Emma's Stiletto Seduction Pt. 19

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

Emma's stiletto seduction 01 to Pt. 18 for prior entries.

Comments welcome.

"I didn't know you kept a photograph of us here." David said, speaking from the bathroom as he wiped the sperm from his penis. "Will you bring it with you when you move in?"

...

We had just performed our first role-play together as a couple.

It felt a lot more intense that I had ever imagined. I thought that I had role-played during sex before with previous partners, but I now realised that was not true. I was pretending. When I dressed as maid at a hotel to have sex with a 'guest', I was only wearing the outfit. I wasn't thinking of actually cleaning the bathroom afterwards. It was superficial.

But when I had discussed a role play with David, to keep our sex life full and exciting, it cut too close to the bone.

It was easy to see him as an Estate Agent who came around to value my flat. It's not so dissimilar to his real job as an accountant. A change of watch, and a flashy attitude was enough to convince my brain that my boyfriend was someone else.

"Wasn't that the idea?" I told myself.

But in the scenario, I wasn't the person role playing. I was myself, Emma. And I had allowed myself to be seduced by the brash estate agent.

It never once felt exciting. It never once felt taboo. It felt too much like cheating. It felt too much like having sex with someone other than David.

I felt an emotion that I had never felt when having more casual sex-partners than I should...

I felt guilty.

I loved the man who he was, not the character he was playing.

On a deeper level, it did feel like I was cheating.

The day after our role play, it felt odd that an actual agent had visited us. Still, their valuations were good. If I sold my apartment, it would provide me with around three hundred thousand pounds cash into my account. Renting it would provide a return of around 7%.

I had stayed over at Davids' house many times in the eighteen months that we had now been officially a couple. Even though I had seen other men with my boyfriends permission in that time, sometimes with him and others on my own, the 'sharing' part of our relationship seemed like the distant past.

But now things were different. I was no longer visiting David, his house had now recently become the house where I also lived. His home was was my home too.

When David and his wife had first moved into the detached 1930s property on the coast of the UK, he thought it would be their forever home. He had resigned himself to the fact that he was stuck in his marriage. This sexless and unloved marriage from which there was no escape. But the lockdowns due to the Covid pandemic had placed more strain on their relationship than ever before, and provided his wife with the excuse she needed to leave him.

At first, just to "look after her sister" who had apparently been unwell. But that was not true. It was only a reason to leave, and she never come back. David thought that she had never really moved in to their house. Most of her things were still in storage, a space they had rented whilst moving from their previous property. The only things that she had moved to their new house were her clothes and work computer. And she had taken most of those when she left.

The few remaining signs that she had once lived here had been slowly removed. Photographs that were initially too painful to look at had been placed face down, and then put into a plastic box in the attic space. Her remaining clothes had received the same treatment.

In fact over the last two years David had slowly been sanitising his home of her. All the ornaments and things they had purchased together, all the clutter you generate from over 30 years of marriage wiped away. He needed a clean break, and harshly she provided him with one.

So much so that David had told me that she hadn't been back in contact with him, or even through their shared family, in over a year.

And yet it was him moving on with his life. His wife had constantly reminded him that if she left, no other woman would want him. And that she could easily move on and find someone else. Someone better.

This hit him hard in the weeks that followed her initial disappearance. As she packed her case, his worst thoughts were that she would never return and he was proven correct. He had suddenly found himself all alone, perhaps for the first time in his entire life. He felt like he had no one.

Even though the house had three large double bedrooms and a smaller box room, David had insisted that I move into his bedroom.

"If we are going to do this, lets do it properly." He suggested.

I could have moved into a spare bedroom here, and we could have shared a bed for sex and after which parted to our own space. But that was not what I wanted. It was not what we wanted.

A few days earlier David had cleared space for me in his bedroom, that was going to become our room. He generously allocated me most of the wardrobe and the dresser was also going to become my domain.

The box room had been cleared to give me chance to place things that needed to be moved from my apartment in temporary storage, and garage space made for items that were not needed day to day.

I placed my cd collection next to his in the lounge by the hi-fi. Yes we were moving in, but were were not ready to merge music collections yet.

"Perhaps in another eighteen months." I joked.

When the last of the boxes were in their correct places, David brought me up a cup of tea. Staring back at me was most of the 40 plus years of life, all neatly packed away in cardboard.

I was exhausted, even with the two of us it had taken the better part of the day to move the delivery from our removal van. It seemed so much, and yet so little at the same time.

I sat on a box with David stood next to me, he placed his hand on my shoulder. I had done some crazy things before in my life. Meeting strangers for sex, meeting many strangers for sex, but nothing was giving me the rush I was feeling now.

I had signed a contract with the new renters at my flat. Whatever happens, they were there for the next six months at least. I could not go back. There was no going back now.

This house, Davids house, was my new home.

I felt David squeeze my neck and leave the room. He sensed that I needed a moment. He too needed a moment.

His life had changed completely now. From the loneliness and despair that seemed only a handful of months ago, to this. His girlfriend moving in with him.

But of course I was no regular girl.

I had been on hormone treatment throughout my gender transition, and was now open and out at work as a transwoman. I could pass in society as a woman, the changes in my small framed body adapting well and accelerating my level of acceptance of my new sex. My one regret was going through a male puberty, but things were different back then. It would have been impossible to tell parents or explain to doctors how I felt. Even if I did, I would have been shunned, disbelieved, and probably put into counselling to try and 'correct' me.

But I was doing it now, better late than never. And thankfully my natural body plan and being a small human was finally working to my advantage.

During our relationship I had kept the logistics and reality of being a transwoman as far as I could from my boyfriend. For all intents and purposes he was a straight, white, middle aged man with absolutely zero experience with women other than his wife. He fancied women, especially goth women he had confessed to me, and although I was a transwoman rather than a cis woman he had taken this in his stride.

I didn't quite know how living with him would change things between us. He would definitely see more of the tricks, peer behind the curtain to a cocktail of drugs, laser treatments and voice coaching techniques that had been hidden.

But the thing that worried me most was time. When we had been on dates, and I had stayed over, he wasn't quite aware of the time I needed to get ready each day. To lead a double life sometimes it would be helpful to have forty-eight hours in a day.

A few weeks ago we had sex together in the shower of what was now "our" bathroom. It was one of the few times that David had make me cum. My genitals were still able to become aroused and, as a consequence, achieve orgasm. It is the elephant in the room for most male & transwomen couples, unless the transwoman has had what's known as 'bottom surgery'.

It's not just how to handle it, even knowing what to call 'it' can become troublesome. David was very honest about his lack of experience in this department. He knew that I wouldn't want it called my 'penis', or 'cock'.

"Just call it my clit please." I asked David when the occasion arose. "It's practically the same thing anatomically, just a bit bigger than most women."

"Ok." David agreed, feeling relieved that he now knew the correct nomenclature.

It was in the same conversation one evening that we also got to name my hole too. He had been happy to call it my "arse" or "bottom", but was pleasantly surprised that I was happy for it to be called my "pussy" or my "cunt".

Although he was shy of using these terms in conversation, he was pleased that he could now increase his vocabulary when texting me the things he was going to do to me when we got home from work.

I would check my phone at my desk and look at messages...

David: Emma, I hope your pussy is not sore from last night? X

And when he was particularly daring,

David: Would it possibly be ok if I fucked your cunt tonight Em, I need to empty in you x

Of course these messages made me instantly forget the topic of work in hand at the office, and turn my attention to how horny they made me feel.

At work we had not told anyone that we were living together or even together as a couple. Some days we would travel to the office in Davids car, on others we would both take separate cars if we were expected to start and finish at different times.

People knew we had been friends before my transition, and when they witnessed us leaving together it could easily be explained that "I'm giving her a lift" or "She has had to move out of her apartment."

Mundane explanations seemed to quickly satisfy curious eyes rather than create a web of unbelievable, fanciful lies.

This was the first time that I had ever lived with a partner. One of the many things that I had not realised was that although sex was on tap every evening, for we were in the same place together, it did not necessarily tie up with the times that we were both horny.

"You cannot set your internal sex-clock to 9.30pm every Tuesday and Thursday." We joked.

It was on one such occasion that things changed for us. I had become accustomed to David texting me in the office when he was horny, and vice versa. But today things were different.

David: I'm horny and I have no work to distract me! X

Emma: Lucky you. X

David: What are you wearing? X

Emma: Oh you perv! X

Emma: And you know exactly what I'm wearing, I saw you at breakfast :) x

David: Don't be a spoilsport, please tell me x

Emma: Ok lets see....

Emma: I'm wearing my tight black wet look leggings.

David: And? X

Emma: A pair of block heeled black leather ankle boots

Emma: A white blouse

Emma: And a woolen knit large grey cardigan!

David: Really?

Emma: Well yes, didn't you see? I don't want to go over the top here. X

David: Well I like it x

Emma: What you don't know is that I'm not wearing any underwear today! X

David: Why not? X

Emma: So I can give my nipples a chance of pushing out through my blouse :)

David: stop teasing me. X

Emma: You know I never tease x

David: Now I'm horny x

Emma: You want me to take care of you babe? x

David: I'd love you to, princess x

David: But we shouldn't....

Emma: Shouldn't we? X

Emma: You have me horny now x

David: Stop it x

Emma: You started it x

David: I want you x

Emma: What do you want, David? X

David: I want your mouth on my cock x

Emma: I want to suck your cock! X

Emma: I want you to feed it to me baby! X

Emma: I want you to cum in my cockslut mouth! X

David: Meet me in W408 in 10 minutes x

Building W was an old office block on the business' campus, only the first two floors were currently occupied by staff. The 4th floor had been vacated 2 years earlier, and had been mothballed to reduce upkeep and heating.

I quickly took my shoulder bag and phone from my office, and walked passed the few members of staff working in the area. They did not look up from their computer screens, they would not miss me for 30 minutes.

I tried not to think about things. We definitely should not be doing this, it was a risk to both of us. But sometimes things naturally happen in this spontaneous way. We hadn't had sex in a week.

I listened to the sound of my plastic heels echo through the car park, reflecting off the brick, concrete and glass facades. I could tell my anxious pace was quickening. I wrapped my cardigan around me and held it tight, trying to be anonymous.

It helped that I took the back staircase of the building and climbed the four floors. I was warm now, an intoxicating mixture of effort, excitement and adrenaline rushing though my veins.

There was absolutely no one around. The space on floor 4 was a mixture of stud-wall corridors, abandoned offices and seemingly a place to store old unwanted chairs and desks. One former office room was full of beige coloured computer towers that had apparently not been used since 2003.

David was not here, he texted me specific instructions to be in room 408 and wait for him there, "on your knees x"

I found my eyes quickly darting around revealing my own nervousness. I knew this would be a risk, a huge risk to both of us.

But David had in the past gone above and beyond for me. He had indulged me in my love of sex with others, to the point of arranging for me to and then watching me have sex with another man.

If we had now put that part of our relationship away, it would be in these instances, the role play sex as an estate agent and client, the quick blowjob at work, that would have to replace the lost adrenaline rush of casual sex.

I walked through the door of W408, the hydraulic piston closed it quickly behind me.

The room was small, windowless, and the brief glimpse I had of its contents revealed a heavy steel framed rack against one wall and several crt monitors placed on it.

The bottom of the door brushed against the carpet tiles, it was so snug that no light could enter through it.

It would be odd if I was found here by others in the dark like this. But it could be explainable.

As I got to my knees in the centre of the cupboard, it would be even more embarrassing to be found like this and certainly not explainable.

The floor tiles muffled the sounds of a person approaching. I felt like closing my eyes, but what good would that do?

The odds were that it was David, of course it was, but I wished that my brain had told my heart, that was now thumping hard through my chest.

The footsteps were inaudible now, I could only sense them through the slight movement and vibration on the floor through my knees. They stopped outside.

I placed my arms behind my back and closed my eyes as I had been instructed. Whomever was next through the door was going to see me like this, and it would not be able to be explained away to the management by anything other than I was kneeling down, expecting sex.

The door opened, then closed.

It was too late now. I would have to accept the consequences either way. Sex, or utter embarrassment and most likely the sack.

In that brief moment I swore to myself that this would be the very first and last time I had sex at work.

I heard the faintest sound of the door latch closing, and the snib being locked. Whoever it was we were here, locked in together alone and undetected in the darkness.

Hands quickly found me, they had seen my position when the light flashed in from the open door. They took my arms and lifted me upright.

Because I was not in high heels, the figure towered over me by nearly a foot. I felt him bend down to kiss me and he did so. It was one of the few kisses we had shared where I wasn't wearing any lipstick, but it didn't matter, I recognised it immediately. Davids tongue forcefully entered my mouth. Our passion completely enveloped by the darkness all around us.

I knew what he wanted, and I wanted it too. I pulled way from him and groped in the dark for the front of his trousers. They concealed a tent pole of an erection that was soon pulled out in front of me.

I didn't need to kneel down, but just bending over gave me the perfect head height for me to suck him. I took his length quickly inside my mouth, and I could hear him fighting to keep calm and silent.

I wanted him to satisfy himself using my mouth and throat.

It is difficult for any transwoman who has not yet had any lower surgery. I felt the need to complete with cis women, cis women who had a pussy for their boyfriends to fuck, and to really fuck hard at that.

I only had two holes, and men like to really let themselves go and fuck. I realised at a very early age that I simply had to let men fuck my arse, and also that I had to let men fuck my mouth.

Not just a blowjob, sucking their cock until they cum, but let them really fuck my mouth as if it were a cunt. If you are looking for a search term to describe it, I would recommend the term "skullfuck".

It was one that David and I had exchanged a few filthy text messages over in the past, but this was the first time he had whispered it to me.

He always seemed so calm, and gentle. And in little over eighteen months of us being together here we were, in the dark confines of a disused office store cupboard, and him asking to skull-fuck me.

In the pitch black, I felt his hands move to the back of my head. It was usually one hand only on my head, if I was sucking him off, the other wanking his cock into my mouth.

But now he had both hands gripping my head tightly, his fingers interlocked and clasping me to him.

David fed me his length, slowly at first, but beginning to take advantage of my position. I wasn't kneeling anymore, I was on my feet but bending forward. It was much more advantageous for him to go into my throat this way.

And he began to fuck my mouth. His hard cock penetrating my lips until the tip reached the back of my throat and rested against it.

I tried to remain calm, resting my hands on his waist, breathing deliberately through my nose. He pulled my head onto him, and I swallowed the head of his penis.

Slowly he pushed himself 2 inches past by tonsils, and just as smoothly removed himself. I took a silent breath.

We had deep-throated before, but mostly blowjobs were more about licking and sucking his cockhead with my tongue, lips and piercing. If he wanted to deep throat me, I thought that he must be extremely turned on by it in this situation.

In the darkness, in his mind and to his cock, it did not matter if he was fucking a mouth or a pussy. To him it was tight, and wet, and welcoming to his hard seven inch length.

He just wanted to fuck now, to fuck and cum. To cum and go.

He fed me his length with a repetitive rhythm. He would rapidly fuck my mouth, 5 strokes in and out. On the last stroke he would hold his cock against my throat, and push it past, and shallow fuck it, being careful not to remove it completely, and then allow me to gasp a breath again.

I didn't need to pull him back on to me, he was in complete control now. He was rough, deliberate, and allowed himself to be indulged in the darkness. Yes, he was skull fucking his girlfriend Emma, but he was also just enjoying himself fucking a mouth and throat without any limits.