What Have I Done To Deserve This?

by Colin Sigfried

   

Last Day of Term

It was the last day of term, Becky was in her final year at school and I was in the first year of college studying drama and media studies. I suggested to Becky that as it was the last day of term we would spend the day together; no-one would know or really mind. So we went through the charade of getting ready for our respective classes and met in the local park. I was dressed casually and Becky in her school uniform, boy did she look hot, mind you she would look hot in anything. She was very mature and well-developed for her age.

"Let's go back to go my house" Becky said to me, "We can have some fun." I liked the sound of that, so hand in hand we went back to Becky's house.

"Do we have the place to ourselves?" I asked. "Oh yes, my mum and dad are at work and my brothers are at college. So we won't be disturbed. We have all day, well, until about 4:30."

We went straight to Becky's bedroom, she was very lucky as she had a large bedroom with its own ensuite bathroom. Becky was a very girlie girl and wanted to go to Beauty College next year.

"You know I want to go to Beauty school next year?" she asked.

"Yes, I do. I think that's an excellent idea and your good at that sort of thing" I replied.

"Well, you know you said that you would like to help me?"

"Yes" I said curiously.

"As we have the whole day together I would like to style your hair. It's lovely and long and I could work wonders with it. I'll make worth your while" she added.

"What do you mean 'style' it?"

"I would just like to put some highlights through it and give it a style, that's all" she said eagerly.

"What you mean, style it like a girl's hair?" I said worryingly.

"Well, yes, I do need the practice and of course I can't work on my brothers. It would only be temporary and I would re-style it back to a boy's style afterwards. I will make it worth your while, I promise" she said seductively.

Well, I couldn't refuse, she looked so hot in her school uniform and the prospect of making it 'worth my while' was very appealing. "Oh go on then, I wanted a new hairstyle anyway. How long will it take?" I enquired.

"Only a couple of hours, but we do have all day you know."

The New Hairstyle

She marched me into her ensuite bathroom, washed my hair then sat me down. She then proceeded to put highlights in tufts of my hair. I waited patiently as I was looking forward to my 'reward'.

"Right, that's the highlights done, we just need to wait a while for the dye to set. While we're waiting, do you mind if I add a little colour to your face? I would be very grateful" she said with irresistible bambi eyes.

"How can I refuse! Go on then, but be sure to remove it all afterwards." In for a penny in for a pound I thought, but I just kept thinking of the reward.

She sat me down and applied an assortment of her extensive cosmetics to my face. I must admit she did a great job and I freaked when I looked in the mirror. Staring at me was a teenage girl – it was me! "Wow" I said, "you are good at this! But you must wash it off, I can't be seen like this!" I exclaimed with a sense of urgency.

"Relax, I will remove it all. But please let me style your hair first to see the full effect. Then I'll wash it off and fix your hair back. I am very grateful to you Colin for letting me do this you know. Now, let's go downstairs and have some lunch."

We went downstairs and she made us lunch, it seems she just as good with food as she is with hair and make-up. Then we went back to her room and she spent an hour styling my hair. When she finished I looked really like a girl, my hair was similar to hers, it was long and I had a fringe but there were blond highlights in my mousy hair. "Boy, I don't recognise myself, I look like a girl! My God, I think I look like Bridget Fonda!"

"Yeah, you do. Thanks Colin I really do appreciate you letting me do this" she laughed.

"Can you wash off the makeup and re-style my hair now, please?" I asked urgently.

"Yes, but first I must fulfil my part of the bargain" she said excitedly and started to remove her clothes.

Okay, I thought, I guess getting my hair re-styled could wait a bit longer, as I frantically removed my clothes.

We went onto her bed and starting to kiss and cuddle. Before long we were really enjoying each others bodies, the hairstyle and makeup were worth it after all. It was a wonderful experience and well worth being her model for the morning. We both fell into a contented slumber afterwards cuddling each other's naked body.

Annoying Disturbance

Suddenly we were woken with the front door closing.

"Oh my God! It's 4:30 and my mum's home!" exclaimed Becky.

"You better get this muck off my face and fix my hair and let me get out of here!"

"Yes, yes, of course but if she finds you here though, there'll be hell to pay and my brothers will be home soon, they'll kill you!"

"Becky, who have you got in there, love?" said a voice from behind her door.

"Oh just a friend from school, we're doing each other's hair and makeup, mum" responded Becky.

Suddenly we heard more voices downstairs. "Oh no, my brothers have arrived home too."

We were both stark naked and even worse I still had the hair and face of a girl! Becky proceeded to put on her dressing gown, as I remained under the covers.

"How am I going to get out of here? Can I climb down the drainpipe or something?" I started to panic.

"Oh no, you can't do that, have you seen have far down it is? We must think of something."

"Perhaps I could wait until your family have gone out or try and sneak out somehow?" I said worriedly.

"You can't get anything past my mum, she knows I have someone in my room and will listen out for them, she's nosy like that. And, besides, I remembered that we're all going out for pizzas tonight."

"Oh my God! What am I going to do? I'll have to come clean and suffer the consequences. You'll need to restyle my hair pretty damn quick though, I don't want to be seen like this!" I said with an air of gloom.

"If that happens we'll both get into major trouble, probably be grounded forever and definitely won't be allowed to see each other again. We have the whole of the holidays to see each other remember. So I'm sure we can come up with something."

We both started to think hard, our hearts pounding. "Listen", she said "I've thought of a plan to get you out of here, but I don't think your going to like it".

"What? I've got to get out of here. Alive preferably!" I said.

"Well, you could easily pass for a girl. I mean, I have done your hair and make-up and you're about my size" she said.

"I don't like the sound of this!"

"All you'll need to do is go downstairs, dressed as a girl and say you're going home. I will come with you, we can walk to the park and I'll sort you out in the toilets, you can get changed there and I'll fix your hair. Just think of it as practice for your drama studies."

"Oh, I'm not sure about that. I don't think I can pull it off."

"Look, you don't have to say anything, it's only to get passed my mum. Can you think of anything else then?" she said defiantly.

"Well, no, I can't" I said defeatedly.

"Ok, let's do it. You'll have to wear my school uniform" she said.

"What, you mean pretend to be a schoolgirl?" I said alarmingly.

"Well, yes, mum thinks we have come here from school, so you have to be convincing, don't you?"

She then went through her underwear drawer and passed me a pair of white lacy knickers and matching bra and asked me to put them on.

"What are these? Can't I wear my own underwear?" I was shocked.

"A girl of your age would have breasts Colin, so you'll need to wear a bra. Also, you'll be wearing a school skirt and you can't wear boxers underneath it. You will have to be convincing down to the nearest detail. We can't afford to get caught and it's only for few minutes" she said very convincingly.

It seems she had thought of everything, had it not been for the embarrassing situation I was in, I might have shown her more respect.

"But these are very girlie, haven't you go anything plainer?" I protested.

"You don't get male bras Colin. And besides everything I have is very girlie. I'm a girl and enjoy it. I take pride in my appearance even down to my underwear."

Well, that's very true I thought and perhaps why I feel myself falling in love with her. She takes so much pride in her appearance.

"Honey, we're leaving in an hour, can you be ready please?" Came her mother's voice from behind her door.

We both looked at each other and reluctantly I put on the lacy knickers, Becky then encased me into the bra and stuffed another 2 pairs of her knickers into the bra to give me 'breasts'. I must admit the knickers did feel strangely comfortable if the bra was a little restrictive. It was a good job that me and Becky were the same size,

"That feels very weird" I stated, "Wearing your underwear and having breasts. I know I wanted to get into your knickers but this is taking it literally!"

She then passed me some navy tights and explained they would cover my slightly hairy legs. She helped me roll the tights up both legs. Then came the white fitted blouse and navy jumper. "Right, just to finish here's the skirt and shoes."

I couldn't believe I was doing this as I pulled the short, navy pleated skirt up to my waist and zipped it up, it was a little tight but would do for the disguise. I then placed my feet in what appeared to be navy ballet shoes, they too were a little tight. "Oh my God!" I said, "I do look like a schoolgirl!" as I saw myself in the mirror. I couldn't believe it, here I was a 17 year-old boy dressed as a 16 year old schoolgirl. But not only that, I was wearing my girlfriend's underwear and school uniform and had to pass myself off as a girl!! Becky then started to get dressed into her uniform and re-applied her make-up (and mine!). She packed some cosmetics into her handbag and a pair of scissors. She passed me her pink rucksack.

"Now, put your clothes in here and let's get out of here" she demanded.

"Oh, I don't know, this feels weird and I don't think I can do it!" I said with an element of fear.

"Oh come on Colin. I know this must be hard for you but we look like a couple of schoolgirls, I've done a great job on you – even if I say so myself. Look, we've got to get moving as I've got to be out in half an hour" she exclaimed.

So we left her bedroom, I looked at the floor with incredible embarrassment and tried to get a feel for my new outfit. Although I felt quite encased in the uniform, I did feel quite comfortable. It did feel quite nice with the skirt brushing against my tights as I walked. We walked down the stairs to be greeted by her mother.

"Oh, there you are dear. Aren't you ready yet? We're going in half an hour love? Who's you friend?" her mother asked.

"Oh, er, this is er is Bridget, mum. I'm just seeing her off, I won't be long. I won't see her until next term" replied Becky. I felt incredibly uncomfortable and couldn't wait to leave.

"Pleased to meet you Bridget, I'm Ann. I must say Becky has done a great job of your hair and makeup dear. Are you new to the school?" her mother directed at me.

"Pleased to meet you too, yes, I am new" I said in a suitably girlie voice – I knew my drama lessons would pay off sometime.

"So, you haven't eaten yet have you Bridget?" her mother enquired.

"No, just off home now" I replied.

"Well, come out with us for a pizza, I'm sure your mum won't mind. We can get to know you" Ann demanded.

"Well, er, that's er very nice of you, but" I stumbled clumsily over the words.

"That's settled then, come out with us and we'll take you home later dear. I'm sure your mum won't mind, why don't you call her or text her. You won't want to go in your school uniform, I'm sure Becky can lend you something to wear."

Oh no, I thought to myself, I've been backed into a corner, what do I do now. I couldn't muster anything to say and looked at the ground.

"Right girls, go and get changed and be down in 20 minutes please. Chop! Chop!" She bellowed.

To be continued…

  

  

  

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