Emma’s Stiletto Seduction Pt. 38

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

Emma's stiletto seduction 01 to Pt. 37 for prior entries.

All suggestions, direction and comments welcome.

/

I had woken still wearing the clothes I had worn from the night before.

But this was not an accident from being sleepy or too drunk to change. I had done this deliberately, to extend the time until the moment I had no choice but to change.

It reminded me of when I was younger, just finding my way as a transvestite before I even knew what a transwoman was.

To remain hidden, I would dress in secret. But when you are young that time is restricted. In daytimes I'd be in lessons, and spend the evening with my family. Nighttime was the only time I would have to really be alone, and I'd dress then. Even if sleep would come immediately, at least I figured I'd be sleeping in stiletto heels.

I had lain on top of the bedclothes, curtains open, street light bright and seemingly

in full view. But in David's darkened bedroom no one could see me, not even the neighbours in the well-to-do house directly across the street.

My outfit felt precious, a map of everything, events that had happened last night. Every scrape could tell a tale, and every scuff a story. My blouse, skirt, stockings and high heels were very much ruined.

My body felt the same.

It had been the first time that I had the attention of four men at once. They had taken advantage of my submissive nature in all the ways you would expect them to.

I didn't have to move on the bed to know that I was was sore from their penetration, and that my lips felt twice as big as they should.

Without opening my eyes, I wiggled my toes. Yes, they were still tightly strapped into what was once a new pair of black leather 4 inch high-heeled stiletto shoes.

I let my legs slide from the bed so that my feet felt the bedroom floor. Technically, did that count as me being out of bed?

Thankfully my shift at work would not start until 10am, which would provide time to make myself somewhat presentable to customers at the department store.

I opened one eye, and then closed it. The pressure of mascara and dried sperm made it feel like too much hard work.

It had not been too late when I got home yesterday, perhaps 10.30pm, but after a half-bottle of red wine failed to quench my adrenaline, I felt forced to take matters into my own hands...

To masturbate my 'clit' until I reached orgasm.

I recall that it did not take long to achieve the first, only a few seconds. Every detail of the group encounter was still vivid in my memory which quickly pushed me over the edge.

This was typical of orgasm for me, and had been for decades now. Having sex with men and then coming home to pleasure myself.

Alone.

I had rubbed my 'clit' hard through my black leather skirt, tracing its shape before taking my fingers and running them across its engorged tip.

I came in my knickers, but it seemed that once had not been enough. It would never have been enough to catch up with the experience.

So just to confirm incase you didn't know already, transwomen like myself can still get erections and can still cum, even after my years of hormone treatment.

As I sat up on the bed I could feel my own ejaculate still wet in my groin. There would be no need to undress before a shower, what would be the point.

I managed to make it into work on time.

I was scheduled to work on the department store shop-floor today, both managers Alex and Charles were away, which suited me fine. Their constant sexual advances and demands would not be present.

When on the 'floor' I would try to wear flat shoes, the job involved a lot of walking unless I was needed in the management suite. And, although regular sex with the bosses was a condition of my continued employment, it's important not to forget that I still typically had a full workday to perform as well.

The bosses had consistently reminded me that they were not paying me for sex, that was their "perk", not mine.

I doubt that would satisfy HR.

Today I wore my new size 8 black pvc dress. It was a subtle matt leather effect, rather than shiny rainwear type material, with a square neck and three quarter length sleeves. It was knee length, and with it I wore my 1 inch high patent leather kitten heeled knee boots.

All store assistants could wear their own clothes, as long as they were within the colour guidelines of black trousers, skirts and dresses or with a white blouse. You had to wear your ID badge or lanyard at all times so customers would identify you as staff and could ask you for assistance.

I had not had much time to style my hair into its natural shoulder length bob, So instead wore it in a high wet-pony.

Make-up covered the redness and swelling around my mouth and lips as best it could.

To look at me, no one would immediately think of the rough treatment handed out to me by the gang of men at the woodland dogging site just twelve hours earlier.

The only outward signs now were my fingernails. Although I had not lost any of the long acrylic appendages, they definitely needed to be lacquered on my break at lunchtime.

To the casual observer, it was just a regular workday for me. However, in the moments that I had to myself, my mind was extremely quick to wander back to the events of the previous 24 hours.

I would catch myself adjusting my knee-high boots, or re-styling my hair in the glossy reflections of glass displays.

Smoothing down my tight pleather dress, letting it cling to the remaining curves on my now petite frame.

There was no way for my colleagues to know what I had done, or the gang-banged slut I had become.

But the customers, any one of them, could know.

All the men in the woodland last night knew my name, my real actual government name, but also knew where I worked.

They could be watching me right now, waiting for their chance to approach me.

What would they say?

What would they want from me?

I only knew that men who were confident enough and sexualised enough to frequent local dogging and cruising areas would likely have the willingness to come and find me here. Perhaps not to approach, but certainly to see if it was all real.

To see if I was real.

But it was only day one, was I simply flattering myself that they would instantly come back for more?

I realised that I would have the rest of my life, or really my life in this locality anyway, of wondering this...

It must've been what, say 5 pm in the late afternoon when he came into the store.

It was always quiet at this time and the store closed at 6 pm. It was usually a dead hour in the workplace, the staff used it to tidy and close down the departments, but the managers liked the opportunity for shoppers to still make a purchase. In reality that rarely happened unless it was a named holiday like Christmas.

I first noticed him in the glassware department where I was stationed. Even though I've only worked in store for two months, it had not taken me long to discern if a customer was simply browsing or wanting to buy. This person was neither.

Through the corner of my eye, I watched him casually pick up an object and clearly pretend to investigate it carefully but at the same time giving it no attention.

At this distance, I did not recognise him immediately, but it was possible he was one of the men from last night. Definitely not the tallest one, who took the lead and lifted me from the car and then first ushered me into the woods.

Allowing myself a longer glance than was necessary confirmed that yes, he was one of them.

But unlike yesterday he was on his own and in a very well lit public area with cameras positioned all over the store.

After two more minutes of his charade, I felt him approach me and the desk that I was stationed at. I purposefully held my back to him, heart pounding, to force him to make the first move.

The man had placed his palms onto the desk, and I felt his eyes like lasers drilling into me.

Even though he had intimate knowledge of me not 24 hours previous, this situation was different. The lighting was different the dynamics were different. I was different.

Physically I was the same, but much shorter with 1 inch kitten heels compared with the 4 inch stiletto high heels I was wearing last night.

My hair was different, tied back into a tight ponytail rather than my precise shoulder length bob, not that it had stayed like that for very long thanks to their treatment.

He did seem sure it was me, but not perfectly sure.

I heard the word, "Emma?" whispered in a low but strong voice.

I turned around to meet him, and his eyes, first fixed on mine, then to my name badge that confirmed everything he needed to know...

No, it was not a fantasy.

Yes, I was a real person.

I've met lots of men over the years, and it never ceases to amaze me how much time they have seemingly spent planning for these initial moments and yet nothing about what comes next.

It was not my job or role to tell him what he wanted, he would have to tell me and I would have to provide that service. In work and in my private life.

"I..." he said cautiously, and then corrected himself, "WE wanted to see if WE could find you."

I remained silent.

"I wanted to make sure... WE would see you again."

I nodded.

"You clearly enjoyed yourself," he grinned sarcastically, "and you look like you've come through it okay?"

I nodded again.

"It wouldn't matter if you didn't." he added, "Not anymore."

I felt like he had come to give me an ultimatum, a threat that somehow if I didn't agree to see them again, that something would happen to me.

But what could he say?

What could he do?

I had realised in the moment yesterday that I was free of this, free of this guilt. Unable to be bullied and manipulated anymore.

He looked me up and down.

"Anyway", he said quickly, "is there anywhere more private we can go here?"

And I knew what he wanted. He wanted me, again. And I knew what, as a woman, I was created to do.

"Follow me." I replied, quietly.

I secured the till at the station and walked through the store to the central escalators. I didn't look back, but I knew he was behind.

My kitten heels were small, but they still had tiny metal tips that caused the hardwood floors to echo as I popped and scraped across them.

I stepped foot on the escalator and two steps behind the man still followed.

I knew he must have been looking at me, his eyesight would be level with my arse, my small black fake-leather dress clinging tightly to every curve.

He would see my dark stockings briefly over the top of my knee high boots.

I knew that the manager suite was empty, and used my security pass to enter. The man tailgated through the door quickly after me.

I let myself into the last office on the right hand side of the corridor. Its blinds were already pulled down and I listened as the door clicked itself locked behind us. Precise and irreversible.

He let the silence stretch, purposeful, almost ceremonial.

"You really didn't think I'd find you here?" he said.

"I thought the woods was the end of it." I lied, telling him what he wanted to hear.

He shook his head once, amused.

"Oh sweetheart," he said, voice low. "That was the audition for us."

I exhaled, "Audition?"

He leaned just close enough that the words felt physical.

"You passed," he said. "Obviously."

"Obviously." I thought to myself, pleased with my debut dogging performance.

"You stood with your back to me on the shop floor," he continued working himself up, "Trying to make me doubt it was you."

"I wanted you to be certain." I said.

"Oh, I'm certain." He stated, unequivocally.

"I just needed to see if you still knew your place when there wasn't a forest hiding you."

I held his stare while I repositioned, and replied, with my poshest accent. "And do I?"

His smile sharpened.

"You're on your knees in a locked office, still dressed like a fantasy."

He gestured once, lazy dominance in the motion. "You tell me."

I didn't answer.

He laughed quietly. "Exactly. You don't need to speak."

He stepped closer, and reached down to hold my ponytail. Not grabbing, not pulling.

"You like being quiet," he said.

"I don't need permission to speak," I answered.

"You don't need permission to obey," he corrected. "That's why you didn't flinch when I said your name at the desk."

I swallowed, "I chose not to."

"And you choose to kneel." His voice dropped. "Convenient."

I opened my mouth ready, paused, then closed it again.

"There she is," he murmured. "The slut who wants to be told."

He pulled my back hair to make me meet his eyes.

"Open it again."

He reached down to his trousers and undid his zip. I noticed that his jeans were speckled with something, likely paint. He was probably a tradesman in his real life. A small clue to redress the balance of lost anonymity.

But I knew what to do, and I reacquainted myself with his erect penis. It had not been a day and he was back for more oral sex.

As you know, I was no stranger to sucking cock in this office, both the manager Alex and the area manager Charles had me blow them here previously.

But this wasn't about pleasing him. Not really. Not like it was with Alex or Charles before, in the office when I had no choice but to perform under their eyes.

Here, it was different. It was my choice, or at least, I told myself it was. I had him follow me upstairs. I had knelt. I had opened my mouth. All of it was deliberate, and yet it was surrender at the same time.

And I liked that. I liked the way his cock made my pulse pound in my throat and ears. I liked the way my body responded without consulting my brain, the way my sore lips remembered exactly what to do. There was defiance, in letting him find me again, in choosing to be claimed. There was rebellion in following commands that I could resist but chose not to. And there was the submission that twisted itself into satisfaction, the same satisfaction I had learned to chase in this office.

But unlike before, this was a stranger. I had no employee contract, no rules, no script except my own instinct to obey.

"Down," he demanded. "Don't look at me unless I tell you."

I lowered my eyes feeling the thrill of submission tighten in my chest.

"Faster," he murmured, voice clipped. "Don't think. Move."

I did.

I felt the rhythm settle into muscle memory, the same motions I'd learned long ago as a teenager, now sharper with experience, more precise under his scrutiny.

"Good," he said after a minute of head, "Keep your tongue there. Don't slow for air."

"Yes," I whispered, a reflexive confirmation.

He tapped my head lightly. "Not like that. You're too eager. Obey, not guess."

I froze, then adjusted, letting instinct override thought.

"You like being told what to do, don't you?" he asked quietly.

I swallowed, words caught in my throat. "Yes," I admitted, my voice small but firm.

"Say it," he insisted.

"I like being told what to do," I struggled, finding that he liked to watch me attempt to speak with his cock in my mouth.

"That's better," he said. "Much better. Don't move away. Don't pull. I'll fuck your mouth, and you hold your breath until I say."

I obeyed, feeling the heat of adrenaline mix with something... a thrill I couldn't name.

"Good girl, now breathe." he said. "Eyes down. Hands still. Follow my pace. Not yours."

"Yes." I whispered again, a mantra I could repeat for days.

He paused slightly, gripping my hair tighter, and small, bitter tasting droplets of pre-cum oozed from his cockhead.

He must have felt it too, "Taste it, bitch."

I obeyed, letting the liquid run across my tongue, internalising every command as it passed.

He stepped back, watching me catch my breath, his hands on his hips.

"Up," he said.

I obeyed, rising slowly, aware of every curve pressed into the tight black pleather, the sweaty gloss of my knee-high boots catching the office lights.

"Turn." he commanded, voice low and deliberate.

I twisted, letting him guide the movement with a tilt of his head. My hands pressed lightly to the desk to steady myself, heels clicking softly on the office floor.

"Lean over," he said, pointing to the edge of the desk.

I moved, the texture of the dress stretching across my hips as it rode up, reminding me of last night. My stockings brushed over the polished wood as I positioned myself exactly where he wanted.

"Good girl," he murmured, approvingly. "Keep still. Don't move unless I say."

Obedience. This is what I want. This is what I've been waiting for.

"You remember last night?" he asked.

"Yes," I whispered, voice tight, pulse fluttering in my chest.

I had remembered everything, and already began to write it down in my journal.

"Same rules apply," he said. "You follow. You don't need to think."

I nodded, feeling the thrill of surrender once more.

"Hands on the desk," he instructed. "Legs slightly apart. Keep your back straight."

I adjusted, knees pressing into the wood, boots planted firmly, dress riding up my thighs. My body was ready for his direction.

"Eyes down," he said, voice commanding now. "Let me get you where I want you."

I obeyed, letting his hands guide me where he wanted, tilting, adjusting, him feeling every inch of pleather and stockinged legs as a tool of control.

"Perfect," he murmured. "Don't flinch, just take it."

I'm ready. In the moment I'm his.

"Hands flat," he said. "Head lower. I want to see your neck, not your eyes."

Then, almost casually, as if adding punctuation:

He spat once, landing in the middle of my back.

"Don't react," he said instantly, as I felt his cock-head absorbing his saliva from the plastic dress.

He pulled my g-string panties to one side as he entered my 'pussy' once more. Although he was big, I found that my well-used hole took it all, easier than before.

"Just follow my rhythm," he murmured.

"Yes," I whispered.

"Hands on the desk. Chin down. Look forward," he ordered.

I obeyed immediately, as I had strayed.

"Good girl," he said, a split second longer this time.

"You're learning."

I shivered slightly at the precision of it, the clarity of instruction.

I liked that I was being guided. Something that David could never do. I like that I don't need to decide. I trusted a stranger to know what to do with me more than my boyfriend of 2 years.

"Eyes down," he repeated, as my back had started to arch upwards from his deep anal penetration.

"Take it like a slut. And don't move unless I tell you to adjust."

"Yes," I breathed, letting instinct take over.

He paused briefly, watching.

"You feel that?" he asked, twitching his cock inside me.

"Yes," I admitted. "I can feel you."

His words... did something to me I didn't expect.

I used to think obedience was silent, a quiet submission that existed only in body and spirit. But hearing him give commands, correcting my hips, my hands, my posture... it made me come alive.

Every "good girl," every clipped instruction, every grunt that corrected my movement, it's a rhythm, a conversation I never knew I wanted to have during sex.

I found myself anticipating his next word, yearning for the certainty in his voice, the tiny corrections that he owns this moment as much as I am surrendering to it.

I like it. I'm not just obeying, I'm listening, learning, participating in this dialogue, and it's dangerously compelling.

All this time I didn't know sex could feel like a conversation, but it can. And I wanted more.

Another half-step back, voice sharp. "Wider stance. Legs firm. Don't collapse into me. You hold yourself. I hold you."

"Yes," I repeated, desperate to add "Sir." to my responses.

I am ready for him now. I am here in the moment. I am exactly where I am supposed to be for men...

"Look forward," he said. "No noise."

I exhaled slowly, tensing muscles in my arse to match the instruction, heels off the ground, back taut, dress clinging like armor.

This is what I've been missing for decades, four decades, to be directed and claimed.

"Good. Hold that. I want you still. I want you ready for it."

"Yes Sir." I whispered.

I am ready. I am still. I am his.

He paused, just behind me, hands gripping tightly on my hips as his balls slapped against my skin.

I can feel the tension, the inevitability. I know what comes next.

"I want to finish on you," he said, voice low but deliberate.

"Yes Sir." I acknowledged, getting used to using both words.

This is what he wants. This is what I want to give him.

"Hands where I can see them. Keep your fucking tits on the desk," he continued. "I'm going to cum on you."

I obeyed instantly, heels pressing into the floor again, thighs tight, dress stretched, hands flat on my bosses' desk.

"I'll tell you when," he added, almost casually. "Until then, you stay right there."

"Please." I begged.

He exhaled, slow, deliberate, and leaned just enough that his voice was a low vibration against my ear.

"I want it on you."

"Yes, Cum on me!" I breathed again, chest forward.

A pause. Then:

"Now."

I felt the heat first, a sudden weight pressing against the curve of my back. My pleather dress became slick immediately, the cum load marking me. My body stiffened instinctively, then relaxed, surrendering fully.

"Good," he acknowledged, voice low and satisfied. "It's yours."

I exhaled audibly, trembling slightly under the intensity.

I am marked. I am claimed. I am still standing, still obedient.

Then, a brief pause, a shift in his approach.

"Turn around." He said, "Look at me."

I lifted my head and turned just enough. I knew what was coming.

A quick, deliberate spit landed on my forehead. I flinched just slightly, then steadied myself.

I felt the spit slide down my face, wet and warm, tracing a path over the frame of my spectacles. It rolled slowly across the bridge of my nose, catching on the mascara that had clung stubbornly to my lashes, weighing them down.

"Good girl," he said for a final time, "keep it there."

He stepped back, breathing measured again, watching me take in every sensation.

"You stay just like that," he said.

I remembered HIS words, repeated from last night.

"We are going to walk you back to your desk."

"Yes," I whispered, but startled.

Every warmth, every slick trace, every command. I am carrying it.

He didn't touch me again, but he didn't need to. His presence filled the office like a hand at my spine, steering me without contact.

The clock in the corridor glowed faintly through the blinds as he opened them just enough to check the world outside was still ordinary. Then he looked back at me, slow and satisfied.

"Five‑fifty," he said. "Ten minutes. Perfect."

I knew what that meant before he clarified.

"I want to watch you walk back," he added. "No rushing. Same way you walked through the store earlier."

My breath quivered, "You want to come with me?"

He smirked. "I want the view, Emma. Not the conversation."

I nodded, throat dry, a pulse back loud in my ears.

He stepped to the side of the door...

The moment I turned the handle, a new anxiety surfaced, but it felt different to the woods. That fear had been about being unknown. This one was about being recognised.

His cum had soaked the curve of my back, stark and white against the dark material. Visible, impossible to ignore. The spit on my forehead dripped into my mascara‑coated lashes, sliding down over the bridge of my nose. Sticky and undeniable.

I am seen. I am marked. I am owned.

My boots clicked against the empty corridor first then louder as I reached the hard store flooring. Metal‑tipped kitten heels were quieter than stilettos, but not quiet enough to hide intention. Each step sounded like punctuation, like I was typing my presence back into the building, the smear on my back glaringly obvious to anyone who cared to look.

My mind raced, but my legs didn't. They moved measured, one foot placed carefully in front of the other, calves taut under dark stockings, posture held as well as possible.

I caught my reflection, hair high‑ponied, lips neutral again under makeup, face outwardly intact, yet streaked with the shiny residue of spit. The bright smear across the pleather of my back mocked me in the reflection.

I could almost feel him grading the performance behind me like a secret customer-satisfaction survey.

You've done worse for less, I reminded myself. But i'd never carried evidence so publicly before.

A late customer drifted past with an armful of discounted champagne flutes. Their gaze flicked at me for a split second, confusion and curiosity crossing the line between interest and suspicion. The stark white streak on my black dress caught the overhead light. I felt their unspoken awareness like electricity at the back of my neck.

Good, I thought, pulse tightening. Let them see just enough to wonder. Let them guess.

Behind me, his voice carried, quiet but cutting through the short distance:

"You can still walk?"

I didn't turn around.

I didn't need to.

"Apparently," I said back, barely above a breath.

He laughed once, approving the economy of it. "Good girl."

By the time I reached the glassware desk, my pulse had slowed into something steadier, resolve mixed with aftershock.

I placed my palms flat on the counter, just like I had on the desk, but now the gesture was different.

A public one. The warmth and stickiness on my back pressed me upright, impossible to hide. The spit still drying on my face, the cum stark against pleather. Visible, undeniable, and made every movement a performance.

I turned my head a fraction, not enough to be obvious, just enough for him to see I knew he was there.

He leaned against the escalator railing in the distance, one eyebrow raised.

Five minutes until close, I thought.

Five minutes to carry it, clean it, or hide it.

Five minutes to be someone who can be found and outed.

The store tannoy chimed a polite closing warning.

He mouthed, silently, across the distance as he left, " S L U T."

I moved down the aisle toward the glassware section. Every step in my kitten heels echoed attention, a popping and scraping percussion to the quiet store.

A man appeared at the corner of the aisle, tall, mid‑fifties, in a dark jacket and dark jeans. He now held a tray of champagne glasses, and for a moment our eyes met. His gaze flicked to my back.

I felt it.

Only for a microsecond, but the shiver running up my spine was undeniable.