Crossdressing with My Boyfriend and Girlfriend
(The Misadventures of Timothy)

By CindyBelle
 ©May, 2007

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.
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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)

PART 1

"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

Crossdressing with my Girlfriend and Boyfriend
(Pt. 2 A Date with Disaster)

By CindyBelle
 ©June 2007

Crossdressing with my Girlfriend and Boyfriend
(Pt 2 : A Date with Disaster)

Tim finds taking a dress into a mens changing room is a bad idea and then learns with dismay about his next starring role in his schools musical production, his mom is thrilled though.

The next morning when I got up, very late, the first things I noticed were the clothes I’d worn last night scattered on the floor; Aubrey’s white party dress and her shoes, and the tights and panties that Cathy had provided. Looking further I noticed someone, probably mom or Cathy, had also returned the orange satin pants and top from yesterday plus the blouse and those ludicrous orange shoes.

I put on a pair of boxers and staggered along to the bathroom and there I noticed I was still wearing the makeup from yesterday —that really gave me a shock. I spent an extra long time in the shower and then inspected myself closely for any remaining traces.

“Well did you enjoy your girly day Timmy?” was the greeting I got from Cathy at breakfast. I ignored her.

“ I looked into your room last night, but you had gone straight to sleep, in future you need to remember to remove your makeup before you turn in, said mom. “You also should hang up your dresses and not leave them scattered all over your room”

“Don’t worry, I won’t be wearing makeup again and I don’t want to have that flower girl stuff in my room” I retorted.

“Oh does that mean you are keeping Aubrey’s pretty white party dress?” said Cathy.

“No, I’m seeing her a week on Saturday in Bramfield, I’ll give it back to her then. She is coming to watch the swimming competition,” I explained.

“Oh, that’s nice dear — you seemed to get on with her very well, and Jason too I noticed” replied mom. “You had better hang up the dress neatly in your wardrobe until then. I’d better check if it needs cleaning as well.”

“Talking about dresses,” mom went on, “I need to tell you about my plans. Now that Cathy is off to college in a couple of weeks, I’ve decided to go full time into dressmaking, I’m tired of travelling into Bramfield to that office every day, and I’ve found I’m getting more dressmaking orders than I can handle in my spare time. So I’ll be working from home from now on.”

“Wow, that’s good mom, it made a long day for you with all the travelling and you really are good at dressmaking” I replied. Mom had had a hard time since Dad left us seven years ago — he had set up with a secretary he met at his office and had then been posted to America so we never saw him now. I was only four when this happened so don’t remember too much. But he did give mom the house plus a generous allowance to pay for my sisters and I through school and college, he sends money at birthdays and Christmas, or maybe his secretary does, and that’s the limit of his contact now.

“Well I’m going to need your help more now, Tim. Now that both your sisters are going to be away” mom said. Cathy was starting college in a few weeks and Janette and Mike were setting up house 100 miles away in Bristol, so soon it would be just me and mom.

“Don’t worry mom, I’ll help as much as I can — it’ll be nice to have you at home when I get in from school, Cathy’s meals weren’t as good as yours” I responded. Cathy used to make a meal when we both got in from school, as mom sometimes did not get home until late. Although actually I often found I was doing most of the work recently, Cathy really did not like cooking, while I rather enjoyed it.

“Well maybe you can be the little housewife now then, you seem to like girly things,” said Cathy . “You can also have the clothes I’m leaving in my small wardrobe if you like, most of them are too small for me now. There are some more jeans in there that will fit you”

This was a reference to the fact that mom had, in the past, sometimes passed on some of Cathy’s more unisex clothes to me when I was younger and growing fast : jeans, tops and socks but not dresses and such.

“Thanks Cathy,” I replied “I’m really going to miss all your kind and helpful remarks”

“OK children, that’s enough” said mom “ You do pick on Tim a lot, Cathy, he is a good boy and certainly does better at school than you ever did and he keeps his things tidier than you ever have, so leave him alone” That’s a change I thought, maybe things will be better for me with Cathy gone.

Back in my room I put the dress and shoes in my wardrobe and stuffed the other flower girl clothes in my bottom drawer. I forgot about the dress until Aubrey called in the middle of the following week. We first fixed up details of where we would meet.

Then she said, “How are you going to bring the dress, it needs to hang, you can’t fold it.”

“Oh, I hadn’t realised that. But won’t it also be a problem while you are watching the swimming and afterwards if we go to the pictures” I asked.

“Ask your mom if she has a garment carrier, then at least you can carry it over your arm. But where can we keep it until I catch the train home?”

“Tell you what I could it put in my locker at the pool and we could come back after the pictures and pick it up then.” I replied.

“Great idea, thanks Tim. Oh by the way I’ve got some great pictures my folks took of us dancing, I’ll bring them with me. There are some of you with Jason as well.” She said.

“Aubrey, I really don’t want to see any more pictures of me at the wedding, I’m glad Janette had a good wedding, but for me it is something I really want to forget.” I said.

“What, even meeting me and the kiss we had?” she joked.

“All right, I enjoyed some parts of the day and yes I really do want to meet you again. See you Saturday then” I replied.

The next day, I got a call from Jason. “Hi Tim, how’s things?”

“Fine thanks, I think I’ve recovered from the ordeal last week, although I’d still like to buy up all the pictures,” I joked.

“No way, man, I keeping the ones I’ve got of us, I’ve showed them to friends and they all ask ‘who is the good looking doll you’re dancing with?’- so you now have a fan club.” he said. “ Hey did you know Speed Wagon are doing a gig at the Bramfield Arena on Sunday, I know a guy who does the sound there and can get tickets, want to come?”

“Wow, I’d like to, but I’m coming up to Bramfield on Saturday already for a swim meet” I said, wondering if he knew about Aubrey coming wqith me, “ It will strain my budget coming up to town twice in a weekend” I replied, trying to make a way out.

“Oh pity about Saturday, I would have liked to have seen you at the pool, but I have a dance class in the afternoon — I’m taking tap and ballet lessons. But don’t worry about the cash on Sunday, it’s my treat. Say you’ll come” he said.

Well, it didn’t seem as if Aubrey had told him about her coming to the swimming meet, so I really didn’t have much of a way to turn him down without hurting his feelings. But I really would have to tell him that this was a one off, a sort of thank you for not ragging me at the wedding.

“Yes I’d like to come I said, as long as you are OK about paying. I don’t like to impose on you like that, when I can’t pay you back, I replied.

“Don’t worry about it, I’ll enjoy having you as company, you appreciate music, see you Sunday” he concluded.

At school on the Friday I had an unpleasant shock. Mrs Cartwright strikes again! In her drama class she announced that she was starting to cast for this terms musical production. There were groans from the assembled throng. “This year instead of a modern musical we are going to do a musical that is one over a hundred years old,” more groans, “It is ‘The Mikado’ Gilbert and Sullivan’s most popular and famous work. I’ll be going round each class from today and selecting the cast.”

At the end of the lesson she called me to the front. “Timothy, you did wonderfully well in ‘The Wizard’ and I think you are the best choice for the female lead in the Mikado, she is called Yum Yum, it’s a big part and needs a good voice and I believe you will be able to carry it off.”

“Mrs Cartwright, if you don’t mind, I’d rather not. I’m glad to have helped out last time but couldn’t you give someone else a chance” I urged.

“Timothy, its only going to be a year or so and your beautiful treble voice will break, this is probably the last chance you’ve got to do this kind of role and you are far and away the best singer for a soprano role in the school, plus you can act and play the role well.” she insisted.

“I suppose I don’t have any choice, then, but I’d really rather not”, I said.

“Don’t worry it needs a big cast and there will be boys playing the other girl roles , so you won’t be alone like in the Dorothy part.” she cajoled.

I went home with the news. Mom was delighted, I think she saw more dressmaking opportunities! “You’ll make a lovely Yum Yum. I’ll help make the costumes for the whole production, yes, I’ll speak to Mrs Cartwright on Monday”

I quickly changed the subject. “Mom I’m going to need a garment carrier to take Aubrey’s frock back tomorrow, I’m meeting her in Bramfield, can you help?”

“Don’t worry I’ve got just the thing, I’ll get it out in the morning”, she replied.

Next morning she gave me the carrier, it was a five foot long carrier with a zipper down the front. The only problem was it was made of transparent plastic. Yuk, everyone would be able to see I’m carrying a prissy looking dress when I get on the train.

I left at 11 o’clock carrying my sports bag, which also contained Aubrey’s shoes and with the dress. I felt very conspicuous with it over my arm and it was impossible to hide it. On the train there were stares and little smiles from people. One child in a not very quiet voice whispered “Mommy, why is that boy carrying a dress?” More smiles all round.

A lady next to me turned and said “It is a pretty dress, is it for a special occasion?”

“No, I’m taking it back to my girlfriend, I just borrowed it,” I said, before realising how that could be interpreted.

“Well, I’m sure you looked very nice in it” she said laughing. I just blushed and said nothing, I’d said too much already.

At the station, I had to wait 20 minutes for Aubrey’s train to arrive, more embarrassment, standing around, holding the dress.

She dashed up when she arrived, we had a quick hug, and she said “ You brought the dress like that” pointing at the transparent carrier “here let me take your sports bag, I’ll let you carry the dress as you like it so much!”

We walked around to the Leisure Centre, chatting and laughing all the way. I said goodbye to her at the entrance before walking towards the changing rooms. Have you ever tried walking into a men’s changing room at a sports hall carrying a party dress over your arm? Don’t.

“Going on somewhere afterwards Tim? Somewhere nice?” The comments came thick and fast, most of them from guys I had met at other competitions.

Then came, “Wait a minute, I was at your sisters wedding last week” it was John, the friend of Cathy’s, “Isn’t that the dress you wore then when you went dancing with the boys in the evening?”

Get out of that one I thought. But I learned it is best just to ignore the taunts and people soon get bored, so I turned and hung up my dress, no! The dress, and started changing into my speedos. Luckily that seemed to quieten things down a bit. The guys know I’m a pretty good swimmer so that may have helped.

The meet went very well . I was in two events, I came third in the first race and won the second. So I got a cup and a medal. I saw Aubrey cheering and applauding and felt good about that. After the presentations I went up to her and gave her a hug, we chatted for a while, then I said, “Let me get changed and we’ll go out and celebrate.”

I was late getting back in the changing room and just about all the guys had left. When I opened my locker, I had a shock, my clothes were gone and just my sports bag and the dress were left in the locker. Whoever had done it must have taken the key from my shower bag while I was racing and removed the clothes. I checked and they had put my wallet and loose money and the stuff from my pockets in the sports bag.

I looked around in all the open lockers, but there was nothing. Then I noticed a note on a shelf inside “Enjoy your evening, your other clothes will be in the post on Monday”

I sat down with my head in my hands. What could I do? There was only the dress and Aubrey’s shoes. I did have a spare swimming costume in my kit, plus some white socks. The only thing to do was to put on the dress, see if I could tease my hair up a bit and get help from Aubrey. My hair won’t stay straight, so I just let it curl and I think it looks better if it’s fairly long, otherwise it looks weird.

So, that’s what I did. In the end I didn’t look too bad. The hair on my legs, what there was of it, was like my head hair, very fair, so my legs looked all right. The shoes were as uncomfortable as ever, but I suppose by now I was getting used to them.

I went out to find Aubrey. She was waiting at the entrance, as were a bunch of the guys who set up a chorus of shouts and wolf whistles. I dashed up to Aubrey.

“So it is Tammy again is it? she said. Then she saw how anxious I was and got hold of me. “Hey, don’t worry, we’ll get out of this. Where are your clothes?”

“The guys say they are going to mail them. We are going to have to go a shop and buy something, anything, so I can get home” I cried.

“Not easy, Tim, its 6 o’clock on a Saturday night and that’s when the shops shut. Lets get away from here and go and have coffee and see what we can do” she said.

We went to a coffee bar, luckily it was quiet and we sat in a corner and discussed the situation.

“The best thing I can think of is for me to do your hair properly, put some makeup on you so you can pass as a girl, I’ll give you my handbag for your wallet and tickets and I’ll take your sports bag with me, you’ll look silly in a party frock carrying a sports bag”, said Aubrey.

“I’ll look silly anyway, wearing this stupid dress on train on a Saturday night” I wailed.

“You might get asked to a neat party, and pardon me its not a stupid dress, I rather like it and I want it back. If your not keeping it that is.” she joked.

“I’m sorry, Aubrey, I’m rather stressed out with all this. What with this, the wedding and now the Mikado I might as well be dressed as a girl all the time” I said

“What’s this about the Mikado?” Aubrey asked. When I told her, she let out a squeak and said “That’s amazing — our school is doing it this term as well and I’m in it —I’m playing Peep Bo one of the Three Little Maids. Who are you playing?”

“I’m playing Yum Yum” I confessed.

“But that’s the lead and a big part, wow, — Janette said you had won singing competitions Swimming, singing what else do you do? Gosh, I hope your voice doesn’t break before the big night” she laughed.

“ If I knew how, I’d break it right now. What happens at your school, do girls play the male roles?”

“No, we do the productions jointly with the boys from St Christopher’s, in our big concert hall so we don’t have to do drag acts like your school. Hey, this could be fun, we could practise together, my mum is a music teacher, we could learn together” she enthused.

I thought of her mother teaching me to sing a girls part and my mother making dresses for me and I shuddered, I changed the subject.

“Aubrey, I guess the pictures are off, I’m not going like this. I’m sorry our date has been ruined, but its about time you turned me into a convincing enough girl that I can get home on the train.”

“Yes, I’m sorry Tim, it must be awful for you, lets go into the ladies and I’ll make you beautiful. Well, more beautiful than you already are,” she said.

With that we went into the luckily empty loo and she weaved some magic on my hair and face so when I looked in the mirror alongside her, she said “Hello again Tammy!”

Yes, Tammy was back, all I had to do now was survive the train journey back. We said our goodbyes at the station and I climbed on board the train in my party frock. I suppose it could look as if I was on my way to or from a party, but I felt terribly exposed as the dress had no arms, just two thin shoulder straps and it was short, very short.

A couple of men came and deliberately sat down opposite me, there were plenty of empty seats and they really spooked me, looking at my legs and then up and down my body, smiling and trying to make eye contact. It was a long journey.

Mom was in the lounge with Cathy when I arrived and saw me as soon I walked in the door.

“You really do love that dress, don’t you, said Cathy. Mom saw I was on the verge of tears and came across and got hold of me and brought me to the sofa.

“What’s wrong darling, tell me what happened”, I put my arm around her and told her the story. When I got to the piece about the men on the train, she said, “ Maybe its a good lesson you’ve had about how a girl feels when she is eyed like that, men can be unfeeling and scary when they have the advantage over women on their own, I hope you never do that as you grow older.”

“If he keeps on dressing like this, that will be the least of his problems,” said Cathy, ever helpful and friendly.

“Cathy, leave him alone, he has had a nasty experience and needs to get over it. Timmy, you had better go upstairs and get changed.”

So I went up to my room, and again into my wardrobe went the dress, off came the white shoes, also this time I had a handbag , I sat on the bed in my speedos trying to settle myself.

There was a knock on the door and Cathy came in. “Hey little brother, I’m sorry if I was mean to you there. Thinking about it I guess part of it is my problem, you know, I think I am jealous of you.”

“Jealous, of me! I’m your squirt of a little brother who dresses in girls clothes, remember” I almost shouted.

“Yes, you are my little brother. but you are also a lot more, You are far cleverer than me, you also are good at just about everything you do, swimming, singing, acting, schoolwork, you care about people, I could never go down week after week to help with those old fogeys at the Home, I couldn’t even bring myself to play with the kids like you did at the wedding. People really like you and I know from Janette that Aubrey fancies you. On top of which you are a handsome boy and, yes, you can make a rather pretty girl, when you want to that is. So, little brother that’s how I really feel about you, when I taunt I think its some kind of defence mechanism to cover my own inadequacies —and that’s something I’m just gradually coming to realise”

That was a pretty big speech from Cathy, and I realised it must have taken quite an effort for her to say it. I stood up walked over to her and gave her what must have been the first hug for several years.

“Cathy I’ve always loved you as a sister from when I was very small. You played with me a lot then and I remember the happy times we had. You are a special person to me and I’d be pleased if we could be real friends again” I said.

“There you go again, see, always being the forgiving, nice natured person, that’s why people like you.” Cathy said and continued, “There is one more confession I have to make, I’ve just had a call from John. He was the one who thought up the plan to switch out your clothes and carried it out. 1’ve told him to come around here with the clothes right now and also to apologise to you, otherwise I’ll never see him again.” With that she walked out of the room.

I sat down again and took stock, Today had been a bit weird, but I had done well in the swimming, Aubrey had helped me get out of a real jam and now Cathy had shown me a side of her I had not seen before, an interesting day, Now I was really tired, I just rolled over into bed and went straight to sleep.

+ + + + + +

On Sunday after my session at the Sunhill Old Peoples Home I got ready to go into Bramfield again to meet up with Jason for the concert. Mom was fussing a bit, “Make sure you not back too late and be careful in London.”

“Yes, yes, mom don’t worry, I’ll be OK” I replied.

I met Jason at the station in Bramfield, he was dressed in really cool gear, white chinos and a red and pink striped T shirt. He is taller than me and almost two years older, so I guess I looked like his kid brother. When we met he tried to reach for my hand as if to walk together, but I moved away and put my hands in my pockets. I wished he wouldn’t try to do that. I also remembered I had meant to speak to Aubrey about what she meant when she spoke of Jason kissing me, but with the trauma of yesterday I had forgotten.

He had obviously spoken to Aubrey about the swim meet and congratulated me on my success, “I’d have liked to see you standing on the podium collecting your prizes”. I waited for comments about the dress incident, but he didn’t mention it and I certainly wasn’t going to.

The concert was great and the band really rocked. We got to our feet waved our arms and at other times just sat together. At one emotional point he took hold of my hand and rested it on his knee close to his groin. I didn’t resist but felt a shade uneasy, after a while he moved his hand in closer and I could feel his hardness. At this point he looked over at me and smiled.

I turned to him and said, “Jason, I’m just coming up to twelve and I don’t think I’m ready for that kind of thing, I really don’t want to offend you and I’m not mad or anything, I like coming to the concert with you, but can we just leave it there?”

“Tim, I’m sorry if I frightened you, I wouldn’t want to harm you in any way, please relax, we will just watch the concert” he said.

After that everything was fine. At the end of the concert as we walked to the station chatting about the concert, he really did know a lot about the music, he reached out for my hand again. This time I let him, hell he was nice guy, he had treated me to the concert and I did not want to hurt his feelings.

When we got to the station, we walked through the deserted car park and he turned to me, grabbed my other hand and looked me straight in the face.

“Tim” he said “I’ve really enjoyed tonight, I’m sorry if I scared you back there, but I really would like it if we could meet again and become closer friends” with that he squeezed my hand and started to move his face closer to mine.”

I let go his hand and moved away. “Thanks Jason, I’ve enjoyed tonight as well and yes we could meet again but I don’t want to have you pay all the time. Can we leave it there for now, I’m a bit confused” I managed to say.

We walked silently onto the station platform where my train was waiting. He turned to me and said “Thanks for tonight, next time promise me you’ll come as Tammy!” With that he air waved a kiss at me and went over to his platform.

As I sat on the train, my mind was I turmoil. People seemed to think I was some kind of sweet natured guy who could do no wrong, what they didn’t realise is that I was really confused as to who I was, what I was and people seemed to want to make me do things I didn’t want to do. Where was it all leading?

Next week at school Mrs Cartwright had another session with me. “Your mother called me and has offered to help not only with your costume but with those of the other leading ‘ladies’ as well, that will be such a help, also as she teaches drama she can help you with your part, it is a big part so that will be good. Now here’s the script and the music parts, first rehearsal for you is this Friday.”

“Thank you Mrs Cartwright, I’ll do my best,” I said glumly.

“Cheer up Timothy you know you can do it” she replied.

Back at home mom was already making costumes, starting with mine. “You will need three costumes, including the bridal one, so I’m starting with that” I’ll need your help while I pin it together tonight”

“Bridal dress!” I exclaimed.

“Yes, at the start of the second act, the other ladies have to dress you on stage and do your hair for the wedding, then you sing a song about how beautiful you feel — ‘like the rays of the sun’.” explained mom.

I went off to talk to Aubrey on the phone, anything to get my mind of this upcoming horror. I told her of the plot details I had heard from mom.

“Oh, haven’t you seen it before? I have.” she said “One of the early songs is when all the three Maids, including you as Yum Yum, sing about going to school together, its a famous song, ‘Three Little Maids from school are we.’”

“Enough, I don’t want to hear anymore, what with wedding dresses and little maids I am getting very uptight about this whole thing. It’s all right for you, you are playing the girl parts, and you have boys for the boy parts.” I complained.

“Calm down Tim, you’ll be fine, its no different to playing Dorothy, and Janette said you were brilliant in that,” she said.

“Thanks, Aubrey, that’s just what I wanted to hear. Anyway, when can we next get together, how about this weekend? I asked.

“Tell you what, can you get over here to my place on Saturday, Mummy was going to run through some of the songs with me and Carol, she’s playing the other Little Maid, Pitti Sing, we would have all three little maids then. How about it, you could stay for tea and then we could go into Bramfield for the pictures we missed last week.” she urged.

“What stupid names these characters have, but anyway that seems a good idea, I could get over there about 1 o’clock or 1.30, is that OK?” I said. Then I asked “Aubrey, you know I went to the Speed Dragon concert on Saturday with Jason?”

“Yes, he did say he was going with you, did you enjoy it?” she asked.

“Yeah, it was great — and it was his treat, that was kind of him” I replied.

“And…..?” she queried.

I didn’t want to ask straight out about Jason, so slid away from a direct question. “No, its just I wanted you know that I had been out with him, in case he hadn’t told you” I said a bit lamely.

“Tim, I need to talk to you a bit about Jason, but now is not the time, he is in the house and moving about so he might hear, we’ll talk Saturday, OK?”

“Yeah, that’s fine, no hurry. See you then,” I replied.

Friday night came and after dinner mom had me undress and stand on a chair in the lounge while she pinned up the wedding dress costume. “Its got to be easy to put on , as you have to get dressed on stage, the other two little maids do up your hair, then put you in the dress. You will have it on for the rest of Act 2” she said.

“Brilliant, that’s just what I wanted to hear. What will I be wearing before the dress goes on?” I said.

“That will be bridal underwear, I think we will buy that for you though, we can go for it one night next week after school or maybe go into Bramfield at the weekend” she replied.

“Oh yes, we will need to make sure everything fits. Plus we will need to get a wig, Your hair is very blonde, Japanese ladies all have black hair” she explained. “Stand still and turn around while I get the back of your dress adjusted.”

At this point Cathy came in, I glared at her. But she surprised me , “Don’t worry Tim, I won’t say a word” she said, stifling a giggle.

“OK , you can take it off now, but stay down here, I’ll make a few adjustments and we can try it on again” So then mom and Cathy helped me out of the dress and left me standing in my boxers.

Cathy couldn’t resist asking “Oh, he’s not wearing the right underwear, doesn’t he have too?”

“Oh yes, we need a bustier, a slip and silk stockings - he has to sing a song upstage before the dress goes on” mom explained. I was getting a bit tired of hearing about this part, also beginning to dread it.

Mom was another hour before she let me go, Then she said. “That was very helpful, Tim, I get done much quicker when you model the dresses like that. Now that I am going into full time commissions for dressmaking you can be my model, I will pay you extra pocket money”

“Please mom, leave it for now, I’ve had it up to here with dressing up these last few weeks and now I’m going to have another six weeks for the Mikado” at which point I stormed out.

Saturday, and I headed off to Aubrey’s house. Her mom opened the door and said “Well its the third little maid, come on in Tim, Carol and Aubrey are in the front lounge, that’s where the piano is”

When I walked in the room, as well as the two girls, there was Jason sitting on the couch. “Hi Aubrey, and Hi Jason, I wasn’t expecting to see you here. Oh and hello Carol, or should I say Pitti Sing?”I said

“Jason is in the Mikado as well Tim, he goes to St Christopher’s, he is playing Nanki Poo, that’s the character that marries Yum Yum” said Aubrey. A vision passed before my mind about the marriage ceremony and the wedding dress and me and Jason, I quickly tried to banish it and said “ Well does anybody know the words yet?”

“Don’t worry about that, we’ll start just singing from the sheets, lets start with the Three Little Maids. I’ll play it through first” said Aubrey’s mom.
As she played it, I read the words and cringed .

“ Three little maids from school are we,
Pert as schoolgirl well can be
Filled to the brim with girlish glee
Three Little Maids from school”

And so it went on.

Soon I was singing along with Carol and Aubrey and after a three runs through we were singing together quite well.

“That’s very good girls, … er and Tim. You have a lovely treble voice Tim and you project well, you must have sung on the stage before.”

After a while we broke for tea. Carol was a nice girl and didn’t josh me at all. In fact we started singing songs together, the Three Maids song is infuriatingly catchy, and we started singing and making up new, rather rude, words. Jason who was with us, seemed a bit left out of our chatter, especially when we got onto discussing the dresses. Carol and Aubrey were fascinated when I told them about the underwear and wedding dress.

“Oh, if you go into Bramfield for the lingerie, you must let me come as well, to help you choose” said Aubrey. Oh, brilliant, I thought, my would be girlfriend helping me buy bridal underwear, just what I need.

Aubrey’s mom prepared tea for us and after she laid out the things she turned to me and said. “Tim, I understand you haven’t seen The Mikado,” I nodded, “Well I have two tickets for next Saturday’s matinee at the English National Opera I got them through my work with the choir. How would you like it if you and Jason went up to London to see it next week?”

I looked at Jason, who was beaming and then across to Aubrey who looked a bit upset.

Her mom saw this and said, “ Well Aubrey has seen it already, and I think at eleven you are bit too young to travel around London if you haven’t been on your own before. Jason is nearly fourteen and goes up to town for his ballet lessons. I will be happier if he takes you.”

“ That is very kind of you,” I said “ I must admit I would love to go to a real Opera House and see the show, are you sure you don’t mind Aubrey?”

“No, you go Tim, I’ve seen it and mom’s right Jason knows his was around London” she replied.

“Well thank you then,” I said, turning to her mom

After tea, Aubrey and I caught the train to Bramfield. When we were on board I said “Jason seemed a bit out of sorts earlier today,” trying to bring the conversation around to him and find out what Aubrey meant in her earlier comment.

“Yes he gets moods, he doesn’t have a happy time at school and doesn’t have many friends,” she said.
“What’s his problem then? We seem to get along all right, I asked.

“ Well the other guys give him a hard time.He is more interested in art, music and dance, - he takes ballet lessons, plus his mannerisms make some guys think he is a bit strange. Boys can be cruel at times can’t they? Didn’t you say you have guys getting at you after playing Dorothy, doesn’t that bother you?” she asked.

“Not really. The guys who call me names are the losers anyway. Most of the mainstream guys know I swim for the school team. Because of that and my grades, I was elected deputy form captain, so I can get away with things like Dorothy, anyway I do with the guys that matter. I must admit this Mikado deal is scaring the pants off me though.” I replied. Then I realised what I said and Aubrey burst into fits of laughter.

“Yes, you’ll lose your pants again, that’s for sure” she joked.

“The thing about you Tim, is that you try hard and seem to excel in just about everything you do. People recognise this, I certainly do. How do you find time to do everything?”

“ Well two nights a week I do swimming practise, one night piano, now I’ve got two nights for Mikado rehearsals and on Sunday afternoons I go to the Sunhill Old Peoples Home , the rest of the time is homework , learning the guitar and now meeting with you” I explained. “But that’s me, I was asking about Jason. I can’t keep on going out with him and him paying, plus, to be honest I wonder why he likes me?.” There, I’d asked it.

“Oh Tim, its just he is lonely, he doesn’t have any real boy friends or girl friends, that’s why I was pleased you were hitting it off with him, you might give him a bit of your confidence” she said,

“But if he can do a part, a big part in a musical like the Mikado, surely that takes confidence?” I queried.

“When he is acting, he becomes a different person, he really is very good. Its as though he only gets to grips with things when he is playing someone else. That’s why I’d like you to help him if you can,” she said.

Oh dear, that’s not what I wanted to hear. OK then, I decided , I’ll go for broke. “But you warned me about him kissing me” I said bluntly.

“ Come on Tim, when I said that you should watch out for him, you were dressed as a rather good looking girl, no, make that a very good looking girl, and it was meant as a joke not a warning” she then said.

I decided to leave it there. Aubrey obviously did not know or realise there may be another side to Jason. If I told her my suspicions it might hurt her and also damage our friendship. But that left me with the problem of Aubrey wanting me to be friends with him. Why is life never simple? That is a question for another day, I decided. Aubry would understand that, I hoped.

When we reached the multiplex I let Aubrey choose the film. She chose a real weepie. It was about a man (an Englishman) who married a divorced woman (an American) who had a young child, a boy about nine. The woman developed a fatal cancer and died. At the end the man and the boy, who had tried to be formal and strictly correct with each other suddenly both realised that they had to let their grief out, they just held each other and wept. The closing scene was so emotional that I wept as well.

When the lights went up we turned to each other, I saw Aubrey’s eyes were moist. She saw the tears running down my cheeks as I tried to brush them away with my hand.

“Gosh, that film really got to you didn’t it Tim, don’t you have a hankie? Here let me dry you up with mine”

I tried to explain, “I guess I was identifying with the boy. He lost his dad, like I did, when they divorced, then he lost his mother and the final scene really upset me. I’m sorry to be such a wimp”

She turned and grabbed me in a hug. We were still sitting in the emptying cinema, but oblivious to the people around is,

“Tim, stop apologising, you absolutely don’t need to. Maybe you needed to let go a bit over losing your dad. He is in America, isn’t he? Do you never hear from him?”

“No,” I replied, “He pays for school and sends money at birthdays and Christmas, that’s it”

“It’s a pity he doesn’t know what a wonderful son he has” said Aubrey.

“ Maybe he just doesn’t care, anyway I hardly knew him, I was four when he left” I didn’t tell Aubrey I thought about him just about everyday and looked at the one tiny photo I had of him and kept in my wallet.

We walked back to the station in subdued mode and arranged to meet in Bramfield before Jason and I went into London on the following Saturday.

Mom was awful during the next week. She was now busy dressmaking both my costumes and others on commission. She had me modelling for her every night after I got home from swimming or rehearsals. I found it easier just to undress and for the intervals when she didn’t need me she handed me an old dressing gown of hers which I wore while I went back to homework or piano practise. It had a yellow and white silky looking pattern and was quite ridiculous .

When I objected, mom said “ Look Tim, your dad only pays for your school uniform, things are going to be a bit tight until I get the dressmaking business running properly, meanwhile you are going to have to make do with what you’ve got or whatever there is in Cathy’s wardrobe that fits” I kept quiet at that point.

Cathy was getting ready to go to college and one night while I was standing in yet another frothy looking party frock she came in and asked Mom. “What are you going to do with Janette’s room now she is leaving, can I have it for when I’m on vacation from college?”

“Well my plan is that Timmy moves into Janette’s room, its bigger for a start and I use his old room for my dressmaking, so I don’t have to clear up the lounge everyday” mom told her .

Cathy wasn’t pleased at that, but kept quiet. I liked my room as I had it decorated just like I wanted with places for posters and my swimming trophies and other kit. Janette’s room was indeed bigger but she hadn’t changed it much from her early teen years, so it was all pink and white: walls, carpets and curtains, not my idea of a cosy room. I started to object, but mom silenced me .

“ No arguments Tim, that’s what is going to happen, Now change from that party dress into your wedding dress, its just about finished, oh yes and put on those shoes,” she said, pointing to some fancy decorated high heeled white shoes, “ I want to get the length right while you are in your heels”

“ Mom, do I have to do all this? Its only for two nights, who will notice?”
I complained.

“Tim, to make convincing drama you need to pay attention to every detail, that includes everything from underwear to shoes to hair and makeup, so just do as I say” Its useless arguing with mom when she is in one of her determined moods, so I did as she asked. Cathy looked on and helped me change dresses, but she was silent for once looking sympathetically at me while she did it.

On the Thursday morning mom said to me,” Tonight, after school, we will go into Bramfield and buy your bridal underwear, its late night shopping”.

“But mom this is crazy, we can’t afford new clothes for me, yet you want to buy this stuff for a two night play” I exclaimed.

“ Mrs Cartwright has a grant to cover costumes and she says she can keep them and use them for other productions - so it’s the school that is paying. Tom just stop complaining and do as I say” she said firmly.

So, after school that day, I met mom at the station. She was carrying a garment carrier. I noticed it was not transparent like the one she gave me two weekends ago.

“This is your wedding dress, I’m bringing it just to make sure everything fits properly” mom said.

“But I thought I was just going to get measured up,” I said, getting very uneasy.

“Oh no, I gave them your measurements two weeks ago, it should be ready by now.” Said mom confidently.

In Bramfield, I followed mom like a condemned man into Amelia’s Bridal Shop. It was wall to wall white wedding dresses and multi coloured bridesmaids outfits — my mind went back to Janette’s wedding and my awful experiences there. I felt weak at the knees.

Three ladies stepped forward as we entered, two younger girls and an older large lady who spoke,” This must be the young boy bride and you must be Mrs Bramlett,” she said as she walked up and grasped my two hands. “Let me look at him”

“Oh yes, what a gorgeous face and I understand you have a beautiful voice, yes, we will make you into the loveliest Yum Yum ever. Is that the dress? She asked pointing to the carrier.

Mom proudly unwrapped the wedding dress and held it out to a chorus of “oohs” and “ah, isn’t it lovely” and similar remarks.

“Well into the changing room and lets get you ready”, With that all three ladies and my mom walked me into an inside room lined with mirrors on two sides, bringing in the dress and what I assumed were the other clothes. I hesitated, were they expecting me to change there in front of them all?

I was still wearing my school clothes and mom came up and started to undress me, taking off my jacket and starting on my tie. “Mom, I can do this myself, please let me go somewhere and change, just give me something to change into” I pleaded.

“Come on Tim, these are professional people and they are here to help their customers dress and undress, just be quiet while we get you ready.” Mom instructed.

I don’t seem able to win arguments with mom when she is in these moods so I decided it was better just to get this over with rather than argue.

It was still excruciatingly embarrassing as mom with the help of Amelia and watched by the two girls removed all my clothes. “ There now lets put on these special panties, they will help you keep those little boy bits all flat and smooth,” said Amelia, “ as she held up a white brocaded set of panties. They were quite brief but felt very tight, much more so than the ones Cathy had loaned me.

“Now, here is the really special piece” she said holding up a cream and white lace frilled and again brocaded garment with what looked like ribbons dangling from it.

“What is it?” I gasped, trying to move away, but hands were holding me.

“Oh its beautiful” said my mom “ It’s the long line bustier I told you about, it’s a kind of corset or basque. Its what ladies wear to give them a nice figure, “It will be perfect.”

The two girls took the garment from Amelia and held me while they wrapped this awful thing round my body and started pulling it together at the back. I then saw it had a bust area built in, so it gave the appearance of having real boobs. They pulled it tight at the back, then they threaded those ribbons through my panties. I started to feel a little faint and held out my hand to steady myself.

“Oh, he is getting all dreamy in his lovely underwear” said one of the girls, “. come and sit down here while we put your stockings on.”

I sat down, almost collapsed, and watched them as if this was happening to someone else, as they picked up a pair of flower patterned white stockings and pulled them up my legs and attached them to the ribbons which had small tabs on the end.

“There now, almost done, all you have now is your peignoir,” said Amelia, holding out a longer garment looking as if it was made of transparent material. “This is chiffon , it’s very sheer so as not to hide your pretty underwear,” so saying she placed this garment round my shoulders and tied it loosely under my bustline. “Now have a look at yourself, my young bride” she exclaimed.

I turned to mirror and gasped. The only time I had seen anything like this was in the clothing catalogues mom had delivered and that I secretly looked at. But now I was wearing it. Every time I moved the loose front of the peignoir parted so you see all my legs right up to top of my stockings and even my panties. I could see in the mirror the reflection of the mirror in the opposite wall, I looked even more ridiculous from behind.

“Don’t you just look adorable” said Amelia “ Can you sing us one of your songs now?” she chortled. “Oh ,yes,” said mom, “come on Tim”.

“No, I can’t, my mouth is dry, I’m feeling faint and these clothes are uncomfortable and so am I, its crazy dressing me like this” I moaned.

“ Look Tim, I won’t have this. Boy’s playing female roles is a theatrical tradition going back to Shakespeare’s time, they still do it sometimes today to show what the real theatre was like, you should be proud to be part of that tradition” mom said.

“But mom this is such an embarrassing outfit, couldn’t I just wear the dress?”

“Oh, yes, the dress!” said mom , “quick, its getting late, lets try the dress on him to make sure it fits”

Then I was hauled back across the room and fitted into the dress. “This is designed so it can be fitted on him quickly on stage, so there are Velcro fastenings down the back. Now let the girls take off your peignoir and step into your dress dear.”

I stepped in and the dress was drawn up and fastened firmly behind me. I felt it clasp close and tight around my boob area, which now with the addition of the dress material and its flounces felt even bigger. The dress had a huge skirt and layers of petticoat like material underneath. I recalled I would have to wear this for just about all of the second act.

“That looks just so wonderful, honestly we have brides who come in her who aren’t half so beautiful,” cooed Amelia, and then the girls joined in with similar remarks. But as I have had to do before, I tuned out and let it pass over me, I just wanted to get this whole evening over with.

“ Well thank you Amelia, its time we got our young bride home again, so lets get him changed again. So off it all came, the dress, the corset thing, the stockings. Interestingly the girls let me take off the panties and put my school clothes back on, I think by now they were a bit sorry for me. One of them came up to me and said. “Good luck with the show, young man, I think you are very brave to play a role like that, but I really don’t see why your costume has to be so elaborate for a school production”

“You don’t know my mom, she has her own ideas of how I should dress up” I’ve had this for a while now, but I’m still not used to it.

Mom had settled up with Amelia and we left for the station and the train home. As I sat I thought about what the girl had said, I would have to stand in front of the whole audience dressed in that see through sort of nightie wearing stockings and a corset and stand up front, centre stage, and sing of my undying affection for a guy called Nanki Poo and then put on a wedding dress. I shuddered and tried to drive the image away.

“Are you all right dear, are you shivering?” said mom.

I didn’t want to talk, I just said, “I’m OK”

I thought ahead, Cathy was leaving this weekend, I had my ‘date’ with Jason at the opera on Saturday, Gosh what do you wear to go to the English National Opera? I thought, I have no decent clothes, only my school uniform and I’m not wearing that, if I asked mom she would just say ‘find something of Cathy’s’.

At least I would see Aubrey for a while on Saturday and on Sunday Janette, back from her honeymoon was calling in to pick up some of her things and I needed to talk with her about mom, she was the only one I could trust.

+++++++++++++++++++++++++++++++++++++++

To be continued

+++++++++++++++++++++++++++++++++++++++++++++

Crossdressing with my Girlfriend and Boyfriend -3- Tim’s Debut at the Opera

By Cindybelle
C June 2007

Tim’s date with Jason at the Opera brings some surprises, though his mom’s
behaviour seems to be getting more bizarre. Can his sister, Janette, help?

++++++++++++++++++++++++++++++++++++++++++++++

At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. “She has just about finished two dresses for me, including the wedding dress,” I said

“I’m sure they will be very pretty, she did so well with your costume for Dorothy last time, I can’t wait to see them,” replied Mrs Cartwright.

I thought about telling her about the bridal underwear that mom had bought for me, but that brought the whole episode back to mind and I just could not bring myself to mention it.

When I got home after the rehearsal my mind turned to what I could wear to go to the Opera tomorrow. I couldn’t face asking mom about it, so I went along to Cathy’s room to ask her, she had sort of relented on me recently so maybe she would be helpful I thought.

I explained, “Cathy I’m going to the Opera in London tomorrow with Jason, and I don’t have any suitable clothes, I’ve just got my school stuff and casual jeans and T shirts, what on earth can I do?”

“The opera, with Jason? I didn’t know you were into opera Tim and why Jason, don’t you want to go with Aubrey? How did you get tickets?” She queried.

I answered her queries , that it was the Mikado and Jason’s mom got the tickets but said Aubrey and I were too young to go up to London together,

“I’d much prefer to go with Aubrey, but it doesn’t look like its an option” I said.

“Well then let’s see if I can help, Jason is a snappy dresser so we’ll have to make sure you look good. This is where you have it tough Tim, being the younger sister I got Janette’s cast offs, but that doesn’t help you does it?” said Cathy.

She went over to her other wardrobe and searched in it for some of her older stuff which she had kept from when she was smaller.

“How about these slacks Tim, they’re black, they are made of Lycra so are pretty comfortable and they look the right length,” she said as she held them alongside me.

I took them from her, they looked OK, even had a fly front. “They might do but they look a bit on the slim side around the top,” I said.

“Only one way to find out, try them on” urged Cathy.

I took them from her and tried to undo the fly buttons, but there weren’t any. “No, no that’s just part of the design, they button down the side, look” said Cathy, opening four little buttons down the side.

“Oh, I see” I said, a little less sure this was going to work. However I took off my jeans and pulled on Cathy’s slacks. They did fit OK, the length was fine, but they were very close fitting around my trunk.

“Well they are alright, but you can’t wear them with boxers Tim. Look, Lycra is a stretchy fabric and you can see the outline of your boxers all crumpled up under the slacks. You will have to wear panties underneath, also that will help tidy you up at the front, you don’t want to show a bulge, do you?” said Cathy.

I looked down, she was right, the front was very tight, and the outline of the boxers showed through very distinctly. “I guess that’s the only way this will work” I said.

So out came a pair of her panties, white this time and with only a tiny bit of lace around the waist and legs, “That’s about the best I can do Tim” she said as she held them out for me.

“Thanks, Cathy. Do you have any shirts I can wear with a tie that might be suitable?” I asked.

She came back from her wardrobe with what was definitely looked like a shirt, it was a kind of check pattern, pink and white. “I know you may not like the colour Tim, but honestly pink is an in colour for men, even John has a couple of pink shirts now” she said.

“All right, I’ll try it then” I said. So I took it from her and started to put it on. I found I couldn’t do up the buttons and as I was struggling, Cathy said,

“No Tim, this shirt buttons up the other way, here let me do it,” So she took over.

When she was done I walked over to her mirror. I was not too impressed by what I saw. The trousers were all right as long as you didn’t look too closely, the shirt however had a rounded collar, not pointed like on a mans shirt and the pink was a bit strong for my taste.

“Now with a tie that will look very smart, and you do have that real nice leather jacket that Janette gave you last Christmas.”

“I guess this will have to do, but I wish I had a proper suit or something” I said sadly.

“Oh Tim, I’m sorry, if mom and I hadn’t concocted that outfit for you for the wedding we could have got you a suit then and it would have done for today as well” said Cathy.

“Well its too late now, but thanks for your help,” I replied. So, off to my room I went, where I tried on my leather jacket. I really loved the jacket that Janette had bought me. With the jacket on I didn’t look at all bad as long as you didn’t look too closely at the shirt collar.

I had arranged to meet Aubrey at 10 o’clock in Bramfield on the Saturday morning and Jason would meet us around 11.30 at the station coffee bar before he and I caught the train up to London.

“My, you look smart” said Aubrey as she walked up to greet me.

“And you look gorgeous as always” I replied. She really did. She has lovely long flowing brown hair that frames her face and was wearing a yellow and green checked skirt and green top.

We walked around the shops, just window shopping and chatting, With mom’s dressmaking I guess I’m fairly knowledgeable on clothes, so I enjoyed chatting with Aubrey on what she liked and what I liked and making comments on people we passed. She was so easy and fun to talk to, before this I had found with other girls that it is sometimes difficult to really find common ground, but with Aubrey time just flew by.

“I wish I was going with you today Tim” she said as we walked hand in hand down the High street.

“Yes, it would be so nice if we could have gone together, I mean I like Jason, but it would have been different with you,” I replied. “You must come through to my place next week, there is a swimming competition at my school and we could go on somewhere afterwards.”

“Oh yes and maybe I could see the dresses your mom is making for you, I’d love to see your bridal outfit.” said Aubrey mischievously.

“She will probably have you modelling for her if you come, I seem to spend most of evenings acting as a model right now”

“You mean she uses you to model all her dresses?” queried Aubrey.

“ Since she gave up her job in Bramfield, she now does dress making full time, so she sort of relies on me to help, I don’t like it but I promised I would help as much as I could.” I explained.

“Tim, I think you do too much, it’s really not fair for her to rope you in to model dresses for her, maybe if I come round next week I could stand in for you,” she suggested. “You are too good natured, you need to learn to say no.”

“Believe me I try, Aubrey, but mom knows how to lay down the law, you’ll see if you come round next week.”

Very soon it was time to meet Jason at the station. “We have time for a coffee before we catch the London train, come on, my treat,” he said.

The station coffee bar was hot, so as we started to sit down I took off my jacket. I turned and saw both Aubrey and Jason were looking at me. “What’s the matter?” I asked.

“Let me look,” said Jason, as he examined closely my trousers and shirt, “Well I see you did come as Tammy, after all, those are girls slacks and that most certainly is a girls shirt.”

“Oh, is it that obvious?” I quailed.

“Yes, Tim and its also obvious from the outlines under those tight slacks that you are wearing panties, why have you done this, do you like wearing girls things?” asked Aubrey.

“No, its not that, its just that I have nothing smart to wear, so I had to borrow some things from Cathy. Mom doesn’t have a lot of money especially now she has changed her job, and I’m the only boy in the family and seem to be last in line for clothes of my own” I explained.

“I’m sorry Tim, I hadn’t realised, I think you look nice whatever you wear, don’t worry. Jason, you must look after Tim and not hassle him over this.” said Aubrey.

“I’d never do that,” said Jason “I’m fine with Tim just as he is, I don’t mind how he dresses, in fact I think he looks just great as he is,” replied Jason.

After the coffee I said my goodbyes to Aubrey and then Jason and I got on the train for London. We had a weird experience on the train. The train had separate compartments and we initially got one to ourselves. I took off my jacket and Jason sat next to me and we chatted for a while. He then reached for my hand again and just held it loosely, but as it was resting on my knee this time, I let him go ahead.

Just then the compartment door opened and in walked an elderly lady, “I hope you don’t mind me joining you there aren’t any empty compartments left?” she said.

After a few moments once she was settled she said “Well, you do make a nice couple, I know girls and boys start going together much younger these days. That is a lovely blouse you are wearing young lady,” she said.

I looked over at Jason, who was smiling. She must be short sighted I thought. Jason played it for laughs, “Yes isn’t she pretty”, he said and he turned towards me and kissed me on the cheek.

“I wish young girls didn’t wear trousers so much, I think a skirt or dress is so much more feminine,” said the old gal . “What do you think young lady?”

“I….I prefer a skirt as well,” I stuttered, “Its just that for a day in town and a visit to the opera I thought these slacks would be better”. I reckoned it was easier to keep up the pretence, than try to explain.

“Well do enjoy yourselves, and you look after her young man,” she said as the train pulled into London.

“Oh, yes I will,” said Jason, “She is my very special girlfriend”

Oh, yuk, I thought, how do I keep on getting into these situations. As she walked away, I turned to Jason and said, “Look Jason, It’s one thing playing a joke on that old lady, but I really don’t want my visit to the opera spoilt if you are going to be behaving as if I was your girlfriend, please let’s quit the playacting and then I can relax a bit.”

“I’m sorry Tim, I didn’t realise it was upsetting you so much. I promise I’ll behave like a gentleman.” He affirmed.

“You don’t have to go that far, just behave as if you were my brother or better yet, my cousin, which is what you are, remember?” I replied.

We walked round to the theatre and took our seats. The Opera Company was based in the Coliseum Theatre and it was enormous. Our school hall seats 400. According to the programme this theatre holds over 2,300 on 4 levels. We had fantastic seats in the sixth row of the stalls, right in the middle.

After the huge orchestra had played the overture, the curtains opened. The stage was gigantic, from our seats it was all you could see and the opening scene was a real stunner, a brilliantly lit white set with the whole cast and chorus coming on dressed in black and white, over forty of them. If this is opera then its fantastic I thought, I was thrilled and I grabbed hold of Jason’s hand without thinking, he turned to me and waved his finger from side to side as if to say ‘don’t do that’. I smiled sheepishly and took my hand away.

At the interval a large lady who was sitting next to me, turned to me and said “Its nice to see youngsters enjoying the show. You must have saved up a long time for seats as good as these?”

“This is my cousin Jason and his mom got the tickets through her choir and as we are both playing in our schools productions of the Mikado she let us have the tickets. I’m Timothy, by the way,” I said, just to make sure there would be no more girl / boy mix ups.

“Oh, that’s interesting. What roles are you going to be playing?” she asked.

“I’m playing Yum Yum — I go to an all boys school, but Jason is playing Nanki Poo at his school — they do it jointly with a girls school.” I explained.

“What do you think of the lady playing Yum Yum here today?” asked the lady.

“I think she is brilliant. I only hope I can pick up some tips from her as I watch,”` I said.

“Well, would you like to meet her and see if she can help you?” She asked

“What do you mean?” I said, startled.

“ I’m Anita Jenkins and Miriam Jenkins is my sister, I can take you back stage after the matinee and you can meet her,” she said. I looked at the programme and sure enough it said Yum Yum played by Miriam Jenkins.

“ Well that’s very kind of you, but are you sure, won’t she be wanting to get changed and leave the theatre?” I said

“No, she has to do the evening performance so she won’t be leaving the theatre and she loves helping young people,” she said.

We then watched the second act. This was the part where Miriam came onstage ready to put on her wedding gown. I was astonished therefore to see she wore a very opaque white gown when she first came on, you could hardly see even her ankles, it was nothing like the outfit mom was providing for me with the transparent peignoir and the corset and stockings all on show.

Then when it came to putting on the wedding dress, the gown was removed and underneath she had on a long slip or petticoat, you never saw any revealing underwear at all. What is going on with mom, I thought. I needed to talk with Mrs Cartwright next week and try to get her help to stop mom going overboard on her outfits for me.

At the end of the show, Anita took us through a maze of passages and corridors to the dressing rooms and into Miriam Jenkins room.

“Miriam, this is Timothy and this is Jason, they are both playing in their schools own Mikado productions, young Timothy here is playing Yum Yum,” said Anita.

“ Gosh that’s a big role for a young boy like you. Do you know any of the songs yet?” asked Miriam.

“Well there is the three maids song, plus I’ve done the solo ‘The sun who’s rays are all ablaze’ the one you sang in Act 2.” I replied.

“Do you want to let me hear you sing that and see if I can give you any advice, I have a keyboard here” she said pointing across the room.

I started saying “Would you do that? I mean it’s only a school production and I….” but she interrupted me.

“Timothy, if I don’t have time to help and advise young people then I’m not a good representative of my profession, now stand over there and I’ll play the introduction, and off we’ll go,” she said.

So I took off my jacket and stood, very nervous, as she played the introduction, she nodded to me and I started the song. I thought she might stop after the first verse, but she continued all the way through. When we got to the last line “we are very wide awake, the moon and I” Miriam turned to me and with Anita started applauding, Jason joined in as well. I could feel myself blushing furiously.

“That was really very good, your phrasing and expression and the way you project your voice is wonderful, you have a lovely voice. I could only pick out a couple of times you went very, very slightly off key , you have a gift young man.” Said Miriam, “Which school do you go to?”

“Charterborough. It’s in Surrey” I explained,

“ I know where it is, I live just five miles away, I had a son of my own there a few years ago. Is Mrs Cartwright still in charge of drama and music?”

“Yes,” I replied.

“ Well I’ll give her a call and see if she wants any help, I used to help before and if the rest of the cast is as good as you are, I’d love to see the show myself. Now, would you like to sing on the stage of the London Coliseum, Timothy? Come with me and we’ll fix it for you.”

So saying and before I could speak, she took me by the hand and we swept down the corridor and eventually made our way on stage. The curtain was up and auditorium was empty apart from some people tidying up, there were some stage hands rearranging the set for the evening and a pianist, apparently practising, was playing in the orchestra pit.

“Is that you Alastair? Could you help accompany this young man in the second act Yum Yum solo please?” she asked. He nodded. “Right then Timothy , stand there centre stage and imagine there are 2000 people out there and you want them all to hear.”

I gulped and looked at the vast auditorium, Miriam had a loud voice and everyone working in the place had stopped and was looking at me as I walked up to the front of the stage. I was really nervous and my legs were turning to jelly. Jason whispered to me as I passed him, “Go for it Tim, break a leg!” That made me laugh a little and just broke my tension at the right moment.

The pianist struck up the introduction and I launched into the song, trying to remember to reach out into the auditorium, my nervousness went and I even managed to do some of the stage movements and gestures Mrs Cartwright was teaching me.

When I reached the end everyone applauded, even the stage hands, Miriam came up and grabbed me and said “Well how do you feel now, after your first solo performance at the London Coliseum?” I looked at her and then around the vast theatre.

“That was the most amazing experience, ….I can’t thank you enough, …you have…. been so kind….” I struggled to speak , and then I’m ashamed to say I started weeping with the emotion of it all. One minute I’m dreading life when my mom is forcing me to do things I don’t want to do, then I meet people who are so kind and helpful. It is all so confusing I thought.

“ Oh you sweet boy. Come on Timothy, I think you must have had enough excitement for one day” said Miriam. “Its time for me to get ready for this evening and you two better set off home. I’ll be in touch with Mrs Cartwright” with that she gave me a hug shook Jason’s hand and then Anita escorted us both out of the theatre.

“You were very quiet there Jason,” I said as we walked back towards the station “ I’m sorry if I sort of monopolised the time with Miriam Jenkins.

“It’s not necessary to apologise Tim, you were the centre of attention and deserved to be, hell, your singing of that song was better than the girl who is going to be doing it in our production, her voice is thin and weedy compared with yours. She was right, you have a gift,” said Jason.” Tell you what lets walk down the Thames embankment for a while before we catch the train home, it’s a nice night.”

“OK then, you’re right it is pleasant,” I said. I felt very happy at that moment after the experiences of the afternoon and reached out and took hold of Jason’s hand as we walked along.

“Did you see the reaction when you took your jacket off in Miriam’s room as you started singing?” asked Jason.

“Reaction, what reaction?”

“Miriam noticed your girls slacks and blouse and pointing at them looked across at Anita with a puzzled expression. Anita just made a shush, keep quiet sign to her, and she let it ride.” Jason explained. “Later when you were singing on stage Anita asked me about it, I just said you were more comfortable in girls clothes.”

“You what!!” I yelled, taking my hand away , “Jason, stop right there, how could you, its not true, and now you’ve made me look a fool. She is coming to my school remember!!”

“Whoa, got you that time, Tim. Look all I really said was that money was a bit tight and you just borrowed stuff from your sister so you looked smart. She just said ‘Oh what a shame I’ll see if Miriam can help in some way.”

I relaxed a bit at that and we resumed walking until we reached a point where we had a view across the river to St Pauls. Jason suggested we sat down, he took my hand and put his arm around my shoulder. There was something comforting about that, so I snuggled up a bit closer to him. It was a nice feeling, I felt a little drained after the singing in such a big place and I day dreamed for a while of actually performing there.

“Tim, you know I promised I would never come on to you as long as you didn’t want to me too,” Jason said quietly. I’m finding it very hard not too right now”

Around us on other benches were courting couples, doing what couples do on a Saturday night. I turned to him and looked at his handsome face, he was such a nice boy, I felt sorry for him but at the same time also scared of what I might let myself in for. “Jason, if you wanted just to cuddle a bit, I guess I wouldn’t mind too much,” I almost whispered.

With that he took hold of me tightly and I put my head on his shoulder, then I turned towards him and gave a slight peck on his cheek. I could feel him tense up, so I turned away again. But I felt a tingle myself at that time, I know now that was the first early stirrings of puberty, but at the time I didn’t fully realise what it all meant.

We stayed like that for about half an hour, then slowly walked back, his arm round my shoulder. No one paid any attention to us we were just another young couple walking together — somehow it was a nice feeling.

On the train home we still held hands. In the brighter lights on the train a few people looked at us but there were no comments. At Bramfield station we said our goodbyes.

“Tammy, I really enjoyed today with you, it was wonderful to see you on stage at the Coliseum, I was so proud of you. I think you belong on stage and in beautiful costumes.” said Jason.

“Well I’ve had a fantastic day, both the opera which was superb and the experiences afterwards, and I include our walk down the Thames in that” I added. I reached up intending to give him another peck on the cheek to say goodnight, but he grabbed my face in his hands and kissed me hard on the lips. “I’ve wanted to do that all night, I’m sorry Tammy, I really do want you, I can’t help it.” I looked up at him, there were tears in his eyes..

But with that he turned straight away and walked, almost ran, across to his platform. I looked after him thinking ‘oh what have I done now, how do I get out of this and what about Aubrey?’ all these thoughts crowded in on me, I felt dizzy so I sat down and tried to collect myself while I waited for my train. Tomorrow I decided I would really have to have a long talk with Janette.

When I got home, as soon as I walked in the door mom said “You are later than I expected, I wish I had time to go to the opera. I’ve been dressmaking all day, now I need your help to fit and shape some of these dresses”

I felt crestfallen. I was planning to tell her about my singing at the Coliseum, I thought she would be proud. But all I got was, “Well I see you’re already in girls clothes, so take those ones off and let’s get started.”

I took off the blouse and slacks and stood there. “Oh, already in panties as well, that’s good, because this first dress is for a 14 year old girl who has a bust line so you need a bra also. So saying she picked up a white lacy bra and tied it round me, and put two pads in the cups — this was getting weird again, I felt.

“So you don’t soil the dress you had better wear a slip as well,” so saying she dropped a long pink satin slip over my shoulders, “Yes that’s better, now lets try on the dress, then stand on that stool”.

I stood there while mom pinned and tucked the dress for what seemed like ages. After a while she said, “This isn’t working properly, I need to see how the dress hangs when you are wearing heels. Those shoes and tights you wore at the wedding are still up in your room, go put them on and I’ll see if I can finish this dress tonight”

I trudged upstairs and retrieved the terrible orange satin shoes and the tights, even looking at them brought back memories of that awful day. I wriggled into the white tights again and eventually figured how to buckle up the shoes and downstairs I went now completely dressed in girls underwear bra, panties, tights and a slip, plus the very uncomfortable shoes.

“Now, lets get the dress back on you for a while, I shouldn’t be much longer” said mom.

After a few moments the front doorbell rang. My mom went to answer it leaving me there. I heard her chatting for a while, and then I heard her say, “Come on in” to whoever it was.

Oh no, I thought, who is she inviting in while I’m stood like this?

It was Mrs Pugh our next door neighbour followed, I was horrified to see, by her nine year old daughter.

“ I’ll just finish up this dress which Tim is modelling then I’ll measure up Teresa for her birthday dress,” said Mom.

“Oh, what a good boy to help your Mom like this,” said Mrs Pugh, “I’ve got to say you look very nice, doesn’t he Teresa? and you’re wearing the shoes and stockings. I could never get our Tony to do anything like this.”

I didn’t speak, I was too embarrassed. “What a pretty dress and you make such a pretty girl,” said Teresa, as she and her mum walked all round me as mom went on with her work.

“Maybe Teresa could help you with modelling for the younger girls Mrs Bramlett, would you like that Teresa?” said Mrs Pugh.

“Oh yes Mummy,” said Teresa, “could I wear nice dresses like Timmy does?”

“That would be a nice help Teresa, yes you could be my second model, you would like to have company wouldn’t you Tim?” said mom.

I don’t think she expected a reply and I didn’t offer one, this was just too embarrassing, and then I thought of Teresa’s brother Tony a 14 year old tearaway, once he found out he could make my life very difficult. This was getting worse and worse.

“Right, Tim, that should do for tonight, lets get you out of that dress and then you can go and change You might as well take the things you’re wearing up to your room and keep them there until you need them again,” said mom as she removed the dress, leaving me there in my underwear.

“Oh, that’s a pretty slip, he really has dressed completely for the modelling, hasn’t he?” said Mrs Pugh, as Teresa looked wide eyed at me standing there. I thought ‘Oh no, she will tell all the neighbourhood kids about this — now I’m in real trouble.’

“Yes, to get the right fit he has to wear a bra as well and he already has panties, he likes to dress properly, don’t you Tim?” replied mom.

“Please mom, just let me go upstairs, I don’t want to talk,” I said as I rushed out of the room.

I ran upstairs and took off the slip and bra and peeled off the tights and placed them in the bottom drawer with my stupid wedding outfit, then I hung up in the slacks and blouse I’d worn today alongside Aubrey’s party dress. With that and the bridal dress and underwear which I saw mom had now hung up in my wardrobe, I now had nearly more girls clothes than boys in there. Having felt so happy earlier in the day, I now felt completely washed out and miserable, I had planned to call Aubrey and tell her about my London Coliseum appearance but just could not bring myself to call her in my present mood., I was still in Cathy’s panties, but just felt too tired to change and went straight to bed still wearing them.

Next morning I went for swimming practise. Now that was great, I always feel better after a practise session and I put up some pretty good times, I sat and had a diet coke with the other guys in the club lounge before heading home. When I reached the bottom of our road, I heard Janette call out, “Tim, over here” She was in her car.

“Tim, I need to speak to you before I go back to Bristol. I’ve picked up my things from the house, but I have also just had a major row with mom, where can we go?”

“Well now is the time I have to go to the Sunhill old folks home, I go every Sunday afternoon, how about after that?” I suggested.

“Can’t you cry off for just one day?” she asked.

“I haven’t missed for over a year now, I really wouldn’t like to let them down”

“OK then, is it all right if I come along with you?” she asked. After I nodded, she continued, “What is it you do there, tidying up the place, or what?”

“Not exactly, why don’t you come in and see for yourself,” I urged.

So we drove there and went in, as we did so the matron rushed up and gave me a kiss and ruffled my hair. I wished she wouldn’t do it every time. I introduced Janette.

The matron then said to her “Have you come to see how your little brother has stolen the hearts of everyone in the place, he is a treasure.”

“Erm…. yes”, said Janette, a bit taken aback, “That was the idea.”

I left them chatting and then started my normal afternoon. At first I just went round and visited the folk, mainly ladies, there were very few men in the home, and basically just chatted with them. I had soon learned that many of them got very few visitors and they just liked to talk. After a while I had got to remember their names and the names of their families, which they loved to talk about, so I just talked and listened while holding their hands. I let them ruffle my hair which just about everyone in this place seemed to want to do, it is something to do with having curly fair hair I guess.

Then at four o’clock they all have tea in the main conservatory room. I help with that and then I play some old sing along tunes on a keyboard and try to get them to join in. I found the keyboard covered with dust in a cupboard and managed to rig it up with some speakers I found on a skip and I learned a load of old tunes and played them while I encouraged them to join in. It was hard work at first but now just about everyone sang along or clapped in time

After this and just before I left I usually sang a solo for them. This time I played and sang my Mikado song, the one I had sung yesterday. The whole of the nursing staff came in for that and there was some really nice applause at the end.

I met Janette at the door as I said goodbye to the matron, she was wiping her eye,

“What’s the matter, Janette?” I asked.

“It must be some grit in my eye, come on we better be going,” she replied.

Back in the car, she sat, still wiping her eyes. “What is the trouble with your eyes?” I asked again.

“Its you, damn it, its you, Tim! I’m crying! Do you know what you do in there? Do you? The matron tells me that for a whole host of people in there your visit is the high point of their week, they talk about it for days after you’ve gone and then are always asking is today Sunday? Is Timmy coming?”

“Well some of them get very few visitors, so that’s sort of bound to happen” I said.

“Tim, as I was leaving, one old lady, Mrs Cavendish, you know her?” I nodded, “She grabbed hold of me and asked, ‘Are you young Timmy’s sister? I want you know if he hadn’t started coming to visit I wouldn’t be here today. I get terrible pain in my back and legs , my family haven’t visited for three years now, they are getting old as well I suppose, I was planning just to stop taking my pills and passing slowly away. Then your little brother came, he talks to me every week, bless him, we hold hands and he sings and makes us all forget how old and decrepit we are. He is a lovely boy and so talented, you must be so proud to have him as a brother’. THAT’s why I’m crying Tim.” she almost yelled this last bit at me.

She went on, before I could speak, “Tim, there are people two and three times your age who couldn’t do what you do in there, I just thought you were helping to tidy up, now it turns out you are, according to the Matron ‘the person who holds the place together’, all that and my god, you’re hardly 12 years old”

“Well it makes my next task easier,” she continued, “In some things you are mature beyond your years. There are things you need to know about your mom and your dad and you need to know right now. I’m worried for you Tim, you are going to be alone with mom after Cathy goes to college next week, you will need to be very careful and very brave.”

Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn’t understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave.

I sat with my own thoughts for a while and then I noticed we were not driving home, “Where are we heading Janette?” I asked.

“Somewhere very special Tim, - the place where I last saw your Dad” she replied

+++++++++++++++++++++++++++++++++

To be continued

+++++++++++++++++++++++++++++++++

Crossdressing with my Girlfriend and Boyfriend -4-
‘Is it wrong for me to enjoy it?’

By Cindybelle

Part 4

Janette brings Tim closer to understanding why his mom behaves so weirdly and has some news about his dad, but the embarrassing preparations for his upcoming female lead role in the musical are becoming more intense and then his mother springs an even worse surprise, maybe Aubrey can help Tim though his self doubts.

=======================
Ending of Part 3…..

Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn’t understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave.

I sat with my own thoughts for a while and then I noticed we were not driving home.

“Where are we heading Janette?” I asked.

“Somewhere very special Tim, the place where I last saw your Dad” she replied.

+++++++++++++++++

Part 4

We drove in silence until we reached a local beauty spot, Trensham Ponds, a series of small lakes in a woodland park. Leaving the car, Janette led me to one of the lakes and to a seat in an overlook. It was a beautiful place, peaceful and secluded.

“Tim, your dad brought me here seven years ago just before he left for America, he said he wanted me to understand why he was leaving, I was 15 then and he felt I should know,” Janette explained.

Mom had always led me to believe that my dad had taken off with his secretary and left us. However Janette explained that he and my mom had been estranged for years before this. Mom would have terrible mood swings and berate dad for a whole series of things, big and small, some real but most imaginary. He tried to cope with it, even tried to arrange medical help.

Mom used to call his office and leave angry messages with his secretary, which is how she got to know of his problems, She was a divorcee, and gave him help and sympathy and over time this developed into a relationship. Eventually, he was offered promotion and a transfer to the New York office. Mom said she would not go with him. About this time mom found out about his relationship with his secretary, Brenda, there was an almighty bust up which led to the separation.

“But why has he never seen us or contacted us since he left? Doesn’t he care about us anymore?” I asked. This was the big question that I could never get out of my mind.

“Mom insisted on it,” Janette explained, “Brenda had two teenage sons, if he took off with her, mom made it a condition of not contesting the divorce that she got the house and everything in it, and that he paid for our education through college, but he had no rights of access. He was not to be allowed even to contact us. That’s why our birthday and Christmas gifts come from his office.”

“So I’ll never see him, ever?” I said sadly.

“Tim, I last met your dad, here, 6 months ago!” Said Janette. “It was here, because this is where I said goodbye to him,seven years ago.”

“What! Here? How? I thought he wasn’t to contact us.” I exclaimed.

“That was until we were 21. A few days after my twenty first birthday I got a call at college from your Dad, he said he was coming over to England on a business trip and could we meet? He had traced me from my school office and they told him which university I was at.” explained Janette.

“What was he like? What did he say?” I asked eagerly.

“Tim, do you remember your Dad at all?” Janette asked in return.

“I can remember going to the park and playing on the swings and when he used to throw me up in the air and catch me. I also have this.” I said, reaching into my wallet and bringing out the small dog eared photo of him holding me when I was about four.

“How did you get this?” Janette asked, “Mom destroyed all the photos of him.”

“I found it at the back of a drawer in the desk about three years ago. I never told anyone else.” I said.

“Tim, he is very like you, even to the fair hair, he is kind, considerate and obviously very clever, he is a Vice President of the company now, and he was full of questions about you. He wanted to know everything about you, what you looked like, your hobbies, sports, your school activities. He begged me for a photograph, the only one he had of you was taken when you were four, it may even have been this same one.” She said, holding out my little photo.

“I look at it every day,” I said quietly, looking over at Janette.

“Oh heavens! That is exactly what your dad said,” exclaimed Janette in a strained voice.

I grabbed hold of Janette’s arm and said, “I must meet him Janette, I want to see him, I want to speak to my dad. My life is so messed up and confused right now and mom is only making things worse and she won’t listen to me when I try to tell her.”

“Tim, you will have to be careful, mom has sole custody, she could make it awkward for you and dad if there was contact without her permission. What do you mean about mom making things worse?”

I explained to Janette about the modelling work and being paraded in front of Mrs Pugh and her daughter and about the see through underwear I had to wear for the bridal scene in the Mikado.

“On my, this is getting worse than I realised.” said Janette, “It started with that ridiculous outfit for the wedding. I’ve just had a big argument with your mom about the wedding pictures. Mike and I decided it was unfair to have the photos of you in that outfit circulated, so we deleted, edited, or cropped them and in our thank you letters to our guests we’ve asked them to destroy any pictures of you they may have.”

“Wow, thanks Janette, but what did mom say?” I asked.

“She really lost it and accused me of making her look ridiculous in front of everyone, I told her she should have thought about that before she and Cathy dreamed up the idea and embarrassing you.” said Janette.

“ Cathy has apologised to me about that and has been much nicer to me recently,” I said.

“Well be careful Tim, just like you take after your dad, Cathy takes after mom. Now what can we do about the Mikado bridal underwear she wants you to wear? You said mom bought that at a bridal shop?”

“Yes, a place called Amelia’s in Bramfield,” I replied.

“Oh, I need to tell your dad about that, it could be important. But what can we do now about those Mikado clothes?” she said.

“I think I might know how to get round that” I said, explaining about the outfit that Miriam Jenkins wore at the Opera, my singing there for her, and that I thought that she and I could explain to Mrs Cartwright my drama teacher that a simpler outfit would be more suitable.

“You continue to surprise me Tim, you sang at the Coliseum and now you have Miriam Jenkins coming out to your school to see you! That’s amazing. Well, let’s see if that works. But we need to have a plan to help you if mom gets worse.” Said Janette.

“Here’s what we should do,” she continued, “Although dad can’t contact you, there is nothing to stop you writing to him, I’ll give you his address and then, if and when you want to, you can tell him about yourself and your problems. If he wants to reply he can send it via me and I’ll make sure it gets to you without mom knowing. She mustn’t know anything about this Tim.”

“And now I am also going to give you some money which you must keep hidden. You must promise me that if things get too tough you will use it to come and join me and Mike in Bristol.”

With that Janette handed me  £100 and wrote out my dad’s address and her new address. It was the most money I had had in my life. I looked at the address, - John Bramlett in a place called Manhasset in Long Island, I felt closer to my dad just looking at it. I folded it and put it in my wallet next to my photo of him.

“Tim, I need to start back for Bristol now, I’ll drop you off near home.” She turned to me and held out her arms, “Are you too big a boy to give your sister a hug?”

In answer, I put my arms around her and huddled in close to her. “I really can’t thank you enough, Janette. I was getting desperate, I have so many problems, but with the news about my dad they don’t seem so important anymore. I must meet him though.”

“Don’t worry Tim, after what I’ve learned about you today I will make sure you meet him.” Said Janette.

With that we walked back to the car. Later, when she dropped me off, I said my goodbyes to Janette and then I walked back home deep in thought. I was already composing the letter to my father.

“Where have you been?” shouted mom as I walked in , “ You’re normally back from that old folks home ages before this. If you are going to take this long I will have to stop you going there, I don’t know why you bother anyway, they are just a load of old has beens. Well, while you’ve been doing that I’ve been working all day and I need your help, so upstairs and get into your dress modelling underwear I need to finish off your dresses tonight.”

I went resignedly upstairs. Now was not the time to pick an argument I reasoned. I now had the chance of meeting my dad, this had become the most important thing in my life. So I felt strangely detached as I removed all my clothes and slowly put on the panties and bra and rolled up my tights, I was getting quite used to this now I thought as I put on the slip.

When I had finished I walked over and looked at myself in front of the full length mirror, for some reason I thought of Jason seeing me like this. With the excitement over the news about my dad I had not discussed my involvement with Jason with Janette as I had intended. Then again I wondered if I ever should or ever could talk with her about that kind of thing.

Of course there was talk about boy to boy relationships at school, but that’s all it was, young boys talking. Just like they talked about girls, at first with some disdain, then in time with rising curiosity and then with a growing interest. I imagined Jason approaching me and holding me as he had at Bramfield station and moving to kiss me. Somehow this thought aroused me and on an impulse, or was it an instinct, I walked over to the wardrobe and took out Aubrey’s handbag, the one I brought with me on the train after the swim meet, and pulled out the lipstick and slowly moved it over my lips. Looking at myself I became more aroused and pulled out the mascara and blusher and I somewhat inexpertly applied them. Remembering how Jason reacted when he saw me in Aubrey’s dress at the wedding I wondered what he would do if he saw me now, maybe he would…. And then the phone rang.

My mom shouted up the stairs “It’s for you, its Aubrey, use the extension up in my bedroom and hurry up,”

I shouted OK, and waited until she had gone back into the lounge and dashed across to her room and picked up the phone.

“Tim, Jason’s just told me about what happened at the Coliseum, you really met Miriam Jenkins and you sang on the stage?” she said excitedly, “Why didn’t you call me to tell me about it.”

Suddenly I felt awful, dressed and made up as I was and talking with Aubrey, it seemed wrong and I was ashamed. I stuttered out a reply.

“Oh, sorry Aubrey, I really meant to, after I got back from London mom had me dress modelling again and I was just too tired after that, today I’ve been on the go all the time, swimming all morning , then on to the Old folks home and I’ve just got back in after saying goodbye to Janette.”

“Are you all right Tim, you sound short of breath?” she replied.

“Yes, I’m fine. Its just been a bit of a tiring time I guess, the opera and saying goodbye to Janette were sort of emotional moments as well.” now rushing, I said “Look Aubrey, mom wants me downstairs now, I must go. I really want to talk to you, please say you’ll come next Saturday, there is so much I need to tell you.”

“Hey, calm down Tim, of course I’m coming, don’t worry. What am I saying, you’ve got me worried now. Are you sure you’re all right?” she said.

Then mom walked in and saw me sitting on her bed and had obviously noticed I was wearing makeup. She signalled to me to get off the phone. I said a quick goodbye to Aubrey, trying at the same time to think of an explanation for my mom.

“Well, don’t you look pretty, did you want to look nice if Teresa and her mother come round?” she said looking closely at me.

“No mom, I guess I felt that as you want me to model girl clothes all the time I might as well look like a girl.” I replied, it didn’t sound convincing to me nor by her look did it to mom.

“If that’s what you want, then lets do it every time. I’ll get you a full make up kit and you can learn how to do a proper job. Well, its good that you’ve done this as I bought your wig today for the Mikado and I’ve finished the wedding dress so let’s go and try them on first,” mom ordered.” Don’t forget your white bridal shoes.”

I retrieved the shoes and came slowly downstairs. Mom placed a wig cap on my hair and then arranged a long black wig on my head and proceeded to style it, Japanese style, in a series of elaborate curls and buns held in place by large stick like pins. It felt heavy on my head.

“Now for the dress, be very careful as you step into it, I will only be able to do up the back velcro straps part of the way because you are not wearing the corset which brings your figure in a shade more. But it will do for now.” she said.

It really is difficult getting into a dress with layers of inbuilt petticoat swaying around and oh my, I thought, I’ve got to do all this on stage in Act 2. I felt mom tighten up the back fastening and realised once I’m in this dress there is no way I could get out of it without someone else’s help, I was trapped in it.

“There, how does that feel?” asked mom as she finished.

I walked over to the mirror. The dress was made of what I later learned was white taffeta overlain with silk organza lace frills in a series of scooped layers round the very full skirt, it was shaped around the bust and had what are called three quarter length sleeves in the silk organza, which looked transparent. Now I had the wig on and was wearing makeup the effect was shattering, there was no sign of Tim left.

“Mom, I don’t think I can do this. The dress is heavy, it’s uncomfortable and I would have to wear it for over an hour, most of the time on stage while I’m trying to sing and act, its too much. For the Dorothy part it was just a simple dress, I still wore my own underwear as well.” I was about to go on, but mom interrupted.

“Is that the thanks I get!” shouted mom. “Don’t forget you were specially chosen for the role and I have spent about 15 hours making the dress so you would look the part and all you can say is it is uncomfortable and heavy.”

She went on, “You saw the Mikado on Saturday, didn’t seeing the opera played like that inspire you want to try and do your best for your school? What was it like, what did you see?”

Then I remembered although I had wanted to tell her when I got home, she had accused me of being late and wanted me to model for her as soon as I got in. So I told her about the opera and meeting Miriam and singing for her.

“You mean that you sang on the Coliseum stage and Miriam Jenkins is coming to your school to help and to see the show, and you don’t want to do the role! Oh no Tim, she is going to see you and she is going to see my dressmaking as well you can be sure of that. This is so exciting! I must have Mrs Pugh come round to see you and you can tell her about it.” so saying mom headed for the phone.

“Mom, no, no, please. I’ve had enough for today. I was up early and did 3 hours swimming then I went round to Sunhill until 5 o’clock and then” I nearly said I met Janette, but stopped myself in time, “ and then I want for a walk until I came back home now. I’m really tired.”

“I suppose it is a school day tomorrow and you have rehearsals afterwards don’t you? When do the dress rehearsals start? Asked mom.

“I don’t know mom I’ll ask Mrs Cartwright tomorrow” I replied.

“All right then, let me take the dress off you and remove the wig, then you can get ready for bed, we can show you off to Mrs Pugh and her daughter later this week” she threatened.

When she had taken them off she handed me the dress and the wig and told me to take them up to Janette’s old bedroom as I would be moving into there during the week.

I trudged upstairs and walked into Janette’s room. It still smelt of her perfume and scent. I looked at the pink and white décor and the frilly curtains and bedspreads and groaned. I caught sight of myself in her mirror and with a jolt I noticed that with the clothes and makeup I was wearing I almost looked like Janette.

I ran into the bathroom, almost tore off the underwear and showered for nearly twenty minutes trying to wash the make up off and become Tim again.

Then I went back to my room, I put the little photo from my wallet on the desk and started to write a letter. A letter to my dad.

The next morning I hid the money Janette had given me and the letter I had started to write to my Dad. There was so much I wanted to say and wanted to ask that I was finding it very difficult to write, especially has I never spoken properly with him.

At school I found it difficult to concentrate and was revived when school lessons finished and I went along to the rehearsal room for the cast of the Mikado. I was there first and greeted Mrs Cartwright.

“I’ve now seen the Mikado onstage. I went to the London Coliseum last Saturday, Mrs Cartwright, it was brilliant! I even had a chance to sing on the stage myself.” I had been bursting to tell her this.

“Tim, what on earth are you talking about? How could that happen?” she exclaimed.

I told her the whole story and when I mentioned that Miriam Jenkins was planning to get in touch and help and wanted to see the show she got really excited. By this time the other members of the cast were arriving, so I had to go through the story again.

I suppose it’s fair to say that a number of the boys who had been pressed into playing roles, especially the female roles, had been less than enthusiastic, but the thought of having a real opera star come to rehearsals really stirred everyone up. So things went really well after this and at the end of the evening they were all asking me questions about the London production and the Opera House.

I hung around until everyone had gone so I could get a chance to talk to Mrs Cartwright alone.

“Could I talk with you about the costumes for the show Mrs Cartwright? Having seen the Coliseum production I wanted your views on what my mom is planning for our production.”

“Of course Tim, is there a problem?” she asked.

I explained about the transparent peignoir and corset garment that mom had bought at Amelia’s and the more sedate costumes the Miriam wore at the Coliseum.

“You mean your mother had these garments especially made? Mrs Cartwright queried.

“Yes, she said you had a grant to cover the purchase and could use the garments again,” I explained.

“Oh, the money I have is to cover the purchase of material only , the idea is your mom and the other moms help make up the costumes, we don’t have that much money we can afford to buy made to measure garments like you describe Tim. Plus they are unlikely to fit anyone else.” Mrs Cartwright said. “Don’t worry Tim, I will speak with your mother and sort things out. I agree that the kind of outfit you describe would hardly be appropriate for a school production”

Much relieved, I said “Thanks, Mrs Cartwright. It really has been worrying me. Having sung for Miriam I am feeling more confident now that I can do the role but I do not want to have the extra worry about the costume”

I felt better after that and on getting home found mom did not need me that night for dress modelling, so I went up to my room, finished some homework and resumed composing the letter to my dad.

On Thursday when I got home from school I received a shock. On going up to my room I found it was now full of mom’s dressmaking equipment, even the bed had gone. Fearing the worst I went along to Janette’s old bedroom and sure enough all my kit, my swimming trophies and toys and clothes had been moved in there. I looked in the wardrobes and saw my few clothes and all the dresses and underwear had also been moved as had Cathy’s clothes from her old wardrobe.

I looked around the room. The walls were painted pink with white outlining, there were white lace curtains and the bed had shiny pink satin sheets with lace lined pillows, there were pictures of fairies and ballerinas on the walls, but no shelves to put my trophies or room to hang my posters. This was to be my room.

Mom came in at this point. “Ah I see you’ve come into your new room, as you see it’s much bigger than your old room and I know I can trust you to keep it nice and tidy,” she said.

“But mom it’s like a girls room. Can’t we redecorate it, so I can put up my posters and have some shelves for my trophies?” I asked,

“Tim your need to remember that money is short and now your sisters are grown up we may soon need to move to a smaller house, so I don’t want to redecorate another room as a teenage boys room, it wouldn’t help to sell the house.” Said mom.

Both these bits of news depressed me, I felt utterly defeated by the way mom was treating me. My only hope now was that my dad may be able to help.

“Oh yes,” said mom, “ Mrs Cartwright called today while I was out and said she wanted to talk with me when I came round with some dresses for the Mikado cast tomorrow, she said it was to do with your part. Do you know what this is about?”

I decided to duck this one. I knew mom would be mad when she found that I had told Mrs Cartwright about the purchase of the underwear, but I couldn’t face telling her myself even though I knew I would be in trouble. “I don’t know what it could be mom,” I replied.

Friday, when I got home from school mom descended on me straight away.

“ First Janette makes me look ridiculous in front of everyone with her attitude to your wedding photos and now you’ve been telling tales to Mrs Cartwright about my buying underwear for your role. She said she had talked to Miriam Jenkins about it and she said she thought it inappropriate for the role. So now you’ve made me look silly as well. I hope you are proud of yourself, you are becoming more and more like your father,” she shouted at me.

“But mom, it’s just that I saw how Miriam was dressed playing the role and it looked so much better.” I said.

“Better eh. Well you will be pleased to know I agreed that the peignoir should not be used, but as your wedding dress is tailored to fit you when you are wearing the corset, then that will have to stay. Oh, yes, and when you go up to your room you will find the makeup kit I promised you after your attempts earlier this week. You had better start practising because I have another nice surprise for you.” She said.

“Surprise, what surprise mom?” I asked

“ I have decided to have some photographs taken of my dresses to use as advertising and in a catalogue, Amelia is helping me as she does a lot of this herself with her wedding dress business. She is coming around here tomorrow morning to help take the pictures, so I want you to model the dresses for me, Teresa is coming around as well.” Said mom.

“But, mom, do I have to? Aubrey is coming here in the morning and then she is going with me to the swimming competition at school in the afternoon,” I said urgently.

“All right then, she is a pretty girl, if Aubrey helps model as well we should finish in time so you both go to the swimming,” mom said.” You had better see if that is OK with her”

I went upstairs and called Aubrey.

“You may not want to come now Aubrey,” I said, “Mom wants to make a catalogue of photos of her dresses and she wants you to help model them tomorrow morning if you come” I said wanting to put her off..

“But it sounds fun. Who else is modelling?” she asked.

“Just me and Teresa a nine year old from next door,” I replied.

“You mean your mom wants you to model for a catalogue of girls dresses, that’s really weird Tim”. She said.

“You think I don’t know that. It gets worse, she has just bought a whole host of makeup for me to use.” I replied.

“Tim, I am definitely coming. I want to see you and you said you had things to tell me didn’t you?”

“Yes, Aubrey, but its going to be awful, with mom in one of her weird moods and it’s all so difficult and embarrassing for me as well.” I said.

“We’ll get away as soon as we can and have that talk. I really want to help you Tim.” said Aubrey in reply.

“Thanks Aubrey I don’t know how I’d get by without you, thanks so much, I’ll see you tomorrow.”

With that we said goodnight and I tried to return to writing my letter to dad. I was on my third draft but I could still not find the right words for what I wanted to say.

I was usually first up on Saturday mornings, but this morning mom put her head round my door and said “Time to get up Tim. Amelia is here and its time to start getting you ready. After your shower just put on your bra, panties and a slip and the housecoat I gave you and come down for breakfast.”

This is going to be a terrible day, I thought as I slowly showered. Aubrey and young Teresa are going to be here as well, while I am parading around in mom’s dresses.

Amelia was at the breakfast table when I got downstairs, “Well here’s our beautiful model, good morning Tim, you look fetching in that housecoat. You are a good boy to help your mother with the catalogue.” she said.

I just said good morning and sat down with my breakfast, trying as I do on these occasions to tune out and think of something else. So I concentrated on today’s swimming session and my tactics for the races I was in.

When I had finished breakfast, mom said, “It’s time to go up to my bedroom and Amelia will put on your makeup for the photographs.”

“Is that necessary mom?” I queried, “I thought it was a catalogue of dresses.”

“It will be photographs of pretty girls wearing the dresses with you, Teresa and Aubrey doing the modelling, You don’t want to look like a boy wearing a dress in the catalogue do you?” said mom.

“I guess not mom,” I said as I walked resignedly upstairs.

Once upstairs, Amelia had me sit at mom’s dresser where she started to do a thorough job of applying my makeup, she spent a lot of time on my eyes, shaping my lashes and applying mascara, eye liner, eye shadow and pencil to outline the fair hair on my eyebrows.

“The eyes are important Tim,” she said, “With the right emphasis on your lovely wide eyes the rest is easy, you have a nicely shaped face, just a little emphasis on your cheek bones, here and here and now just a hint of lipstick and gloss on your lips and you will be perfect.”

“Next, we want you wear this wig today Tim,” said Amelia, holding out a blonde wig, it was long, below shoulder length and fell in a cascade of loose curls.

She placed a wig cap on my head first and then placed and adjusted the wig. I had never worn hair this long and found it strange to feel the hair resting on my shoulders and hanging down my back as I sat in the slip. I looked in the mirror at my fully made up face, now crowned by this mass of blonde tresses. I unconsciously moved to brush the hair out of the corner of my face and noticed how feminine this looked, a gesture I had seen girls do so many times as they preened themselves. Again I felt a strange tingle as I looked at myself.

At this point there was a knock on the front door. It was Aubrey. I heard my mom telling her to come upstairs where she would find me.

She walked in as I turned around, she stopped dead in her tracks.

“Is that you Tim? Oh my god you look awesome. So you are going to model for the catalogue then?” she said.

“I wasn’t given any option Aubrey, mom wants me to do it This by the way is Amelia her friend.” I explained.

“Yes Aubrey, and I understand you want to help as well. Let’s see if we can make you as beautiful as Tim,” said Amelia, “We’ve put all the dresses in Cathy’s old room Tim, you go in there now and your mother will help you into your first dress.”

So I said see you later to Aubrey and went into Cathy’s room and found my mom putting a little girls party dress onto Teresa.

“Why can’t I wear make up and have long hair like Timmy, I want to look like Timmy, “ Teresa cried out.

“Now, now Teresa, you will have to wait until you’re a big girl, stand still while I adjust this dress.”

“It’s not fair, Timmy’s not even a real girl and he gets to wear pretty underwear and make up and things.”

Shut up, you little brat I thought, this is bad enough without you going on about pretty underwear. This is going to be a long morning.

“Tim you put on that pink and green floral sun dress on the rail over there, be careful it has a flounce down the side which is meant to hang loose,” said mom.

I put on the dress and stood waiting until after a while Aubrey came into the room now fully made up, her beautiful hair did not need any further attention. Then mom made her take off her skirt and top, this in front of me, and put on a light green satin formal dress. Aubrey was only wearing a bra and panties so both she and I were embarrassed, I turned away. Again, I felt mom was getting way out of hand in this business.

“Come downstairs when you are all ready” said mom, and left us in the room.

“I’m sorry Aubrey to let you in for this, mom is out of control when she gets into one of these moods,” I said.

“Don’t worry Tim, I’ll see you through this. She can’t go on like this. Let’s just get this over with now and then we will plan what to do. Here let me adjust your dress, your bra strap is showing. I have to say though Tim you do look very good in that dress and your hair is wonderful,” said Aubrey trying to cheer me up.

We went downstairs where photos were taken by Amelia of the three of us, sometimes together, sometimes separately in front of a cloth background they had rigged up in the lounge, also there were some shots taken in the garden. We each wore four different dresses, each time changing in the same room. By the end I felt I really was a dress model, I couldn’t help noticing how I looked as I saw myself in Cathy’s full length mirror, there was no indication of Tim the boy, I looked like a teenage girl.

At the end I took Aubrey into my room to start to take off the clothes.

Aubrey looked around, astonished, “Is this really your room Tim? It looks like a girls room, why are your trophies on the floor?”

“It used to be Janette’s, mom has taken over my room for dressmaking and she won’t let me change it. Just wait here Aubrey while I go for a shower and get rid of this make up and stuff, I want us out of here.” I hurriedly said.

When I got back, showered and changed, Aubrey was standing looking puzzled.

“Tim, I hope you don’t mind, but as the doors were open, I looked in your wardrobes, all you’ve got is two school uniforms, four pairs of jeans and half a dozen T shirts and sweaters. Half of those are girls fit as well. The rest is all girl’s clothes in this wardrobe.” she said.

I explained again that money was tight and that I had often had to wear Cathy’s cast offs, and now had all the clothes she left behind when she went to college.

“Tim, this is just not right. For a start, Jason has a lot of clothes he never wears and I am going to get him to give them to you, his older stuff should fit you anyway,” Aubrey urged.

“And another thing Tim,” Aubrey continued, “What is this dress doing here in your wardrobe, it looks like a wedding dress?”

“It’s my dress for the Mikado.” I explained.

Aubrey removed it and held it up, “But it’s so elaborate, I mean it’s beautiful, but it’s better than some real wedding dresses I’ve seen and you will only be wearing it for two shows won’t you?”

“Yes, but for the whole of the second act, its really heavy and uncomfortable and I have to wear the corset underneath which is even worse.” I said.

“Our costumes are nowhere near as elaborate as this and a corset as well!, “This is incredible Tim and your mom wants you to wear all this as well? Said Aubrey.

“Its entirely mom’s idea, our drama teacher has already had an argument with her about what I wear when I come on stage before I put on the wedding dress and has asked her to tone it down.” I replied.

“Well I think that’s right. I really must come to your show, can you get me a ticket? Asked Aubrey.

“I’m scared enough already, but if you really want to come I’m sure I can get you a good seat, but you must promise not to laugh.” I said.

“Tim, I’ve already heard you sing don’t forget, You have a better voice than Felicity Chapman who is our Yum Yum and she isn’t a great actress either, nor has she appeared at the London Coliseum!” joked Aubrey, “No, Tim, I know you’ll be great in the role, I want to be there to cheer and applaud.”

“Its just having to dress up so much scares me. It’s weird, when mom tried the whole costume on me with the wig, makeup and everything and I looked at myself in the mirror, I was stunned when I saw how much like a girl I looked. Part of me was pleased I could do it so well, so convincingly, then I feel sort of ashamed that I’m enjoying it. Is it wrong of me to enjoy dressing up? I asked.

“Tim, you have to remember you are acting out a role.” said Aubrey, “To make it work properly you have to look like a girl, not like a boy in a girl’s dress, and no I can see how any real actor would be pleased if he could transform himself like you can, its nothing to be ashamed of. Look, I know you are also a first class athlete and that you can beat boys two years older than you are. If you have a problem it’s that you’re just too good at everything you try to do, the only thing you have to worry about is other people being jealous of you”

“That’s funny, that’s exactly what Cathy said to me, that she was jealous of me” I replied.

“Well, if it helps, I’m not jealous of you, I just happen to think you are the nicest boy I’ve ever met. Hey, shouldn’t we be heading for your school and the swimming competition?” Said Aubrey.

In answer I said, “Not before I hug the nicest girl I’ve ever met and Aubrey, thanks so much for saying that about acting out a role, that’s helped me a lot.”

Then we both got changed and ready, I picked up my sports bag and we cycled off to my school, Aubrey had borrowed Cathy’s old bike. When we arrived I took her over to the spectators area where there were just a handful of people, a few parents and some of the boys from school.

“I’m afraid there aren’t as many people here as at the Leisure Centre last week, do you mind?” I asked Aubrey.

“No Tim, in fact you can call me kinky if you want, but I rather like looking at a bunch of athletic guys in skimpy swimming briefs, one guy in particular however,” she said reaching for my hand, “Have I ever told you that you look really cute in those little speedos.”

“You know how to make a guy feel embarrassed, don’t you?” I said, reddening, “But that’s really nice to hear after this morning’s horrors. Thanks, I love you for that” As I said this I realised I had used the ‘love’ word, we had never said that to each other before.

Aubrey was now looking at me, her mouth slightly open and seizing the moment I moved forward, heedless of the people around and kissed her straight on the lips, turned and walked quickly into the changing room.

In the room, after I undressed, I had another shock. I noticed that the impressions of the bra straps could still be seen on my skin, I quickly draped a towel around my shoulders and sat like that while I waited my turn.

When it came to my races I was really wound up after the tension of the morning and my feelings for Aubrey, such that when I hit in the water, I raced flat out the whole way in both of them. Normally you pace yourself in relation to the other swimmers and try to leave a reserve for a strong tactical finish. This time I just swam hard paying no attention, just determined to swim the opposition into oblivion. I set up my best times ever and won both races and the second race was the one that won the competition for the school, so I felt elated and ran over to Aubrey and hugged her.

“That was brilliant, Tim, but next time can you dry yourself off first!” she said. However she hugged me back just as tightly. “Thanks for coming straight over though, I love you for that too, now you had better go back, I think your team mates want to congratulate you as well.”

I was really making a spectacle of myself, I realised and I took an amount of joshing from the rest of the guys in the team as I walked back over to them.

However the team captain came up and said to me “Tim, it was your last race that won the competition for the school, I want you to go up and collect the cup on behalf of the team, that’s if you can tear yourself away from your girlfriend,” as he slapped me on the back. Seb. Johnston was seventeen and a County champion as well as our Team captain so I was taken aback by his request, but he pushed me forward.

As I stepped forward to accept the cup I had a thought. If only my Dad was here to see me, as well as Aubrey, that would make up for all the trouble and torment I’m going through at home. Well, soon maybe, but I must finish that letter to him, the letter I was finding so difficult to write.

After I had changed I said to Aubrey, “Lets get some snacks and a drink from the shop at the corner then I want to take you somewhere for a picnic and our chat.”

We cycled off to Trensham Ponds and the same secluded overlook that Janette had taken me to.

“This is a lovely spot Tim, but why here, now?” asked Aubrey.

I told her all the news that Janette had given me about my dad and how he and mom broke up, when I mentioned the link with Amelia which Janette had noted, Aubrey immediately picked up on it.

“Tim, how long has your mom known Amelia? Aubrey queried.

“Not long I think. When I went to get fitted for the corset and stuff she greeted mom as if she had only spoken on the phone before” I replied.

“That can’t be right Tim, this morning I overheard her talk to your mom about having met your dad and an argument they had had and that you and Cathy were in the room at the time, that must be over seven years ago. Why should she lie? Were there other people in the room at the dress shop?” said Aubrey.

“Oh yes there were two other assistants. Do you think mom and Amelia were covering up for them and me about knowing each other? Why would they do that?” I asked puzzled.

“Tim, I don’t want to alarm you and I may be completely wrong, but I thought that your mom and Amelia were being more than just familiar and helpful to each other, I think they are really good friends, very close friends, if you understand?” said Aubrey.

“And you think that has something to do with how mom treats me, but how, why?” I asked.

“I think the only people who can answer that are your dad or maybe Janette,” said Aubrey, “Perhaps you could ask your dad? Have you written to him yet?”

“No I can’t figure out what to tell him and ask him. I don’t want to put him off by going on and on about my problems,” I replied.

“What do you really want to say?” she asked.

“That I miss him and I want to see him and talk with him, I want him to see me swimming, I want him to meet you,….” I said, but Aubrey interrupted..

“Why don’t you just write that and nothing more, you can leave all the talking and explaining for when he comes to see you. Tim, if he really wants to see you again that should be enough.”

“Yes maybe you’re right, I was trying to cover everything up front, I didn’t want to mislead him or risk that he would be disappointed in me.” I explained.

“Tim, I really could grab hold of you and shake you at times.” Said Aubrey earnestly, “The last thing any father of yours would be, is disappointed in you. Just write the letter, once he meets you and gets to know you he will be prouder than anyone, apart from me, that is.”

With that she grabbed me in a giant hug and I responded and held her tightly. We sat on the seat overlooking the lake until it was almost dark, sometimes we spoke but mostly we just cradled each other and started gently touching each other. I had never felt so close to anyone until that moment.

We rode home in the gathering darkness. Mom actually made us supper, even asked about the swimming. I let Aubrey tell her as she seemed to be getting on well with mom who had thanked her for helping with the catalogue photographs.

Afterwards as I walked with Aubrey to the station she asked me, “Tim, have you called Jason recently and fixed up meeting with him again? He was really impressed with the way you wowed them at the Opera and I think you both enjoyed the visit to the Bramfield Arena. Please call him and keep in touch, I think he’d appreciate that.”

“Well I am rather busy, with rehearsals, swimming and schoolwork, but yes Aubrey, if you want me to, I’ll call him. I feel bad about not being able to pay my way though, that’s why I haven’t been in touch, ” I replied.

We said our goodbyes at the station promising to meet if we could the next weekend, then I walked home, up to my room and started writing the letter to my dad. I vowed I would finish it that night. I still have the copy of the first draft I wrote, before writing a final neat version.

“ Dear Dad,

I hope you don’t mind me calling you “dad”, I’ve always thought of you that way rather than “father.” I can remember you from when I was 3 or 4, when you took me to the park and we kicked a ball around and played on the swings. I still go down to that playground and look at the one photo I have of us both together, I think it was taken in the park, you are holding me up on your shoulders and look as if you are shouting something. Janette told me you have a photo of me, is it the same one?

Janette said she had told you about what my hobbies and school activities are so I won’t repeat that here. Today I swam in a competition at my school and won both my races, I wished you could have been there. I really would like to meet you next time you visit England if you have time. There are so many things happening in my life I want you know about. I tried writing about them but when I wrote it down, it all seemed so trivial, I think its better if we could just talk about things. That’s what my girlfriend thinks as well, she told me not to worry, just keep my letter short.

There is so much more I want to tell you, but I will just say that I still remember you, I really want to meet you and talk with you and share my life, the nice things and the worries.

I need you dad, please come if you can.

Your loving son,

Timothy

I put it in an envelope and carefully addressed it and took it to the post box at the end of the road. Now it was on its way I felt a sense of elation, but also I thought about what Janette had told me about the conditions of the divorce. Could he really make contact with me and what would it do with the agreement with my mom? Then I was overtaken by another series of worries. Would it make my mom’s attitude even worse?

Then there was Aubrey, asking me to keep seeing Jason. If I was honest, part of me wanted to, but I was aware we were touching another area that gave me both pleasure and worry. There was a lot we had in common that made for a good friendship. But Jason’s feelings for me had another aspect to them, an aspect I felt as well, but did not fully understand.

One way and another I knew things would have to come to a head, between me and Aubrey and Jason, and just as importantly between me, my mom and my dad. I was beginning to realise that the next few weeks could set the course for the rest of my life, the thought filled me with both dread and anticipation.

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To be continued

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