24 Aggressive & Filthy Stories 2

by Heather Monroe

  Not that Holly cares. She likes the confusion in his eyes, the discomfort that’s plain on his face. She gets off on it. In fact, you could say that it’s the real reason she does what she does; not just for the physical sensation that comes from it, but the mental stimulation too.

  Holly sits atop her desk and looks down at Scott. Her legs are slightly open, giving him a straight shot up her skirt. She wants to see how he handles the view.

  “Do you know why I called you into my office?” she asks.

  Scott shakes his head. His gaze is continually shifting between looking up at Holly’s face and peeking at what’s between her legs. (Which is flesh only; she conveniently forgot to put on any panties this morning.)

  “Really?” she asks. “No idea at all?”

  He shakes his head again but he’s also starting to blush.

  “Now, why don’t I believe you?” Holly asks, tilting her head sideways and smirking knowingly at him. “Are you sure you have no idea whatsoever?”

  Scott shakes his head yet again.

  “You know what I think?” Holly says, climbing to her feet then immediately dropping to her knees in front of him. “I think you’ve heard all the stories from the other guys and you know exactly why I called you in here. That’s what I think.”

  Holly reaches out and grabs Scott’s waistband. He quickly scrambles out of the chair, knocking it over in his haste. He tries to back away from Holly but she stays right with him, shuffling on her knees as he moves backwards, her hands still clinging to his waistband. Eventually she backs him up all the way to the wall.

  “Nowhere to run to now,” she says, smiling like a demon up at him.

  He just stares at her, his eyes wide, his breath catching in his throat.

  “What’s wrong?” Holly asks, her excitement growing. She loves messing with men, especially shy ones. It gets her off. “Do you not like women?”

  “It’s not that,” Scott says, barely able to spit out the words.

  “Then what is it?” Holly asks as she slowly undoes his belt.

  “It’s just that . . . that you’re—”

  “The vice-president of the company?” she volunteers for him, slipping his belt off his waist.

  “Yeah,” he says.

  “That just means you should be going out of your way to please me even more,” Holly says as she drops his belt onto the ground. “Not denying me what I want.”

  Scott sighs in defeat. She has him there. Her logic is unassailable. Just like it always is in this situation.

  “I guess you’re right,” he says.

  “Of course I am,” Holly replies. She undoes the top button of his pants and goes to work on his zipper. “So just relax and go with the flow, all right?”

  He takes a deep breath, lets it out slowly and nods his head.

  “That’s a good boy,” Holly says as she pulls his pants to the ground.

  Scott’s raging boner is sticking straight out, hard as a log. His cock isn’t huge but that’s not a problem. Size only matters to a certain extent. As long as it’s not tiny that’s all that matters. And Scott’s isn’t tiny.

  “You have a beautiful cock,” Holly says, looking up at him. “Do you mind if I suck on it?”

  Before Scott can answer, Holly takes his cock in her mouth. She already knows the answer to her question anyway.

  She works Scott’s cock for a little while, sucking on the tip while jerking him off, getting him warmed up, then starts sucking it more aggressively. She takes it progressively further down her throat, bobbing her head forward and back, her eyes locked on his, maintaining eye contact. It isn’t long before his cock is disappearing in her mouth with every thrust, tickling her throat, filling her up, making it difficult to breathe.

  Holly easily takes him all the way down a few times, then holds his cock in her throat, deepthroating him for a full tens seconds before pulling off. Her mouth is filled with saliva and she spits it on his cock then starts jerking him off again.

  “You like that, don’t you?” Holly says, staring up at Scott while working his cock with her hand. “You like it when I deepthroat your cock? When I choke and gag on it?”

  Scott nods.

  “It makes you want to cum all over my face, doesn’t it?” Holly says, getting off on his discomfort.

  Scott nods again.

  “Then just wait,” she says. “Because this is just the beginning.”

  Laughing softly, Holly drops down onto the back of her legs and slides in closer to Scott. Then she goes to work on his balls, licking his sack, taking one of his testicles in her mouth, sucking on it for a moment, gargling it, then doing the same thing to the other one, all while still continuing to jerk him off.

  “What about that?” she says, looking up at him with a smile. “You like that too?”

  “Yes,” he manages to croak out. It’s the first time he’s talked since his pants have come off.

  Smiling wider, enjoying herself immensely, Holly grabs ahold of his sack right above his balls and squeezes, capturing his testicles in a tight pocket. Then she takes both of his balls in her mouth and sucks hard.

  Scott makes a soft sound and his legs buckle just a little bit. Holly can feel him tensing up so she pops his balls out of her mouth.

  “That too, I assume?” she says.

  Scott’s nod is more emphatic than ever.

  “Good, because I’ve got more where that came from,” Holly says. “But first you have to do some things for me. Okay?”

  He nods again.

  Holly stands up and grabs ahold of his cock and uses it to lead him over towards the couch set against the far wall of her office. Then she grabs a throw pillow from the couch and drops it on the floor.

  “Lay down on your back with your head on the pillow,” she says.

  Scott does as he’s told.

  Holly positions herself so she has one foot on each side of his head, her body directly above his face. She pulls her skirt up over her waist, revealing her neatly manicured pussy. Then she slips two fingers inside herself. They slide in easily; she’s already soaking wet. She works her pussy with her fingers while staring down at Scott.

  “Do you like my pretty little pussy?” Holly asks.

  Scott nods.

  “Do you want a closer look at it?” she says.

  He nods again.

  Holly squats over him, one leg on each side of his head. Her pussy is hovering a couple of inches above his mouth. She’s still banging away at herself, working her pussy with her fingers.

  After she’s got her fingers soaked with her juices, Holly pulls them out of her pussy, then bends down a little more and sticks them in Scott’s mouth.

  He sucks on her fingers, licking Holly’s pussy juices off of them.

  “There you go,” Holly says. “Lick them clean. That’s a good boy.”

  Once Scott is done, Holly pulls her fingers out of his mouth.

  “Did you like the taste of my pussy?” she asks him.

  Scott nods his head for what seems like the hundredth time since entering her office.

  “Well you’re in luck,” Holly says. “Because I’m going to give you a chance to get your fill of it.

  She grabs a handful of his hair and lift his head until his mouth is pressing up against her pussy.

  “Lick it,” Holly says

  Scott does as he’s told, going after her pussy with serious intensity, not holding back at all.

  Holly lets him work on her pussy for a few seconds before dropping his head back to the pillow.

  “Not bad,” she says. “Not bad at all. But I need a little more from you before I give something back. Have you had a woman sit on your face before?”

  Scott shakes his head, adding a quick “no,” for good measure.

  “Ooohhh, I get to pop your cherry,” she says, smiling. “Lucky me.”

  And with that, Holly drops down to her knees so her pussy is right on top of Scott’s face. Then she goes back to work on herself,
rubbing her clit this time while she smothers Scott with her ass and pussy.

  “Holy shit that feels fucking good,” she says. “But do you know what would feel even better? If you stuck your tongue out.”

  Scott does as he’s told.

  “That’s what I’m talking about,” Holly says. Still rubbing away at her clit, she grinds her pussy onto Scott’s mouth and starts riding his rigid tongue. “Right there, baby. Right fucking there.”

  A mini-orgasm washes over Holly but she doesn’t slow down one bit. If anything, she rides Scott’s face more intensely as she cums.

  “Fuck, fuck, fuck,” Holly hisses as her pussy squirts juices onto Scott’s face. She holds her breath for a couple seconds before letting it out in a rush as the orgasm passes.

  “That was pretty fucking good,” she says, lifting herself off Scott’s face, giving him a chance to breathe. “How was it for you?”

  “Fucking great,” Scott says between deep breaths. He’s smiling widely. It’s the most excitement he’s shown so far.

  “I take it you liked it?” Holly asks, matching his grin.

  “I fucking loved it,” he says.

  “That bodes well for you future,” she says. “Not only with me, but with any woman. It’s hard to find a man who truly enjoys getting smothered by a woman’s pussy.”

  “Really?” Scott says.

  “Hell yes,” Holly replies, sitting on his chest now, staring down at him. “In fact, you did such a good job that I’m going to do a little something for you now. How does that sound?”

  “It sounds awesome,” he replies. “But to be perfectly honest, I’m not sure how much more I can take.”

  “You’re close to cumming?”

  He nods sheepishly.

  “Don’t fret it,” Holly says. “Just sit back and relax and let me do all the work, and when you’re ready to cum, just let me know and I’ll take care of the rest.”

  “Sounds good,” he says.

  Holly scoots her body down until she’s squatting over Scott’s groin. Looking directly at him, she undoes the last couple buttons on her blouse. Although her shirt is still on, her tits are now free and visible. In fact, Scott can’t seem to take his eyes off them.

  While Scott stares at her tits, Holly grabs ahold of his cock, holds it straight up, and lowers her body onto it.

  Scott lets out a low groan as his cock easily slips into her wet, waiting pussy. Knowing that he doesn’t have much time at all before he cums, Holly starts working his cock immediately, putting her hands on his chest for leverage and expertly moving her body so that every time she drops down on his cock it goes a little bit deeper inside her.

  It isn’t long before Holly is bouncing on Scott so hard that his cock is completely disappearing every time she gets the bottom. As his moans and groans grow louder and more insistent, she increases the intensity of her gyrations until she is slamming her body down onto him with some serious aggression.

  “You like that?” Holly says, staring down at him. “You like it when I bounce on your cock?”

  Scott nods. His face is screwed up in a mask of concentration as he tries desperately not to cum.

  “Here, try these,” Holly says, reaching down and grabbing Scott’s wrists and placing his hands on her tits. “Anytime you feel like you’re getting close to the edge, just squeeze them a little tighter, okay?”

  Scott nods and immediately wraps his hands around them, squeezing them with everything he has.

  “Oh my,” Holly says, surprised at his sudden strength. But she likes it. A lot. So much so that she thinks she may actually be able to cum again before Scott is finished for good.

  “That’s what I’m talking about,” she says as she continues impaling herself on Scott’s cock, slamming down on him with all her energy. She arches her back and grabs a handful of her hair and tilts her chin towards the ceiling.

  “That’s right,” Holly says, riding Scott like a demonic cowgirl. “Give it to me, baby. Give it to me. Right there. Fuck me, fuck me, fuck me, fuck me!”

  Her moans are growing more intense with every thrust. But so are Scott’s. And his hands are squeezing her tits even more tightly, which means he’s closer than ever to cumming. It is now a race to orgasm, one that Holly has to win if she wants to cum again.

  With this in mind, Holly takes more control of the situation.

  She grabs ahold of Scott’s wrists and leans forward, driving his arms to the floor, pinning one on each side of his head. With her newfound leverage, she continues dropping her ass onto Scott’s body, harder and harder every time, trying to drive him into the floor.

  “Shit, shit, shit,” Scott says through clenched teeth, his face a mask of concentration.

  Holly knows the look and the sounds coming out of his mouth.

  “Not yet,” she growls at him.

  “But . . . you said . . . I could cum . . . when I was ready,” Scott manages to squeak out.

  “I lied,” Holly says.

  Scott puts on a wounded expression.

  “Don’t you dare fucking cum until I do, understand?”

  Scott nods but it doesn’t hold any conviction.

  “I mean it,” Holly hisses, still hammering down on him all the while. “You’d better not cum until after I’m done with you or you’re going to pay the price. Got it?”

  This time Scott’s head nod is a little more convincing.

  “Good,” she says, her tone lightening. “Don’t worry, it won’t be long now. I just need to do one more thing, and I’ll be done in no time.”

  And with that, Holly releases one of Scott’s arms and runs her now-free hand under his chin and grabs him around the neck.

  “There we go,” she says, her excitement immediately kicking up a notch at his expression of surprise at her latest move. “That’s what I’m fucking talking about.”

  Dominating one of her underlings always gets Holly off like crazy and today is no exception. She’s quickly rising towards another orgasm. She just needs to take things one step further and she’ll be there.

  She releases Scott’s wrist with her other hand and rears back and smacks him in the cheek with it. His shocked expression exhilarates her.

  She smacks him again.

  “Take it, you little bitch,” Holly says, slapping Scott with one hand while choking him with the other. His face is two different shades of red, a lighter one from the lack of oxygen and a darker one from the force of flesh smacking flesh. “Take whatever I give you.”

  And Scott does, taking it without complaint as Holly works him over, bringing herself right to the edge of orgasm while doing so.

  “Holy fucking shit,” Holly growls as a massive orgasm begins to wash over her. She stops bouncing on Scott and is now just pushing her hips down on his cock, driving it as deep as it’ll go inside of her. She stops smacking him too, instead wrapping both hands around his neck and squeezing tightly as she cums.

  “Fuck, fuck, fuck!” she screams as the wave washes over her, sending juices squirting out of her pussy and causing her body to tense up. She holds onto Scott’s neck until the orgasm passes, then finally lets it go.

  Air rushes into Scott’s lungs and his face starts to regain its color.

  “Wow, that was fucking incredible,” Holly says, smiling down at him. “Are you okay?”

  Scott nods. His lips are even turned up in a little smile.

  “Wait a minute, did you actually enjoy getting beat up like that?” Holly says, her grin growing wider.

  “Yeah,” he says. “I think I did.”

  “Interesting,” Holly says, drawing the word out as she files that little factoid away for later.

  Most of the young men she takes advantage of can’t stand relinquishing control. It’s rare to find one that does.

  “So are you ready to cum yet?” she asks.

  Scott nods emphatically.

  “Then let’s see what I can do to help,” Holly says.

  She leans forward and lovingly
caresses Scott’s face and sticks her tongue into his mouth. With his cock still in her warm, wet pussy, they make out, while Holly starts slowing working her body up and down on Scott’s cock.

  After getting him back to where he was before she started taking control, Holly breaks off the kiss and leans back until she’s sitting straight up again. Then she works her pussy forward and back, shifting the angle of Scott’s cock. As he quickly rises towards an orgasm of his own, switches it up again and starts moving in a circular manner, staring down at him the entire time.

  “Do you like that?” she says. “Do you like how I work your cock with my pussy?”

  Scott nods.

  “Do you want me to work it faster?”

  He nods again.

  Smiling, Holly starts bouncing up and down on his cock, not quite as aggressively as before but still with some intensity. She reaches back and spreads her asscheeks, allowing her to engulf Scott’s cock more fully.

  It isn’t long before Scott is ready to cum. His face is again screwed up in concentration and he even utters “shit, shit, shit,” again, just like before.

  “Are you ready to cum?” Holly asks, still bouncing on his cock.

  Scott nods his head.

  “Yeah?” Holly asks.

  He nods more emphatically.

  Holly bounces on his cock a couple more times then climbs off just as Scott starts to cum. Holding his cock against her stomach, she jerks him to completion, sending his sperm shooting straight up onto her chest, some of it even getting under her chin.

  As Scott’s cum drips down her chest, Holly squeezes every last drop from his cock before finally releasing her hold on it.

  “Not bad,” she says, smiling at him. “You definitely have potential. But there’s one more thing that I need to know before I decide about your future with the company.”

  “What’s that?”

  “Whether or not you can cum multiple times in one session. What do you think?”

  “I don’t know,” Scott says.

  “Well, then let’s find out,” Holly replies. Smiling, she walks forward until she’s standing near the wall.

  Once there, Holly leans over at the waist, her hands on the wall to help her balance, her legs straight, muscles taut, her ass sticking out.