Emma's Stiletto Seduction

I have been in my current job for nearly seven years now, consider it largely office work across several sites. Usually once a week the job will entail moving from one site to the other, for a few hours, perhaps a day at most. It's not far or a chore, but you do lose your own kitchen facilities. Staff are very proud and defensive of theirs and don't like sharing.

I have been trans all of my life, ever since I can remember. I'm a trans woman, that's how I feel. I haven't lived completely openly as a woman, I don't know if I ever will. But I have dressed and looked the part in most aspects of my life apart from the workplace. I suppose it's because I'm part of the generation where being trans, or a cross dresser or a transvestite back then, was seen as shameful. Now, thank goodness, it is a more enlightened society and diversity is welcome.

On one satellite work site was a guy, or perhaps I should call him a gentleman, in his early to mid fifties. Let me describe him. He is of a large build, around 6'2" or 6'3" in height. And due to the ageing process, more rotund than I expect he would like to be. I think he carries it well. Handsome but not pretty. Greying hair but not grey. Most colleagues would describe him as genuinely nice, but quiet rather than outgoing. A noticeable thing about him, in his slightly shy and awkward nature, would be that he always, without question, wore a suit and tie to the office. Even when the business, event or weather that day would not warrant it. Always a dark suit, trousers, belt and jacket. With a white shirt and tie also. It made him stand out when their quiet personality did not. Well he did to me anyway.

He would always try and find me out whenever visiting my office, probably just to pass the time between jobs. General office chat was usually the excuse to try and sneakily use my kitchen. But that was also punctuated with the offer of a drink or bringing me coffee at desk to initiate a conversation. He was married, and if he had children they would have been off to university and beyond. It seemed that life didn't quite work out for him like that.

We had both been absent from the office over the past 12 months, anyone who didn't need to be there didn't have to be there. This new freedom had given me an opportunity to dress more, much more than I had ever had. I was feeling a lot more comfortable and confident with my own gender and how I wanted to represent it. Basically, its me, I'm trans but not transitioning. Being 'out' and the problems that could have come with that as a young adult were now beyond me. I just didn't care anymore. I didn't owe anyone an explanation. And in 2021 people are much less concerned that you happen to tick a gender fluid box on a form.

We had started to drift back into the office, a day at a time at first, and then two days became three. It was a matter of time before David caught me in the office for a catchup. The pressures of not getting out of the house and being confined to a few rooms for long periods of time seemed to have changed his home life and relationship. We can all agree that being forced to spend more time with family can be sometimes challenging, and it appears that it had taken a toll on Davids' long marriage. I didn't pry or get too many details, but it wouldn't surprise me to find that Davids' wife had left to look after elderly relatives. Just for a few weeks, nothing longer or out of the ordinary for their friends and neighbours to gossip about. That's what the clues suggested, unless you dug a little deeper.

Naturally I was asked how the absence from work had been for me, and in truth, it's been fine. Aside from watching more Netflix than is necessary, the most interesting thing about me was openly admitting that I'm gender fluid. This was said in an entirely matter of fact way, as if suggesting I've just had a cheese sandwich for lunch. What is a mundane admission for me, for why wouldn't it be as it's never been a secret to my own brain, was always a complete biblical revelation to others. Unless they are jerks, it's more of fascination to others and followed by a lot of questions.

"How long?"

"All of my life."

"Why?"

"It's how i feel on the inside, it makes me happy."

"Are you transitioning?"

"No!"

"Do you sleep with men?"

"Are you offering?"

It's always best left that way, colleagues don't need a blow by blow account of my past dating history. David was interested, thankfully not in a problematic way - but more of a way that they had never really thought about trans people or cross dressers before. There was a lot of new questions, but that's ok too.

"What do i dress like?" David asked in a quiet voice. "Do you have pictures that I can see?"

"Yes," I'd reply playfully, "but I'd have to tone them down for you."

Over the next two weeks I saw rather a lot of David, regularly popping into my office and once as I ventured over to the site where he works from. I got an increasing sense from him that things were not going too well at home. His wife wasn't back from visiting relatives, perhaps he was getting ever bored of his own company.

Conversations always started well, exchanging office water-cooler gossip, but usually ending with him being disappointed that Emma wasn't in the office.

"Will Emma ever come in to work?"

"Thats highly unlikely."

"Why not?"

"I've seen the the way you look at the office girls, you wouldn't be able to keep your hands of me." I'd reply, laughing and smiling.

The next week, as it was becoming rather regular, David popped into to see me on a Tuesday. It was always Tuesday. I have a feeling that he liked routine, and perhaps had a routine where he visited staff that were friendly with him on other days. Loneliness can occur for any of us, and after a long marriage and getting used to having people around, it was understandable to be lonely when this was taken away. I have been single for a long time, I prefer it this way as it allows me many more freedoms that wouldn't be available to me in the confines of a relationship.

I have been as I am for as long as I can remember, and if I had to categorise myself then it would have to be bisexual. An equal opportunities trans. I had fantasised about having sex with men and women since I learned what sex was, but it was easier to get with women. I knew that I wanted to try sex with men since i was young, but opportunities to dress and meet admirers were very few and far between. But thankfully the internet has resolved a lot of those logistical issues. I have had sexual encounters with men for 20 years now, being in my mid 40s. If I had a preference, it would be to have sex with men. And I've been with perhaps a dozen, some short term, some stretching out years. Never a relationship, but simply sex. However what I had not realised, surprisingly, was that I've never fancied a man before. I've had sex with them, sometimes within a few minutes of meeting for the first time, but I've never wanted a man. I have never thought 'phwooor' at the sight of them like I feel with some women. I've never had to seduce, beg or work at having sex. Sex was the main reason for meeting men, the only reason. It was a done deal. Meet, have sex, depart. No more, no less. Both parties satisfied.

It was a dream that did it and I rarely dream about sex. This was an exception. It was a clear, vivid dream where I was me, the real me, Emma, and in the company of a friend who I'd never actually thought of like that before. I'd never thought of any man like that before. Before I had opened my eyes, my eyes were opened. Things had changed. Forever. I fancied him, and it was difficult to admit it to myself, but I did. And that was that.

But how do you, can you, what can you do to set things in motion? It was a different world to me, no arranging to meet via the internet, no sure thing. No guarantees. For the first time in a long time I'd have to work at a seduction and Tuesday at work was the perfect opportunity.

I don't know how it happened, or why it happened, but the conversation between David and I turned to football. Of all things, bloody football. I'm not a fan, it was the talk of the office now that the national team were doing very well at the European Championships. The next game, scheduled for Wednesday.

"Why don't you come over and watch it with me?" were the words I felt coming of my mouth. Unnatural words, dangerous words for they could be rejected as swiftly as they existed. Did I really say that? Before I had chance to do much processing, David responded...

"Yes." David said, breathlessly.

"Well that's ok then." l replied, before he couldn'f change his mind. "Shall we say 7.30 at my place?"

"Yes," David responded and, after thirty seconds of silence, "Would Emma like me to bring anything?"

"Champagne!" I said smiling.

"Emma has expensive taste." David laughed. "Tomorrow at 7.30 it is, I will bring a bottle."

"Here is my number, you have pulled."

Making a date, if this is indeed what it was, is traumatising at the best of times. Making a date as a trans girl is doubly so. At least I had the hint that it would be ok to actually dress, perhaps be expected to, by my date. David was obviously comfortable with the idea, and had not been repulsed by the pictures that I had relented to show him on my phone. If anything the reaction was of surprise at the effort that I put in and that it wasn't just a game or fetish. It was simply natural.

"If i was single I would really fancy you," David admitted, "I had a thing for goth girls at college."

"Did you ever get lucky?"

"No, but I don't think it's ever gone away."

"Well," I said with a confident smile, "you will get your chance tomorrow night."

It was coming up to 11am, and David was due in approximately 32 1/2 hours. Things had to be planned carefully, but at least I'd have time to do so as it was very unlikely that I would get much sleep. Before meeting men for sex I would always play things over and over in my overactive imagination. It turned me on knowing exactly what I was about to do.

I fancied him and he is coming over tomorrow. I can't seduce him can I? Is he even seduceable? After all he was still very much married, even if they we not currently together. Would I get another opportunity? I usually trust my instincts, and if he wants to be seduced who would I be to stop him? Indeed all of the stops would have to be pulled out tomorrow evening to make it happen.

Tuesday evening was a time for tidying and planning, and more tidying. Thank goodness it was a date to watch a football match with drinks. I wouldn't have to cook and that was quite a relief. Although my maids outfit could have got an airing. I thought it would take me a while to decide what to wear, but in reality it is cast in stone. When I needed to look as desirable as possible, I have to play to my strengths. My style has always been a bit goth, but not overdone. The chosen outfit was carefully laid out on the armchair next to the bed of my studio apartment. Shoes tucked safely underneath. I was never usually a jewellery person but I decided to make an exception just this once.

Everything had to be just right. I wondered if David was worrying as much as me right now? My mind wandered to how many times I had dressed up for a meeting only to discover that my chosen date has turned up wearing casual or work clothes. Too many times. Errors in arrangements were now a thing of the past, I made sure of it. If you expect me to dress up for you, you have to do so for me.

"I dress in thigh high boots for you, and you turn up in a tracksuit?" I would scream at them. "Well don't expect a fucking blowjob from me." I'd end up blowing them anyway after a few drinks.

But would David do the same or would he be super casual? Would I fancy the out-of-work David instead of the slightly shy and nerdy workplace professional David?

My fears about not sleeping through the night before a date were revealed to be true, how can you sleep on occasions like this? Like a child at Christmas I thought to myself, pathetic! But exciting nevertheless. This is what being a transvestite and sleeping with men does to you. It's the adrenaline rush that's absent in other sexual relationships. It's addictive.

I was dreading work the next day, but it proved to be a welcome distraction from the pending events. Wednesday morning was sufficiently busy, although I found myself glancing at the clock and counting down the hours until 7.30. I'd have to get home by 5pm, 5.30 at the very latest. With luck the traffic would be on my side. My attention went from the office clock to my mobile phone. No sounds or calls would be good news. A text could only be bad news. If I didn't look it couldn't be bad news, right? All of these things were new feelings for me. And then it beeped. A message. Don't look. A message from David. Definitely don't look. A message from David confirming 7.30pm. I had cheated and looked. But now I feel sick with nerves.

Text: Oh, how tall are you? Emma X

Text: Six two I think, why? David x

Text: I need to know what size heels to wear XX

Text: I like six inches. David x

Text: So do I ;) Em Xx

By 5.15pm I was home, all was well. Straight upstairs to run the bath. My skin had to be soaked, legs had to be smoothed. It's now 6.30pm, where did the time go? Ready to start my make-up. I sat at my dresser in-front of one of the only two mirrors I allowed in the place. False eyelashes first then foundation. Plenty of foundation, smoothed and then dried with powder. Eyeliner and eyeshadow next to apply, liberally in my favorite goth look. No risks to be taken. Butterflies rising. Should I pour myself a red wine? No. Complete the nail varnish first, gloss black.

I could leave nothing to chance, I had to dress in a way that I felt confident. Confident that if this didn't work with the seduction, nothing would have. Stockings, naturally. Black with a heavy knit denier and lace stocking-top. Nothing fancy, no seam necessary but a slight sheen to them in the lamp lighting I was going to employ. A black basque which had been lightly boned to help keep its shape, with lace breast cups. Again simple, classy I hoped, with four suspenders that I dutifully attached to my stocking tops at the front and rear. Panties, black, thong-like and barely able to keep in anything that I needed to keep private. Dress, a soft black leather, above the knee, size 12 with sleeves descending to below the elbow. The neck of my dress was cut squarely at the front and a 'v' shape at the back, not low enough to reveal my basque. The hem length of the dress was perfect to conceal stocking tops whilst standing but high enough to expose them whilst doing anything else whatsoever.

I would usually tie my shoulder length jet black hair back in a high ponytail, but I thought that David would like it if I was smarter. He always presented himself at work perfectly. I styled it in a bob that fell just below my chin and combed it straight, resolutely straight to within an inch of its life. Not a single hair out of place. Earrings, large, silver hoops three inches in diameter. Collar, black leather, silver studs and buckle. Very goth. Bracelet, silver, on left wrist. Ring, silver, worn on left hand little finger. Ring, silver, worn on left hand middle finger. Ring, silver worn on left hand thumb.

Make-up was completed with heavy red long lasting lipstick. It was a miracle that none of this activity smeared my nail varnish, it still not completely dry but good enough if I take care dressing. I glanced at the clock, 7.20pm. 7.25pm, 7.29pm. 7.30pm. The intercom to the block of apartments rang. David had perfect timekeeping.

To complete the outfit, I always keep the shoes until last. They give me the confidence to meet strangers, and the sexiness to be desirable. They were perfect black patent leather stilettos. 6" heel with a 1 1/2 inch concealed platform. They were brand new and box fresh. I stepped into them.

I pressed the intercom and within 20 seconds of releasing the main door catch, David was standing behind the door to my apartment. I looked through the spyglass. He was in a suit and tie. Of course he was. Bottle of champagne in hand, blushing and looking flustered as ever. Unbeknown to him, I was standing twelve inches away watching, equally flustered. Quite nervous too, with only a door in between us. Although I was expecting it, the knock made me jump. My heart was banging hard against my rib cage, chest rising and pulling the supple leather of my dress taught across my c-cup breasts with each breath. I opened the door and revealed myself.

The initial shocked look on Davids face turned to an incredulous look, which turned to a stutter and a silent physical offer for me to take the Champagne Bottle.

"Hi I am Emma," I said trying to break the silence, "it's nice to meet you. I've heard so much about you."

He smiled, "it's nice to meet you too, I'm David."

After a moment in the hall I gestured to move to the lounge.

"Please, come this way."

"After you," he said charmingly, with a glint in his eye.

Usually this is done in a chivalrous way, but I always get the feeling that men say this just to get a look at my arse, which incidentally is definitely my best feature. As David followed me, my heels clicking along the engineered oak floor, I could feel his eyes burning a hole into me. I imagined him drooling.

"You look...," he stammered.

"How do I look?" I replied.

"You look amazing. Just wow."

"Thank you sir," I said, clicking my heels purposefully now i know they have an audience.

"Why don't you make yourself at home whilst I put the champagne on ice," I fussed, "and I'll find a couple of proper glasses."

"This is great champagne" I shouted though from the kitchen.

"Only the best," was the response, 'I don't get out much."

I placed the ice bucket containing the opened champagne on a silver tray that already had two crystal champagne flutes readied, then paraded into the lounge. I placed it on a casual table next to the green leather three seater antique Chesterfield that I had inherited from my parents a while back.

"Why don't you sit down David," I suggested. "The game will be starting soon,"

He looked confused, of course, it was the apparent reason why we were both here. As he walked past me I noticed how tall he was. Even in my 6" heels my small stature made him another six inches taller than me at least. He sat on the sofa and I poured him out a glass of bubbles and passed it to him. "You don't mind me getting dressed up?" I asked, casually.

"No, not at all, in fact, well, I love your outfit, my..." and then he paused, and looked towards the window.

"Thank you," I said, his gaze returning back to the room and focussing on me, "I don't make this effort for just anyone." He Blushed.

"Thank you for coming over, let's have a nice evening," I toasted, raising a glass.

David stood up from his seat to continue the toast and in doing so, stood a little too close to me. I had to stumble, rocking back on my spiked heels a little. Davids' free arm quickly placing itself around my waist steadying me. It remained there, around me, touching the cool black leather of my dress. I felt his warm had rubbing my back, subtly, and then it was removed as quickly as it came.

"Sorry." he said, blushing at his clumsiness.

"That's alright. It's any excuse just to touch me."

We clicked the glasses together making a beautiful chime. Time for kick off.

With drinks in hand, we sit back on the sofa, taking a seat at opposite ends. The sound of my leather dress on the chesterfield provided pleasant friction squeaks. The game starts, both staring at the screen but not really watching. We take sips from the glasses. The champagne goes down very well and helps us start to relax in each others company. This was the very first time we had been together outside of work and the first time Emma has spent with him.