time."

One hand strayed to her hip, the other dipped straight back down between her lips, tracing a sublime path down her dampened cleft, the heel of my hand pressed into the apex of her lips. They pressed down harder, sliding from side to side, and her head tipped back, her arm obscuring my vision of the lone woman now brushing her hair at her vanity. A low moan escaped her lips, matching the movement of my fingers, a hitch coming as my middle finger strayed further down to press down on her hole, teasing the little ring of muscle as I varied the pressure, not quite going far enough as to slide inside, but just starting to overcome her resistance.

"Maybe she's actually a closet sex fiend - a depraved little tart at that. Maybe she enjoys driving out the nearby truckstop in a slutty little outfit and getting taken back to one of those big cabs, climbing back behind the seats to the sleeping area and pulling off her dress to reveal a tight, boned corset and crotchless panties. Maybe she turns around, spreads those panties and begs the guy to fuck her in the ass, maybe she tells him she can't afford to get pregnant, so she trained that tight forbidden hole mercilessly, and that he can pound her without any warm up, just a little spit on the end of his cock."

My other hand reached behind her, matching the story, the fingers coming to rest on her emerald plug. One finger tapped it several times before I took a firm grasped and pulled, the metal bullet finally coming free with a gasp from its owner. I reached into my pants pocket and pulled out the black handkerchief I kept there for emergencies, wrapping the soiled plug in it and thrusting it back into my pocket to be dealt with later.

"Raise your arms," I told her, reaching down to grasp the hem and pulling her own dress over her head and tucking it into my back pocket. "Hands back on top of your head."

I dropped my hands back to their former locations, both fingers testing and reacquainting themselves with just how far I could go before passing the point of no return. I could feel one thigh trembling slightly, her legs slightly further apart than they had been earlier, my fingers afforded slightly easier access, and I could tell that she was getting gradually wetter as I continued this monolog. I wondered whether she was imagining herself in the place of miss mediocre, or whether she was getting a voyeuristic thrill from imagining being a fly on the wall. Either way, her attention was no longer on our surroundings or her own rather exposed position.

I shifted my position slightly so I was off to one side, affording me easier access to both her front and back holes. I raised the fingers of my left hand to my mouth and spat on them liberally, dropping them back to her ass crack to moisten her back passage. I gently increased the pressure of the other hand and the middle finger slid home easily. Her breathing morphed into first a sigh and then a groan, "huhhhh...hmmmmmm... ohhhh yes".

"There's this one guy she sees every couple of weeks who isn't particularly long, but far thicker than anyone else she's ever been with. When she feels the fat, hard head of that meat pressing into her hole, it gets her going like nothing else. Knowing that he's not particularly sensitive and is going to pound her into submission gets her so wet, she gets little rivulets of her juices running down the insides of her thighs." As I mentioned pressing into her hole, my left hand pushed harder and the middle finger pierced her sphincter, sliding in to the first joint. She rocked up onto the balls of her feet, grinding her pubis into my hand, her breathing more ragged now, her lips definitely wetter. I curled my fingers up and started to make small circles on the front of her pussy, feeling the crinkle of the wall of her cunt, searching for a more sensitive spot.

"She usually needs a couple of pillows under her thighs to keep her ass up in the air when he pounds her. She knows that she will feel the aftermath of his ruthlessness for several days and makes sure she only sees him on a Friday night as she doesn't want the embarrassment of having to explain why she hobbles when she walks." My left hand continued to push and slowly eased its way in to the second knuckle. My fingers found their prize and she shivered and clenched down hard on my fingers, her elbows dropping, her hands almost coming down off her head.

"Fuck... ohhh, fuck yes! Press harder... right there!" I reached a tiny bit farther inside and suddenly felt the strange wrinkled bump that I was looking for. I straightened my fingers and hooked them back towards me slightly in a beckoning motion than tickled that little bump. Her gasp signaled that I'd hit the right spot, and I increased the pressure slightly and continued to tickle her.

She dropped her hips slightly, her knees parting a little further, and I drew my rear finger out slightly before pressing back in, alternating the motion of front and rear fingers.

"He always starts slowly, long full strokes where he will often pull out completely, pressing up against her ring again until he slips inside with a little jump, her gasp echoing his successful penetration each time. He'll keep that up for a good ten minutes, pausing occasionally to spit a big mouthful of saliva down into her crack, running the head and shaft of his thick cock up her crack, then plunging back into her hole again, sliding all the way until she can feel his balls pressed up against her other hole. This is usually enough to make her come for the first time, especially when she thinks about how much harder he's going to fuck her in a moment."

I slowly increased the speed of my fingers as I described the imaginary defilement of the woman in front of us. She'd stopped brushing her hair now and appeared to be taking off her makeup. Hopefully, she'd be there a few minutes more until we'd finished our business and I could leave.

"He doesn't give her time to recover, and she's still a little shaky as he slides out and straight back into her, gradually increasing his tempo until he is now fucking her hard - his strokes relentlessly deep, his balls slapping against her lips, her fingers a blur on her clit as she tries to suck every ounce of pleasure from this thoroughly filthy fucking. She moans his name and tells him she's a worthless anal slut, and that he has the best cock she's ever felt piercing her ring. She tells him she loves his thickness and that she often masturbates to the thought of him reaming her ass for days to come."

The slut's legs were trembling noticeably now, her moans almost one continuous noise, my fingers in both her holes getting her almost as turned on as the woman in my story. As I turned onto the home straight, I pressed a second finger up against her puckered rear ring, and her elbows jerked down in surprise, the second finger gradually sliding home despite considerable resistance.

"Ohh god oh god oh god... Sirrrrrr... please fuck my pussy, I want to feel your hard cock inside me. Bend me over the hood of the car and fuck me from behind and tell me how it ends."

My fingers pulled out of her cunt and delivered a stinging slap to her clit and upper lips. Her cry was loud enough that I see the woman in the window's head turn, and we both froze for a moment, waiting to find out if she could actually see us. After an electric couple of seconds, the woman turned back to her mirror and resumed her work, our presence either unnoticed or uninteresting to her.

"You... do... not... tell... me... what... to... do... " I continued to slap her mons and clit, her body bucking each time I made contact, her legs continuing to tremble, a nice burn probably going on by now. I stroked my fingers back down her slit, the middle two fingers sliding easily home this time, my reach inside her ever so slightly deeper this time, the pressure I was able to exert just a little greater.

I continued where I had left off, my front fingers caressing the knobbly front wall of her tunnel, the others having never left her ass, still buried two knuckles deep.

"Are you getting close little slut? Are you ready for me to make you cum? I do so enjoy hearing your cries as I pleasure your holes in ways you would never let anyone else do. Are you enjoying my fingers in your ass and your pussy at the same time?"

She nodded, her eyes screwed shut, no longer watching the woman across the way. I stopped making circles with my front fingers, and pushed them as far inside her as I could, my palm and the heel of my hand pressing up hard against her lips. I relaxed the other hand slightly and let the back pressure of her muscles slowly evict me. As my fingers slid out, I brought them around in front of her and ordered her to spit, her efforts not quite providing enough saliva to coat them. I added my own and rubbed them back and forward over her clenched ring, before pushing straight back inside her, her gasp locked behind clenched lips and teeth, but still satisfyingly audible to me.

With both sets of fingers once again buried inside her, I leaned forward and whispered in her ear, "I am the one who decides how and when, and if you cum, my fucksicle. I'm going to fuck both your holes with my fingers now and I'm not going to stop even if you make enough noise to have that woman come out to investigate. She'll probably turn the rear porch light on which will be enough to illuminate you blowing and shaking like a steam train, your juices running down your legs as you come down from your orgasm."

I slowly started to draw both sets of fingers out of her, pausing just before they left her, then pushing firmly back up inside her, both palms coming to cup her groin from either side at the same time. I started on a medium speed rhythm, never pausing at top or bottom, but keeping the strokes long enough that the palm of the front hand slapped up against her lips, the heel of the palm and the wrist sometimes slapping up against her clit.

"As he gets closer to coming, the trucker with that thick cock increases his tempo, his weight balanced on his wrists and his knees, his hips pumping forward each time he spears into her tender ring. His speed is quite ferocious now, her cries loud enough to be heard outside the truck, even over the noise of the rumbling beast beneath them. He drops his weight onto his elbows, his chest pressing down onto her back, one hand sliding beneath her to clamp onto one breast, the other reaching forward, under her armpit to grab her by the throat as he whispers in her ear, "Squeal for me now, you fucking slut, I'm going to cum deep in that dirty, slutty ass of yours. If you let so much as one drop escape, I'm going to make your drink the entire load, before I send you on your way. If you're good and you clench down hard enough, maybe you can stop it dribbling down your thighs before you make it to the bathroom and everyone finds out what a cheap whore you are."

I'm finger-fucking the slut's pussy hard now. One hand has come down off her head and is helping my fingers to fuck her pussy, her exertion audible as she gets close to her release. My other hand is still, stuffed as far up her ass as I can get it, providing me with a little more leverage as I ram my fingers into her cunt as fast as I'm able, pressing up firmly against her g-spot.

"He grips her throat tightly, pulling hard on her breast as he accelerates towards his ending. The woman squeezes her clit, her body on fire, about burst into flame as she waits to feel the heat of his cum fire into her ass. His groin is pounding up against her ass cheeks, mashing her clit down against her fingers, the thump of each impact sending little jolts through her body as the pressure builds and she feels like she's about to shatter into a million pieces

"Oh fuck, I'm going to fucking cum... I'm going to cum so fucking hard... I'm...", the slut is pounding my hand up into her crotch, as every muscle in her body starts to tense up.

"And then he stiffens, straining to penetrate as deeply as he can into her ass, and suddenly she feels splash after splash of heat up inside her, his grunt of ecstasy mirrored by her strained wail of pleasure as she cums for the second time, her fingers continuing to frig her clit, his hand still clamped tightly around her throat."

"UnnnghhhHHHHHHHHFUUUuuuuuuuuucccckkkkkkk," her free hand clamped down over her mouth as the pressure finally got to be too much for the little tart and she came hard, her juices leaking out from between my fingers in little spurts. I didn't let up for one moment though, my fingers continuing to ream her tightly clenched pussy, the fingers stroking her front wall and only adding to the mess she was making all over my hand and down her legs. She was shaking and shuddering, the muscles in her belly spasming, her walls clamping down hungrily on my fingers, and with her eyes still closed I knew that she was oblivious to the woman in the window, now standing and staring directly at us. As I watched, the woman reached across and drew the curtain, shutting herself off from our depravity and darkening our scene just that fraction more.

As she finally started to come down off her high, Emma sank to her knees, still breathing heavily. I reached forward with my left hand and grasped her hair, pulling her head back and stuffing my wet fingers into her mouth. "Suck your cum off my fingers, Emma, I want you to leave them nice and clean. We wouldn't want to leave the rental company with any dirty thoughts, now would we?" She squirmed beneath my hands but eventually did as she was told, just before I was going to pull my fingers back out and introduce them to her cheek.

I pushed her forward onto her hands and knees and stepped back to stand by the car door. I gazed down at that gorgeous body, soiled and abused, but still completely desirable. Did I really want to...?

Ahh, fuck it! Before I could blow it, I yanked open the car door and dropped into the driver's seat, closing the door smartly behind me and tapping the button that locked all four car doors. I reached behind me, pulling the dress from where I had tucked it earlier, and dropped it onto the passenger seat next to me.

For a moment she didn't move, and then her head came up as she looked around to see what I was doing. When she saw me sitting in the driver's seat, it took her a moment to do the math, and then she was on her feet in an instant and over to the car window, her hands pressed against the glass, her eyes pleading silently with me, her words as predictable as I had known they would be.

"No no no no nononono noooo. Don't you dare do this! My job, I can't get fired, how will I pay the bills? Even you wouldn't be this ruthless?" The uncertainty in her voice showed with the final furrowing of her brow. Did she doubt me? Maybe she thought I was playing her for some ulterior gain?

I reached over to the door and watched the momentary relief first flicker into life and then snuff out as I cracked the window a mere half inch, the doors staying resolutely locked.

"My dear, dear Emma. I do hope you enjoyed our dirty little fingerfuck. You should have kept your eyes open, then you would have seen the woman in the window watching you orgasm. Seeing you getting fingered like a desperate little teenager in a parking lot." Her eyes slipped over her shoulder, before coming back to fix on me again. The fingers of one hand sliding up to the sliver of a gap between the top of the window and the frame.

"Oh, I wouldn't recommend doing that pet, lots of accidents every year where little children get their fingers trapped in power windows. Serious injuries... some of them." My hand strayed back towards the door and her hands fled back down the glass out of harm's way.

"Anyway poppet, I thought you should know that I don't think you were being completely truthful with me earlier, now were you?" She continued to stare at me through the glass. "You see, I don't think it would have taken twenty minutes for the manager at that restaurant to give you a verbal spanking and then send you out the back door. I thought you needed to understand the gravity of the situation." I paused for a moment, my gaze steely, hoping she understood just how much she had pissed me off.

"I won't stand to be lied to, Emma. It undermines my trust in you and makes it much more difficult for me to be sure of how you will react. I need to know that I'm not going to push you over the edge or put you in a situation you can't handle."