Linda’s Transvestite Story

Linda’s Transvestite Story

For many years I was a closet tranny, never venturing out of the door or dressing in front of my family, but when I got to my middle forties I decided to pluck up courage and go out at night when my family were away. I had secretly been buying clothes for a long time, but if I was to start going out, I had to try to do it properly. I already had a nice black skirt from C&A, A-line as was the fashion in the early eighties, and knee length. I bought a matching blouse from Paige’s and a black velvet jacket from Marks and Spencer. I’ve still got a very old wig which my wife had left to be thrown out.

I needed to get something to walk in as the only shoes I had were from the sixties or a pair of very high and strappy stilettos which were too awkward to walk in for any distance. I did the rounds and finished up with a pair of 3 inch stilettos from the Clock House at C&A. Just an ordinary little black court shoe – I’m a size six and a half.


I already had some good underwear, a few accessories and some makeup items. I just bought a a nice new pair of black tights and I was ready to go!

I spent the afternoon getting ready – having a bath, shaving my legs and body, etc, then it was time to get dressed. I took my time with my makeup (which I’m still not very good at) but at last I felt finished. I was very nervous, but my mind was made up. I went downstairs, poured a martini and waited until the lights had gone off in all the surrounding houses. I live in a small village on an even smaller estate, where everyone knows everyone else. It would be disastrous to be found out as I’m sure all closet trannies feel.


At last the coast seemed clear. I gingerly opened the front door and ventured out onto the step. I live in a large circle at the end of a cul-de-sac and had previously decided to go for a walk round the block, which is about half a mile.

The three inch stilettos were really comfortable and I had no trouble walking in them. After all these years they are still my favourite shoes. I have had the tips renewed several times.

I enjoyed feeling the air around my legs and the movement of my skirt. It was lovely.

I made it safely back home, poured another martini and sat down to savour what I had just done. I had done what I had wanted to do for decades – I had been out as a woman.


I’ve been out many times since – over a hundred, but nearly always on my little late night walk round the block. A few times I’ve got a little more adventurous and taken the longer walk down to the main road and the bus stop.

Eventually I wanted more. I wanted to be seen, but not found out. I chose a rainy night and went out a little earlier than usual. The rain was useful as I could use my umbrella to hide behind. Still just on my little walk round the block. When I was nearly back home a neighbour drove past in her car. She had seen a woman walking up the road with an umbrella and shoulder bag. Still in the three inch stilettos. Diane had seen me and never gave it another thought. I felt great!

Shortly afterwards I went out in my pale blue flowered sundress under a different black jacket with a ‘Classic Woman’ label inside. Even the label makes me feel good! My dress has a wide mid-length skirt and before I went out I wasn’t too happy with the way it was hanging so I put on an extra petticoat. That made me feel a lot happier.


By that time we had had new and much stronger street lighting put in our road. Nevertheless my confidence was growing and I set off without worrying. I had only gone about thirty yards when I became aware of a young neighbour walking along on the other side of the street. He was looking at me. I just carried on. Stuart must have thought I was worth looking at. I was pleased I’d put on that extra petticoat! Naturally, I was wearing the three inch stilettos again. He probably heard me coming before he saw me!



As we went through the nineties skirts got shorter and some of my older dresses were again wearable. It was fabulous to go out in a short skirt. Something which I had never dared do when I was younger. No, I don’t dress like a teenager, but its acceptable now for the older woman to wear things which are in fashion. I bought a couple of new skirts to bring me up to date – a plain black velvet and a green/grey check from M&S and a short black waist slip from BHS to go under them.

One night whilst wearing my black skirt I went a bit further than usual along the main road to the post. (I really did have an important business letter!) A few cars passed and I felt terrific at having been seen in a short skirt and heels. I was wearing a pair of sling backs which didn’t hold my heels very well and I hobbled quite a bit. It was winter so I was also wearing 60 denier black tights which had become the in thing.


As I was walking back up the entrance road to the estate, which is quite steep, I was suddenly flat on the ground. I banged my head quite badly on the footpath. My wig came off. As I got slowly up, I felt a dampness and realised that it was blood from where I had hit my head. The sling backs had stayed on, so I put my wig back, gathered my bag and walked as fast as I could back home. The walk was quite painful.

When I saw myself in the bathroom mirror I couldn’t believe the size of the gash above my right eyebrow. It was deep and looked as if it had been done neatly with a knife. I still have a slight mark. I eventually managed to stop the bleeding, which had been quite profuse and stained my blouse badly, and started to get undressed. To my amazement I had badly grazed both knees, but the 60 denier tights were unscathed!


I was lucky not to have been knocked out. What would have happened if someone had come across this unconscious, unbewigged but fully dressed tranny doesn’t bear thinking about. The next day I went to the doctor for a checkup and was pronounced fit but lucky. He asked if the wound had been stitched, as it had come back together so neatly.

It was the second time I had fallen while dressed. The first time was when trying to run in those strappy four inch stilettos I mentioned earlier. Needless to say, I don’t go out walking in sling backs anymore!


My desire to dress was still as strong as ever, but for a while I didn’t actually do it. Then I went out and bought a pair of boots from Shoe City and could not resist going out in them straight away. They are so comfortable. They are the kind which come just up to the back of the knee. I walked quite a bit further than ever before and again was seen by about ten people in cars who took no notice.

On the way back I met some other people out walking. I could hear male voices coming towards me and I felt vulnerable both as a tranny and as a woman.

I decided to cross to the other side of the road, probably as any other woman would. They just passed by deep in their own conversation and never bothered with me. Another car went by and I felt reassured.


While I was walking back up the hill towards where I had previously fallen, another car came up from behind and stopped right alongside me before turning towards a private drive on the opposite side of the road. I carried on walking. I heard a female voice which I recognised. It was Denise saying goodnight to her boyfriend.

They must have had a really good look at me, being less than four feet away when the car had stopped beside me. I was wearing natural coloured glossy tights which could be seen above my boots and below my skirt, which finished just above the knee.

This was my closest contact yet and again no one seemed to bother. I must have passed for a woman without a second thought.



Again I didn’t dress for a while, but the desire remains so strong. As I’ve got older I have had to go up a dress size. My favourite at the moment is a plain little black number which I bought in Littlewoods. It hangs above the knee and is tailored from the bust.

Yesterday I decided it was time to see if I could still get into into it. I had bought a lot of new accessories while on holiday in Majorca in the summer. New rings and clips, an ‘L’-for-Linda chain, a new watch as my old one had given up and a lovely Moschino shoulder bag with a leather and chain strap. I had also bought some new fashionable ankle strap court shoes from BHS which I wanted to try.


Yes the dress still does fit me. Its a bit tighter that I would like (what woman doesn’t think that), but still very much wearable.

So here goes for another night out. Having read the good advice on the Transformation web site, I wanted to go out earlier and be seen more. It took a while to get ready. As I said before, I’m still not very good at makeup, and if more people are to see me I want to look my best.

Under the dress I first put on my Wonderbra knickers into which I always put a pantie liner. After that comes a lovely M&S underwired body which is really comfortable. It doesn’t open at the crotch, which makes it difficult to go to the toilet, as I have to get virtually undressed. It’s not too bad if I’m wearing a dress with a long back zip, but most inconvenient if I’m in a skirt and top!

Then come the 60 denier tights I mentioned before (it’s still winter) followed a lovely little full slip which I’ve had for years, but it is very pretty and the right length to go under the dress. All in black, of course.


At that stage came the makeup, followed by the dress and the wig. Its time I bought a new wig. I’ve been looking at the Transformation catalogue and quite fancy a Selina in medium brown. Must make a point of visiting Bury Old Road again!

I topped off my ‘Classic Woman’ jacket with a nylon scarf and a fashionable little round hat from M&S.

After all this it was later than planned when I was ready to go out. I’ve recently had new windows and doors fitted, so I had to transfer the correct key to my ‘Linda’ keyring. I set out but had only gone a few yards before I realised that the new ankle strap shoes with 4 inch heels were not for walking in yet. I’ll have to wear them around the house for a while.


Back home I decided upon Plan B, which was to get out my knee length boots. This done, and after renewing my lipstick and a few shots of my new ‘Woman’ perfume which I had also bought in Majorca, out I went again. Round the upper part of the block and down towards the main road. The boots were not quite so comfortable as I remembered them, but probably because it had been a long time since I had worn heels.

I got down to the main road and heard male voices. Two young lads were across at the bus stop. I realised that as I was later than I intended they must be waiting for the last bus back to the next village.


As I approached I heard a wolf whistle! For a second I thought I had been read. Then I heard two more wolf whistles. There were no jeers or cat calls. This was too good to be true. I was genuinely being wolf whistled! Like any other woman, I held by head high and walked on. I had enjoyed the experience. I hope it happens again!

A couple of cars passed as I walked on, then the last bus. I walked further than I had ever walked before while dressed. I was enjoying myself. But soon I realised I was tired and decided to turn back. I have a plan for very long walk, but that will have to wait.

I got back to the main road and headed for home. More cars passed without incident and I was happy. I was a little apprehensive as I approached the bus stop, but the boys were not there. They must have gone home on the last bus as I had surmised. I wonder if they looked out for me as the bus drove by?


As I started to cross the road back to our estate I heard another car coming. I decided I didn’t want to wait to let it pass so I crossed. Just as I got to exactly the same place as I had heard the first wolf whistle, the car passed. After (only a split second) it had passed there was a toot on the horn!

Three wolf whistles and a horn toot! This was my lucky night! The lads in the car must have been on their way back from the pub and had seen a bird! The short dress and boots had definitely done their job!

I walked back up the hill to the house and reflected on a wonderful evening out. Obviously I’m still not too old to excite the male when properly dressed and looking good! The wolf whistles and the toot from the boys in the car helped me to realise what it is really like to be a woman!

Lots of loveLindaXX

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