Emma's Stiletto Seduction Pt. 04

I took out a pair of 4" patent leather ankle-strap stiletto heels from my closet and placed them on the first step of the staircase.

My mobile phone received a message.

David: On my way, will be with you shortly. X

Emma: Great x

On a silver tray in the kitchen I had readied the following items:

100ml tube of water based lubricant

4 Durex lubricated condoms

Small box of unscented tissues

A white ceramic dish, 4" in diameter

A dark dry flannel

I looked at the clock, 7,25pm. 9 minutes until David arrived. Just enough time to go to the bathroom, I had prepared a surprise for my date.

7.30pm

I sat on the second stair, slipped on my high heeled shoes and bucked the ankle straps tightly. The advantage of straps is that they are easier to walk in, and cannot slip off by accident. I was locked in to them whatever happened this evening.

David was curious as to why I'd chosen such a time to meet. "Was she testing me," he thought to himself? But it didn't matter. He had parked his car a suitable distance away, and timed his walk so that he was three minutes away.

I watched the last digit on my mobile phone change from a 3 to a 4. The intercom of the flats gave a deep 'bzzz' as David pressed my number.

I lifted the received and instantly released the catch of the front door. He was on his way up to the first floor.

Over the years I had waited for many men to climb the stairs and through the passageway to my door. David was different. He was the only person that I had fancied. That I wanted. All the others were just sex. An itch to scratch. And yet as much as I thought David and I were different, here we were on nothing more than a booty call.

I watched through the spyglass as he adjusted his tie and smoothed his hair forward. Straightening his cuffs so that his white shirt showed slightly beyond the sleeve of his suit-jacket. He reached and knocked the door.

"Here we go," I whispered to myself, not really knowing how it actually would go.

"Hi Miss Emma," Said David, walking past me into the hallway, "You look great as ever!"

"Thank you sir" I replied in my customary riposte. "Do come though.

Once again David waited for me to walk first, and his eyes immediately noticed the seams in my stockings even though I had set the lounge lighting to be low.

"You have a ponytail." David said.

"If you don't like it, I can take it down," I replied, "I thought it may come in useful."

Not standing on ceremony I walked over to him, and wrapped my hand around his neck. I kissed him this time, pushing my tongue between his lips forcefully, creating a wet lipstick fuelled snog. Of course his hands found my bottom, and lifted up the back of my skirt so that he was groping my flesh in his strong hands.

"Do you still want to fuck me?" I asked quietly in his ear.

"Oh God yes". He quickly responded.

As it was his first time, I knew that I would have to at least take part of the lead this evening. His naivety was sweet at times, but this was an occasion that I would allow myself to give him direction.

Getting him in the mood wasn't going to be a problem. I could already feel him grinding his body against my own as we continued to kiss. In the four days since I last serviced his cock, it appeared that he had been saving things up for this evening.

"Are you full of cum?" I whispered

"Yes." Panted David, "I want to give it to you."

Davids' tongue was out of his mouth, I had my lips pursed around it and was sucking it like an engorged clit. I released it and stepped back, dropping his hand as I went into the Kitchen.

"Where are you going?"

"Back in a minute."

I took the silver tray from the kitchen and placed it onto a side table next to my green leather Chesterfield in the lounge. David looked quizzically at me.

"Condoms and lube." I confirmed, casually.

He was silent.

"Ok here is what we are going to do." I announced. David seemed unable to contradict this.

"You are going to help me strip you naked."

David nodded.

"We are going to get you nice and hard."

Again, David nodded.

"I will put a condom on you, and wipe your cock with this water-based gel."

David started to pay more attention now.

"It will feel cold, but will soon warm up." I added, "Then I'm going to bend over the sofa and you can enter me."

"And then what?" David replied, nervously.

"Well then you can do what comes naturally." I suggested, and smiled.

Before I'd finished talking he was removing his jacket and throwing it over a chair.

"What have I let myself in for?" I thought to myself.

In the 20 years that I've been having sex with men, I have tried my best to avoid first-timers. I didn't really see myself as much of a teacher, and its hard to be submissive when you have to tell people what to do and where to stick things.

I have had conversations with lovely guys, who then revealed they haven't been with a tranny before, or hadn't yet performed anal sex. It seems horrible of me now, but it usually resulted in a 'Thanks but no thanks.', or the dreaded 'It's not you it's me." Brush off.

Perhaps the worst thing to do for the first time with a guy is water-sports. Men are typically full of bravado, "You want me to piss on you? Sure, where do you want it love?" But of course their mind may be willing, but their bodies invariably reject this idea. It's actually very difficult for a guy to piss on a woman. It just feels wrong for them and if they haven't performed before, then you can find yourself kneeling in a bathtub waiting for a stream of urine to hit you and nothing ever arrives.

I hoped David didn't feel the same about penetrating my bottom, as it was something that was going to be important in our future relationship.

David didn't need my help undressing, he took off his briefs and his cock was hard and pointing at the ceiling. "That doesn't need much help neither." I thought to myself.

This was the first time that I had seen David naked. His body was exactly as I'd imagined and fantasised about. He was tall and strong, but still looked like his body was comfortable. His belly was big and his legs stocky too, his broad shoulders framing him well for his age. I noticed that his testicles hung low, exaggerated no doubt by his rock hard erection.

"Come here." He suggested, and I walked over to him, talking his shaft in one hand and cupping his balls tightly in my other palm.

"Are you going to fuck me, David?" I asked, looking up at him and maintaining eye contact. I started to wank him.

"I'm going to fuck you Emma." He said nervously.

With one hand still on his cock, I reached over to the side table and took a condom packet. I tore at a corner with my teething and a lubricated condom was squeezed from the foil.

I got on my knees, and sucked his cock deeply, as hard as I could.

"Fuck Em!" David cried out, and I hoped that I had't tipped him over the edge already.

Taking the tip of the condom in my fingers, carefully avoiding piercing the latex with my fingernails, I placed it on the tip of his glans. It was large, the biggest I had ever seen it, engorged with his blood. I took the condom between my fingers and rolled it down his shaft.

Still on my knees, I reached for the tube of lubricant. I emptied a pea-sized droplet of gel onto the tip. David did not flinch, but watched intensively as I coated his cock with lube, taking care to rub my thumb across the ridge of the bell end to keep it excited and erect. I rocked back to my heels, and wiped my hands on the flannel.

"Look, I need to be fucked right now." I demanded as I walked over to the sofa.

I bent over the wide green leather armrest, and lifted up the back of my tiny black leather skirt. David gazed down, as he viewed my suspender belt and stocking tops for the first time this evening. He could feel his cock twitch in excitement.

He walked over to me, and placed his hands on the small of my back.

"Take my plug out." I suggested.

David hadn't seen a butt plug before outside of porn, and yet here he was staring right at one. An inch of which extruded from my hole against a flange preventing it from penetrating deeper inside, me.

"Just pull it." I instructed.

It was softer than David had imagined it to be. It was silicone, not hard plastic, and as he griped it with his fingers he found could squash it a little to get purchase. It was also tighter than he imagined. It took a continuation of pressure to tug it free, but when it did so it slipped out quickly and smoothly, covered in a layer of thick lube.

"Put it in the dish." I suggested, and David did so.

"Ok". He said, staring at the hole that had replaced the plug in his view.

David had never seen a bum-hole before. He was embarrassed by this, he cant see his own and his wife would never have allowed him to look at hers let alone put his penis inside it.

He looked down at me, my arms now reaching behind, holding my cheeks wide and presenting myself on a plate to him.

"The sight was to be remembered." David thought, and had forgotten that my hole would be framed by the heavy straps of my suspender belt and the soft lace stocking tops of my nylons.

The hole looked small, too small as he gripped the shaft of his dick and looked down at his cockhead.

"Is that really going to get in there?" He thought.

"OK try and put it in me." I encouraged, feeling like a sex education teacher, or narrating a government guide to anal sex. "Charley says put your cock in her ass and fuck her."

I felt the tip of David's cock against the circumference of my hole. He tried to push it in.

"Oh shit," David Thought, "how can I get it in there?"

When most people see anal sex, it's usually part of a porn video. They see girls, and trans girls, easily able to take the monster cock of the porn starts surrounding them. Even a massive dildo or the fist of another tiny woman. But that's not how it works in reality. Those women have trained themselves up over months and sometimes years to do that. It should be an Olympic event. For most people, anal sex isn't as regular as it should be. I had't had anal for a couple of years and my bottom was as tight as it's even been.

I reached back and adjusted my bottom again, helping to present my hole at a better angle.

"Push my plug back in a few times," I suggested, "get a feel of it".

David did so. He placed smaller tip of the plug against my hole and, with a bit of force, the anus spring open and swallowed the 3 inches easily.

"You just have to get it past the first hurdle." I instructed, "See?"

David laughed.

Here we were trying to have serious sex, but but you have to sometimes laugh at the ridiculousness of it all.

I felt my bum react to the plug, and the muscles tightened and ejected it swiftly into David's hand.

He pushed it in again, and found that he knew the pressure required better now. It went in easier this time, and pulled it out himself, making note of the slight indentation in its diameter that kept it in when inserted beyond the sphincter.

"This needed a lesson in human anatomy first." He thought to himself.

After 30 seconds of David inserting and removing the plug from my bottom, he would try again with his own cock.

He applied a drop of lube to the tip of his cock and worked it down the length of his shaft, wanking it hard to make sure it kept its erection.

Once more I felt the warm tip of he cock against my hole, a different sensation to the silicone of the plug that had just fucked me.

David held his cock straight and firm, and slowly applied pressure to my anus. I could feel it starting to give in, and moaned audibly.

And then it happened. As the tip worked its way passed my muscle the length of his cock slipped in.

"Oh!" I exclaimed, arching my back as I felt it enter me.

David had a different sensation. It was unlike anything he had experienced before. It was warmer and softer than he imagined. In fact, he could never have imagined this. It was noticeable how strongly his shaft was being gripped. It was like a fist had wrapped its knuckles tightly around him.

He started to move it gently. It glided in an out, thankful for the lubricant reducing the friction that my bottom had on his cock.

Slowly he started to fuck me.

As he got into his rhythm, he started to relax. he was excited by having his first anal sex yes, but also at the reaction I was having to his cock. He had never heard me moan and sigh, or talk dirty to him whilst I had blown his cock.

But now he could see, and instantly feel my reaction to every thrust.

As he started to fuck, I could feel nearly his whole length bury itself deep into me, until he pulled out too far...

The muscles of my bottom quickly rejected his cock, and it was free again.

"Sorry. Sorry." David apologised, realising that if he withdrew it too much it would come out, just as the dildo had.

He rested the cockhead back on my anus and dripped a fresh bead of lube onto the tip. Holding the condom tightly against the base of his penis, he pushed it back into me. I could feel him getting more confident.

Now he was fucking me, really fucking me, and I pushed my bottom back to meet the deepness of his stroke, feeling his balls slap against my skin.

Not needing his hands to steady his cock anymore, he grabbed my hips. Keeping it deep inside and only moving it back two or three inches with each stroke was best. It was easier to keep his cock in me, and could slam his hips against mine. he watched as my large hooped earrings were made to dance from his thrusts.

My pristine white blouse was now damp with sweat. I unbuttoned it and threw it to the floor, showing him my bare skin for the first time.

His hands reached to my bra, and used it like reins to make me arch my back into him. He grabbed my tits from behind, my weight rocking back to my high heels, and started to nuzzle and bite my neck.

Trying not to make too much noise, I bit my bottom lip as the rhythmic slap of his skin against my bottom filled my apartment with noise.

His hands wandered to my ponytail, a trail of sweat leaking from my hairline into the small of my back. He grasped my hair tightly, now understanding why I had worn it this way. His other hand was around my exposed throat, holding it, even slightly wanking it as if it were the shaft of a cock.

He pushed his thumb into my mouth, which I greedily sucked, and he hooked my cheek with his index finger.

"Where had he got this from?" I thought to myself. But I knew the answer. "Porn".

"You are fucking me like a pornstar!" I exclaimed.

He pushed me forward onto the arm of the sofa again, and retracted his cock trying to keep the tip in. He confidently added more lube, smoothed it around his shaft and buried it deeply into my arse again.

He wanted to cum. He was about to cum.

"Should I cum up her?" He quickly thought to himself.

But it was too late, he was past the point of no return. He was going to cum now no matter what.

To David this was the best thing about sex. The all too brief moment when your body switched to automatic. All the decisions were taken from you. Autopilot mode activated.

But this time the feeling wasn't instant. He was past the point but still he kept fucking. The tight grip my bottom had on his cock delaying his orgasm until.....

One stroke

Two strokes

Three strokes

Four strokes

With each thrust, he could feel the moment getting closer, could he manage another one.....

Five strokes.

He held it balls deep, the deepest he could get it and pulled me back on to him with my bra strap.

And he came.

The rush of his orgasm filled his entire body, for the first time he physically jerked when the rush of cum flowed from his full balls and out of his tip.

He became almost bent over, his chest against my back, as he squirted another jet of cum into the condom buried deep in my anus.

He could only hold himself there, he felt like his legs may no longer support him if he let go.

He could hear me panting now, realising that he hadn't been noticing it, or the rest of his surroundings, for a few minutes.

He stood up, still inside me, and reached down to his cock to keep the condom in place. I took an intake of breath as he withdrew his hot cock from my bum. It remained open, the muscles not yet ready to close just yet.

He was hesitant to look down, but he did. He could see the condom full of his cum, filling the tip and covering the deep purple bell with white jizz.

"Wow." I said, resting my elbow on he back of the sofa and looking back to him.

He couldn't speak. Just standing there, naked only for the full condom on his cock.

"Are you waiting for something?" I asked.

"No. No." He stuttered, gathering his thoughts.

I stood up from the sofa, and faced him, pulling my skirt down from my waist.

He looked down to my tits in my bra, and back up to my eyes.

I sunk to my knees.

"You don't", He gasped, "Emma you..."

But it was too late. I had squeezed the tip of the condom emptying the cum back onto his glans. As I removed it, I held my fingers so that it emptied the condom along the length of his shaft. It dropped to the floor.

He looked down to me, knowing what was next.

"Are you sure?"

"Yes" I said smiling, "I'm sure."