Emma's Stiletto Seduction Pt. 12

Emma's Stiletto Seduction Pt. 012

Trans Emma is shared with a mechanic

This is a continuing story, please see :

Emma's stiletto seduction 01 to Pt. 11

Comments welcome.

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He milked out a droplet of sperm from his cock and flicked it on my face, hitting my cheek.

Still in silence, he put his penis back into his trousers. I kept my kneeling position, with my hands resting palm down on my thighs. He eventually offered me a hand.

I took it, and with David's help rocked back on my heels to stand again.

"Don't swallow." David said. "Don't lick your lips."

"Yes sir."

"Do you like cum on your face?"

"Yes, I love cum on my face."

"Are you a slut?"

"Yes, I'm a cumslut."

"Then drink it." Said David. "All of it."

It had been an interesting evening to say the least. On the last night of our first trip away, I had spent the prior hour having sex with my boyfriends work colleague.

When we had experimented with threesomes early on in our relationship it had been a disaster. The third man was rough with me, a stranger too, and David had hated this. But the earlier events of this evening had been different. David had trusted his old friend, Richard, not to hurt me. He also felt that it would be beneficial for Richard to have sex, to have company, to take away some of the loneliness that a marriage break up could inflict on a man. David knew that if it wasn't for dating me and our relationship together, it could so easily have been him feeling these things.

In the days following the trip, life went back to normal. Richard was far away up north, so David knew that nothing further would be happening behind his back, not that he thought I would do that to him. David knew that I had only been with Richard at his own suggestion, on his orders, and insistence. If I had actually enjoyed the encounter was of no consequence.

"She is dating me," David repeated to himself whilst sat back at his office desk on Monday, "she wants to be with me."

He felt like he could cope better with situations like this now.

I did my best to relieve any anxiety or jealousy that my boyfriend could be feeling, by being more attentive and caring. It was also a shrewd move not mentioning the subject. At all.

For the next few weeks we had settled back into our now familiar routine. We would ignore each other at work whenever our paths crossed, but continue to exchange flirty and sexy text messages until one of us invited the other over of a Friday or Saturday night. It usually involved me staying over at David's house rather than my flat as things were more comfortable there.

It was approaching a year since Davids' ex-wife had left the house, and him also. She had left because of the pressures of spending more time together during the lockdowns of Covid, and had gone to stay with her sister for a 'few days'. She never returned.

For her the marriage had long since ended, but they had stayed together due to convenience and laziness on both of their parts. I considered her loss as my gain, as David was certainly still a catch and our relationship had developed into the best one I had ever had.

It was never going to be conventional. The traditional tale of a white middle aged man who had only ever been with his wife, is suddenly introduced to a life of sex and debauchery by a middle-aged transvestite. It will never be made into a Disney movie.

Even though David had never thought that this could ever happen to him, he was glad that it did and he felt lucky that he could at last experience what a great sex-life could be before it was too late.

He knew that there would have to be compromises in his new relationship though, and that our sex lives were compatible but only up to a point. He knew from the offset that I liked sex, and that having to share me, certainly in terms of having sex with more than one person, was something he would have to learn to live with if we were going to become long-term partners.

Him sharing me with Richard a few weeks ago had reassured him that we could carry on and move forward in our life and still be together. It wouldn't affect our own relationship, which is what he had feared most. David knew I wouldn't cheat on him, but I would sleep with other men if he asked me to.

He figured that it had some positives. His girlfriend would never cheat on him, I would have no need to.

He hadn't worked out the frequency of the 'other men' happening in his mind, but he knew he wouldn't want it to be every other night. He figured that once a month would be enough for me to scratch an itch and to hopefully keep things fresh in our own relationship.

It was during a regular Friday night date at Davids' house that he knew it was time for his girlfriend to meet someone else. He had thought things over in his mind and came up with a fantasy for me that he wanted me to act on, it was just finding the appropriate opportunity to bring up the suggestion.

Apparently the most appropriate time to start the conversation was when he had bent me over his dining room table, and had his cock buried deep into my hole.

He was still dressed for the date, still wearing his formal shirt, tie and polished shoes but had allowed his unbuttoned trousers to fall down a little from his bottom. The rhythmic action of his hips were the direct cause.

I was showing my bare ass, black panties pulled aside and skirt riding above my waist revealing my stocking tops.

He pushed his cock in deeper to my bottom, he always liked the way it gripped his shaft tightly, and was able to swallow it all balls deep if he positioned himself in the right place.

To me, even though I was small person, taking a long cock anally had never been a problem. It was always the girth and expanding my hole to accommodate it that was the main hurdle. Once he had forced his bell end through my anus, he was free to push it deeper - and he did so. Repeatedly.

Steadying himself with his hands on my hips, my legs shaking due to being on the toe tips of my high heeled stiletto shoes, David could feel himself about to empty his balls inside me.

"I'm going to cum." David muttered under his panting breath.

I gripped the sides of the table top tightly, as I knew the last thrusts he would give before he orgasmed would be uncontrolled. David was in his fifty's, but he was still a strong and powerful man at 6ft 3 and he could certainly move my small body with ease when he wanted to.

His thrusts stopped, his cock buried deeply, and I sensed it twitching as his spunk rushed from his balls and squirt from his cock into the tip of the condom we were using.

For me, a man orgasming in my ass was just for them. I couldn't feel the warm cum fill me, as it was contained within the latex.

"Perhaps one day we could do this without a condom?" I though to myself, and I was sure that David was thinking along similar lines too as he looked down to see if it was still in place in his penis. It was.

I thought that David was still apologetic when cumming on or in me, even though by now we had done this more times than he had sex with his wife during decades of their marriage.

He pulled his trousers back to his waist, and rested his hands back on my hips, hooking a thumb under each tight suspender of my basque. The gusset of my panties rested against his shaft.

I pushed myself up from the table and straightened. Even when I was in 4" heels David still towered above me, and I reached up to touch him. He pulled my ponytail to one side and kissed my neck gently from behind.

"Thank you." I said giggling to myself, knowing that I had banned him from thanking me or apologising for cumming when we had sex.

David smiled.

He was feeling reassured, and in control once more. After all there was no faking what we had just done and experienced together, and the signs of affection that we had shared afterwards. We were very much a couple and very much together.

Whether it was or not, to David this seemed like the ideal opportunity to bring up the subject we had not mentioned for a while now.

"Did I tell you," Said David casually, "I need to get the oil changed in my car."

"Oh." I replied, being caught completely off guard. Most unexpected in the current circumstances as his penis was still currently inside me.

I had noticed that he hadn't yet removed it, that it was still hard, and getting harder...

"I'd like you to take it to the garage tomorrow to have it changed." David asked, "Would that be ok?"

"Yes, I don't mind coming with you." I replied, not too sure where the conversation was heading, adjusting myself slightly.

"I was thinking you could go alone." Said David innocently, "And try and get a discount."

Suddenly I understood, that this was an opportunity to have sex rather than just run an errand for my boyfriend.

"I have arranged eleven-thirty tomorrow," Said David, "A small garage on the A271."

"Are you sure you are not going to come with me?" I asked.

"Drop me off At Geo's Coffee place on the way." David suggested, "And pick me up when you are done."

It was certainly quite the conversation to be having, and it had not escaped my attention that I was still being penetrated by my boyfriends cock whilst it was being had.

I felt him give one last thrust, as if to put a full stop on both the conversation and the situation. He reached down and secured the condom to his cock as he pulled it out from me. The tip was full of sperm, David had definitely not been wanking during the week.

I turned around and reached up with my arms, linking my fingers behind his neck. He pulled me close and kissed me properly, the remains of my lipstick being transferred to his lips. He definitely liked tasting them. As he kissed me, my hands found his cock, the first time I had touched it this evening, and held it tightly as I slid the condom from it. I gently wanked his cum covered cock as we continued to kiss, both our minds racing about the possibilities that tomorrow may bring.

I had thought that David and I were going to spend Saturday together, so luckily I had packed my over night bag accordingly and had choices of an appropriate outfit for the upcoming occasion.

Neither of us slept well, and it felt like gone midnight until we both stopped pretending we were asleep and began the real thing. Hearts and minds racing, anticipation is often better than the real experience.

I had managed to gain some more information from David though, thankfully it was a small garage recommended to him by a friend a year or so ago. He had used it once prior.

It was an old fashioned small family garage built on the rear yard of a Victorian house, that was now used as the main reception. If you could actually call it that, and a kitchen/ bathroom area. The upstairs was used for storage. I felt better and more relaxed having found it on Google Street View.

in the morning I was up earlier than David, and spent time in the bath trying to make myself look at presentable as possible. As I get older, I have found myself taking more and more time to get ready. It is true of transvestites like myself and of all women.

My nerves were fraught. This was not just meeting a guy for sex, an arrangement, this was another seduction. He didn't know about me, and may not be up for being seduced by a woman like me. I trusted David had chosen wisely, and that he wouldn't be far away if things didn't work out. There would be an element of risk.

David had been late rising, and as he got out of the shower I asked him how I should dress for the occasion.

"Do you think skirt, dress or leggings?" I asked him.

He held his hands to his chin in thought, but was silent.

"High-heel stilettos or boots?"

As he watched me pull on a pair of high denier black stockings and attached them to my basque, he responded.

"Can you wear your black leather knee length skirt, and your kitten heel knee-boots?"

"Are you asking me or telling me?"

"I'm telling you, Emma."

I took a skirt from the built-in wardrobe that I was now sharing with David. My skirt was lined with polyester and heavy, but the leather was soft and supple. I eased it up over my hips and turned to David for assistance in zipping up the full length silver fastener at the rear. He did so and smoothed it down over my bottom.

"Men cannot resist my bottom in a tight leather skirt." I thought to myself, "David had made a strong choice.

I sat on the edge of the bed and pulled on my kitten-keeled leather knee boots. They were quite stylish, again with a back zip and a small 3" stiletto kitten heel. They were very comfortable to walk in and wear all day if necessary, but made the popping and scraping sound of heels that seemed to attract so much attention from the many sexually frustrated men I had met

"Shall I just wear my basque?" I asked, mischievously?"

"No." David said quickly, and then thought.

He reached into the wardrobe and picked out a white satin blouse and took it off the hanger.

I turned my back to him and he hooked my arms though the sleeves and buttoned the front. I tucked it into my skirt.

David Nodded in approval.

"I wouldn't be able to resist." David thought to himself, and then tried to forget what his mind was imagining his girlfriend might be doing with a stranger in an hour.

We had both decided to skip breakfast, I felt too nervous to keep things down and didn't want to spoil my make up and lipstick that I had carefully applied.

I had painted my fingernails a gloss black for our date the previous night, and thankfully they didn't require much touching up. I kept my makeup simple, a light powder and bright lipstick of cherry red. Older guys seemed to prefer this rather than heavy goth make-up I was used to applying.

I still applied my long fake eyelashes and dark eyeshadow and liner, some habits are difficult to stop.

I had styled my hair back in a long ponytail, which showed off my 3" silver hooped earrings that tugged heavily on my ears.

"Coming?' David shouted upstairs from the main hall.

After we had listened to a night of heavy rain, the morning was bright and the sun warmed the air.

He passed my handbag to me and shut the door behind us, I wouldn't need my coat, and the complete full-length leather look was not to everyone's taste.

"Shall I drive?" I asked.

"Just this once." Said David, nodding and handing me the key.

It was a car that was much larger than I was used to, and it took some time to adjust the seats and mirrors to suit me. The seat didn't really come far enough forward to suit my small frame, it was clearly built for men like David and it forced me to sit upright and peer over the steering wheel.

Thankfully my 3" heels did not hinder me using the pedals, I was used to driving a much smaller car in higher 6 inch stilettos.

David had programmed the location of the cafe and the garage into the sat nav, which said '28 minutes' in current traffic conditions. I would be on time, but only just if we had a clear run.

The time stress seemed to help, as it gave us something to think about. We hadn't really talked much about what I should do and how I should approach things, only that if I wanted to try and decide to seduce the owner of the garage, I could do.

David had told me that the proprietor was an older guy, perhaps in his early 60s and had run the garage there for the last 35 years.

"I think he was married, by not anymore." David had hinted earlier, to relieve my anxiety. It seemed to me that description applied to many guys I have dated in the past.

I parked the car at the coffee shop just about on time, the traffic had been light. David stepped out of the passenger seat.

As he did so, he held my hand for longer than was necessary, and then closed the door.

I smiled, and he turned to enter the cafe.

With a very deep breath, I signalled out into traffic and turned up the air conditioning to keep myself cool. The anxiety of meeting people as 'Emma' was back with me and the butterflies in my stomach were rising with every heartbeat.

The garage was only a few minutes away, and I stopped a line of traffic as I waited to pull the car across the road and into the yard of the garage itself.

Thankfully, I was the only car present. David was right, it was a small operation with only one car-bay that was currently unoccupied. The tall garage doors were wide open.

There was a single four-post service lift ramp, and I was not sure where I should park. I decided to leave it facing the bay, but not to drive in.

In the garage was a man, and I observed that David was correct in his age estimation. 62 and 5ft 9" I would say, and carrying more weight than he should.

He sat on a stool with a cup of tea in his hand. He wore heavy boots and a pair of dark blue overalls that had certainly seen a lot of use. He had tied the arms of the overalls at the waist, and had worn a white t-shirt. We could all agree it was not the best colour to wear around a working car garage.

He wore silver glasses on his head, that covered his thinning grey hair which had been cut short. He seemed to have a kind face.

I paused for a second. Was I going to do this or drive away?

Every time I have met someone I have had to make this decision. As a cross dresser, meeting partners in normal situations is almost impossible. The internet and its' dating forums had thankfully filled this gap and I had found that it was easy to obtain meetings with men who want to meet t-girls for nothing but sex.

The difficult part was going through with it. The first stage, the most difficult stage, I seem to go into an autopilot mode. If I want things, I have to go out and get them.

I opened the door of Davids car and stepped out onto the yard. It was a mixture of dirt and stone, with several potholes full of rain from the previous night.

As I alighted I felt the eyes of the old mechanic watch me. He had put down his cup of tea, and jerked his spectacles down from his head and onto his nose.

I took my handbag from the car and closed the door, walking slowly and taking care not to find a deep hole with my heels. Still, I could feel them sinking into the ground.

"Hello" Said the man, looking me up and down.

"Hello." I spluttered, trying to imitate my poshest voice.

My accent and the lower nature of my voice startled him, but he remained smiling, and his eyes bright.

"Just an oil change?" He asked.

"Yes, thats right." I responded.

He wandered into the rear of the garage and looked at a ring bound notebook. He took a pen and appeared to tick off a box.

"I was expecting David." The main said, still facing away from me.

"I'm just dropping it off for him." I replied, "He is busy this morning."

"Are you his wife?" He said, looking over his shoulder to face me.

"No, nothing like that," I replied, "just friends."

You wouldn't be too shocked to find that this is the opening question for many men to ask a woman. It is laying the groundwork for later.

"Ok let's get it up then." Said the mechanic.

I handed him the keys.

His hands were darker than my own, and his rough and broken skin felt sharp as it brushed against my own milky-white hands.

He was till taller than me by a couple of inches, but didn't tower over me like David does. I was glad that I had chosen my 3" heeled boots and no higher.

He took his time in the car, taking care to apply a thin polythene covering to the seat and what looked like a shower cap to the steering wheel before getting in. He adjusted the seat back and turned the key.

He drove quickly, faster than I expected and the car mounted the lift ramp with a bang.

He got out of the car, but turned to face it again, reaching back into the footwell and the bonnet popped.

It startled me, although I didn't know what I was expecting otherwise, and I rocked back with my high heels on the concrete floor.