Robyn’s First Dress

First Dress


It was the summer of 1972 and my fiancee and I had gone for two weeks of sun, sand and sangria on a package tour to Ibiza. Linda and I were getting married that autumn and this was our first real holiday away together, just the two of us with no friends or relatives to get in the way.

I have been a transvestite for as long as I can remember, at least in the way that I had always fantasised about being dressed as a girl. It was a compulsive dream but not a compulsive act. Although I was 19 at that time, I had never worn a frock.


On the first morning everyone was gathered together in the hotel lounge and told about the entertainment on offer during our holiday. There were trips across the island here and there, barbecues and discos, but it was one in particular that really excited me – a his ‘n’ hers party on the first saturday night.

“It’s not compulsory of course,” said the bubbly rep with the long brown legs, “but most couples join in and it can be a real giggle.” I could hardly believe my ears as she said it, but she did… “the girls come as the boys, and the boys come as the girls.”

Nearly thirty years later, I can remember that moment even now, as if it had only just happened. Linda was all for a bit of fun and we duly booked on almost every trip going. To my absolute delight, she was also keen on the his ‘n’ hers party. I tried to play it cool, but inside I was so excited I could hardly speak, and there was still four days to go…


Somehow I kept myself together for the first two days, and never mentioned the party, but eventually I just had to talk about it. We had just been out to look at the place were they filmed South Pacific and were coming back to the coach when I asked Linda what we were both going to wear. I was so nervous I was sure she could tell. I just remember her saying we would have to sort it out when we got back, and I was too scared to say anything else.

When we returned that afternoon she was as good as her word. I had the most wonderful time of my whole life, something I will never, ever forget. Linda soon chose the shirt and trousers she would wear on the night, and then it was my turn to be kitted out. I was in absolute heaven.



Real Life Transgender Stories

I was taller than Linda but not much wider, so her dresses fitted me okay. She tried me in three or four different dresses, then various combinations of blouses and skirts, then back to the dresses and round again, over and over again while she made up her mind.

This was what she was like when she was shopping for herself, never able to make up her mind and it would normally drive me mad. But this time I was the model, in her pretty clothes, and for once I wasn’t complaining.

┬áIn the end she decided on a long-sleeved Indian print dress in flowing cotton, a hippy style that could go well with sandals – shoe size was a problem, and there was no way I could have fitted into her size fives…

So, that was my first dress. It was a mixture of blue, lavender, and pinkish hues in a soft, soft material that seemed to float with me as I walked. For me, it was a dream come true. By the time saturday night came I was so hyped up I was really scared I would do something silly, like confess to Linda or something like that, but I didn’t, not that night anyway – I just had a ball!


Linda seemed to be enjoying herself as well as she made up my face, not to Transformation standards admittedly – there was no beard cover and she didn’t even bother with foundation – but just wearing lipstick, rouge and eyeshadow was a big enough thrill for me. I remember I couldn’t resist continually licking my lips to remind myself that I really did have lipstick on.

I had long hair in those days, so that was no problem, but Linda set it off with her wide straw hat with a pink silk scarf that tickled the back of my neck. When I looked in the mirror I thought I was the image of Marianne Faithful, although the lady herself could well have sued for slander if I had said so publicly. I half murmered it to Linda and she agreed, with a laugh, that she would call herself Mick.


As Mick and Marianne I was sure we would win first prize, and of course if this was in TV fiction we would have done. But as it happened, we didn’t. The honours went to a couple we didn’t know, who were incredible. He must have been a TV, and she must have known.

He was only about 5’6″ with natural, shoulder length blonde hair and a neat little figure most of the women would have died for. He had on a bright red mini-dress with short puffed sleeves and knee-high boots. He was supposed to be Nancy Sinatra, and his wife, slightly taller than him, was Frank.



Nowadays, being a bit braver on the TV front than I once was, I would have asked him all sorts of questions, but then I didn’t want to draw attention to myself. Perhaps if he was a real TV and is reading this he may get in touch and put me out of my misery. I’m still very curious as to what his wife thought about him being so much prettier than her…


To complete my dream I would have given anything to have made love to Linda while we were still cross dessed, but there was no hope of that. I tried to kiss her but she wouldn’t have it – “I’m not a lesbian, you know”, she said curtly. End of dream.

That holiday was not only the first time I dressed, it was also the last time for many years. Linda and I got married, and divorced, and although I was living on my own I still never came to terms with myself enough to actually buy my own clothes. That had to wait until I discovered Transformation.

I now have my own wardrobe of dresses, skirts and suits and go out regularly about the town. However, Linda remains the only woman ever to have dressed me up, and despite our later quarrels I will never forget her for that. Ibiza is always in my mind.


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