Emma's Stiletto Seduction Pt. 22

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

Emma's stiletto seduction 01 to Pt. 21 for prior entries.

Comments welcome.

It has been a long and difficult time since I last wrote to you, I can only offer my sincerest apologies.

Life had been going well, so very well for my Boyfriend David and I, but it was changed, possibly irrevocably so, on that fateful morning.

An appropriate phrase would be 'the day after the night before', where David and I had our first unofficial outing as a couple to the work Christmas party.

We had arrived at the party together, which was not uncommon as we worked at the same employer and were known to be old friends on the campus. But many more eyes were on us taking note, as we left together. Especially as our office colleagues had seen me, the real me, for the very first time.

Of course they had all known I was a transwoman, these things are absolutely impossible to keep secret. Especially if you are transitioning at work and in public.

Everyone believes that they are great at spotting "trans", or more correctly 'reading' a transwoman.

Which is true, for the most part, you do notice one hundred percent of the transwomen that you notice. However, most people don't realise that for every transwoman that you see, there are perhaps another dozen that you don't see. Invisible to you, just going about their day and minding their own business.

That is the profile that I had previously kept at work. Yes, they all know, but it's no big deal. It's just "Emma" who comes to work, sits behind a desk, and then goes home. They may see me in the canteen from time to time, or in the car park, but its probably safe to say they most people knew of me just by the gossip of my existence rather than ether seeing me with their own eyes. And fewer still those who had actually spoken to me.

But this status-quo had changed, in an instant, when David and I had entered the office Christmas party last year. There was no mistake, I made an impression and there was to be no hiding in the future. The men and women around me had their interest piqued after a few drinks. After a few more drinks they were much more than simply interested.

But nothing raised more eyebrows, and started more gossip than David and I walking out to the same taxi together. Of course, thankfully, none of them knew that we were a romantic couple and had actually been living together for most of the year.

Our colleagues also didn't know that I sucked my boyfriends cock on the way home from the party, well, no one if we do not include the bemused taxi driver.

For the both of us life had become settled, an exciting and explicit routine. It was unconventional yes, but in our own way we had made it work very well. It was too good to be true, and I wish that we had made even more of that initial time we had together.

The arrival of his wife the previous night had changed things.

Even though she was only seen on camera, as David had watched the video on his phone over breakfast, he felt ill to the pit of his stomach. As he handed the phone to me to look, I also felt a cold shiver run down my spine.

I watched closely as David subtely bit his bottom lip, and a slight but perceptible shake of his head lasted a few seconds.

David was never good at showing his feelings. Even though he had reached his late 50s, I thought that I had helped bring out and encourage that side of his personality. It was inevitable during the adventure we had already shared to date. I began to get concerned to how this was going to affect him and our relationship going forward.

Over a second breakfast coffee we decided to put the two things we were worrying about away for the holidays. Whatever his wife wanted him for, we were going to find out when it happens. And the reaction from our work colleagues can wait until the new year.

Thankfully our plans for Christmas was for it to be quiet, just the two of us. I was hoping to make it as nice as possible, and recent event had doubled my determination.

We were going to cook a meal, drink as much champagne as possible and relax in front of a fire. I had also ordered some snow for the UK to help make the atmosphere perfect but, alas, the weather was its usual self. A cold wet drizzle or rain.

It made the log fire we kept in the hearth more special.

Not having to get each other presents was also another great idea, no rushing around for the perfect gift. It wasn't necessary. It is a cliche, but in this 1930s detached house together we had everything that we wanted.

After the events of a few days ago David and I had been close, but had not had sex since. We had reached the stage of our relationship where we were not newcomers, we didn't have to have sex every night. My knees and Davids back were probably thankful for this, even if our minds were less satiated.

In our relationship we had sex when we wanted to, or rather when David wanted to.

When I type those words it sounds bad, I know. But this is exactly how I had engineered and encouraged it to be. Yes, I could seduce David and would then be able to have sex. But if he wanted it, I would give myself to him whenever, wherever and however. As a natural submissive, this arrangement was perfect for me.

A sufficient time after a pleasant dinner, relaxing by the fire, listening to nothing but the oily crackle of soft wood burning, I wanted to give David our 'present' as we had called it.

We had discussed it a while ago, during one of those splendid times when spooning in a warm bed, both content, spent, and still in the thrill of post-orgasm.

"Is there anything you would like that we haven't done yet?" I asked, wriggling slightly to reposition myself so that his cock was nestled between the top of my thighs and my bum

It was an action to part distract him, I knew that he would find it easier to respond that way. HIs hand found its way from my shoulder to my waist, and then to my suspenders.

He ran the strap between his fingers and thumb, pulling it tight and then letting it snap back to my skin. Repeating the process that he seemed never to get bored with.

"It should be something we would both like." He commented.

I felt him nod in agreement with himself.

"Now," I replied, "that doesn't always have to be true with me."

It was a big part of our relationship. Although we have never officially described ourself as a BDSM couple, we had evolved naturally to take what you would describe as a dominant and submissive role in our lives.

'BDSM Lite' would best describe it. Or the kind you would happily buy in Marks And Spencers rather than the dark web.

It was part of my genetics, a part of me since I was very young. I knew what role I was born to play, even though on one or two occasions in the past I had been persuaded to play as a neutral or even dominant. But that was just was not me. Like trying to fold your arms the wrong way, or only wearing one sock. A dominatrix role just doesn't feel right. After my last disasterous attempt many years ago now, I swore that I would not try again.

Never again.

David had responded to my submissiveness very well.

It is within most men to be dominant over a woman like me, but so many are unable to practically make it so. They think they can, they may even want to, but often it is just not to be. David and I had taken our time, to slowly but surely get to a position we are happy with and both want to be. That I need to be.

"Ok." David said, not wanting to but, about to say something that he had been thinking about.

He knew that he could ask me anything. Ask me to do anything, sexually. Chances are that I would willingly do so.

He also knew, more than anything, that he wouldn't be ridiculed for asking, as long as they fell within our roles of David being the dominant and me being the submissive. That played a big part in his gaining confidence.

"Ok," repeated David, his hand now running along the skin above my stocking tops.

He had pretended to himself, more so than to me, that he actually had to think about what he was about to say. He knew what he wanted to try, and had been unable to tear his mind from it since he was aware such things happened.

David had always watched pornography, being trapped in a loveless and sexless marriage for decades, what else was he going to do? That's how he had explained his habitual viewing habits. But he didn't have to justify it to me. He had found that his watching of porn had reduced in a direct correlational relationship with the amount of sex he was having.

But on the odd occasion, old habits were hard to break. These days he viewed pornography differently. Not as a way of stimulating his mind to help him get off, but it was body of knowledge, a sex encyclopaedia that covers everything imaginable and even things that you cannot imagine.

He had watched a video a few weeks ago. He wasn't particularly looking for it, had not clicked on any genre or style of pornograpohy, but there it was presented to him in the lottery of an algorithm.

An innocent enough video he thought, unaware that what happened in it would occupy his mind more than he wanted it to. He couldn't shake the visualisation, even though he had sex with me afterwards, fantastic sex, in that time period.

The premise was simple. The amateur actress, as thats how the video was framed, was in a relationship with a man. He was the proclaimed advocate and narrator of the video series, even though disappointingly this was the only one currently uploaded to the adult streaming site.

The narrator had arranged for his girlfriend to meet up with an anonymous man and perform a task of his choosing. If the task was performed within the rules and stipulations provided to them, she would be rewarded. If it was not performed adequately then a punishment or forfeit would no doubt occur.

In these videos there is no illusion of the woman actually wanting to perform the task and to get something out of it herself sexually. It's always from the perspective of the man, and the woman having to please the man.

"Go on." I whispered to David encouragingly, as he had began voicing the scenario to me.

"She and the unknown man knew of the task before they met." Said David, "It wasn't a surprise when she walked into the room."

"What were the performers like?" I asked.

"Well the woman, she was small and with dark hair. She was pretty, but not too pretty. In actual fact she was very, well, normal."

"So not a typical porn actress then?" I asked, finding out more.

"No, not a big breasted blonde." Said David, "The opposite in fact."

I nodded.

"It was like this was real, like they really were doing this." He added, "And it was filmed entirely by the man with a camera in his hand."

"What was he like?" I asked.

"Well he wasn't a porn star either really." Said David, forgetting how intimate this conversation actually was, "If anything he was not like the usual bloke in these videos."

"How so?"

"Well he was fat, for one thing," Said David, who then quickly added, "Not that i'm shaming him or have any place to talk."

"And what else?"

"He was very fat, you actually got the impression that he was chosen as part of the task for her." David responded carefully, "To make it make it difficult."

Keeping up the conversation, so as not to let there be a window of embarrassment, I asked "So what did she have to do with the man in front of her?"

"Yes the task." David spluttered, "She had to suck him off three times."

"Ok." I responded, not feeling what would make this a special event.

"And she cannot take his penis out of her mouth." David revealed, "She had to make him cum three times in her mouth without stopping or taking it from her mouth."

"Ahh I see." I replied, finally finding out what changed this regular scenario into one worthy of making a video about. And one that has stuck in my boyfriend's memory ever since.

I felt his cock stiffen behind me, as he pulled me in close. "Yes, this has definitely had an effect on him." I thought to myself.

/

As much as it had been in Davids' mind and memory, it was also implanted into mine. We had sex between that revelation and now, but it never felt like the correct time to act it out his secret pornographic desire. The last time we had sex was in the back of a taxi and it's not something you want to try with the meter running, it could take a while.

That was one question I had not asked David, in the video he had watched, was there a time limit? Was it completed and were there any rewards or forfeits?

And the one question he had not asked me, was if I had done anything like that before.

/

As David stood up from the leather chesterfield sofa to get another 'Christmas" drink, he heard a muffled sound behind him.

Thump. Thump.

Quickly he turned around to find two cushions thrown on the floor. Immediately he knew what this meant. He had been looking for a sign or an opening this evening to have me, and now it was clear.

As he stepped up to the cushions I was already on my knees in front of him. A position that we had enjoyed each other many times previously, but not like this. This time it was more exciting, like it was at the start of our relationship.

I pulled him towards me and undid his belt. I wanted to get his trousers completely off as he may have to stand here quite a while. At this point I had no idea how long or short a time it would take. I grabbed his trousers and pulled them to the floor. Steadying himself by placing his hands on me, David stepped out of them and kicked them to the side.

I did the same with his boxers, and he kicked them again.

This was how he had remembered it in the video, the man naked from the waist down, with only a grubby blue t-shirt covering his fat upper body. Aside from that he was unknown, we never got to see his face as he was holding the camera. It was shot from his point of view, downwards.

This was the view David currently had, looking down onto this erect cock, pointing upwards to the ceiling. He could see the top of my head, my hair styled into a sleek black shoulder length bob that he loved so much. He watched as I took a looped band from the coffee table and swept my hair back into a pony tail. I wanted him to see what I was doing and not become a mass of sweaty hair.

Davids' cock was perfect, I may have mentioned this before. Cocks come in so many shapes and sizes that all are unique. What most young women don't realise, is that how nice a cock is has no association with how handsome the man that it is attached to is.

In fact, the nicest cocks that I have sucked have usually belonged to the ugliest men. And the smallest, ugliest cocks have been attached to men who are above average in looks.

David was almost unique in this way. I loved the way he looked, even though most would describe him as somewhat plain. Almost boring. No one could look more like an accountant than he did. And he had a magnificent penis. Seven inches and a good girth. Not too much, nothing stupid. And when I pushed back his foreskin with my lips it revealed a captivating bellend.

I often told him I fancied him AND his cock. Like they were two separate entities.

However this wasn't going to be a slow, sensual blowjob with lots of edging, it was a different kind of job. A task, a challenge. I had made David cum a few times in a single sex session overall, although he seemed to prefer once being enough! I knew, well, hoped, that he had not cum in a few days.

I pushed my head deep onto his erection, and buried my face deep into his flesh. The top of his penis had disappeared between my lips and across my tongue, fighting now against the back of my throat.

We could both hear the mucus that I was generating already, and pulled my head away leaving only the bell of his penis between my lips. I couldn't let it go, that was the task. It was also difficult to look up at him, for him to see my eyes. This may be more arduous than I had first thought.

I put my arms around him and grabbed at his bum, pulling his cock deep into my mouth once more. Again, his cockhead hit its target.

"If I couldn't look up at him, he will very well have to hear what he is doing to me." I thought.

But David didn't need to hear, he could see what was happening when he looked down, his cock disappearing into his girlfriend's face. He could feel my lips and tongue at work, hidden, their job to try and milk his cum from his balls.

I had assumed that making him cum for the first time would be the easiest, but he had survived for 5 minutes of his length disappearing inside me before he could relax and allow himself to cum.

He had not been fighting it, as he usually did, wanting to prolong the experience for himself and I. But now he felt relaxed, liberated, it didn't matter if he just let himself go.

And he did so.

He knew the time was 7 minutes and 23 seconds as he felt the first rush of cum though his penis. And then the second, and then the third.

I knew I was correct, he definitely hadn't cum for a few days. This has an effect on the texture, smell, taste and very much the amount of jizz a man ejaculates.

It is strange to think that cum can get 'ripe' like a fruit and that it can also 'go off', like any food. If it hasn't had much time to be created it can be quite fluid, almost transparent. But if it has been too much time between ejaculations it can become thick, gloopy and even a different colour.

Davids' cum was thick, and although I couldn't see it because it was deposited into my mouth, believe me when I say a girl can tell. It was thick, not quite as fresh as it could be, but most of all there was a lot. Even for David, this was a lot.

And it was in my mouth, along with a very erect penis.

I steadied myself a little, keeping David close and his penis three quarters of the way into my mouth. It wasn't deep into my throat, so I could breathe. I just had to concentrate in keeping the cock in my mouth and not removing it.

My natural reaction is to take it out, tongue clean it of cum and show my partner the reward on my tongue. But not this evening. Tonight I had a different role to play, to be like that girl in his pornography fantasy.

I don't know if the performer swallowed the first load from her partner, but in the moment I decided against it. What would I achieve by it? If I couldn't show David the load 'before and after', could I use it to my advantage? I had to keep his penis in my mouth but he said nothing about keeping the cum in my mouth.

Without wasting any time, I got back to sucking his length, deep, more forceful than before, not giving him the opportunity for his cock to become flaccid, to stay on it, for him to keep focussing on me even after his first orgasm.

To David this was new territory. Yes, I'd kept sucking his cock after he had cum in my mouth, but it was usually just to clean him, to lick his cock of spunk slowly whilst he was at his most sensitive.

Now he had a woman, a slut with a mouthful of his cum still going. He could feel it, his cock was covered in his own cum, lubricating the friction of my tight lips as they worked their way up and down his shaft.

There was no chance, no thought of him not being able to continue. And when he looked down he knew there was no prospect of me pulling out. Of tapping out after round one.

Each time his cock touched the back of my throat, I could feel it twitching. His cock was very sensitive now. Perhaps I could take advantage of this and make him cum more quickly than before?

I edged his cock deeper and deeper into my throat, until the force I applied with my arms and head pushing against his resistance made it pass.

Once it has gone into my throat the first time, I knew it would be easier on the next penetration. But still I held it in there. Preventing oxygen getting to me, until I release it and feel the cockhead quickly slide back across my tonsils and back into my mouth.