How I became my secretary's sissy secretary.

My wife said to prepare for my new position, that I will have to spend as much time 'en femme' as possible.
That meant that all day I would be wearing high heels, as well as my lingerie, as she quite rightly said, the last thing I would want to happen is stumble, fall and reveal my secret.
Also I had to practice my female voice and she told me to record myself reading out loud from her 'Cosmopolitan' magazine.
Let me tell you some of the articles in there were as raunchy as any men's mags, there were articles like 'Good vibrations: which is the best vibrator for you?' and 'Oral sex, spit or swallow?'
There were many times when I would be reading them, looking in my reflection in the mirror, enjoying the sight if my hard cock tenting out my panties and my black peignoir adding to the excitement of obviously a man in sexy lingerie.
I would stroke my cock, keeping me on the edge of cumming, but resisting the temptation to cum, as I know when my wife came home the pleasure would be even greater.
If she thought I did not get the voice quite right, I would have to read it again, but at the same time she would either be playing with my cock, or sucking it. She called it 'stress testing', I have never enjoyed being stressed more.
One time I was reading an article about sexual fantasies, while standing in front of my wife and she was sitting in a chair.
Her skirt was pulled up, showing her stocking tops and had no panties on. Her fingers were furiously delving deep into her wet pussy, making sexy liquid sounds as she played with herself.
I had to keep reading while she was coming, my black see-through panties were struggling to keep my cock contained in them, and my pre-cum was soaking them.
When she had finished coming, she looked me in the eye, slowly removing her fingers from her pussy, which gave a last liquid pop as they finally came out.
Then put her fingers in her mouth and started sucking her pussy juices from them.
The expression on her face was as though she was tasting the sweetest honey.
I must admit that I came then, without touching myself.
The jets of cum, easy to see in my panties, filling them with creamy cum.
When I finished cumming, my wife ordered me to take my panties off, kneel between her spread legs, and lick my cum off from my panties.
She started playing with herself again, and having my face so close to her pussy, the scent of it and the sound seemed magnified.
When she came again, she took her fingers out of her pussy, and this time gave them to me to lick clean.
Her lessons must have been working as on Friday the phone rang, and I answered it without thinking, and I immediately recognised the voice of my boss, Mike.
He did not recognise me, and assumed that it was my wife answering as he said "hi Jane, is Steve there?"
I said "Hold on I will get him," then put the phone down on the table and walked away, knowing he would be able to hear the sound of my high heels on the floor.
Then I took my shoes off and went back to the phone, and as I picked it up I had a moment of panic, trying to think of how my voice normally sounded.
The call was just about how to return to work when I felt ready, but the fact he was totally taken in on the phone gave me confidence that it did sound feminine.
When it came round to Monday, and my 'first' day of work the nerves kicked in and while I had my shower I was thinking that I could not go through with it, and thought I would tell my wife.
When I went into the bedroom I saw the outfit that my wife had laid out for me, and the thought of not going through with it vanished from my mind.
The lingerie was a matching set of pink satin bra, suspender belt and panties.
There was a short pleated tartan skirt, with a white blouse which had ruffles down the front.
I recognised the skirt and blouse as what we bought when we went shopping last week. She had said that she was buying clothes for work, I never suspected it was clothes for ME to wear to work.
"Before you get dressed we had better make sure THAT doesn't make an appearance " she said as she looked at my cock, which was already beginning to swell as I looked at all the feminine clothes on display.
She had already prepared herself as she had a bowl of iced water and a flannel, which she used on my cock to make it shrivel to a manageable size.
Then she opened a drawer and took out a cock cage, which I had never seen before and I wondered if that is what she was buying last week when she left me alone in the shop last week.
She quickly attached it around my cock and balls, and I heard it click shut.
"Don't worry I have a key for it" she said as she showed me a small key that was on a silver chain, which she put over her head, and the key nestled between her boobs.
She showed me a small jewellery box, and inside it was an identical key and chain "make sure you give this to Linda, in case she wants to make use of you.
My cock, quickly filled the cage, but couldn't get fully erect, and there was only a small bulge, which when I had my panties on would not be hugely noticeable.
"Now we want to make sure your tits stay in place," she had put adhesive pads on my silicone boobs, then placed one boob on my chest, held it there for a few seconds, then carefully took her hand away, and I could feel the full weight of the boob pulling against my chest.
She repeated this with the other boob, and said "give them a shake", as she jiggled her shoulders so her boobs moved sexily.
As I did this I could feel 'my' boobs wobbling, but stayed securely attached, my cock was trying to swell, but was getting no bigger.
"Get dressed now" she said.
As reached down for my suspender belt, I was aware that when I looked down all I could see was my cleavage.
I suppose women are used to this, but for me it was novel, as I usually put my lingerie on first, then just put my silicone boobs into my bra at the end.
I was used to clipping my suspender on, so it didn't cause too much problem, but when I bent over to pull my stockings on, I found my boobs got in the way.
My wife laughed, seeing my problem, "tits do sometimes get in the way, don't they."
I ended up having to peer over my boobs to see what I was doing, as I attached my stockings to the suspender straps.
Then I pulled my panties on, and hiding my caged cock.
When I put my bra on, I could feel the relief of the support that the bra gave, as they were no longer pulling against my chest, and they enhanced my cleavage, and when I looked down I could not even see my own feet.
"What do you think" she said, pointing to the mirror.
I looked at my reflection, and certainly from the neck down, at a quick glance you would think it was a sexy woman dressed in sexy lingerie. Only when you looked carefully would you notice that the slightly extra bulge in the panties was more than you would expect, but considering I would be wearing a skirt, and my cock was totally contained and could not get bigger, no-one would suspect what was hidden under the skirt.
Then I wrapped my skirt around my waist, and put my blouse on, I began to think it might be possible to pull it off.
My skirt just about covered my stocking tops, just about acceptable for a workplace, but I would have to be careful bending down in case I flashed my lingerie.
I put on my makeup, trying not to be too tarty, which would not be acceptable for work.
Then finally my blonde, shoulder length wig to complete the look.
I looked in the mirror and looked at my reflection, and looking back at me was a sexy woman, but as I had toned down the make-up I was able to recognise the male me, under the make-up.
"I'm not sure I can pass properly, people might recognise me" I said.
My wife looked critically at me, then reached for her make-up bag " let's try this" she said.
Then selected scarlet red lipstick, and told me to pucker up, and put more lipstick on me "now I have got some lip plumping gloss, it will tingle, so don't be surprised. "
She put the gloss on my lips, and it felt like a thousand little bee stings on my lips, and I could feel my lips swelling.
" There, what do you think now" she said as she turned me to the mirror, "Make a feature of your lips, all people will see is, lips, tits, ass and legs."
I know what she meant. My eyes were drawn to my glossy red lips, looking even more voluptuous as they were more puckered, and I was hard pressed to pay attention to other facial features.
"Do you think you will pass now?" She said.
Almost u*********sly I nodded my head, my wig brushing my cheek as I moved my head.
" Just one last thing, to remind you of your position," she said, as she held up a butt plug.
I had never seen it before, and I wondered if the bought it at the same time as my cock cage.
I did think that considering every step I took reminded me of what I was wearing, it seemed a little unnecessary for an extra reminder.
The high heels changing my balance, the tug of my suspenders on my stockings, the bounce of my boobs, the sensation of my hair brushing my cheeks.
Also the smell, and sensation of my makeup, but by this point I had given up even questioning what was happening.
"Bend over the bed," she said as she put some lube on it.
When I bent over the bed, she pushed my skirt up, and pulled my panties down.
I felt the head of the butt plug touch against my anus, and I knew the best thing is to relax.
The pressure increased and I could feel it entering me, and then I could feel the fullness as it was fully inside me.
She then pulled my panties up, and told me to stand up.
As I stood up and walked about I could feel the butt plug moving inside my body, making my walk even more of a sexy wriggle.
"OK I think you are ready now" she said "we had better go in my car, as it would look odd for you to turn up in your car.
We can get a more suitable car if it all works out."
When got into the car, I had to think how to do it in a ladylike fashion, otherwise I would undoubtedly flash my lingerie to anyone passing.
I smoothed my skirt under my bottom, then dainty lowered myself onto the seat, knowing with the butt plug in it might make it uncomfortable to 'collapse' into the seat.
Kept my knees together and moved them into the car, then smoothed my skirt on my lap.
She dropped me off a few streets from my office, and I had the sensation of hearing my heels clicking on the pavement, and a cool breeze under my skirt, caressing my bare thigh above my stocking tops.
As I entered the office building, I saw Ted, and when he looked up I could see him sitting up, as though trying to smarten himself up for me.
I got to his desk, my heart was pounding in my chest, as I had greeted him for many years, and it would be the first test of if I would be discovered.
"Hello, what can I do for you" He said without the slightest hint of suspicion, so I assume he was take in.
" I have come to start work for Miss Blay" I said.
He looked puzzled for a few seconds " Miss Blay...........oh Linda " He was probably getting used to Linda's promotion. "Her office is just down the corridor, third door on the left."
It felt slightly odd being told how to get to my own office, and I don't know why I did it but when I said "thank you" I blew him a little kiss.
He actually started blushing, and looked down to his desk as though there was some important paperwork which needed his immediate attention.
I made my way down the corridor, and looked over my shoulder, and I could see he was admiring the view of me walking down the corridor, and when he realised I was looking at him, he had the expression as though he had been caught with his hands in the cookie jar.
When I looked ahead I saw some work colleagues, John, and Peter, coming towards me.
I had worked on many projects with them, and again the worry of being discovered crossed my mind.
As I walked past them, they must have thought I had immediately gone deaf as I heard John whisper to Peter "wow, sex on legs".
So obviously they suspected nothing.
It felt odd, but I knocked on what used to be my office door, and heard Linda say " come in".
I entered, and Linda looked up from her work.
For a few seconds she looked at me blankly, then the penny dropped of who I was.
" Ah you have come ready to start work have you" she said with a smile.
"Well I have got your name badge ready".
I went over to her desk (which used to be my desk) and she handed the name badge to me.
I looked at it, and read the name on it which had the name 'Sissy' on it.
"But my name is Susan" I said.
" I think this is more appropriate, you can always say you are an admirer of the actress Sissy Spacek, or tell everyone you are a sissy, I will let you choose".
I could see I was getting nowhere with this argument so I went over to her to get my badge, and she said "let me do it, so I can get it nice and straight".
I stood by her desk and admired the view of what she was wearing.
She had a suit on, with skirt which came to just above her knees.
Some women who wear suits seem to lose there femininity, but with Linda it was the opposite.
With her cleavage clearly showing with the first few blouse buttons undone, her hips tightly padding out the skirt, and shapely, nylon covered, calves clearly shouting 'I am woman'.
Her hands cupped my breasts and I could see her thumbs feeling 'my' nipples, she said "I bet you wish you could feel this for real".
I could feel my cock straining against its cage, as my imagination ran wild, and I breathlessly said "yes".
" Well you never know, if this all works out well, your dream could come true".
I was shocked at what she said, but it just made my cock strain more against its cage.
She then pinned my badge on, giving my boobs one more fondle, then she said "let's see what you are wearing".
I lifted the front of my skirt up, showing my pink satin panties, and matching suspender belt.
"Pink is such a feminine colour, isn't it" she said as she slid her hands across the front of my panties.
The warmth of her hand over my caged cock was driving me wild with lust.
She cupped my caged cock in her hand, and said "have you got something for me?"
I hoped that she wanted to play properly with my cock, so I eagerly gave her the jewellery box that contained the key to my cage, which was on a chain.
She opened the box, lifted it out, dangling it in front of my eyes, as though trying to hypnotise me, then put it over her head, and now the key was nestling in her cleavage, clear to see, so obviously a constant reminder to me that Linda and my wife control my cock. The only one who had no control was me.
"Anyway, we had better get on with work" she pointed to what used to be her desk, which is obviously my desk from now on "could you get on with the quarterly returns".
I let my skirt drop so I was (just) covering my panties and stocking tops, and thinking of my butt plug, dainty lowered myself on to the chair.
I turned the computer on, and opened the program to enter the figures for the return, when I became aware of a strange feeling.
It was as though the room was gently shaking.
I looked up at Linda, wondering if she was aware of it, and saw she was looking at me with a grin on her face, holding her mobile phone.
"Oh good, it seems to be working" she said.
She swiped her finger on the phone screen and suddenly the shaking became more intense, and I couldn't help but gasp, as I realised it was the butt plug that was creating the sensation.
It made me squirm on my chair, but as I moved the butt plug moved inside my body making the sensation more intensive.
This is what my wife meant when she said about 'reminding me of my position', it was so Linda could tease and torment me, even from a distance.
She then moved her finger on the phone screen, and I could feel the vibration change, corresponding with the movement if her fingers.
"I wonder what happens if I turn it up to eleven" she said, and her finger swiped up the phone screen.
It felt like a bolt of electricity shot up my spine, making my whole body tingle.
My cock was trying to burst its way out of the cage, and I could hardly think straight.
Just then there was a knock on the door, and the door opened and Mike Harding, my boss, walked in.
"Hi Linda, I thought I would pop down and see how you are settled in and ready for the presentation.
I know in all the years I had worked there, he had never 'popped down' to see me, but there again I could see his eyes lingering on Linda's cleavage, I suppose I didn't have the same reason for him to see me.
Linda quickly put her phone down, but the butt plug was buzzing away inside me, and I was trying not to wriggle about, not that it helped to lessen the effect of the butt plug, it just felt an instinctive thing to do.
He looked at me, and I suppose having a name badge on my chest gave him the perfect reason to ogle my boobs.
"Hello......err........Sissy" he said, with a slight smirk on his lips.
I felt myself blushing and stammered out "Good morning m......". With the buzzing inside me I could hardly think straight and I realised I had almost called him Mike, hardly the correct thing for a secretary to call the boss.
I looked towards Linda, who fortunately must have read my mind and said with a laugh "this is Mr Harding, my boss, so we had better be on our best behaviour".
"Thank you Mist......Miss Blay," damn I almost called her Mistress. "Good morning Mr Harding"
I was doing my best to avoid wriggling in my chair, as the buzzing of the butt plug was tormenting me, it was like having an itch you couldn't scratch.
Even working on the quarterly figures was almost impossible as all I could think of what was going on in my body.
My cock was throbbing all that it could within the confines of its cage, and I am sure it was leaking pre-cum into my panties.
Mike was standing by Linda's desk, going over the proposal for the new clients, while enjoying looking down Linda's cleavage, and knew the key for my cage would be clear for him to see.
I almost imagined he could read Linda's mind, and know the key was for my cock cage, and that caused some more pre-cum to leak into my panties.
Then Linda said "Sissy, I put some additional material for the proposal on your desk, could you bring them here please".
Oh god, I am going to have to stand up.
I was worried that my cock was so hard it would give a bulge to my skirt.
I gingerly eased myself up from my chair, and picked up the folder and had it covering my lap.
Because of the butt plug, it made my walk almost like a mince, with every step increasing the sensations.
I quickly placed the folder on her desk and quickly turned.
I could feel my skirt flare out possibly showing my stocking tops, but couldn't do anything about it.
I minced back to my desk, and to get to the 'safety' of the desk I almost collapsed onto my chair.
As soon as my bum hit the seat of the chair I realised my mistake.
I don't know if it was the sensation of the butt plug being thrust deeper into my body, or it touched some 'sweet spot', but I immediately started cumming.
I gave out a gasp, and Mike and Linda looked at me.
As my cock was spurting cum into my panties I managed to say "sorry, a bit of cramp", then grabbed the keyboard and started tapping furiously on the keys.
They looked away from me, and continued talking about the proposal.
I was typing total rubbish, but I did not want them paying any attention to me.
With every jet of cum, I had to suppress moaning out loud, and all I wanted to do is collapse over the desk, but I had to try to make it look like nothing was happening.
I seemed to be cumming forever, but eventually it stopped but I could feel my cum soaking through my panties and even trickling down my bare thighs.
When Mike had heard enough, and had ogled Linda's boobs enough he went to leave and said to me "if Linda keeps up this kind of job, we will both be under her".
I knew he was joking that Linda would have so many promotions she would become his boss.
But the image that came to my mind was both him and me, dressed as sissies, kneeling in front of Linda, taking it in turns to lick her pussy and ass.
My cock pulsed a few more times, but I could not imagine I had any more cum left in my body.
"Don't worry" he said "I'm sure I could find you a position in my office".
I'm sure the position would be bent over his desk, with my skirt pushed up, and my panties pulled down, and him thrusting into me.
I just smiled, as at that point I don't think I had any strength left for speech.
When the door closed I managed to gasp to Linda "turn it off", and pointed to where her phone was on her desk.
She looked blankly for a second, then realised what had happened and then quickly picked up her phone, and swiped on the screen.
It almost felt odd, to no longer having the incessant buzzing, and I looked down at my lap and I could see there was a wet patch on the front of my skirt, as my cum soaked panties soaked through to my skirt.
I stood up and said to Linda "look what has happened".
She saw the stain on my skirt and giggled and said "oh dear, have you wet your knickers".
I blushed as I felt like a toddler who did not know when to go 'wee wees'.
"I suppose the tartan pattern will dry, and not show too much of a stain, but you had better take your panties off, before it gets worse", she said.
I took my panties off, and cleaned myself up as much as possible.
Linda pushed her hands under her skirt, revealing her stocking tops, then hooked her fingers around her panties, and soon they appeared from under the hem of her skirt.
I watched as they dropped to her ankles, and she stepped out of them and held them up to me.
"Here, you can borrow my panties AGAIN, but this is not to be a habit, in future when I inspect what you are wearing, you will have to show me you have a spare pair of panties, in case you have another 'accident'."
"Thank you Miss Blay" I said, still blushing furiously at being treated like a toddler. Last week I was her boss!
I held the panties, and could feel they were real silk panties, black with red lace trim.
"Are you going to stare at them all day, or are you going to put them on" she said.
I quickly stepped into them, pulling them past my stockinged legs, past the bare thigh above my stocking tops, until my caged cock was surrounded by silk.
I could still feel the warmth from when they had been on her body, and I felt my cock twitch from inside its cage.
"So don't you appreciate being able to wear my panties again" she said.
I gave a curtsey and said "thank you Miss Blay for letting me wear your panties".
With a smile she said "I think you can do better than that" and perched herself on the edge of her desk, again hitching her skirt up to show her stocking tops, and spread her legs.
I did not need telling twice what she wanted, and fell to my knees in front of her.
As my head went under her skirt, I could smell the scent of sex, and closed my eyes, just wanting the smell to overload my senses.
I kissed her thigh above her stocking tops, then moved higher, waiting to feel the hairs of her pussy to start tickling me face, but all there was, was silky smooth skin.
I opened my eyes, and saw that where her pussy was very hairy last time I was sucking her, this time it was totally hairless, I mean NOTHING, not even a hint of bristle.
I assume she had been waxed.
My wife does shave and trim her pussy, but she has never waxed.
I let my lips, and tongue glide over the smooth skin, and then went down to the fold of skin where her pussy starts.
I heard her groan, and felt her legs part even wider, as I teased the valley of her pussy, obviously the sensation being heightened for her, as there was no longer any hair to deaden the sensation.
I wondered if my wife would have her pussy waxed, as for me it was as though this was the first time I had licked pussy, just silky smooth skin.
My tongue went deeper into her pussy crack, and I felt her clit, hard as though it wanted to be a cock, not hidden in the folds of flesh.
As I teased her clit, I could feel her juices soaking my chin, and even begin to trickle down my face.
I did not want to waste that sweet nectar, so I lowered my face so I could lick the juices from her sopping wet pussy.
My tongue pressing hard, entering her as much as possible.
Now I knew I was in charge of her pleasure, taking turns of entering her with my tongue, and teasing her clit.
I felt her body begin to tremble as she approached her orgasm, and I concentrated all my attention to licking and nibbling her clit.
I felt her thrusting into my face, whilst holding my head firmly into her pussy.
She only relaxed when her orgasm had swept through her body.
I licked the last of her pussy juices, then stood up in front of her.
She had a satisfied smile on her face, then stood up, straightened her skirt and said " I think you will be very satisfactory in your new role, but the quarterly returns do need to be done, and I have got a meeting to go to.
Also you will have to touch up your lipstick".
I went to my desk, and pulled a mirror and lipstick from my handbag, and began to reapply my lipstick as most of it was probably spread over Linda's pussy.
As she left the room and closed the door, I thought that her outward appearance was of a sexy business woman, but I knew she would be taking that meeting not wearing any panties, and the only thing covering her pussy was my lipstick.
It was then that it truly struck me that I really was my secretary's sissy secretary.

The end.......

I hope you enjoyed it, and comments are always appreciated.