"Good morning Lisa." Rachel cooed as she walked into the room. "Hurry up and get ready we need to be off before the shops get too busy. You remember what we decided last night don't you?"
"You mean I have to go out as I was dressed last night?" I whined. "I'll stick out like a sore thumb. The skirt is far too short."
"I've thought of that." she replied. "Yesterday I bought a similar skirt and some high heels so that when we go out you will not feel too different. Hurry up and get dressed and ready. I'll change and we'll have a light breakfast before we go. I'll shout when the kettle's on." With that she turned and left the room.
I knew that I was beaten; in some way I was glad.
I quickly shaved and showered. I used the perfumed talcum powder again and then did my make up. I dressed in the same clothes that I had worn the previous evening. Once again revelling in the feel of the sheer nylon on my smooth legs and was just fastening the belt when Rachel called from downstairs that the kettle was on.
Once again as I went out onto the landing the rubbing of my smooth nylon encased thighs and the restriction of the skirt combined with the high heels caused stirring between my legs.
When I got to the kitchen I saw that Rachel was wearing a similar skirt to the one I was wearing but on the top she has a tight fitting red sweater which really showed off her breasts. She also had red high-heeled shoes on.
"Hi honey." she said as I entered the kitchen. "I thought we would have a quick snack in here before we set off. Is that OK with you?"
"Whatever you say." I replied.
It was strange to hear both of our heels clicking on the floor as we took our breakfast to the breakfast bar to sit down. I remembered the lessons of the previous evening as I sat down on the high stool to eat my cereal and drink my coffee.
"You look good this morning." she said. "Don't worry you are very convincing and even if they do work out that there is something between your legs that women should not have I will be there to help. I have just thought about a problem, however," she went on. "We have not really thought about how you talk."
"I hadn't really thought about that." I said.
"Well I can't do all the talking so we are going to have to get you to try and do something to feminise your voice. Let's try now while we have breakfast."
We tried with me pitching my voice at various heights and eventually found a pitch, which I could reproduce, that sounded vaguely feminine without being too high pitched to sound false.
"You keep practising that and you should be OK." she eventually said. "Now if you are ready then we will leave the pots until we come back. Let's go shopping."
I was still very nervous about leaving the house let alone going into shops and areas where there were other people but eventually I stood up straightened my skirt and got ready to leave.
"Wait a moment." Rachel said, as we were about to go out of the front door. "You need a handbag. You also need the essentials that go in it. Let's go upstairs and sort you out."
We went upstairs and she found a black shoulder handbag, which she gave to me. "Here use this. It is one I have spare and am not using at the moment. You will need to put lipstick, mascara and some other oddments of make up in it as well as your credit cards, wallet, keys and money. A comb or brush would be useful with the length of your hair and some tissues. We can get other essentials at a later date."
What other essentials I wondered as I put all the things she had told me into the small bag. No wonder women have such a problem finding things in their handbags.
"Slip it onto your shoulder and it will give you something to do with your hands as you walk." she said.
"Ok. You lock the door and I'll get the car started."
It suddenly occurred to me that this was going to be the first time I had ventured outside the house whilst dressed. Taking my keys in my right hand and the shoulder bag on my right shoulder I followed my wife to the front door. Before leaving I set the house alarm as usual and then stepped outside. It was a warm summer's day and I thrilled at the sensation of the warm breeze around my nylon-encased legs and the strange feeling of the same breeze blowing up my skirt.
"Hurry up. We haven't got all day!" my wife shouted from the car.
I turned round and locked the front door. It felt strange not putting the keys straight into my trouser pocket as I usually did. Instead I had to stop and think about opening my handbag and putting them in there. This took a bit of time and my wife honked the horn to tell me to hurry up.
Once again I turned round and then I walked along the drive to the car. I cannot recall the number of times that I have done that but this time was the weirdest. The sound of my heels on the drive and the feeling of the sun on my legs gave me the strangest sensation. In some ways it was exhilarating and by the time I reached the car I was quite excited.
Now came the problem. How to get into the low car dressed in a short tight skirt and high heels? I decided to try it by stepping into the car with one leg and then trying to sit down and smooth out my skirt all in one action and then bring in the other leg.
"I think that may need some practice." Rachel said as I ended up with my skirt around my middle, showing most of my panties. I frantically moved around in the seat tugging at the skirt in order to regain some dignity.
"You will have to think about how you do things before you get yourself into trouble." Rachel stated. "When you get into a car think about how you are going to bend and how your clothing is going to be effected. It is really not too difficult. Ok off we go."
Thankfully we drove to a nearby town to do the shopping. As I work in the local town I was worried that someone might recognise me so a trip to another town seemed to be a much safer bet.
When we reached the town centre we parked in a multi-storey car park. Rachel got out of the car and closed the door.
"Come on," she said as she walked around to my side of the car. "Time to go. We need to buy you some pretty things for our date tomorrow night."
Getting out of the car was nearly as much trouble as getting into it. I could foresee vast amounts of thigh and panties being shown off to all that wanted to see it and said so to Rachel.
"Just put your knees together, lift your legs and turn round in the seat. Then put both feet out of the car and, using the door sides ease yourself out of the car. I have just done the same thing. You obviously were not watching."
It sounded so easy. I did manage it but realised that there was a lot more to being a woman than just wearing the clothes.
Rachel locked the car and we walked to the exit, our heels clicking in unison. As we were on the fourth floor this meant that we would have to either walk down the stairs, a daunting task in high heels, or wait for the lift. We pressed the button for the lift and waited.
While we were waiting two young men arrived and stood waiting. I tried not to look at them but it was difficult. Thankfully the lift arrived and the doors opened.
There were a number of people already in the lift and the two men stood to the side to let us get on first. As it was so crowded in the lift Rachel and I ended up facing each other with the two men coming after us standing behind each of us.
Someone pressed the button to send the lift to the ground floor and the doors closed. As the lift set off I was not sure if it was the sudden movement but I thought I felt a hand on my bottom. As the lift reached the ground floor I was certain that the man standing behind me was feeling my bottom. When the doors opened on the ground floor he definitely pinched my bottom and said "After you darling."
I walked out of the lift and turned round to wait for Rachel who was immediately behind me. She was smiling.
"What are you smiling at?" I asked.
"You. You nearly lost it there when that man was feeling your backside," she said.
"Well so would you if it had happened to you."
"It did and I didn't." she retorted. "Welcome to the world of womanhood. That sort of thing happens all of the time. More so if you are dressed as we are and there is an easy excuse. Get used to it. It at least proves that you can pass. I doubt he would have squeezed you if you had been dressed as a man."
On reflection this made me feel better about the incident. I was still lacking in confidence but thinking back to the incident I realised that Rachel was right. It wouldn't have happened if I had been dressed as a man. Dressed as I was with a short skirt and high heels it seemed to be more natural.
"How do you stand it?" I asked.
"Well it depends on the situation." Rachel replied. "Sometimes you don't. You turn around and lay into the guy either verbally or physically. Usually though it is harmless and as I am sure you now begin to understand it makes you feel good to realise the effect you can have on a man. Understand that the way that you look can drive him crazy and cause him to do things that he would not normally do. Just think of the power that can give you."
"I see." I said. "There is much more to this being a woman than just dressing the part isn't there? I suppose, thinking about it, it did make me feel pretty good at that." With that we giggled and the two of us set off for the shops.
"We need to get you some clothes for every day and some for the date tomorrow night." Rachel said.
"Don't remind me," I said. "I can't help worrying about that"
"Come on let's take your mind off things lets go and shop," she said leading me into a clothing store.
We spent a long time going from one store to another. At first I was very nervous but when I found that the assistants did not look at me as though I was from outer space and generally seemed helpful I began to relax and enjoy myself. Never in my wildest dreams did I ever think that I would be doing what I was doing now. Walking into dress shops. Holding dresses up to see how they would look and even going into changing rooms and trying them on. I was having a whale of a time.
Luckily the name on my credit card only has an initial so I was able to use it without any trouble so we eventually ended up with some outfits that Rachel thought would be suitable for Lisa to wear. All of them have short skirts as Rachel thought that Lisa's legs were gorgeous.
"If they are looking at your legs then they are not looking at your face." was what she said and I supposed I had to agree with her.
As the morning wore on Rachel said that we now needed to look for some shoes. At the moment I was wearing the only pair I possessed so more were necessary.
We went in the nearest shoe store and looked at their selection. A young male assistant came over and offered to help us. I sat down on the stool and he brought some of the styles we had looked at for me to try. He removed both of my high heeled sandals and placed a new shoe on each foot, in the process stroking the back of my calves and moving up to the back of my knees. I smiled at him and partly opened my legs so that, if he was at the right angle he would be able to see my panties.
What was I doing? Here I was in a shop buying ladies shoes while dressed in a short skirt which was well above my knees and playing up to a young assistant. I couldn't believe it. It seemed so natural.
In the end we bought three pairs of shoes. One red pair with three-inch heels, a cream pair with the same height heel and a pair of strappy evening sandals with a five-inch heel. I must have impressed the assistant because he gave me a good discount on the shoes and asked me to come back again soon.
Rachel couldn't stop laughing as we left the shop.
"I thought you were worried about being seen dressed as Lisa." she said. "That was one of the worst cases of flirting I have seen in a long while. That lad had the hots for you. Didn't you see the effect in his trousers when you opened your legs? You shameless hussy you."
It was getting on towards lunchtime by this time so we headed for a nearby cafe. When we were seated a waitress came over and took our orders.
"I need to go to the loo." I whispered to Rachel when the waitress had left.
"Well it's just over there. Make sure you use the right one won't you." she said.
"What do you mean?"
"Use the ladies and don't forget we sit down to go. You will find it simpler if you do too and take your handbag with you."
It hadn't really occurred to me that I would have to use the ladies but a little nervously I stood up, picked up my bag and walked into the toilet. As it happened I need not have worried. There were two stalls, neither of which were occupied and so I chose the one nearest the door.
Once inside I noticed that there was a pan as normal and a plastic box with a metal lid at the side. I assumed, rightly so, that this was for soiled sanitary pads and such. I shut the door to the stall and hung my shoulder bag on the hook behind the door. I then realised that in order to relieve myself I was going to have to remove my panties and tights as well as lifting my skirt. It was at that moment I realised what Rachel had meant by sitting down being simpler.
I eased my panties and tights down to my knees and then lifted my skirt as I sat down on the seat. This meant that my penis was still between my legs and pointing in the right direction. Even so it was sometime before I was able to relieve myself and to finish urinating. I then wiped the end of my penis before tucking myself away again as I had before and pulling up my tights and then my panties. I smoothed down my skirt and then flushed the loo.
As I opened the stall door the door opened and Rachel walked in.
"I was beginning to get worried," she said. "You seemed to be taking a long time."
"I'm sorry but I've a bit more to look after than you real ladies have." I replied. "Still I'm just about ready now."
"I suggest that you freshen up whilst you are here." she went on. "It's the sort of thing we women do and one of the reasons why there are always plenty of mirrors in our toilets. See you back at the table."
I washed my hands and whilst doing so noticed that some of my make up needed repairing and that my wig was in need of a tidy. I opened my handbag and realised why Rachel had insisted that I put so much stuff in it. I repaired my make up, added a little more lipstick and combed out my hair a little.
As I was doing this another lady entered the toilet, Smiled at me and entered a stall. This gave me a thrill as I was obviously passing as Lisa even in this woman's holy of holies. After putting the hairbrush back in it I put my bag back on my shoulder and left the room.
When I get back to our table the waitress had already brought our orders. So we sat and had a light lunch. I was feeling quite hungry but I remembered what Rachel had said about the way that women tend to eat and refrained from cramming my mouth full of food. I sipped the coffee and once again had the thrill of seeing the marks from my lipstick covered lips staining the rim of the cup.
"So what are we going to do now?" asked Rachel as we were finishing off our lunch.
"Well we have bought quite a bit and, quite frankly, I can't wait to try some of them on to see how I look. I think we should go home and try them."
"That's what I thought you would say. Ok lets go and see how good Lisa looks in her new clothes."
With that we stood up and gathering up our bags we paid the bill and left the cafe.
Outside it was still sunny and I once again revelled in the feeling of the sun on my nylon-encased legs and the soft breeze blowing around my legs and up my short denim skirt. The sound of our heels on the pavement sent shivers down my spine but I was becoming accustomed to being out dressed as Lisa and felt a lot more relaxed than when we had first got out of the car. I tried to look around rather than concentrating on walking without looking too masculine.
"You've started to relax more." Rachel said eventually as we neared the car park. "You are looking much more natural, your walk is improving and you seem to be enjoying yourself. That's good. Try and forget how you are dressed and just be as natural as possible. Look around yourself and remember when someone looks at you look back at them. That is how most women do it. If it's another woman then perhaps smile and acknowledge her. If it's a man then you will probably notice that his eyes are not looking at your face but at other parts of your body. I bet you've noticed how the men we have seen have been looking at either my legs or bust in this tight red top well amazingly enough they have been mainly looking at your lovely legs. Haven't you noticed?"
"Not really, apart from the assistant in the shoe shop. I have been trying to concentrate on my walk and I have been trying to avoid looking at people in case they realise that I am really a man dressed as a woman."
"Well from what I've seen so far no one has doubted that you are not what you appear to be, a good looking sexy woman in a short skirt and high heels, who is not afraid to show her assets off in public. Once you get used to it you will find that it makes you feel good when someone looks at you as though they want to fuck you. Just think what those two men at the lift thought this morning when we arrived. If they had any doubts do you think you would have had your bottom felt?"
"Well no I suppose not and in some way I think I actually felt flattered about what had happened although I am not sure how I would have handled it if it had gone further."
"I can see we are going to have to talk about how to handle trouble like that quite soon. There are ways but it does depend on what sort of messages you have been sending out to the man you are having the problem with. Quite often the way you are dressed and the way you behave gives a message to the man that you do not want. You have to be careful."
By this time we had reached the car park and once again we waited for the lift. This time when the doors opened a family with two children came out of the lift. I smiled at the woman and she smiled back at me but as she did so she looked at her husband who had just passed us and grabbed hold of him as he was turning round to look at us as we entered the lift. As the doors closed we could see she was talking heatedly with him.
"See what I mean," Rachel commented, "he couldn't help himself. He had to turn and ogle our legs."
I did begin to see and realised the power that woman, and how they dress, can have over men. It made me feel excited that I could have that sort of effect on someone dressed as I was.
We got back to the car. I still had the problem of getting in but this time I watched Rachel. She had the problem of her skirt riding up her thighs but once she had sat down she adjusted the skirt by lifting herself from the seat and pulling it down. I did the same thing and found that although the skirt rode up the situation was not as bad as I had found that morning.
Once we had left the car park and begun the drive home I settled back in the seat, put my head back and closed my eyes. I was relaxing more and feeling less and less self-conscious about being out dressed up.