Emma's Stiletto Seduction Pt. 07

Emma's Stiletto Seduction Pt. 07

This is a continuing story, please see :

Emma's stiletto seduction

Emma's stiletto seduction Pt. 02

Emma's stiletto seduction Pt. 03

Emma's stiletto seduction Pt. 04

Emma's stiletto seduction Pt. 05

Emma's stiletto seduction Pt. 06

Comments welcome

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I sat there alone at the restaurant table. My brown leather skirt covered in the remains of a sticky dessert, my white silk blouse soaked with the former contents of a glass of red wine.

After two heavy breaths, the realisation of an orgasm flowed into my black panties. They were not able to contain the release of my cum. Slowly the situation and my surroundings came back into my mind...

I sat quietly and placed the palms of my hands on my skirt, wondering how long I would be left like this. Humiliated, vulnerable.

I could hear David at the bar, paying for the meal that we had both enjoyed together. It was our first proper date, and one where our previous sexual friendship had moved on to a relationship. Even though David was still technically married and I am a single trans woman, moments ago we had officially become 'boyfriend and girlfriend'.

We had celebrated this in a rather unconventional way, after all we were an unconventional couple to say the least.

David was an accountant, which says everything you need to know about him. Recently separated from a frosty, sexually redundant overbearing wife, he had found himself involved with someone the complete opposite as a sex partner...Me.

I knew that for David, letting go and just enjoying himself sexually was going to be a difficult task. The older generation was brought up to be gentlemen, to be caring. And worst of all, to 'make love' to women.

In the past, if any of my ex-partners had even thought of using that term, they would be gone. Women, trans-women, don't want to be made love to. No need for flowers, chocolates or that most strange of terms, 'romance'.

They want to have sex.

It's ok to say it, I want a guy to fuck me. In the 25 years I've been using the internet to find men, I never once titled my profile 'looking for love'.

It's always been "trans girl looking for cock(s) to suck". Why beat around the bush. Men should be honest and do the same in their relationships. If you don't ask, you don't get.

I knew that this was difficult for David. All those years of being with the same woman, trapped in a caring but sexless marriage, we're going to affect him. It's probably been so long that he has forgotten what his dreams and fantasies are.

In the last few weeks, since we had been dating, he had come a long way. From getting a blowjob and giving his first anal to his first threesome where he shared me with a stranger. But I feel like these were things that happened to him. He enjoyed them but he was along for the ride as it were, pun intended.

I wanted him to learn to take charge. If he was going to be with me, and our relationship was going to last, it would be a necessary part.

So it seemed perfectly reasonable for me to suggest for our next date he should do as he pleases. Be completely and utterly selfish when it comes to sex. If he couldn't manage this for one day, could there ever be a future?

David had until our arranged date on Saturday to think about things...

I received this note in my work pigeon-hole on Wednesday.

--

To: Emma

Be at my house Saturday morning.

The key will be left in the usual place.

Wake me with your slut mouth at 7am.

--

As I opened the handwritten letter whilst sat at my office desk, my mind started to race. I honestly didn't know how the weekend would work out, but it certainly had me intrigued. Of course at no point did the thought occur not to be at David's house at 7am and wake him up with a blowjob.

Thankfully the nights of no sleep before a meeting with David were long over. I still had butterflies in my stomach when thinking and fantasising but it was more out of excitement to be with him rather than the nerves before a date. As a couple we were passed the phase of 'do they fancy me'.

I had no idea where the day would take me, only knowing how it was going to start. Chosing an outfit to cover all bases and scenarios would be impossible. I had to play it safe, sexy but nevertheless practical.

Underpinning any outfit for a slut like me should be stockings and suspenders. That's rule number 1 that I ran through my mind. There was no question here.

I took out a 34b black basque from the tall chest in my dressing room and hooked the 14 eye-fasteners together around my torso. I rotated it around my body and wrestled the cups up and over my budding breasts. My nipples seemed to be getting larger and more sensitive now. I placed my arms through each strap and adjusted them appropriately, the 4 long suspenders hung loosely by my thighs.

As I sat on the stool in front of my dressing table mirror, I pulled on a pair of black fishnet stockings, the black nail varnish on my painted toenails shined through and matched that of my newly manicured hands. I attached the 4 suspender clasps to the inch-high nylon band that formed each stocking-top.

I stepped into a tiny pair of tight black satin panties that would hopefully do their best to control the appearance of my clit should the occasion arise. It hadn't escaped my attention that on my last date with David I reached orgasm for the first time. In fact for the first time in over 10 years with a man.

As a transvestite I've always liked to play the female role to the full and, when having sex, for me nothing spoiled the fun more that the unwelcome appearance of my 'clit' into the experience. If ever a prospective date had asked to wank or suck my 'clit' as we arranged something then I would either say it's out if the question or more likely a 'thanks but no thanks'. I wanted a man who likes being with trans woman and not someone who only wanted to suck my clit.

I chose a tight black pair of fake leather 'wet look' leggings to complete my outfit. It was daring yes, just wearing a basque on top - especially one where suspender straps would be clearly visible, but the leggings would make it more appropriate and less revealing than my usual mini or micro skirts and dresses. It would also help me feel slimmer and taller, with me at just 5ft4 David usually towered over me.

I chose a pair of black matt leather 4" spiked stiletto heels with a Mary-Jane strap. They had a tiny 1/2" hidden platform and a pointed toe. Practical and sexy.

I completed the look with a 2cm wide plain black leather collar and silver 10cm diameter hooped earrings.

My make-up followed the usual pattern, far too much black liquid eye liner, false lashes but with a pale red lipstick that could almost be confused with a pink. I'd grab a short blouson style button-up leather jacket with two front pockets, on my way out.

If you had to summarise my outfit it would be 'goth' Sandy from the movie Grease, but of course I'd styled my jet black hair in a sleek symmetrical chin-length bob instead of the blonde curls worn by Olivia Newton John. I wondered if David would mention this?

--

The key to David's 1930s detached house was correctly placed in our secret spot. I gathered my thoughts as I watched the cold winter air turn my hot breath into dew. Wearing stockings under plastic leggings had done their job and kept me warm, the sun would not be above the horizon for another hour at least.

At 6.55 am I quietly turned the Yale lock and let myself in to the hallway of the silent house. The metal tips of my high heeled shoes echoed softly in the stillness. It may have been approaching 7am but it could have easily passed as the middle of the night.

I checked my lipstick in the hall mirror and hung my handbag over the hatstand. I peeled off my black leather jacket and placed it over the stair bannister. With a practiced skill I quietly made my way up the carpeted stairs taking care not to trip, my heart beating a little faster now.

The door to the main bedroom was ajar, and I could see David sleeping soundly on his right side. The blue light of the lcd clock pierced the room, 6.58am. I was on time.

I turned the lower corner of the duvet back, and crept under. I could feel the heat radiating against my cold skin from the 6ft 3 man soundly sleeping in his king sized bed. He was naked.

I lay on my left side, facing him, but with my head at his groin. Under the covers the subtle blue light cast in the room was of no use, it was pitch black. My cold face and lips could sense that his body was close now, just an inch away. Without sight to guide me, my other senses felt heightened. I could smell him. Unmistakably David.

His penis was almost 7" long and of an average thickness. He wasn't a stallion or porn star but definitely better than most. If anything, I preferred a thin penis to a thick one like a beer can. David's was perfect for me with a purple bell end and skin so soft that it felt brand new and unused.

But his penis wasn't erect at the moment, it was smaller, around 2 to 3 inches long with foreskin covering the glans. I felt around with my face and in the darkness found the tip of his penis, slightly wet to the touch, brush against my cheek.

I slowly placed my lips to the point in space I believed the tip to be, and found it. I let my lips linger against it for a minute, making sure not to rouse him. I opened my mouth and slowly, naturally worked the flaccid penis inside. Still he did not wake.

I held it there for another minute, until I felt a slight twitch. The penis moved with the slightest beat of his heart. Each heartbeat made the dick swell, almost imperceptible if it were not inside my mouth. The cumulative effect of a hundred heartbeats caused his cock to increase until it was hard. Morning glory, the glans warmly resting against my tongue.

Again I held it there, and happily would have done so whilst we both rested and slept soundly in the warm bed, letting the winter morning melt away.

But this was not in the letter, the words did not read "hold my penis in your mouth whilst we both sleep". It read "wake me with your slut mouth at 7am" and I was sure that it was very much past 7am now.

My hooped earring had folded backwards against the duvet I was under, tugging tightly and stretching my earlobe. I adjusted my position in the bed, I was curled up on my side so that the duvet just covered me at the foot of the bed. I could feel his cock grow harder now, and twitch. Was he now forced by my actions to be dreaming about sex? Either way, my tongue had parted his foreskin and found the eye of his cock. It was definitely leaking a small amount of liquid of unknown origin be it urine or pre-cum.

I worked the cockhead so that the bell was between my lips, the foreskin had not yet been pulled back across it so I had to try and edge it back with my lips and tongue without waking him. With subtle movements of my lips his fire skin went back over his glans and stayed there. In this dark and hidden place I now had his cock at my mercy.

Slowly I bobbed my head down, taking in only another inch at first and then releasing it back to the resting position with just the knob in my mouth. Again down, his cock was responding but he was still not awake.

And then sucking, slowly passing my tongue across the cockhead which I knew he loved.... He murmured and stretched his shoulders.

Now I was sucking his cock, regular movements, deep into my slut mouth, there could be no question that this was arousing him from his sleep. As he came around and woke, my rhythm became stronger and faster and he jerked awake. Hard, erect, breathless.

Neither of us could see each other, a duvet and the dark winter morning prevented this. He couldn't even be one hundred percent sure who owned the mouth that was now enveloping his cock and orally servicing him.

Yes, he was definitely awake now. He rolled on his back and I rolled with him. Lying flat on my belly, my tits pressed hard against my chest and my head bobbing up and down on his shaft. I could feel a hand find the back of my head that served to add encouragement and urgency to the rhythm, but David was not ready to cum just yet.

I rose up onto my elbows, freeing my hands to grasp his penis between the palms. David placing his legs up and over my shoulders onto my back. The weight controlled my body, and his hands my head, pulling me deeper and deeper onto him as he enjoyed himself. Still he could only see the duvet moving on his crotch and my black stiletto heels pointing to the ceiling, as they had now escaped the covers.

But this wasn't supposed to be a normal Saturday. It was one where the goal was for David to be completely selfish, to use me for his own pleasure with no thought to my own. He was enjoying himself, yes, and instead of resisting his primal urge as usual, he was determined to follow what he wanted...

In a movement he threw the covers back revealing the scene in-front of him. His trans girlfriend, Emma, dressed in tight black leather with her head buried deeply on his cock.

Using his arms as leverage, the tables were turned. I was instantly twisted around, now on my back with David on top of me. And yes, his cockhead was now buried deeply in my throat through the force of his bodyweight.

As he leant up on his knees, the glans popped up and out of my throat which allowed me to gasp a breath... but immediately it was pushed back in and held there.

Out, breath, in. Hold.

Out, breath, in. Hold.

All I could think about in this moment was "finally, David from accounts is fucking my throat."

He released his penis from my mouth, letting me breathe free again, and I felt his knees moving up my body, forward of my shoulders until his balls and then perineum were hovering above my lips.

Although his balls had been recently trimmed, his perineum was very hairy and covered with sweat. He gently lowered it onto my face and sat there as my tongue got to work licking and cleaning this sensitive and hidden area.

He loved rubbing the length of his penis down my tongue, past his balls and along the muscular path leading to his hole. He definitely tea-bagged me too, although I was certain he wouldn't know the term used to describe dipping his balls into my mouth.

He was seizing the moment, and taking his fill of me.. He wasn't holding my hand as we had sex, now he was holding my hands down as we had sex. It was a revelation, but would it be a revolution?

Still grasping my hands, he stopped kneeling over me and stood off the bed on the floor. I looked up at him but he wasn't looking back. He stood there, hot, sweating and naked with a proud erection that pointed proudly to the ceiling. He dragged me by the arms, sliding on my back so that my head was over the edge of the bed. The first bed we have ever been in together... his strength moved me easily into this submissive position.

Quickly he wanked his shaft, apparently wanting to make sure it was still hard, but he need not have worried. It was rock hard and very turned on, and he plunged it deep into my mouth again, holding my head down and lips open by pulling my hair.

It reached my throat, but wouldn't pass into my throat this time without his weight persuading it. I tried to swallow several times and relax my throat, my arms reaching to his arse and pulling him on to me to help. But he swatted them away. Holding my head firmly in his hands he thrusted his cock passed my tonsils and opened it up for him to fuck.

Once it had passed deep into my throat he was now free to push its length as far as he wanted, and he did. Balls deep inside me, fucking it hard as if it were a cheap whores cunt. Every time I needed air, he made me thrash about, arms and legs flailing before he would relent and allow me to catch up on oxygen. Spit and mucus streaming from my nose. Relentless.

The sensation of fucking someone's throat was completely new to David. He had only made love to his wife before, and always vaginally with a condom. She had sucked his cock before prior to their marriage, or he thought she had - if brushing her lips against his sheathed shaft counted? It didn't.

The feeling of me sucking his cock on our first meet all those weeks ago had never left him. It had him addicted to me, he could never go back to how it was before, he was determined to enjoy life and a sex life whilst his health would allow.

The position he now found himself in was new. He had seen it crop up on porn movies that he had secretly allowed himself to view after his wife has stopped showing any interest in him. He had liked how the women were at the mercy of a pornstars' cock. Head over the bed, throat straight in alignment allowing passage and a much deeper throating to happen. It was basic physics.

He also liked the gagging sounds the women made, or were forced to make by their partner. But what David had not realised that in this 69 style position, my tongue was now able to lick the majority of his glans instead of underneath it. He found that sensation unbelievably stimulating, and had to concentrate on fucking my skull hard to satiate the need to cum...

And then he stopped, without orgasm. I looked up at him but he still wouldn't meet my eyes. He turned around and crouched slightly on his feet and haunches, presenting his bottom to me. I reached up instinctively and placed my thumbs in his arse crack and pulled them apart. He moved backwards by two inches, and I ran my tongue into his crevasse.

He was warm and drenched with sweat. It tasted salty and manly, if there is such a thing. The tip of my tongue found his hole. It was puckered tightly, so I licked hard around it's rim stimulating his nerve endings and imagination.

He wiped his bottom up and down my face, from cock to arsehole. I greedily ate him up, pushing my tongue into his hole as much as I could and lapping around his rim like a cat laps up milk.

David had never done this before, although he had wanted to he knew that the taboo nature and dirty element would have caused him great anxiety and guilt. But here he was, he had permission to use me for his pleasure, if only for one day.

He grabbed his cock and held it tightly and turned around again to face me. Saliva was covering my face, lipstick had long disappeared and my lips had stared to look swollen. There was more light in the room now, casting a subtle cool glow. David couple see my outfit now, a basque covering my heaving breasts and the blue reflection shining from my tight black leather look leggings.

He pushed me further back on the bed, me sliding easily against the smooth cotton sheet. He crawled on top of me so we were now most definitely in the 69 position. His cockhead found its way back to my mouth, and with a brief push again it passed my tonsils once more and into my throat. It was more open to persuasion now, and I was also more relaxed and welcoming to it.

David soon returned to his rhythmic fucking and seemed to prefer it out and then deep passed through my tonsils, instead of most guys just trying to get it as deep as possible.

I hadn't realised that all of this oral stimulation I was giving to David had turned me on. My clit was full of blood and it's outline was clearly visible through the lightweight plastic material of my black leggings. And David's face was inches away from it.

I couldn't stop and adjust myself to protect my modesty and the inconvenient embarrassment of being a cross dresser, it was also impossible for David not to notice.

I felt him trace the outline of my clit against the tight black plastic of my leggings. Each time he touched me in this way I felt my clit involuntarily twitching and moving. Still he maintained the throat fucking I was taking.

He lowered his face to my clit, and rested them against each other. He could smell the new plastic material and breathed in deeply. He kissed the tip of my clit through the material, and thrusted his cock deeper into my throat. I could now feel him rubbing his tongue up and down the length of my clit. Nervously, he wrapped his hand tightly around it, causing it to lift from being pressed against my skin and to be coated in the thin plastic of my tight leggings.