I was in seat 1A. Don’t get too excited now, this was a Ryanair flight not a fancy business class seat on a longhaul flight but the ticket I had booked did give me a ‘premium’ seat and priority boarding. It also gave me a great view of the other passengers walking to the plane which let me play the ‘sit beside me, don’t sit beside me’ game.
It’s not a complicated game, I am not a complicated guy, it just involves me judging people based on what they look like and deciding if I want them sitting beside me on the plane or not. 99% of guys fall into the ‘don’t’ group and so do about 75% of women which sort of tells you how shallow I am.
I checked out the people as they approached the steps, a run of 8 ‘don’ts’ (I’m shallow and very fussy) before I saw her, an absolute ‘sit’. A girl in her early twenties, long blonde hair trotting up to the steps with a wheelie case and a big handbag. She was trying to shield herself from the rain but the wind was blowing and her coat was billowing behind her, doing a lousy job of keeping her dry. Her hair was caught in the wind exposing her face but that was a good thing as she really very pretty as fresh faced girls in their early twenties can be. I can’t really describe her properly, she was just pretty but there is probably a photo attached to the story to give you an idea of what she looks like.
She finally got to the steps and grabbed her bags and started clambering up but as usual, people were being stupid and seemed to think numbers on planes worked differently than anywhere else. How else do you explain why they were checking every seat row number and then doubling checking their boarding card in case row 27, where they were sitting, was suddenly going to appear between rows 5 and 6.
So there was a long wait for her to get on but each time she did move up she swung her case and bag and her boobs bounced up and down. She clearly had larger than average boobs and it didn’t seem like she had the most supportive bra on so they jiggled around nicely and caused a bit of a scene, even if it was only me who was enjoying it.
As she got closer she looked even better and that had nothing to do with the soaking she had gotten which had made her white shirt a little bit damp and clingy and see thru. Her skin looked pale and so soft, her lips plump and red and when she smiled at the flight attendant when she finally got inside the plane and showed him her boarding pass it was like a camera flash going off, illuminating the space in front of her. Damn she looked good.
He checked the boarding pass and pointed to the seat beside me. This is the point where I would internally high five myself and start working on some clever comment that would immediately get across I was funny, sensitive, smart, kind to kids and small animals and great in the sack. She stowed her bags and fell into the seat beside me and let out a big sigh. I turned my head to look at her and caught her perfume, some floral thing that was very familiar. She sensed me looking at her and turned her head, our eyes locked and I noticed how green they were. She scowled at me, “What?” she said, rather harshly.
“Is it raining?” I asked.
“Ha ha” she sarcastically laughed at me. “Yes, I should have got on at the start like you said so I didn’t get caught in that stupid queue and get soaked and have to sit here all damp.”
I raised my eyebrow at her choice of words. She sighed in reply and shook her head.
"But that would have meant having to spend even more time in your company and it’s bad enough on these trips already.”
I laughed at that. “That’s no way to talk to your boss I said, especially with the annual review due.”
“Yes boss, ever so sorry boss” she mocked, rolling her eyes and making a goofy face.
Yes, you’re smart, you got it, I knew Kellie, she worked for me and we had a very un PC and non traditional boss/employee relationship. Not in the sense you are probably thinking of (filthy minded animals that you are) but in terms of those good old fashioned things like respect for your boss and office etiquette and some would say, simple professionalism.
Now don’t get me wrong, I would jump at the chance of one of those non traditional employee/boss relationships that you were thinking of before but I was never going to pursue it, there was way too much at stake and too much to lose if and when it all went wrong. Plus I wasn’t going to kid myself that a lovely young lady like Kellie was going to get involved with an older man like me, despite how great I obviously was.
But we had a lot of fun anyway. She had been working for me for about 6 months. Her CV initially stood out due to her experience but she really stood out in the interview. Yes, part of that was the way she looked but she was smart, confident, asked good questions about the role and was just a really good fit personality wise. There are just the two of us in the team so getting on well is really important and we hit it off and ‘got’ each other immediately.
I manage a marketing related department for an online company and as we are a global company there is a lot of work and lots of people to keep happy. So there is plenty of stress and I find the best way to manage it is not to take things too seriously. So I goof around, make terrible jokes and don’t buy into the politically correct way of working we are meant to follow. Now that doesn’t mean I call the females in the office ‘toots’ and pinch their butts as they walk by but with colleagues that know me, and know I am not being serious, we talk about things that others would probably avoid.
And Kellie got this and appreciated it and was happy to follow along and in many cases lead the way. It was banter and she gave as good as she got. It made for a good work environment and we did great work.
It took us a few weeks to completely suss each other out and work out where the boundaries were, when they could be pushed and when you shouldn’t go near them. She told me early on that she was in a ‘sort of’ relationship with someone, an older guy which she said with a bit of a ‘nudge nudge wink wink’ look that made me wonder a couple of things.
We had been on a couple of business trips already and they are a great way to get to know someone better. It was all about the downtime from work and the different environment. One of the rules I have when I travel is that there is no work to be done outside of the meetings. We spend ages preparing everything and talking all day in the presentations and meetings is tiring so we relax outside of these times. I also refuse to fly in and out in the one day, I’m too old for all that jet setting straight off the 5am flight into the office bravado and bullshit. We fly in the afternoon or evening before the meetings and usually stay the night of the meetings and go home the next day nice and refreshed.
And we use the time to relax and recover and see a bit of the cities we visit. There is nothing sadder than only seeing these wonderful European cities from the inside of a taxi or hotel room or meeting room. So we go out and explore a little, eat the local food and act like tourists, even if it is only for an hour or so.
And doing a few trips with Kellie in the first couple of months let me get to know her pretty well pretty quickly. It’s not only the things you talk about or do but it’s the things you quietly notice or pick up on and every now and again it’s the big things you can’t really ignore. For example, on our first trip together Kellie set off the buzzers on the metal detector at airport security. I’d already gone through and was packing my things up again while I watched the incident unfold.
They asked Kellie to take her jacket off as they thought it was the buttons or something causing the problem. She leaned in and said something to the officer but she shrugged her shoulders at whatever Kellie had said and gestured for her to go back through and try again. Kellie did as she was asked and started to unbutton the jacket. She started at the top and I immediately realised what she must have said to the officer because as she opened the buttons it was apparent she wasn’t wearing a whole lot under the jacket.
Now I mentioned earlier that Kellie had big boobs and this was the first time I realised just how big. She took the jacket off and was left standing there in just a very skimpy and seethru camisole thing and a lovely black lacey bra. Without the fitted jacket her boobs looked huge and quite simply spectacular in the obviously very well fitted and supporting bra. It didn’t seem to bother her at all but it caused a bit of commotion among some of the other passengers with at least one husband getting a smack from his wife for staring and more than a few boys wishing they had their iphones to hand rather than in the tray ready for the x-ray machine.
As for me, I did what every good boss would do. I enjoyed the wonderful view from a safe distance and then moved on before she got through so as not to embarrass her, if that was at all possible.
There was a similar incident on a trip to Paris not long after that. The Paris office is in a high profile building in La Defense and given the unfortunate state of affairs in France, security is very tight. There are guards on the doors and they have hand-held metal detectors to check everyone going in and out. We arrived straight from the airport so had our overnight bags with us which they wanted to check. I went first and opened everything up so they could check and then moved to the side so Kellie could open her bags for them. Her wheelie case was in compartments and as I packed up my things I could see the first side had all her work things. The guard asked her to show him the other side so she unzipped it and pulled back the cover. I was packing my things up still but in my peripheral vision I saw an explosion of colour. Of course I looked up and saw three things. The first was a look that was one part boredom, one part contempt and one part ‘fuck you’ on Kellie’s face. The second was a rather sheepish and embarrassed looking security guard. The third was a case half full of brightly coloured thongs, bras and a very pink vibrator. I smiled to myself and concentrated on packing up the last of my things, again pretending not to have noticed anything that had gone on.
And now here we were on another trip, this time to Amsterdam. Now some of you are probably thinking that is fucking cool but to be honest, the Amsterdam you are thinking of is wasted on me. I don’t drink beer so I don’t care that it’s the home of Heineken or Amstel. I don’t do drugs so I don’t give a monkeys about the pot. And as much as I might look, I am never going to fuck a prostitute from one of the windows. It is a lovely city though but I find it’s a pain in the arse to get around with all the bloody canals so it is one of the less interesting cities I get to go to.
But as we sat on the plane waiting to take off we discussed the sights that Kellie should go and see as she had never been. I told her to check out the Anne Frank museum or get over to the Van Gogh museum or do one of the canal trips to see most of the city. She said they all sounded good but that she wanted to check out the red light district. I wasn't surprised by that but told her it maybe wasn’t the safest thing to do on her own so if she wasn’t embarrassed about walking around there with me then I would escort her. She wasn’t bothered so we agreed that’s what we would do.
The flight and trip to the hotel in Amsterdam was boring and uneventful but delay free so we were in the hotel by and checked in by 2:30 pm. Kellie took the city map at reception and planned her few hours of sightseeing. I went out to stretch my legs and get some lunch before heading back to the hotel to check emails and make sure nothing was urgently needed.
There were no marketing emergencies so I hopped on to the bed to relax. Well that was the plan but my mind wandered back to the events on the plane and Kellie’s wet shirt. My mind wandered again and different images of Kellie flashed in my mind. Her almost striptease in the airport on our first trip, her smile and laugh, different outfits that she looked good in, her bag of thongs and her pink vibrator. My mind wandered even further and my hand wandered down to my trousers, unbuttoning them and going inside to stroke myself as I imagined Kellie in various different sexual situations.
It wasn’t long before I had my cock out and was enjoying a very nice wank fueled by wonderfully naughty thoughts of Kellie. I was pretty close to coming when a loud ‘ping’ from my computer interrupted me. I turned my head and noticed a name that could not be ignored so after very quickly buttoning myself up I got on the video call, careful to make sure there was nothing in view that shouldn't be.
The call dragged on for 20 minutes and then I had another 30 minutes of work to do to provide the information I had sent two days earlier, in an even easier to understand format. A two year old could understand the issues now and what the necessary actions were but it would probably still be too complicated for the senior management team to grasp.
I fired off the email and was just thinking about getting back to the previous task in hand when there was a knock at the door. Completely distracted I opened the door and was met with Kellie’s fabulous smile. Somewhat flustered I ushered her in as she told me what a great afternoon she had had and explained where she had been. I nodded and smiled at the appropriate times but if I am honest my mind was wandering again and I was thinking some very inappropriate thoughts.
I snapped out of it when I noticed she was staring at me and realised she had asked me a question. “Sorry, what was that” I asked. “Food, where are we going to eat” she said “and were you even listening?”
I used the previous call as my excuse for my lack of attention and said we’d go and find something to eat in 10 minutes and I’d collect her from her room on the way out.
9 minutes later I knocked on Kellie’s door and she came out and off we went. Now we hadn’t discussed the red light district up to this point but as we were staying pretty close to it and there were some good Asian restaurants in that area which is where we were headed. I wasn’t sure how things were going to pan out but in typical Kellie style she was upfront and open.
“Let’s go look at the window girls, they start over there, look!” She sounded genuinely excited and almost dragged me over to the other side of the road so we could see better.
“Ooh look at her, she’s gorgeous” she whispered pointing to the first one “but look at the one in blue, her arse is incredible!”
It went on like this for about 20 minutes as Kellie led me around the windows. It might have felt odd at the start but that soon changed to pretty erotic as Kellie pointed out girls she liked the look of, their clothes and hair and commented on what she thought their particular skills might be. She was loving it and got more and more outrageous with her comments.
We eventually wandered into the section with the Asian restaurants and went into one I had been to before. Sitting opposite Kellie now I could see her eyes were almost shining and she looked so happy. I asked if she was alright in a jokey way and she said yes, it was just that after hearing so much about the red light district it was really cool to see. She said the girls all looked so good and it was just a lot of fun to see it and that it really excited her.
“Excited?” I asked quizzically.
“Oh come on, don’t tell me it doesn’t excite you” she said, making air quotation marks with her fingers to get the real meaning of the word across.
Being the honest and open person that I am, I told her that there was a certain thrill in knowing that sex was so readily available and clearly on show. I said it was not something I would ever follow up on though as paying for sex was a tad too far over the line for me but yes, it was an exciting thing to see and I enjoyed it.
We had an interesting conversation over the course of dinner and a couple of glasses of wine got Kellie even more animated about things. The subject didn’t stray too far from sex though and although I was conscious of it getting too inappropriate I was enjoying it, probably because it was so inappropriate. Kellie talking about sex and about being ‘excited’ by seeing the window girls was a definite turn on.
And then she hit me with something completely inappropriate out of left field.
“Since our Paris trip I thought it was safer to leave the toys at home so I’m going old school manual tonight” she giggled.
It took me a few seconds to work out what she was referring to and then my face clearly gave away my shock as she followed with this: “Oh come on, don’t think I didn’t see you peeking into my case that day, or ogling me at the airport that time!” “Or all those other times!”
I started to apologise but she stopped me with a raised hand.
“There is no need to apologise, it’s flattering” she said with a somewhat coy smile.
“Oh” was about as much as I could muster by way of a response.
“It’s not like you do it in a dirty old man kind of way” she said. “I can see it on your face, there is more respect there and not the perviness I get from others.”
I told her she was right, I did respect her as a colleague and as a young woman but that at times it was difficult to remember my responsibilities, moral and otherwise when she looked the way she did. I apologised again but she once again said there was no need. She was flattered and maybe she did a few things to get a reaction from me.
I told her it worked and it looked like she actually blushed a little but it could have been the wine or the candle light or my dodgy eyesight. Either way it quietened her up for a while as she pushed some noodles around on her plate.
“Everything OK” I asked after about 5 minutes of silent noodle pushing. She looked up and came back to the here and now from wherever her mind had taken her. She genuinely blushed this time and with a nervous grin said she was just thinking about something.
“Anything good” I enquired.
“Very she said”.
“Oh do tell” I said with a Roger Moore’esque eyebrow raise thrown in for maximum effect.
“I’m not so sure that is really a good idea” she said, but in a way that sounded like she really did want to talk about it.
It was obvious where this was going but this was dangerous territory and I needed to be careful. Or I could just go ‘fuck it’ and see what happens. We were both adults and free to make our own decisions and mistakes.
My mind raced through the possible outcomes and consequences of this conversation but while my brain was thinking of all the negative outcomes some other part of me was controlling my mouth and I heard myself telling her I didn’t realise she was shy about anything.
She looked up and I could see she was wrestling with the decision. I should have done the right thing and told her to forget about it but my thinking was clouded and I was enjoying the tension and sexual frisson. She looked up again and it was her turn to raise an eyebrow and grin. It was obvious she had decided to go for it and my heart beat a little bit quicker and my stomach did a little turn.
I was pretty sure I knew what she was going to say and I was already thinking of my reply. I looked away to break eye contact and make it a little easier for her to say it.
“You want something nice and sweet now?” was not exactly what I expected to hear but that’s the next thing I did hear as the waiter finally decided to clear the plates and try and interest us in the awful looking cakes for dessert.
We declined and as he cleared the plates, clattering them about and making awful small talk, the atmosphere between us changed and I felt the momentum of the conversation drift away. I got him to bring me the bill and I settled up and Kellie and I left, with hardly another word said between us. I wasn’t sure if this was a good thing or a bad thing and as we walked back to the hotel she seemed lost in thought.
When we got back to the hotel she seemed even more distant and after agreeing to meet for breakfast in the morning I took the stairs up to the first floor and Kellie took the lift up to her floor.
I went into my room and sat on the bed part disappointed, part relieved and part horny. My mind drifted back to the conversation and the look on Kellie’s face and I fantasised about what I could be doing now if the waiter hadn’t interrupted. My mind continued to wander to some very nice places when my laptop pinged with a Skype message. I immediately thought of the report I had done earlier and how the one syllable words I had used were still too complicated for people to understand and it was someone asking me a stupid question. As the screen came to life though the message wasn’t about work. I didn’t recognise the name, in fact it wasn’t a name it was just a string of numbers, but the message made it very clear who the sender was: ‘ready to finish the conversation?’
I immediately closed the message window on my laptop. Don’t worry, I wasn’t going to ignore this opportunity, I just didn't want any trace of it on my work laptop. I grabbed my iPad and got comfortable on the bed, it seemed a more appropriate place than sitting at the desk.
‘Sure’ I typed.
‘I was thinking about us, and I still am.’
‘What about us?’ I typed back.
‘Having some fun together’.
‘What sort of fun?’ I typed, the anticipation growing, along with my erection.
‘Probably not exactly what you are thinking of but fun nevertheless.’
‘????’ was all I could think to reply.
‘I’ve started the manual ‘work’!
It took me a couple of seconds to work out what she was referring to but then it hit me, the comment about not having a vibrator with her and going ‘old school manual’.
‘Nice’ was all I could think to reply. And the thought of Kellie playing with herself was a nice thing indeed.
‘Are you?’
‘No’ I truthfully replied but at this rate I wasn’t so sure this was going to be the case for much longer.
‘You should.’
‘Would you like that?’ I asked.
‘Yes.’
I typed ‘OK’ and then dropped the iPad and undid my jeans, kicking them off along with my socks.
My cock poked out through the gap in my boxers and I stroked it slowly waiting for the next message.
‘Are you doing it?’
‘Yes.’
‘How does it feel?’
‘Very good’.
‘Can I see?’
So this was a little unexpected, it all was to be honest, but also a little bit frightening and quite exciting. It wasn’t like I hadn’t done this sort of thing before, not with Kellie obviously, but I had used chat rooms before and was not adverse to a little cam fun. I was also too turned on at this stage to think rationally so I hit the cam button on my iPad and moved it to the side so the ‘action’ was centred.
I stroked my cock slowly waiting for some sort of reaction from Kellie but what I didn’t expect was her cam to come on as well. She was sitting back on her bed in a baby doll type nightie by the looks of thing but that is not what I was focusing on. My attention was drawn between her legs which were pulled up so the nightie had ridden up exposing her pussy and which she was slowly playing with. A single finger traced up and down gently between her lips and then up to her clit which she rubbed in a circular motion before going back to teasing her finger between her lips.
I watched transfixed and continued to stroke my own cock which grew harder as I took in the sight. The lighting wasn’t great and cameras on the iPads aren't the best so it wasn’t the best quality sight but just the thought of what was going on was incredibly erotic, as too was the line we had clearly crossed. I stroked a little quicker and concentrated a bit more on the really sensitive parts of my cock, a little precum helping to make the stroking a little smoother.
From what I could make out on the cam, I wasn’t the only one finding things were going well. Kellie continued to stroke her pussy but even in the bad light I could see she was getting a little wet as her lips spread open and her finger went a little deeper inside her. Her legs had also spread a little further apart giving an even better view and as much as anonymous body parts tended to have little interest for me, the fact this was Kellie’s pussy on view for me was very different. And as much as I tend to not really be that ‘into’ or bothered by what a pussy looks like, Kellie had a really pretty looks pussy.
As I had imagined, and I had imagined it quite often, Kellie was shaved or waxed or lasered smooth over her lips but had left a lovely little patch of dark blonde pubes which immediately caught the eye against her pale skin. Her lips also stood out against her skin, a bright pink, obviously pinker than normal given the attention they were getting.
As she continued to play with herself she started to let out little sounds, ‘ooohs’ and ‘mhmms’ as she played with her clit and then dipped a finger inside herself. I was making pretty much the same sounds as I stroked myself and as good as the view was onscreen, I couldn't help but put my head back, close my eyes and think how good it felt while knowing that it was Kellie on the other end of the screen turning me on and getting so turned on herself made it even better.
I was lost in this moment of bliss when I heard Kellie mutter something. I opened my eyes to see her swinging her legs off the bed.
“This isn't working for me” she said and the call finished.
I was stunned and sat there for a minute with my cock in my hand thinking all sorts of things. Mostly that I had fucked it up and should never have got into this, that the working relationship was ruined, she could report me to my boss, what was I going to say to her in the morning and a bunch of other negative things. All sorts of different scenarios played through my head and I felt a sick feeling in my stomach at how bad things now were.
My mood crashed along with my erection and I was tucking it back into my boxers and about to retrieve my jeans when there was a knock on the door.
‘What the fuck now’ I said to myself as I dragged up me jeans and went to answer it. I yanked open the door expecting housekeeping or some other hotel employee to be there with goodnight chocolates or something. What I wasn’t expecting was Kellie, flush faced and wearing a bathrobe and hotel slippers.
“It wasn’t working for me on the video thingy’ she said ‘so we’re doing it old school’. ‘Can I come in?’.
I wasn’t sure what to say so I just opened the door further and stepped back to let her in.
I closed the door and stood there, not quite sure what to do or how this was going to play out now. I didn’t have to wait too long to find out.
“You can’t see anything properly on Skype and an iPad and it seems a little too impersonal and I think we are mature enough to handle something a little more personal” she said.
“But there need to be some rules” she continued. “For now it is just looking and we are not touching each other.”
“Ok” I said, still not 100% sure where this was really going but knowing it was definitely going in the right direction.
“You can get back on the bed and back to what you were doing now” she directed, pointing out the clear indent on the bed where I had been lying.
I don’t consider myself sexually submissive but the way Kellie took control of the situation and told me what to do was highly arousing. Psychologists would probably have a field day with it but I guess I was a bit of an exhibitoinist at heart and here was a gorgeous young lady telling me to exhibit myself. There were probably a whole load of boss/power themes playing out but at that moment in time I just knew I was horny as hell and all I wanted to do was get back to stroking my cock.
I undid my jeans again and pushed them down looking up to see Kellie staring at the clear bulge in my boxers while she bit her lip.
There seemed little sense in keeping the boxers on so they followed my jeans onto the floor and I slipped back onto the bed.
“Fuck that looks good” Kellie muttered as I started to stroke my cock, way too aroused now to care about any possible consequences of this.
I looked up to see Kellie standing at the end of the bed, still biting her lip and still staring at my cock.
“This is so much better” she said as she slipped off the robe revealing she was naked underneath apart from a lacy white thong. “I can see everything and hear everything and you can too” she giggled as she walked around to the side of the bed and gave a little turn showing off her butt.
I took up the offer to take in the view and it was everything I expected and more. I stroked myself a little quicker and a little more firmly as I watched her move, her boobs jiggling and her hips swaying and a mischievous grin on her face. I couldn’t quite work out if she was posing for me as she moved back and forth or stalking me like prey but either worked for me.
But the stalking stopped and she plonked into the chair at the end of the bed and shifted it closer so she could put her feet on the end of the bed with her knees up to her chest.
Her fingers touched the front of her thong and she caressed her pussy through the thin material. It only took a few moments to see how aroused she was as the material soaked up her juices. It only took a few more moments for Kellie to pull the panties to the side and expose herself to me as her fingers worked more frantically at her pussy. She combined rubbing her clit with inserting a finger inside herself and it didn't take long her pussy to open out, the lips spread wide as a second finger found its way inside her and her juices began to coat her pussy.
I continued to stroke myself and had found a nice rhythm and pressure that felt great but was not going to push me over the edge any time soon. I eased back into the pillows and watched Kellie work on herself. She was more focused on herself and what she was doing than on me at this stage and she had her eyes closed as she worked away which let me watch without any awkward eye contact.
I closed my eyes and concentrated on the sensations that were building as my hand stroked up and down and around my shaft, my precum making things move more smoothly. I used my other hand to fondle my balls.
“That looks fucking good boss” Kellie breathed out huskily and my eyes snapped open to see her watching me.
Self conscious now I was being watched I stopped but she told me to start again and who was I to argue with her. As I restarted the stroking and fondling she let out a loud sigh as her finger played over her clit, a steady circular motion with a bottom to top flick every third or fourth rotation.
“I said not touching didn’t I?” she asked.
I told her she did.
“Dammit. That cock looks so good and I just know it would feel so good in here.”
I didn’t need to look to know what she was talking about but I did anyway and was rewarded with the sight of Kellie standing up to slip off her panties and turn her back on me before leaning over the chair, her gorgeous arse thrusting back at me. She opened her legs and lent a little further forward and I was greeted with the rear view of her delicious looking pussy.
I had to agree it was a shame about her rule as I was also imagining how good it would feel to slide into her, feeling her cunt gripping my cock as I pushed it all the way inside her, my hands feeling her soft warm skin, my fingers on her clit, my lips on her neck, hands on her boobs, hard nipples between my fingers.
My thoughts were interrupted as she turned back around and sat down again, this time with her legs spread and up on the arm rests.
“But rules are rules boss, you always tell me that, I’m just not sure this is going to be enough to get me off.”
My puzzled look obviously made it clear that I thought getting naked with your boss and watching each other masturbate should be more than enough to help anyone get off.
“Oh no, there is nothing wrong with this, it’s just I am a bit of a dirty bitch boss.”
I was loving her emphasis on the word boss, playing with me and our relationship, whatever that was going to be like tomorrow, but I was still confused by what she was saying and my look encouraged her to explain more.
“I’ve actually thought about this a lot over the last few months and I guess it’s having a little bit less of an impact than I imagined it would in real life now it’s happening.”
That explanation raised so many questions but given my current state of arousal I couldn’t really formulate the right questions to ask and to be honest, now wasn’t the right time to ask them anyway.
“You really are a dirty little bitch aren’t you?” I countered.
She nodded and lowered her head while looking up at me with big eyes.
“Maybe I need to to be better managed” she whispered.
And like that, the dynamic of the situation changed. Kellie was suddenly the submissive one.
“Fine then, why don’t you get back to what you were doing a moment ago and show me how well you can play with your pretty little pussy”.
“Yes boss” she purred as she stuck two fingers inside her while she played with her clit with her other hand.
I watched as she worked away on herself but sensed she needed more ‘management’.
“Open your legs wider, I want to see everything” I told her.
She did as she was told and the ‘management’ was clearly what she needed as she worked faster and her breathing got heavier as I sat back and enjoyed the incredible view.
After a few minutes of this she she asked me how I was doing and I told her I would be cumming in a few minutes. She said that was likely to make her cum but she wanted to know where I was going to cum.
I hadn’t thought about this but looking at her pussy got me thinking, if I couldn’t cum in her, I could cum on her, which is what I told her.
“I’m going to cum all over your pretty little pussy.”
She literally squealed at this and told me what a great idea it was and how that would be a lovely reward but that I would need to get closer for that.
Kellie shifted the chair against the end of the bed and slide down in so her legs were resting on the bed and she was lying pretty much flat.
As I moved down the bed closer her fingers worked faster and I encouraged her, telling her what a good job she was doing and how I hoped she was going to cum soon as I really wanted to cum myself and cover her cunt.
I was now between her legs and staring into her eyes. I could almost feel the heat coming from between her legs and it took all my willpower not to just lean forward with my hips and drive my cock into her.
I could hear her fingers working and the wetness between her legs and I could smell the sweetness of her, again my willpower put to the test as the urge to lean down and rest my head between her legs and feast on her was so strong.
But there were rules and I wasn’t going to be the one to break them.
I knew I wasn’t going to last much longer and I told Kellie. She told me to cum and that would be enough to make her cum too so I shifted a little closer and stroked faster.
I looked down at Kellie and took in the stunning view, her pretty face scrunched up as she worked herself closer to her orgasm, her beautiful boobs jiggling around as she writhed under her own touch and her pussy, just inches from the tip of my cock.
Her fingers were a blur and her breathing quickened even more and I knew she was close and it would be safe for me to cum now. I told her I was about to cum and she moaned a ‘yes please’ which was enough to send me over the edge. The first waves of my orgasm hit me and I shot rope after rope of cum over her pussy. As soon as it landed her fingers were massaging it into her clit and seconds later she was coming too, a huge orgasm hitting her and sending her body bucking. Her leg swung up and I instinctively grabbed it, holding on to it while I finished emptying my cum all over her.
Her orgasm subsided but she continued to rub her clit gently to eek out every last sensation.
I rested there between her legs, completely spent and looked at her, her post orgasm face a picture of contentment.
“Thanks boss” she purred when she opened her eyes and saw me staring at her. “That was great, but you know you’ve broken the rules.” She wiggled her leg which was still in my hand.
“What are we going to do about that?”
There were plenty more trips with Kellie over the following months and if you followed me on Tumblr you should have seen some posts which told you things were going very well with our arrangement.
We were taking every opportunity to get away from the office for quick little breaks back at the hotel to relieve ourselves from the pressure and stress of the meetings. There was still no official ‘touching’ but I think we both sensed that rule was going to break very soon. We had already broken one rule by using the office we were given on one trip for a quick bit of release. The knowledge that we were playing so close to the others and could be interrupted was a real thrill for both of us.
We were both still happy enough for me to cum all over Kellie’s lovely pussy or ass as she brought herself to orgasm, my own orgasm and the hot sticky cum that landed on her usually enough of a catalyst to tip her over the edge, her fingers and the mental stimulation she clearly got from these episodes doing the bulk of the work though.
But as with the touching rule, there was a sense that things were about to move to another level and as we boarded the flight for a two night trip to the London office Kellie was in a particularly flirty mood, even by her standards.
She wiggled her ass in my face as we climbed up the steps and made a big song and dance about stowing her bags in the overhead locker, reaching and leaning so her boobs stretched the fabric of her shirt and the buttons strained to keep them in. When she sat down in the window seat her skirt rode up revealing the tops of her hold ups. I wasn’t the only one to notice this and I got some subtle and not so subtle looks from the other passengers, mostly businessmen types who were cursing their recruitment policies but also one of the very cute air stewardesses paused to take in the view and give me what I read to be a very jealous look.
I settled into my seat beside Kellie. “What’s gotten into you?” I enquired.
“Not you!” she mock pouted in reply.
“Oh” was all I could muster in response before the stewards made their final pass and did the safety demonstration.
And talking of the safety demonstration, am I the only one that thinks it’s really rude to continue reading or chatting and ignoring the stewards when they do this? I pretty much know the routine as well as they do now but it really bugs me when people read and talk through it. I know when people ignore me when I presenting something important to them in a meeting I stop to get their attention and nothing I am talking about is going to save their or their fellow attendees lives!
Anyway, I waited till the safety demo was over to talk to Kellie again and resume our conversation although I did spend the time daydreaming about the stewardess that had been eyeing up Kellie and while she talked about emergency exits and how to put on a life jacket, I was thinking about her joining us in a threesome.
As we taxied to takeoff the engine noise increased and I knew our conversation couldn’t be overheard so we could talk freely.
“Are you OK with things?” I asked. I didn’t think I needed to explain what I was talking about and Kellie clearly knew I wasn’t talking about the upcoming meetings as she said that she was and it was fun and she enjoyed our time together but maybe things were getting a little less interesting.
I asked her in what way and she said she felt it was all a bit ‘samey’. Yes there was still a definite attraction and yes there was a thrill about disappearing off and even more of a thrill about going back into the meetings with my cum drying on her pussy or ass but that kink was old and she felt she needed something more now.
She went on to explain that a huge part of these episodes was the mental part. The taboo of messing with her boss, an older man, someone supposedly in authority, the risk of sitting in a meeting with cum drying on her, could people smell it or smell her own musky sexness. She said she loved seeing my reaction each time she stripped off, revealing her latest panties and my reaction if she slipped them off and I got to see what she had done with her pussy. Sometimes she was smooth, sometimes she had a landing strip or tuft and last time she had let her bush grow out which I loved.
Allow me another sidetrack moment. I love a good bush. I grew up at a time when everyone had a bush, at least they did in the porn mags I used to buy from the local newsagents - imagine having to go into a shop and buy porn from real people! Fuck that was dedication and something I think kids today lack given how easy it is to turn on a pc or phone or tablet and have every kind of porn at your disposal in seconds for free.
Anyway, I grew up with bush in porn and it set the standards for me I guess and what I am used to. Now don’t get me wrong there is nothing wrong with a smooth pussy but I just prefer one with a little bit of hair.
Anyway, Kellie had a little bush on our last trip away and it looked great, especially with my cum splattered all over it, the white of it a wonderful contrast to her dark blonde hair.
She confessed the time we did it in the office on the previous trip was a favourite.
