Emma's Stiletto Seduction Pt. 04

This is a continuing story, please see :

Emma's stiletto seduction

Emma's stiletto seduction Pt. 02

Emma's stiletto seduction Pt. 03

Comments welcome

They'd had sex before, but this was different. They were outside for one, finding themselves in a shelter on the promenade of an English seaside town. It was late, past midnight, with dark skies and still a hint of rain in the air. It threatened more.

A tall middle aged man was standing over his partner. It had been a matter of weeks since he had learned that an average, rather boring work colleague was actually a lifelong transvestite called Emma. He had not planned this, and it was somewhat of a surprise to find he had just been sucked off for the third time in four days.

A small, goth transvestite was sitting quietly. It had only been a matter of weeks after she'd had a dream about an average, rather boring work colleague from accounts. On Wednesday she had made a successful attempt to seduce him. She had just sucked him off for the third time in four days.

I stood up from the bench and wrapped my long black leather jacket around me, having noticed the chill in the night air. I still had cum on my leather skirt, but with nothing to clean it with, it would have to stay there for now at least.

Taking David's hand, I led him from the safety of the shelter and started to retrace our steps back to the detached house he purchased 6 months ago with his wife. It was situated nearly a mile from where we stood and provided us with a focus - I was taking him home.

Breaking the silence, David spoke quietly., "Did we just have a threesome?"

"No!" I said laughing, "Of course not."

"But there was three of us, so that should count?"

"It's not counting, neither of us touched him." I confirmed, "He just cum in his pants!"

"Well I think it's the closest I'll ever come to one, so let me have it." David joked.

"I will think about it." I said, "Let me get back to you."

It was the conversation we needed, it broke the tension. Neither of us had planned to have oral sex on our walk, and it was a surprise to both that we had been closely watched by a voyeur, just as David had given me a 'facial'. Another '1' to be placed somewhere in a cell on his Excel 'sex' spreadsheet.

"You have cum on your face Emma," David said shyly, "just thought you should know."

"So that's what it is." I retorted, as David watched me try and open my right eye. The semen was still clinging to the long hairs of my fake eyelash.

"This is known as a cum-walk," I explained, "a lot of men like to parade their woman when she is covered in cum."

"Like a cat marking its territory?"

"Exactly like that."

I could tell he was interested. Turned on yes, but attentive. He hadn't had any sexual experiences outside of his marriage. Now he knew he was allowed to ask questions and that I was going to respond, I braced myself for another oral barrage.

"You don't have to answer," David started, "what does my cum taste like?"

"A typical man question." I thought to myself.

I took off my right glove and put it in my handbag. Reaching up to my eye, I pinched a globule of cum between the long glossy fingernails of my index finger and thumb.

"Do you want to try it?" I asked, playfully, offering it up to him.

"No!" David replied quickly, "That's your area of expertise I think."

"But how will you ever find out?"

I transferred the cum from my fingers to my lips, and then licked it from them with my tongue. David look on, fascinated.

"It tastes like cum." I answered, "It smells and feels worse than it tastes."

"What do you mean?"

"It doesn't really taste of anything," I explained, "unless you've been eating a lot of fruit, or smoked tobacco."

David shuddered.

"It's more dry, really dry though," I offered, "the salts leave your mouth feeling like you have a bad sore throat if you don't drink anything afterwards."

David nodded.

"It's not the worst tasting thing to come out of a cock."

It was like David was making notes. He had never asked anyone questions like this before, certainly not his wife. Not even as they first started dating when they were 20. He was embarrassed that after 55 years he didn't actually know what his own sperm tasted like or much about sex at all.

I had led a different life to David. Ever since I knew what sex was and how to make myself orgasm I had sampled my own sperm. Cross dressing came first, definitely, and my obsession with cock and cum followed afterwards.

As a teenager I knew I wanted to taste cum, to drink it. Unfortunately it just wasn't that straightforward to come by. So I, like lots of trans girls, practiced on my own fluids. It started by just rubbing my own cum onto my lips after an orgasm and then progressing to taking it in my mouth. It wasn't easy. The desire was there each and every time, but the instantaneous down you feel after orgasm usually crushes this and makes swallowing a mouthful of your own cum very difficult indeed.

"And that's why," I continued to explain to David, "It's better to taste someone else's cum rather than your own."

David had one more question, one that he had wanted to ask since he had first seen pictures of Emma a few short weeks ago.

He plucked up the courage whilst walking along the dark pavement, the clicks of my heels matching the strong beats of his heart against his chest.

"Just ask." He told himself. "Do it."

It was out of character, he couldn't believe the words he was about to say, but say it he did.

"Have you ever had anal sex?"

"David!" I exclaimed, turning to face him with my mouth open in feigned shock.

"Yes, I like to be airtight."

"?"

"One in both holes."

And that was enough for him. We had already taken huge strides in our relationship this evening, anything else could wait for another day.

It was late when the Uber cab I had taken from Davids' house pulled up in front of my apartment block. Thankfully a potentially awkward cab ride had remained silent. I left the driver a 5 star rating.

I woke to find that I was still wearing my lingerie as I pulled back the duvet and, by the look of my pillows, my make up too.

"Thank goodness it was a Sunday." I thought to myself.

It had felt good to remove my boots, I recalled when arriving home in the early hours, but was too tired to completely undress. Even though the stiletto heels were much lower than I was used to, the thin soles had transferred the sharpness of every stray pavement stone directly into my feet.

I dragged myself into the bathroom, reached into the shower cubicle and turned the dial fully clockwise. The cold water splashed against my skin, it would take a minute to get hot.

I took a towel from the airing cupboard and threw it on the bathroom floor, still exhausted. I stepped into the cubicle and felt the hot water rush over me. It quickly soaked my black basque, that with 4 suspender straps still managed to hold up my stockings. They felt increasingly heavy as they soaked in the hot water.

I cupped my hands and splashed water over my face. It felt waxy as the heavy foundation became liquid again and left a pink streak on the tiles as it ran into the drain. It took ten minutes for me to start feeling human again, and for my mind to begin to wander over the events of the previous evening.

I'd sucked off David in front of a complete stranger.

I'd taken a cum facial.

I'd done the cumwalk of shame.

As I tightened my grip on the shower scrunchie, a flow of soap suds fell onto my stockings. I cringed a little, and hoped that David was ok. Had I thrown it all away, did we go too far to soon?

David had walked me to the Uber cab at 1am. He watched it disappear from view and thought carefully about the evening, his heart still racing, nerves on fire. It was pointless even thinking about sleeping like this. Instead of turning towards home, he started to walk in the opposite direction.

He traced his steps to the point where he and I had first met the strange man walking towards us on the pavement.

"It was here," he thought to himself, "that the man groped her arse!"

David couldn't blame the man, he had done the same earlier when he was kissing me, but at least he had obtained my permission. He decided that one of his favourite things was kissing me, especially when I held him around his neck and he had a hand on each of my leather-clad bottom cheeks.

David walked on.

"It was here where I kissed her again under this very lamp," David reminisced, "and she actually wanked me as we snogged."

And there it was, the shelter. "An hour ago Emma had given me a blowjob," David thought excitedly, "it probably still has my cum on the seats."

But like then, he was surprised to find he wasn't alone. Sitting in the shelter was the outline of a man. Was it the same man, a voyeur who watched him having sex earlier? David was determined to find out.

As he approached, he recognised the back jeans and jacket of the man who had quickly made his exit.

"Hey," he found himself shouting, "it was you, wasn't it?"

"Me what?" Said the man.

"You watched us earlier."

The unknown man paused, not yet deciding on accepting or denying his behaviour.

"........"

"Yes." The man admitted, "Sorry I. I just couldn't help myself."

"Well.."

"Mate, you lasted longer than I did anyway." He said, embarrassed.

"Oh yes." David replied, "I had already cum before. That was probably the reason." David said, laughing to himself.

"You lucky git," the stranger replied, "She must be great fun."

"She's a slut." David said quickly, before he had time to take his words back. He didn't want to talk about me like this, but he felt his bravado and masculinity rising, taking over his mind. He had never spoke about women like this before. He had never had sex like this before.

The stranger nodded his agreement.

"And that outfit, those boots..."

"She does love Leather," David interrupted, "and sucking cock."

"Look," the stranger said, "If you two ever want a repeat with her... no strings... I can give you my number."

David was taken aback. He had never discussed me with anyone before, let alone another man who had just watched him have sex. The stranger held up his phone, with his number glowing brightly in the darkness. David copied it into his phone.

"I'm Howard by the way," the stranger said.

"Dave." Said David, never having previously referred to himself in that way before.

As he turned away from Howard, David said, "She is trans you know, Emma. She is really quite sweet."

And walked off into the night.

I poured myself a cup of coffee in the office first thing Monday morning and sat back at my desk.

I had exchanged a few texts with David yesterday, concerned that I had got home safely and that I had picked my car up ok later that afternoon. Nothing was mentioned about the events of our second date. Just thinking about those words, things had moved rather quickly in the space of a few days. I put everything out of my mind and concentrated on paperwork until it was time for lunch, which I took in the large glass atrium on site as it was finally a sunny day.

Of course David was there, sitting at a large table with colleagues from accounts. I walked past, in drab of course, but unavoidably he noticed. His eyes followed me to the first floor balcony, where I sat and unpacked a chicken salad and bottle of water from my bag. I could see his table, and that he was looking up at me.

My phone beeped.

David: Hi Em x

Emma: Hi David xx

David: It's a boring meeting x

Emma: it's ok, you don't have to come over x

David: I will NOT thank you for Saturday x

Emma: You are learning x

David: You were very greedy! ;) x

Emma: Oh look at you with your sext'ing in-front of your colleagues :) x

David: It's your bad influence cc

Emma: I just encouraged you! X

Emma: It turns you on to talk sex in front of people doesn't it x

David: no comment x

Emma: What's the dirtiest thing you can text me? :) c

David: Are you sure you want to know? X

Emma: Yes sir x

David: I want to bend you over, pull your panties down and fuck the arse off you! X

.....( 2 minutes pass)

He glances up at me....

Emma: OK, how about Wednesday evening? X

David: Are you serious Em? X

Emma: My place, 7.34pm x

David: see you then! X

Some guys love the fact that I'm really into sucking cock. It's usually what they cannot get from their wife or girlfriend and therefore what they want more than anything. For others, who get blowjobs, it's anal sex. The opportunity to bend me over and really 'fuck the slut', that's their priority.

For David, who I was absolutely sure that he had never had anal sex before, we were about to find out what he really wants from sex.

David kept staring at his phone. His lunch meeting with staff from accounts had ended five minutes ago. He re-read the texts that he had just sent. This didn't help with his erection that he found himself trying to hide.

"Go down for goodness sake!" He thought silently to himself.

But the more he tried not to think about me, the less likely he was going to leave the table without a tent-pole in his trousers.

"How embarrassing," he acknowledged, "I'm 55 for goodness sake."

It had been a while since I last had a cock inside me anally, but I was glad that the next one would be Davids'. I didn't want him to get bored with what we had together, so our third date on Wednesday would be ideal to advance things to the next level.

"I have to remember that I don't have a pussy for them to fill, so it has to be straight on to anal." I learned from a young age.

I arrived home from work that evening, skipping dinner and heading straight for the bath. It would be a good opportunity to relax, to tidy myself up. And to practice.

If you have never had a penis up your bottom, well, it is a trickier thing that you can imagine. It can hurt and, if the man is not careful or he is just too big to be up there in the first place, it can really hurt.

I needed to reassure myself that it would be ok, I didn't want David's first experience of sitting his 'A-Levels' to be a bad one, and I so wanted our liaisons to continue. I still really fancied him, in fact after our second date, I fancied him something rotten.

"Best start with the smallest dido and work my way up," I thought to myself, "don't go too big too soon."

Davids' mind had been racing, it proved utterly impossible for him to work through the afternoon. As soon it was possible to escape the office he did so, taking the longest route home to try and occupy his mind.

The weather continued to be a typical British Autumn, warm sometimes, always the chance of rain. It kept David out of the garden, he was caged indoors and trapped with his thoughts. His daydreams always seemed to meet back at the same point, bending his girlfriend Emma over and fucking her hole as hard as he could for as long as he could.

The fact that he already thought of her as his girlfriend both alarmed and thrilled him in equal measure.

He fared no better in the evening, unable to finish his supper, stomach in knots. He was in an almost permanent state of arousal now. Always erect, always thinking about sex. More than he ever had in the last 20 years combined. He desperately wanted to contact me, talk to me, and found himself sat in bed bolt upright staring at his phone.

He composed a message:

David: Hi Emma, I want you. X (Deleted)

David: My cock needs you x (Deleted)

David: Emma, (Deleted)

He flicked through his contact list, and selected another.

David: Howard it's Dave. I'm seeing Emma this week. Do you still want me to pass the message on, after what I told you?

He regretted sending it as soon as it left his phone.

"Why on earth," he muttered in a moment of clarity, "now that was stupid."

The truth was that he didn't plan on telling me about Howard. That they had met by accident again that night, and that he had obtained the strangers mobile number. The very last thing that he wanted was to share me. He could feel a jealous rage well up inside him at just the thought of it. And yet he could think of precisely nothing else.

His phone alerted him.

Howard: Thanks Dave, if you could. I don't mind the trans thing, she looked great! A real slut.

David hoped that the reply was going to be different. That the thought of me being trans would have put Howard off. And more importantly he could have me to himself. David could just stop texting, or block the number and easily hide all of this.

He didn't know if it was some strange sense of duty, or the product of an overactive sexual imagination, but found himself compelled to respond.

David: Yes, she's a fucking slut.

And he then knew why. He wanted to tell someone, to shout that he had me. He had never had anything previously to brag about. And talking dirty, about his girlfriend, thrilled him.

Howard: Fucking hell. You cum in her face!

David: She'd had a load of cum before that happened.

Howard: I couldn't believe it. I thought she was going to have mine too!

David: So did I for a minute.

Howard: I should have fed her, then fucked her cunt

David: yes. Spit roasted the bitch.

Howard: Fucking ruined her!

David: Get her airtight.

It took all of David's will not to wank when looking at the texts from Howard.

"I'm going to save my cum for Emma." He thought, "She says she wants it, so she will get it."

And his explicit text conversation with Howard continued late into the night.

For the first time in a week, I slept soundly, completely oblivious that two men were getting off discussing me in intimate detail.

I knew I was prepared for my third date with David. I hadn't got to worry anymore about whether he fancied me or not, he clearly did. In fact I thought that he had developed more than a crush right back at me.

Instead of nerves and worry, my day passed uneventfully, with a dash of excitement. I knew what was happening and exactly who it was going to be with. And after all, I was already very well acquainted with the cock that was going to have me.

I hoped that David would appreciate my outfit. I knew he liked goth women and had been encouraged by what previous lovers had christened my 'leather fetish'.

This time, I chose my prettiest black bra, size 32b. It was padded, and would push up my small but growing breasts into a realistic handful. Without a basque this time, I clipped a thin black lace suspender belt around my waist. It had four fastenings for stockings. Whilst perching on the armchair next to my bed, I rolled on a pair of seamed nylons. They had a high denier and were nearly opaque, but the thick ribbed seam stood out and traced a line from my ankles to my stocking tops. It would be clearly visible to anyone behind me. I secretly hoped David would be encouraged by this.

I chose a white cotton blouse from my wardrobe, it was sufficiently tight to cling against my breasts providing shapely curves to my small formless body.

I would usually wear a dress or knee length skirt, but it would be awkward for the evenings menu of activities. I had to choose something more practical for tonight. I chose a back leather miniskirt from my wardrobe and I unclipped it from the hanger. It had a high slit on both sides, and was short enough to reveal an inch of skin above the lace tops of my stockings.

I did my make-up in the usual way. Dark eyes with lots of eye-liner and mascara. Full red lips. I chose to wear my glossy jet black shoulder-length hair in a ponytail. I knew that David loved the bobbed look but tonight was going to be different. I could always take out the band and let my hair down if necessary. I completed the look with a pair of large hooped earrings, 4 inches in diameter. The weight of the metal straining my ears.