Emma's Stiletto Seduction

Trans Emma has to suck a delivery driver.

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

Emma's stiletto seduction 01 to Pt. 28 for prior entries.

Direction, suggestions, comments welcome.

/

During the first few weeks of my new employment, it was fair to say that my two bosses had taken advantage of our arrangement. They knew from the off that I really wanted to get the job, and had figured out how far I was willing to go to keep them on side.

But in the first week especially, their willingness to use me, sexually, had attracted too much attention. Certainly there was some information radiating from the shop floor that would become embarrassing to them if it was found to be more than just rumour and office gossip.

Their plan to curb the speculation was as ridiculous as it was simple. To remove attention from their arrangement with me, I would need to find a "work boyfriend", in addition to the one I actually had in my private life. The love of my life, David.

David had been called away for work, one of the reasons that I now found myself in this situation. But It wasn't his fault. I knew what I was getting into when I signed on the dotted line here at the company. Everything else after that is all down to me and me alone.

My office manager Alex, although he knew that he could now call on me to orally service him, was still jealous of the male attention I would get from drivers, store workers and the occasional customer. It didn't help that he would always insist I turned up to work in "business dress", which seemed to be a shorthand code for tight skirts, stockings and high heels.

The area manager, Charles, also had a thing for women in leather too. Which compounded the attention I received when he was demanding of my services and that I should dress to his liking.

Initially, they were both rather coy when they wanted me. But with that said, the first few weeks had them being quite indiscreet, certainly, but their attitude towards me was now much more official, even stern.

It had gone from 'will you do it' to 'you will do it.' Their expectation of me had changed along with their use of language.

"You are going to get a work boyfriend," Said Charles, "Nothing important or going anywhere, just someone we can say you are with."

"So we can keep things that happen between us private." Alex added, "You know how it is."

Of course I knew exactly how it is.

I have had to be discreet in liaisons for most of my life, right until I came out as a transwoman and met my actual real life partner. Up to that period things were kept behind closed doors or in secluded areas. Meeting me was a dirty little secret for men, something that I was happy to go along with back then.

But it was my bosses that had been less than discreet. Parading me through the store, asking me to dress up inappropriately for them in work, and often seen disappearing with me for 30 or 40 minutes.

That was on them, not me.

And worse, they knew it. Greed, impatience, ego - all helped them to have to take steps to make quiet the office grape vine.

"If she had a boyfriend", they mused, "someone the other staff could see and relate to", it would provide cover for them. 'Running pass interference' was a phrase I think they once used, but I didn't quite understand what they meant with that reference at the time.

"Anyway," Alex explained taking me aback, "I've chosen someone for you."

I nodded.

"Just a delivery driver, no one special." Alex informed me, seemingly going through a list on his notepad. "He doesn't have a girlfriend, lives away, and he drops off here once or twice a week."

Which would be perfect for their plan. A person known to most if not all shop workers, but who isn't really around that much for them to see us interacting together.

I looked up at Alex, my movement attracting his attention.

"Any questions, Emma?" he asked, casually.

"Err how old is he?" I replied, "What is he like, will he like me?"

Alex looked bemused. "Are there any answers that I can give you that would stop this happening?"

I shook my head.

"Ive seen the way they look at you, you fucking slut, so I'm going to make it happen for you."

This was the first time Alex had called me a 'slut' to my face. The first time anyone here had. Even when I had been with them sexually, or they had been discussing me together in their 'boys club', they had not called me by such words.

"Are you busy tonight?" He asked.

I didn't get the chance to respond.

"You are now if you want to work here." He instructed, "Give me your phone."

I took my phone out of my shoulder bag and unlocked it. Alex immediately took it from me.

"I'm going to put his number into your phone if thats ok." He asked, not wanting or needing a reply. "It will be under 'Work Boyfriend in your contacts."

I nodded once more.

"I'm also going to invite you to my work group chat, the one I have with Charles"

"Yes sir."

"Anyway, come and take it back from me at the end of work today." He informed me, "And tidy yourself up a bit."

Ordinarily I wouldn't give my phone out like this, but he didn't I keep a second phone. Not a 'dirty phone', but one that I can afford to lose.

It was a tip an old friend once gave to me when starting out meeting strangers online for sex. "Leave a note somewhere, anywhere, telling people where you are going." and "Don't take anything with you that you wouldn't want to lose."

On my primary phone I had texted David in New York that I would be working late, so not to worry if I don't message him until tomorrow.

I don't know how I felt, starting to lie to him. I justified it by trying to convince myself that it was "work", or that he understood my need for more...

I knew I was risking things, getting ever deeper. But I just, I just couldn't help myself.

The store closed today at 5pm, and the staff are usually gone by five-thirty bar a skeleton crew assisting with the last delivery to the warehouse.

It was 6pm when Alex handed my spare phone back to me, "He is already outside waiting, probably".

I took my phone and read my messages, Alex watched in the background for my reaction.

Text

Emma: Hi, it's Emma from work, how are you? X

Driver: Sorry?

Emma: I work at the south store, we met last week. X

Driver: did we? Cant remember, whats up?

Emma: Sorry, I got your number from Pete, hope that is ok with you?x

Driver: Oh Pete. I'm seeing him later. Anything wrong?

Emma: No, its not about work, just wanted to say hello x

Driver: ok, which one are you then, the new one?

Emma: Yeah, thats me - I hope I made a good impression? X

Driver: Who is this? Are you having me on?

Emma: haha no, it is me! X

Driver: Prove it!

Emma: Let me send a selfie x

Driver: Yeah right.

<57648KFS.jpg sent>

Driver: wow, wasnt expecting that.

Emma: You ok with me?

Driver: Oh yes. X

Emma: What time do you finish tonight? X

Driver: You serious? X

Driver: I'm here at 5, then unloading and I have to stay till the morning as im down from Doncaster today. Can't drive back for 9 hours X

Emma: Stay? X

Driver: yeah, im in the cab tonight and then off early morning. X

Emma: Need some company? X

Driver: Are you sure? X

Emma: Of course i'm sure x

Emma: I'll be out after closing. X

"I'll lock up and set the alarms." Alex said, "Be back in the morning."

We both exited by the side entrance, next to the fenced in yard where deliveries were made and lorries could reverse in and turn.

The gates to the main yard were now locked, but outside the area on the small entry road was a lorry tractor, the engine part without the trailer attached. I'm still not sure what you call them. It was white, with a cab situated behind the driver and passenger seats.

Contrary to popular opinion, I have never been in one before.

"Oh Emma, before you go." said Alex, quietly turning to me, "I'll need your phone back and your keys."

/

It was still twilight in April at this time, with a low sun reflecting off the large windscreen of the vehicle. It wasn't until you are up close with them that you realise just how large they are.

I could tell there was a person in there, sitting behind the glass in the drivers side. As I approached from the passenger side, I tried to see if I could remember the face of the person it was. I didn't even have his name.

My steel tipped stiletto heels on my boots popped and scraped across the tarmac, but thankfully at this time there was no other people here to attract their attention. The only other car here was my own, and Alex had my keys.

I stood at the vehicles door, not quite knowing what was about to happen or how it was going to happen... I could feel my heart beating through my chest. I remembered that before I was with my boyfriend David, I used to live for these moments. These impossible situations I used to find myself in. And, although David and I had fun with others at times, with this one I was on my own.

Something I had not done for years.

It felt like old times.

I shook my head to compose myself, and smoothed down the black pvc fabric of my knee length fake-leather skirt. I wanted to make the right impression on him, whoever he was.

I heard the passenger door click, and it came open by 2 inches. I realised that I would have to open the door first, and heaved it ajar. The floor of the vehicle for me was at head height, this was certainly going to be interesting.

The driver helped me open the door, and smiled.

"I never actually thought it was you." he said, peering down at me.

I did my best to smile back up at him.

"Err put one foot there", he said, gesticulating with his hand towards a hole in the lorry body, "and the next one there."

But it was no use, until he took my right hand and effectively lifted me up into the vehicle.

It was larger and more spacious than I had imagined from the outside. There was space to walk, or rather shuffle between the dashboard and seats, and a person as small as myself could stand up - even in heels.

Between the seats was a gap which led to the rear of the cab, and I could see that it contained a seating area that looked quite like a day bed we sold in store.

Even though the vehicle on the outside was pristine white, the same couldn't be said about the interior. It was clearly a work vehicle and had the air of someone occasionally living in it, and all that entails. It also had the impression of quickly tidying 'round, but not exactly cleaning.

I kept standing, slightly stooping with my hair brushing against the roof fabric, and looked across at the driver.

He looked back at me, somewhat bemused.

"Hello," I said, trying to break the silence, "I'm Emma."

He glanced across at the name badge on my chest, "Yes, so you are."

Looking back at me was the unknown driver, and you could sense that he was a professional driver for a living.

It was hard to tell how tall he was, but I imagined about 5ft10 or 11, and was around 15 to 20 years older than me. The sedentary lifestyle had been hard on him. He was carrying a lot more weight than he should, and just about fitted between the drivers seat and the wheel.

He was wearing dark cotton trousers and dark trainers. He had on a light coloured shirt, button up but short sleeved which had the name of the company in small lettering on the chest.

He shook his head a little, unsure what to make of the sight before him.

"I didn't think you were real, thought they were pulling my leg." He admitted, glancing quickly through the windows.

"Well no," I replied, in an accent that was posher than was necessary in the circumstances, "as you can see I am quite real."

He nodded.

The driver was also "real", in a different sense. Having spent two weeks with only Alex and Charles for company, it was ironically a breath of fresh air to speak with someone who clearly did not communicate in riddles, or in double-entendres. A person that wasn't playing a power game over me.

"Can I sit down?" I asked. And I did so without waiting for a response.

The passenger seat rotated into the cabs centre, as did the drivers seat, so we were now facing each other. I smoothed down my black plastic skirt and tucked the sides under my legs. I placed my hands to one side, palms down, as I was instructed in my deportment classes.

When I first ventured out as a trans woman, I was still really a cross dresser. I attended meetings of similar people and, much to my initial scorn and bemusement, they held classes on how to 'act' like a woman.

But they taught me to speak quietly, softly, and use a different vocal register. Something that I had perfected 25 years later. They also taught me how to cross my legs, how to walk, how to hold my hands and never to lock fingers. They were all good habits to get into.

And here I was, after all this time, still meeting up with completely random men and using what they taught me.

I looked up at him, in my perfect black leather stiletto knee boots. My perfect black plastic skirt. My perfect black silk blouse. My perfect black bobbed haircut. And make up, yes, done to perfection.

He looked back at me through world-weary eyes and sighed, as if to say, 'do you actually want to be here?'

"Look luv," He said, "I don't know why you are doin' this but I'm not going to say no am I?"

Yes, he was real. And not afraid to said what he meant. That went a long way to humanising him, and, although I didn't know his name, it relaxed me in his company.

"I take it you are single, then?" I asked, "Or you wouldn't have invited me up here."

"Yes," He replied, "I guess I am."

I got the impression that he thought that his days of looking for a partner were long gone.

"How old are you?" I asked.

"Sixty three." He replied, "Is that ok?"

"Yes." I chuckled, "I'm forty-five."

He nodded formally.

"Is that ok?" I asked?

"Yes," He responded, smiling, "that works for me."

"So what are you looking for?" He asked, inquisitively.a question I have been asked a thousand times in hook-up sites before.

"Look," I replied, feeling that I should be open with him, "I'm new here and I don't want to get too involved with anyone, I just want some no strings fun with someone every now and again."

"I can do that." He replied, "I told you, I'm not going to say no if it's offered."

As he said that, he looked at me again, I hoped that after our chat and further clarification of things, he was actually fancying me.

"Well, you want to go through to the back?" He suggested.

"Ok." I replied, and stepped up onto my high heels and through to the rear of the cabin.

The day bed was a narrow, single bed sized ledge. It had an unsprung design, but a firm mattress on top and a duvet that had been tucked in and pulled tight.

There was some cupboards, a built in refrigerator and a large tv set flush to the side wall. It gave the impression of making the absolute most of the space it took up, and also that this was a place where someone was living. It was a personal space.

"You don't mind if I close the curtains do you?" He asked, already drawing them around the windows in the front of the cab. "If you leave them open you can't see out and everyone will be able to see in."

As he did so, he dimmed the lighting a little. I stood next to the edge of the bed, and he walked through filling the space in-front of me. Although the ceiling height was larger now, he still had to stoop a little to fit.

"What happens now?" he asked. "So, shall I just kiss you, Emma?"

It was these moments that I used to live for. The time where, on first meeting, a decision has to be made on if you were going to go through with it. To have sex with a stranger.

I always knew my response.

"Yes, kiss me."

He placed his face next to mine, and our lips met. A peck on the lips at first, as he tasted my lipstick and slowly peeled my lips from his. The waxy lipstick joining them together only for a split second.

He repositioned himself, and this time came in for a longer kiss, having first tilted his head a little, kissing old school 'Hollywood Style'.

I felt his hands steady me around my waist, smoothing down my black satin blouse until they came to rest on my hips. I reached up as best I could to him, and placed my arms around his neck, pulling him closer and increasing the pressure of our kisses.

I closed my eyes and, together, we slowly open our mouths and allowed our tongues to start exploring each other.

He was a surprisingly gentle kisser, and a good one too. Alex and Charles didn't seem to wasn't to kiss properly, like most men, they were only really interested in forcing their tongue into only mouth.

The driver was different, which betrayed his size and rough and ready appearance. He didn't seem the type, but, he definitely was very experienced and seemed to know what he was doing.

As I relaxed into his arms, I started to feel for the first time that I may actually enjoy this rather than endure.

Still locked into his arms and my embrace, I felt him start to reposition us, together, until he was next to the edge of the bed. And when he was, he slowly sat down whilst letting my body slip naturally between his legs.

As he lay back, I fell with him, our tongues were still gently exploring each other. And then further, I felt my breasts start squeezing themselves against his chest when on top of him.

His hands, that were previously gently holding me by the hips found their way down to the taught plastic skirt now stretched across my bottom. It was my best feature, and he had found it. He started squeezing my bum cheeks gently, then held them tightly, as I rested my forearms against his chest. I his head into my hands.

Yes, he was a very good kisser, and I wanted more.

I pulled my head fron his, having to arch my back to do so, and returned for more. I wanted to explore his mouth and lips with the tip of my tongue. And he let me, pulling his own tongue away from me as he did so.

Until it was his turn, holding my head now, and pushing his tongue between my own lips. I began to suck it, slowly at first, and then faster, and deeper. I love sucking a mans' tongue almost as much as sucking his cock. He seemed to enjoy the experience and did not resist me doing it more as it tried to push its way deeper into my mouth.

After he had released me, I softly kissed his lips, and worked my way down to his neck and started to nuzzle it, at the same time letting my hands wander and start to unbutton his shirt.

He was definitely a big man, certainly one of the largest I'd ever been with. His chest was covered in a mix of dark and grey hair, which I started to run my hand through. As I did so he traced a finger up and down my spine, through the soft satin material of my blouse.

Slowly I began to allow myself to slip through his grasp, my head working its way down from the nape of his neck to his chest. Now I could get both of my hands on him, and instinctively they found his nipples nested in his chest hair.

It had been a while since I had been in the company of a man like this, and, to my amazement, I found that I had missed the smell of a working man too.

I nuzzled my face under his arm, and couldn't resist. I don't mind this smell, I prefer it in every-way to a freshly showered and deodorant sprayed body.

I cheekily allowed myself to smell him, really smell him, and wondered what I had waiting for me elsewhere.

I slipped through his arms and onto my knees in front of him, the edge of the bed gave us a perfect height. It was lower than a regular bed.

I looked up at him as I started to unbutton his trousers.

"Is this real enough for you?" I asked.

It was his turn to nod.

I pulled down his pants to let his penis spring loose. He was already erect and hard.