I was sat at the bar sipping on a drink my handbag close by and a pad and pencil close at hand. My boss along with his girlfriend and myself where here for a meeting with a very important client from the states who wanted to mix business with pleasure so to speak. I was dressed in my neat two piece suit, it was a light grey jacket with matching skirt which had a slight split in the left leg something my boss liked although his girlfriend made sure I didn’t over do it. I was also wearing a white blouse buttoned just enough to show off my cleavage, underneath I also wore a tight fitting corset which pulled my waist in and pushed out my breasts, I was still amazed at how they had grown. I was also wearing a pair of black fully fashioned seamed stockings with Cuban heels very expensive and on my feet I wore a pair of black shoes with a 1 ½ inch heels not exactly what a modern secretary wore but for me with my knee very sensible, let me explain from the beginning how I got my current job and how I ended up much better off in both my life and work.
It started about 6 months previous with my being laid off work due to a small but unfortunate accident, I had been doing self filling in a local supermarket and had knelt down when my knee gave way, at the hospital it was revealed through x-ray that damage had been caused to my knee by my kneeling down on a foreign object and that the store was effectively liable for not providing adequate safety gear, I of course was awarded damages but had to give up that type of work which left me jobless, that is until I spotted an ad in the local paper, one of the local office companies was advertising for a new secretary no skills required as long as you could use a word processor, answer the phone and be able to take notes and if interested to apply in person the salary didn’t sound good but I could live with that. I decided to have a quick shower and shave and then dressed neatly (most bosses even modern ones prefer a presentable person especially when they are going to be on show representing the company) then I popped round to see what my chances were. When I arrived I had a sinking feeling as there were at least a dozen girls there and I was the only male. I gave my name to a middle aged woman sat behind a desk and she told me to take a seat and wait my turn. Each of the girls were shown in to a side room for an interview, eventually after what seemed like an age I was shown in. as I entered the room I was confronted by a large desk behind which sat two people one male the other female, as I approached the only chair on my side of the desk the woman looked up and examined me the man continued writing something down then he too looked up at me I was asked to sit down then the interview proceeded, the usual name and address and past work history a background history of myself, then came the crunch question “why had I applied for this type of work?” I explained that I had been laid off due to an injury to my knee and was looking for something different. I had noticed during the interview that the woman had said little but seemed to be studying me I found this unusual but not disconcerting, after I gave my answer they seemed satisfied and I was set for leaving when the woman suddenly asked what size clothes I wore I told her as best I could, again I thought this an unusual question but shrugged it off. As I stood to leave she asked me one more question “what was my view on ladies fashion?” an odd thing to ask but I answered that I thought they were ok but could always do with improvement “in what way?” she asked “well” I said “they could always do with larger sizes for the more bonny woman and not stick to old fashioned ideas of what a woman should wear” she seemed to like this idea then they both thanked me and said they would be in touch. I left thinking that would be the last I would hear from them. I decided to head into town and do some shopping just basic food necessities then went and purchased a DVD film I was after nothing fancy Casablanca I love old black and white movies and this was a classic amongst them having seen it on TV a few times.
It wasn’t until about a week later that I heard from the company, was I available for a second interview as I had impressed them with my answer about women’s fashion, I readily agreed and was told that the interview was at the couples own home and could I call this evening say around 6, I said yes and then went and got myself ready, a quick bath and shave then some clean clothes, I looked up a bus timetable for the nearest bus route and time that would get me there I didn’t want to arrive late so found one that would at least get me there early enough in case I got lost and needed directions. After a short bus ride and a lengthy walk I found my destination, it was a large house with a drive set back from the main road surrounded on all sides by trees and a double fronted gate, at first I thought I had the wrong place then when I checked the piece of paper which I had written the address on, I found I was at the right place, I took a deep breath then headed up the drive to the house. I rang the bell and waited with anticipation, my heart was pounding fast in my chest I could feel my hands were sweaty with nerves, I took several deep breaths to calm myself as I heard a dog bark somewhere in the house and a woman’s voice shouting for it to be quiet as she approached the front door it opened and there was the woman from the interview she greeted me warmly and invited me in. I stepped past her as a side door opened and the man from the interview stood there neither were dressed up but in casual gear I later learned this was their home, although they weren’t married but lived together I was shown into a large sitting room and was asked if I would like a drink I asked for tea as I felt it was too early for anything alcoholic. While the woman went and put the kettle on I was shown a seat and asked how my week had been what I’d been up to since the interview the usual icebreaker conversation. As I began to relax I learned that the male was called Steve and his partner was called Sarah and that they were both in the fashion magazine industry and they were trying to promote a new magazine aimed at the large sized woman hence the curious question at the end of my interview. Sarah arrived and passed me my tea, the conversation lasted for sometime again mostly about myself, my childhood hobbies what I did to relax in the evening it was during this that Sarah mentioned that I would have a good chance of getting the job I was delighted “but” she added “ there is one small detail you may not like” I had a sinking feeling something terrible was about to be revealed both Steve and Sarah looked at each other then Sarah said “ we need you to dress up as a woman” I gulped and nearly spat out a mouth full of tea, “sorry to surprise you with that” she said I looked shocked to them both and stammered “ you want me to dress as a woman?” “yes” they replied I thought for a moment and weighed up my options, I had the choice of being out of work for so long and my compensation money would only go so far, or I could do as they asked and dress as a girl and be in a job, I said “if I agree what wage would I be on?” it was Sarah again who answered “ providing you meet all the requirements and we are satisfied then I’m sure there would be an increase to a reasonable level” again I thought and eventually said “ ok I’ll do it, when do I start?” they both stood and shook my hand. Steve said he would have to get the contract drawn up and if I wasn’t busy this evening would I like to stay for something to eat I readily agreed, then Sarah suggested that later she would let me try on some of her clothes so I could get used to the idea.
We had a nice meal and whilst we left Steve to do the clearing up and eventual drawing up of the contract, both Sarah and I headed up to their bedroom, we entered a nice large room with a big double bed taking up most of the room centre of the room, along one wall was a large wardrobe with mirrors on every door, in front of the window was a large dressing table with a large round mirror looking closer I saw in fact it was 3 separate mirrors giving the illusion that it was one large one. Sarah told me to sit on the bed while she sorted some clothes she started off by opening one of the wardrobe doors, inside was a large selection of ladies clothes all very attractive and pretty, after a moment or two Sarah selected something she thought might fit me, it was a light grey coloured jacket, when she laid it on the bed I notice it also contained a matching skirt, Sarah was rummaging through the bottom of the wardrobe and produced a pair of black stilettos with a rather large heel, I looked at them and said “ I don’t think I could wear them, not with my knee” Sarah thought for a moment then replied “ just try them for now I’ll take you shopping tomorrow for something more appropriate”. Sarah then went over to the dressing table and opened the top drawer, sifting through she pulled out a black bra, matching black knickers, some stockings and a black suspender belt, these she place next to the outfit and told me to undress. I did so down to my under shorts Sarah looked at me and said “those too, don’t worry I’ve seen it all before” blushing I did as I was told though I quickly covered my manhood, Sarah giggled at that and then passed me the knickers I put them on and felt how smooth they were against my skin, Sarah next passed over the suspender belt, this looked a little tricky don’t get me wrong I’ve seen a few skin mags with sexy girls wearing them but for me to put them on seemed odd to say the least, I looked quizzically at Sarah who came over and undid the clasp then fastened it around my waist “that’s how its done, you could have just stepped into it like the knickers. Next came the bra again Sarah helped with this and adjusted it till it was snug “hold on a sec” she said I looked quizzically at her as she went to the next wardrobe and opened it to reveal men’ clothes this I assumed belonged to Steve inside was a drawer which she opened and produce two pairs of rolled up socks she passed them to me and told me to put them in each of the bra cups so I looked as though I had breasts. She looked at me and said “not the best of items to use but they’ll do for this evening. Sarah carried on helping me to dress and when I was done she had me sit in front of the dressing table mirror while she put make up on my face and brushed my hair in to place. When she had finished she had me stand and walk to one of the full length mirrors, I stood there open mouthed “is that me” I said I was gob smacked she really had transformed me “a little tweak here and there and you could easily pass for a girl” was her reply. We heard footsteps on the stairs and Steve entered the room he took one look at me and said “wow you look hot” I blushed at that I had never been told I looked hot as a male never mind being dressed as a girl. Steve then said “I’ve got the contract drawn up so when your ready you can sign it” I nodded my head whilst still admiring myself in the mirror, it was then that Steve’s mobile phone rang as he moved off to answer it Sarah said “ you’ve really impressed him looks like we have a new secretary” she gave me a hug and a peck on the cheek. I was about to get undressed when Steve returned “sorry about that, one of our new customers wants to visit and take us out this evening” “ I’ll change quickly and sign the contract and leave before they arrive” I said “ah there’s a slight problem he wants to make up a 4 some so I said I had someone here” Sarah could see I was getting embarrassed so stepped in and said “how long till he arrives?” “about an hour” was the reply “plenty of time” she said. Sarah sat me down whilst Steve left the room “I know this wasn’t what you were expecting tonight and neither were we” she said.
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