The Male Debutantes' Pageant

by Annabel Naismith

 

Chapter Three

Next morning the queue at the bus stop was full of chattering about the plans for making over the boys who were to make up the stars of the debutantes' beauty pageant. Karen, her friend Susie and Susie's younger sister Amy were also discusing the revelation that Karen's father had dressed as a girl in three Gilbert and Sullivan operettas when he was in his early teens at a boys only school.

"I still think it's a bit weird, making the boys dress as girls. There must have been a girls school nearby," Karen was saying.

"And I still can't believe he was actually singing 'we are dainty little fairies' when that bloke walked past. It was so funny. He stopped singing and said good evening to him. I thought Amy was going to die." said Susie.

"Yeah and mum loved it when we told her," added Amy. "Your dad was so funny, my sides were really hurting."

"Well it got better when he got back home, mum greeted dad with somthing like 'you never told me you were a fairy'. Poor dad had no idea what mum was on about. I think he thought she meant she was thinking he was gay."

Karen continued, "I still can't believe the way you just told him about the pageant, Amy. I'm really glad you did, though, because now they know what's happening and mum is going to help us get Andy ready. She was really upset with dad though, she made him go and sit in the living room while we told her all about Andy and then she went in to talk to him after we went to bed. But they didn't seem to be having a fight or anything." Karen's flow was interupted by the arrival of the bus to take them the 6 miles or so to high school in the small town of Haywards Heath.

Meeting other school friends meant that detailed planning of the stages Andy was going to have to go through would have to wait until after school, when it was agreed that Susie and Amy would come to Karen and Andy's house for something to eat and to make a start on Andy. Andy was not asked for his opinion on this early start to his transformation; he was quietly hoping that he would wear a skirt and some make-up for a couple of hours at the end of June. That would be in several weeks time; now it was still the middle of May. Nothing to worry about, just let his hair grow a bit and maybe the girls would want to file and put clear nail varnish on his fingernails. The nail varnish would be removed a couple of hours later, no problem.

When Andy arrived home at 4:15 that afternoon, Andy did not have to contend his sister and the two girls from along the lane but, much more worryingly, his mother. His mother was quite a forceful personality and when she had a plan about something, she made sure it happened.

"Hi mum," Andy greeted his mother, as he entered the house.

"Hello Andy," she greeted him, "I'm glad you're home on time this evening. I have made an appointment with the hairdresser in the village to trim your hair a bit at five o'clock, just to make sure it will grow out into something sensible for this pageant."

"But mum! The pageant is not for weeks," complained Andy.

"I know - and how long will it take your hair to grow? I have told her just to give it a trim and a tidy-up. I don't expect her to put curls in your hair or anything girly this evening. She is just going to style it so it is presentable as a girl. If and when the girls decide to style it, you can go out with them."

"You didn't tell her I was going to have to be a girl did you?"

"Well yes, I had to didn't I? If you're going to do this pageant, you're going to do it properly. And now you've made a commitment to the girls, I expect you to see it through. Now go upstairs, get changed and start your homework."

Andy gloomily went upstairs to change into his jeans and sweatshirt.

A half hour or so later his mother called him to say that it was time to go to the hairdressers. Andy walked the half mile or so feeling like a prisoner on death row. If she is working to mum's instructions, what the hell am I going to look like? he asked himself. A few minutes later, he entered the small old fashioned shop, with a hairdressing salon in the front room.

"Hi Andy," said Tracey the hair stylist with a friendly smile. "I' ve been looking forward to doing you."

Andy acknowledged her greeting shyly and sat in the chair, resigned to his fate. Tracey washed and conditioned Andy's hair and snipped it carefully with her scissors, chattering merrily all the time about how much fun it was going to be dressing as a girl and how she wished she could be there on the evening to see all the lovely debutantes. Andy was wondering how he was going to escape the embarrassment of the next few weeks. He could run away but he had nowhere to live. There was always suicide but that seemed a bit drastic. Andy suddenly realised that all was not well. Something unusual was happening, something that had never happened before. There was a pungent smell and his hair was being wrapped in strips of silver foil. He looked in the mirror.

"What are you doing with those bits of foil?" he asked Tracey.

"Oh just some highlights. Your mum said they would help your look."

"What are highlights?" asked Andy.

"They just colour a few strands of hair, so they have a slightly lighter colour than the rest of your hair. When I take them off you'll see how natural they look. I think you'll like them. Don't worry the colour will complement your natural hair colouring. Now I need to leave those in for a few minutes. Would you like a cup of tea?"

Andy shook his head to decline the offer of tea and Tracey went into the back of her shop to boil the kettle. What seemed like an eternity to Andy later, she returned.

"OK, then, let's have a look shall we," said Tracey and she started to remove the strips of foil. Andy was intrigued. The strands of hair which had been dyed were ligher than his natural colour but subtly so. He was pleasantly surprised by the effect.

"Uhh, that doesn't look too bad," he enthused.

"I thought you'd like it. I was under instructions not to do anything drastic. Now I just need to blow dry your hair and then we're done." Tracey got a brush and and her hair drier and went to work. A few minutes later she was finished.

"Thank you," said Andy as he rose from the seat.

"Your mum paid when she came in earlier," said Tracey, "thank you Andy. Good luck with the girls, don't let them bully you too much and I hope to see you soon."

Andy felt a bit more cheerful on the walk home. His hair was softer and more fluffy as it was disturbed by the breeze on the mild spring evening. When he got home it was just after six o'clock and dinner was on the table. Not only were Karen and his mother there but so were Susie and Amy,

"I do like your hair," said Karen.

"Cool, you've got highlights," said Amy.

"Turn round, let's see the back." said Susie.

Andy had never had such a fuss made - it was only a haircut for goodness sake. He dutifully turned round.

"Oh wow, it even curls a bit," said Amy, "that's really nice. I do like that. I might get mine done like that."

A wave of panic hit Andy. "It doesn't look girly does it?"

"Of course not Andy," said his mother. "It really suits you and it will grow out a bit so in a few weeks it will be something for the girls to work with. I must say Tracey chose a very subtle shade for the highlights. No boy will notice that your hair is a different colour from usual. That is just the effect I wanted."

After dinner the girls started their plans for Andy's make-over began in earnest.

Karen started on his fingernails, filing each one from the outside to the middle to make an oval shape. She was unable to file very much because they short and one or two were broken. Then she applied two coats of clear nail varnish to strengthen them and make them less likely to split. Meanwhile Susie and Amy were discussing whether Mandy should wear a dress or a skirt and top.

"I think Mandy should wear a dress. Girls always look dressier in a dress. A skirt and top is too ordinary," said Susie.

"Yes, but will the dress hang right. She does have boy's shoulders," said Amy thoughtfully.

Andy was not at all happy to be referred to as 'Mandy' and 'she'.

"Well, we can try both and see which looks better," said Susie. "Karen do you have some old clothes so we can try out different looks?"

"Well yes come into my room and we'll see what we can find," said Karen and the 3 girls rushed upstairs.

Andy was left in the living room wondering what humiliation the next few minutes were going to bring. His mother returned, having cleared up after dinner.

"Where are the girls, Andy?" she asked.

"They've gone upstairs to find some clothes for me."

"They don't waste time do they. Are they going to dress you now?" his mother asked.

"Yes, I think so."

"Right, well before they start, you need your own underwear. You can't share Karen's things. I got some things when I went shopping today. Go to your room and put these on." She handed Andy a bag which Andy dutifully took and went upstairs to his room. He was worried to hear the sounds of girlish chatter and giggling from his sister's room.

He went into his room and undressed. Then he looked in the bag. There was a packet of girl's plain cotton panties, some plain white bras, a plain white skirt-like garment with an elasticated waist and lacy bit at the hem, a packet of tights and some strange shaped things that were soft and flexible to the touch. Nervously he put on a pair of panties and pulled them up his legs. They fitted snugly and were quite comfortable. His confidence grew - maybe this would not be too bad after all. He picked up a bra and worked out where his arms needed to go. He put his arms through the holes and reached behind him to do up the clips at the back. Something didn't seem right - every time he reached behind to do the clips up, the bra rode high on his chest and the clips were too high to reach. He decided to seek help.

"Mum! Can you come and help me please," he called.

"I've just had a message from your father, I've got to go and collect him from the station," came the answer. "Karen help your brother." The station at Haywards Heath was some 10 or 15 minutes away by car, so she would be gone for half an hour or so.

Karen came into Andy's room, accompanied by Susie and Amy. Andy was mortified.

"I'm having trouble with this," he said indicating the bra.

"I'm not surprised. It's upside down, you wally," replied his sister unsympathetically. "Take it off and we'll help you."

"Nice knickers," said Susie with a grin. Amy giggled.

"Don't be horrible to Mandy," she said. "It must be very embarrassing for her." Andy's mortification increased as the girl he had a crush on referred to him as 'Mandy' and 'her' while he was wearing nothing but a pair of girl's panties. The bra was expertly done up correctly and Karen adjusted the straps. Karen investigated the bag to see what else needed to be applied.

"Oh, brilliant, breast forms. Mum's a genius. I bet none of the other girls are going to have these," said Karen and she slipped them deftly into the bra.

Andy bounced gently up and down to feel the effect.

"Thery're quite heavy," he observed. All four youngsters examined the jiggling of Andy's breasts.

"Tights next," said Susie.

"Aren't we going to paint her toes?" said Amy.

"No we bloody well aren't!" said Andy indignantly.

"That's not very ladylike," said Karen.

"Sorry."

"Don't apologise to me," said Karen. "Apologise to Amy. She's the one you swore at."

"Sorry Amy."

"Don't worry. It's my fault, I'm just so excited. I can't wait to see my new friend." Andy felt heartened by that last statement.

"I don't think we'll paint her toes tonight. We'll only have to take the paint off again. OK Andy, how do you think you put tights on?"

"How should I know? Like pants? Grab the top and and shove a leg in each side then pull them up, I suppose."

Susie grinned and Amy had another attack of giggles.

"You'll tear them if you do that and the crotch will be below your knees. Oh, hang on a minute, your legs are a bit hairy. Come with me." Karen led the way along the corridor to the bathroom. She made Andy sit on the side of the bathwhile she squirted shaving foam up and down both legs. Susie and Amy came along to watch. Karen used long strokes up and down the nervous Andy's thighs and calves, rinsing the razor frequently under running water. After several minutes she was happy and she ran the shower over Andy's legs to remove the last remnants of shaving foam. Next she sqeezed some moisturizer into her hand and rubbed it up and down Andy's legs. Andy's level of mortification level reached unprecedented heights as it became apparent to all four that he was enjoying this attention.

"Oh, for goodness sake. Control yourself!" said Karen impatiently. "I think we'd better leave until that bite-size Mars bar settles down." The three girls departed. Andy's mortification level came back down onto the scale. Karen returned with a pair of tights and knocked on the bathroom door.

"Are you decent?" she called.

"Sort of," came the reply. Muffled giggling came from the bedroom indicating that Andy's reply had not gone unheard.

Karen entered the bathroom and surveyed her brother.

"Let's try putting these on. It might calm things down a bit," she said. "Scrunch one leg down until you can put your thumbs in the toe." Andy did as instructed.

"Good, now pull down over your ankle and up your calf. OK stop there, now repeat with your other leg and take it up to your knee. That's it. Now slide your first leg up, then your other leg and make sure it fits snugly between your legs. Well done - do you think you could that without me helping you?"

Andy nodded.

"OK, lets go through to my room." Andy followed Karen out of the bathroom.

"Sit there," Karen pointed to her vanity. "Now look at me. I just need to tidy your eyebrows up a little." Karen took her tweezers and pulled a few eyebrow hairs from the centre.

"Oww, that hurts," complained Andy.

"Stop being a baby," said Karen. "Girls have to do this all the time."

Andy braced himself for a renewed onslaught. Karen tweezed and Andy winced for a minute or two, then Karen leaned back to assess her work.

"That should be OK," she said. Susie and Amy nodded in agreement.

"Susie's going to put some make-up on you. It's nothing worry about. It won't hurt; it washes off easily and it's something we girls do every day. Some of us more than others."

Susie went to work with foundation, eye-shadow, and blusher, none of which Andy found too uncomfortable.

"Now Andy, sit still, I'm going to put eye-liner on you," said Susie. "It won't hurt as long as you don't flinch, otherwise I might poke you in the eye."

Andy looked with considerable apprehension as the eye-liner pencil approached his eye. As it touched him, he pulled away; he hadn't expected Susie to press so hard on his eyelid. Karen and Amy looked on attentively.

"Come on Andy, it doesn't hurt. Don't be a baby," said Karen.

"Be gentle," said Amy, "I remember the first time Susie put eye-liner on me. It's not very nice until you get used to it."

"Sorry," said Andy. He steeled himself to the next attack of the pencil, reassured that Amy had lived through a similar horror.

"Good," said Susie, "that's the worst bit over. Now just a bit of lippy and you can look at yourself in the mirror."

Susie applied the lipstick and had Andy purse his lips then rub his lips together to even out the lipstick.

"OK Andy, meet Mandy," said Susie. Andy turned round to see his reflection. A pretty girl looked back from the mirror.

"Oh my god," said Andy, "I look like a girl."

"Well, duh," said Karen.

"You look like a really pretty girl," said Amy. "You look lovely. I knew you would. Now for the really fun part - trying on lots of clothes."

A door banged downstairs announcing the arrival of Karen and Andy's parents. Footsteps were heard on the stairs and their father called a cheery good evening.

"Hi dad."

"Hi Mr Jacobs."

"Oh hullo, who have we got in there then?" said Mr Jacobs.

"It's just us and Susie and Amy."

"Can I come in?"

"Yes," said Karen.

"No," said Andy.

"Make your minds up," said Mr Jacobs.

"Can you give us a minute or two please dad. She's decent but she'd like to be a bit more decent, if you catch my drift," explained Karen.

"Right-ho, I'll just go and change."

"Don't tell dad I'm she, I'm a he," said Andy.

"Pardon?" said Karen.

"You said *she's* decent, you should have said *he's* decent."

"Oh well, you look like a she."

"I do not!"

"Look in the mirror," said Susie.

Andy did so and became quiet again.

"Come on, put your slip on," said Amy.

"That's a petticoat; I'm not wearing that." said Andy.

"No a petticoat is fuller, it makes a dress stick out and gives it a fuller shape. That's just a slip. It helps stop your skirt sticking to your legs and riding up. You don't want your skirt riding up and showing your knickers do you?" said Karen.

Andy apparently did not want his skirt riding up and showing his knickers, so he stepped into the slip and pulled it up so the waist was at the level he was accustomed to wear his jeans, some 6 inches below his navel.

"Pull it up properly," said Karen, "a girl doesn't want her slip showing." Amy giggled and Andy blushed as he pulled the slip up a bit higher.

"What do you want to try on first?" said Amy excitedly.

"I dunno," shrugged Andy.

"Try this," Karen handed him a red T and black skirt that reached almost to his knee.

Andy slipped the T over his head, then stepped into the skirt and pulled it up. For all that he was thin, he had difficulty doing the zip up and fastening the button.

"It's a bit tight." he said doubtfully.

"Yeah," said Karen, "we might need mum to give us some advice with that."

"I think it looks OK." said Susie. "Have you got some shoes?"

"Try these," said Karen proffering a pair of court shoes with a two inch heel.

"That's not bad. That's no bad at all," said Karen.

"You look fab, Mandy," said Amy. "Come on, let's go and show your mum."

"Oh, god, do I have to?" said Andy.

"Yes of course, she's dying to meet you," said Karen.

The three genuine girls dashed down the stairs, followed after a considerable pause by the newest girl, who reluctantly appeared, nervously round the door and slunk into the living room.

"Hello, Mandy," said his mother, "you look very nice. Do a twirl." Mandy stomped round in a small circle.

"You girls are going to have to do a lot of work on her deportment. She looks like a very pretty girl but she moves like a typical teenage boy. Mandy, when you walk lean back and look forward, take small steps, try to put one foot in front of the other." Mandy walked the length of the living room, feeling very foolish and self-conscious. Amy walked alongside her new girl friend to make her feel less nervous.

"Mandy said the waist on her skirt was a bit tight," said Mandy. "What do you think mum?"

"Yes it is rather," said her mother, "we'll have to do something about that."

Mandy continued to practice her walking trying to take in all the instructions about the feminine way to swing her arms, move her hips and take short steps.

After a few minutes further footsteps were heard on the stairs announcing the arrival of Karen and Mandy's father. Gone was the business suit he wore to his office in London. Gone too was his moustache and, rather unexpectedly, his attire comprised a white blouse, black knee-length skirt, shoulder-length wig, eye-shadow and lipstick, black hose and flat-heeled black patent leather shoes. The four teenagers looked at him (her?) in utter bewilderment.

"I suppose you're wondering why I am dressed like this?" he asked. The youngsters were too stunned to reply. "Well, Jane had a bit of a chat with me last night after she found out about my dressing as a girl when I was a teenager. She told me I ought to provide young Mandy with a bit of support. You know, show of solidarity, that sort of thing. Is that alright with you Mandy, old chap?"

"Yeah, that's fine dad, er do I still call you dad?" Mandy was a bit unsure of the corrct way to address a transvestite father.

"You call her Dierdre," announced his mother.

"Dierdre?" Karen found her voice. "That is brilliant!"

"Can I call you Dierdre as well, Mr Jacobs?" asked Amy politely.

"Yes, I suppose so Amy."

"Oh this is wonderful. I thought I was going to have one new friend this evening and now I've got two. I'm so happy." With that Amy went and gave both her new girl friends a big hug.

"Come on Mandy, lets go and find a different outfit for you." Amy grabbed Mandy by the hand and hurried out of the room and up the stairs, Mandy going as fast as she could in the unfamiliar heels. Karen and Susie followed.

Mandy had to suffer the indignity of several different outfits. Gradually she began to say what she liked and which outfits she preferred. The girls also pointed out boy mannerisms and showed her how to use girl mannerisms instead - for example, holding her elbows close to her side and gesticulating with a relaxed wrist. They showed her how to take small steps and swing her hips when she walked and by 8:30 it was decided that Mandy was ready for her first outing. She was wearing a knee length dress in white with a pale floral pattern.

Mandy was a bundle of nerves as they left the house to walk Susie and Amy back to their house.

"What if someone sees me?" she asked nervously.

"They'll just think they're seeing an ordinary girl." said Susie.

"But I'm really a boy."

"They won't see that," said Susie. "Come on, I'll take one arm, Amy you grab the other."

And the four girls walked arm in arm along the quiet lane to Susie and Amy's home.

Amy's parents had divorced a few years ago. This was one reason why Amy felt so close to Karen and Mandy's dad. He was just the perfect man to be a dad. He never got angry, he was always reliable and he was so funny.

The scent of flowers hung in the air as dusk fell on the warm spring evening. They soon came to Susie and Amy's home, a delightful cottage on the edge of the village.

"Hi mum, we're back," called Susie as she opened the front door. "We've got someone to introduce to you."

"Oh, Mandy you look lovely," said Jo. "That's a really pretty dress. Who did your hair? Tracey? She's brilliant isn't she. Susie did your make-up didn't she? I can always tell. Welcome to the girl's club dear. You're going to have so much fun over the next few weeks."

"Thank you Jo," said Mandy.

"Mum," said Amy, "you'll never guess what Karen and Mandy's dad did. He dressed as a woman to give Mandy some support. Isn't he the best?"

"He is certainly unusual."

"And he wants to be called Dierdre."

"That isn't strictly true, Amy," corrected Karen. "Mum said we should call him Dierdre when he's dressed as a woman."

"Do you know," said Jo, "Dierdre suits him. If Dierdre was a man's name, he would definitely be a Dierdre. Have you two got time to stay for a drink of coffee or cocoa?"

"We really should get back," said Karen, "It's getting dark and we have school tomorrow."

Amy walked with Karen and Mandy to the front door. They were just leaving when she pulled Mandy to her and kissed her right on the lips.

"Thank you for doing this," she said. "You're so brave and I want to see you every day until the pageant."

Mandy was completely taken aback. "And I would love to see you every day too." Tentatively, she leant forward and their lips met again, a little longer this time.

Amy pulled away, "I must go, see you tomorrow Mandy take care, bye Karen."

Amy shut the door and Karen and Mandy walked home arm in arm. Mandy had never felt happier or more loved by people outside his immediate family.

They arrived back home to the unusual sight of their mother watching the television while Dierdre was cleaning the kitchen. Her skirt and blouse were protected by a bib apron in a loud floral pattern and pink rubber gloves.

Karen gave her a big hug, "Oh Dierdre, I love you and gave her a big kiss on the cheek."

"And I love you too Karen," replied Dierdre.

"Yeah Dierdre, thanks for doing this," said Mandy who was still finding it difficult to express her feelings.

Dierdre gave Mandy a quick hug. "You're the brave one, you're standing up in front of people. Good for you. Oh and I think your mother might have another surprise for you."

"Mum, Dad, I mean Dierdre says you have something for me," said Mandy.

"Yes, Mandy, come with me to the bathroom and let's get that make-up off." Mandy followed her mother upstairs.

"Take your dress off and hang it up" When Mandy had taken her dress off, her mother showed her how to use wipes to remove make-up, then wash her face and apply moisturiser.

"No go into your room and you'll find the surprise."

Mandy went to her room. On the bed was a pair of satin girls pyjamas in a rich dark blue, the pants reached just below the knee and the sleeves just below the elbow. She took off her tights, panties and bra and then she put them on. They felt so smooth and silky against her newly shaved legs. Mandy felt special, she went and hugged her mother.

"Thanks for all the things you got for me today mum," said Mandy.

"So how are you enjoying being a girl?" asked his mum.

"I thought it would be really boring, you know. Girls are always talking about dresses and make-up and stuff but its OK. It's almost like art. But the thing I really like is that everyone is being so nice. And Amy kissed me."

"Amy is lovely. She is still very young," said mum. "I think she would like a boyfriend but she feels threatened by boys - especially after the way her parents divorced. Just be nice to her and treat her with respect, and she may well grow to love Andy as well as Mandy."

Mandy went to bed that night and slept the happiest sleep (s)he could remember.

To be continued

  

  

  

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