Emma’s Stiletto Seduction Pt. 32

Trans Emma's double anal cleanup.

This is a continuing story, my journal, please see : Emma's stiletto seduction 01 to Pt. 31 for prior entries.

(you can read this chapter as a standalone work)

Comments welcome.

/

I looked down at my phone, the time said 5.53pm.

That would only give me seven minutes to tidy myself up, to go downstairs and meet the man who was no doubt waiting for me outside.

In my previous life I had often tried making the time period between arranging a date and meeting a man as short as possible.

It was the tremendous guilt that I used to carry with me.

Let me explain.

As a closeted transwoman, the guilt was constantly with me. I'd have to dress in secret, work in secret, live my life in secret and have sex in secret.

Every part of society seemed to amplify that what I was feeling was wrong. That I was an outlier, someone who needed counselling for an illness.

Normal people did not look or act like this. But I felt normal, I wanted to look like I did, and I wanted to do the things that I did.

The same could be true of the men I was meeting. They absolutely fancied women, and they were more than happy to fancy me and be with me.

Most of the time the fact I was trans didn't affect them or our sex life. It was very rare that they wanted to specifically date a transwoman and not a woman.

It didn't take me long to work out that I wasn't attracted to other transwomen, although I would get a lot of attention from them. I look at them as women, and I wanted men.

Anyway, I loved being with a man. I always had, since fantasising about it from a young age, to physically having sex when it was ok for me to do so.

But what I didn't like was the wait.

From arranging to meet a man online, to the time we met was full of excitement, yes, but also guilt. That seed of a colonel of an idea that what I was doing was wrong. That what we were about to do as two consenting adults was wrong.

Many times, especially the first few months, I would cancel a meeting having arranged one. The guilt would consume me.

Through trial and error I found that the less time between arranging and then doing, the less time I had to worry. And the less time I had to worry, the less likely I would cancel.

I have never not turned up for a meet, even if it didn't always go according to plan. If I said I'd be there, I was. 100%.

And still 100%

To help me enjoy myself and reduce the worry, for I always usually enjoyed myself in a meet, I tried to meet a person as soon as possible.

From an exchange of messages to "are you free in 30 minutes?," that was the best.

It also worked better if I had met them before. A lot better. They knew what I was, where I was, and what I liked. They would also know that if they were in the area and passing, and I was available, that they could be having sex with me within a few minutes.

I think my record for one evening was three separate callers. All safe, all fun.

Today reminded me of those very fun times, the "oh crap he will knock on my door in ten minutes" days.

/

I quickly gathered my things from the counter in the restroom and put them into my handbag. This time I would get to keep my keys and 'phone.

One last look back in the mirror and I was still presentable. My black hair had been wetted and brushed back into its natural sleek shoulder length bob. I pulled up the spaghetti straps of my black satin camisole top, and heard the rattle of my name badge, its safety pin still straining against the lightweight material.

Aside from being somewhat hotter than normal, to an outsider they would see a regular woman. A woman in black stiletto shoes and a leather skirt yes, but nothing else openly untoward.

Only one other person knew or could know the secret I was keeping within me.

That my boss had just deposited a cum load inside of me.

Now, ordinarily, this would not be a problem. But you can now see my immediate dilemma.

And I made the wrong choice.

Yes, I could see that now. But when I write this I'm not there, in the moment. In the moment I make bad decisions.

And whilst walking down the far stairs, and striding quickly to the side entrance of the store to meet my 'work boyfriend', it was too late to change things.

/

Just like last week, his delivery lorry was parked in the same place.

I half expected a crowd of staff to have waited until 6pm to cheer me on, or most likely stare and make rude comments. But, for now at least, it seems that I was not of that much interest after all.

Without pause this time, I made my way across the road and reached up to the passenger door. It has to open before the steps up to the cab are revealed. I had only negotiated this twice before but even so, I was pleased at how adept I had become, stepping up in my stiletto high heels.

The driver was there waiting for me, just as before.

He was an older white male, 63 years of age, a shade under 6 foot tall and some may comment nearly the same around their waist. But that would be most uncharitable. He was overweight, yes, but you shouldn't judge a fuck by its cover.

This meeting had actually been arranged for me. Apparently I needed to 'date' someone at the company, to prevent tongues wagging about what had secretly just happened to me...

My boss Charles Heaton had fucked me. Hard. But he wanted it to remain our secret. I was his "dirty little secret."

"Evening Emma," was the drivers' opening gambit, "How was your day?"

I told him when we met last week that I was looking for something casual. Someone to have fun with once a week maybe.

After contemplating his answer for less than 60 seconds, he decided to just go with it.

His words "I'm hardly likely to say no," were still ringing in my ears.

And he hadn't said no.

After a bit of awkward fumbling last week we had soon been kissing. And then soon exploring. Which ended with me edging him with my mouth until he came.

"It's been an interesting week let's say." I replied, turning the passenger seat round and this time not waiting to be asked to sit down. I figured we were long since past this level of politeness.

"Same." He added quickly, "I wasn't going to tell anyone...."

And I believed him.

"I thought you wouldn't want me to." He confirmed.

But he didn't know that wasn't the plan. My bosses Charles and Alex needed people to know, insisted everyone knew what happened in the lorry last week.

And they did so, by showing the cctv footage of me climbing and out of the cab.

"I was caught on a security camera." I explained.

"Yes," He nodded, "Pete told me."

"It is what it is." I said, reluctantly.

And this was true. I didn't want to embarrass him or drag him into the games of others. And yet here we were, again, about to go through the same cycle.

"You can tell me to go." I offered, hoping that he couldn't say yes. There would be consequences for me if he did...

"No," He replied, "I'm too old to let it bother me if you are still ok."

And I was still ok.

He was still sitting in the drivers seat when I walked over and got back on my knees in-front of him. A position we had enjoyed just five evenings ago.

He tilted his head down towards me and kissed me.

Immediately I could tell he was more prepared than I was. I could taste the fresh mint on his lips and the clean linen of his shirt.

He was never planning to say 'no' after all.

The driver was a good kisser, it was the kissing that endeared me to him on our previous meet.

Alex had only kissed me, as an excuse to see if I was willing to go the extra mile with him.

And Charles... Charles had made me blow him, and had literally just fucked me, but was still yet to kiss me.

The driver had remembered exactly how I liked to kiss, to let our lips meet and tongues explore each other. And not to force his tongue immediately into my mouth, but to slowly let me take it. To savour it, to enjoy it. Which I was now doing, sucking his tongue into my mouth with my cherry red lips.

Even though the tongue piercing that my boyfriend David had gifted me as a present when we first got together was mainly used for oral sex, it definitely aided in french kissing too. A new object for the driver to find and play with, with his own tongue.

I placed my hands on his knees, as he held my head softly in his own. He liked to lick my lips with his tongue, as I enjoyed tracing the outline of his own with mine.

Kisses are nice, but they are a side dish to one of the main courses. And it wasn't long before I was untying his belt and encouraging his trousers to be removed.

As he lifted himself off his seat, I quickly pulled his trousers from him, the heavy material falling around his knees and then ankles.

"You will not be needing these." I said, encouragingly, as I slipped his shoes from his feet.

He had a good cock, of average length and girth that I'd had the opportunity to suck previously. It was around six inches, and still had its foreskin. I took the elastic wait of his pants down and his cock sprang out in-front of me.

Kissing had got him nice and hard, ready for me.

"Do you want me to suck it for you?" I asked, again channeling my poshest cut-glass accent, straight out of trans finishing-school.

"Suck it, Emma." He said, with a glint in his eye, placing special emphasis on my name.

And I held his balls tightly in my hand, making the shaft point vertically to the roof of the cab.

"Well you did say you would be my 'dirty slut' tonight in our messages."

He remembered, recalling something that Alex had texted him on my behalf when arranging this meet for me.

I traced the stud in my tongue piercing from his balls to the tip of his cock, trying to retain eye contact as I did so.

"Yes, I did say I would be your slut tonight." I confirmed, before taking his whole length deep inside my mouth.

Last week I edged him to the point of orgasm and then relaxed, repeating the process over and over until he came into my mouth.

Tonight I wanted it to be different, this time I was going to go down hard on him, ramming his cockhead into the back of my throat.

Working up a good amount of saliva, I did so, and it wasn't long before his hands found my hair and he took a clump in each, wrapping it around his fists.

His orgasm control was good, and I could tell that he was trying his best to conserve his pleasure. Moving my head hard down on him when he wanted that stimulus, and knowing when to allow me up to breathe - just before he would have cum....

We were good at this, actually, we had quickly become great at this.

He was happy for me to be a cock slut for him, and he seemed more than happy for me to be greedily enjoying his dick.

And I was seriously enjoying it, and I certainly would have been happy to continue.

But tonight, he wanted to have more...

He stood up front the drivers seat with me still attached to him, not letting him go. I had to rock back on my heels as he pulled the curtains across the glass, secluding us from the night that was about to fall upon us.

He reversed back through the two seats and into the sleeping area of the cab, I followed, crawling in my knees and trying to stop his cock from leaving my mouth.

He sat on the edge of the bed and let me work on him some more, until he grabbed my hair again and pulled me up and off of him.

He positioned himself lying back on the bed, perpendicular to the lorry.

He was a large man, and I dont think I would have been able to straddle him in this position - and there wasn't enough room for me to really lower myself down onto him....

He held his cock hard and upright, and asked me to get on top of him.

I hitched up my leather skirt and pulled it up to my waist.

Kneeling on the edge of the bed at first, I turned to face away from him, and got across his legs. He pulled my bottom towards him and we kind of met in the middle.... With his cockhead resting on my anus.

I wasn't too familiar with reverse cowgirl but if anything was that, this was going to be it.

His cock was wet from the saliva I had produced when throating him and, combined with the hard anal sex I had just had earlier, he easily slipped straight into my bottom.

It was an unusual position, but comfortable.

I'd never been taken like this before, but here I was. The first thing I noticed, unlike when Charles had fucked me doggy-style earlier, is that I would have to do all of the work.

I was used to doing 100% of the oral sex, that was my role. But I'd always previously regarded anal sex as the domain of the man. To let him show me who is boss. To let him fuck me.

Yes, I'd sometimes push back against a cock, and learned to tighten and loosen my asshole to grip him, but this was going to be different.

I started to get used to the feeling, it was easy to just start to rock.... That motion would move his cock 2 inches in and out of me. This I could do.

To take his full length in and out of me would be more difficult, it would require agility and most of all strength that I didn't know I had. My hamstrings were burning just doing a minute of this.

I made a mental note that this was a much better workout than any time I had ever been to a gym.

I'd like to tell you we were in tune, like we had perfected oral sex earlier, but this was not at all true. It was more of a work in progress, a "to be continued." But I was certainly starting to enjoy it, even if I did have to concentrate hard on keeping his cock inside me.

I didn't want him to be one of those men who would announce that he was about to cum, even though I knew he was going to.

My arse had taken him past the point of no return, and with a few more gentle rocks back against him, I sat upright and arched my back as he emptied his full load inside me.

I knew that when I had to remove his cock from me, a rush of another mans cum, his own cum and some lube will be running down all over his penis.

I guess when he knew I would be a "filthy slut" for him tonight, he had no idea just how much he was getting.

And I knew of only one way to clean him up...

And it was only Monday.