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.
Ultimate Dare - Part 2: Time for my Ultimate Dare
I was reminded of the events of that Halloween evening, and our costume party, frequently in the days that followed.
The next day i woke up with the make up still on, albeit somewhat smudged, and i was still wearing the satin underwear and knee high stockings. The cheerleader outfit and wig were on a chair in my bedroom.
I cleaned up, changed and folded the dress and other items placing them in the top drawer of my chest of drawers and nothing much more happened that day.
In the Monday i received a couple of photos by email from Ruby, the email just read ‘u and me, our secret, don't tell, let’s have some fun. If u do as i ask of u we will have fun and save any further embarrassment’ and on the first one a photo of me, already fully dressed with make up on holding the lipstick to my lips pouting, I remembered posing like that for Ruby and it was before the night really got going so I looked freshly made up. The second was a still from what appeared to be a video of me in the uniform as I was getting dressed and I knew just before that I stumbled wearing just the underwear and had to adjust myself. Thinking back I hadn’t realised anyone had seen and suddenly imagined how it must’ve looked and if it had been captured on camera I would be mortified if anyone else saw it. I knew I was screwed and should do as asked if i didn't want these being shared!
On the Thursday i received a small parcel. Inside a note read ‘4 u my little pet, wear these on Saturday, under your normal clothes. I won't tell’. It was signed with a lipsticked kiss. In the package was a pair of purple satin ‘boy-short’ style knickers that were very shiny and stretchy and edged in a lace band on the legs and waist, and and a tight fitting matching strappy cami top in the same shiny stretchy material.
I held them up, looking at them for ages wondering why she would make me do this and what she could want with me wearing these things. Also worried what this might lead to but also strangely curious if they would fit me. I didn't try them until Saturday, the next time we had all agreed to meet for the first ‘ultimate dare’ evening. They underwear did fit me and felt ok so I pulled on jeans and a t shirt over the top satisfied they couldn’t be seen and headed over to Russ’s house.
When I arrived Ruby pulled me to one side and, with a knowing look, asked me if I had followed her instructions. I nodded. ‘Show me!’ She said firmly. I lifted my tshirt. ‘Ahh, very good sweetie’ she said in a kind soft voice, ‘now what about the rest?’ I lowered the belt of my jeans so she could see the lace band of the knickers proving to her I was wearing them and she gave me a big kiss direct on my lips leaving me surprised and I suspected with some red stain behind from her full glossy lips. She held up her phone showing me a snippet of the video she had. It was worse than I expected with me flouncing around in the underwear saying how nice the clothes felt. I remembered Ruby suggested I said that but the video hadn’t picked up her prompt, just me saying it. She told me it was over 5 minutes long and would be embarrassing for me if it got out to others.
We quickly moved when Russ came in the room asking us what was going on. We both just said nothing but Ruby winked at me.
We all sat around the table, drinks started flowing, and we started our little game of dare by the boys asking the girls for secrets they know. Ruby looked me direct in the eye as she started ‘I know someone in the room is hiding something, it’s all to do with what they are wearing!’ She said. Oh god! What if she exposed me wearing the sexy undies, I’d have to show everyone and would never hear the end of it! ‘He…’
I shook my head while we maintained eye contact.
She smiled
‘He, is…wearing…my….favorite bands tshirt!’ (Phew!) looking at Jon and revealing that the ‘guns n roses’ tshirt he was wearing was in fact her favourite band. I was hot, sweaty, worried and relived.
Ruby mouthed ‘saved you! You owe me!’ At me. Gulp!
More stories, more fun and a few small dares later we got to the matter at hand. We would each set dares for each other. Once we agreed we could not refuse to complete the dare for fear of a forfeit that promised to be more difficult to complete than the dare itself. Dares were considered to be a necessary part of our group now. I didn’t have any other friends and felt lonely at times so agreed to play along.
We each had a dare that night. Mine was to climb in to next doors garden and take a towel off their washing line and post it through their front letter box. Easy!
Chloe had to eat a smoothy made with all sorts of disgusting things. I am not sure I could do that but she did it ok.
We then decided we would each have an ultimate dare, taking it in turns, one each week, decided by the group.
Ruby’s was first. Her ultimate dare was to spend a week wearing horrible baggy clothes, no make up and no products or perfumes. Now, Ruby was gorgeous, and took immense pride in her appearance and hated opening the door to anyone unless properly dressed so to spend a whole week like that was mortifying to her. But, she did it. She didn’t bother me for the whole week apart from once when we were walking through town she just whispered ‘I’ll get you back! Opposites’ and winked. A few times kids walked past and called her tramp or said they didn’t realise how ugly she was. It was mean and uncalled for but I did find myself laughing at a few things that were said, and that annoyed her even more ‘I’ll get u back, bitch’ she said.
Her week was over and it was Jons turn. I won’t go into details about everyone else as it’s a story about my ultimate dare, safe to say they all did what was set for them and as a group we really got close. During this I had grown apart from Russ and Jon and the girls were a bit hot and cold with me. Ruby always seemed to be the one that took most attention of me. I desperately wanted to stay in the group and felt I had to play along with the dares.
One week Ruby made we wear an all in one satin bodysuit under my clothes. It was tight but stretchy. It had thick straps over the shoulders and frills round each leg with feint ‘sexy girl’ writing on it. Ruby was so happy when she realised I was wearing it and said how proud of me she was and that doing it was ‘to keep me on my toes’, having received another email and more stills from that night of the cheerleader dress that I definitely didn’t want shown, I didn't think I had a choice. Another time I had an all In one sheer body suit or body stocking to wear. I felt really hot all evening much to Ruby's amusement but no one found out. She was nice to me all along, but I could tell she was brewing up for my ultimate dare.
One of the smaller dares I was set along the way was to have a manicure. I protested and said I didn’t see why mine all had to be about getting dressed up or girls stuff. Everyone laughed and joked there was plenty more they could think of. In the end I got out of going to a nail salon but Ruby did insist on me having my nails manicured by her, in a light pink that barely showed, but I was conscious of it for a week until I was allowed to take it off. No one said anything.
The blackmail emails kept coming too. Small hints and suggestions of what might happen if I didn’t play along. By now I was too far into the dread that comes with not wanting the wider world seeing you in an embarrassing predicament I felt I would do anything to avoid that.
My ultimate dare was next.
Each day of the week before I was due to be given my ultimate dare, to be executed the week after, I received small parcels.
Monday - a pair of ivory satin Brazilian knickers with a small love heart stitched to them on the side in pink. A note that said ‘I’ll keep our secret if u save me for later’
Tuesday - a matching bra, same note
Wednesday - a matching suspender belt. Same note.
Thursday - a pair of ivory seemed stockings. Same note
Friday - a set of silver jewellery, with a pink heart pendant that had ‘bride to be’ engraved on it and a bracelet that had ‘dreams do come true’ engraved on a pink band across it. Same note.
All of these packages were stored in my top drawer with the other ‘gifts’ I’d been collecting.
Saturday. A letter. ‘Hey honey, my sweet pet. today you will receive your ultimate dare. Do not object, and you must carry out the dare as requested or I will release everything I have, the photos and video, over the next few months. I may even suggest our group disown you! I love u and I want to to enjoy your ultimate dare, what I’ve been sending is all needed on the special day you will soon be having to compete your ultimate dare. If you go along with the dare, I will delete everything and take back all the lovely things I’ve been sending you and that will be the end of it. For Today, please just wear the purple set i sent before under your normal clothes to prove to me you will see this through. I know you still have them. Luv, Rx’ with a winking face and lipstick kiss on the base of the letter.
I felt like I had no choice but did now see an end to this. I would have to follow through my ultimate dare but I didn’t yet know what that was. I was about to find out…..
We gathered that evening and had a few drinks and chatted while we waited for the inevitable. Ruby checked i was wearing the purple set and seemed pleased I did as asked, rewarding me with a kiss.
When the time came Chloe gave me an envelope that looked like a wedding invitation. I opened it. There was a card inside with silver writing, It read;
******
x Welcome to your ultimate dare and ‘special day’ x
You are invited to a dress fitting at Sarah’s Bridal Boutique!
You will go in to the shop and ask to try on a dress. The style and colour of dress will be up to you or Sarah, the owner. It must be a bridal gown or bridesmaids dress and include satin, lace, a corset and gloves. You must also be wearing suitably matched shoes with a heel.
We want to see three photos of you wearing the dress, one taken from the front, one from the side and one from the back. You must also show us a photo wearing the shoes, and that will complete the dare.
******
Everyone laughed and said what a great dare it was. Ruby, who was sat beside me, whispered in my ear ‘you must also wear the undies you’ve been sent this week and I want at least one photo of you in that lingerie set as well as those of you in the dress, then the dare will be complete’ she pulled away with a smile and a wink.
The rest of the evening was a blur and I didn’t sleep well at all the next few days.
Before I knew it, It was a Saturday, the day I was to complete my ultimate dare. I woke up early and showered. I walked back to my room, naked, wearing only dread and fear and a small amount of excitement for what the day might bring.
I slipped on the satin ivory knickers, then struggled with the bra but managed to fit it in the end, it wasn’t the first time I’d had to put a bra on! The Suspender belt was new to me but not too difficult, it took a while to attach the stockings. As I clipped the hem of each to the clips on the belt, I could feel the stockings tighten on my legs. I would feel them with every step. With The bracelet and pendant on I stood in front of the full length mirror wondering how on earth I got into this predicament. I took a photo to satisfy Ruby’s part of the dare.
I then pulled on a pair of jeans, t-shirt and trainers. I could feel my new lingerie with every step, as I sat and as I stood and I had difficulty keeping the ‘bride to be’ pendant hidden under my t-shirt but managed it on the bus. I stepped off and stood in front of the shop ‘Sarah’s Bridal Boutique’. I was here, moment of truth.
I took a breath and stepped forward….
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 throat, 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.
To be continued…..