tagTranssexuals & CrossdressersInstead of My Sister Ch. 01

Instead of My Sister Ch. 01


For two years I was the apple of my Mother's eye. Then my sister was born. Since then I have come a poor second in the pecking order. Once our Parents got divorced and Dad moved away, things got even worse.

With money being tight, Mum has always had to be careful, but when a cutback needs to be made guess who always gets cut? That's right, me. Some things I can cope with. For instance I don't really mind that I haven't been able to get a haircut at a barber's for years now. I quite like wearing my hair long and Mum prefers it that way. I like making her happy when I can. Some things are more embarrassing though.

When my last decent pair of boxers wore out several months ago I asked Mum if I could have some new underwear. 'Of course' she said. She disappeared into her room and reappeared; holding two pale blue pairs ... of lace trimmed panties.

'These are from a pack I bought for Jessica, but you can have the blue ones.'

Not wanting to make a fuss I took them and wore them. They are a bit snug and, when they see me wearing them, Jess and Mum tease me a bit, but I can cope. The knickers did start a bit of a recurring theme. When I told Mum I didn't have any vests to wear she produced a pink strap top!

Things began to get really weird last summer,four months after my 18th birthday and a few weeks before Jessica took her school examinations. It became clear that she was struggling with maths, which was a problem as the job she was hoping to get when she left school needed her to pass both English and maths. Hoping to earn some credit I offered to help by tutoring my sister.

'Well we think you can help, but we've got something else in mind' replied Mum.

My jaw dropped further and further towards the floor as she outlined the plan, which was, in short, that I should 'help' by impersonating my sister and sitting the exams for her!

I tried to object but one by one my objections were over-ruled. It was true that with my long hair we looked alike. It was true that, since she was tall for a girl and I was short for a boy, we were about the same height and of a similarly slim build. It was also true that I would be certain to pass the exam whereas she might not.

'It's the best way you can help, Peter, do it for you sister and for me.'

I was in a hopeless situation. I couldn't think of a reason they would agree with and to flatly refuse would be letting down my sister and that would make Mum very cross. One day an analyst will earn loads of money trying to sort out the problems caused by the fact that even though she so obviously favoured my sister, I still wanted so badly to make my Mum happy. I agreed.

I had a week to perfect my impersonation. That evening I was made to swap my own clothes for an outfit more 'suitable'. This was rather humiliating. Stripped to the pretty blue panties I was already wearing I had to stand there and be dressed, like a mannequin in a shop window. Certain that I would agree, Mum had already padded an old bra of Jessica's and I was strapped into it. It was a simple white cotton bra, but it served to give me a bust. For what seemed like ages I had to stand there in bra and panties while Mum and Jessica debate over what I should wear. Eventually they agreed on a simple white blouse and a short blue skirt, on the grounds that it was most like the uniform I would have to wear the following week. I was made to wear an old pair of Jessica's flat shoes and then, once Mum had brushed my hair into a plausible style, for the rest of the evening that was it: I was now Jessica! Well not exactly. They both called me Jessica, so I could get used to it but I still had to do all my own chores and do the usual favours for the real Jessica, but if I didn't do it in a feminine enough way, or in a way that matched her style I was criticized. By the end of the evening my impression of my sister was getting quite good. Part of the time was spent copying from an old exercise book of hers so I could recreate her writing.

I actually quite enjoyed myself. The outfit was surprisingly comfortable and to be completely honest it felt quite nice to wear. It was also nice to get praise from Mum when ever I did something particularly well.

The following evening the ritual was repeated, except that this time I was made to wear Jessica's school uniform, once she had changed out of it. This consisted of a fitted white blouse, a maroon jumper, a short, pleated gray skirt and white ankle socks. Oddly, I also had to wear a maroon pair of gym briefs, as this was still part of the uniform requirements. These were a bit snug, but, on the plus side, they served to squash any unfortunate bulges! Mum did my hair again and this time she put on a small amount of make-up (as set down in the uniform code). With the discrete application of some foundation, eye shadow and lipstick I looked, and felt, even more feminine. The look of pure joy in mum's eyes as she admired her handiwork made me happy – even though it was only because I looked like a copy of my sister.

For the rest of the week before the exam I dressed in my sisters clothes every day. I became quite accustomed to wearing short skirts and seeing myself with feminine curves. The highlight of the week was a shopping trip, dressed as Jessica, with Mum to the local mall. Before the trip I had to be given the full treatment. My not-very hairy legs were waxed, my eyebrows plucked and shaped. Once I was made-up as I looked at my reflection even I found it hard to believe I was looking at me. Even so it was a little scary how completely Mum treated me as Jessica. I had never felt so loved and in-tune with Mum before that evening. Okay, I was pretending to be my sister, looking at dresses and high-heeled shoes, but I was getting the attention normally reserved for my sister.

Did I say 'looking' at dresses and high-heeled shoes? Make that 'trying on' Going into the changing rooms of the clothes shop and coming out into the shop wearing the blue dress we'd chosen, so Mum could see how it looked! . Slipping on my first pair of high heels and walking up and down in the shoe shop! Both items looked great, so great that, somewhat bizarrely, Mum bought them! I was going to protest that I didn't actually need them, but Mum was so pleased with them I kept quiet, assuming that she could bring them back for a refund or, more likely, give them straight to my sister.

The day of the exam arrived. It was in the afternoon, so I had all morning to prepare... and all morning to get nervous! Could we really get away with it? The first two parts of the plan went perfectly. I arrived, as planned, a fraction late. All the other candidates were seated ready to start. I went in and took my seat without having to talk to any of Jessica's friends - or should that be my friends? Part two, the exam itself, went perfectly to plan. My handwriting matched Jessica's perfectly and I knew I had enough right to pass the exam. Then things began to go wrong a few minutes before the end of the exam.

I was checking my work through when I became aware of someone standing by my desk.

"Come with me, Jessica"

It was the deputy head-master Mr. Brown. He was a small, bearded man with the first signs of middle-aged spread showing round his waist. Obediently I followed him out of the exam room, very conscious that the eyes of everyone in the hall were in us, and along the corridors to his office. Neither of us spoke. Inside I was in a panic – what did he want to see me for? In his office we were joined by Miss Carlton, one of the senior teachers. She was older than Mr. Brown, but still slim and elegantly dressed in a flattering skirt suit, wearing very high heels.

"Let's be honest, shall we?" Mr. Brown said, "Whilst we will concede that you look very much like the real Jessica, we are firmly of the opinion that you are not, in fact, the real Jessica." I started to protest, but he cut me short. "The real Jessica has never got through an entire maths exam with out asking countless stupid questions, nor has she produced such excellent work. Shall we call the police to sort out your true identity?"

The police! They had to be bluffing. Dumbly I shook my head.

"We have a suggestion that you should consider. Clearly with you taking the exam the real Jessica will pass, which is good for her, but it is also good for us, since it will help us hit the ridiculous targets the government sets us. However you cannot go unpunished. Initially we propose a spanking, which Miss Carlton will administer. What do you say to that Jessica?" He made that annoying gesture of miming the inverted commas he was placing around my current name.

I thought quickly and realized that I had no choice.

"If I agree to be spanked, it'll be the end of the matter?"

"I said 'initially'. They may be other, um, matters to attend to."

I nodded my head and took a deep breath.

"Come over to the desk, bend forward, resting your forearms on the desk."

I took my place bend over the desk. Miss Carlton raised my skirt to reveal my bottom, tightly covered by the maroon briefs. The she went to work bringing her hand sharply down on my bum with a loud slap; it hurt even worse than it sounded. I yelped.

"Silence girl!" she ordered, "That one will not count."

You know the phrase 'six of the best'. That's what I got, each one more painful than the last as the pain burned like fire. Also, in between each slap, her hand lingered on my bottom, almost caressing it.

I realized that by looking at the glass-fronted display case in front of me, I could clearly see their reactions. Judging by the smile on her face Miss Carlton was enjoying herself very much. So too was Mr. Brown. He was staring intently at my exposed rear and by the way his hand kept moving to his crotch I could tell that he was quite aroused by the sight.

After the last slap I was ordered by Miss Carlton to stand up and cover myself up. I stood there waiting, unsure of what would come next. I soon found out.

"You've caused me a bit of a problem young lady," Mr. Brown began, and he gestured down to his crotch, where his arousal was plain to see. "What do you propose to do about it for me? Remember, of course, that you need to keep us both happy."

I hesitated, unsure of his intentions.

"Perhaps it's a shame the young lady wasn't taking an O-level examination this afternoon!" joked Miss Carlton.

I felt my knees tremble. I understood the reference. I'd seen postcards in telephone booths where prostitutes would advertise that they had 'O and A levels'. At first I had wondered why they were advertising exam results, perhaps they thought their clients might want clever women, but I heard some friends talking about it and found out O stood for oral sex and A stood for anal sex.

I didn't fancy performing oral sex on Mr. Brown, but there didn't seem to be much option. I decided to take the initiative before they suggested anything even less appealing.

"I suppose I could help with that Mr. Brown, if you gave me some guidance." I moved towards where he was leaning against the edge of a desk and knelt before him, trying to keep up the feminine act. I reminded myself of two things. I couldn't let Mum down causing Jessica to fail the examination and it was the sight of my bottom being spanked that had caused his excited state.

Reluctantly I unzipped his trousers and on his prompting undid his belt to allow his trousers to fall down around his ankles. He had on a hideous pair of boxers that may once have been white but now were a dingy off-white. There was a damp patch where his pre-cum hand leaked out onto them. I helped his cock out of the boxers where it sprang to attention. Putting off the moment I had to take it in my mouth for as long as possible I cupped his balls in one hand and stroked it with the other, firmly enough to pull back his foreskin. From the soft moaning he made Mr. Brown was enjoying himself and I began to think that I might be able to make him cum without having to put his cock in my mouth.

I was wrong. I felt his hands on the back of my head, pulling me forwards and only by reacting quickly did I make it go into my unwilling mouth and not poke me in the eye. I nearly gagged as his cock thrust forwards into my mouth, but, luckily, I still had his balls cupped in one hand and my other hand was wrapped around his cock. In this way I managed to control his thrusts and force his foreskin back even further. Bravely I began to tease the exposed head of his cock with my tongue, tasting his salty pre-cum.

Then in a flash he came, squirting hot cum into my mouth. I didn't know what to do and faced with the dilemma decided that trying to swallow it was my best bet. In between moans he muttered "Good girl!" so I guess I made the right choice. Luckily after a couple of spurts he was finished, so swallowing it wasn't a problem and it didn't taste too bad. Next Miss Carlton was offering me a tissue and he was pulling up his trousers.

"We'll consider the matter closed then 'Jessica'" he said again miming the inverted commas. "Off you go."

As I opened the office door I turned and said "Thank you Mr. Brown. Thank you Miss Carlton." Looking at their smug, satisfied faces I had done a good job.

Mum was waiting in the car. "Where have you been?" she asked.

"It's a long story" I replied.

She listened intently all the way home. Once out of the car and in our house, she held me in a tight embrace.

"I love you and thank you for doing all those extra things. Go up to your room and change, I've got a surprise for you."

On my bed was the blue dress, some sheer black tights and the high heels. My heart leapt. Amazingly I was thrilled by the fact that Mum wanted me to dress in such pretty things. Swiftly I took off the school uniform and pulled on the tights, being careful not to snag or ladder them. I slipped on the dress and then sat down to try on the shoes. I made my way down stairs, adapting to the high heels with greater ease than I had anticipated.

"You look beautiful!" exclaimed Mum. "I'm taking you out for a meal at that new restaurant as a treat." As we walked out of the house I found myself hoping that I'd get more chances to dress like this in the future...

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