Bitchy Boss 1

At the age of 23 I was in my second year of a graduate trainee scheme with one of the UK's more successful tech companies. It was a sought after position, with excellent remuneration and great prospects. But it came with a demanding, high pressure, workload.

The way the scheme worked was we rotated around a number of directorates, getting exposure to a variety of functions and ways of working. It also meant we were working with and for several different teams, typically in 6 month slots.

I'd been in my current directorate for a few months and was, unusually for a trainee, away in San Diego on a tech conference. Invites to these were typically reserved for more established employees. Partly as they were something of a junket and considered a "reward" for good performance. But also because there were almost invariably sessions at which we would ply our wares to prospective new customers. And trainees were not considered skilled or experienced enough to do this.

The directorate was headed up by Chrissy. The only woman director in the company and perhaps something of an anomaly across the whole, male dominated, tech industry. She was in her mid 40s, sharp as a scalpel and with the most fearsome reputation imaginable. Even the other directors seemed scared of her. To the junior employees, myself included, she was someone we tried our very hardest to stay on the good side of. Though, ideally, we'd try to avoid her completely.

Just on this trip alone she'd reduced one of the more senior product managers to a gibbering wreck as she berated him, publicly, for what she felt (in fact she was probably correct) had been an ill prepared, inaccurate, client pitch.

The other stand out feature (and forgive me for presenting a cliched, sexist, stereotype, but I'm afraid it's true) was that Chrissy was attractive. Extremely attractive in fact. And did not conform at all to the nerdy, tech, stereotype.

Immaculately sleek jet black hair, albeit cut in quite a severe bob. Flawless skin and a slim, tight, toned, figure. Whilst she never dressed to draw attention to it even her conservative business clothes did not hide the peachy arse and firm, still perky, tits. Some of this, I guess, was due to good genes. But much of it down to the fact that she trained hard, with a reputation for pushing herself as hard in the gym as she pushed the team she led.

So she stood out, in almost every way.

By the last day of the conference the majority of our company delegation had gone home. But a small team, led by Chrissy, had done a pitch for some new business to a huge US client. She'd specifically asked for my input and, surprisingly, had got me to present. Albeit just a small part. I wasn't the most technically gifted, but I knew I was good on my feet; more articulate and assured than some of my more techie colleagues.

The presentation had gone well and I'd felt comfortable in the part I'd played. Remarkably, even Chrissy had complemented me on my performance. The bulk of the team went straight to the airport, to pick up our flight home later that afternoon. But Chrissy and I drove back to the hotel, in a hire car we'd rented. We'd left some of our promotional materials there and also needed to settle the account for our week's stay. Chrissy was going to attend to the latter whilst I was there as the "muscle" to hump stands and boxes down to the car.

Pulling in to the underground garage of the hotel I found a parking spot in the far corner of the lower of two levels. It was early afternoon and surprisingly quiet. As we pulled our laptop bags from the boot (or trunk as I guess they called it in the States) I heard footsteps, echoing through the garage.

Turning round, with just idle curiosity to see the source of this, I was astonished to see two young guys come hurtling towards. They seemed slightly built, though one was over 6ft tall. With one of them brandishing a large knife, almost machete like in appearance.

Coming to a halt in front of us the taller of the two snarled at me, "give me those bags and hand over your wallets and watches," waving the knife just inches from my face.

His movements were judderey, he was licking his lips repeatedly, with dilated pupils. Clearly he was under the influence of something.

Initially I was more taken aback than scared. I didn't think San Diego was a particularly dangerous City. And the car park of one of the more up market hotels, especially in the middle of the day, certainly didn't seem like the sort of place where you'd expect to be waylaid by knife wielding junkies.

All of that said, I quickly appreciated the seriousness of the situation. I was just grateful that they had a knife (albeit a very large one) and not a gun. But, even without them brandishing a gun, from my time in some of the grubbier cities back in the UK, I knew better than to attempt any heroics.

The company would replace our computers, my Casio watch was worth less than £50 and I had just a few cards and about $100 in my wallet. Certainly nothing to risk my life over. I suspected Chrissy had much more expensive jewellery. But it would be insured. So discretion was certainly the better part of valour.

"Hey, no worries," I assured machete man, gingerly handing him my laptop bag and unfastening my wristwatch. "Just stay cool, I'll give you what you want and you can walk away."

Chrissy, on the other hand, was less compliant. She was either braver, or more reckless. I felt the latter.

"No way, we are not handing you anything," she spat out at them.

Initially this seemingly unexpected response surprised our two muggers and, momentarily, I though we may have got away with it. But, predictably, drugged up as it appeared they were, it just inflamed them.

"Shut up bitch, you'll do as you're told," the taller of the two slurred. "Let me give you some encouragement."

Moving towards Chrissy he gripped her tightly by the arms and tried to tear the watch off her wrist and the necklace from around her throat. At the same time his friend moved behind her and grabbed her breasts, tearing open her blouse and then groping her groin over her business suit trousers.

"What a piece of meat," he sneered, "let's get ourselves some of this," he suggested to his co-assailant. His accomplice then tried to kiss her roughly, whilst also pawing at her tits, managing to free one of them from the cup of her bra.

I'd been quite prepared to hand over our valuables. But there was no way I was going to stand by and see a woman assaulted, particularly sexually.

Flinging myself at the two of them the first thing I did was to try and wrestle the weapon out of their hands. Taken by surprise as they were I managed to loosen their grip, though one of them was able to use the handle of the machete to strike a firm blow to my head. Fortunately, in the act of doing this they dropped it to the ground. Showing admirable presence of mind, Chrissy kicked it out of reach, under the car. Though that caused one of them to fling Chrissy head first against the car bonnet, momentarily stunning her.

The two of them then turned on me. Slight as they were I was outnumbered and whatever drugs they were on seemed to be making them especially manic. One of them leapt on my back whilst the other tried to pummel me. They got in some good blows but, at the time, the adrenaline coursing through my veins meant I didn't feel them.

I'd done a few years of boxing as a kid. So, whilst I was not some accomplished pugilist, I had some idea how to handle myself. Shrugging off the fellow on my back I got in a few lusty blows of my own. Before the two of them stopped in their efforts.

Looking up, I saw hotel security come hurtling down the car park. They'd been alerted by another driver. Seeing them our assailants turned rail and ran, leaving us - and our valuables - behind.

Checking we were OK, the security staff took our bags, ensured the car was locked and ushered us up to reception. The hotel staff were extremely attentive, clearly embarrassed and concerned that an assault had taken place on their premises. They organized medical attention for us, though this was interrupted by interviews we gave to the police. Frustratingly the upshot of this was that we had missed our flights back to the UK. In fact, the medics were insistent that, given we'd both taken blows to the head, we shouldn't fly for a day or two. On the upside, the hotel advised that they would put us up in a suite and look after us as best they could. Chrissy had alerted the MD of our company and he was also adamant that we took it easy for a day or two and listened to the advice of the doctors.

Other than anticipating a break from the rigours of work I had nothing and no-one to rush back to. But I wasn't much looking forward to three days in the company of Chrissy who, as I said previously, was in some ways scarier than the junkies who'd attacked us. Though the vision, brief as it had been, of her tit spilling out of her bra had reminded me what an appealing (though sometime appalling) woman she was.

After we'd finally finished our police interviews and medical care, we unpacked in the adjacent rooms of our palatial suite, before meeting for a quiet dinner in the bar of the hotel. I'm bound to say that Chrissy was extremely mellow, in fact very subdued. Though she kept reiterating her gratitude to me for the part I'd played in looking after her. We barely spoke about work, but discovered a few mutual interests outside of it. Particularly tennis, which we'd both played at a reasonable level.

We had a light dinner with a few glasses of wine, before retiring to bed shortly after 10pm, both of us exhausted as the adrenaline wore off. I'd stripped off and was just about to fire up some porn on my iPad for a relaxing wank, before getting some much needed kip.

But just a few minutes after we'd said goodnight there was a knock on the adjoining door between the two rooms of our suite. Pulling on my boxer trunks, but nothing else, I opened the door with a degree of irritation.

That irritation dissipated somewhat as I took in what Chrissy had changed into. She had on a pair of sleeping shorts and a matching vest. The shorts were skimpy, showcasing her excellent, toned, athletic, legs. The vest was similarly brief, cut quite low with spaghetti straps and tight enough to suggest from the gentle sag of her breasts and the faint outline of her nipples that she was braless.

Whilst it wasn't some slutty negligee it was certainly sexy, showing more of Chrissy than I'd ever seen before - and had probably ever expected to see.

I took all of this in in an instance and was certainly not leering at one of most senior - and definitely scariest - directors in our company. Or at least I hoped I wasn't. But I'm sure Chrissy had recognized the look of approval I'd made as I gave her the once over, as brief as it was.

That said, perhaps she hadn't, as she appeared upset and close to tears. Though not, I hoped, because I was leching at her.

"Jack, I'm so sorry to bother you again," she began, hesitantly. Displaying an apparent vulnerability that I'd never seen, nor even imagined.

"I really hope you don't mind me asking this of you," she said, in hushed tones, with a distinct catch in her voice. "But could I come in for a minute? Then, after a long pause, "and would you just hold me before we go to sleep?"

Seeing the look of uncertainty, if not incredulity, on my face she continued. "I'm afraid I'm suffering a delayed reaction to the assault earlier. The shock is coming out and I just need a little comfort and physical warmth. I really do hope you don't mind? But please keep this between us," she concluded, with an embarrassed smile.

"God, of course not," I assured her, genuinely upset to see her like this, no matter how badly she'd sometimes treated us.

Pulling her to me I held her tightly. Almost as soon as I cradled her in my arms her resolve weakened and she began to sob. Huge racking sobs that shook her whole body. In fact, I could feel her legs start to buckle. So I led her to the bed and lay her on it, whilst continuing to hold her in my arms.

Burying her face in my chest she would stop for a few seconds, then start sobbing again.

"Oh God Jack, I'm sorry," she managed to snivel, "please hold me tight."

I carried on doing that. Doing my best to comfort her by stroking her back and gently fussing her hair. This seemed to be helping as her sobs were finally abating.

But now that my surprise was diminishing I was increasingly conscious that I was clad only in my underwear, with Chrissy wearing not much more. And that realisation was becoming more pronounced as Chrissy was now holding me as tightly as I'd held her. Her face still buried in my (quite hairy) chest, with her groin against mine. I wasn't fully erect (yet) but there was most definitely a stirring in my loins. And it seemed impossible for her not to notice this.

"Oh God, thank you. I'm so, so, sorry," she apologized, in between further snivels and sobs. "I feel so much better for you holding me." With this expression of gratitude helping to alleviate any concerns I had about her noticing my arousal.

Pulling herself up she gave me a kiss on the lips (there were no tongues and it was non-sexual, but a huge surprise nonetheless) as she looked deep into my eyes.

"You're so kind. I really appreciate this," she said softly, before burying her head back onto my chest, which she continued to snuggle against. Which she also, in the latest of a succession of surprises, lightly kissed.

"You don't need to thank me," I assured her, "you've gone through some real trauma, it's no surprise at all you feel wretched. I'm sure it's good that you let it out."

The top of Chrissy's head was level with my face as she buried herself in my chest. Taking her lead and perhaps not thinking this through, I continued stroking her hair but also reigned gentle kisses on to her head. God, she smelt delicious!

With hindsight, this was a risky thing to have done, as it displayed a real degree of intimacy. However I was, to a very large extent, just mirroring her actions.

Thankfully she did not recoil in horror and did nothing to stop me. Quite the opposite in fact as she snuggled closer against me.

"Oh Jack, this is lovely," she informed me, dreamily, "I feel so much better. I just feel so safe in your arms."

The situation was surreal. With Chrissy's docility and vulnerability quite astonishing. It was not something I'd ever have thought her capable off. Emboldened by her approval of what I was doing I was a little more emphatic in my kissing, albeit still of her hair/head. Though I remained gentle and soothing, there was a sensuality in my actions. But they were not, at this stage, overtly sexual.

That said, it was Chrissy herself who ramped up the sexuality. As I maintained my hold on her she edged up slightly so that her face, not the top of her head, was level with mine. And, at the same time began to slowly gyrate her groin against me. An action that rapidly led to a full erection. One she most certainly felt and actually took advantage of as she ground against it.

There was almost no communication between us, beyond some gentle oohs and aahs from Chrissy.

This lack of comms may have partly explained why I was in absolute turmoil. It appeared that I was getting clear signals to proceed with the seduction of my horny, MILFy, director. But, of course, that was the issue. She was my Director, with one of the fiercest reputations imaginable. Even setting aside the intricacies of sexual mores, post the me-too movement, I was massively conflicted in how and whether to proceed. So I played it very carefully and did next to nothing.

Unfortunately, the docile, gentle Chrissy I'd been observing couldn't last. As I was taking things slowly and ensuring I did not push any unwelcome boundaries she broke off and almost snarled at me, "Jesus Jack, will you stop fucking about and give me what I need. Stop being such a pussy."

I'm afraid to say that I snapped. Perhaps a reaction to the assault earlier in the day. Possibly a build up of the way Chrissy had treated me and her team over the last several months. Pushing her off and rising to my feet at the side of the bed I looked down and responded with genuine fury.

"You ungrateful, inconsiderate, cow," I began, "where the fuck do you get off? You came in here, asking me to comfort you. Which I did, willingly, because I felt sorry for what you've gone through. Though, don't forget, I went through it too."

Warming to this theme, I continued, "I was happy to respond to your caresses and was really enjoying it. But I've taken it slowly as I didn't know how far you wanted to go. In part because nowadays, even more than ever, I try to be respectful and not expectant. You're also a very senior person in the company who can make and break my career. And lastly, you've always acted like a stone cold bitch who I fear may be just as likely to bite my cock off as you are to suck it!"

As soon as I'd completed this outburst I regretted it. Enormously. Particularly the last part. Much - if not all - of what I'd said in this explosion of anger was true. But it was, I was certain, spectacularly ill advised. Calling a woman a bitch is seldom a good idea. Especially when that woman has a reputation, probably with good reason, of being a borderline sociopath.

For a few seconds there was silence. Inwardly I was cursing myself for my temper. And terrified of the reaction I'd receive. But, initially, Chrissy said nothing. She had a strange look on her face, which I was trying to determine. If I hadn't known better I'd have said that there was still a trace of arousal. Though I'd convinced myself it was anger, that I was misinterpreting as arousal.

As Chrissy continued to say nothing, I almost lost my nerve and started to blubber an apology. But, making a momentous, high risk decision, I thought better of it. I have no idea what gave me the confidence. But as I look back I'm so, so, glad I did.

Pulling her to her feet, I took her in my arms, still holding her tightly and looking deep into her eyes. I remained deeply irritated, though my out and out fury had abated. I was still unable to fathom what Chrissy was thinking. But she most certainly wasn't pulling away from me. So I became more convinced that she was not about to fly off the handle with me.

That conviction increased slightly (though I remained extremely conflicted) as Chrissy finally found her voice again.

"OK, big man, what do you propose doing to this stone cold bitch to warm me up?" she challenged with a snarl, but a heaving chest and a look and tone that sounded more and more like arousal.

"Right," I began, sounding measured and calm. Though certainly not feeling that way. "I'll give you what you need. Perhaps what you've needed for a long time. A royally good fucking. But first, get down there and suck my cock back to hardness."

I pushed her down to her knees with, I was surprised (but delighted) to see, absolutely no resistance. And none at all as she, quite eagerly, peeled down my trunks and took my cock into her mouth.

It wasn't the best blow job I'd ever had (she admitted later she was out of practice) but, quite remarkably, it was one of the more enthusiastic ones. My erection, which I'd lost in my irritation, very rapidly returned.

It was clear that none of this was against her will. In fact, absolutely far from it. So gaining further confidence from this I gave some verbal encouragement.

"Oh my God yes," I directed, "suck my cock. That is so good. But I'm not going to come yet as I want to give you the fucking that you need. Is that what you really want from me?" I inquired, giving her one last chance to either acquiesce, or pull away.

Looking up at me I got my answer. "Yes Jack, I'm sorry for my outburst. Please, please, fuck me now," she whispered. "I'm desperate to feel your hard cock inside me," She stood up and wrapped her arms around me, as she pulled me in for another kiss, even more passionate than the previous ones, rubbing her groin against my achingly hard cock.