Emma's Stiletto Seduction Pt. 17

Emma's Stiletto Seduction Pt. 017

This is a continuing story, my journal, please see :

Emma's stiletto seduction 01 to Pt. 16 for prior entries.

[Comments & directions welcome and appreciated]

Do you ever find yourself doing something. Something that a few weeks ago you would have thought completely unlikely if not impossible?

I made the call.

I contacted the local estate agents in the area. I needed them to value my apartment, in terms of sale price or monthly rentable value.

I had lived in my apartment for many years. It suited my needs perfectly when I purchased it. It is situated in a quiet street on the edge of town, with enough privacy that it was unlikely for me to bump into the other owners unless it was when exiting or arriving in the car park

It was anonymous, secure. Something that I strived to be in my rather unconventional personal life.

I had managed to keep myself private, and the fact that I was effectively living a double life had eluded my neighbours. Or if for some reason it hadn't, then they had not let it slip. Either way, the fact that I was trans, was none of their business.

After I had come out during the covid lockdowns at work, keeping it private at home was no longer necessary. I wasn't about to drop the local homeowners a note under their doors or host a reveal party. But if they happened to notice the person driving my car was now dressed entirely as a female would present, I wasn't going to loose sleep over it and neither should they.

Once you are out at work, or to family, those worries about keeping secrets disappear. The people who don't accept you were never really friends or family. Who has time for that hate in their life?

In the last eighteen months I was spending less and less time in my apartment, three nights per week were now spent at the home of my boyfriend, David.

David had a comfortable 1930s detached house. It offers us more privacy, yes, but most of all it offers more room. The commuting distance for both of us to work was about equal, we worked for the same large faceless company, and the house had practical benefits like parking for two cars.

Why do most things always come down to parking?

After David's wife had left their marital home, their relationship tipped over the edge by being forced to spend more time together, he was glad not to have the large property to himself. He had felt lonely returning to it after work finished for the day, and he felt it even now when I was not visiting or staying over. The house was warm, yes, but it needed people to bring it to life.

In contrast my apartment was cold, modern and sleek. When I was single it suited my lifestyle. I could let in gentlemen callers via the intercom system, and make sure it was all secure when they left. No one could venture to my door without my knowledge or say so because of this extra layer of protection.

But there was no need for this now. I found myself in a committed relationship, perhaps my first proper relationship that had now taken the next logical step.

It appeared that both David and myself had been thinking along the same lines for a while, but neither had the courage to say so. Our journey had seen us spending Friday night to Monday morning together, and then visiting on Wednesday evening too.

It was on a such Wednesday, a week ago, that the situation was finally aired in conversation between us.

We had just eaten dinner, my turn to cook, after which we were relaxing in the lounge. David was sitting on his sofa with a glass of red wine in his hand. I was on the floor, seated between his legs with my back towards him.

He was still in his office outfit, suit trousers and a crisp collared shirt. He had been earlier encouraged to remove his tie, which he did so after my encouragement. Even under my months of sartorial influence, casual did not seem to suit him or me.

My own office style was very much toned down, compared to how I would present in the evening or weekends. As I did today, I managed to pop home and change before meeting David for dinner. It was enough to exchange my office trousers for a Black leather pencil skirt which sat just below the knee, and my flat heeled ankle boots for a pair of 3 inch Mary Jane style patent leather high heels.

We were both looking at the television, even though the sound was turned low. It was a focus, background, to our conversation.

David took a sip from his glass and set it on the arm of the sofa. His right hand often found itself resting on my shoulder, or hooking a finger behind the black leather choker style necklace I was wearing. His hand may caress my ear, or casually fondle the ridiculously large silver hooped earrings I seemed to insist on wearing.

I didn't mind. I usually didn't notice now, but when I do notice his hands on me, I feel comforted. I enjoy it. I dressed for myself, yes, but it was a happy coincidence that men seem unable to resist casually resting a hand on my leather clad bottom. I definitely encouraged it.

My position was mostly on the floor, and I would find myself with my elbow resting on his knee, and sometimes I turned onto my knees to face him when he had cheekily said something to embarrass me. Or playfully rest my head backwards into his crotch and look up at him. I just wanted to remind him, and his penis that I was here. His hands would stroke my throat as it extended. Unsaid, we both knew what we were alluding to.

But it was no longer all about being sexy and sexual with each other. It had evolved into a closeness and a comfort.

David looked at the plain white face of his analogue wristwatch. It had just ticked passed 10.40pm.

"The time goes too quickly." He thought to himself as he ran his fingers through my straight black hair

He wanted to fill up his empty wine glass, perhaps only to half a glass... Even though I was at his feet he was still drinking alone.

It was usually about this time that I would have to tear myself away, for both of us work started at 8am tomorrow. It is a twenty minute commute, in good traffic, but it was rarely good traffic these days. If I had to leave as I should this evening, I wouldn't join David with drinks. Drinking and driving, no matter how little, never did sit well with me.

He slowly pushed himself up on the arm of the sofa, balancing the stem of his glass between his fingers. He was tall, plenty tall enough to step completely over me when i'm sitting on the floor like this, my high heeled stiletto shoes unable to redress the somewhat comical twelve inch height difference between us.

"Time for a nightcap," He said, pouring two fingers of wine from the decanter into his glass... and then he found himself saying it.

It was casual, yes, but was full of hidden meaning and depth.

"Would you like a glass, Emma?"

Our shared history shows that I could not welcome this. We both knew from the myriad of similar such Wednesdays that I would have to refuse, even though what I wanted was to accept.

It was 10.45pm now, and it would be at least eleven o'clock before I could get away. It would be 11.30pm when I got home to my appartment. Close to midnight when I had removed my makeup and got ready for bed. 1 am when my mind would stop racing and graciously allow sleep. Alarm set for 6 am.

It would be stupid to leave Davids' house, especially as the sound of the rain hit the large bay windows in the room.

But staying would also have consequences.

In the moment we would both silently play out the imaginary conversation in our minds...

"Ok, thank you." I respond to his offer of wine. "You know that I'll have to stay over now don't you?"

"That was the idea." David added, handing me my glass.

"I'll still have to go home early tomorrow though," I explained, "It means getting up at five-thirty."

David nodded.

"And you getting up at five-thirty with me!" I exclaimed, trying to remove the smile that had flashed over his face.

He sat back down, and tried to resume his casual playing with my necklace whilst I took a sip of wine from my glass. Glad that I didn't have to go outside in the storm that was clearly strengthening over the ocean that sat in front of the town.

"I can take you into work tomorrow if you like." David said, naturally.

Even though this may not seem like much, you have to remember that to the outside world we were not the couple we were in private. Certainly not in the workplace. Arriving together may cause our relationship to become public to people who know us.

"Would you be ok with that?" I asked, my heart racing knowing the future consequences of our actions.

"Yes." David replied.

His response was thrilling, and I couldn't wait to give my own reply to reassure him.

"I also."

When I gave my actual response to Davids' original question, us both having quickly weighed up the future consequences of our actions, it played out exactly as we had both imagined....

"Ok, I will have that drink. Thank you." I replied, and David filled my glass.

Suddenly, we had decided to move forwards together as a couple.

Being in bed together that night felt different. I had stayed over many times before, but dawn was about to break on a whole new day. A whole new life for both of us.

It was unfortunate that I didn't really keep many gender neural working clothes at David's house. I had wardrobe space and plenty of drawers, but I'd filled them with clothes that were not quite appropriate for the office. Outfits more for dates at the weekend, or clothes to be worn only in bedroom, behind closed doors.

After showering I made the best of things. Thankfully I now kept a full replica of my make-up cabinet at Davids' house, much to his initial chagrin, and a well stocked underwear drawer. The only trousers I kept here were a soft black leather pair, wide and boot cut at the leg. Aside from a jacket or two, I'd never really worn my trademark leather outfits to work. I preferred not to attract any attention and mix business with pleasure.

An old relative once offered me some advice, at which time I must have only been 7 or 8 years of age. "Never shit on your own doorstep." Was the highly inappropriate phrase. And here was I some 40 years later.

I very much doubt they could have imagined the scenario that would now be played out this morning. They were not wise to me using their phrase to remind me not to dress too sexily as a transwoman to work, for fear of causing issues.

I paired the leather trousers with a black shirt over my regular bra. The bra just added shape and support to my breasts rather than the push-up style that I wore on dates and outside of the office.

I had a smart dark grey cotton blazer jacket that I could wear, and placed my hair in a top knot that was fashionable for both younger men and women here now.

The only issue I had was with shoes. I did not want to go to the office in 6" high heeled stilettos, at least not yet. The only flat shoes I had were the over the knee boots that I'd left here a few months ago to dry out after I wore them in the shower with David whilst he fucked me.

"It would be fate., I thought to myself, "as they were what I was wearing when I first realised my feelings were a lot stronger than I thought for my boyfriend."

In any case I wore the long boots under my trousers, and no one could tell that they were actually approaching thigh-high in length.

Most trans people will be aware of this, but in case you don't know, this is called 'underdressing' in the world of cross dressers and transvestites for obvious reasons.

The day continued like any other and we need not have worried. As we drove past the security guard who controlled the barrier entry to the large work car park, they barely raised a glance away from their newspaper.

I had wondered if David would want to drop me off outside the automatic doors, or a walk away from the office buildings that were spread over a large site.

But he didn't vary his routine.

Inside, his stomach was in knots. He faught his self-preservation instincts.

"What if someone sees us?" He asked himself.

"And so what if someone sees us." He would reply

It was the same questions and answers occupying my brain also.

This early, the car park had 40 cars at most and David found his usual space, which I appreciated. I thought it unnecessary for him to open my passenger side door, he ever the gentleman, so I made sure to exit the car at the same time as David did to avoid any unnecessary embarrassment and attention that could cause.

We worked in separate buildings, so naturally we wouldn't have to enter a reception area together. The only remaining issue was how to say goodbye.

This first time, it did not matter. We didn't have to kiss or hold hands even though I wanted to. We had achieved, in a single small step, a milestone on our journey together.

It was enough for David to say very simple words, "Emma, text me when you need to leave tonight."

It meant that whatever happens, we would still be leaving together.

My office co-workers were all to aware that I was trans. My worry about swapping out grey office-suit trousers for black leather trousers hardly raised any comments. They were just about 'safe for work', and if anything much more appropriate than the very tight leggings that younger office women wore daily here.

Yes, I was still dressing gender-neutral today, ish, but I had upped my game.

At the 10.30am coffee break, I checked my messages.

David: How are things? x

I was glad that he was checking up on me.

Emma: Its all fine here, how about with you? X

David: I don't think anyone noticed us together x

Emma: The world keeps turning X

David: Let me know when you would like to leave tonight x

Emma: Anytime after 5, how is 5.15 for you?

David: No problem, I have a quiet afternoon. See you at the car x

Emma: Yes you will. X

My day passed without comment, although I did note more lingering glances from some of my older male colleagues. I didn't care if they fancied me more now or less. I was taken, not looking, off the market.

It was difficult for older colleagues to see me transition like this. Dressing neutrally helped them slowly make any peace they needed to in their minds about me. Rather than suddenly appearing full on as EMMA, tits pushed up and in stiletto heels with an accompanying slutty outfit.

Transition for me was going to be a gradual change, and each day was another step closer. It was so subtle that not even the oldest and least sympathetic dinosaur in the office would even notice.

After an uneventful morning, and with a complete lack or preparation, my next challenge would be to brave the food atrium. Thankfully it was so busy at lunchtime that no one really had time to notice me or the subtle change. I couldn't believe that I had been worrying so much about nothing.

I was already out, already trans at work, in black and white on my HR records. What was the worst that could happen if I started to actually become more feminine at work.

In any case David was also here in the atrium. I felt safe. I looked down at my phone.

David: I see you x

This was all he needed to say in a private message.

It was still light when 5pm came around, and the final challenge of the day. By 5.15pm I was casually resting against David's car, pretending to concentrate hard on my 'phone.

I was startled by a beep and the car doors unlocked. David strode towards me.

As we had exited together, we entered the car together. It was simple, so stupid, so small to everyone else. But as we looked at each other our hearts were racing, thumping through our chests. It wasn't a sexual thrill, it was relief.

We both felt emboldened. Excited about the future. Yes, eyes had seen us get into the car together. But at this point, as we exited the car park with my hand on his thigh, we were back together as one.