Dreaming

by Mikki

 

As in all stories of this kind it started when I was about 5 or 6, up stairs in the privacy of my mothers or sisters bedroom when all were out.

First by liking the feel of their clothes and the smell of the make up.

I can remember getting hold a small lip stick and putting that on and looking in the mirror then a powder compact which again I would put on and enjoy the feelings I was getting. These two items would grow as time went on which I hide in a small air intake hatch in the wall in my bedroom, getting them out and applying when I was on my own.

Later I would get hold of a pair of stocking and then tights, which together with clothes handing up in their bedrooms I would put on and mask around in mush to my satisfaction. As I got older (year or so) I would get sexually aroused and again as time went on I would ejaculate at first on my own with no help. But as I found that I liked the feeling of coming I would finish off my dressing with helping my self to a climax.

Getting older meant I would find myself being on my own more and more especially at the weekend which I would take full advantage of by getting out my make up and helping my self to their clothes. I would fantasise and plan a trip away by packing my bag and going off on a train and get dressed in the toilet and come out a female, doing the reverse on the way home. This I never did. BUT

I had an aunty who had lost her daughter years earlier; she would invite me to stay at the weekends. I would stay in her daughters' bedroom. After a couple of weekend breaks I found myself looking around wardrobes and found all her clothes and make up. As I got more adventurous I would apply the makeup and put on the clothes and wigs that I had found carefully putting things back so to avoid detection. I did find new clothes and other items every time I looked so I took advantage of the fact and enjoyed myself, clothes would be washed and folded back in place every time I visited. Unknown to me my Aunty found out and would leave me new clothes and wash the ones I had soiled. She did confront me a few times but I denied it every time until I could not deny it any more. Thinking she would be cross and tell my parents I was completely wrong. She was very understanding and even suggested a trip out dressed as a girl, which I finally agreed to as long as she dressed me and did my make up knowing what a mess I normally made. This we decided would take place the next weekend.

When the Friday finally arrived after a long week longing for it to come around, I shaved (I was shaving by now) legs and chest and face and set off for her house having relived myself making a mess in my pants.

She was waiting for me and took me up stairs to my bedroom that I had my new clothes laid out on the bed. A new silk skirt with a matching blouse lay on the bed with a really fine pair of black stockings with a very sexy bask bra and suspenders ready for me and a pair of high heels which I hoped were all my size and false breasts.

My aunty said she would leave and return when I was dressed and ready for my make up. I was in such a rush that I nearly ripped off my clothes and dived into my new clothes but I did calm down after I went to the toilet again to relive myself. When I returned I unpacked the small briefs and put on the bask, which I found hard to do up but was getting more excited as the minutes went. I did not want this time to end. Then I unpacked the stockings taking care not to pull them. Putting them on I could feel the silkiness of them pulling them up and attaching them to the clips at the top. Put in the silicon false breasts into each cup, being the first time I had used such things I noticed how heavy they felt. Then the silky blouse again feeling the silk set me off again with a tingling sensation.

Then I placed the wig on my head, which I know would need adjusting later. Then I put on the shoes, which fitted perfectly. After standing up I fell over with a bang, bringing in my Aunty who must have been watching for it was no time at all before she came in (as I was hitting the floor) I was again embarrassed by the fall but soon got over it.

My Aunties face light up when I got up and sort of wobbled when I tried to stand up straight. She was over come and said that she had never been as happy in a long time as that of now. She led me over to the dressing table and sat me down in front of the table and pointed me to the mirror. She said take a look and then turn away which I did not knowing what she wanted. She said next time you look you will be made up and then we will be ready to go out. I started to get worried.

After turning away my aunty got out the make up bag and found the foundation cream, which she applied and I know all would be well when she had finished.

Then the eye liner (black) and the lip liner (red) I would loved to have watched but she said next time she would help me do my own make up but this time it was her that was doing it all.

Then the eye make up on the upper eyelid (light green to match the clothes) and then the mascara and the reapplying the eyeliner. I could see my eye lashes when I looked up. I felt great but did not know it was to get better.

Then the lipstick was applied, a bright red. This took me back to when I first started experimenting with makeup. Then the check blushed with she dusted on.

She repositioned my wig and brushed it like she was brushing her daughters hair. I don't know who was more please her for having her daughter back or me for fulfilling my deepest dreams. While she was doing the brushing we talked first about my name that we decided would be Mikki every time I was dressed this way, then about other girlie things like new clothes and make up. She asked me what I thought of boys and if I fancied them as boy friends. I said that I could not see my self-having a boy friend and didn't think myself as being gay. I went on to tell her that I was unsure of what I was and explained about all my feeling like the need to dress up from time to time and then the need to relive myself during the dressing up. Then Aunty did my nails putting on a pinkish colour nail varnish. When complete I had to wave my hands around which I did trying to take a crafty look in the mirror, not ever achieving it.

Next was the walking which she led me up and down the upstairs hall and up and down the stairs until I got it right. I was not very lady like but I could at least stand and walk. With that in mind my Aunty and I decided that it was not the best time step out for the first time so we agreed to have a tea party first and see how I felt tomorrow. I was so relived that she said this for I was trembling inside. All this time I could feel the lipstick on my lops which I kept rubbing my lips together to see if it was still there and looking up to get a glimpse of my new lashes.

When all was done I said "can I have a look", she lead me to the mirror saying shut your eyes and when right in front she said "open them now". Which I did and was gob smacked at what I saw. I did not recognise my self but was in heaven.

Being a bit unsure on my feet and being terribly exited we decided not to go out today but leave it until tomorrow and have a tea party instead. This was a good idea.

While she got the tea ready I went for a walk out side for the house was a secluded cottage with no close neighbours. While outside I was feeling better and better as time went on and even managed to walk better and start acting like a female. Next I went back inside and back up stairs and stood in the full-length mirror and stopped there for ages until she shouted me for tea.

I had tea but had to be reminded of my sex from time to time with "ladies don't do that" and "that is what a boy would do" but I soon got into the swing of this. We then washed the tae pots and then watch TV and chatted all night returning to the subject about being gay and the dressing up. She just listened and now and again asked questions which I had to think about for I had never talked to any one before about these feeling. I never felt the need to keep anything back even telling her that I was exited and needed to go and clean myself up. All the time she was coaching me to talk softly.

When it was bedtime my Aunty took me up stairs and showed me the make up cream and moisturiser cream I had to start using. Then see bid me a good night and I went into my bedroom to get undressed. Instead of my usual bedclothes was a silky nightie and a silky dressing gowned, which I assumed was for me. (She had thought of everything, even new clothes for the next day). I had a look and could not wait to put these on tomorrow.

I got into bed and what felt like ages fell off to sleep dreaming of the next day and other visits.

When I woke up I realised that I had had a wet dream and needed to have a shower, then I put on my wig and slippers, which were near my bed, and the dressing gowned and went down stairs making sure no one other than Aunty was there. When she heard me she shouted, " your breakfast is nearly ready Mikki come into the kitchen" I panicked when I heard the name and then realised she was talking to me. After breakfast she said I had to go and get dressed in the clothes she had laided out for me and to moisturise before I put on my make up and not to put to much on.

The clothes were slightly more conservative to the ones I had on last night consisting of a knee length floral dress and white lights and flat shoes with a small heel. Which I know was for a trip out that day. Getting washed and ready I was in the swing of it all and had no nerve at this time but I know things would change.

Putting on the dress and tights and shoes I walked easily over to the dressing table and found a bottle of foundation cream and powder ready for me. This went on and a little blusher for my checks and then I found the eye liner and eye make up same as yesterdays which I put on gently and only a few wipes of the mascara brush where as before I used to put loads on. Then the lip stick and after brushing my hair took a final look and went down stairs. She was waiting for me already to go out and with an outside coat for me in her arms. Which I took from her, and put on. She only had to adjust my hair and dab my lipstick then I was ready to go. All this time I never wanted to relive myself but was enjoying things much better.

She held her arm for me to get hold of which I did. I had been out side in the yard before but never out the gate. When we got to the gate she opened it and signalled for me to go throw. I grabbed her hand and forced myself to go throw it closing it behind me there was no going back now.

We crossed the road but we had now seen any one or no cars had passed, but that was all to change soon for when we had crossed the road we waited at a bus stop and soon the bus arrived. Aunty got on first and asked the driver for two returns to town and after paying and getting the tickets she lead me to a seat near the window. There were a few people on the bus but none of them or the driver looked at me, which I was grateful for.

We arrived in town after about 30 minutes we alighted from the bus and maid our way to the shops that were getting busy. She took me to the Body Shop first, she noticed that I had my head down and kept tapping me on my chin to get me to look ahead and not at the floor. We looked at all the make up in the shop, which normally I would look at in passing but this time I could pick up the items and try the colours etc. We bought some make up which I liked the colour of and we paid for it and went to the next shop. This was a clothes shop, Aunty picked up an about 6 items of clothing and we set off for the dressing room. Once we had the correct size I was having a whale of a time. I was getting very confident by now and was even making the purchases myself. Next we went for lunch.

During lunch Aunty said, "Did you see that boy looking at you?" which I got very embarrassed about at first thinking they know I am not a girl and then for the fact that they might even fancy me. I had to go to the toilet. Getting up from the table I nearly went into the gents but changed my direction at the last minute. When I was in I realised that this was the first time today I had been on my own. I went it to the cubical and I had to relive myself, after wards pulled up my tights and adjusted my dress and went over to the sinks to wash my hands and I even touched up my make up applying a small amount of lippy and mascara.

Going back to the table we were sat at Aunty was looking in my direction I passed that boy and gave him a smile. Aunty gave a small laugh when I sat down and reminded me of what I said yesterday about boys. I was still unsure but got a buss when he looked over to me, and better still when I replied with a smile. Aunty was a bit worried at the speed of all this so she said that after a few more shops we would call it a day and go home. I was getting carried away but calling time was no big problem for I did not want to spoil it. This we did and got the bus home and were back in the privacy of her house within an hour.

 

Having got home I was exhausted and went to lie down on my bed with a cup of tea from Aunty. There my head was in such a spin I could not relax so I had a bath and shave and went back and tried on all my new clothes followed by applying my new make up. Then I went down stairs to find Aunty who was in the kitchen preparing supper. She announced that I looked great and in the same breathe said "Simon is coming for super tonight" which took my breathe away. "who is Simon" I enquired. To which she said "The boy you smiled at today in the restaurant, it will be fun"

It took me almost 30 minutes to think of some thing to say mainly what time?

"In 20 minutes so lets get you up stairs and sort out your hair, everything else is fine"

When I came down again later she was talking to some one in the kitchen and it was the boy (Simon) I had seem earlier that day. I stood at the door wanting to go in but rooted to the spot. It was Aunty who must have seem me for she went out the door and was nearly dragging me in by the arm.

We exchanged pleasantries and shock hands. Aunty suggested we go out side for a walk in the garden for dinner was not ready, which we did. We talked for ages and I forgot I was a boy and he looked like he was getting very excited too for being a boy I know the signs. He had started to swell up down below, I was getting him excited.

He must have seen me looking down there for he tried to cover it up. I said "Don't be embarrassed its only natural. To which he removed his hands, and I gently kissed him on the lips leaving a small amount of my lipstick behind. I was going to kiss him again for he looked like he liked it when Aunty shouted that super was ready. We returned to the house where she opened the door and we went in and ate. During super we all chattered alone and after the meal I walked him to the gate and we had a longer kiss and I actually felt his very hard penis. He then left for his bus home.

When I got back in Aunty noticed that my lipstick was smudged and she told me that she had seen the lippy on his lips earlier. I told her that I enjoyed the kiss and feeling his hard penis and asked what should I do about it. She did not know and I cried like a girl for the first time bringing black rivers of tears and mascara down my checks.

It was never the same after that and I never saw Simon again and I never returned to her house.

I would like to say that I never cross-dressed again but I do some times when my wife and kids are out and I would also dream of days away.

  

  

  

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