I walked into the shop. It was full of a variety of long and short dresses and gowns made from satin and silks in a range of colours and styles. A strong perfume smell struck me as i entered, the door closed behind me and the immaculately dressed owner walked forward to greet me.

‘How can i help sweetie’ she said with a slight ‘knowing’ grin.

I swallowed ‘I would like to try on a dress’ i replied, complying with the dare.

‘Oh no’ she said ‘we don't ‘try on’ dresses here! My clients are here for a full fitting and transformation to help them discover their true beauty ready for their special day, i pride myself on a full experience to make sure the dress you choose is absolutely perfect, is that what you'd like?’ She said in a stern yet welcoming tone.

I cleared my through, now dry with nerves and anticipation ‘I would like a fitting please’

‘a full transformation?’ She asked.

‘Yes, as you said, a full fitting and transformation’ I was swept up in the moment still not really sure what I was letting myself in for.

She walked behind me looking me up and down, locked the door, turned the store sign to show ‘busy, please try later’ to the outside world and stopped behind me ‘let’s get started then young man, or should i say ‘girl’?!’

I gulped, but had come too far to walk away now.

Before i continue with what happened next….i should explain!

*****

Three weeks earlier…….

We were a close group of friends, three boys, three girls. All the same age, we were often compared to each other as we were the same age and close in height and, apart from obvious differences between the girls and boys in our body shapes, we were the same size. We had great fun knocking around at college and evenings and weekends, a close group.

It was halloween and we decided we’d have a costume party. This is where it all started. Russ was a bit of a joker and decided it would be fun if we chose each others outfits. To make it more exciting it would be decided ‘blind’. We each had to buy an outfit and everything to go with that outfit and we would randomly choose, or select, what we would be wearing for our party.

I bought a pirate costume, complete with accessories and sword and put it all In a plain bag. i took it to the party where everyone else had done the same.

We agreed an order to choose and also agreed we would take a bag each and open at the same time that way we would all discover our personas for the evening at the same time before changing and starting the party games.

I took a bag, it didn’t feel very heavy but i could tell there was something a bit lumpy in it and also a few lose plastic sounding items as the bag moved.

On the count of three we opened the bags.

Russ had a vampire outfit with a cape and accessories, white face paint and complete with false teeth and fake blood.

Jon would be wearing a zombie outfit, similar face paint and a green wig, they looked at each as though they had worked it out between them.

Ruby pulled out a cowboy outfit, ‘a bit weird for Halloween’ she exclaimed ‘but ok!’

It hadn’t escaped me at this point, three boys, three boyish outfits. I should have grabbed my my pirate outfit but it was too late, I had made my choice!

Daisy next, she got the Pirate, ‘Ha, ha’ she said.

Just Cheryl and me to go, Cheryl went first.

A sexy (really sexy) vampire Snow White cross over. Dress, high heels, head piece, make up and underwear including hold up stockings and satin covered shoes. She was pleased.

My turn…I put my had in the bag seeing a flash of red and white, the material felt soft and cold, shiny too! I pulled it out and the girls laughed, the boys leaned in to see what I was holding. It was a satin cheerleaders dress. ‘Oh my’ Ruby exclaimed. I looked deeper and pulled out matching red satin underwear, shiny red high heel shoes and a blonde wig. Also in the bag a red nail varnish, some other make up and notably a tube with a red lid, it was high gloss ‘moisture drench’ deep red lipstick.

‘Ok, let’s get changed’ said Jon

‘Hang on’, I said ‘I can’t wear this!’

‘Sure you can’ said Cheryl, ‘we can get ready together and I’ll help you. Anyway, I dare you to be our cheerleader for the night! No backing out from a dare!’

‘I double dare you!’ Said Ruby ‘and I’ll paint your nails while Cheryl sorts your hair and make up’.

‘We all dare each other to wear the outfits we’ve ‘chosen’ ‘ said Russ

What could I do. Everyone was up for it. I thought I had the rough end of the deal but the girls just gushed and enthusiastically started saying how lucky I was I’d have a chance to be dressed all beautiful and pretty while others were monsters and covered in fake blood.

I changed, first the underwear, soft, stretchy and shiny the panties fitted ok despite being a different shape to what I’m used to. I tried to put the matching bra on but couldn’t fasten it so Ruby had to help. Dress slipped over my head. Again this was soft, shiny and stretchy and came to my mid thigh. A pair of over the knee stockings in white were also included and although I struggled I managed to pull them on ready for the high heels that just fitted me. I felt really silly as I stumbled in the shore.

Cheryl fixed my hair while Ruby painted my nails. The wig was pinned to my real hair and arranged in bunches, one each side of my head with a straight fringe. She then applied generous amount of blue eye shadow, blusher, mascara, eyeliner and perfume to make me feel really girly but made me apply, then reapply ‘my’ lipstick until she was satisfied. She took it from me to complete her own look applying generous amounts before she gave it back to me. The dress had very small pockets just at the waist and Cheryl instructed me to keep the lipstick close as I would need to touch it up as the evening went on the same as she would. She looked beautiful in her Snow White dress.

Everyone cheered when we walked into the lounge. We were all dressed and the drinks started flowing. During the night we set each other little dares ‘drink a raw egg’, ‘call one of your contacts and tell them a random joke’, harmless things. I had two notable dares. One was to walk to the end of the street. I did it, I only saw a little old couple who just mumbled something, that I couldn’t really hear, at the sight of me and a couple of younger kids who wolf whistled and asked me for my number.

A second dare involved me taking my make up off and applying it myself, sounded easy but it took ages while everyone watched and jeered at me. I had to have a few attempts but in the end I did a good job and the girls said I could share theirs anytime. Ruby whispered in my ear a few times during the evening. Telling me I was her ‘little bitch’ from now on and how she would have some fun with me but I wasn’t really sure what she meant, assuming she was just getting carried away and a bit drunk.

Finally, one more dare was added last minute and I had to make up a cheerleading routine. It was such an embarrassment but the whole room enjoyed it and we all agreed the evening was great fun.

As we pulled our coats on to leave (yes I was going to walk home in the dress and heels!) Russ yelled out, let’s do more of this, let’s have a weekly ‘ultimate dare’ challenge. The terms of the challenge needed to be sorted but we all agreed to it.

I got home about half hour later and before I undressed and slipped into bed, I found myself staring at my image in the mirror as I sobered up. Oh god, I knew some photos were taken during the evening and started to worry about what people outside of our group might think if they saw them.

That was the first night I dressed fully as a girl. It wouldn’t be the last!

To be continued.