Meet the Big Boss

You image the CEO in your head. You've never talked to him only seen him from far away. And of course you never thought about him like – this. As a man. But he’s a hottie, in a daddy kind of way. In his late 50s, still with a full head of hair that is rapidly, turning white though. Tall and lean, his expensive suits show a body well looked after for a man his age and his aura is that of an energetic self made man who can have everything he wants. You gulp an feel yourself getting wet between your legs thinking about him for the first time as a woman. No way to deny it, you’re one of the things he can have if he wants – he’s total daddy, absolutely your taste. You blush a little about how certain you already are about your “taste in men” after two days as a woman. You click the reply button.

“I appreciate the invitation very much and am happy to start my round today in the CEO’s office.

Thanks and best regards

Lexi Jordan"

You click send and turn back to the intern waiting.

You notice a bulge in his jeans – apparently he’s been using the time you sent the mail to eye your pushed out butt. You hadn't even noticed you presented it out. Comes pretty natural, by now.

“Oh, you're’ still here. Don’t worry, young man, your boss won’t kill you because the letter goes out a little later, it’s not that important.”

He nods a little sheepishly. He’s cute. And you do feel flattered by the attention of a young boy having a crush on you, but you’re priorities are very different at this time. Maybe you'll pay him a visit one day later for a quickie, but not today.

You lean over and kiss him on the cheek, letting one hand wander down his back and pat his firm young ass in his tight jeans. You smile as you see his eyes widen and his cheeks flush bright red. At least he’s got something to dream and talk about now.

“Sorry, I’d love to talk you young man - I'm quite keen get the chance to get to know you better soon, but now I have work to do!”

He nods.

“Of course, Ma’- Lexi.”

“Wait a minute, we can keep me company in the lift.”

He smiles happily, and a minute later you, your trolley and the intern enter the lift. He’s incredibly awkward, alone with you in such a small space, even if it’s just for the few seconds until you arrive at his floor.

“Have a nice day, young man!”

“Uhm, yeah, you, too, Lexi.”

As he leaves the lift, you give him another slap on the ass for good measure and hear him suck in air sharply. You chuckle. You enjoy being at the service of your workmates and let them use you, but teasing this teenager a little and letting him know he’s the bottom of the corporate ladder even below your entry level job is a nice change of pace, for once. The doors close and the lift moves quietly and swiftly to the top floor of the high building.

You straighten your hair, check your clothes making sure they're as tight in all the right places as they should and enter the CEO’s anteroom. His PA who you met yesterday smiles at you professionally.

“Ms. Jordan. How nice that you could make it this early. He'll be very pleased.”

Her eyes wander over your body approvingly leaving no doubt as to why he will be.

“Here's the out-mail, put the mail into the inbox, I’ll let him know you’re here.”

You nod and do your job quickly and professionally. When you look at her she smiles and nods.

“He’s ready to see you now. Just leave your trolley here,”

You nod, breathe in and enter the Big Boss’ office through his leather padded door. It makes a quiet sighing noise as it opens and falls back with a soft thud automatically

He’s sitting at his huge wooden desk, looking even more handsome than he does in the pictures you saw of him or from afar. His hair’s almost completely white, his photos on the website need a bit of an update – his face has some more lines that the smoothed PR pictures – they suit him. Make him look distinguished. Experienced. Weathered by life.

He looks up from his papers at you over his rimless glasses – you never saw him wearing those – and are a little sad when he takes them off. They look good on him.

“Ah. Lexi. I may call you Lexi?”

You blush slightly. You feel a little tingly just because he talks to you at all, so he could probably call you anything and your new body would like it.

“Of course, Sir.”

“Splendid.”

He seems pleased. And looks at you wordless for what seems like an eternity to you. It’s probably not more than five seconds, but in these circumstances, it makes you feel like he’s looking at a new car for his collection before he buys it.

“Glad you decided to come. My Assistant made it clear that it wasn’t an order, but an informal invitation you could have refused at any time!”

“Yes, Sir.”

He smiles.

“Splendid.”

He’s looking at you some more – you may interpret too much into this, but his expression seems a bit more – like a man who just bought that car he had his eye on.

At long last he nods towards the chair in front of his desk.

“Do sit down, let’s have a talk. I’m curious about you, Lexi.”

You sit down and almost sink into the chair’s soft padding.

“I’ve heard some very good things about you yesterday. You’ve made quite an impression on your first day. Raised some eyebrows. Seriously improved the working atmosphere in my company.”

You smile.

“I was hoping I could, Sir.”

“And when I inquired a bit about the new girl, I found you aren't actually new at all? Your old boss told me you've been working for us quite a while in quite a different position?”

“Right, Sir.”

“Can’t say I ever heard of you down there. Which was a waste. Such a pretty and charming girl working for me boxed up in a cubicle where I couldn't notice her… Why did you change – career paths, if you will?”

“Well...”

You clear your throat.

“Probably mostly for that exact reason, sir.”

He lifts an eyebrow.

"To get my attention?”

You giggle and feel the blood rush so your face.

“Uh… No... I mean… sure. I am very glad that you did notice me, Sir. VERY glad!”

He smiles.

“But what I mean is that I kinda felt stuck in that cubicle, no way forward, no social contacts, no real purpose. On my first day yesterday, I meat so many nice people I never knew worked here. I’ve made many people smile and improved their day. And yes, in return, many more people know me now, greet me, are happy to see me. I feel this job has so much more purpose and meaning.”

He nods, apparently very satisfied with what he heard.

“I did hear from your colleagues that you’re… open to the social aspects of your position. Taking compliments, smiling, hugging, physical contacts. You know we've had some – ruckus with your predecessors about that.”

You nod.

“I enjoy that part a lot Sir. Most of all, really. I have some – bruises from all the slaps and pinches I got yesterday, but I wear them as marks of honour.”

He laughs out loud and you giggle.

“That's a very refreshing attitude, young lady. Really glad you took the step out of your cubicle that attitude would be so very wasted.”

You nod and take the compliment with a grateful smile.

“And you know it’s not likely to remain at being fondled and hugged, right!”

You blush again, feel even hotter in the face this time.

“Y...yes, Sir, I'm ready to serve the company in any way that I can with my whole body and mind.”

“Splendid!”

He eyes again wander over your body and this time he looks like he’s ready to test drive his new car.

“You wouldn't mind showing me all you have to offer to my company, would you, Lexi?”

You gulp.

“Of course not, Sir. Whatever you wish, sir.”

And you mean it. You've been talking to this man for less than five minutes, but you can’t imagine denying him anything he asks for. His aura of power, strength, natural authority doesn't give a you any wiggle room. And of course you always enjoy showing off your new female body, even more so to handsome Daddy like this one. The little male voice somewhere deep down in your brain trying to hold you back now that you’re a strong, independent woman by accusing you of how fast you’ve fallen into the pattern of a slut for older men is silenced by the tingling in your pussy as you stand up.

His eyes gleam lecherously as you strip off your outer layer and stand before him in your underwear.

“All of it please. And make it nice and slow!”

You smile and continue the show, slipping out of your panties, letting him open your bra for you and then presenting yourself to him as the curse made you. Your pride of your new body is again justified as you can practically see him drool over it. You have no doubt a man in his position and with his power has a lot of women to compare you to, but he’s obviously entranced by the sight.

“Splendid. What an amazing jewel has been hiding in that cubicle for such a long time. What a waste!”

He’s enjoying the view for quite a wile – you’re surprised how it doesn't feel awkward at all, to stand here naked in front of this older, powerful man and be assessed like a mare at a horse show. You enjoy it. A lot.

“Turn around and bend over, please!”

You do as ordered and think you feel his gaze burn even hotter on your skin. He definitely makes you stay like this for a lot longer. Makes you spread your cheeks, show him your brown hole. You create a mental file – “ass man”.

Finally he lifts a hand and waves you to him.

“A girl with your – qualities and your attitude can go a long way in this company, Lexi.”

He puts a hand on your ass.

“Especially now that you have the attention of the man in the top floor office. I enjoy being the – patron of pretty young ladies.”

You smile down on him

“Yes, Sir. I’d appreciate that a lot!”

“Why don’t you show me how much? Impress me to show me you deserve my special facilitation.”

You nod – take out the mental folder you just created and bend over his desk, spreading your cheeks. You turn your head, see his eyes wide, and his grin become undeniably predatory.

“I like the way you think Lexi.”

He leans forward in his chair, kisses your ass-cheeks, licks them and then spreads them to explore with his tongue your tine rear entrance. You gasp. Seems you have to expand his file a little. He's REALLY an ass man.

This feels wholly new to you. You decidedly stayed away from all kinds of ass play, as guy – totally gay, right? - and didn’t have the chance to explore it now that you’re a woman. Without the looming, terrible, terrible idea of it making you gay, you can relax and enjoy the sensation - and you do. It’s really nice. REALLY nice, to feel his probing tongue back there. Completely different, obviously, from any attention you got for your pussy and clit. You're not going to cum from him licking you there, but it’s a deeply satisfying emotion nonetheless. Highly sexual in a different way. And also – even more intimate and personal than getting your pussy licked. It seems – appropriate to share this with this older, distinguished man. He deserves do explore you in a way no man has ever done before. No one has, no matter what body you were in. You close your eyes and moan. He takes his sweet time, obviously enjoying every second of it, maybe more than you do. And you could get this done all day. But then, licking his lips, he comes up to you and kisses you. You don't hesitate a second, taste a slight tangy aroma on his lips and tongue that is yourself when you passionately return his open mouthed kiss, while you feel his fingers massaging your puckering hole.

“Say, little Lexi - have you ever offered your asshole to a man?”

You gulp. It's the obvious next step, yo it doesn't come as a big surprise, but you successfully ignored the implication of your CEO master’s fetish.

“N… no, Sir… Never.”

He smiles warmly.

“I was hoping you’d say that. I was not mistaken in assuming that deflowering that tight little ass was part of your offer when you presented me with your sweet behind?”

You take a deep breath. As man that was out of the question and as a woman you haven’t spend time thinking about if this is part of your new life. But your body has made its choice. Your pussy is tingling like crazy to the question, and your whole body feels warm and hungry.

You nod.

“Yes, Sir. My ass is yours. Use it as you please!”

He kisses your forehead.

“Such a good girl!”

He takes a tube out of his top drawer – doesn't keep it far out of reach, you notice, and squirts a glob of transparent lube on his hand. Picks it up with his finger and massages it into your asshole. You gaps sharply - it’s cold. You start to moan then. It very soon gets warm as he rubs it in. Then he opens his pants and takes out his cock. Your turn your head, your new you is insatiably curious to see manhoods and compare them.

Protruding from a nest of silver grey hair, bend slightly to the left, circumcised, a single blue vein pulsating. It’s bigger than yours was – you can’t help but notice you make that mental note about every single cock you encountered as a woman. Your male self image of being more or less average has been repeatedly shattered lately. It’s not huge – this one probably IS average in length, about 16 or 17 centimetres, but it’s quite thick. Really quite thick. Must have twice the girth yours used to have. Cocks that thick you saw in porn movie, were usually longer, which gives the CEO’s an air of – rootedness? Solidity? It looks a bot like a tree trunk, reliable, solid, unchangeable.

You gulp as your remember where it’s going to go. Of course the first cock in your ass is staff the girth of your wrist....

Her uses the rest of the lube in his palm and rubs it on his thick shaft, while still massaging your butt hole, opening it gently, probing one finger, then two then three into it, making you gasp and sigh.

“Not going to lie to you, if you’ve never done this before it’s probably going to be a little unpleasant at first. Especially as my cock is quite…”

He chuckles and you nod.

“I noticed, Sir. Don't worry, I’m a big girl, I can take it!”

He nods and puts the fat head of his cock against your tiny sphincter. You close your eyes, breath in, try to relax your whole body as much as you can as he drives it though the resistance of your sphincter and makes you moan a low, pressed noise, you breath out then the head enters you fully. Your hole feels stretched to its limit, this is one thick fucking prick. You sigh heavily.

“All right?”

He strokes your hair and waits for your response. You nod.

“Yes Sir. Go on!”

”Good girl.”

Shoves his cock deeper and deeper into you. You feel your muscles gripping him tightly, resisting the intruder, but it’s not as bad now that his whole girth is inside you and you're stretched around his shaft, the pain that came with this intrusion quickly becomes a dull throb. It's still unpleasant when he enters your bowels as deep as he can and you feel his pubes against your skin, but you feel you can adapt. Your sphincter is already getting used to the stress of the stretching – it still resists as he pulls out again and re-enters you faster and harder, but it’s not as bad as his first entry. And as he gets faster and harder with every new entry into your dirty little hole, your dull throbbing becomes less unpleasant – pleasant even at a point when at that point your moans change melody, form the grunting of bearing an intrusion to the moans and sighs and screams of welcoming a beloved cock in your tight hole, enjoying its presence.

Every new thrust of his thick cock send a shiver through you now, and your pussy is enjoying it, enjoying the sensation so close to it, getting wet and tingly, sending a warmth all through your body making this at long last a completely pleasant and wanted experience.

You close your eyes and focus in the feeling of fullness in your bowels, his grunts and moans of pleasure, the slapping noise of skin on skin every time he's at his deepest point of entry. You feel his sweat drop onto your back, his wet lips when he bends down and kisses the back of your neck. You grab the edge of his desk and hold on to it, as your body starts shaking and trembling with delight. Something is set free inside of you, like a continental shift, this isn't the sharp immediate bliss of having your clit pleasured or even the grounded pleasure of a vaginal orgasm. You feel you’re not going to cum like this, at least not now, but you don't care. It just feels amazing, full, united with a man in an even more intimate way than vaginal sex could ever offer. You're glad he’s your first in this hole, he's not just experienced enough to make in undeniably a prefect experience, he’s also obviously so very much enjoying it. You've never felt a man this happy – or a woman – or yourself when you were a man – as he is, pumping away into your tight little asshole. He’s a man who found his call, his purpose in doing this, and being that for him is a lot, more satisfying and blissful than the short peak of an orgasm.

You close your eyes and enjoy the CEO enjoying you, enjoy how much of a purpose this gives you, how needed and appreciated you are right now. You lose track of time, because you can just fall in to this - the fullness of body and the meaningfulness of your being.

Eventually he gets more frantic and you feel his thick cock inside you twitch. You let out a happy, satisfied sigh as the almost 60 year old man deposits his hot, creamy load into your bowels. Rams it into you once or twice more until he turns soft and slips out.

What's next is not a conscious thought or plan, your body just takes control. You slide of his desk and get down on your knees, take his limp cock into your mouth and start sucking it, savouring the tangy taste that doesn't turn you off at all, quite the contrary.

Eventually you look up to him and smile, his cock still in your hand.

"Thank you so very much for being the first in my asshole, Sir. I couldn't have wished for a better lover to deflower it.”

He smiles happily, broadly. For a man with his tastes that must the ultimate accolade. And you didn't even lie. You are grateful to have gotten this behind you in such a pleasant way with such an experienced lover. You stand up and get dressed again.

“Tell me, Lexi, what made you offer me your ass? Most girls trying to impress me are quite unimaginative. Showing me their their tits – especially when they have nice tits like you - or a offer a Blowjob. Dis you talk to anyone about my likings?”

“No, Sir. I just though a man of your – experiences and worldliness must have more refined tastes than the average guys I usually meet. And preferences. And in my mind, a man who appreciates a lady’s ass and knows how to treat it right is the highest form of a gentleman!”

You wink at him. Honestly, you just noticed him staring at your ass, and having been a man with a certain likings for female behinds yourself, you notice an ass man when you see one. But the compliment comes easy of your lips, because it’s half true. All the thing you said about him are right: you do consider him a man of taste, class and refinement. It’s just that that's not because of his fetish but his demeanour. But his grin becomes wide and he beams at you. You obviously, said a very right thing to flatter his ego - you're not surprised he's at the same time sensitive about and quite proud of his likings of the female behind.

“You're quite a rare specimen, Lexi. You seem to have a knowledge about men far beyond your years or actual experiences.”

You chuckle and take a risk

“Used to be one, myself, Sir!”

He frown – and laughs as you shrug and chuckle.

“Aha. Good one, Lexi. Not that I'd mind you being a trans woman, but I’ve made some extensive research about you. I’d know. You couldn't be more of a woman and were all your life.”

Apparently, you are, you think. He pulls you towards him and kisses you.

“I really enjoyed this little getting to know meeting. I’d like to expand that. You're way too interesting to just use you as an office relaxation toy once in a while. What you thou think about taking lunch with me tomorrow?”

You’re startled.

“In the canteen?”

He laughs.

“I don’t really go to lunch there. Even if I did, I’d want some place a little more – intimate than that. Office talk is going to find out about the two of us soon enough as it is.”

'Us.' There's an 'us' with you and the CEO, now. He seems to have big plans for you.

“I’ll have my Assistant reserve us a table at my favourite place. They're booked in the evening for weeks, but they'll probably be able to get us a table for lunch.”

He casually mentions the name of the best restaurant in town and your eyes widen. You probably couldn't afford a salad there. But you’re a woman now, invited by your boss, no worries about paying.

“I - that’s… probably going tot take longer than my lunch break…”

He chuckles.

“I know your boss' boss, I think I can put in a good word for you if you extend it a little.”

You blush. Of course his needs become your major duty, already.

“I… I’d love that, Sir. Sounds great.”

“Superb. No need to come up here, then I'll pick you up at noon tomorrow”

You nod gratefully and leave his office, flabbergasted as to what just happened.