Emma's Stiletto Seduction Pt. 02

Part 2 of "Emma's stiletto seduction".

It is taken for granted that the human body cannot survive very long without a few terribly important things. What is the priority list again? That's right it goes Oxygen, Water then food. However there is a distinct lack of the word 'sleep' in this list.

Sleeping is perhaps the most undervalued commodity. It's taken for granted until suddenly it is no longer available to you. The events of the evening should have suggested that it would be easy to achieve, I was physically exhausted after all. But my research shows that there seems to be two variables necessary. The body has to be tired, yes, but so does the mind. And my mind was not at all tired, quite the opposite, it was still racing.

I had allowed myself after much deliberation to believe that the past few hours could be described as a 'success'. But only for a few seconds, whilst staring into the mirror and removing my heavily applied black mascara. I had achieved my goal to seduced a man, the only man that I have ever fancied, and now I was going to pay the price.

David seemed to have enjoyed himself, but men are more complicated machines that you first think. They can get off at the most mundane things, and think that a girl wearing a wet apron in the kitchen is 'sexy', but they remain a mystery in other ways. The irony is of course that many people would classify me as male too. But thats not how my brain is wired. I realised from a very young age that I was different. I was trans. For lots of parents of trans children they notice it first as preferring a certain type of toy, a doll instead of a train set. To play football rather than netball. Hockey over Rugby. Of course all that is completely ridiculous and has no bearing on the matter. Those things have no gender. To me, it was a built in sense of knowing something was wrong. That 2+2 did not quite equal 4. And when I started dressing, suddenly the mathematics of the universe fell into place. That must be it then.

Over the intervening years I had gone through the usual cycle of dressing, meeting and purging over and over. This is not me being flakey, but rather the guilt that society keeps tripping me with. Like it's wrong, or I shouldn't feel this way. I tell people who want to listen that I'm 100 percent over that guilt now, but that is a lie. Having successful meetings with gentlemen like David, who accepted and liked who and what I was, goes a long way. But for every step I take in my 6" patent leather heels, I feel the distance to the goal I need to achieve is doubled.

With my make-up removed, and lingerie placed in the washing basket in the small utility room of my first floor studio apartment, I felt naked. Not physically but mentally. Even though I had dressed to the nines, I had revealed all of myself to another person again. The not knowing how he will react to me the next day, because naturally our circumstance and fate would put us together somehow, was unnerving.

In my twenty-sumthing years of dating, if you allow me to call meeting strangers on the internet this, a large percentage of dates ended at the first. This could be my own doing, it could be mutual. But it could also be my partners decision, and that is where the agony lies. It's not like I wanted to meet again, but rather the option to have a repeat if I wanted to. When this is taken away, it's a feeling of loosing control. Having had someone so desperate to meet you, to have sex with you, and even cheat on their wife and family to be with you - and then to ghost you... well, it leaves a scar.

Incidentally I recall my record for being ghosted was before they had started the engine of their car when leaving my apartment. Their profile deleted forever from the forum. Anyway, I would also have to remember to drop my little black dress at the dry cleaners too. Sperm can and will stain leather if you let it.

An advantage of lying in bed wide awake mulling things over, is that you can find problems that you overlooked. The bedroom in my apartment was dark, but not completely black. Light creeping in though the lounge curtains found its way from the street lamp outside to the ceiling. As I turned my head away from the now dancing light, I could smell what had been curiously unsaid. Nail varnish.

Even if you have never worn nail varnish before you will know the unmistakable smell. It never looses the smell when you wear it, and the scent was clear to me even though my eyes were closed. Remember to remove it before work tomorrow. Work tomorrow? It's only Thursday. That's two days where I will have the chance to bump into him.

Our goodbye was said fondly, it suited us both to avoid the awkward sleepover.

'I'll just call an Uber," David said, "I caught one over here as we were having Champagne."

Although I engineered the date and very much wanted it, I didn't want him to stay the night. "Of course," I replied casually, "we both have work tomorrow. It's not a school night."

"Well I learned a lot!"

"You don't have to call me Miss Emma though, unless you want to?" I said, miming whipping a school cain.

If you ever want to see if a person you work with is a secret transvestite then simply look at their fingernails. They will be well groomed and just a bit longer than they should be. And if you look closely, you will see the remains of the colour they had last applied. Even when being very careful, there would always be a fragment left behind. Some colours and varnishes are worse than others. Red, bright red, is unfortunately one such colour as is blue. Black comes off really well, and at 3.30am it is probably just as well.

I had dragged myself into the office just on time. David and I both worked at the same place, but thankfully not in the same place, place. And yet still I was paranoid that the office gossip was all about me. Did they know about me, did they know that I went on a date with a colleague? Of course they didn't, how could they? But in my mind they had to know that 12 hours earlier I was on my knees with David from accounts' cock in my mouth. I hoped it wasn't all over my face.

But I need not have worried. Everyone went about their own day, too busy and wrapped up in their own problems to notice me. As morning became afternoon and afternoon became time to leave, my trepidation about David walking along the corridor to my office, in his dark suit and tie and shiny shoes, became a twinge in my stomach. Why hadn't he visited? Was he asking himself the same question about me? I tried my best to put it out of my mind, which only made me think about it twice as hard.

I was at home trying to distract myself with cooking, when my phone gave two monotone beeps. It was still in my work bag, a brown leather messenger style that I could throw over my shoulder and at least imagine that it was feminine. I didn't want to look, that's as much as certain, my phone never usually far from my side.

David: Thank you for last night, did you enjoy yourself?

Emma: Yes, very much so. Did you?

Before I pressed send, I thought about the lack of 'kiss' in his message. We had only previously exchanged number a few days ago, it was pointless worrying. Just to spite him, I will not reply with one.

David: It was great. I was just wondering...

Emma: Go on...

David: If Emma would like to come to mine on Saturday night?

Emma: That sounds good, what do you have in mind?

David: How about some drinks, nothing fancy.

Emma: So it's informal?

David: Oh I'll expect you to be formal x

Emma: As long as you are, sir. Shall I bring anything? X

David: No, but you can serve up if you like ;) Shall we say 8pm Miss Emma?

Emma: Sure, where are you again?

David: TN39 3EQ number 14, with the dark red door.

Emma: Ok, see you Saturday! X

"That went well." I muttered to myself, and then realised that It may be Saturday and I would have far too much time to plan.

My evening was spent going over various scenarios in my mind. I would normally have a set menu of exactly what is going to happen in a meet with a guy. What to wear, to be submissive or pro-active, and the precise type of sex that was going to take place.

I first started meeting when I was in my early 20s, with absolutely no plan whatsoever. Anything that happened had been spontaneous, but usually it was men asking for things I wasn't prepared to do or that I hadn't bargained for. Since then, I had insisted things had become more regimented, which had worked out better for both my sex partners and myself.

With David, we hadn't arranged this. I doubted that he would ask for a kinky sex-a-thon on a second date, after all, he was quite the reserved gentleman. He apologised after cumming in my mouth on our prior date! I was still not sure if that was a sweet thing to do, or a sign of repressed desires that had been bottled up for forty years.

Before work on Friday I ran my leather dress into the dry cleaners. Things had got quite hot on Wednesday, and I had also been quite slapdash when David had cum on my face for there was dried cum on the front of my dress. I recalled a tip as to never leave cum on leather overnight, always wipe it down with a wet cloth. That also saves embarrassment when handing it to the store assistant. Now it's just a dress, even if a sexy one, with no apparent signs that it had been successful in a previous seduction.

"Pick it up from Monday after 5," the assistant stated, "here is your number."

So my successful outfit was going to be out of action for my date. I would have to come up with another irresistible look to hopefully get a repeat performance, or at least not completely embarrass myself.

Friday evening was the last time I could really plan, the first thing would be to check out the house on Google maps. It sounds creepy, but as a transvestite travelling dressed this is an important step. What's the area like, is it busy? Is there parking? These things will definitely have an effect on both my outfit and confidence when knocking on the door.

Google revealed that Davids' house was a 1930s detached residence in a quiet residential area. It had both a garage and wide driveway, certainly enough for two cars if necessary. The rest of the street was a mixture of smaller and larger detached properties of a similar floor plan, with a cul-de-sac of bungalows fifty yards down the road. It struck me that the properties were only a half-mile from the sea, and yet the area didn't feel or reflect this. Balconies, blue glass and plastic cladding hadn't reached this area quite yet, but it was a matter of time I told myself.

Another thing to check was the weather forecast. Autumn had been warm so far, but it had taken a turn today. The outlook for Saturday was for an area of lower pressure and a chance of heavy rain showers in the evening. Typical, I will need a jacket. Rain is not a terrible thing for a cross-dresser, it keeps all but the most ardent dog-walker off the streets and so the chances of running into trouble are very much lessened. Wind, however, was your worst enemy.

In all my years of cross dressing, I have only been 'read' once. I had been walking home from a meeting and a car full of young lads pulled up next to me. Initially it has just been whistling and shouts of "Alright darlin'," but after a realisation that I was trans the cat-calls and negative comments began. Thankfully they drove off before the situation became worse, but I have never forgotten how badly things could have turned out. It was in the days before we all carried mobile phones too. Today, I will always have a plan just in case this ever happened again.

Meeting at the weekend is always worse than weekdays. Work provides an excellent distraction, and a Saturday at home with a 12 hour wait is far from ideal. I would make the best of it though, and it would give me plenty of time to have a long soak in the bathtub, even after a nap in the afternoon. It would be bad form to get tired at 10pm.

I had planned to leave my apartment at 7.30pm. It would take approximately 20 minutes to drive across town and find a parking space and 2 minutes to walk to David's house. I had decided against parking in the driveway, after all David was still a married man and could probably do without neighbours gossiping about strange women turning up on the doorstep. It occurred to me that David did not seem too worried abut this but still, I definitely did not want to be cited in divorce proceedings. It pays to take steps to keep as low a profile as possible.

After my bath I moisturised with a scent-less cream out of habit. Years ago I had been told not to wear perfume on a date as the scent would always get back to a wife or girlfriend they had not you told about. I decided to take a risk this evening and used my favourite perfume, a simple Chanel citrus fragrance. My outfit had been carefully laid out on the chair beside my king sized bed.

I picked up my black lace basque, size 32b. My breasts were growing, with age rather than hormones. Whether I liked it or not, I could tell they were changing over the last few years. My breasts could be considered embarrassing when in drab, but were becoming very useful for dating, men definitely liked them. False-breast forms of the past had given way to basques and padded push-up bras to give a real and natural cleavage. I sat on the edge of the bed, it was too high for my toes to reach the floor if i sat on it. Slowly I rolled on each stocking. Black, with a high denier, securing them with suspender clasps. My panties were black, of course, to complete the lingerie set. I tucked myself in as best I could, but it was something that became impossible to hide in the throws of passion. I was hoping that David would just ignore it like he had last time.

Looking in my only full-length mirror, it was encouraging to see a woman stare back at me. I rarely let men see me in just my lingerie, but if it were to happen tonight I had the confidence that I could not have prepared any better.

I pulled my shoulder length hair back into a ponytail and sat at the dresser to apply my make-up. I was long-past the cringing discomfort of asking a Boots make-up counter assistant for foundation to match my skin tone, it's definitely not a rare thing for men to use foundation, powder and 'guy liner' in 2021 thank goodness. But just in case, I liberally applied it with a trowel. Well, a finger and blended it with a large and very expensive brush.

Next was to apply fake eyelashes. A tortuous process but one that greatly enhanced the look I was trying to achieve. Charcoal eyeshadow, a pitch black liquid liner and heavy mascara gave me that sultry goth-look I had perfected over 20 years ago. I was too old to change and second-dates were not a time to experiment. I was lucky that I had been able to keep all of my natural fingernails from breaking. A layer of a neutral grey tone and two coats of glass black with a final layer of clear varnish was going to look an amazing contrast to my pale skin.

I styled my hair in a different way this evening, an asymmetrical bob. Instead of my usual centre parting, I combed more hair than necessary from one side, giving it an uneven shape, a collection of subtle hair-grips keeping it in place. It was black and glossy, something that David had loved last time. He was a big fan of the goth-look and this evening I definitely didn't want to disappoint him, so applied a deep-red lip liner and lipstick to complete me.

I selected large silver hooped rings, 3 inches in diameter, and placed them into my ears. I shook my head to see if they stayed attached, which they did. The clasps were tight. With the cold metal brushing against my neck, and the weight tugging on my ears, it felt like I was now Emma once more, the transformation complete. The 40 something goth woman looking back at me in the mirror was finally someone I recognised again.

I picked up the soft black leather pencil skirt from my chair and stepped into it. I pulled it up to my waist, and zipped the rest of the heavy silver fastener that ran vertically bottom to top. I pulled the skirt around 180 degrees so that the silver zip was now at the back, a trick that my mother had definitely not taught me.

As I was not wearing a dress this evening, I chose a white satin office style blouse. It was tight around my breasts and had three small buttons on each cuff. It was semi-transparent, and the hint of an outline of my black basque and straps were very much noticeable. I tucked the bottom of the satin into my skirt, and positioned it so that the hem of my skirt fell just below the knee. I could still walk, but the tightness of the skirt curtailed my stride just enough to let me know it was there, and force me to take smaller steps.

I took my leather choker from the drawer and attached it loosely around my neck, I could always tighten the buckle later just before I pressed the doorbell.

As I would be driving and walking, I decided against 6 inch heels. The weather has taken a turn, and boots would be appropriate. I selected a pair of black leather boots, with a 3 1/2 inch stiletto heel with a pointed toe. They zipped up from the rear, to complete the styling that I had chosen.

I prepared a strappy handbag into which I placed the following items.

iPhone

Car key

House key

Small travel hair brush

Lipstick

A 50ml tube of water-based lubrication

Hair scrunchie

Mint Tic Tacs

Soft black leather gloves

I grabbed my jacket from the hallway, a 3/4 length black leather coat with a button front and a belt at the waist. It was derailed with large exaggerated single-breasted lapels. I held my hand on the Yale-lock of my apartment door, turned it a quarter clockwise, and held it there. It was nearly time to leave. The apartment corridor seemed deserted, but I left nothing to chance. I didn't want to risk bumping into a neighbour like this. I lifted the intercom phone from the wall and listened carefully for voices in the car park outside. It was silent. I replaced the phone to its hook and turned into the corridor. It was carpeted, so I did not make a sound. I carefully pulled the heavy door closed and rested it on the latch, placing my key in the outside of the lock so that I could close it silently, and made my way carefully downstairs.

The car park was empty, and most other apartments were in darkness. The flats that had occupiers had thankfully pulled across their curtains. I'd left my car unlocked so that I could quietly open the door and get in without bringing too much attention on myself. The interior light made 5 seconds seem like 5 minutes until it extinguished. With my bag and jacket on the passenger seat, seatbelt fastened, I turned the keys and the engine purred into life first time. I blipped the Bluetooth gate controller and they slowly opened to reveal the road ahead. I drove through, stopped at the kerb, put on my headlights and then drove off into the night. My heart pounding, I have escaped. Stage 1 complete.

I don't know why I don't park at a meet location. Well I do, you never quite know what a person is like until you meet face-to-face as it were. As nice as they seem, as enthusiastic as they present online, you can never judge a person until they are standing in-front of you in the flesh. This has certain drawbacks, because if they say they are perfectly happy to meet a transvestite, it is another thing entirely to actually meet a transvestite. Especially if it was their first time.

I decided to park in the cul-de-sac near Davids' house. It would be quiet, dark, and I can adjust my hair and make-up without getting too much attention. Aside from the novelty factor of driving in high-heels, it was a relatively uneventful journey.

I pulled into the kerbside and switched off my headlights. The bungalows were set back from the road with bushes and shrubs just large enough to hide my car from their windows. Time to text David.