Emma's Stiletto Seduction Pt. 16

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

Emma's stiletto seduction 01 to Pt. 15 for prior entries.

Comments welcome.

We were, on the face of it, and extremely unlikely couple and certainly not one that anyone would have thought stood the test of time. But here we were.

It helped that we had been work colleagues and casual friends for a few years previously. We had shared the odd cup of coffee on breaks in the office and certainly got on well. But that was before things had changed for me. Before I had come out.

I have been trans all of my life, but a series of lockdowns over covid allowed me to live a completely trans lifestyle instead of it being thoroughly hidden from most people.

When the time came post-covid for the world to go back to normal, or whatever the new normal was, I didn't want to. I didn't want to give up what I had become.

A transwoman.

In the months of lockdown I had grown my hair out, it was long now, shoulder length. It was still black, jet black now, with the help of a bottle every few weeks.

The hormone treatment that my doctor recommended had started, finally, taking an effect on my body. At just 5ft4" tall I had an advantage over most people who transition. Combined with a small frame and the subtle redistribution of fat in my face, hips and chest, the results were already better than I'd hoped.

It was easy to go back to work as trans, after all it was really just an office environment. The company was large enough to be anonymous, beyond critical mass so that you can keep yourself to yourself. As the saying goes I came out, but not 'out out'.

I didn't dress fully in work, but more gender neutral. When the gossip went around the workplace that I was trans, for the first weeks I suddenly had lots of people dropping in to see me. They were intrigued, but disappointed not to find me with bleached blonde hair, lip fillers and 40 DD cup tits. It was business suits, hair tied back and professionalism. I wanted to keep things separate and not to become a pantomime show.

For those colleagues who were really interested, and not just for gossip, I was happy to talk them through the process and how it had affected my life for forty years.

There were things that I kept private though, like my sex life. They knew that I dated women in the past, but not that the vast majority of my sexual encounters since my 16th birthday had been with men. Coming out as trans didn't need to change this secret.

There was however one person who I shared everything with. David.

He remains a classic gentleman, in his 50s and married to the accountancy job. Especially now his marriage had irrevocably broken down. Another casualty of being thrown together for too long over lockdown.

After I had shared some pictures of the real me with David one day over coffee, he couldn't help but be interested and to see more. "In the flesh." As he put it.

After I invited him over to my apartment one weekend, our friendship had changed into a sexual relationship. A successful seduction on my part, but I maintain that it was he who allowed himself to be seduced.

"It was those high heels that did it for me, not you." He would tease.

We were both in the same place of our lives, throwing off years of repressed urges. David trapped in a sexless marriage to a woman who didn't appreciate him and me, a transwoman trapped in the closet by an ever regressed society.

David and I had grown close. Over the 12 months we had been together it was something that neither of us had expected. We looked forward to and explored sex, yes, but over the last few weeks I was asking myself the same question over and over.

Was there more to my feelings, were they stronger than just simply caring about a person?

"Ok," I thought, "He is the only man you have ever fancied."

And that part was true. But our fun relationship had definitely turned into something more.

I first thought about it a few weeks ago, when we were having sex in the shower. David had made me cum for the first time. Something that I have actively avoided with all but one of my prior male partners.

The other time was a reward, a gift to them, not to me. This time David had made me cum and I had welcomed it. It's easy to get carried away in the throws of an orgasm, but did my body and now heart belong to him?

I had not brought the subject up. It would be completely and utterly embarrassing if he didn't feel the same way about me, how could he? I was _just_ a transwoman and we had kept our relationship secret to everyone around us.

Our weekly routine, if you could call what exactly this is by a word that is so mundane, was now set. At work we would maintain our previous friendship, but not go out of our way to be together. Every Friday I would leave my apartment around 6pm and then stay the weekend with David until Sunday evening when I would return back home. Sundays became Monday morning, when I would quickly return to my apartment to pick up a few things and make it into the office by 9am.

If we met up Wednesday also, it was not unheard of for me to spend four evenings per week with him. Any regular couple would have bitten the bullet and moved in together by now, but David had not initiated a conversation about it. In some ways, apart from me, you may say that he was quite old fashioned. He was also still technically married, although as far as I knew they haven't exchanged words for a year.

And if we were to move in together, it had repercussions for work, family and the outing of not only my sexuality but also Davids.

We had never discussed that, technically, you could say that we were both bisexual, homosexual or even heterosexual. David was with a transwoman, and I was with a man. I didn't feel the need to label ourselves but I honestly did not how how he felt about things. We had just ignored it, got on with it, and that was that.

The best thing about our relationship had been trust. Something that we had both found we needed. David had been teased by his wife, "why do I stay with you?" for years. He had developed a fear of her leaving that kept him trapped.

"No one else would want you." She would say during an argument over why they never had sex, "I don't and I'm your wife."

Trust was necessary because of the above, but it was also because of my deep seated desire to have sex with others. I didn't want to be monogamous, something that I had made clear right from the start. It was always my wish to be open and honest with David and I was.

I was in a relationship with David, but on occasion I would need to have sex with other men. To be used by them.

It was so much a part of me, that I it would be almost impossible to remove. For 30 years I had played the part of the submissive woman with men during sex. It was the only sex I knew, the only sex I'd ever enjoyed. I couldn't give that up?

I needed to be a slut, I was a slut.

I needed to be a whore. I was a whore.

I needed to be used, completely and utterly by men.

This was Difficult for David. His insecurity would push against the above. But once he knew, really knew, that I would never cheat on him or lie to him, it was accepted. I wanted him to be part of this adventure... I wanted it became 'our adventure' as we would call it.

Of course there were benefits of having a partner who felt like this for David. He had found himself having group sex, something that he never though he would enjoy. It was part of his sexual fantasies, sharing his girlfriend, that he actually got to live out. But it began to push his limits, and I knew that one day I would have to make a choice.

Things were changing between us. I felt myself wanting and needing different things from a relationship. It was new to me, so new that I could not yet vocalise it.

He was still helping me with my desires, and seemingly accepting of them. Last time, David had agreed to acting out my fantasy of being with a stranger. The years of being used sexually by men was a difficult drug to give up. Could anyone really enjoy watching me be used? He was probably good at hiding his real feelings on the matter.

Out of the two of us, it was perhaps me who was growing more confused. Was I having second thoughts about being with others, or having David be a part of it? I knew that I had began to regret putting this man in such a position.

What was telling, was that I hadn't had such taboo thoughts in weeks. I hadn't daydreamed fantasies of being used by men as I masturbated, for a long time. All those dreams had gradually changed, and it was a shock to find that my current fantasies all involved David and making his come true.

I realised that he had given a lot to me, and was actually risking a lot to be with me. How would I feel if he said that he could no longer cope with sharing me?

At the moment, we were ok.

"Why am I so stupid to risk it all?" I would ask myself, "How would you feel if it was all snatched away?"

Even though I was in his bed late on this Saturday evening, I lay awake, my mind racing.

"It would be devastating." Was my realisation, which sent a cold shiver down my spine. I inched over the bed, so that my bottom nestled into his crotch. I felt the warmth of his body start to radiate though the thin black material of my neglige.

"It's ok," I told myself, not knowing if it really was or ever would be again.

I woke early, and readied myself for the day. We were going to 'our coffee shop' later on, and to run a few errands first. A typical Sunday.

If you had asked me 20 years ago what I wanted a typical Sunday to be, my current plans would seem like a nightmare. At that age it would be sleeping in till midday and then a nice breakfast to wear off the latest hangover.

But here I was, middle aged, and somewhat settled for the very first time.

"I need to pop in a couple of shops first." I informed David, handing him his breakfast of two eggs, poached, on lightly buttered wholemeal toast.

"Where?" he responded, his words muffled by an overly generous bite.

He checked the news on his iPad, uninterested in my response. "Marks and Spencers." I added.

Our lives were settled. Secure. I needed this after a night of insecurity.

In the UK, Marks and Spencer department store had become a place for the older generation, not that I thought we belonged there, but the clientele were generally older and so were the staff. The advantage was that hopefully it wouldn't be too busy at 10am on a Sunday.

This particular store was in a town centre, with its own handily positioned pay and display car park that was free if you did your shopping there. It was just off the M23 and not too far to drive from our regular coffee shop David liked to take me to.

It would take us twenty-five minutes to drive, and a few minutes to park.

"Not too busy?" David asked.

"I would imagine we are the first and possibly the only people here!" I exclaimed.

"It doesn't seem your style, if i'm honest Em."

"You would think that wouldn't you," I agreed, "but they have nice things and they are well made."

Ever the gentleman he got the car door for me and I stepped out.

"Don't worry, I won't be long." I encouraged as we entered the store.

I picked out some clothes and draped them over my left arm, still on their hangers.

"I'll need to try a few of these on, David."

"Ok, what shall I do?" He replied, with the realisation what shopping trips with partners usually descend into.

"You can stay out here with the other husbands." I suggested, showing him the convenient seating area for the abandoned partners of female clothes horses the store seemed to accommodate.

His look said it all, as he began to sit down and take out his phone...

"Or you could come in here with me?" I suggested.

His attention was immediately distracted by this, his eyes darting quickly around the store, then looking up at me.

"No one will bat an eyelid or probably even notice," I encouraged, "Hopefully."

David shook his head slightly, trying to get up from the fabric covered seat and failing to do so. His limb coordination deserting him for a moment.

"Anyway I'll be in here." I said, using the clothes over my arm to point to the fitting room at the end of the line.

His eyes followed me.

I always try and plan to dress smartly and not too sexily, to help us blend in as a couple. But I'm not yet that person. From and early age I understood that it couldn't be much fun for a man whose female partner always dressed in jeans and a T shirt. And, as a transwoman, I felt like I needed to always put in one hundred percent effort in how I dressed and how I acted. Otherwise men wouldn't be interested in me. I had to be above regular girls for men to be attracted to me.

"I see what you have done there." David said, as my high heels clicked and popped their way into the fitting room, echoing around the quiet store.

David followed.

The first time we had sex, I wore my best black leather dress. It remained his favourite out of all the outfits I had worn for him.

It was soft to the touch, and clinged to the curves of my body. Underneath I wore a push-up bra to give myself perfectly round B cup breasts. A suspender belt held up 50 denier black stockings and black lace panties tried their best to cover up my clit.

The look was so simple, so elegant when paired with a pair of 4"patent leather stiletto high heels that David could never resist. I never wanted him to.

I had tied my jet black shoulder length hair in a high ponytail and wore a strappy handbag over my shoulder. All it contained was my phone, some prescription sunglasses and my best red semi-permanent lipstick.

As I turned to hang the clothes I had selected from the store, David was there filling the doorway. His heart beginning to race now.

Quickly I pulled him inside the small room and drew the heavy dark red curtain across the doorway.

He remained there, motionless. Thinking that he should not be caught in here with me.

I stood up on my toes allowing the metal tips of my stiletto heels to leave the tiled floor by an inch, and whispered to him...

"Once you are not excited, or nervous," I explained, "then you shouldn't be doing it."

With the adrenaline quickly running through his veins, he understood.

We wouldn't be able to take our time.

"Sorry, but this needs to be..." I suggested, my eyes trying to silently pass on the need for him to cum quickly.

David nodded.

"Are you turned on?" I whispered, my right hand finding his cock through his trousers.

I need not have asked. It was already hard, erect and waiting for me.

I unzipped his trousers and pulled his cock out through the hole, holding it tightly between my fingers.

He leaned over to kiss me, and I pulled away, "No time for all that." I said, shaking my head a little, as I ran my thumb across the ridged glans of his penis, dragging his foreskin with it.

His cockhead was wet now, and sensitive as David twitched and jerked slightly though my rough handling of it. I reached into his trousers with my left hand, which found his testicles. I wanked his penis hard and fast with the other. David steadied himself on the wooden walls of the cubicle, his large 6'4" frame filling its width.

As I changed position, my heels clicked on the tile once more. I could feel David tense up, we both knew from the echo that it may attract unwanted attention if I couldn't keep them under control.

Now bent over and trying to keep my metal heels and soles of my shoes firmly on the ground, I took his cock into my mouth. There was no time for sentimentality here, my head bobbed up and down frantically.

I didn't let the cock escape, escape would mean extra noise. For once I didn't try and exaggerate the gagging sounds, trying not to let the cockhead hit my throat and just letting the tip and a short length keep running repeatedly over my tongue and lips.

David wanted to help, he felt the time pressure as acutely as I did. He unbuckled his trousers, releasing his penis from the scratching that the metal zip of his trousers had started to impart. It was easier now, his full erect seven inches was available to me.

He took his penis and started to wank it at pace, in ways that he knew would hopefully help bring himself to orgasm.

Surrounded by mirrors to the rear and sides of the cubicle, he watched as he vigorously wanked his penis into the mouth of his girlfriend. His eyes darted to the side, where he could see his cock disappearing and reappearing into her mouth.

He looked at the mirror in the rear of the cubicle. He immediately was struck by the large, grey haired middle-aged man looking back at him. His face was reddening with a mixture of effort and embarrassment.

Distracting himself, his eyes wandered down so that he could see my bottom and high heels reflected in the mirror.

"Yes, this is a better view." He reassured himself, his confidence knocked by the realisation that he was a older man doing this, no longer a young man in his twenties.

I concentrated hard on his cockhead, flicking my tongue quickly over the eye of his penis in the way I knew he loved.

"You don't regret the things you do, only the things you don't." He repeated to himself.

I rocked back on my heels and stood up, so that David could get a better grip on his shaft. His furious wanking no longer restricted by mouth.

"I want to see you cum." I whispered to him, "Wank yourself off."

I wanted to encourage him. I knew that the best person to make a man cum quickly was themselves. I could help by giving him the best view and inspiration to do so.

I licked my bright red lips in front of him, running the ball of my tongue piercing through my teeth.

David felt himself about to release, it wasn't going to be long now.

"Where do you want me?" He asked, suddenly unsure how and where his cum load would be deposited now his cock was no longer in my mouth.

I hadn't planned for this, the options we had were not many.

Rushing through my mind, where could he?

He could cum in my shoes, but I doubt that i'd have time to unbuckle the ankle strap - and I didn't really want to walk around with jizz there all day...

He could cum in my handbag, but my phone, lipstick and glasses were in there too.

There was no other way, he would have to cum in my mouth.

But it was too late, he was going to cum right now and there was no stopping him. No more time to prepare.

He pulled me close, the top of his penis finding the middle of my tummy as he felt the rush of sperm flow through him and empty over the front of my leather dress.

I frantically grabbed at the hem, making a cup-like barrier to catch the sperm as it hit my dress and quickly ran downwards, pooling into it.

He stopped after four big releases, resting his cock on me, sheepishly looking down. His face was a mixture of orgasm and shock.

We would have been quite the sight to anyone passing, but thankfully the heavy red velvet curtain had concealed us from view. David was stood over me, and I had sat back onto the single seat inside the cubicle, holding the front of my dress horizontally to stop the sperm dripping to the black stone tiled floor.

I bit my bottom lip, not knowing what to do.

David was still upright, in both senses, his adrenaline rescinding and the reality of the situation now starring to dawn on him.

We looked at each other, and I started to smile.

A huge grin started to creep from the corners of his mouth, which made me smile even more. I started to laugh.

I pinched the hem of my dress twice in between by thumb and index finger, which freed up a hand for me to cover my mouth.

David responded by bringing his index finger to his lips, and miming a "shush", which made me giggle even more as his eyes darted comically around the mirrored room.