The Boss

I walked back into my office, and my boss, Diana, was standing waiting on me, Diana and I get on great, well usually, and while she was technically my boss, we have a very relaxed manner with each other, and very little she ever said to me was taken seriously, it was just the relationship we had with each other, I had been at the job long enough to know what to do and how to do it, and she generally left me to it, anything she needed to be done, she knew I would get done for her, and the very odd occasion she needed to be serious... well I knew when she was being serious.

Her being in my office waiting on me didn't shock me at all, I just figured she was either in for one of her general chitchats, which probably took up a good quarter of my day, or was in to ask me to pick something up for her, which chances are I had already on my radar, or else was already done.

"Where the hell were you, I needed you like five minutes ago, the formulas are messed up and I need them sorted now."

"Gee, sorry Di, I was taking a break why don't you just chain me to the chair sure," I say as I sit down and start to pull up the sheet she's talking about, to see what is wrong with the formula.

"Oh don't you go giving me ideas mister, you wouldn't want to know what I'd do if you were all chained up to that chair," she quipped back, just the normal banter that we seem to be having more and more frequently recently.

I laugh out loud, "that sounds like a real fun challenge there Di, you just make me work late some night and you never know your luck I might just let you chain me to the chair and do whatever you please, the formula is fixed, somebody changed a couple of cells about, no idea who or why they would, but hey easy fix."

"Thanks, Z," Diana starts to walk out of my office, "Oh, and be a dear, and get me a cup of tea please."

I can't help but laugh at this and start to get up, "Sure, what did your last slave die of."

Diana gives me a sultry smile, licking her lips lightly, "Oh far too much pleasure, and I'll leave what kind of pleasure up to that wonderfully wicked mind of yours," and walks back to her office.

I shake my head and laugh to myself, as I go and make her a cup of tea, I really didn't quite know what to make of the interactions with her recently, I mean I have always found her to be attractive, I mean who wouldn't 5ft 4 shoulder length brown hair that she constantly wore down, piercing green eyes, and while she never dressed provocatively, she seemed to have a wonderful figure, that I would be lying if I ever said I hadn't imagined what she would like naked.

I would of never in a million years think that she would have been interested in me, I mean...I'm a good 15 years older than her, somewhat overweight but not in an obvious way, but recently the flirting and teasing have become more intense, and a lot more frequent, and she has been finding more and more excuses to be in my office.

I sigh to myself and take the tea and lightly knock on her door, before opening the door, "tea's ready mistress," I say smiling at her setting it on her table, "I'll be my office if you need anything doing to you....er sorry for you" I say shooting her a mischievous wink with the deliberate slip. I do like teasing her and flirting with her and feel like until she says something no harm no foul and walks out laughing to myself.

The next day when I come into the office I have to take a 2nd look, ok being honest a 3rd or 4th look at Diana, cause a 2nd look at her is a fairly common occurrence, normally she dresses very conservatively, jumpers, high neck tops, and always in jeans or trousers. Today for whatever reason, she was in a blouse, while still buttoned up to where she was not showing anything, it was a marked change to how she normally dressed, but the biggest change was she was in a skirt, plaid just above knee length, with stockings on, and for a real change she was wearing makeup. Something that in the 3 years we had worked together I could probably count on one hand the number of times I had seen her wearing any, and I could never remember her wearing a skirt, I have to say, she looked amazing.

"My, my, my your looking well today Di, got any nice plans after work," I say smiling walking past her.

She looks over at me and smiles an impish smile "Well it all depends, you never know what might come up between now and then."

Work seems to go a lot slower today partly cause Diana is constantly finding excuses to come into my office with different bits and pieces of work for me to do, and well after she leaves it is a good five or ten minutes before I can get my head out of the gutter to focus back on work, the intensity and the frequency of the flirting is at an all-time high, and well its getting harder and harder to stop fantasies flying through my head.

Just as I am finally getting finished the night, with plans to go home and ashamedly take care of myself, Diana walks into my office and leans over the desk, I can see immediately that she has opened a couple of buttons on the blouse to where I can see some cleavage, and I immediately feel myself getting hard, I don't know why but well I've fantasized about this kind of thing happening often enough I suppose it was an ingrained reaction.

"Hi Zack," she says smiling, "Would you mind being a real dear and working late tonight, I have something that I would love your help taking care of."

"Sure Di, you know me, eager to please in any way I can," I say, thinking to myself that it will just give me more images for my bank later that night.

"Oh good," she says and hands me a credit card "head out to Jimmy's and get me the Number 2 special and get yourself something to eat as well," she says as she turns around and starts to walk out, stopping at the door to turn around to add, "and get us a couple of drinks as well it could be a long hard night."

I hoped that she hadn't caught me unashamedly looking at her ass as she walked away, something I always did, but in that skirt, it for some reason was even more eye-catching

I wasn't 100% sure what her plans were, while working late wasn't normal, it wasn't abnormal...but being sent out for food, that was totally new, normally when working late it was a case of sort yourself out if it was after a few hours, plus generally any time work needed done late she was first out the door.

When I got back, she called out to me, "I'm in your office, bring the food in with you," I didn't think anything of this, Jimmy's was a burger joint, finger food if there was ever finger food. I went for the number 2 special as well. To be honest it was my usual from Jimmy's anyway so was a pleasant surprise when it was what she wanted as well.

I walked in and took me a second or two to realize she had music playing, and it happened to be one of my favorite songs just finishing, I was wondering if she had put on one of my playlists, but while I recognized the next song starting, I knew for a fact it wasn't one of my playlists.

I then realized that she was sitting on my deck, my monitors had been wheeled away from the deck, and the laptop and keyboard had been set away leaving my desk clear. I naively thought that she had cleared the desk till we eat, and would reset it for work once we were done.

I walked around setting the food beside her and went to sit down when I noticed that handcuffs had been attached to the legs of my chair, I wasn't sure where tonight was going to head or what her plans were, but I was very excited to find out. I stood at the chair before sitting down and said, "So are you going to finally show me what you would do if I was actually chained to my chair, or are they there just to tease me even more Di."

Diana slipped off the deck smiling sweetly, "well why don't you go ahead and chain yourself up and we will see what happens," she said, moving the food back and leaning almost bending over the deck, to start taking the food out of the bag. She looked behind her to see me looking at her ass she smiled, "come on, chop chop, sit down and get them legs cuffed up mister," she said turning back around to finish sorting out the food, "be a good boy and there will be plenty of time to ogle me later"

I can only gulp at this, I have wanted this so often and have dreamt about this so much I almost have to pinch myself to ensure that I not dreaming, I sit down and reach down to close the cuffs around my legs, leaving me attached to the chair that it would be near impossible for me to walk off anywhere, I could still stand...but that would be about the height of it. I wondered what her plans were for my arms as there were no cuffs about for them, so I ask, "I getting to keep use of my arms or do you other plans to keep them occupied mistress Di?"

"Well now Z, you will need your hands to eat, and to get any kind of work done won't you." She replies

We eat the burgers quickly, she sits on my desk during this time with her feet lightly resting on my thighs, the skirt riding up slightly, not enough to let me see her panties, but enough to show a lot of her thighs, and again I feel myself getting hard.

When we are finished, she clears up all the rubbish into the bag and takes it out to the bin, while I sit chained to my chair wondering and eager to find out what is about to happen

She walked in and closed the door standing up against it. "So since you seem to be so eager to please, I was wondering," she said undoing another button on her blouse to where I could now see her red bra, "if you would be eager to pleasure me."

I smiled, "Umm Di I would be honored to but, are you sure it's something that you want?" I asked kicking myself as I said it, I didn't want her to think I wasn't interested, but at the same time, I wanted to be sure this was something that she wanted even though at this precise moment in time I probably couldn't stop her doing anything she wanted even if I wanted to.

I can see her smile back at me, "Always so caring, even when it comes to something like this, it's part of the reason I like you, Zack, of course, I'm sure, as long as you are."

I continue my grin, and say, "Well mistress I suppose I am yours to command, what do you want me to do."

"Just sit back and enjoy the show for now," she says

I lean back in my chair and watch as she changes the music track to a slower, song and starts to move her hips in time with the music, she runs her hands down her face and neck, running the fingers down to the buttons on her blouse, and slowly starts to pop them open one at a time, while moving closer and closer to me.

When she finishes opening the last button on the blouse she is standing in front of me. I can't help myself but I start to move closer to her, She smiles down at me and as she lets the blouse slip off her, she runs her fingers down my face and bops me on the nose, "Patience boy, your just to sit and watch for now. Time for touching later."

She smiles and takes a step back, snaking her hands down to her skirt, grabbing it at the bottom, and slowly working it down, bending down with it, when it was pooled around her feet, I can see her take a step out of it, and then I feel my heart jump into my throat as she rests her hands on my upper thigh, resting on my already hard cock, giving it a little squeeze as presses herself up standing in front of me again.

She looks stunning standing in a red bra that shows plenty of cleavage of her breasts, and a pair of red frilly panties. She sits on my lap, tossing her hair behind her shoulders leaning in, bringing her cleavage right in front of me, as she places her hands on mine, lifting them and taking them behind her back. I didn't need a 2nd invite and helped her unclasp her bra. She leans in close allowing the bra to fall forward her breasts pressing up against my chest, as she whispers into my ear,

"Hope you're enjoying the show," she says as she gives my cheek a little peck.

She stands up and turns around as she starts to bend over removing her panties, giving a glimpse of her pussy when they are around the floor she kicks them off, turning around to stand naked in front of me, apart from her thigh-high stocking. She runs her hands down her body and smiles,

"well mister, I hope I don't disappoint you"

It takes me a few moments to pick my jaw up from the floor, I always thought that she looked wonderful, and would be lying if I said had never pictured her naked, but even in my wildest imagination couldn't do her justice.

"Di, Diane, you definitely don't disappoint," I say smiling at her.

She blushes at this, which only serves to make her even more beautiful.

She takes my hands and helps me to my feet, while I look at her, wondering what she is wanting me to do now, she unbuckles my belt, and opens up my jeans, pulling them down, as she kneels in front of me. She slowly almost teasingly starts to lower my boxers, I can feel my cock strain against the waistband, waiting to pop out.

She starts to kiss along the shaft as she lowers the boxers lower and lower until my cock springs free.

She lets my boxers drop down and gently but firmly pushes me back into my seat,

She starts down at my balls, she rains gentle, little kisses up the length of my cock, working her way up before taking my head into her mouth and gently sucking, it takes all my willpower, and self-control not to cum immediately, she starts working her way up and down, bringing her hand up to wrap it around my cock as well, using her mouth to push it down, before using the hand to move her mouth back up, she starts to swirl her tongue around my head when her lips are up around it. She gives a couple of quick bobs up and down before lifting her head.

"Ok, your turn," she says, as she sits back on the desk, lifting her lefts to rest them on my shoulders, using her heels to pull my chair in closer to her, I lower my head down, taking it slow, starting to kiss my way up her thigh and working my way slowly towards her pussy, I kiss my way around it, teasing her, bringing my mouth close to lips, before moving away again. She starts squirming beneath me, trying to anticipate when I would be close to try and get me to kiss her pussy. I eventually let my tongue slide up the length of her slit, swirling it around her clit, before working it back down and into her pussy.

I can hear her let a moan of pleasure escape her, while I start to work my tongue in and out, sliding it up and around her clit again. I feel run her hands through my hair, pulling me forcibly up while she starts to grind herself against me. I feel her get a lot tighter and wetter as she moans deeply, her body quivering beneath me.

She gently but forcibly pulls me away, breathlessly she says, "Enough foreplay, I want to ride your cock now."

She brings her legs down, and I have to say that I kind of sorry she did, I don't know what it is, but I find something very special about eating pussy, and she had a wonderful pussy to eat. She stands up and steps to either side of me and slowly lowers herself down, she grabs my cock and, slowly starts to slide herself down my cock, working herself deep inside. She slowly, and gently at first starts to rock and bob herself up and down, quickly getting herself into a rhythm, her breasts bobbing in front of my face with her movements, I reach behind her pulling her closer to me as I take a nipple into my mouth and sucking and flicking it with my tongue, using my fingers to tease the other one, before switching over, I start to thrust up against her as she is lowering herself down, working with her. I feel her tightening around me again, as she moans I move up kissing her neck, before deeply Kissing her.

I break off the kiss and kiss my way to nibble on her ear before whispering into her ear, "Di, I'm close to cumming"

I feel her quickly stand up and before I know it she is kneeling in front of me again, her lips wrap tightly back around my cock head, her tongue flicking all over the head, and her hands starting to fondle my balls and gently stroke my cock as I shoot my load into her mouth.

After I was finished, she sat back, licked her lips clean, and smiled up at me. She reached up to the table and lifted the key and unlocked my ankles,

"Well, I think that's enough work for tonight, shall we start to make this a regular overtime meeting."

I can't help but smile at her, "It shall be my pleasure, but how about next time we tie you up."

"oh now that could be fun," she said