I turned the steering wheel left. The car turned and came to a halt in our driveway. I looked around the street. It was quiet as I opened the door and, lifting my two packages and my briefcase, I stepped out of the car.
Flicking the little switch on the fob, that familiar beep sounded as the car security system locked and kicked into life.
Walking up the path, I opened the door and stepped inside. Glancing over at the phone, the message light flashed bright red.
Putting down my bags, I picked up the receiver. My long, red-coated false nails pressed the replay button. The machine kicked into life. Uh, hello, Amy. It is Keith Jackson here. I just want to let you know that you have got the contract. A pause as a smile spread across my face. I still had the selling skills, I thought. Keith's voice sounded again.
There are a couple of points I need to discuss with you, though, just to tie up the deal. I will be in the office till around five thirty. Can you give me a call? Okay, speak to you soon. Oh, and congratulations, and I look forward to doing business with you.
I put the phone down, glancing at the clock in the hall. I noted it was just a couple of minutes to five. Better call him, I said to myself. Picking up the small diary-like phone directory, I found the number and tapped it into the phone. South Lanarkshire Council, can I help you? The voice announced.
Uh, can I speak to Keith Jackson, please? I said.
Can I tell him who is calling? The receptionist asked.
Uh, yeah, sorry. It is Amy Clark. I had a meeting with him earlier today.
Okay, Ms. Clark. I will just put you through.
The phone went quiet for a second before a pre-recorded classical music track kicked into life, one of those annoying tapes that make you scream if you are on hold for any longer than a minute. Happily, I heard the voice come back quickly. Just putting you through. Mr. Jackson, I have Amy Clark for you now.
Amy, I take it you got my message? He paused.
Yes, I did. Thanks.
No problem. Your bid was the best. There are just a couple of little points I need to discuss with you.
Okay, well, I am free most of tomorrow, knowing full well I had nothing planned and was keen for another day as Amy.
Well, I am tied up in meetings most of the day. How about dinner?
My heart skipped a beat as I played back what he had just said in my mind.
You still there? he asked, filling the awkward silence.
Uh, yes, I am. I was just thinking if I could make it.
Your partner will not mind, will he? he said.
Uh, no, he... I paused. He will not. I almost dropped myself in it, I thought as my heart continued to beat faster. He is away on business just now, I said.
Well, then, let us say Di Angelo's at about eight, if that is okay for you.
Yeah, fine. I will see you then, I said.
Looking forward to it, he said as the line went dead.
What have I done? I have just agreed to go to dinner with a man.
The dinner
Shortly after I had got off the phone with Keith, I called Amy to let her know how we got on.
You sound a bit out of breath? I asked as she picked up the phone.
Yeah, I have just been to the gym. All these cooked breakfasts and evening meals are not good for the figure, she said. So, how did it go?
Fine, you have got the contract? I said, a smile breaking out on my face as I said it.
Oh, you are a gem. I knew you could do it, excitement in her voice as she took in the good news.
Uh, there is just one thing. He wants to discuss a couple of minor points before we complete the deal, I said.
What points?
I do not know. He just wants to discuss them tomorrow.
That is not a problem, is it? You could do it one more time, couldn't you?
Uh, well, yeah, but he wants to do it over dinner. I could hear Amy laugh. It is not funny, I said.
What is the problem? Have you been out for dinner before?
Yeah, but not as you, I said.
It will be fine. Look, you can spend some more cash. As you got the contract, go get a dress or something tomorrow. Not too sexy, though, she said as she once more began to snigger.
Yeah, very funny. Okay, looks like I will need to do it. How is the conference going, anyway? I asked.
Yeah, good. The food is great, the room is wonderful, a huge, comfortable bed, and I am making some great contacts, she said with a slight smirk in her voice. Look, you take care. I had better go. I am meeting one of the girls for a drink. I will call you again tomorrow, okay, darling? And thanks for this. I will make it up to you when I get back, okay?
You had better, I said, and then she was gone.
I stood in the hall, mulling over the situation. Here I was, given the opportunity of a lifetime, something I had dreamed about: getting the opportunity to dress in women's clothes with Amy's blessing.
But yet, something did not feel right about it. Stirring myself, I walked out into the garage and picked up a small set of ladders.
Opening them out, I climbed up the three or four steps. Looking up, I pushed up a ceiling tile and stuck my hand inside. Feeling about, I found a little bit of rope. Gripping it, I began to pull. In no time, a little package appeared at the edge of the open tile. I lifted it out and replaced the tile before climbing down.
I looked at it, wiping away some dust. I knew what was inside. You see, that is the thing about those of us who have feelings like me.
We are devious. Yes, we say that we will never dress up again, but all the time, that urge is there, the temptation to do it. How many of us have bought things and then thrown them away? Yeah, I know, all of us.
When Amy had caught me before, I had vowed to get rid of everything in an effort to save our relationship, and I had, well, almost. Inside this little box were the two most expensive items I had bought before I had married Amy: a set of state-of-the-art breast forms that heated up with your body heat and nipples which reacted to heat as well, and my latex pussy, so realistic and accommodating, capable of taking one of Amy's dildos without any problem.
Well, if I need to go to dinner with a man, then I had better make the effort, I said to myself as I switched off the light in the garage and went back inside.
I was in bed early that night. Sleep did not come easily. My head was filled with a mixture of thoughts, some excited about what the day ahead would hold, and some of pure terror at the situation I found myself in. I shifted about the bed restlessly for a couple of hours before exhaustion took over and I slipped into a deep sleep.
Dinner at eight
A bright sunray beamed across the room as I woke the next morning. I turned, stretching, looking at the bedside alarm. It had just turned ten am. I roused myself, aware that I had some shopping to do. I pulled on a pair of shell suit bottoms and a light t-shirt. Downstairs, I poured myself some fruit juice and made a slice of toast.
Sitting by the table, I munched on my toast and thought about the day ahead. I needed to get dressed, shoot into town and buy a dress for tonight, then back out and get ready. I figured I would need to be back by five, have a soak, and then get ready. After all, I needed to be as perfect as possible tonight. I was going to a posh restaurant, so everything needed to be just right.
Back upstairs, I dressed for the day. Underwear on, I pulled on the skirt I had worn yesterday. Amy had said not to use any of her stuff, but as all this was her doing, then I figured that she owed me.
Looking in the closet, I pulled out a purple silk blouse. Slipping it on, I sat down to do my makeup for the day. Half an hour later, I was dropping my cigarettes, lighter, and some perfume into a handbag of Amy's.
I pulled on the black leather gloves I had bought the other day and, opening the door to the garage, I stepped inside.
The door slid up remotely as I started the engine and drove the car outside. Stopping briefly to activate the closing of the door, I put the car in gear and drove off to town. After all, I was going out to dinner tonight, and I needed a dress.
Early that evening, I sat in the conservatory with a glass of white wine in one hand and a cigarette in the other. My legs were tucked up under me, still dressed in Amy's clothes that I had gone shopping in earlier. My mind was rationalising the way I felt when I was dressed this way. I felt female. I felt delicate. My emotions changed.
Heck, even what I watched on TV was different. No sports shows, more chat shows and magazine-like programmes, you know the stuff. The way I carried myself was different, my stance so feminine. Even the way I smoked this cigarette and held this glass was so much more poised and elegant than Andrew would be.
Like most guys going out, you pick a shirt, maybe a tie, a pair of trousers, have a wash and shave, and then you are off. But when I was dressed like this, the procedure was almost military-like: the preparation, the attention to detail.
I think that is why I had never argued with Amy all those times I had sat waiting for her to get ready to go out to dinner or the cinema.
I understood and appreciated the time it took to look good. Glancing across at the wall clock, I noted the time. Draining the last of my wine and crushing out the cigarette, I rose. It was time for me now to go and make that effort.
Just over an hour later, I stood admiring myself in front of the mirror. The dark red dress I had bought earlier that day clung to my figure. Not too short, sexy but classy, like I always liked to look before my hobby had been curtailed somewhat. The black sheer stockings glistened on my legs. My feet were encased in the black shoes with the red heel that I had bought just the other day. My makeup was heavy but not tarty, definitely evening style: eyeliner, mascara, a dark red lipstick, all coordinated to suit my outfit.
I reached for my cigarettes and pulled one out. Much more comfortable now with the nail extensions that Sheila had fitted just the other day, the nails painted in a matching dark red. I picked up my lighter and sparked it into life, pushing the tip into the flame. I inhaled cool menthol smoke, a nervous rushed exhale as I thought of the night ahead. I looked at the cigarette, the dark red lipstick coating the filter as I took another draw on it. Picking up my bag, a black jacket, and my gloves, I left the room and headed downstairs.
I poured a glass of wine and stood looking out the window, my arm folded under my fake breasts across my chest. This is it, I thought to myself. One of the things that I had always hoped to do: go out for dinner with a guy, to be treated as a lady, wined, dined, and complemented, I hoped, all with the approval of my wife.
How did I get here, I thought? Well, I am here now, so I might as well make the most of it. Taking a final draw from the cigarette, I extinguished it. I looked around the house, checking everything was secure. Then, slipping on my jacket and gloves, I grabbed my bag and stepped outside.
A taxi sat by the roadside, awaiting my arrival to transport me to my date for the evening.
The taxi crawled to a stop. That will be four pounds and thirty pence, miss, the driver said. I opened the bag and retrieved Amy's small purse. Opening it, I took out a five-pound note and handed it over.
Keep the change, I said. Reaching for the door, I pushed it open and stepped out. I pulled the coat around my shoulders, straightening it as I did so. The cab sped away as I walked towards the restaurant.
Butterflies the size of pigeons fluttered around in my stomach as I paused and took out a cigarette. Fumbling a bit with the gloves to get a grip, I pulled it free and put it between my lips. I looked inside the bag for my lighter. As always, the clutter of a woman's bag hid it from view.
Here, let me, a voice said behind me.
My frantic search in the bag had made me unaware of the gentleman who had appeared just behind me. He offered me his lighter, which he lit and held towards me. Gripping the cigarette with my gloved fingers, I pushed it into the flame and lit it.
Thanks, I said, blowing smoke skywards.
No problem. Are you here for a meal?
Stupid question, I thought, as I was standing outside a restaurant. Uh, yes, just a business dinner, I answered.
I am here with some friends. A retirement party, he said.
Nice, I said, pulling hard on my cigarette and blowing the smoke to the floor. I had better get inside, I continued, dropping the half-smoked cigarette on the ground and crushing it out with the toe of my shoe.
Nice meeting you. I am Geoff, he said, offering his hand to me. I took it and shook his hand.
Amy, I replied as I let go of his hand and moved to the door.
Inside, I scanned the restaurant, looking for Kenneth. A waiter approached. Can I help you, madam? He asked in a polite tone.
Yes, I am supposed to be dining with a Mr. Jackson, Kenneth Jackson, I said, gaining confidence with every interaction I had with a person.
Yes, ma'am. He is waiting for you in the conservatory area. I will just take your coat and then show you to his table.
I slipped off my coat and handed it to him. He summoned someone from the cloakroom to my right. They hurried over and took the coat from him.
This way, madam. He said, gesturing for me to follow him. I walked, my heels clicking on the oiled hardwood floor as we made our way through the tables out into the bright conservatory area. Seconds later, I caught sight of Kenneth. Our eyes connected. He smiled. I smiled back as he began to stand.
Amy, you look lovely, he said as I approached. He leaned in and kissed my cheek.
I blushed. Thank you, Mr. Jackson, I said as the waiter pulled out the seat for me. I sat down, taking care to make my posture as feminine as possible.
It is Kenneth this evening, he said as he stared across the table at me. Now, let us order. I am famished, he said as he gestured at the waiter to bring a menu.
During the meal, I discovered that Kenneth was in the process of finalising a divorce from his wife. They had been separated for a few years now. His daughter lived in Australia with her partner, and he had one grandchild.
I had been more guarded on the information I had offered about my life, just confirming my marriage status and that there were no children. The chat had been pleasant and complemented with some quite lovely food. I had enjoyed the evening and was now very relaxed in my Amy role.
Just under two hours later, as we sipped hot coffee, our meal at an end, I spoke. Uh, Mr. Jackson, I mean Kenneth. You said there were a couple of details on the contract you wanted to discuss.
Uh, yes, minor details, really. I hope we can get around them, as I really think we could work well together.
Okay. I blushed slightly again.
Well, it is staffing, really. You see, we have eight employees at the moment who work in the kitchens. I nodded. He went on. Three of them are students who are only filling in during the summer term. There is one who is pregnant and will be leaving us soon. But that leaves four. Two of them are retiring in a couple of years, and the other two have been with us for a few years now. So, I was wondering if you could take them on when you take over.
I sat for a moment. Uh, well, I would have needed to hire a couple of extra people, maybe only three. But if there will only be four left soon, then I guess I could manage the extra body, I said.
Excellent, he said.
And the other thing? I asked.
Oh, yeah. Well, I was wondering if you could also keep our two delivery drivers who collect supplies and make deliveries. There are two council vehicles adapted for food carrying. We would maintain them and fuel them. You would only need to contract the drivers.
I thought some more. Well, I suppose so. I mean, my own driver is usually flat out anyway. So, if you are maintaining the vehicles, then I suppose I could meet the costs of the drivers' wages. It might be at slightly lower rates, though. Do you think they would go for it? I asked.
I have already spoken to them. They will be happy still to be in work, so as long as the wage cut is not too serious, I do not see a problem.
Okay, I think we have a deal, then, I said, extending my hand. He took it. His large fingers engulfed my hand, and I felt tingles in my spine as we shook hands.
I will get the bill, he said, gesturing towards the waiter. Uh, I can pay, I said.
Nonsense, he said. Council expenses and all that. And I was wondering if we could maybe go for a walk along the riverbank. He paused, looking at me. He went on, I mean, unless you need to get home. It is just that I have had a really lovely night.
I blushed slightly again and hesitated. Uh, I do not know. Uh, well, okay, then. Why not? It is a nice evening, I said.
Good, let us get your coat, he said as he handed payment to the waiter, and we stood up.
A few minutes later, we were strolling along the paved walkway by the river. Meaningless conversation flowed between us, thoughts on life, business, and the local economy as we strolled in the fading light. Bright riverside lamps kicked into life, flooding the walkway with strong white light as the evening grew dark.
A small jetty poked out into the river with a metal bench for those wishing to sit and look out over the calm river.
Can we have a seat? I asked, my calves aching a little, still strengthening to the art of walking in heels again.
We approached, and both sat down. Do you mind? I said as I took out my cigarettes from my handbag.
Not at all. Indeed, I will join you Kenneth said as he removed a small cigar case from his inside pocket. He took out a slim cigar and lit it, offering me his flame. I poked the cigarette tip into the light and inhaled.
Thanks, I said. So, do you think the contract will be awarded? I asked, blowing a billowing cloud of smoke upwards away from us.
I do not see any problems. I am having a meeting with some of the other councillors tomorrow, and we are keen to get it finalised. So, I should be able to let you know tomorrow.
That would be great, I said. Instinctively, I reached out my hand, touching his arm, squeezing slightly. We sat in silence, finishing off our smokes.
I had better get home, I said as darkness closed to a deep, inky night.
Okay, I will walk you back to the taxi rank, Kenneth said.
A few minutes later, we reached the taxi rank. Two cabs sat waiting for fares. Kenneth reached for the handle and opened the door. I went to pass him.
I have enjoyed our evening, Amy, he said.
Me too, and hopefully all will go well tomorrow.
Suddenly, he leaned forward and planted a quick kiss on my lips. I blushed and quickly got inside the taxi.
I will call you tomorrow, he said.
Okay, I answered as the door closed and the cab began to pull away.
I sat in the back, thinking about what had just happened. He had kissed me. It had taken me by surprise, but nevertheless, part of me had wanted it. In fact, a big part of me had wanted him to take me in his arms and snog the face off me, but maybe that was pushing it a bit. My mind rolled away, fantasising about the situation.
Miss, we are here, the taxi driver roused me from my comatose state.
Oh, okay. Sorry, I was miles away, I replied as I fished in my bag for my purse.
Minutes later, I was in my lounge. I poured a large glass of wine and grabbed a cigarette. Lighting up, I relaxed back on the settee and, once more, my mind strayed back to what had happened at the taxi. I could feel myself getting hard as my mind replayed the incident.
With Amy gone for the last few days, I was pretty horny. Putting down the glass of wine, I stood up and freed my cock from its prison. Sitting back down, I began to pleasure myself with long, slow strokes as I closed my eyes and thought of Kenneth touching me, my breasts, my backside, his kiss, firm and passionate.
I stroked harder and took a deep draw on the cigarette. Now, it was my turn. My long, manicured nails were pulling down his zipper, freeing his maleness from its cotton prison.
My hand curled around it, stroking it. My lips engulfed it, sucking hard. Another draw on my cigarette while I played with myself. Finally, I felt the tension erupt, and my seed exploded over my hand, splashing my stockings. A final draw on my cigarette, and I relaxed back. The night was over, and what a night it had been.
Clinching the deal.
I woke the next morning, still dressed in one of Amy's nighties. I rose. Pulling on a dressing gown and some mule slippers, I went downstairs and made a coffee. Lighting a cigarette, I looked outside. It was a bright morning, and I had the rest of the day ahead of me.
My final day as Amy. What a blast it had been. I was determined to make the most of it. Draining the last of my coffee and extinguishing the cigarette, I left the kitchen and went back upstairs to dress for the day.
Over an hour later, I was back downstairs, dressed in a pair of tight blue denims which were tucked inside knee-high black leather stiletto-heeled boots. A tight white cotton top was under a short black leather jacket. My makeup was a cross between evening and day wear.
If this were my last day as Amy, then I wanted to be noticed. I wanted people to see this sexy lady walking in heels through a busy shopping centre. I picked up my bag and stepped out into the garage. Opening the door, I unlocked the car and got inside.