Emma’s Stiletto Seduction Pt. 27

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Trans Emma describes sex with her new boss.

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

Emma’s stiletto seduction 01 to Pt. 26 for prior entries.

Comments welcome.

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I stood there, motionless…

Watching in silence as his hand reached around the back of my head. As he did so, I felt his fingers smooth over my jet-black hair, that had been pulled tight by the grip of an elastic band forming a ponytail.

His hand tightened around it, pulling my hair taught at the roots.

It was not the first time this scenario had happened to me, in fact it was very common. So much so that my mind had enough data to have formed a correlation.

You can always tell what a man is going to be like, the true colour of their heart, by how they hold your hair.

If they run their fingers through it, they are usually gentle and loving. If they grab you by the hair, and use it to steer your head or restrict you, then you know that they are a man who wants control.

Who wants power over you.

I felt him slowly tighten his grip more, if it were possible. He pulled down on my ponytail, forcing my head upwards and to face him directly for the first time.

I didn’t want to be intimidated, no, not by him. Through my thick black mascara and long false lashes, I looked him square in the eyes.

This created a pause.

And then, he did something most unexpected, he lowered his lips to my own…. taking great care and precision NOT to kiss them.

He knew that he couldn’t kiss me. The act of kissing me would leave him open, vulnerable.

He had already gone too far by touching me first, causing his mind to start racing, but he couldn’t find it in himself to let go of my hair.

To simply walk away from the situation.

I had known men like this before. Even though he was standing in front of me, touching me, restraining me…. he was waiting for me.

Although I’m naturally submissive, some men want, no, need me to make the first move.

Slowly I opened my lips, only slightly, just enough to feel my thick red lipstick start to peel apart.

And with the slightest of touches, a millimetre, unmistakably moved my lips to his.

Instantly I felt his hand pull my head towards his, our lips forced together now, until his tongue fought its way between mine.

And then almost in the same movement he pushed me away at the shoulder, turning ısparta escort and wiping his mouth on his sleeve.

“Why did you kiss me?” He asked, somewhat angrily.

“I…”

I knew when to shut up.

“It’s your first day, it’s nine-twenty.” He said, annoyed. “And you are already trying to kiss me.”

I looked down to the floor.

“That’s right,” He said, observing my response, “I could have you sacked for that.”

And he quickly paced across to his desk to sit back in his chair, mind racing, he was thinking quickly now.

My response had been surprising and reassuring to him.

It was the moment he had waited for, with the person he felt he had been looking for his whole life.

His mind was begging him, convincing him that this might be his only opportunity despite the risk ….

“Do you want to kiss me again?” He asked, desperately trying to conquer his nerves, fighting against each syllable that came out of his mouth.

I nodded.

“You will have to tell me.” He explained, “Tell me in words.”

“Yes Sir.” I responded and nodded affirmatively again, “I want to kiss you, Sir.”

I knew this was the cue, what he had been waiting for, for me to at least openly acknowledge that I wanted him.

Now and only now could he tell everyone, and his own conscience, that it was all ‘Emma and her insistance’…

He listened carefully as my high heels clicked and echoed along the hardwood floor of his office.

In these initial moments, knowing what is about to take place…. It feels like I’m not here, like I’m watching myself from a distance. Like it is another person doing these acts and not me.

When I came to my senses, I was stood in front of him, my black stockinged legs positioned in between his legs, as he once more leaned back on the office chair.

I had to bend over to put my lips to his. And there we stayed, transfixed in that position, neither moving until it felt right to let my tongue explore his mouth.

I found his tongue with mine, and then took it between my lips. I slowly started to suck on it.

I know few men could resist this action, screw ‘hawk tuah’, this was my own secret. But why was I the one apparently now seducing this man?

I knew he wanted me, most likely to fuck me. But here I was as the submissive having to take the lead and initiate.

But it didn’t stay that kadirli escort way.

His right hand once again found the back of my head and took my hair, this time even more forcefully than before. His left hand was already trying to clumsily unbuckle the belt of his suit trousers.

He was going to test me, before the ink was dry on the contract. A simple kiss was never going to be enough to pay him back for employing me.

I’d hoped that it would at least take him longer to work up to this. But no. He couldn’t help himself.

He was going to have me here and now, and he wanted to have me before his manager Charles had me.

Alex pulled my mouth away from his, making space between us, revealing that his cock was already out of his trousers. It was fully erect now and just inches from my head.

I allowed my eyes to glance at it, quickly, and then back to his eyes.

“Should I have looked?” I shamefully thought to myself. “Should I be wanting to use it like he was about to use me?”

Either way, it was a decent cock, about 6 inches in length from balls to bell and not too wide. His foreskin was long, but had already been stretched back tightly over the head. It was glistening, wet and leaking precum from the eyeslit in the tip.

I did not think that I was going to perform this sex act. At least not on my first work day, even if at some point it was probably inevitable. If I sucked his cock on the first day then he would likely expect me to blow him every day that I worked here.

But it was too late to change my mind. Impossible to change my mind or even to slow things down now.

“I think you are a cock sucker.” Alex suggested, wanting to judge my reaction to his words.

I resisted his pull slightly, straining back against his tight grip on my hair.

“Don’t deny it.”

I did not deny it. He was absolutely correct. I was definitely a cock sucker. I just didn’t want him to know it.

“You going to get to know this cock very well, Emma.” He said, adding emphasis to my name.

He pulled against me harder now, my hair slowly being released from the taught elastic band of my ponytail whilst in his grip.

His left hand found the base of his penis, and took the erection from his belly and pointed it straight towards me.

“I think your lips are made for this, aren’t they, Emma?”

And he pulled my head kadıköy escort down onto his shaft, pushing its full length through my lips and deep inside my mouth.

I had to fall to my knees, stumbling from my 5 inch stiletto shoes in front of him whilst I tried to steady myself. My hands found the arms of his chair whilst trying to breathe through my nose. Initially he refused to let me come up for air, to gasp a breath.

Thankfully, I knew from experience this wouldn’t last long.

That HE wouldn’t last long.

He grabbed the base of his cock and started to masturbate furiously whilst simultaneously directing the movement of my head using my hair.

When men wank during a blowjob, it is always a sign that they want to cum or are about to cum.

This was no exception.

Unlike most men, however, he didn’t not announce it to the world. But he did take my mouth away from his cock as he started to spray a stream of cum over my lips.

After his third contraction, he pulled my mouth back to the head of his penis and it penetrated my lips once more.

He wanted to see his cock in my mouth with a clearer mind, after the intense throws of his orgasm. To remember it in detail and capture it as a memory.

But he also wanted to remind me, that although he had just came into my mouth, that it wasn’t over. His orgasm was not the end of our arrangement. That it was only the start of the beginning.

“Fuck, I needed that.” He said, breathlessly, as he carelessly wiped the head of his penis over my lips.

I rocked back on my heels, now released from his grasp, first crouching and then and standing in front of him.

His cum had not managed to spray my face, thankfully, but I could feel its wetness around my lips and I had started to taste the sperm he had given me.

Alex pulled himself upright using the arms of his chair. His heart rate still crushing against his chest.

And he took his camera from the desk once more…

/

I watched intently at the screen, to see my boyfriend, David, cum on the 4K video stream in front of me.

The bright white sperm started to flow down across his fingers and hands as he slowed his own solo masturbation.

“You have a fantastic imagination, Emma.” He panted, as the flood of guilt began to wash over him.

David was still old school, and still felt apprehensive about allowing himself to have pleasure. Always one step away from apologising for having an orgasm with me.

“Its my job.” I responded cheekily, starting to feel somewhat embarrassed myself.

But it was not true.

I did not have a fantastic imagination, in fact I didn’t have any imagination at all.

It was all true.

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