Blonde and Bossy

Brian slowly tensed his body, adjusting to Vanessa's slender hands over him. He stifled back a slight moan as she slowly slid her index finger into his puckering hole, gliding it in with a sensual, yet electrifying touch...

It all started about three weeks ago when Brian, the accountant at his companies' firm had been caught during office hours, flicking through endless amounts of femdom porn at work. He'd briefly minimised his browser before rushing off to the bathroom, not realizing that his boss had noticed his slack work attitude in the recent weeks. Vanessa had initially pinned it on the breakdown of Brian's most recent relationship, with a twenty-ish year old girl that had the looks of a dumb blonde, and unfortunately for Brian, the same kind of intelligence that came with the look. While Brian never really talked about his types and preferences in the office, it was pretty well known by most that he was almost a sucker for blondes, and so when Vanessa had been transferred from the firm's east coast offices, she'd always catch him occasionally taking a long, lusting glance at both her hair, and the supple and firm breasts they fell between.

However, in spite of his addiction to blondes, as always, Brian's work seemed to dip when his relationships would break down after a month or two, and then pickup after a week or so. This time however, there were two abnormalities, one, his relationship with the blonde girl this time got to around 5 months before ending, and the second being he was still producing a horrible work performance after a month. Vanessa wasn't usually the type to stalk her own employee's, but Brian was showing no signs of improvement, and so as he rushed out for a bathroom break she couldn't help but take a quick look at his computer.

She flicked open his web browser. Forty tabs of femdom related porn were lined up perfectly across, with the current browser featuring a woman's dildo tipped heel being implanted comically into her sub's anus. Vanessa unpaused the video, and focused intently on the woman's figure, also being a blonde, with a similar curved body figure to her own, dressed in business attire, thrusting her heels mercilessly into the sub, whose face was an ecstatic mix between pain and pleasure. As the thrusting continued, the mistress began to whip the slave, while continuing to pound into him with her heels, and getting Vanessa all the more turned on and feeling flustered. As the sub almost looked like he was about to cum, Vanessa heard the flush from the toilet. She paused the video, minimized browser again and walked right back into her office, her flustered appearance puzzling most of the employee's she walked past.

Brain got back to his cubicle, and laid back in his chair, opening up his laptop again. As he was about to press play on the video, he realized the video had been paused at a different point to where he left it. He poked his head above his laptop screen and surveyed the room for any giveaway looks or smirking. Nothing. Considering he knew the timestamp when he left for the bathroom wasn't the same as this one, there was no way it could've been incidental, or have continued to play without someone else's interruption, he was sure of it, and yet, there was no way he could ask anyone if they'd seen someone else access his laptop without them probing further, no way he could ask the IT department without his laptop being thoroughly monitored and scanned, and asking his boss, Vanessa was out of the question. Not only was he attracted to her, but being around her tended to make him lose control of his own words. After all, she held the qualities and traits of his on-paper ideal woman. "Well definitely the physical traits," he thought to himself. He snapped out of it, quickly exited his browser, and cleaned any traces associated with porn on his laptop. While he couldn't tell who it'd been, it certainly did leave him with an uneasy and yet humiliating thrill.

Vanessa eased herself into position across her lounge, phone in hand, and ready to make Brian's life an exquisite hell. She spent the next 5 minutes setting up a fake email account, and started typing an email to Brian about his daily office adventures. Within about 10 minutes she'd convinced him into checking himself into a booked hotel room across town; with a promise not to reveal any of the information to his boss (She'd almost chuckled in adding that part), provided he showed up. The best part of it was that Brian would be thinking it was blackmail extortion rather than his own boss "fucking him". A mischievous smile swept across Vanessa's face, as she gathered her toys and tools, setting up her trap for Brian.

Brian was worried. Not only had his worst fears of his porn consumption in the office been discovered, but on top of this, he still had no idea who it was that knew, and he wasn't even sure that they'd hold up their end of the bargain. Well... it wasn't like he had a choice anyway. He begrudgingly got into his car and drove to the hotel's address. The nightlife of this town was nothing notable, but every once in a while, you could find something or somewhere to spark your interest. "It's too bad it can't be one of those nights," Brian thought to himself. He pulled up alongside the curb and parked. Getting out of his car, and looking for any others around him. A light blue mini cooper that looked vaguely familiar sat on the other side of the road, and he tried to remember exactly whose car it was... *Brrrrt* His phone went vibrated. Another email, demanding to know where he was. He checked the time, realizing he was late. "Oh fuck," he muttered to himself, before hurrying into the hotel.

Getting the room key had been pretty easy, but weirdly enough; the hotel staff member giggled handing it to him. It didn't matter; he had to prevent his story from getting out. Sure, one person knowing wasn't too bad, but if his boss ever found out that he was using the company's time and resources on getting himself off every so often at work, not only would he lose his current job, but if any future employers were tipped off, he could kiss any kind of future employment in his field goodbye. Opening the door, he was greeted with a note on the bed that read, "Put the blindfold on if you know what's good for you". Brian was conflicted. On one hand, this could end up being some kind of kidnapping situation, and there was no way he was ready to die at his age. But, on the other, it would make some sort of sense for a blackmailer to not want him to know their identity... Aha! He would make sure the blindfold had just enough at the top for his eyes to see whoever walked into the room.

About five minutes later, Vanessa strode back down to the hallway, seeing Brain walk through the door. She'd done this routine before, with however more "willing" participants, so a few of the hotel staff already what was about to happen. Plus, she always tipped extra so most where happy to oblige. As she strode down the hallway, the tight, knee high black skirt rubbing against her butt, and the black suit against her voluptuous boobs. The sensitivity of her body, in addition to what she was about to do to Brian got Vanessa slightly flustered and excited all over. As she arrived at the door, and opened it, there she found Brian, sitting there with a blindfold, and could easily tell he could see her, by the reaction on his face that he tried to cut short, but was blunt clear to her anyway.

"Kneel". As Brian opened his mouth to object, Vanessa pressed her finger across his lips.

"Silence," she said. I don't want a word from my own employee that jerks himself off to porn during office hours, wasting the company's time and resources in the process. Of course though, if you've found that somehow you're in the morally correct position here." She then moved her face to Brian's making him ever so slightly more uncomfortable. "Please, do feel free to go ahead and contact my superiors, just as I'll show them your porn addiction, you can show them the emails you've got from a random stranger."

Brian's face began to turn red, a mix of both anger and embarrassment, and yet at the same time, his boner began to protrude through his jeans. "Oh fuck, please don't let her notice this," he thought to himself. It was too late though; Vanessa inched forward slightly, moving her face even closer to his own.

"Judging by the bulge in your pants however, I think my deal could benefit us both," said Vanessa. Brian then turned a much deeper shade of red, this time in pure embarrassment, while getting even harder. While Brian had always thought Vanessa was one of the hottest Blonde's he'd ever meet, he never thought a fantasy like this could come true.

Vanessa eyed Brian briefly once again, and paced back and forth in front of him. "Get on the bed and get your cute butt facing me," she commanded him. Brian obediently obeyed, and as Vanessa watched she picked up the bottle of lube from underneath the bed, and gently applied it to her finger. Brian's hole gaped slightly, as Vanessa's finger plunged into it. Brian let out a low moan in response.

"Mmmmmm," Vanessa purred back. "I had a sense you were into domination, but I never thought of you as one to be pegged."

"What?" Brian asked, between his moans.

"Oh, you'll find out soon enough," Vanessa replied, focusing intently on getting at first two, then three fingers into Brian. As she continued to thrust, Brian began to thrust back towards her fingers, in a rhythmic motion.

"Oh fuck Vanessa... keep going," Brian said. Vanessa began to thrust back harder, before pulling out, eliciting a small whimper from Brian.

"Oh don't worry, I'll give you something even better," she said chuckling, before slapping his ass playfully.

Vanessa once again went below the bed to retrieve the dildo. Pulling down the sides of her skirt, she placed the dildo between her strap-on holder. "Now close your eyes Brian, this one's a bit bigger than my fingers." Vanessa then rubbed the dildo with the lube, making sure to add extra lube to the tip of the dildo. "Well Brian..., let's hope you'll be able to sit straight tomorrow," she said. Brian briefly reacted by clenching his tight hole, to which only made Vanessa fluster even more, licking her lips in glee. Moving her strap-on harness forward, she gripped the strap-on, and began to beat it against Brain's cheeks, to a rhythm. "Mmmmm, I hope you're excited Brian, this is the moment you've been waiting for, all that femdom content finally amounting to something right?" Brian's face flushed a deep red, biting his lip, but at the same time knowing she was right. As the tip of the dildo found its way into Brian's starfish, he began to tightly grip the bedsheet. "Hold still, this'll only hurt a bit..."

The initial thrust of her strap-on shocked Brian, entering a world of immense pain. "W-wait, give me a sec to adjust," said Brian. Vanessa grabbed his hair, lightly pulling it, and leaning into Brian, whispered:

"No, trust me, I promise you, just take it for me, and it'll be okay."

She then leaned back, before thrusting even deeper into his hole. Brian felt the wave of pain hit him again, as it penetrated deeper, but a slight pang of pleasure followed. "Go... deeper," Brian mumbled, while gritting his teeth.

"What do you mean by deeper?" Vanessa teasingly asked. "Are you getting a kick out of this Brian? Is your puckering hole asking for a nice, big, thick strap-on?" Brian, gritting his teeth, responded with a single nod. Instantly, he felt a surge of overwhelming pain, as Vanessa's entire strap-on began to plunge into his hole. Thrusting again and again, the pain caused from Vanessa's strap-on began to ram into his prostate, being replaced by pleasure. As the thrusting continued, Vanessa began to feel her juices trickling out of her vagina.

"Oh, oh I'm gonna cum Vanessa," exclaimed Brian. Vanessa grabbed his hair once again, pulling back even harder, and thrusting even deeper. "Oh fuck Vanessa, Oh fuck," Brian continued to yell, completely forgetting Vanessa was his boss, his only real connection to the world at this point being the strap-on and his hole. As he was about to reach climax, Brian gripped the bed even tighter, letting himself get carried along, and feel each and every thrust. "F-Fuck I'm cumming," he exasperated, and on cue, spurts of cum soon followed their way out of his cock.

Vanessa held her strap-on in Brian's hole as he came, waiting him to cum himself to a complete slump first before removing her cock. She motioned for Brian to turn over, as he recovered from the pleasure waves of his orgasm. "I'll give you two options Brian. We can pretend this never happened, go back to our normal way of work. Obviously, your porn addiction doesn't seem like something you can control without the assistance of someone else, so I'm pretty sure it's safe to say your poor performance is eventually going to land you out of a job," said Vanessa, letting a silence of command settle in first. "Or of course, we can continue this little arrangement," she said, slapping his ass. "So what will it be Brian?" Letting your boss walkover and dominate you, or getting fired? Brian, having finally come to his senses again, became red in the face. "I think this arrangement... w-would probably be a lot better". "Good" said Vanessa, before lowering her skirt and panties. "Now lay down, I want you to eat me out. I haven't cum yet and I'm sure that, we can both see that seems a little unfair now don't we?"

"Yes Vanessa."

"In here, it'll be yes mistress."

Looking up to face her pussy, Brian whiffed the smell of her vagina, and briefly sighed, before replying:

"Yes Mistress."