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.

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To be continued

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