Emma's Stiletto Seduction Pt. 18

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Trans Emma risks all for anal sex with her Estate Agent.
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Part 18 of the 22 part series

Updated 02/08/2024
Created 07/15/2021
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This is a continuing story, my journal, please see :

Emma's stiletto seduction 01 to Pt. 17 for prior entries.

Comments welcome.

We arrived back at Davids' house still flush with excitement. To everyone else it was a normal Thursday, but to the two of us it was special. It was the first time that we have arrived at and then left work as a couple. Emma and David, together.

This may not seem like a milestone to many, but to a male and transwoman couple this is a huge thing. It was currently the biggest step that we had taken in our relationship together.

To our work colleagues we were straight. David liked women, and had been married to one for over thirty years. To the office he was the older single man, if being in mid to late 50s could qualify for that description. The 'divorcee' who wasn't actually divorced yet.

My status was a little more complicated. I was probably still considered middle-aged, now in my mid to late 40s, but that's where convention ended. I was part way though my gender transition from male to female. They could assume I too was straight, that I fancied women, and was happy for them to think that

I had kept my gender identity hidden from work for too long, it was none of their business. But lockdown and working from home had given me the opportunity to live my life as I now wanted. As a woman. And going back into the workplace as a male once more, giving up all the opportunities that finally being out as trans was giving me, well, it was never an option to go back to those dark days.

My transition would have been obvious to anyone around me anyway. Over two years of hormone treatment would start to reveal my growing breasts, redistribution of fats and of course a very expensive lack of body hair. Laser treatment doesn't come cheap. Transitioning doesn't come cheap. It takes a huge cost mentally and financially.

But it had been worth it. My slow transition to a more gender neutral person in work hadn't really caused that much fuss. If anything, colleagues were disappointed that I literally hadn't changed look and personality overnight.

But today things had changed. Having stayed over at Davids last night, unplanned, I had to go into work more feminine than usual. More importantly, we had arrived at work and left together too.

"Help me get these off!" I asked David, who was stood in the kitchen of his spacious and comfortable 1930s detached house.

I was sat on the second step of the stairs.

I had not been prepared to go into the office today without returning to my own apartment first for appropriate clothes. Having had a drink last night, and been persuaded to stay over with David, I had to make do with the clothes I already had kept here in his wardrobe and spare room.

The only appropriate footwear I had that wouldn't be too noticed, was a pair of black leather over-the-knee boots that were currently steadfastly refusing to come off. The lack of stockings in my outfit made sure that the boots clung tightly to the bare skin of my legs.

"Oh," David replied, seeing the helplessness of my predicament.

He rolled up the leg of my soft leather trousers that had hidden my boots all day. It had all be fine, apart from they were much warmer than I would have liked. They had become difficult to remove on my own.

David grabbed the foot of my right boot, as I braced myself against the stair post. It quickly slipped off my leg and folded itself in his hand.

"Next one then." He suggested, grabbing my left foot now and effortlessly helping me out.

"Whose turn is it to cook?"

For David, we have become as comfortable as old slippers, and, in my own way, as comfortable as my favourite pair of platform stiletto high-heels.

It may seem boring to you, but two the two of us this was fresh, exciting and we were sailing in uncharted waters.

Just like the previous evening, at 10.30pm the inevitable questions came around. We had just done an overnight, and there was no doubt that I would be staying over Friday, Saturday and Sunday evening also.

We were both on the sofa, David in his usual place with me at the other end. I sat across the seats with my freshly stockinged feet in his lap, casually trying to keep his cock hard without him noticing.

David had noticed what I was doing, how could he not, but he was happily ignoring this incase I stopped when he noticed.

"Is it time to go?" I asked, rather than telling him.

"Do you want to?" He replied, not answering my question.

Every day I had felt more comfortable with this man. Every day I felt myself wanting him more and others less. To the point that in my mind I was now monogamous. I may have retained the air of that side of my personality, wanting sex with other men, but I hoped it was buried.

"Yes, I really want to." I replied.

I purposefully didn't add 'if you want me to'. I no longer wanted to use words to protect myself, to give each other an out if necessary. I decided to say what I actually wanted to people, and hope that they wanted it too.

"Good." David added, reassuringly.

A moment passed.

"You stay here more now than you do at your flat." David acknowledged.

"Yes, I guess I do." I replied, again purposefully resisting adding 'is that a problem' to the end of my sentence to protect myself. I wanted him to know how I was feeling.

"You stayed last night, and now Thursday." David said, shyly. "And you will hopefully stay Friday, Saturday and Sunday."

I nodded. But I couldn't ask the next question. It wasn't my place. I hoped it would come.

"Why don't you stay Monday and Tuesday too?" David asked, looking at me intently now.

I looked back at him.

"Are you asking me to move in with you, David?" I said, realising that I had already just broken the promise to myself of not answering a question with a question.

"Because if you are," I quickly added, "I would say yes."

I diverted my gaze, and took a sip of wine.

"Yes, I am asking if you would like to move in here."

"Then I say yes."

And that was that.

We were now moving in together. The first time that I had done so with any previous partner in my life, male or female. I wasn't sure how it would go, but I knew that I wanted it to work so much.

I did not want to spoil the mood, I didn't dare ask about the elephant in the room. Or rather, his wife's things that were currently stored in both the attic and garage.

"I'll have to pop to the flat at some point this weekend though." I said,moving my mind onwards, "Otherwise I'll be going to work in thigh boots on Monday."

David smiled to himself, remembering the fun we had the last time I had worn them for him.

The weekend was spent ironing out any logistics of what should happen when we lived together.

"Will you need help moving?" David asked.

But I really needed to do something with my apartment. It was too big an asset to lie empty, and if I did have a flat to run back to, would I just do that the first time we had an argument?

Either way, we decided together that it would be best if we had some ideas on its sale value and if I was to rent it out how much its monthly rentable value was. I was sure that I did not want to take advantage of David's generosity by moving in, and having an extra income for us both would open up lots of exciting adventures. I had worked hard to own my property outright, and now it was its turn to start paying me back.

I left work early on Tuesday, I had arranged an appointment with an agent at 5pm back at my apartment. Life seemed suddenly so exciting with David that I didn't want to spoil its momentum. We seemed so happy, and I felt happy, for the very first time.

I had tidied the flat at the weekend when I came over to grab a few things. I had been living there for over ten years and it was surprising at the amount of clutter that I had amassed.

I didn't have time to change from work clothes, I would just have to do as I was. The estate agent would take me as they found me.

Even though I had been successful in apparently no one noticing me wearing my somewhat trademark leather outfits for the first time in work last week, I still kept it low profile. Today in the office I wore oversized cotton trousers in tan with black ankle boots. I wore a shiny black pvc blazer jacket that I could remove and suddenly become far less sexy in the office where necessary.

One or two of the older males in my building gave me glances when they previously did not. I guess it would be something I had to get used to as I slowly increased my outfits in work that matched my private life.

I took off my jacket over lunch, a strategy to help blend in with the workforce. I was underdressing though, with black stockings and lingerie. What people can't see cannot offend, outrage or even sexually excite them too much.

At precisely 5pm the intercom of my apartment alerted me, and I unlocked the front door remotely. I smoothed my black pvc jacket down tightly over my breasts, and for no reason whatsoever checked my hair in the mirror. It was still securely in the topknot I preferred at work.

There was a loud booming knock at the door.

The estate agent introduced himself, as "Mr Knight, but I could call him James."

"Thank you James, I'm Emma." I replied, and we awkwardly shook hands, my long fingernails scraping the palm of his hand as he withdrew it. "Please come in."

He stood in the small hallway, which led to the kitchen and then onwards to a lounge diner. Upstairs were the main bedroom, a smaller room I used as a dressing room and the main 'family' bathroom.

I had kept the apartment in a modern style throughout. It was a relatively new build and had not needed to be redecorated much since I had owned it.

"Why don't you go through." I said, inviting Mr Knight into the lounge.

"I'll need to take a few pictures if that is ok?" James asked politely, "And measure up."

James placed his case down on the green leather chesterfield sofa that I had inherited a few years ago. He did not take out a notebook or a tape measure, but a rather large mobile phone.

I looked back at him, quizzically.

"We do it all with apps now," He replied, reading my mind, "It makes a virtual three dimensional model."

He held the phone out at arms length, and it created a model, complete with measurements, live on the screen in front of him.

"Your viewers can walk around your flat without visiting," He added, "But I will still have to take some decent pictures, the technology is not quite as good at that yet."

I nodded, struck by his no nonsense attitude and confidence.

"Don't get into the shot," He suggested, turning quickly through 180 degrees, "Unless you want to be seen on Right Move."

I quickly moved behind him.

"But if you are it make help improve interest." He added.

"Is this the kitchen?" James asked, already walking though.

"Yes, this is the kitchen." I responded, embarrassed as he was already opening the eye-level oven.

"Of course he knows it's a bloody kitchen." I thought to myself, "What a stupid thing to say."

I honestly did not want him to be like this. When I rang the estate agency I hoped that they would send a woman. I hoped they would send an incompetent young woman who had never measured up or taken a photograph before.

But they had not.

James was tall, confident, and exactly what you would imagine an estate agent to be. He wore a dark suit and tie, and had the brightest and goldest watch plainly visible on his left wrist.

His shoes were black, and polished to a bright shine. I could not control my eyes, that were darting from his shoes and watch, to crotch.

I needed to get back to reality, I needed to "Stop this at once." I told myself.

I casually checked out his left hand. He was not wearing a ring.

"Have you lived here long?" he asked.

"About ten years." I replied, tucking a stray strand of my long black shoulder length hair back over my right ear and staring at the floor.

"Why are you moving?" He asked casually, looking back at me whilst taking some pictures.

At this point I knew that I should have just come clean. How difficult would it have been to say "I'm moving in with my amazing boyfriend, David"?

That was the truth. It was a major step forward in my life. Leaving behind everything I knew, to go on a fresh adventure. I wanted a clean break. David had indulged me, my 'old life' and my old desires to be used sexually by other men. But we had moved beyond that now. I hoped it was in the rear view mirror...

"Oh I've found a house I like." Was my late reply to James. My big stupid lie of a reply.

"Lucky house." James muttered to himself.

"Can you show me upstairs?" He asked quickly, returning to his professionalism.

"Yes, follow me." I replied, "It's up here."

I cringed once more at my clumsy words.

The first bedroom was a mezzanine with views over the lounge, and there was a door to the family bathroom to the rear. There was also access to another bedroom that was more of a single-bed box room. I used it as a private space to dress in my more feminine attire and for outfits that were for the bedroom only.

On reaching the top of the stairs I noticed the evidence, one that I felt the need to conceal. On the far chest of drawers beneath a dressing mirror was a large photograph frame. Rushing over I quickly took the frame and placed it face down. I hoped the estate agent wouldn't notice.

But James had noticed. The photograph was big enough for him to see it showed two figures that were holding themselves together tightly. One was a small female dressed all in black.

"It must be Emma." James thought to himself, "But why did she want to hide it?"

I honestly did not want to fancy this man, but felt that fate had dealt me with a very bad deal. James was precisely the man I did not want in my apartment. In my bedroom. I had put all of my previous life behind me. I no longer wanted to be a slut. I was moving in with David for goodness sake!

'OK so I fancy this man," I admitted to myself.

That's fine, I can't go through life not looking at other people. That's impossible...

"As long as I don't do anything it will all be ok." I thought, my mind concentrating hard on anything but sex.

Standard lamps.

Carpet.

Clock!

But it was too late, my secrets were about to be revealed whether I wanted them to remain hidden or not. I honestly wanted to be a good girl. I did.

As James open the door to the box room, I knew it was too far for me to prevent him finding out about me. Revealed to him in full 200 watt glory was my private dressing room.

I felt my heart physically sink into my stomach.

To his left were stiletto shoes, high heels of various heights from one inch kitten heels to 6 inch stripper heels. Beyond them were a selection of black leather boots. A pair of patent leather thigh-high boots caught James' eye.

All were carefully arranged, polished, and on show.

To his right were long and short hanging closets. Full of long black leather jackets and dresses. The short lockers were packed with a range of leather, latex and pvc skirts.

James was unsure if he should take a photograph of this. It was clearly an intimate space. He also knew now that the girl wearing a black leather dress in the photograph I had hidden was, most definitely, me.

"Wow." Said James, stepping backwards and regaining his composure. "You don't see this every day."

"Quite." I responded, trying to find my most demure accent.

"If you don't mind me asking," He boldly asked, "Is it a fashion statement or a fetish?"

This was most unexpected. I hoped that he would calmly close the door and move on without words being spoken. But he had turned his head towards me now, and clearly was expectant of an answer.

The real answer was fashion. It just happened that my fashion was apparently a sex fetish and a turn-on for lots of men. It was a 'happy co-incidence' I used to call it.

It would be easier for me just to lie and say 'fetish' rather than having to explain the actual reasons, so I did so.

"It's a sex fetish." I lied to Mr Knight.

His eyes lit up.

"Like a sub dom thing?" He asked, unabashed.

I took what felt like a minute to catch my breath and respond to his personal question.

"Yes." I lied.

"Which one are you?" He continued.

This was not how the conversation was supposed to go. I hoped that he would he able to find the rentable value to my apartment, and that I could move forward with my life.

And yet here we were.

"Submissive, sir." I replied, truthfully.

James stood still, his mind racing through the scenario that was unfolding in front of him.

"What makes you submissive?" James asked.

I paused, thinking carefully about my answer and what the consequences could be.

"I like to dress up." I offered.

"I can see that." James replied. "But how is that submissive?"

"I like to be used by men. I like to be used for sex." I responded, trying to be as casual as possible, not to give encouragement.

"Are you a slut?" James asked, looking directly at me now.

I turned away, I didn't want to face this man when I gave him my answer, when I betrayed my boyfriend.

"If a man wants to have sex with me, I cannot refuse." I explained. "I see it as my duty for my body to be used by them."

James was not used to someone speaking so candidly.

He watched the words leave my mouth through the favourable angle in the large mirror in-front of me.

"I really like your style." James said, looking back into my dressing room.

I nodded.

"I'd really like to see you in them." James said, looking at my tan coloured cotton trousers disappointingly.

And I now had a decision to make.

Would I go back to my old ways, of meeting strangers and being used for sex. Or would I be able to move beyond this, to step forwards and have my future with David?

James walked back into the dressing room.

He looked around, and took down a very short black leather mini skirt, size 12, from the rack.

Turning 180 degrees, he picked up a pair of 5" black patent stiletto shoes. They had clearly never been worn, at least not outside the bedroom.

"Put these on." He said, assertively, placing them on the bed.

I turned and faced away from him, and slowly let my tan cotton trousers fall to the floor.

I felt like it was happening to someone else and not me. I was following his commands, yes, but I did not have a choice to disobey. I was a submissive, now HIS submissive. It may be temporary, but in the moment my ownership had changed.

I could feel his eyes feasting on the pale white skin of my buttocks that were currently eating what remained of a tiny black g-string thong and framed by my stocking tops and suspenders.

Holding the leather skirt in front of me, I stepped forwards into the garment he had selected, and pulled it up to my waist. It zipped from the side. James could still clearly see the crease of my legs and bum cheeks, the skirt covered nothing, not even my stocking tops, and did not hide my modesty.

Surprised that I had done as he wished, James commanded me again.

"And the high heels too please, Miss."

I pushed my feet down into them, he had chosen a pair of spiked heel court shoes. They did not have an ankle strap to hold my feet in place. They would prove very difficult for my small feet to move any distance in and were definitely 'bedroom heels'.

I placed my arms by my sides and remained facing away from him. I was motionless, but I could feel my heart trying to burst out of my chest. I felt like the world was spinning, I was unsteady and rocked back on the thin metal spikes of my heels.

And I felt him come closer. If I was going to say 'No', now would be a very good time to do so.

The warmth radiating from his body flushed across my bottom and thighs. He stood close behind me, and lowered his head to my neck and started to kiss it.

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