Rougher Than Ever

  ROUGHER THAN EVER

  THE ESCORT CHRONICLES: VOLUME FIVE

  JT HOLLAND

  Copyright 2016 JT Holland

  AE PUBLICATIONS

  SMASHWORDS EDITION

  Smashwords Edition, License Notes

  This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to Smashwords.com and purchase your own copy. Thank you for respecting the hard work of this author.

  WARNING: This story is intended for a mature audience only! Contains explicit, graphic sex and language. Not intended for individuals under the age of 18. All character are over 18 years of age.

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  TABLE OF CONTENTS

  ROUGHER THAN EVER

  ALSO BY JT HOLLAND

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  ROUGHER THAN EVER

  Eric Carlson is halfway through his third bottle of wine when there’s a knock on the door of his suite.

  He takes one last swig directly from the bottle then sets it on the table and heads over to answer the door, the room wavering just a bit from the effects of the wine.

  Normally he goes into these sessions relatively sober but tonight he has a different plan; to consume as much alcohol as possible before the session starts. Because even though he’s come a long way in the last couple of months, Eric still has some inhibitions. He’s just wired that way. He’s hoping that if he drinks enough he’ll be able to push past them. He’s not sure it will work out like he’s planning, but he figures it won’t hurt to try.

  He comes to the door and peeks out the spyhole. Standing there is a short, fully-stacked, raven-haired beauty wearing blue jeans and an unzipped black leather jacket with only a lacy bra underneath, showing off her huge, glorious breasts without absolutely no shame. With her hair cut in a sharp, edgy style and her face caked with makeup, Tory plays up her sluttiness to the max, which is exactly what Eric is looking for tonight. A straight-up slut to run roughshod over.

  Eric has been through a really tough couple of weeks and he wants to take out his anger on someone. Not too long ago, that would have meant a phone call to Jasmine. But he’s spent so much time with her lately that he’s starting to develop feelings for her, which makes it harder and harder to debase her like he used to. That’s not to say that they haven’t got freakier with each other as time has gone on, but it their nights together are no longer rooted in anger. Which, ultimately, is a good thing.

  But not tonight. Tonight Eric is pissed off. And he wants to take his rage out on someone. Which is why he called Tory a couple of hours ago instead of Jasmine.

  He’s been with Tory once before, when she tagged along with Jasmine for one of their sessions, so he knows what he’s getting. But because he doesn’t have any feelings towards her, it’s easier to see her as just a fucktoy, which means he won’t have to worry about conflicting emotions when he’s treating her like shit.

  Tory knows exactly what she’s getting into tonight. Eric made that quite clear to her on the phone. And she’s fine with it. Looking forward to it, actually. Or so she says, which is good enough for Eric.

  He opens the door and lets Tory in and closes the door behind her.

  “I wasn’t expecting to hear from you again,” Tory says as she crosses the room towards the table with the bottle of wine sitting on it. “I figured you’d give Jasmine a call whenever you wanted a night like this.”

  “Normally I would,” Eric says. “But I was in the mood for something different tonight.”

  “Don’t get me wrong,” Tory says, “It’s fine with me. I was just surprised, that’s all.” She picks up the bottle of wine. “Do you mind if I have some?”

  “Be my guest. I’ll get you a glass.”

  “Don’t bother,” Tory says. “I don’t need one.”

  She proceeds to take a long swig straight from the bottle before pulling it from her lips and holding it out towards Eric.

  Smiling, he grabs the bottle from her. “That wasn’t a very polite thing to do,” he says before proceeding to do the exact same thing.

  “Nobody’s ever accused me of being polite before,” Jasmine replies, matching his grin.

  “Which is exactly why you’re here tonight instead of Jasmine,” Eric says.

  “Fair enough,” Tory says. “She says hi, by the way.”

  “Who? Jasmine?”

  Tory nods.

  “You told her you were coming to see me?” Eric asks.

  “Of course,” Tory says. “We talk all the time.”

  “Is she upset?” Eric asks.

  Tory laughs and shakes her head. “No. Not at all. She understands.”

  “Really?”

  “Yep. She’s flattered, even.”

  “Is that right?”

  “It sure is,” Tory says. “Personally, I think it’s kind of pathetic, but that’s just me.”

  “Pathetic, huh?” Eric says, smiling ruefully. He’s not sure if Tory means what she’s saying or just playing a role, and he doesn’t really care. Either way she’s helping him get in the right mood for the evening.

  “Yeah. I mean, we are escorts, in case you didn’t remember,” Tory continues. “It’s not like she’s your girlfriend or something.”

  “Maybe not,” Eric says, undoing his belt and slipping it off his waist. He grips the buckle in his fist and rolls the belt over his hand until only six inches are still sticking out. “But I do have feelings for her. Which means I’d probably subconsciously take it easy on her. But you I hardly even know. So I won’t have those same issues.”

  He slaps the belt on the palm of his hand. The sound fills the room like a gunshot but Tory doesn’t even flinch. Apparently she’s used to this sort of thing. Eric smiles, his excitement overflowing already.

  “Are you ready to get started?” Eric asks, slapping the belt against his hand again, hard enough to leave a red mark this time.

  “Whenever you are,” Tory replies.

  In lieu of a reply Eric smacks her across the ass with his belt.

  Tory yelps in surprise and takes a small step forward to maintain her balance. She flashes him a dirty look.

  “Surprised you a bit there, didn’t I?” Eric says, his mouth turned up in a wicked smile.

  “A little,” she says.

  He smacks her across the ass again, a little more forcefully. But Tory was expecting it and bites down on her bottom lip instead of making any sound. She glares at him with defiance in her eyes.

  “You’ve got a little bit of an edge to you, don’t you?” Eric says, laughing softly. He’s thoroughly enjoying this.

  Tory doesn’t bother with a response. She just continues glaring at him.

  “That’s good,” he says. “It’ll make it more gratifying when I break you.”

  Tory scoffs. “Break me? You?” She shakes her head. “It’s never going to happen.”

  “We’ll see,” Eric says. He smacks her ass again, even harder.

  A flash of pain crosses Tory’s features for a moment and she makes a little gasping sound. Fortunately her breath is quickening and her face is starting to flush too, which means that the pain brings her some pleasure along with it. Which is exactly what Eric is shooting for.

  “That one stung a bit, didn’t it?” he says.

  “Nothing I haven’t felt before,” she replies, her mouth turned up in a sneer.

  “So it’s not too much for you?”

  “Not even close.”

  “That’s what I like to hear,” Eric says. “Because we’ve got a lot further to go.
”

  “Bring it on,” Tory says.

  “Oh, I intend to,” he says.

  He unrolls the belt from his fist and runs the tail through the buckle, creating a loop. Standing face-to-face with her, he slips the loop over Tory’s neck and tightens it. Not so much that it’s choking her but not loosely either.

  “Take your jacket off,” Eric says.

  Tory does as she’s told. If she’s at all alarmed by the belt around her neck she isn’t showing it.

  “Now your bra,” he says.

  She slips it off, revealing her huge tits. Firm but not overly so, floppy but not droopy, they are glorious and just begging to be played with. He can’t resist.

  Using the belt as a leash, Eric leads her over to the nearest wall. Once there, he pushes her up against it, back first.

  “Open your mouth,” Eric says.

  She does.

  Eric puts the tail of the belt between her teeth, lengthwise, the flat side parallel to the ground.

  “Bite down,” he says.

  Tory bites down on the leather.

  “Don’t drop that belt, no matter what,” Eric says. “Understand?”

  Tory nods.

  “Good,” Eric says. Then he starts working her tits with his hands, groping and cupping and squeezing them before starting in on her nipples, rubbing and playing with her them until they’re hard.

  Once they are both sticking out he grabs them between his forefinger and thumb, one nipple for each hand. He starts off by rubbing them between his fingers, gently at first but gradually increasing the pressure and intensity.

  Tory is moaning lightly behind the belt and her breath is growing ever more rapid. So far, so good.

  He rubs her nipples between his fingers for another couple of seconds, then gives them both a hard pinch, eliciting a gasp from Tory but not a big enough one to force her to drop the belt.

  “Not bad,” he says. “Not bad at all.”

  Despite the compliment, Eric doesn’t let up. In fact, he squeezes even harder, twisting both hands at the same time, tweaking her nipples, pulling on them, stretching them out.

  Tory is moaning loudly and her body is starting to quiver but still she doesn’t let go of the belt.

  Likewise, Eric doesn’t let go of her nipples, pinching them between his fingers and turning them nearly 360 degrees before finally releasing them.

  Tory gasps at the sudden absence of pain, this time nearly dropping the belt from her mouth.

  He barely gives her a chance to recover before slapping down on one of her tits with and open hand. She grunts behind the belt. He slaps the other tit, eliciting another grunt.

  For the next minute or so he smacks the hell out of her tits, trading off, one and then the other, giving her just enough time to recover in between slaps that she feels the full force of every single blow.

  By the end of the session Tory’s tits are bright red and her chest is heaving. Tears are leaking from her eyes, making her mascara run down her face. But based on the tight set of her jaw and her defiant eyes, she’s far from defeated.

  “That was pretty impressive,” Eric says, pulling the belt from her mouth. “You’re tougher than you look.”

  “That was nothing,” she says. “I deal with worse every day.”

  “I’m sure you do,” Eric says. He spins the belt so his hand holding it is behind her head, the buckle pressing up against the skin on the back of her neck. Then he raises his hand holding the belt over her head, pulling it tight around her neck, choking her. “And rest assured, you’ll be dealing with worse tonight. This is only the beginning.”

  “I can’t wait,” she manages to croak out even though she can barely breathe.

  Laughing, Eric lets his hand drop.

  Before Tory can catch her breath, Eric spins her around and pushes her face-first against the wall.

  Without saying a thing, he undoes the belt, releases it from her neck, sticks the tail in his mouth and bites down on it. He grabs one of her arms and pulls it behind her back. Then does the same for her other arm, crossing one of her wrists over the other.

  Holding her arms together with one hand, Eric reaches for the belt with his free hand. He wraps the belt around her wrists a couple of times in a figure-eight pattern, then once again slips the tail of the belt into the buckle and sticks the prong into one of the holes, effectively handcuffing her.

  Once Tory’s arms are incapacitated, Eric squats down. Reaching around her waist, he undoes the button and zipper on her jeans and pulls them down, panties and all. He doesn’t take them completely off, however, instead stopping once the waistband is just below her ass.

  Now her legs are trapped, along with her arms, rendering her essentially helpless. Time to turn up the heat.

  Eric stands up and presses against her, his groin pushing against the top part of her ass, his cock pressing painfully against his pants. With his chin over her shoulder he slides his hand down the front of her body, stopping for a moment to grope her tits some more before proceeding down her stomach until his hand is between her legs.

  He’s planning on rubbing the outside of her shaved snatch to get her warmed up but she’s already soaking wet down there—apparently getting smacked around turns Tory on quite a bit—so he decides to get right down to business. He slips two fingers into her pussy and slams them up into her with as much force as he can muster.

  Even in her 3-inch heels, Tory is quite a few inches shorter than Eric, forcing him to lower his body by spreading his legs wider in order to get any leverage in their current position. The upside to this is his groin is now pressing directly against her ass. Unfortunately his cock is still in his pants. He’s tempted to pull it out but is afraid he won’t be able to keep himself from sticking it into Tory, something he’s trying to hold off on for the time being.

  Trying to take his mind off his cock, he slides a third finger inside Tory’s pussy, causing her to gasp audibly. Moving his hand back and forth quickly, his fingers filling up her pussy, Eric fingerfucks her without mercy while she moans and squirms beneath him.

  Every sound Tory makes entices him to bang her with more force; every time she cries out he pushes his fingers further inside her, every increase in her breath rate just inspires him to slam her with more aggression.

  Once he thinks she’s getting comfortable, he forces his pinky inside her pussy, making it four fingers altogether.

  Tory reacts to this with a high-pitched whimper. But Eric doesn’t want to hear it. He covers her mouth with his free hand and continues slamming her pussy with everything he has.

  As soon as she’s used to this new development, Eric switches it up again, this time pulling his hand from over her mouth and gripping her around the throat.

  He proceeds to choke Tory while he bangs her with his fingers, tightening his grip with every passing second without letting up at all on her pussy.

  Unable to breathe, Tory starts to fade quickly. Her face is growing red and her legs are starting to weaken. Her mouth is slightly open and her lips are moving but just barely. Her eyelids are fluttering. But still her body reacts to his fingers: Her pussy is wetter than ever.

  It isn’t until Tory’s eyes fall closed and her head starts to slump that Eric releases his hold on her throat.

  Her chest heaves as her body once again draws air. Her face regains its color and her eyes reopen, wider—and filled with more excitement—than ever.

  This brush with unconsciousness seems to stimulate Tory even more. She lets out a scream of pleasure as an orgasm overwhelms her body. Her pussy gushes juices, soaking Eric’s hand and dripping onto the carpet. Her return to the conscious world also appears to have heightened her sensitivity, as she suddenly tries to squirm out of Eric’s grip, twisting her lower body in an attempt to pull away from his fingers.

  “Where do you think you’re going?” Eric says, his smile widening as he shifts his body along with hers. He doesn’t have any trouble keeping her under control due to the constr
aints on her legs and arms.

  Tory does manage to turn herself around, so that her back is now against the wall, but it doesn’t do her any good. Eric keeps his fingers planted firmly inside her pussy, even managing to continue banging her as she tries to escape.

  Tory drops to the floor, her butt on the ground, but Eric moves along with her, finger-fucking her more aggressively now due to the increase in leverage he has over her.

  Tears are streaming down Tory’s face as she begs him to stop. But her face paints a different picture than her words; it’s fixed in a mask of pleasure, ecstasy even, and the cries coming from her mouth are ones of enjoyment, not pain.

  “Please stop,” she says between deep breaths. “Please. I need . . . a break. Please!”

  “I thought you said you could handle anything,” Eric says, still not letting up in the least even though his forearm is starting to burn with the effort.

  “Not this,” Tory says, her chest still heaving uncontrollably. It’s a wonder she can even form words. “Not this. It feels . . . too good.”

  “Too good? I didn’t even know that was possible.”

  “Neither did I,” Tory says. “But it does.” She groans and shudders again as another orgasm passes through. “Please. I’ll do anything you want. Just please . . . I need a break. I’m begging you.”

  “You’ll do anything?”

  With her eyes opened wide with hope, Tory nods her head vigorously. “Anything. Without complaint.”

  Eric stops banging her but keeps his fingers planted firmly inside her pussy as he pretends to think about her offer. In reality he’s thinking about how curious it is that pleasure can works just as well as pain—if not better, in Tory’s case—when it comes to breaking someone. It’s something he’s never considered before. But it’s definitely something he’ll keep in mind for the future.

  For now, however, there are more important issues at hand. Like continuing to impart his will upon Tory, for example.

  With their faces mere inches away, Eric offers a wicked smile, and says, “Sorry, but I’m having too much fun right now,” then goes back to slamming his four fingers inside her pussy.