Emma's Stiletto Seduction

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

Emma's stiletto seduction 01 to Pt. 32 for prior entries.

All suggestions, direction and comments welcome.

/

"My name is Emma.

I am 45 years old.

I have an MBA, and have been working with my current employer for 3 weeks.

I am technically bisexual, but I very much prefer having sex with men.

I was born male, but I am a transwoman. I have always thought of myself as a woman.

I transitioned approximately five years ago, and I have currently not undergone GRS or 'bottom surgery', but am under the care of my primary care practitioner and psychologist.

Legally, I am a woman.

Periodically, I take powerful hormones to suppress low amounts of Testosterone in my body, it makes it feminine.

I live in the house belonging to my boyfriend, David, and am currently renting out my old apartment out in the city. He is currently away on business and will be back in around two months.

I am a sexual submissive, and I love servicing men, especially with oral sex."

You may not think it, but just being able to say these words is a massive step forward for me, even in a trans and kink friendly forum like this.

For most of my life I have been closeted, keeping parts of my life compartmentalised. Sex, sexuality and gender all kept well away from my day-to-day life.

But now and only now., am I starting to realise that I can finally be who I was born to be.

I am a transwoman, and proud to be a transwoman.

Perhaps the question I've been asked most, by 'vanilla' people, is 'have you had surgery?'

They do not mean facial surgery, breast surgery or laser hair removal, for which I would answer no, no and yes. They are only interested in one thing - my penis. Or as us pre-op transsexuals would call it, our "clit".

During my life I had often thought that my final destination was to have it removed, or rather reshaped into its analogous form in a female body. But, as I have become older, and more comfortable with exactly who and what I am, my desire for vaginaplasty has reduced to zero.

Almost zero.

I am feeling happy being a pre-op trans woman, and the things that it brings.

I could be flippant and say that having a new hole in my body would be a curse!

50% more choice for a man to make when deciding what to fuck, when they can't even make their minds up in a supermarket just choosing a sandwich for lunch.

And, tellingly, if you ask a man what holes he really wants to fuck you in, the order is usually mouth, arse then vagina. With mouth being the most popular.

My own research suggests that for men, getting a blowjob is more popular than anal sex. And anal sex is more popular than vaginal sex.

Now don't get these anecdotal statistics confused, the most common type of sex is vaginal - but when asked what they prefer, that is when the men I know say 'blowjob'.

Why put myself through a major operation and 6 months to a year of recovery when I already have the two most popular places men want to put their cocks?

/

My life story is quite a speech isn't it, and certainly one that I did not expect to be sharing with anyone, especially with a stranger.

But today was not turning out to be a typical Wednesday, and it was about to get even more interesting.

Sitting around the restaurant table was my area manager, Charles, and a friend that he met in university.

It felt like that they had done lunch many times together, in this exact building and in this exact seating position.

But, of course, never with me in attendance.

Charles had made an appointment in the work rota, out of the blue, for me to accompany him to a business lunch stroke dinner meeting.

He had sold this to my store manager, Alex, as 'secretarial duties' required, who recognised the thinly veiled pretence immediately.

When Alex relayed the information to me, earlier in the week, he did so with a wry smile.

"He will put the address in the group chat." Said Alex, casually. "And don't bother coming back in store afterwards, I think you will be busy all night."

Later in the day I received the anticipated message from Charles.

Charles: Emma, you will need to meet me at the lodge for a meeting Wednesday. TN33 1AA at 4pm sharp.

Emma: Yes, Sir.

Charles: I'll get a table, and if you wouldn't mind taking a few minutes.

Emma: Certainly.

Charles: Oh, business dress.

Emma: Yes.

Charles: To impress, we may make an evening of it.

I had been made aware over the past three weeks that 'business dress' was a code used between the two managers. Everytime I was going to be interacting with them and not on the store floor, they had made the employee uniform requirements quite clear.

'Business dress' for Alex meant stockings with tight, short skirts and stiletto heels.

'Business dress' for Charles meant leather. He was clearly a fetishist, or very much had that as a kink.

A leather skirt or leather dress, and usually with leather knee high boots too. I had the impression that it could never be enough.

I had been able to keep a lower profile at work recently with Alex, he had only had sex with me once, which was on my very first day. He wanted to see how far I would be willing to go, and 'to be first to have a go on me'.

He did and he was.

Charles, on the other hand, seemed different.

Initially he had me suck him off 2 weeks ago in his car and once more after our probationary meeting a few days later. Then he went quiet, almost ghosting me. Just leaving me to be with my so called 'work boyfriend' that they had arranged for me.

This was a scheme the managers hatched to make our own sexual-favour arrangements a little less obvious to the other employees. To counteract many of my new colleagues being initially curious as to how much time the new girl was spending with the bosses.

They had arranged for me to start seeing a delivery driver, which worked well, but I had the impression that Charles was a little jealous of the driver in question.

I was perfectly happy with who they had chosen for me to "date", and the scandal around the workplace subsided faster than they had thought.

Charles arranging to meet me. and then fucking me for the first time before my 2nd date with the driver, gave me the impression that he was no longer entirely comfortable with his initial idea.

/

Having googled the address Charles had provided, I was surprised to find that it was a restaurant with a four star golf course attached.

The internet also suggested that it would not be busy at 4pm, the scheduled time, which suited me better.

I am lucky that I 'pass' in public, that is a term for not being 'read' by ordinary people on the street that I am a transwoman.

I would have no problem going to such a place and being 'read', because it is highly unlikely to happen. I am lucky, I suppose, that I pass as a woman. Unless I tell anyone, no one would know.

The only issue that draws any attention to me is Charles' idea of 'business dress'.

As you may know by now, I am more than happy to play dress up for men that I meet. It's part of me, it's how I like dressing anyway. It is actually a bonus to meet a fetishist like Charles as it suits both parties.

But dressing up is fine at a sex-club, or for a private one-on-one meeting, but I do attract eyes when it is done regular public venues.

It's out of place.

But on this occasion I decided to try and curb my concerns always telling me to dress down.

As I looked through my wardrobe I was tempted to wear my favourite leather dress. It always works, and has never failed to seduce a man.

But I wanted to make an impression, and had seemingly been given instructions to 'impress'.

I took from my closet a black leather skirt, size 12 and nothing too out of the ordinary for me. It would be tight yes, but at length a few inches above the knee. It would not be too indiscreet and would not reveal stocking tops if I sat down... but only just.

The top I selected was a standard white work blouse, I wanted to retain the 'office secretary look' as after-all this had been planned as a business meeting.

After our last meeting together, I decided this time to wear my hair down in its traditional sleek shoulder-length bob style.

And if Charles wanted me to impress, he was definitely going to get it. I had never had the opportunity to wear my thigh boots before in work, they would be literally a little too 'over the top', even for me.

As I had so many times before prior to meeting men, I would have to change into my black leather 'fuck me' boots in the car on the way.

Crossdressers will appreciate this, it is a rite of passage to get changed in a car for a meet, especially if you have to be discreet at home or have snooping neighbours.

"Thank GOD" I don't have to do this regularly anymore, I thought to myself. The awkwardness and the feeling of guilt and resentment reminding me of meets in the past.

I arrived at the lodge on time, at exactly 4pm as expected. The car park was only one-quarter full of mostly expensive cars and a fairly new company issued Range-Rover. A vehicle that I instantly recognised.

Charles was here already.

The combination of Black leather thigh boots and skirt was certainly striking, but I was glad that I hadn't gone too far. My handbag, worn with a strap over my blouse and on my hip broke apart my outline and added a distraction from my arse.

"Business on top, party on the bottom." Was my typical mantra when choosing outfits.

The maitre d'hotel was standing by at the entrance to the restraint and greeted me on arrival.

After pleasantries he asked, "Do you have a reservation." Unable to hide his bemused expression.

"I'm with the Heaton party." I replied, hoping that Charles had actually made arrangements for me.

"Ahh yes Miss," He responded, and gestured me to follow him.

The restaurant was smartly decorated, and my initial thoughts that it would be more traditional were dashed. Tables were large, circular, and built for entertaining. Some having eight covers or perhaps more, and perfectly decorated with white cloths. Place settings and crystal glasses were ready for evening service.

A half-dozen golfers were busy chatting at the bar after their rounds.

Sitting at the end of the main dining room, was Charles and a male associate.

The maitre d pulled out a chair for me to sit down, but as he did so the two men i would be dining with stood up to greet me.

Charles, as ever, was in a perfectly pressed dark business suit, although he had clearly earlier removed his tie to appear more relaxed.

His companion was of a similar age to Charles, and of a complimentary large build but shorter. If I had to estimate I would say around 6ft or 6f1 in dress shoes. As usual, all the men in my life seem to tower over me, although the 4" spiked stiletto high heels on my boots made me the average height of 5'8.

"This is my secretary," Said Charles, introducing me to the unknown man, "Emma."

He looked me up and down, and smiled, offering his hand across the table.

"You have done it again, haven't you." Replied the man, directing his conversation to Charles whilst he continued to hold my hand. "You only seem to employ the prettiest women."

"This is Mr Cauldwell." Charles quickly interjected.

"Cauldwell?" The man replied, "It's like being back in school Charlie."

Mt Cauldwell laughed to himself but still did not remove his light grip of me.

"If you want to," He said, looking at me properly for the first time whilst squeezing my hand tightly, "Call me Archie."

"Nice to meet you, Sir." I responded.

The chair that had been pulled out for me was in between the two men, Mr Heaton sat to my left and Cauldwell to my right.

"I will order some nibbles," Said Charles, "and we have more drinks on their way."

"On the business card I expect?" Archie asked.

Charles gestured with his eyes, rolling them slightly and shaking his head, convincing no one.

The waiter arrived promptly, carrying a tray with three large bowled glasses with exquisitely fine stems, and a second bottle of red wine.

He poured a measure in each glass in front of us, and busied himself when returning with a crystal water jug which he placed carefully next to four white wine flutes.

I was unsure what the arrangement here was, or the exact relationship between the two men. I had the inkling that they were old friends, and that they were somehow still on an equal footing with eachother.

"Do you work for the company, Mr Cauldwell?" I asked, politely, taking my glass of wine the waiter had left and placing it in front of me.

Again Archie chuckled to himself, although I was not sure why. Either the idea of working for our store or being called by his surname was the cause.

"No." Was the unison reply of both men, and "Old acquaintances." Added Charles, groughly.

"Are you going to make her wear the name badge all day, Charlie?" Asked Archie, looking at across as I carefully took out my notepad and placed it on the table. "Is she on the clock?"

"Of course." I interjected, trying to retail an element of professionalism.

"This one is well trained," Said Archie, intrigued, "I'll give you that."

I turned to Charles for an explanation, as clearly I was missing something important.

"Why don't you introduce yourself to your new friend, Emma?" Charles asked, "Oh, you can tell him everything."

I turned to face Archie, and began to speak.

"My name is Emma. I am 45 years old. I have an MBA, and have been working with my current employer for 3 weeks."

"Well thats nice to know, Emma." Archie responded, not thinking he would be getting my work history...

I did not need to turn around to I feel the touch of Charles on my left leg. He had placed his hand onto my skin, at the meeting point of the bottom of my skirt and the top of my boots.

He leaned over and whispered into my ear, "I want you to tell him everything about you."

He squeezed my leg now, making it clear precisely what he meant.

"Your CV." He added.

"Yes sir," I replied, and turned my attention back to Charles' companion.

"My name is Emma. I am 45 years old.

I have an MBA, and have been working with my current employer for 3 weeks.

I am technically bisexual, but I very much prefer having sex with men.

I was born male, but I am a transwoman. I have always thought of myself as a woman.

I transitioned approximately five years ago, and I have currently not undergone GRS or 'bottom surgery', but am under the care of my primary care practitioner and psychologist.

Legally, I am a woman.

Periodically, I take powerful hormones to suppress low amounts of testosterone in my body, it makes it feminine.

I live in a house belonging to my boyfriend, David, and am currently renting my old apartment out in the city. He is currently away on business and will be back in the U.K. in two months time.

I am a natural submissive, and I understand that I should use my body to sexually service men."

I paused, observing his reaction through my black rimmed spectacles, "My specialty is oral sex."

If anyone had looked closely, they could see my notebook moving in time with my heartbeat. It felt like it would burst through my chest.

"Blimey." Was the response from Archie, whilst not breaking eye contact with me, "You were not kidding Charlie."

"Indeed." Replied Charles. "I think I just got lucky in finding her."

Archies expression was a mixture of seriousness and incredulity. I wasn't sure if he was expecting me to be so frank and explicit.

It was the very first time that I had ever outed myself to a stranger like this. With each word I felt my confidence growing, and the shame of telling people receding. Now there were no secrets, and it was thrilling just to say the words out loud for once.

"I'm thinking of keeping her." Charles added nonchalantly, "but we will have to see how she progresses."

"You must be good then." Said Archie, turning his attention once more towards me. "Is she?"

I kept his gaze, even though we were just a few inches away from each other.

"I can show you." Suggested Charles, attracting his attention once more.

Moments later Archie received a message to his phone.

He took the phone from his jacket pocket and unlocked it.

"This is her, isn't it?" He asked in a rhetorical way, whilst quickly glancing between me and the screen.

In the past I had often sent explicit photographs and image of myself to prospective partners and hookups on dating sites, but they were always anonymous.

Even if shared with others, my identity could not have been deduced. The same with "action shots", I had always been careful.

But things had changed on my first day of employment here, when Alex had taken a picture of me for my security pass. An extra candid picture, as he lifted up my skirt, revealed that I was a transwoman.

Afterwards, on future meetings, both Alex and Charles had taken graphic photographs of me of the strongest kind... with their cum on my face.

My identity had been clearly visible under the white mask they had provided.

This had been the first time I had allowed such photographs to happen, and now I can see exactly what happens to pictures taken of me.

They get shared with strangers.

"AND she will blow you if you want her to." Charles suggested.

Archie was taken aback a little, but quickly regained his composure.

I felt Charles' right hand covertly pat me back with his palm, twice.

"Yes." I said quietly.

"She can't get anough cock in her mouth," added Charles, more loudly than was necessary in the public environment we were in, "it's her thing."

I remained poised as the words were analysed by Archie, his own mind now racing fast enough to match my own....

Buoyed by 2 glasses of wine, Archie got up from the table and turned back towards me, mouthing "two minutes" in my direction.

I nodded an agreement, that I understood.

Archie briskly walked across the restaurant to the restroom at the back of the dining area, thankfully away from the more accessible facilities near the bar.

Charles and I sat in silence, his right hand caressing the back of my black leather skirt, but with his thumb tucked into the belt at the top.

After 2 minutes without communication, I tried to get up from the table. But he had gripped my skirt tightly, forcing me to remain seated next to him.

I did not turn to meet Charles, but felt his warmth once more close to my neck.

"Go and suck his cock, Emma." He whispered to me, releasing his grip.

I stood from the table and smoothed down my black leather skirt across my bottom and thighs. I walked towards the toilet where Archie was waiting for me.

I knew Charles would be watching intently as I left. This clearly was HIS fantasy I was fulfilling today, not Archie's. His collegue was simply a collateral benefactor.

Every step of my leather thigh high boots clicked and echoed across the room, resonating with the Crystal chandeliers and glassware.

Charles was paying very close attention. This was what he wanted. A woman who was willing to fulfil his fantasies.

Situated off a subtly lit corridor, quietly, I knocked on the toilet door.

The lock clicked and I pulled the door open just enough to walk through.

The bright lights dazzled my eyes for a few seconds, and as they adjusted I could see that Archie had made the most of his solo minutes and had worked himself hard, ready for me.

He had sat back down on the toilet, the lid thankfully closed, but had his trousers and shorts around his ankles.

His shirt and tie were still buttoned and fastened tightly around his middle.

He was already very hard from his anticipation of a blowjob, and had been wanking his shaft for 60 seconds, not wanting to disappoint me.... perhaps, but most likely not to embarrass himself.