Emma's Stiletto Seduction Pt. 03

This is a continuing story, please see :

Emma's stiletto seduction

Emma's stiletto seduction Pt. 02

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Emma's stiletto seduction Pt. 3

I smiled up at him, "Yes, it was good from where I'm kneeling too."

David didn't seem to have an answer. This was the second time in four days that someone had sucked his cock. He felt elated and relieved, but also frustrated that this, THIS is what he has been missing out on for all those years of a wasted marriage. A determination came over him, and a silent pledge to take a chance and do this as often as possible in the years left that he could still get it up and perform.

He was in his mid 50s and had led, by many standards, an ideal life. Finding both school and college easy, and having a career mapped out by following in the family profession. He had studied accounting and banking at university. His father had been an accountant but hadn't gone to university and it was a great sense of pride in the family that David not only did so, but studied to do the same as his father. In reality he probably didn't have much choice and uni was inevitable. He always thought it was a bonus meeting a girl there and, not having much luck obtaining a girlfriend at school or college, he was delighted that after three years of studying together they never once seemed like splitting up.

Marriage happened soon after, more to satisfy her parents rather than necessity. But happen it did, and David has often thought that his life was rather like watching a soap opera on television. It was written by a scriptwriter and he had no input or agency over what actually happened to him and when. It felt predetermined.

The path of life for me had not been as cast in stone as it seemed for others. On the outside it should have been idyllic. A stable family home with working parents, an older sibling to look up to - certainly the envy of many peers at school. I was happy enough, and that was part of the problem. Perhaps I was too happy? For I only had one real issue. When I looked through the lingerie section of popular home catalogues that were ubiquitous in the 1980s, I wasn't like normal boys. I was't fantasising about the models in a curious way. I was much more interested in why my own body didn't look like theirs and how pretty their stockings were.

At the age of around 7 or 8 something changed in me, of course I will blame my sister for this. To her, it was an innocent game of dress-up. What fun it would be for her to dress up her little brother as a girl from the clothes from what we used to call the 'dressing up box' Even though it was many years ago, I can still clearly remember the outfit. A patchwork leather and suede mini-skirt, a blouse and my mothers high-heeled shoes. If you picture a child clumsily strutting about, trying to keep a pair of shoes far too large on their feet, well that was me. Naturally, they thought it funny and could not wait for my father to come home that evening and to show him what his son looks like dressed as a girl. But it was not fun for my father. In fact, he was disgusted and he quickly became angry at my sister for doing it and my mother for not stopping her. And also at me because, well, I probably deserved it too.

I so wish that incident had never happened, as, like many other t* girls back then, it was a clear sign that this was a bad thing. It was the first time I knew society thought it was wrong. And, if I was going to continue to do this, it had to remain a secret from everyone else.

You have to remember that the UK was a very different place back then. It was deprived, poor, with a lack of disposable income for each working class family. Men were hardworking, born shortly after the war and had to learn to look after themselves. Men had to make a living and be the breadwinner. Men had to like heavy drinking. Men had to join a union, a ' working men's club'. Men had to, well, be 'men'. There really was no such concept as gender, even though life was constrained by what would become known as gender roles. It was too soon for transvestites to exist let alone be visible. Now it's as simple as ticking a box on a form.

Non-binary

Transgender

Gender fluid

Woman (transwomen are women)

Man (transmen are men)

It is easy for me to sit here and say modern trannies have it made, when I know they absolutely do not. But I wish that I had been born 20 years later. When I wouldn't have to keep things so secret. I had often thought to myself, if I was 12 or 13 again, "Would I have done things differently?"

Life had come to a head over 30 years later for David. Moving house and the unfortunate necessity of spending 24 hours a day with his wife during lockdowns had finally put too much strain on his marriage.

"Probably stayed all this time to stop me from being happy," David pondered after she had left, "not because she was happy herself."

They had sex less than a dozen times before marriage and he genuinely felt that it was a similar figure afterwards. All of his passion, desires and kinks that he had allowed himself to fantasise about whilst masturbating were unobtainable. They hadn't had sex in three years, and he was embarrassed to think it was actually closer to five. He didn't know what he wanted, and the porn he had secretly been watching in his car when parked on the way home from work had reminded him that people actually liked sex. That it was normal to want it, and regularly too. And that he was very much missing out.

If he had his time again, David had often thought, "Would I have done things differently?"

And yet with such different paths, we had crossed again on Saturday evening. After daydreaming, our minds came rushing back to the present. We were both in David's candle-lit dining room and, in front of a red-brick fireplace, David was standing over me.

I remained on my knees, hands palm down on my black knee length leather skirt. The remains of his orgasm were still visible on my painted lips, a small droplet of white cum providing physical evidence of what had just taken place.

My legs were hurting, the pile of the carpet not enough to prevent soreness now creeping up from my toes and ankles to my knees and hips. The adrenaline receding, the immense down after the orgasmic highs had hit David hard. Could he take charge of the situation or would he leave me there in this submissive position forever?

"Whatever you do, don't apologise," I thought to myself, "or thank me."

"Thank you." Said David.

I could see that this was going to be a long learning experience for both of us.

Feeling frustrated I said, "I thought you were a gentlemen."

David became flustered again, suddenly feeling guilty, as if he had done something very wrong and shameful. He couldn't yet understand fully that a person actually liked having sex with him.

"Can you help me up?" I asked with a hint of encouragement.

"Oh. Right, yes."

David stepped over to me and held out his hands. I took them as he steadied me whilst I got back onto my 3 inch stiletto heels.

I've always enjoyed meeting taller men, and I was ashamed to admit on dating profiles that I wouldn't want to meet anyone who wasn't taller than me when I'm wearing my 6" heels. It just makes things easier, I told myself, and in reality it did.

"I think we should finish these drinks and I may let you pour me another one." I suggested.

"Yes, good idea." David agreed.

"May I use your bathroom?"

David hesitated, his eyes glancing sharply across the room and then back to me.

"Yes of course, it's at the top of the stairs and straight opposite, you can't miss it."

I smoothed the leather of my skirt with my hands, and tucked in my white satin blouse.

"I hope you don't confuse me with a sexy waitress." I shouted as I walked through the lounge and into the hallway, picking up my handbag from the hatstand.

"You do look rather like a maid this evening.." David responded as I was 6 steps up. I took it as a compliment.

There was a large oak dresser at the end of the stair landing, and I immediately understood why David was hesitant in his response to my question. Aligned in two rows were photograph frames, the centre one large enough so that it felt like it didn't belong there at all. It was of Davids' family.

Whether it was out of courtesy or guilt, many guys I have met previously have done exactly this. I doubt that it was actually to make me feel more comfortable, so I attached this action to David feeling guilty. It was in his nature. I tried my best not to look, to walk past the photographs holding my eyes out of focus. It is for the best.

I have only previously looked at family pictures a single time on a prior date. Well, what became a string of dates lasting several years. It was with a much older gentleman, who liked to watch me have sex with lots of men at the same time. This weekly arrangement suited me, when I was younger, but not anymore. I was now ashamed to admit that it once turned me on to be sucking off the husband, brother, father and grandfather of the family looking down at me in the pictures whilst strangers fucked me anally from behind.

David pushed his hand past his belt and into his trousers, rearranging his penis so that it was more comfortable. It was still semi-erect, not being able to rid his mind of the pornographic view that he had just witnessed.

"I'll pour some fresh wine," He thought, and busied himself in the kitchen finding two new crystal glasses. For him, drinking from used ones didn't feel right.

It was too late to be worrying now, but still he did so. If his mind wasn't full of thoughts about having sex, it was the guilt of having cum in my mouth again. It was now, after two dates, two orgasms to him and none to his date. He was actually keeping score.

His wife just never seemed to orgasm in the two dozen times that they had sex. She barely moved or made a noise. It was always the same position. Him on top, missionary, his weight on elbows. It always felt like it was an inconvenience to her that he took so long to orgasm, so he had taken to wanking himself furiously in the bathroom before putting a condom on and fucking her. Within a few minutes he had orgasmed, pulled out of her vagina and cleaned himself up.

By the time he returned to the bedroom, his wife had usually turned on her side, presenting her back as an indication that it was over. Her headaches and 'not in the mood' would probably last months now, as long as she thought she could get away with it. His current box of condoms that he dutifully kept in the bathroom cabinet were easily three years out of date.

"I will have to get more if this carries on." He thought.

I didn't turn on the bathroom light, it would be too bright. I doubted very much that I would still be attractive in the harsh spotlights recessed into the fancy plaster ceiling. It was best to use the light flooding in from the landing so that I could at least assure myself in the half-light that I was still a fanciable, classy lady.

I spat into the sink a mixture of saliva, mucus and sperm.

Taking a drink from the cold water tap, I rinsed my mouth three times and dabbed my lips dry with a piece of tissue. My lipstick had survived, again, another victory for the long lasting brand. I reached over to my bag that I had placed on the side of the white enamelled cast iron bath, taking out a brush that I used to straighten my hair once more.

I sighed as I felt the dampness of my groin.

"Must have been turned on." I thought to myself.

I pulled up my skirt to reveal my wet panties, coated with a stream of pre-cum. The material was not strong enough to contain it, and a patch of glistening white mucus coated the shiny black nylon lining of my once blemish-free skirt. With a clump of tissue I wiped the end of myself dry and adjusted my stockings back to being straight once more. I pulled my skirt back down, and noticed a tell-tale trace of dried semen on the front. I took some more tissue and held it briefly under the tap, not too much. As I wiped away cum the tissue paper lost its strength, turning one leaf into dozens of tiny particles of white. A towel was used to brush them off to the floor. It would have to do.

On the shelf above the sink was a glass bottle of pink mouthwash. I took a sip and rinsed my mouth again, spitting it into the sink and using my hand to sweep everything clean.

"These are the parts men don't worry about." I thought to myself, taking two mint Tic Tacs from my bag and quickly chewing them.

But to be fair, David was thinking about these things. He was thinking about how his wife was never satisfied during sex and was desperate not to start out a new relationship, or whatever the hell this was, in a similar way.

A short distance away I take care walking downstairs in heels, you never really want to turn up in accident and emergency like this.

David came through from the kitchen to greet me, carrying two over-full glasses of wine carefully balanced on a silver tray. I let him place it on the table before taking one.

"I should have waited for him to give it to me," I thought, "I want David to know that he is in charge of me."

"We are starting to make a habit of this." I joked, trying to break the ice once more and taking a deep drink from my glass.

"You don't mind?" asked David, his eyes firmly fixed on his shoes.

"Of course not," I responded quickly, "I am very much enjoying myself."

David took a drink himself now, his eyes darting to meet mine and then to the mantle.

"I mean you don't mind that..." He paused.

"Don't mind what Sir?" I said, trying to reinforce the power dynamic I wanted in this relationship.

"That. That you just suck me off." said David quickly. "That you don't get anything in return?"

"Look, it's absolutely fine if this is all we ever do," I replied, "I am more that happy to suck you off. If you can't tell already, I love sucking cock!"

"Really?"

"Yes really." I stated finally, and giggled as he watched me answer this most intimate of questions.

"So how do you, you know..."

"How do I get off myself? I asked.

"Well, yes."

"I don't think you want to know." I said laughing, and he gave me a quizzical look.

"Ok ok, why don't we take a walk and we can talk then?" I suggested, "It's a bit clinical stood here like this."

David looked through the lounge to the front windows. The porch light revealing the rain still coming down in what was a light mist.

"But it's raining." Said David.

"If you want me to answer your questions, you will have to come with me then won't you."

I finished my glass and turned on my heels, striding out of the dining room with the confidence that he will follow me. Naturally, inside, I was not confident at all.

I picked up my long leather jacket from the hatstand, it had dried and had been warmed by the hall radiator. I skipped the buttons but held it closed with the leather belt that pulled it tight to my waist.

I placed the long strap of my handbag over my head and took out my gloves and lipstick. As I was re-applying it using the hallway mirror, David squeezed past me, throwing his suit jacket over the stairway bannister and making his way to the landing.

David went into the box room. It was small, and was furnished as an office with a desk and a large hanging closet. He rummaged through, moving quickly from coat hanger to coat hanger until he came to rest at a tailored leather jacket.

He had purchased it on a whim, his wife ridiculing him when she saw it, saying that he had already gone through his mid life crisis 10 years ago. It had remained hanging there since that day. He carefully took it off the rail and brushed it with his hands. He slipped it on.

The fit was tight across his broad shoulders, but he could still get away with it. He turned and headed downstairs.

"Hey that's nice!" I said, "I haven't seen you in that before."

"I've had it ages, was just waiting for the right moment to show the world." He replied, grinning a large smile. "And I thought you might enjoy it."

I look his hand in mine, and led him through the front door. He turned and took a key from a green onyx dish and a small umbrella from the stand as he hooked the door closed with his foot.

I strode forward to the gate, my left arm dragging his right. He fumbled with the 'brolly before finding its catch, and it sprung open with a 'woosh'.

We must have been quite a sight, stepping out into the dark, wet and silent night. The umbrella was far too small for a man of six foot three to be carrying, and it was a squeeze to fit us both under its protection. I changed my hold of him, linking my arm though his as he tried and failed to keep us dry.

The quiet streets echoed only with the popping and scraping of my metal heel tips on the asphalt pavement. I had to take three steps to my partners two.

"You don't mind being seen out with me?" I asked, making sure he was ok.

"It's fine, nobody knows me here really."

"Oh charming!"

"I didn't mean it like that." David replied, pulling me closer and playfully nudging me so that my heels scraped a little louder for several steps.

In truth he probably did mean it. I had been on so many previous dates where men had not wanted to take my hand, just in case they were recognised out with a transvestite. They were quite happy to have sex with me, but not be seen with me. Perhaps he was just nervous as this was our first time.

"It's ok you know," I said, trying to relax him, "I've never been read when out with a man."

"What do you mean, read?"

"It's when someone notices you are trans. But don't worry," I quickly added, "everyone will ignore us. To them we are just a regular couple."

"You could never be described as regular, Emma."

He was right about that. It had taken me a long time to get over it, and a longer time to embrace the difference. There was certainly something different that trans women had to offer guys over cis women. Ironically the best thing was the reason I had kept myself secret from the world for so long, that dating a non-binary person, a cross dresser in my case, was still considered wrong. It was taboo. Even being out walking arm in arm with a transvestite was a rush for David. And he was about to find out how addictive this new drug could be.

In the distance a middle-aged man was walking slowly towards us, out clearly on a necessary errand on a night like this. I could sense David start to tense, not knowing what to do.

"Just keep walking," I whispered, "hold tight."

I allowed the bow-knot holding my jacket closed to loosen, and it gently fell apart revealing my outfit to the stranger.

As the man approached closer he changed his attention from the pavement to the rhythmic click of my stilettos. His eyes widened against the rain, the booted woman approaching him was wearing a shining black leather skirt, which aroused his senses further. Was she wearing black lingerie under her blouse?

"Yes!" The stranger thought, "Fuck, and a collar too."

His pace slowed as we got closer, until we were about to pass on the pavement.

He knew he shouldn't, but was hopeless to resist. As we all slowed to allow the man to get by without stepping into the road, in a single movement I felt him brush against me. And yes, his left hand definitely felt the small of my back and groped the cheek of my bottom.

"Did you see what he did, David?" I whispered.

"He actually groped you, touched you up!" He replied, shocked.

"Look back."

David turned his head as we walked on and observed the stranger, who had stopped and was pretending theatrically to look for his 'phone.

"He can't keep his eyes off you." David said, astonished that a person could be so blatant and ogle a girl in the street like that.

"He is probably thinking what a lucky man you are."