Emma's Stiletto Seduction Pt. 09

This is a continuing story:

Emma's stiletto seduction 01 to Pt. 08

Comments welcome

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I linked Davids' arm as we walked along the sea front. It was a sunny but cold winters day, and although it was only midday, it had already been full of adventure.

I was in my 4 inch black stiletto heels, but it didn't make much difference. David was much taller than me even when I was wearing them and I had to increase my stride pattern just to keep up with him.

"Thank you for the ice cream." I said, "It will help."

There was a chill in the south westerly sea breeze, and thankfully I had the good sense to wear fishnet stockings under the black plastic imitation leather of my leggings. I didn't however, have the sense to wear anything more than a lace basque to cover my chest. I buttoned up the top of my black leather jacket to try and stay warm and repel the chilled air.

You can imagine that the ice cream wasn't a treat in this weather, it was medicinal. I was starting to feel the pain of my tongue piercing that happened only one hour ago, but licking the cool cream and keeping it on my tongue took the edge off the swelling and soreness.

"I don't know why you didn't have one before, Emma?" David asked. "You out of all people."

We had been together for a few months now, the most unlikely couple you could meet. David was a middle aged gentleman who worked as an accountant and had found himself stuck in a marriage where what little sex and affection shown by his partner had long since ceased. With nothing to keep him and his wife together, the added stresses of lockdowns had taken the cracks in their relationship and torn them apart. She had simply moved out and was staying with family for a few days, but those few days had grown into months and it was quite clear to David that she was never going to return home now. It was over.

Like so many men in their 50s who this happens to, be it through their wife having an affair or simply 'because', it wasn't the absence of a sex partner they lamented, but rather the absence of female company.

I must have found David, or as he would say 'rescued' him at exactly the right time. Lockdown had been good for me, for I had used the time to take the next step in my life and come out as a transwoman. It may not be full time transitioning, but I was no longer hiding it from anyone. Years of it being a secret part of my life were over, and I was sharing it with anyone who expressed an interest.

Just showing pictures of myself transformed into Emma over a workplace coffee seemed to be enough for David, he was not only intrigued by me, but astonished that he could fancy a transwoman. It wasn't that he was against the idea, it just had never occurred to him. It also helped that he liked my style, having fantasised about goth women as a teenager I was 'right up his street' as he liked to say.

And now here he was, proudly walking along the front of Brighton, promenading with a transwoman. A transwoman who had introduced him to the idea that he was desirable. That people wanted to have sex with him, that people enjoyed his company, that people fancied him. But also wanted him for who he is.

Every so often he found himself listening to the popping and scraping of my high heels on the tarmac promenade. How that sound would attract his attention when the office girls in work used to pass him by. But pass by without looking back. Now he has a goth girl in plastic leggings and a black leather jacket clinging to him, warming herself against him. Other men look at his girlfriend with desire, and at him with jealousy. He was still old fashioned though, and thought it no more than "a nice change". But inside, he liked it.

"I don't know what i'm going to tell people in the office." I lamented, "How can I explain suddenly showing up on Monday with a tongue piercing?"

"Just say David from accounts insisted." He said, wryly, knowing full well that wasn't going to happen. He was proud to be walking back into town with me on his arm, but as far as work was concerned I would have to remain his dirty little secret. This suited us both, especially when he called me that when we were having sex.

On the drive home we passed the area that David knew was a local meeting place for "those who wanted to acquire external coitus", as only he could put it. He knew that I had participated in threesomes before, and we had already had a traumatic experience making it happen without controlling for all the factors with a stranger. I didn't want it to put David off the idea though, but we hadn't really talked what happened through.

David knew that I liked sex, he knew that the sex we were having was great. But it bothered him that there was a chance that I was going to do what he feared most. Like most men, he feared that I would leave him. That he wasn't going to be enough for me and unable to keep hold of what we had.

"You needn't worry," I would reassure him, "you are the only man that I've ever fancied." That was true, he was the only man that I'd ever fancied. And it was a dream last summer that changed my own life, I had a dream about him, where we were together, and I had put into place a plan that would hopefully seduce him. It worked. That sounds seedier than it was, he definitely allowed himself to be seduced. And I teased him mercilessly about it ever since.

In the back of his mind he knew that if we were going to stay together he would have to let me experience certain things. Either with or without him. He was only joking about taking me 'dogging', just for fun, but at the back of his mind he also wanted to gauge my reaction to the idea without pressure.

"Do you think you could watch me with other men?" I asked as we passed the turn in to the alleged dogging area and carried on driving by this time...

"I always worry that you would be hurt, or they are rough like Howard was." David replied. "And I worry about my jealousy too."

It was a question that no amount of reassurance would help. What man could not be jealous when watching their partner have sex with another man, or potentially a group of men at the same time.

David knew that this was a part of me, a part of my life. He wanted me, and wanted to continue our relationship more than anything, and if that was going to be the case he would eventually have to comes to terms with things.

"But not for today." He told himself. That was for another time.

"What shall we do when we get home?' He asked, changing the subject. "You are welcome to stay over."

The words had come out of his mouth without thinking, without worry. Although we had been together for weeks now, we had still never stayed over. After having sex, one of us would leave, either from Davids house or my own apartment, and start the next day alone. It was perhaps another step, another step on the relationship ladder that both of us were nervous of taking.

I gargled with a glass of salt water and spat it out into the bathroom sink. It was most unpleasant. The aftercare of a tongue piercing suggested that I did this several times a day. It was as dry as the worst cum I had ever tasted, but if it was going to help the healing process happen faster and reduce infection, it would have to be tolerated.

The jokes of "You have put worse in your mouth!" from David were true, but also wearing thin.

David poured me a glass of 'red' after dinner, but also handed me a glass of iced water. Even though this day had started out as a day where David could have what he wanted, the memories of having our first deep oral sex session this morning were long forgotten. The piercing had changed that. I still didn't understand if it was a show of David trying to take control, or a thoughtful gift for his girlfriend from a boyfriend. I chose not to overthink it too much.

The evening found us sitting together on the sofa, the heat from the log fire and the second glass of wine causing us to curl up, with me sitting in his lap. It didn't seem like we needed the television, or any music, the sound of the wood-stove crackling and the winter rain outside lashing the window was enough.

It was painful to kiss him, but still I tried and he appreciated that. "A blowjob would have been nice," I mused to myself, deliberately letting him hear my whisper.'

"It would have been perfect." He whispered back.

"We could still do other things though?" I suggested.

"Yes," Said David, "but I guess another blowjob can wait after this morning."

It wasn't often that I have heard these words spoken so casually by David. I doubt he had ever used 'blowjob' in a polite conversation before this evening. Perhaps twice ever before, but only when I was actually giving him head at the time.

David relaxed back on the sofa, and I found myself on top of him, face to face and lying in between his legs. Our kisses had to remain mere pecks on the lips, but somehow this was much more intimate that him pushing his tongue into my mouth. We could taste each other, the wine on our lips, and the small distance between our eyes became intense.

I hooked my hands under his arms and onto his shoulders, and pulled him tight to me. Slowly I worked my light kisses down his face and to his neck. He would feel the fluttering of my false eyelashes and the cold silver of my hooped earrings pass his cheek.

He casually placed a finger into my collar and then allowed his hands to explore the skin of my shoulders and down the hook and eye fastenings of my basque. As I nuzzled him, his hands moved from resting on my hips to my bottom. It was only covered with the thin, light plastic material of my leggings and he fondled me, using his large hands to grope me and push our hips together.

I could feel his erection growing, but I was not feeling it on my bottom or stomach this time, I could feel his erection growing by sensing it with my clit.

The realisation that my own clit was growing at the same time as his was a new emotion for me, a new feeling. I never got excited during sex that often, and I certainly hadn't allowed myself to be touched or relieved by another man in many years. It's just 'not my thing' I would tell interested parties on dating apps like fab or tvchix.

The only way I would obtain sexual relief was when I got home from a meet. Going over in my mind the filthy things I had just done with men. That's how I chose to get off ever since I was out of my teens. On most occasions I would wank myself off in-front of a mirror when I got home, staring back at the reflection of a slut displaying a mouthful of another mans cum. I would try and hold it on my tongue throughout the journey home and resist swallowing or spitting.

As I continued to kiss his neck, his cock and my clit became partners, pressed together tightly. Each feeling the others presence through the thin material. It would have been unmistakable, impossible for us both not to notice. I placed one hand around the back of Davids head, and let the other move between us, between our cock and clit. They were now both very hard.

David slowly moved one of his hands from my bottom and found the gossamer gap between our bodies. The palm of his hand rested between us. It was the first time, the first actual time he had clearly felt the hardness and arousal of my clit.

He mind was full of things. He hadn't anticipated this, and the brief flirtations with it of earlier in the morning had been placed at the back of his mind. But here he was, and it was happening again. But this time it seemed more real, more permanent.

He turned his hand upwards, so that now the palm of his hand was against my clit. The flimsy plastic of my cheap leggings being the only barrier between us. He applied pressure at first, and moved the plastic with his hands so that it slowly moved the skin of my clit up and down. I did the same back to him, but my hand was inside his flies now, firmly holding his penis.

I allowed myself to moan as he stimulated me, and I responded to his touch, trying to assure him that it was ok. I undid his belt with my hand, and gently pulled down his pants so that his cock was free. We were almost spooning now, but with enough pressure of my weight for gravity to keep our bodies together.

He didn't know what to do. In his mind he had to make a decision. Was he going to be happy with this, or did he want more? My actions had revealed that it was going to be his choice. I had not moved his hands away but my body responded to their touch.

Slowly, very slowly, he moved his hand to the waistband of my tight black leatherette leggings. He allowed the very tips of his fingers to make their way between the tight elasticated band of the material and the soft skin of my hips.

Inch by inch they explored. Deeper, until the palm of his hand was resting on the bare skin of my 'clit'.

As a trans woman who had not has surgery, I never knew what to refer to my penis as. This is the first time I have ever called it that, and it caused me great pain to write it, to you, the anonymous reader of my most intimate diary.

Past 'lovers', no 'sex partners', had no problem labelling my anus. That was always my 'hole', 'bumhole' and sometimes, 'pussy' or 'girly pussy'. The other bit had always been called my 'clit'. It's sort of the same thing, but just larger than in men than women and is the centre of the orgasm for both. It also helps retain the mystery of having sex with a t-girl for men.

Whatever it was called, for the first time his hand was on my clit. Just resting there, taking in its hardness and softness. The warmth surprised him. He had never touched another before, but it felt different to his own, in the way that its impossible to tickle yourself. This was a very separate, contrasting experience.

I took his cock in my hand, encircling the base of the shaft with my index finger and thumb. He did the same, he was mirroring me.

Slowly I started to wank him, very gently. And he did the same. After a few moments of this I increased the pace, moving up the shaft to the glans and rubbed his foreskin across the ridge with my thumb. He sighed.

I moved from kissing his neck, and worked my way back to his lips. We were now face to face, and slowly masturbating each other.

He reached down and worked my stretched leggings down below my bum. We were now both naked in that area, exposed but out of sight. His penis lay on my clit, we remained motionless and silent. Our two erections laying side by side. His bested my clit, a strong 7" where as mine was just under 6" now, both were reacting with every thunderous heartbeat.

I rolled to the side, allowing a space to appear between us, and took both his cock and my clit in my hand, pressing them together. Gently I wanked them, as David remained motionless, until he kissed me, an unspoken way of saying it was ok. Lost in the kiss as I held us both tight together.

I rolled off the sofa and onto my knees on the rug, but I wasn't going to suck his cock this time. This time it was different. He turned to face me, sitting on the edge of the sofa. I worked his trousers and pants down past his feet, and slid them to one side. Taking my hands in his, he helped me rock backwards on to my stilettos and get up. I could see his cock was erect now, and exposed to the world. As I stood in-front of him, the head of my clit poked out of my shiny black leggings. It was the first time he had seen me like that. I slowly unzipped the front of my leggings and pushed them down with my thumbs, completely exposing myself to him, my man. Something I hadn't done in many years.

In the light of the fire embers he saw another penis for the first time. He didn't think, and just tried to allowed himself to enjoy the experience.

I walked forward got astride him, riding him, so that his erect penis and my clit were once more together. Gently I took his hands and clasped them around us, and squeezed tightly. We just held them there, and kissed.

With a little encouragement I moved his hands up and down the shafts, so that he was wanking them both simultaneously for the first time. Gently, then faster, then slowly. The light kisses and licks of his tongue left him breathless.

When I was sure he was going to continue to masturbate us both, I could move my hands so that they were around the back of his neck, my fingers pushed though his hair. He was wanking us harder now, cock against clit, and we responded together, as a team. I encouraged him by moaning appropriately, gently biting the lobe of his ear, and licking my tongue across his lips.

In this position it wouldn't take long for me to cum, and I wanted David to bring me to orgasm for the first time, and he did so...

"I'm going to cum." I whispered in his ear, "Is that ok?"

I was my turn to ask permission, to almost apologise now. But he ignored me, and kept masturbating us together with both of his hands tightly around us.

"I'm cumming." I announced breaking the soft silence, "YES, I'm coming!"

We both looked down, to see Davids hands wrapped around both cocks, pressing the heads together. He watched as a jet of white cum came out of my clit, squirting 3 or 4 inches into the air before landing on the two cock heads and his hands. Another, then another until it was leaking cum and running down the head of my clit.

He didn't know if he should stop or continue, he had already cum once today, but I wanted him to do so again... I took two fingers and wiped my cum from his hands as he kept wanking. The jizz glistened on my long black fingers-nails as I spread my cum onto the head of his cock, sharing it between our cockheads, to coat them together with my cum.

I rubbed the palm of my hand over the tip of both cocks, lubricated with sperm so that they felt as one. And then he came.

He jerked back, but kept wanking us. He twisted back again, for 5 or 6 seconds, until he couldn't contain his release, and then came into my hand as I shared and exchanged his fresh lubricating cum between our two glistening cockheads.

He knew he hadn't felt anything like this before. Nothing like this before.

Being inside a woman, being inside a bottom, even me giving him head had not been as intense, as intimate as this. They were all suddenly insignificant.

I held our cocks together and tried to wipe up as much cum from him as I could. I wasn't sure how he was feeling, but I thought that I should clear up as much as possible whist he came to terms with what had just happened between us.

I stood up on my heels and tucked myself into my leggings, so that there was no evidence of my cum or my clit to be seen. I felt the sperm on my clithead quickly cover my stomach and flow to my groin. I'd definitely need to clean myself up.

David sat back, and took up a cushion and placed it on his thigh, casually hiding his penis.

I took his hands, helped him stand, and hugged him. He was still holding the cushion.

He whispered to me, "I never thought it would feel like that."

"Is this in a good way?" I responded.

"Nothing has ever felt intimate like that before." He said, "It's a whole new experience."

I wasn't sure if I was supposed to say "We don't have to do it again if you don't want to." I couldn't work out the emotions he was currently feeling.

When I touched my first penis and made it cum, it felt like the most natural thing in the world. Like the universe made sense, like that's what I was born to do.

I understood for David it would be different. He wasn't wired this way, it only happened to him because and only because he found himself dating a transwoman.

All those negative feelings, and guilt people talk about were about to hit David hard, like a tidal wave. Like a brick wall. When the adrenaline and thrill of orgasm had been fully drained, and a new reality sets in.

It happened to David after he had cleaned himself up, and we were back in the lounge with a drink in our hands.