Emma's Stiletto Seduction Pt. 14

This is a continuing story, please see :

Emma's stiletto seduction 01 to Pt. 13

Comments welcome.

The previous weekend David and I had come to a realisation, one that would change our relationship forever. That, as a couple, we could survive him sharing me with other men. This is worth thinking about more closely.

As a trans woman in my 40s, my relationship with David was the first that I ever had where I was sure that we could work through the monogomy issue. It was unfortunate that I had to wait so long in my life to find him.

If you have not read my previous diaries, I had recently came out as trans woman at my workplace during the covid period. I had repressed my transexuality during my 'normal' life for so long, that it just seemed like the prefect opportunity to tell the whole world. Collegues would have some time away from the office to get used to it.

After a bit of work gossip about me, it became nothing special anymore, the tongue wagging gossip had moved on to other topics. Especially as I didn't often dress fully femme at work, but more gender neutral. Yes, my hair had grown out, as had my breasts, but most people just got on with their day now and left me alone after the initial curiosity had settled down into mundanality.

Aside from one work colleague that is, someone who I now called my boyfriend, David. Even though we worked together at the same company, we were not together as a couple at work, only outside of the workplace. At this moment we had both agreed that this policy was for the best. It had proved the correct choice, as we were still together nearly a year after we started seeing each other

David was an older guy now in his 50s. Tall as you would want at 6'3, and a perfect gentleman. Perhaps too much of a gentleman. I was his first. His first transwoman anyway and he had only been with one person before me, his wife of many years.

Unfortunately his marriage had become sexless, joyless. During enforced lockdowns from covid the cracks in David and his wife's relationship has been exposed. He had not been happy and neither had she. He had learned to repress his sexual urges and, like the loyal husband he was, just learned to live with it.

After years of this unfulfilment, David and myself had fortuitously found each other at a similar point our lives. We were both thoroughly enjoying the release that our new found friendship offered us. David could finally live out his sexual fantasies, and I could be with someone that wasn't just for sex. It was sex with someone I fancied.

It just worked for us.

I made it known to David that he was enough, more than enough for me. But if it were possible, that I wanted more. After years of just being with men for short periods, sometimes even for only 5 minute encounters, I had been conditioned to be able to separate sex and love. To me, sex had become a physical thing. I could have sex with any man, it was just a physical act of pleasuring them. It was just moving my hands up and down on a penis and making them cum. It became to me like shaking hands would to most others. I was able to gain pleasure from pleasuring others, and I felt a need to pleasure any man, to bring them to orgasm, that wanted me to do so.

I never hid this from David. At first he was wary, but I assured him that I would never cheat or leave him. I would never meet someone he didn't want me to meet, or that he didn't approve of. And if he ever asked me to, he would be the only one for me.

David accepted this, but it was difficult for him at first. Our relationship as a couple was going very well, but he knew that sharing his trans-partner would be a risk too and one that took a while for him to feel comfortable with.

After our first 'threesome' encounter as a couple, with a stranger called Howard, David had felt that perhaps this was too much for him, he had not enjoyed it.

But after a chance meeting with David's work colleague Richard, where my boyfriend suggested that I help relieve Richard during a lonely period of time after his divorce, things had changed.

It wasn't the sharing of me that David had found troublesome with Howard, but rather jumping in feet first. We had needed time to establish some ground rules, and to be more confident in our strength as a couple. David now thought that no matter what, his girlfriend actually wanted to be with him unlike his wife. And he was right.

I have been trans all of my life, but covid had provided me with the opportunity to take things to the next level. Coming out as trans to David was easy, he was the only man that I had ever fancied and it seemed like the perfect opportunity. Ever since I seduced him that fateful night last year, which I refer back to as "our first date" and David refers back to as "The first time you sucked my cock", we had been together. Unconventional yes. But nevertheless exciting.

I wanted him to know that I wanted him, and would always want him.

This didn't come easy for David. Fresh out of a long marriage. After taking a break to see her sister, his wife had decided she was no longer going to return home. David felt a sudden rush of loneliness.

He was heartbroken for the loss. But after meeting me he had found that his loss was not that of his wife, but he was grieving for the loss of excitement, passion and yes, sex, that she had robbed him of for so long in their marriage.

He had decided not to live like that anymore, and had been surprised to find that he could find exactly what he had been missing by exploring life with a goth trans-girl called Emma.

Me.

Our first threesome had not worked out with Howard, he had been rough and David found it hard to watch him treat me so badly.

When David offered me to his friend Richard, he knew that I would be taken care of, or at least not be treated so badly.

And last weekend David had arranged an opportunity for me to meet with and seduce his mechanic, the third time he had shared me was an opportunity that worked out well for everyone. The sex with David afterwards was electric.

Much to David's surprise, he had found that he could discuss the details of my sexual encounter without being jealous, but then he was hanging out of the back of my bottom when it was first brought up in conversation. I assumed that for David, discussing things when he was penetrating me is the best way to be secure in a relationship.

He came inside my anus for the first time, or rather the first time without a condom, filling me with his sperm. It was raw, animalistic, marking me as his territory as he heard in detail about me sucking another man.

In the following weeks David found himself feeling more secure than ever. He wasn't worried that I would cheat on him, for I was having sex with him and others with his knowledge. There was simply no need to cheat on him or lie to him. It removed that idea from ever happening.

But he also found the idea of his girlfriend being with other men exciting. He had often dreamed about his ex wife being with other men, but usually in nightmares. This time he was determined to have pleasant fantasies about his current girlfriend having sex with other men, to focus on it as he masturbated himself, and to encourage it more in the future.

I checked my phone messages...

David: I had another dream about you last night Emma x

Emma: You cant get me out of your mind! X

David: You have had quite an effect on me! X

Emma: Yes, you are even using exclamation points in texts x

David: I know, sometimes even a smiley :)

Emma: lol

David: Anyway...

Emma: So what was it then, should I be worried or prepared?

David: Oh I can't commit it to text, far too filthy x

Emma: Spoil sport

David: definitely.

Emma: Tell me at the weekend? X

David: Only if you share some of yours. X

Emma: A shared fantasy weekend?

David: I like the sound of that!.

Emma: I'm not committing to doing them though...

Emma: unless i want to x

David: or me to yours! X

Emma: Oh another exclamation point x

David: Shut your face.

Emma: :p x

This weekend we had arranged our usual date, I would travel over to Davids house and we would spend some time together, have sex, and then get ready for work the next day. Even though we worked for the same company, we were still arriving separately to maintain an air of privacy. One day we would have to come out to more people, but not yet.

It was over breakfast on Sunday morning that the subject of fantasies finally found its way back to the conversation.

We had already acted out some in our relationship already.

If we exclude the prior threesome and the sharing, David had taken me to have my tongue pierced - a major fantasy of his that he had not been able to suggest with his wife.

I had also been subject to getting wet and messy too, when David has covered me in a dozen eggs at the breakfast table.

But they were reality, how would his fantasies be any different?

"So what did you dream about then, babe?" I asked David in my posh, crystal clear accent.

"It was a strange dream," David replied, "nothing too weird I can assure you."

"That's a shame." I replied grinning, "But I'm glad you are dreaming about me - that's a good sign."

"Well actually you were marrying someone else!" David exclaimed.

"Never." I replied quickly.

David laughed, "You got married to someone else and I fucked you whilst you were still in your wedding dress."

"What, at the reception?"

"Yes, at the reception."

"I'm not sure what that means for us." I giggled. "I think you still have issues."

"I told you it was a weird one."

"Well at least you are having sex dreams now about me," I replied, "I'm happy about that."

"It's always been a fantasy of mine." David admitted, "It must be attached to a memory or something, but the idea of having sex with a women who is still in a wedding dress has always turned me on."

"Kind of wrong, taboo?" I suggested.

"Yes, its probably exactly that." Said David, reassured.

There was no doubt that the best sex was always slightly taboo. Slightly wrong, that you shouldn't really be doing it but you just can't help yourself in the moment.

I supposed dating a trans woman like myself was part of that taboo for David also, so much more exciting this way that dating a cis woman.

I knew it was a matter of time before the next question came...

"Are you going to share any of your fantasies with me then, Em?" David asked.

But I was wrong about the question.

"I thought you were going to ask me something else then." I said, shocked.

"What was that then?"

"I thought you were going to ask me to get a wedding dress so we could act it out."

David laughed and then asked, "You would?"

"Sure!" I replied. "We can definitely do that if you want."

"Great." Said David, his mind already starting to allow himself to wander back to his dream that could now actually become a realty.

"But your turn." David interjected into his thoughts, saving them for later...

"You know mine are going to me a bit extreme don't you?"

"I expect nothing less." David replied, although I could sense a mild apprehension in his voice.

"You already know what I like, really." I suggested, "My fantasies are usually exaggerated variations on those themes."

"Remind me, please?" David asked.

It wasn't the usual conversation over a breakfast coffee and croissant, but I was game. I certainly wanted to encourage David to share more of his own desires and this would be a way of helping us talk about more things.

"It's the usual ones," I reassured him, "I like dressing up."

"Yes"

"I like the idea of being with lots of men at the same time."

"Ahh yes."

"I like fantasies where I get wet and messy too."

"Like what we did with the eggs that time?" David asked.

"Yes just like that." I added, "But with cum and other things too."

"Other things?"

"Hey!" I exclaimed, "I'm over sharing here. It's your turn."

David wanted me to continue the conversation we were having about my own fantasies, but he conceded that to do this he would have to share more of his own.

"I fantasise about having sex in places where I shouldn't sometimes." David said, shyly.

"Like anal sex?" I added, cheekily.

David laughed, and his face warmed the room once more with his smile. I liked him a little bit more.

"No, like you know, places."

"What places?"

"Like fitting rooms in a store, or a cafe toilet, or the back row of a cinema."

"Oh they all sound like fun." I added.

David grinned back at me, and he breathed out and relaxed once more. A sip of coffee was taken.

He had been brought up to keep things like this to himself, never to share such private thoughts. It was a relief to simply tell someone, and a thrill to air them with a partner.

"So you were saying," David encouraged, "what else aside from sperm?"

We may have been dating for a while now, and had shared many experiences, but David still struggled not to be too formal, and using words like "cum" instead of "sperm" was still not quite there yet. I found this endearing and part of his charm.

"Ok, piss." I revealed.

"Urine?"

"Yes, one of my recurring fantasies involves piss." I confirmed. "If you want to call it urine that's fine too."

"Ok." Said David, trying to remain cool whilst his mind wandered and wondered exactly how urine could be involved in a sex fantasy.

"Think being a human urinal." I interjected, noticing his puzzlement.

"Ahh." Said David, trying to stifle a blush he could feel rising in his cheeks

The room fell silent for a while, whilst we sipped our hot coffee and both wondered if the other was being turned on by the conversation.

For the record we were, but both trying not to let on.

"I fantasise sometimes about taking you dogging." Said David, unsure of the words he found surprisingly coming out of his mouth."

"Oh Ok." I replied.

"I'd sit on the back tailgate of the car whilst you bend over and suck me, and offer your hole to a lineup of men."

"I wasn't expecting that from David." I though quickly to myself, not wanting to discourage it.

"I thought you wanted that hole all to yourself?"

"Well, it is a fantasy not reality." David reassured himself, but finding his cock twitching in the brazen way he spoke to me.

"I fantasise about being the centre of a blowbang bukkake." I added, as nonchalantly as possible. "Sucking off lots of men and having them cum on my face."

"Oh I'm aware of what it means." Said David, surprisingly. "And if you can't make a man cum with your mouth after five minutes they get to fuck your arse."

I blushed, and nodded. "Something like that."

"I'd like you to change your ringtone on your phone to the sound of you gagging on my cock." Said David, feeling encouraged by the revelations we were both sharing, each fantasy encouraging the other.

"I'd like to pick up strangers at a public toilet, and suck them off whilst they pissed."

"Wow." Said David.

"And the dirtier they are the better." I added.

"I'd love to take you to a restaurant and make you piss yourself." David added, "And then piss on you in the car park."

I blushed, and looked down at my coffee.

"You have done that, haven't you?" David through to himself.

"Anyway, I want to be airtight and skiing."

"What's that again?"

"A cock in both holes, and one in each hand, like ski poles as you wank them."

"Ahh." David laughed.

"I'd like to play a sex version of musical chairs." David added, "Where you get a line up of women and when the music stops each guy who is facing a woman gets 30 seconds to fuck her mouth as hard as they can before the music starts again."

"That sounds like fun." I responded, "Being a "mouth" in a line up of mouths does have its appeal. The anonymity."

"Especially if we are all wearing masks." David added thoughtfully.

"Well this is a lot of revelations for a Sunday morning." I commented.

The conversation had us both turned on. It was the first time that we had discussed our private fantasies and the ideas did start to intrigue David.

"It's certainly interesting to talk about things."

I nodded.

"It's only words, it's ok to have fun with them."

I knew that for David letting himself go, even with words rather than actions, was never going to be easy. He had been brought up a gentleman, that women were to be respected. he would never use crude language in their company, let alone it be directed at them.

"I've never found this easy." David admitted.

"But its fun to talk dirty." I encouraged, "When you call me a 'slut' I know you don't mean it. It's just in the moment."

"I suppose."

"Why don't you call me a slut right now?" I asked.

"But we are having breakfast."

"That's the perfect time to practice then."

"Just call me a slut."

David stopped for a moment, he wasn't used to this. Perhaps letting out one or two words in the heat of the moment was sort of acceptable, and if not acceptable certainly understandable. But this was different. It was like an invisible boundary to traverse.

"You know I like being called names," I encouraged, "it's ok."

David remained silent.

"Look, you know I want you, we are together, you aren't going to upset me."

David nodded.

"You..." David started.

"What am I? I said, poking out my tongue at him revealing my piercing.

"Slut."

"Your slut." I added.

"My cock slut."

"That's right!", I smiled, "Tell me what I am."

"You are a filthy fucking slut." Said David rather calmly.

"And what do you want to do to me?" I provoked.

"I going to put my cock in your slut mouth."

"Are you now?"

"I'm going to make you gag on my dick."

"Choke me with it?"

'I'm going to put my cock in your slut mouth and cum in your throat."

With each sentence we were getting more and more turned on. It was like we had passed a point in our relationship that would take us to a new level. Being able to talk freely, and use language that we would never before.

Over the next few days David would make a point of texting me when we were at work. Previously we had just expressed pleasantries and asked about each-others day. Or made a date for the weekend. But things had changed.

At the most inappropriate moments were we now exchanging things that could only be described as utter filth.

When I knew David would be busy in a meeting, I would time my texts so that he would be forced to read them and be completely shocked and unable to respond.

I sent him a text message...

Emma: David, when are you going to piss in my mouth? X

I knew it would turn him on.

David: Emma you fucking whore, I'm going to push your stilettos up your arse whilst I feed you my cock later!

And with this he turned me on too.

A few weeks had passed, our relationship getting better each day. He was such a good man, a great man, and I felt very lucky to have him. But I could feel things welling up inside me. My stomach knotting. I didn't want to make waves or spoil our connection, but it was time for me to explore others again.

It was over a bottle of red wine that I felt confident enough to bring up the subject.

"David?"

"Yes Emma?"

"I think its time." I suggested, casually.

David instinctively knew what I meant.

He had become very happy, settled and had loved the closeness and intimacy that had strengthened between us.

Not quite yet able to voice his approval and understanding, he nodded subtly.

"If you have any thoughts how, let me know." I added.

I wanted to make David a part of this, if he wanted or felt able to be. Although I'm sure that he would have been ok if I had just gone out, had sex with a stranger and come home, I still felt that in all of our previous encounters he had at least known and played a part in choosing who, how and and when. He had with Howard, Richard and then his mechanic.