Crossdressing with My Boyfriend and Girlfriend
(The Misadventures of Timothy)
Tim's mom and sisters try unsuccessfully to persuade him to be a replacement flower girl at a family wedding. He thinks he has managed to get out of the dressing up, however the reality turns out to be far worse, but at least he makes new friends.
This is the first part of what will be a six part story. It is rewrite of a version I recently posted on another site. I received such a lot of nice encouragement and advice from authors who post on BC that I am posting the rewrite here. (You know who you are, but I must give special mention to Angel O'Hare)
CROSSDRESSING WITH MY GIRLFRIEND AND BOYFRIEND
(The Misadventures of Timothy)
"Come into my room Tim, it's time to start getting you dressed,"
It was my sister Cathy. It was the day of my eldest sister Janette's wedding, which was going to be at two that afternoon. She’s getting married to Mike, who she met at college
I'd better explain that I'm Timothy, eleven and a half years old and I'm going to be the ring bearer at the wedding. It didn't start out like that though. Janette, as well as wanting four bridesmaids, had also wanted four flower girls, all of whom were my cousins. Then two weeks ago, Sharon, one of the flower girls had an accident when riding a horse and broke her leg and it would have to be in plaster for three weeks. Therefore, Janette got all panicky about her four flower girls. There were no more suitable relatives and the mom had already made all the dresses. Thus, it was that mom called me into the lounge and said they had something they wanted me to do.
"Timmy, we wouldn't ask you this if it wasn't that Janette is desperate", said my mom, "but we want to ask you a big favour."
"OK, let me hear it," I replied, cautiously.
"Well, you know how Janette wanted to have four flower girls at the wedding, well, since Sharon's accident; we have tried really hard to find a replacement, so we can have four girls to balance with the four bridesmaids. But we can't find anyone who is available and who could fit into the dress we had made for Sharon," mom explained.
I started to get a sense of where this was heading. "But you can't mean..." I started.
"Now, hear me out," said mom. "You are the same height and build as Sharon, and you know how well you played the role of Dorothy in your schools Wizard of Oz play last term."
"You really were so cute! Nobody ever would have known you weren't a girl, if you weren't in a play," said Cathy who had attended the show.
It was bad enough trying to live the Dorothy part down at school, now they were bringing it up to try to make me dress up again. My minds eye flashed back to last term when I was pressed into playing the role after a call for volunteers drew no response.
"Right then," said Miss Cartwright the Drama teacher. "I will pick someone,"
She looked around the class and her eyes rested on me. Now, I know I have a soft rounded face and long eyelashes and longish blonde hair, and some of the boys had in the past called me girly, so I dreaded what might happen. Sure enough, she walked up to me, cupped my face in her hand.
"Yes, I think we've found Dorothy! Timothy, congratulations, you have the role." She said.
The rest of the class sighed with relief as I cringed.
So it was six weeks later that I stood on the school stage in a blue gingham dress, white socks and glittery red shoes, two blonde braids pinned into my hair, and wearing stage makeup, singing 'Somewhere over the Rainbow' in front of 500 people including all my giggling classmates. Worse, my mom was into dressmaking and amateur drama so she had taken care of the costumes and makeup herself, so I really did get the full treatment. She made me rehearse at home in the costume, "to get used to it.”
Now I stood in front of the three of them, I realized I had to stop this right there and then. "There is no way I am going to dress up as a girl ever again! I still get called Dorothy at school by some of the kids, so if you think I'm going to put on a dress in front of the whole of our family and friends and everyone who is coming to the wedding, no, you are mistaken, I won't and you can't make me."
Janette looked crestfallen, but didn't say anything. Cathy just looked disappointed she was always needling me about my small size and how pretty my hair is.
My mom came back with, "No one will force you Timmy! “ It was just a suggestion so that nothing will spoil Janette's wedding. We know you don’t want to do this, but it would help your sister on the biggest day of her life!”
"Mom, I'll do anything to help that I can, but please don't ask me to wear a dress, it is just something I won't do in front of everybody."
"Well I have to say I'm very disappointed and so is Janette. Do not expect any help from me next time you want something. You had better think this over very carefully. We will talk about it again tomorrow. Now perhaps it's time for you to go to bed."
It was only 8.30pm, but I took the hint and went up to my room. I could hear them talking for ages afterwards and even some laughter from Cathy, and after a while, mom, so I hoped things weren't quite so serious after all.
Next day, Janette came up to me. I always got on well with her. She was very different to Cathy, always kind and considerate.
"Look Timmy, I'm sorry about yesterday," she said, "I realise it was too much to ask. I've rethought what we can do, instead of four flower girls, I could have the three, and you could be a ring bearer."
I thought back to my cousin Charlotte's wedding last year where a boy, he must have been about seven, had carried the ring on a satin pillow in the service. He was wearing a boy’s tuxedo, he looked a bit overdressed with bow tie and black shoes, but at least it was not a dress.
"Well I suppose that will be alright, I do want to help you have a nice wedding," I said
"Oh, thanks Timmy, that will be wonderful, you will make a great ring bearer," upon which she grabbed me and gave me a peck on the cheek.
I guess I should have been alerted when 3 days later Cathy came by my room and said, "Moms nearly finished your ring bearer costume, and you are going to look very smart."
"Well, it will be a lot better than a dress," I replied.
"Oh, yes, a lot better," she chuckled.
So now, she was calling me into her room. "Why can't I get dressed in my own room?" I asked.
"Because you will need help with one or two things," Cathy replied.
"Oh, OK then have it your way," I said
"Now, I want you to promise not to complain about anything. You got off wearing a dress and you promised Janette you would wear the ring bearer costume, right?"
"Yes, OK, I won’t complain - I want to help Janette have a nice wedding." I replied.
"Good boy," said Cathy, "now strip down to your underpants and we'll get started."
When I hesitated, she said, "Timmy, you run around to and from the bathroom in your underpants, I see you in your swimming costume, what's the problem?"
"Oh, nothing, I guess, it just feels odd doing it in your room," I said as I slowly took off my T-shirt add jeans, socks and sneakers.
"Oh boxers," she said, when I had finished, "don't you have any Y fronts or briefs?"
"No, I only wear boxers."
"Well, with this outfit you will have to wear these," she said, walking over to her dresser and picking out a pair of yellow panties edged in white lace.
"No way," I said. "I'm not wearing those," I yelled
"Timmy what did you just promise, not to complain, right? You don't want to spoil Janette's wedding. No one will see them, what's the problem?"
I gave up. "Oh, alright, give me them." I turned round, removed my boxers, and slowly drew the panties up my legs. They felt very snug and smooth as I pulled them on.
"Right, that looks nice," she smirked, "now let's try these." She held what I thought were white girl’s stockings, but as she unrolled them, it became clear they were white, shiny tights.
I made as if to complain, but before I could speak she said, "Not a word, you made a promise, let’s just hear no more complaints."
"I was just going to say that I said ‘no dresses,’ you wear tights with dresses, what's going on?" I asked.
"Don't worry little Timmy, you are wearing pants not a dress," she told me.
"Come on let me help you to get these tights on."
She rolled them up and unfurled the tights on to each leg while I sat down. Then she told me to stand while she pulled them up around my waist.
"Now, pull them up tighter, while you jiggle around, till they are comfortable under your bum. You might want to push your little boy parts underneath you a bit," she said smiling.
I turned away, wriggled into the tights, and pulled myself tidy underneath by tucking myself in. I looked down at my legs, they looked so long and shiny and very, very girly, but at least they would be covered by my pants.
"I don't see why I need to wear tights if I'm wearing pants," I said to Cathy.
"You'll see why, right now," she replied.
She held up what looked like a pair of shorts, but they were made of a satin material and were a kind of apricot orange colour with a lace fringe around the bottom of the legs.
"They are what are called Knickerbockers, or pantaloons, they are what men wore in the 1800's. They are made out of Sharon's dress material. All the flower girls are wearing orange satin dresses so you will match in with them and look really cute."
"But they are terrible, they have lacy bits and it's an awful colour!" I wailed.
"Timmy, I won't say this again, no more complaining, we need to get moving, put these on," she yelled at me.
I took the garment from here and reluctantly stepped into it. I was appalled at how silly it looked and as I pulled it up around my waist, I saw that it only came down to five inches above my knees so that I would be showing most of my legs in the glossy white tights. This was becoming dreadful. The waist was elasticized and there was a row of tiny buttons around the top.
Cathy knelt down in front of me and started tying up a belt of orange ribbon, which lay under the white lace fringe at the bottom of the leg. This brought the material, which was otherwise quite baggy close into my leg.
"There that looks really sweet and everyone can see what nice legs you've got. Actually you'll be showing a lot more leg than the girls in their dresses will," she chortled.
My morale hit rock bottom at this point, and I offered no resistance when she brought out the white shirt. However, it wasn't really a shirt. She pulled it over my head, put my arms through the large puffed up sleeves, and then started doing up a row of small buttons up the back. It saw that it was really a blouse. It had a row of frills around the neck at the front and down the middle, and lace around the end of the sleeves, just like on my legs.
"There that looks really nice, and again it will tie in with what the girls are wearing under the top of their dresses, Janette will be so pleased you can make up the foursome, even though you didn't want to wear a dress," Cathy said.
I then began to realize why there had been the laughter after I refused to wear a dress; this was their way of getting revenge. I was annoyed at my stupidity, I even began to think it might have been better going along with the girls dress idea rather than put on this ridiculous outfit, but it was too late for that now. When I was dressed as Dorothy the audience didn't laugh, people actually came up afterwards and congratulated me.
"Right, nearly finished," said Cathy, "just your waistcoat to put on."
She held out another piece of the apricot orange satin, now fashioned into a sort of waistcoat, but who ever heard of an orange waistcoat?
"It's made from the top of Sharon's dress," Cathy explained, "all we've done is cut it off at the waist and add a row of small buttons down the front and then the buttons on your pantaloons will tie the two parts together. So, from the waist up you'll look just like the flower girls, and it goes nicely with your satin pantaloons," she said triumphantly.
I slumped forward and sat on the bed looking very unhappy.
Cathy said, "Good, now I will tidy up your hair a bit."
She took out one of her large combs and a brush and proceeded to backcomb my hair, it is very fine and thick, and I have been growing it long.
"There, how's that?" she asked putting me in front of the mirror.
My hair was now piled high and as it tends to be naturally curly, it looked as if it had been styled in a very feminine way.
"Hold it, while I give it a spray to hold it in place and give it some shine."
So saying she proceeded to liberally spray it with some sweet smelling perfumed spray.
By now, I was very unhappy and thought I couldn't feel any worse.
Then Cathy said, "Just one more thing, your shoes."
With that, she went over to her wardrobe and brought out a shoebox and lifted out a pair of shoes, girls shoes, covered with shiny orange satin, which buckled over the foot and around the ankle, there was even a small satin bow on the foot.
"Come on, let's get you finished." She said
So then, she proceeded to put on these ghastly shoes.
"You'll need to be careful how you walk in them, they have a nearly 2 inch heel which you'll have to get used to. Just take small steps and you'll be all right. It's lucky Sharon's shoes size was the same as yours," said Cathy bubbling with laughter.
I stepped over in front of the full-length mirror and looked at myself. Girls white glossy tights, with my panties underneath, a girl’s frilly, lacy blouse, the top of an apricot orange girl’s satin dress, and the satin pantaloons with their puffed up legs and the lace frills, and the awful prissy girls shoes with the silly bows. With all that and my hair done up in curls, I realized it was worse than being dressed as a girl; I was dressed as a sissy! With my legs in the shiny tights, making me look absolutely ridiculous.
"I can't go out like this," I whimpered, "please let me change, other ring bearers wear proper boys clothes, these are just awful, and they are girls clothes."
"All you said was 'no dresses' and you are not wearing a dress. But you will match in with the flower girls and that's what Janette will like and you do want to make her happy, don't you?" Cathy questioned.
"Yes, but I think you have played a trick on me, and it's not fair."
"It may not seem fair to you but that's the way it is. Now go downstairs and wait while I get dressed and be careful not to mess up your costume."
It was then I remembered that around the house there were other people getting ready including five cousins, Rosemary, Aubrey and Belinda who were the flowers girls and also Robert and Jason who had arrived last night.
Cathy shouted down the stairs, "Rosie, girls, here's Timmy coming down to join you; he is already in his ring bearers costume come and have a look."
With that, Cathy pushed me out of the room and I stood at the top of the stairs in my ridiculous costume. Rosie and the other girls came out of the lounge to have a look. They stood there as I held on to the stair head rail and first they all gasped, then put there their hands to their mouths , then squealed and then they all went into fits of laughter.
"Come on down Timmy and let's have a closer look, you look absolutely darling," said Rosie.
"OOOH what great legs you've got, golly they are the same kind of tights as I'm wearing," said Aubrey.
"But look, look," said an excited Belinda, "he's wearing our satin dress top and the blouse and aren't those pantaloons just so dainty, I love the lace around the legs," she squealed.
I came slowly down the stairs, being careful in the strange footwear, so I took slow dainty steps, normally I whizzed down two stairs at a time.
"I don't believe it, he is wearing the same fancy satin shoes as well, and doesn’t he look just darling?" said Rosie repeating herself.
They gathered round me having a closer look at my stupid outfit. "I like they way you've done your hair," said Belinda.
I went through into the lounge and sat on the sofa.
"How did they get you to dress up like this Timmy? Do you like wearing girly things?" asked Rosie.
"Wait a minute, didn't Cathy tell me you had played Dorothy in the Wizard of Oz at your school and your mum made you dress up like her and practice?" queried Belinda.
"I did it because Janette wanted me to. They asked me first to dress up like a girl in Sharon's dress. I refused, so Janette said I could be a ring bearer instead," I explained.
"But all the ring bearers I've seen have been nearly half your age and were wearing little boys black tuxedos or just a dark suit, not girls clothes and orange satin pants with frills," squeaked Aubrey before collapsing with laughter.
"I know that now, but they never told me what the costume was going to be, I only saw it for the first time this morning as I was putting the things on. By then it was too late, I've promised Janette I would do it and I can't go back on that. It's my mom and Cathy who dreamed up this idea. These shoes are already hurting me," I explained.
"Well Tim" said Aubrey, who was my age, "I think you are being very good and very brave to dress like this for your sisters wedding in front of hundreds of people. We will all be wearing our costumes for the ceremony and for the photographs afterwards and then we go onto Garthwaite Hall for the meal and speeches and then there is the dance, so you better get used to your pretty shoes you are going to be wearing them and your lovely costume for the next 12 hours," said Rosie.
I had not thought of all that. I was just thinking that I handed over the ring and then could change and get back into my normal clothes. However, the church was 20 miles away and the Hall was another 15 miles beyond that.
Mom then came downstairs in her full wedding outfit and hat. "Right girls, are you all ready, oh sorry Timmy, I only saw your top half, you look just like the girls, your hair is lovely, did Cathy do that? Stand up and let me see you and the girls as well."
She looked us over, as we stood in line.
"You all look lovely, really beautiful, the orange satin really suits you all, and Timmy, I'm so pleased the way your pantaloons have turned out. I was thinking off making them longer and with two or three rows of lace, but I think they are nicer with the shorter length, it shows off your legs much better. Perhaps I should have made the dresses shorter, but no, three inches below the knee looks right," mused Mom.
I stood there with the girls, with my silly short frilly satin pantaloons and thought, can this get any worse? Later that day I was to find it could, much worse.
Then Janette came down. She came in through the far door and as we were all standing behind the sofa she could only see the top half of the other girls and me.
"But what has happened? I've got four flower girls, wait a minute, and is that you Tim?" she said coming behind the sofa.
She looked down at my pantaloons and tights and gasped.
"I thought you were getting a suit for him," she said as she turned to Mom.
Mom jumped in. "Well I thought as we had Sharon's costume made, it was a pity to waste it, so I fashioned the pants out of the skirt and kept the top half with just a slight alteration. Doesn't he look gorgeous?"
"Well he does look sweet, but I think I would have preferred to see him in a suit, wouldn't you have preferred that Tim?"
Mom was standing behind Janette and by signals, she indicated I had better agree to prefer the costume -- the girls did not see this.
I didn't know what to do, I didn't want to spoil Janette's wedding by making her think I was unhappy, by now also, Cathy had come downstairs and she had heard what Janette had asked and was looking threateningly at me.
So I said, "No Janette, I don't mind the costume, it means you have a ring bearer and you also have a stand in fourth flower girl."
Mom and Cathy beamed, the three girls looked at me in amazement and Janette came over and gave me a big kiss on the cheek, and I blushed down to of the bottom my socks. No, it would be the soles of my tights.
"That is so sweet of you Tim. Yes, you can be my extra special flower girl."
All the girls were sniggering now, and Mom and Cathy looked very pleased with themselves. So there it was I was off to the wedding looking like the biggest sissy ever. All my relatives, friends from the town, guys and girls from my school would see me, photographs taken, boy was I doomed!
The cars came an hour later, during which time I endured the questions and taunts of the girls. Do you like the feel of the tights? Is it true what Cathy told us that you are wearing lacy panties? Do you do your hair yourself? What's the perfume smell? Oh, it's only hair spray. Do you want to borrow my perfume? It’s in my handbag. You will need a handbag; your pantaloons have no pockets. They went upstairs and got a white satin handbag from Cathy.
Are you wearing any makeup? You can borrow mine. Just a little mascara and a touch of blusher, oh, you are already blushing a lot as it is.
Cathy came down at this point with things for my handbag, and proceeded to make up my eyes with mascara and put some blusher on my cheeks and just a touch, she said, of pink lipstick on my lips, and then she put the things in my handbag, "So you can freshen up later."
Then, to add to my torment in from the garden came Robert and Jason, They were in trousers and shirts, ready for the wedding, maybe just with a jacket still to put on. They looked at the four of us in our orange costumes.
Robert said, "Wow, you sure have prettied up nice, but I though there were only three flower girls."
Jason had walked round the side of the sofa and now saw my pantaloons and my legs encased in the tights.
"Bob, I think one of the girls is a boy, well just maybe. Have a look," said Jason.
Robert came round to see. I cringed, as he looked me up and down. "Oh my god is that who I think it is. What an outfit, what a sissy, you're not going to the wedding dressed like that are you Tim?"
Cathy interrupted before I could answer. "Tell the boys what you just told Janette, Timmy about how you want to be a ring bearer and a stand in flower girl."
"Yes that's true," said Rosie, "he is going to be our fourth flower girl, don't you think he has lovely legs, come out and show the boys your tights Timmy."
I walked out into the middle of the room, as I passed Jason I noticed he sniffed and smelled my perfume and grimaced. So I stood there in my satin, lace and frills while everyone commented.
"Do you really like dressing up all girly?" asked Jason who seemed interested in my appearance.
Again, before I could answer, in jumped Cathy, "Well just look at Timmy in the photo above the fireplace. That's him dressed as Dorothy, the little girl in the Wizard of Oz, you were really good in that role weren't you Timmy?"
"Oh, how sweet," said Robert, "well I'm sure you are going to be the centre of attention today in your pretty clothes. Come on Jason let's leave the girls to gossip, we'll go back out into the garden."
I endured all this without complaint, somehow I realized that reacting to their taunts would make it worse so I just went along with it and after a while they started just to gossip amongst themselves.
The flower girls and I had to travel in the same car to the church.
The chauffeur holding the door said, "Come on girls, - hop in," he then did a double take when he saw me in my sissy outfit. "Why aren't you in a dress like the other girls?" he asked, causing them all to fall about with laughter.
"I'm a boy and my name is Timothy. I'm the ring bearer," I squeaked in embarrassment.
"Well, you could have fooled me sweetie it takes all sorts..."
It felt weird sitting with the three girls, they were all encased in their dresses, which had large white petticoats underneath, while I sat squashed between them with my satin pantaloons and long white tights showing.
We arrived at the church and had to stand in a group as the wedding party assembled. The four bridesmaids were already there and rushed over to greet us. Their dresses were orange as well and they complimented us on our dresses. I had been sort of hidden behind Aubrey and it was only when I stepped out that Angie the chief bridesmaid gasped.
"I thought you were all flower girls, who are you?” she asked
"I'm Timothy, I'm the ring bearer," I stuttered.
"But what a lovely costume, although it's a trifle unusual, who made it for you?" said Angie.
"His mom made it," said Rosie, before I could answer. "He wanted to be the fourth flower girl so his mum took Sharon’s dress and made it so he could be a flower girl and a ring bearer."
"Well that's lovely of you, what a wonderful boy," said Angie, "you can walk with me down the aisle with the bride and groom carrying the ring and when they come back down the aisle you can be the chief flower girl and carry my bouquet."
Therefore, it was when Janette arrived we formed a procession and followed her down the aisle. There were stares, figures pointing and hushed conversations as I walked gingerly down the aisle in my uncomfortable sissy shoes.
Then I had to stand with the other girls as the ceremony took place. I was aware that as I stood behind a low barrier with the girls only the top half of my dress showed and which was identical to the other three girls. You could see people smiling at us and taking pictures.
After what seemed an age the music struck up and Angie grabbed my hand and we walked in procession back down the aisle, she told me to wave to people I knew, but I was too scared and embarrassed. I concentrated on taking small mincing steps to keep pace with the procession and conscious all the time off those orange satin shoes at the end of my exposed legs.
The photographs took forever. We were posed sitting, standing, holding flowers, in small groups, in family groups. Every time I posed at the front being told to smile. One time, when I was with Janette and Mike, they actually took photos of me sitting on Mike’s knee.
Mom wanted lots of photos with her and with Cathy and insisted on the photographer taking many pictures of me alone, at one point Cathy came up and using my handbag, touched up my makeup so he could take some close up portraits. What I didn't realize until later is that she had put on much heavier blush and lipstick and emphasized my eyes with mascara and eye shadow, so I looked really girly.
"Gosh, Timmy, my mom won't let me use that much makeup, you are lucky to have a sister like Cathy," said Belinda.
"I think we should call you Tammy now, you are more girly than we are anyway," said Rosie. So from then on it was 'Tammy' whenever I was called. Cathy soon picked up on this and from her it spread around the wedding party until I think some people thought it was my real name.
After the torture of the photos, it was off to Garthwaite Hall. As I got in the car, the chauffeur looked at my painted up face and shook his head muttering "Little Pouf.”
"Come on in Tammy, let's get to the food and drinks," said Rosie as we bundled into the car. The driver looked bewildered.
When we got to the Hall, we found that the tables all had place names on them. I thought initially I would be with the other flower girls. However, Janette had placed me with Robert, Jason and the other young boys, something I didn't want to do while wearing the very girly outfit. I went up to Janette and told her.
"Gosh Tim you have gone a bit overboard with the makeup, so I can understand why you don't want to sit with the boys anymore. Now let's see, the girls table is already too full."
I looked across at the table where Rosie and the others were sitting it was designed for ten but there were twelve girls already sitting there.
"Tell you what Timmy, why don't you go to table seven over there, you can help look after the little ones as well."
I looked across to table seven. On it were a dozen, at least, of young kids, some were in high chairs, aged between three and around seven all in party dresses or little suits being looked after by a young girl of around eighteen.
Janette took me over. "Tammy this is Timmy, there isn't a seat at his table and he would like to help you look after the youngsters, he has been my ring bearer and a very special flower girl."
"I can see he is special all right," said Tammy, "yes I could do with some help, why don't you sit over there Timmy and help me pass round the food."
I sat down, just then Rosie came by and called out to me.
"I see you've found the right table Tammy."
Tammy turned to me and said, "Did she just call you Tammy?" I nodded.
"Well, boys and girls, from now on I'm Tammy One and this pretty girl over here is Tammy Two," she said.
That started it; "Are you really a girl?" said one.
"Of course she is silly, can't you see she is wearing girl’s clothes, tights and look at her dainty shoes and she is wearing makeup."
"Yes," said Tammy One, "you do seem to like a lot of makeup."
I gave up fighting it at this point and just said, "Yes well it's a special day and I wanted to look nice, the bride is my sister."
"Well you look very pretty," said another little girl, "but why didn't you wear a dress like the other flower girls?"
"Because I was also the ring bearer and that is usually done by a boy," I weakly replied.
"So that means you were a girl pretending to be a boy," the youngster came back.
Tammy One was watching this interchange with an amused smile.
"Well, yes, I guess I was pretending," I said.
"I think you make a better girl than a boy," said Tammy one with an even bigger smile.
And so, it went on. Actually after a while, I really enjoyed it, as the kids were funny and weren't unkind to me like some of the others, so I joined in the fun and ate and drank and played with them.
Then a problem arose. I needed to go to the loo. Where did I go and how did I get these pants off? I shuffled around for a while until I couldn't stand it any longer. I walked over to Cathy's table and whispered in her ear.
She said loudly, "Oh Tammy needs to go the little girl’s room, excuse us everyone."
So she grabbed me by the hand like a toddler and walked me out of the room, I was so embarrassed I did not see her gesture to Rosie and the girls to follow us.
"Well Tammy, there is not room to do this inside the cubicle so we will need to take your pretty pants down in here."
Here being the large room where several women and girls were already washing their hands and redoing their makeup in front of a large mirror. Therefore, she made me stand in the middle of the room while she undid the bows around the legs on my pantaloons.
"We are going to have to take your pretty shoes off as well so we can get the pants off completely," said Cathy.
Just then in walked Rosie, Belinda and Aubrey who watched while Cathy took off my shoes and pulled down my pantaloons and I stepped out of them. By now, there was an audience of about 16 women and girls watching me, I don't think anything could be more embarrassing.
I stood in the room wearing just my tights, the blouse, and the dress top.
"Tammy is wearing panties, look," said Rosie pointing at the yellow outline under my tights.
"Yes, pretty lacy yellow panties," Cathy said. "Mind you pull up your panties and tights properly when you have finished Tammy and remember to sit down," she added.
I went into the cubicle. It took me ages to perform; I was so uptight and humiliated. Eventually I had finished and I readjusted my panties and tights and walked out. If anything, there were more people in the room now; including the other girls, but Cathy had gone. Rosie said she had told the girls to redress me.
So then, I had Rosie, Aubrey, and Belinda fussing over my pantaloons and retying the ribbons, and then putting my shoes back on, watched again by a throng of other people all laughing and making jokes.
Then Rosie said, "Cathy said you also have to freshen up your makeup before you go back, here is your handbag."
"But I've never done my own makeup," I whined.
"Well now is the time to learn," said Belinda.
I took out the blush and lipstick and tried to redo my makeup. What I didn't realise is that Cathy had substituted much brighter makeup, a bright red lipstick and a really strong rose blush – so even though I only touched up a bit -- the effect was dramatic.
"Wow, girl, you really know how to pile on the war paint, you will be pulling in the boys from all over the county," laughed Aubrey.
So then back I went into the dining room but not before Rosie had sprayed me heavily with perfume.
I caused a minor sensation as I walked back in the room, the story of my undressing in the ladies loo had done the rounds plus my reinforced makeup and the powerful wafts of perfume which followed me around caused smiles from the ladies, but I noticed many of the men were shaking their heads.
"Why don't you come back to our table now Tammy?" said Rosie. "A couple of the girls had to leave early so there is plenty of room now and we could have lots of girly talk."
I looked across at the kids table, but Tammy One was sitting there with just two kids, as parents had retrieved most of the other kids.
I sat down with the girls. First, they wanted to borrow my makeup, asked me what perfume I used, what kind of boys I liked and talked about their favourite boy band pop stars and asking me my opinion. I tried to join in but it was hard to keep up my spirits with all the constant reminders that I was trapped in this costume.
After the speeches -- "and 'thank you' to our four beautiful flower girls," was one line, the dancing started. In a while, some of the boys came over and asked the three girls if they wanted to dance. Rosie spoke up and said yes but one of you has to ask Tammy for a dance as well.
"Oh come on," said Robert, "I know he looks like a girl but that doesn't mean we have to dance with him."
"Tammy has taken a lot of trouble to look like a pretty girl and someone has to ask her to dance," said Belinda.
"OK then," Jason stepped forward put out his hand, pulled me up, and walked me onto the floor before I knew what was happening. Jason is thirteen and very well built and about three inches taller than I am. The other guys picked up Belinda, Aubrey and Rosie and we were soon all on the floor. I attracted some quizzical looks but let it go by me. In a way, I was enjoying it. Jason was a good dancer and I followed his lead. We stayed on the floor for about 15 minutes.
As we walked back, he asked if I wanted a drink, I said I'd like a diet Coke. He brought one from the bar and instead of walking me back to the table suggested; we go out on the patio for some fresh air. I hesitated but then said OK, I was a trifle hot. Then he did a strange thing. He took my hand and led me outside, I don't know why but that gave me a tingle, a weird feeling. While we danced we hadn't really been touching, it wasn't that kind of music. However, as he held my hand I suddenly felt a strange feeling welling up inside me. I wondered if Jason felt it as well.
I looked across at him. He had a broad handsome face, a strong jaw line, intense blue eyes and a shock of brown hair. He was looking at me strangely.
"Timmy, Tammy, what should I call you?" he asked.
"Tonight everyone seems to be calling me Tammy, so stay with that -- if you like," I replied.
"Yes I like the name Tammy, it suits you. Are you enjoying today dressed like that?"
"To be honest no, the reason I'm wearing this stupid outfit is that I refused to wear a dress and stand in for Sharon. So they tricked me into wearing this outfit pretending it was a ring bearer’s costume," I explained.
"I think you would look better in a dress," said Jason.
"Given everything that's happened so do I," I joked.
"Tell you what," said Jason. "Just wait here a moment."
He went back inside and came back with Aubrey, his sister.
"Look Tammy, Aubrey has her clothes in the boot of my dad’s car. We are leaving later tonight. She can loan you one of her proper dresses and you can get out of that silly outfit."
"Would you do that Aubrey, anything would be better than these silly pants and stuff?" I said.
"Yes of course I can Tammy, just give me a minute to get the car keys from my dad," she said and hurried away.
Therefore, a few minutes later Jason, Aubrey, and I were out at the car.
“I have these two other dresses, one is a summer frock, but it's really a daytime thing and mummy also made me bring this party dress," she said, pointing to a white dress with pink trimmings on a hanger. "It was in case I wanted to change, but I'm OK staying in the flower girl dress, you can have it if you want, it's actually getting a bit small for me. I got it for my eleventh birthday party. Do you want to try it?"
"Anything is better than what I'm wearing now," I replied, "what about shoes? I want to get rid of these terrible shoes," I groaned.
"Don't forget I'm wearing them too, but yes they are silly. You look about my size, and I brought a pair of white shoes, which should fit you. You are going to look really neat," said Aubrey. We picked up the new kit and walked back to the main lounge. "I need somewhere to change, I'm not changing in the ladies room again," I said.
"Doesn't the bride have a room to change in, before she goes?" suggested Aubrey.
"Right, good idea." So Jason came with me, while Aubrey waited outside with the clothes, I went up to Janette and whispered in her ear about borrowing her room for a moment to change my clothes.
"No problem Timmy, you must be really glad to get out of that outfit, mom went a bit far with the lace and frills," she said.
I took the key from her, and as I left I heard her whisper to Mike, "He wants to get out of those clothes -- poor kid,"
"Yes, they really were just too girly -- he must have been very embarrassed," he replied.
Aubrey and I went up to the room and she helped me out of the flower girl clothes and then picked up the party dress. She placed it over my shoulders and it slid down. At this point, I looked in the mirror.
"I can't wear this, it's so short, and it's got no arms," I cried.
Indeed, it did not have sleeves, it had shoulder straps, otherwise my shoulders, and arms were bare. It ended just about 3 inches below the top of my legs and it had a sort of built up bosom section which made it look like I had boobs, small boobs, but nevertheless boobs. Again it was seeing my legs encased in white shiny tights that made me feel very odd, the dress was so short, much shorter than Aubrey's flower girl dress.
"I said you would look really neat and you do, you certainly look a much more convincing girl than you did in that other silly outfit," said Aubrey, who seemed a bit upset I didn't like her dress.
"Yes, I guess you are right, it is just a bit of a shock seeing myself like this," I replied.
Just then, there was a knock on the door. It was Janette, coming up to see how I was doing. She did a double take when she saw me.
“Gosh Tim, I thought when you said you wanted to change, it was into some boy clothes, not into a party dress. You do look lovely though."
"It's just that Aubrey offered me some clothes. If I had some boy clothes I would have changed into them."
However, as I was saying that, I realized I had never thought of changing back into boy mode -- if I had, I could have asked Jason for some of his, which were presumably also in the car. Wow, this was getting weird
"Well, if that's the way you want to dress, you need some more accessories, luckily I have things here in my cases, just a moment," said Janette.
"Here are some bracelets, a ring and you'll need a necklace with that dress and I have just one pair of clip on earrings, you can keep the earrings if you like them Timmy," said Janette.
Aubrey was helping me put on the jewellery, then Janette touched up my make up and re-combed my hair, putting in also a small flowered hairpiece.
When I looked at myself, I was astonished. I looked like a 16-year-old girl, a bit on the short side maybe, but definitely a teenage girl.
"You look great girl, why don't you go out and see your boyfriend?" said Aubrey, Janette looked astonished at this.
"No, no, he is not a boyfriend, it's just he is the one person who has showed a bit of concern about the way I have been treated today, and yes, I like him for that. But I don't like him because he is a boy, he is just a lot nicer than the others I've met today, but not including you Aubrey, you've been kind as well, thank you," I cried.
"Well, if it helps Tim. I think you are a nice natured and good-looking boy, and I've always thought that. Doing what you did today was a wonderful thing; I can't think of any other boys I know having the guts to do that."
With that, she came over and gave me a kiss, right on the lips. This time I really felt a tingle and the feeling of our lipstick-covered lips touching was just wonderful. This was turning out to be a confusing day!
"Time to go children," said Janette. We picked up our handbags and left the room. Jason who had been standing outside nearly fell through the floor when he saw me. He was so surprised at my appearance he literally couldn't speak, just turning to look at me and gasping. He tried to get hold of my hand again, but with Janette and Aubrey watching I felt shy, and I needed to concentrate walking in yet another pair of heels.
Jason's reaction was multiplied a hundred times over when I walked into the main room and over to the table and Rosie, Belinda and the other girls. They gathered around me and asked a load of questions.
I told them that wanted to get out of the silly costume my mom had made and Aubrey offered me a dress of hers.
"It is comfy, it fits, and at least I look like a human being, yes, like a girl, but at least not like some pansyfied sissy. I just wanted to show mom and Cathy, that from now on I was in charge of how I dressed as a boy or even as a girl and I were not going to take part in any of their games."
Unknown to me both mom and Cathy had come over to the table as I was making the speech and heard what I had to say. Mom came up to me and grabbed me.
"I'm sorry Tim,” she said, “it was the wrong thing to do, I was upset when you wouldn't take Sharon's place, but it was wrong to ask you in the first place, the outfit was a bad idea, I've had quite few people tell me that here tonight, so I apologize."
Cathy came over at this point. "Tim, a lot of the dress up was my Idea; I think you are a very brave and talented kid to do what you did and what you've just done now. I’m sorry. Just don't please come near any of my boyfriends dressed like that."
That broke the ice a bit and the tension dissolved. We went back to chatting.
Everyone was much nicer to me now, although I did get some weird looks from some of the other guests, but the young crowd was cool about it. The boys came over and joined us at our table, we chatted, and some of the group occasionally got up to dance.
Jason came over to me and asked me again for a dance. I was a bit shocked; no one had suggested he should do it this time.
I said, "Don't let this dress fool you Jason; I am a boy under all this clobber. Are you sure you want to dance again?"
"You are as pretty as any of the girls and you are nice to dance with, so why not? Some of the girls are already dancing together," he replied.
This was true, most of the boys were sitting around talking, but the girls were all up dancing, so as I was the only "girl" not up and dancing it seemed unreasonable to refuse.
"Yes, I'd like to dance with you Jason, let's go," I said and we went up to the dance floor.
Janette and Cathy were both up dancing and as she passed Janette asked, "Are you enjoying yourself, Timmy?"
"Yes," I replied, "this is a lot better than that other silly outfit, although I would prefer trousers."
"Well you look really nice, and thank you again for being my flower girl and ring bearer." said Janette with a smile.
Cathy also came by with her partner. "This is my little brother John, doesn't he look cute in his party dress, and you've found a boyfriend I see," she needled me, yet again.
"It's your fault I'm dressed like this Cathy, if you and mom had let me wear a proper ring bearer suit I wouldn't have ended up like this. Jason is just my cousin, he is not a boyfriend."
"Wow, your sisters are very different, aren't they," said Jason as they moved away, "is Cathy always so mean to you?"
I explained to Jason how we were always arguing and she was always running me down. We went on to talk for quite a while, again sitting outside away from the noise. He is an interesting guy and like me is a keen swimmer and seemed to like the same kind of music I do.
While we were chatting, Aubrey walked up and spoke.
"Hey Jason, stop monopolising Tim, I'd like it if he had a dance with me. You don't mind me asking, do you Tim?"
I blushed and said, "We were just chatting and yes I'd really like to dance with you."
So then, we spent the next few dances together.
"Have you ever danced with a boy before,” she asked.
"No, and I've never danced in a dress before, and I never will again," I said with emphasis.
"Tim, I meant what I said before about liking you and admiring you for what you've done, I'll understand if you want to go back and chat with Jason, but I would like it if we could talk for a while," she said looking straight into my eyes.
I have never had a girl speak and look at me that way before and again I felt that tingle.
"Look Aubrey I think you are the nicest, prettiest girl in the room. I'm just bowled over that you'll even talk to me, especially when I'm in a dress. Jason and I were just chatting about things, like swimming and music, there is nothing more to it, if that's what you were thinking." I looked straight back at her, now holding her hands.
"I know you are champion swimmer at school. That you even tried for the county juniors. That you do voluntary work for an old persons home and you are in the top two or three in all your subjects at school. That you like music and drama and play the piano and the guitar and you've won prizes for your singing," she said.
"Where did you get all that from?" I said astonished.
"I told you I liked you and I've been talking with Janette, she told me a lot about you, and I saw how you helped Tammy look after and entertain the small children today," she replied.
"Well now I need to know about you then," I countered.
So we talked animatedly for the next hour. Aubrey was fun to talk to and time just flew by until my mom came up and said it was time to get ready to go, the car to take us back home was waiting.
"How can we meet again, do you go into Bramfield?" I asked Aubrey.
Bramfield was the nearest large town, I knew Aubrey lived 25 miles away on the other side of the town.
"We will have to meet again, if only for you to return my dress and shoes!" she said. "Yes I visit Bramfield to shop; we can meet there if you like."
"Yes that would be great, I have a swimming competition at the Bramfield leisure centre a week on Saturday, I could meet you after that, we could go for a snack and maybe go on to the pictures," I replied.
"Can I come to watch you swim first? I'd like to see you, I could cheer you on," Aubrey asked.
"Wow, my own supporters club, I'd like that. I'll call you and we'll fix up when to meet,"
I moved closer to her to say goodbye, at the same moment she moved towards me and it seemed natural that we came together and kissed
"Well isn't that a pretty sight, two beautiful girls having a long lingering kiss. Time to go home Tammy, are you saying goodnight to Jason as well." This was Cathy, jumping straight in, in her characteristic manner.
I did not deign to reply, other than to glare at her.
"She IS awful to you, we will have to find a way to get back to her," said Aubrey.
"Really it's not worth the trouble, I just wait for the time she goes off to college, and I don't have to mess with her anymore. Anyway, I must go, see you in Bramfield next week," I replied.
"I'll look forward to that, but who shall I meet Timmy or Tammy?" she joked.
"That's for me to know and you to find out,” I replied. "Perhaps I should go and say goodbye to Jason, he has at least been kind to me, as well."
"You really are such a thoughtful and good natured boy aren't you, what a contrast to your sister. Just be careful with Jason, he may want to kiss you as well," she said.
"The sooner I get this dress off the better, then," I joked, but there was something in the way Aubrey looked at me as she talked about Jason that made wonder if she was trying to tell me something.
As I went over to Jason, he jumped up.
"I wondered if we would get a chance to say goodbye. Thank you for the dances, I've enjoyed talking with you. What would you think if we met up in town and went to the arena next time they have a good concert?"
"Great idea, yes let's get in touch and thanks for giving me time when I've been dressed like a weirdo," I replied.
I really did not want to get in too deep but not wanting to be rude to a guy who had been kind to me. We slapped hands and I turned to leave, but I could see in the mirrored wall in front of me he watched my every move as my dress swished round and I minced out on the of room in Aubrey's heeled shoes.
As I sat in the car on my way home, I thought back on my day, spending nearly 12 hours in girl's clothes. It had been a long day, and my feet really hurt but I had made two new friends both of whom seemed to like me and wanted to meet me again, but I did need to find out from Aubrey what she meant in that remark about Jason.
To be continued
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