Embezzlement Punishment

Deborah Hennessy waited patiently at her desk, going over her finances after having just called her once trusted assistant, Malcolm Gemmell, about the spending he was doing. She put her faith in him to invest her money wisely on her behalf, but after seeing how much he had been taking from her business accounts she needed to finally put her foot down on the matter.

When her secretary allowed Malcolm in her office, she looks up from her paperwork to see the young man with his slicked back hair and gray three-piece suit approach her. "You wanted to see me, Deborah?" he casually asks the much older businesswoman.

A smirk forms on Deborah's lips as she stares at the handsome young associate. "Please, Malcolm, call me Ms. Hennessy today." Studying his expression, Deborah could tell he knew he was in trouble. "Have a seat, please."

Malcolm nervously sits in one of the two chairs in front of Deborah, wondering just what he could be in trouble for. He hadn't done anything wrong, outside of taking a few thousand dollars in an attempt to start up his own company outside of HiJaque. He speaks up, asking, "Ms. Hennessy, am I in trouble?"

"I suppose that depends on your definition of 'trouble'," she claims, using air quotes. "See, the other night I was looking into the company's funds, and as I looked through our transaction history I spotted several transactions that almost put that account into the negative numbers." Holding up a printed statement of her account, Deborah points to all of the transactions circled in red. "These, Malcolm, are all ATM withdrawals." she says, her smile wearing off. "And all of these withdraws are done with your company credit card. You've been embezzling my money for what, exactly?!"

Malcolm's face turned red as he looked at the paper. He could tell he was busted, having hoped that this would go unnoticed. "Ms. Hennessy, I can explain!" He exclaims. "They were just a few small transactions, that's-"

"A lot of transactions, Malcolm." Deborah interrupts. "And all of those small transactions add up to a LOT of money wasted!"

"Alright, alright, I'm sorry!" shouts Malcolm. "I thought I could start something up on the side and get away with it, that's all. I thought with so little being taken out at a time I'd get away with it. Just...it's no big deal."

"No big deal?!" exclaims Deborah, her hand slamming down on the top of her desk. "You almost cost me this company and my best employees, Malcolm! And I don't even know what to do with you at this point!"

Holding his hand up, Malcolm sighs. "Look, if...I haven't spent that money." He says. "All of it is still sitting in my safe back home. I can just give you that money back and everything is fine, right?" Malcolm begins to grin nervously, afraid of the worst possible circumstances for himself. Unfortunately for him, Deborah shakes her head in shame, which made Malcom even more worried. "Come on, Ms. Hennessy, there has to be SOMETHING I can do to make this up to you!"

Deborah's eyes study the sitting young man, her stern expression still on her face. Slowly a smile forms, and she wags a finger upwards at him. "Stand up." she says, twirling her finger in the air. "Then spin around for me."

Confused, Malcolm does as he's told, slowly spinning in place in front of his boss. "Now," Deborah continues, "I want you to take off your pants and bend over."

"O-Okay...?" stammers the young gentleman. Undoing his belt and pants, he lets them fall before turning to Deborah with his ass in plain sight for her. She bites down on a pen, enjoying the view. "Is...is this all? You wanted me to moon you?"

"Mmm...it's a very nice ass." Deborah compliments her associate. "Now spread your cheeks out."

"What?!"

"You want to do anything to keep me from calling the police, right?" Deborah asks in a devilish manner. "Spread. Your. Cheeks."

Sighing, Malcolm rolls his eyes before he puts a hand on each ass cheek and opens them up. Deborah can't help but laugh. "What's so funny?" he asks.

"It's such a virgin ass!" Deborah says through her chuckles. "Oh my goodness! It's a wonder that a woman hasn't pegged you yet, you have a nice little tushie!" Soon Deborah moans as she lowers her hands on her lap, under her desk where Malcolm wouldn't see them as she caresses her crotch from over the fabric of her skirt.

"Pegged?" asks a confused Malcolm. "Isn't that just penetrating the ass?" Deborah nods. "But...I thought only gay guys did that stuff."

Deborah lets out another laugh. "Oh, Malcolm, you really DO have a lot to learn about the world, don't you?" The owner of HiJaque pulls her chair out from the desk before she sits up. Rounding the desk Malcolm can see his boss's legs. He also noticed that there was something about her skirt that puzzled him. It was as if something was poking out from underneath it.

Then it dawns on him just what it is. "Ms. Hennessy, is that a penis?!"

Nodding with the biggest smile on her face, Deborah pulls back on the skirt, the fabric brushing against the head of her cock until it's visible for the male associate to see. There was a clear liquid that dangled and dripped from the slit of her shaft as she walks over to him, the cock bouncing in the air with every step she takes. It looked so hard, as if it was at it's peak while Deborah held herself back from coming. The shaft was vein-y, and he could swear the head was pulsing along to the beat of her heart.

"Wait..." Malcolm spoke up, "You're not going to stick that up my ass, are you?"

Deborah lets out a chortle as she stands behind Malcolm, pressing her hand against his backside. She feels how smooth his skin is, and could hear her associate let out a deep sigh as her fingertips massaged against his cheeks. "Well what else am I supposed to do with it, silly? I can't exactly suck myself off now, can I? I'm not exactly THAT flexible, you know!" As she undoes her blouse, exposing her breasts, her gaze goes down to between his legs, admiring the size of his scrotum and what she could see of his cock. "Besides, if you don't I could always call the cops and let them handle everything from here on out."

Malcolm let out a defeated sigh. "Alright, go ahead..." he grumbles, his hands still spreading out his cheeks for Deborah.

Squatting on the floor, Deborah looks at his anus, stroking her cock as she takes in the sight of his virgin ass. The owner brings her thumb up to his hole, massaging it against the exit point. She hears Malcolm inhale through small hisses, preparing himself for the worst. Although in fairness he stopped looking back and believes it to be the head of her shaft pressing against him. Deborah simply chuckles, finding it cute that her associate is acting in such a manner.

Finally Malcolm's boss pushes her thumb inside, venturing up to her knuckle while Malcolm lets out a gasp of fear. "Oh Malcolm, please." she says with a smile. "You're not the first I've done this with, you have my word I know what I'm doing."

"I just...I never thought I'd be doing something like this in my life." Malcolm replies, grunting as her thumb moves around inside his anal passage. He tightens up his ass, surrounding her thumb tightly, but it only presents an impressed hum from Deborah.

"Oooh, that's nice, Malcolm." she says. "I can feel a pulse. Your ass has a pulse and it's pressing around my thumb..." Malcolm wasn't all that sure, but he could swear that Deborah was getting aroused by that fact. He could hear skin rubbing against skin, likely her hand still stroking her herd cock in anticipation for when she finally gets it inside his ass. As her thumb presses against the roof of his rectum, Malcolm inhales through his nostrils, feeling her fingernail pinching into him. His body locks up from the unexpected pain it presents him.

Slowly her thumb makes its way out of Malcolm's ass, making the business associate groan and flex his ass muscles afterwards. He really couldn't believe that her thumb just went up his rectum.

"So how did that feel, Malcolm?" asks Deborah as she leans forwards, holding her hand up to his ass for balance.

"It was...different." he replies, unsure how to feel. "It's just...I never thought I'd be having things up my ass like this."

"Oh Malcolm..." Deborah shakes her head as she sighs. "I feel like you're going to need to let this feeling of anal penetration go. There are lots of men that love having a woman fuck them in the ass, whether it's my cock or a strapon."

"Honestly it's a lot to take in." Malcolm replies.

"I understand. Which is why I'm just warming you up." With a laugh Deborah sticks her tongue out, leaning forwards enough that she pushes it against his ass. Malcolm then moans as he feels his boss flick the tongue up and down as it touches against his anus. Her saliva struck against his rectum, getting him nice and wet.

As Malcolm allowed his boss to do with him as he pleased to avoid any trouble for his embezzlement, he soon felt his own cock hardening up. This brought a lot of confusion to him, such as why he was getting hard from the experience. He seriously was beginning to question himself.

"Ms. Hennessy..." Malcolm moans, "I'm getting hard. You, um, you wouldn't mind if I could...?"

"Let you fuck me?" Deborah interrupts, finishing his question for him. "We'll see how that goes. But I'm the one giving orders for now, understood?"

"Yes ma'am..." he sighs.

After Deborah gives a quick peck to his asshole, she stands up, her hand still stroking her cock. "Okay, Malcolm. Let's get you comfortable now. Lean against my desk."

With a nod, Malcolm does so. He bends over, his elbows resting on top as his ass is presented to his boss. With a grin Deborah steps forward, sticking the head of her shaft against the ass of her associate. Slowly she rubs the head against his corn hole, using her saliva to help lubricate it before it makes it's entry way inside the young man and breaks his anal cherry. Malcolm bites down on his lip, a soft whimper escaping as he prepares his anus for Deborah to pop it in.

Once he feels the head of her shaft push inside and enter his ass, Malcolm's mouth opened with no sound escaping. He certainly felt like he'd be screaming as Deborah continues to press onward, her eleven inch long cock snaking up his ass. She continues to thrust inside until her hips meet against his cheeks, and she lets out a moan of relief. "Mmm, I think I stretched you out good, Malcolm. What do you think?"

As he takes deep breaths, Malcolm holds onto the desk tightly, his teeth clenched together. It was not a feeling he had been accustomed to, and yet he seemed to take a bit of liking to it. Then he begins to feel Deborah thrust against him, her hips rocking against his backside as she tries pump her cock in and out of his asshole.

After a few minutes, Malcolm seemed to calm down. He still wasn't comfy on the idea of anal sex when he was the one taking it, but with some time his ass didn't feel like it was being stretched out (mostly because it didn't need further stretching). "I guess I'm doing alright..." Malcolm finally answers, grunting as Deborah continues to push against him. With every thrust she made Malcolm could feel the tip of his own cock hitting against the front of the desk, the head bouncing against the stained wood. It was getting him harder, and he could feel the clear liquid pooling out, creating a tiny string that connected from his slit to the desk where his nub continued to dab against.

Malcolm lets out a gasp of pain as he feels Deborah slap her hand down on one of his ass cheeks, gripping it tightly in her hand afterwards. "Mmm, such a nice padded ass you have, Malcolm." she says gleefully. "There's so much cushioning back here. You should be proud of yourself."

"Thanks...I think..." Malcolm replies.

Deborah leans into him, whispering into his ear. "And how are you feeling? Is your cock hard? Would you like to cum?"

Nodding his head in response, Malcolm answers, "Yes Ms. Hennessy. Please, let me cum..."

As if teasing him, Deborah taps her chin as she thinks it over, her cock still pushing between his cheeks and rubbing against his anal cavity. "Hm...well, I guess you've been good enough to deserve a little treat. But first..." Still leaning over him, Deborah brings her teeth up to his ear lobe, nibbling away at the soft tissue. Malcolm's eyes rolled up, the sensation of chewing on his ear lobe releasing a feeling of ecstasy he had never realized existed until that moment.

While her shaft still thrusts inside him, Deborah lets her hand reach around Malcolm and grab his cock, stroking it up and down. Malcolm licks his lips, moaning as her surprisingly soft hands massage his meat rod, enjoying her touch. But as she does so, his boss chuckles to herself.

"Hey!" Malcolm shouts, visibly upset and embarrassed by her amusement. "It's not funny, I'm like six or seven inches!"

"Oh, Malcom, I'm sorry," she says, "It's just that I imagined you'd be so much bigger! You're about average at best!"

"That's still good, right?" he asks, his eyes shut as he can feel his erection peaking. His cock was close to climaxing, but he tried not to cum just yet.

"Well, I suppose it's not the worst you could be." Deborah sighs, rubbing her other hand across the back of his neck. "But I don't think you'd give me the same satisfaction that I feel I'm giving you. You know, because you're enjoying having a woman's cock inside you, apparently."

"I-I guess so." Malcolm replies, a little embarrassed. "It...it still doesn't mean I'm gay!"

"Of course not..." Deborah replies sarcastically, rolling her eyes while he couldn't see her.

Grabbing the collar of his shirt, Deborah pulls back to bring Malcolm's back against her exposed body, her nipples rubbing against his suit's jacket. She blew into his ear, once more bringing that feeling of excitement to his body that truly brings his cock to a full erection, throbbing as it begs for release. Her lips press against his neck, tasting the rough texture of his skin. All of this attention almost made the young associate forget that the reason he was so aroused was because of the cock his female boss had placed up his ass.

"Ms. Hennessy?" Malcolm asks with a groan. "I'm going to cum!"

"Not a problem, Malcolm." was his boss's response as she speeds the pace of her hand as it runs down his shaft, rubbing it as fast as she could. Malcolm's back arches as he stands upright, grunting as he shoots his wad against the desk. His teeth clenched, the assistant feels every squirt pulse out of his shaft, the white goo making a puddle as it slowly trickles down the desk.

As Malcolm pants heavily, Deborah smiles as she pets his ass. "How did that feel?"

"It was...wonderful..." he replies weakly.

As Deborah chuckles again, she continues thrusting into Malcolm again. "You know, that's just another benefit of anal sex, Malcolm. Your prostate is where things REALLY get exciting, and you know where that is?"

"In my ass?"

"Now you're getting it." Deborah says with a grin, giving his ass another slap. "Oh, god, I think my cock could use your ass as a new home! It feels so snug and cozy inside of you...nnnngh!" As she spoke, her own cock was throbbing inside of Malcom's ass, the veins pumping so much blood into her groin for such an occasion. But she didn't want to cum so soon, she felt like she had only gotten started.

"Ms. Hennessy?" pants Malcolm. "Are you alright?"

"Y-yes, Malcolm, I'm fine!" she swears, biting down on her lip. The boss's muscles tightened up, trying to hold back the feeling as best she can. Her cock was so warm inside Malcolm, she refused to leave his anus so soon. She held on for only a minute more of anal penetration before her own cock began to peak, and she was ready to let out her own seed. "Oooh, shit!" she says. "I'm going to cum myself!"

Pulling out of Malcolm's ass, Deborah strokes her own cock before she allows her jizz to shoot onto Malcolm's backside. She aims it like a fire hose, making sure her cum spreads across his ass like icicles on the side of a house in winter. Deborah growls through her teeth until she finishes her climax, looking at her artwork in admiration. Malcolm's ass resembled that of a peach with icing on top of it.

With nothing else coming on top of him, Malcolm finally looks back at his boss."So, um...is that...are we done here?" Malcolm asks as Deborah collapses into one of the chairs in front of her desk. "No need to call the police or fire me or anything?"

"No...you're fine, Malcolm." Deborah says just before laughing before tacking on, "For now, anyway."

"Wait...what?" Malcolm looked at Deborah with surprise.

"Oh please, Malcolm! You didn't think this was going to be a one and done deal, did you?" she cackles. "If you want to keep working under HiJaque's employ AND keep the police off your ass, you might need to do me these favors every now and again. You're not off the hook THAT easy!"

"Shit..." was all Malcolm could mutter.

"Now," Deborah says sternly, "I expect to see that cash first thing in the morning. Also, I'll need you to return that company credit card along with it."

"Yes, Ms. Hennessy." he replies with a defeated sigh. He bends over to grab his pants and pull them up, but immediately remembers that there's semen running down his backside thanks to Ms. Hennessy's shaft. "Um...Can I have a towel or something to clean my ass at least?"

Shaking her head, Deborah replies, "No, I'm afraid you're just going to have to pull your pants up and walk around like that the rest of the day."

Malcolm mumbles under his breath, pulling his pants back up as he awkwardly walks out of her office, trying to keep her spooge from touching against his underwear. After he leaves, Deborah straightens out her own clothes, then approaches the cum stain Malcolm had left on her desk. Scooping a bit onto her finger, she licks it up, letting it sit in her mouth for a bit. "Very nice..." she says. "Maybe next time I'll have him clean it off himself."