Debbie at 15

by Debbie Valentine

 

My hands are shaking with anticipation- it's a big day for me. My mother and sister are both away, looking at potential universities, leaving me alone in the home. My name is David, David Vincent, and I am a fifteen-year old transvestite. I've been dressing in my sister's clothes since I was eight years old and to me, it feels like the most natural thing in the world.

When I'm sure that my mother and sister are gone (my father is sadly gone too- he died when I was very young), I head into my bathroom and take a hot shower, washing my shoulder-length blond hair in my sister's sweet-smelling shampoo. When I've finished washing my hair, I take a bottle of my mum's hair remover and rub it all over my body, washing it off to remove what little body hair I once had. With my skin sparkling and pink, I wrap a towel around my body and a towel around my hair, just the way that women do. After drying my now impressively-smooth body, I suck my finger for a while, coating it in saliva, and slowly ease it up into my arsehole. For some reason, I get a really sexual feeling when I put things in my arse- I think maybe I'm gay or something! After making my arsehole nice and wide, I take out one of my sister's slim tampons and gently ease it into my anus using the applicator provided. I then sort-of "mince" back into my sister's bedroom to continue enjoying my day!

The first thing I know I must do is paint my toenails. I take a bottle of my sister's deep blue polish and, after separating my toes with cotton wool balls, coat each toenail in this luscious colour. When all ten toes are done, I wiggle then back and forth, admiring their new feminine tint. Wanting everything to be perfect when I finally put some clothes on, I brush my hair out into a more feminine style, smiling at how it now frames my sadly still-male face. Unable to put off my excitement at dressing up any longer, I skip over to my sister's underwear drawer, and pick out a cute peach bra and knicker set I've worn many times before and loved every time! The knickers are scanty, almost g-string like with extremely narrow sides and a lace front. Remembering to wrap a condom around my penis and sellotape it all to my testicles (I've had accidents that way before, believe you me!), I slowly ease the knickers up my legs, smoothing them over my crotch and still tampon-filled arse when they reach the top. I then fasten the bra and slip it over my head, loving the feeling of the wide elastic digging into the front and back of my ribs. The cups are a little empty though, so as usual, I roll up some of my thick woollen socks and slip a pair into each cup. Smiling at my new feminine figure, I sit down at my sister's vanity and take a look at what make-up she has on offer.

I love wearing make-up. I have a fairly feminine face shape, so it takes very little to turn me, facially anyway, into a convincing girl. That doesn't mean I should stop at very little, though! I begin by rubbing a gentle moisturiser into my face and following it up with a long-lasting foundation (I'm praying I'll be able to wash it off before my family gets home!). Then, I take my sister's mascara pencil and outline my eyes, before applying a faint touch of pale blue eyeshadow and putting on some of my sister's pink cherry-flavoured lipgloss. I spray on the tiniest scent of my sister's perfume as well- I want to smell nice but not so nice as to give the game away! My make-up done, I almost start to cry as I see the cute teenaged girl looking back at me from the mirror, nothing in her face betraying the fact that she is in fact a he. It's so unfair- why couldn't I have been born a girl and my sister born a boy instead? I don't want to play rugby or watch movies like Die Hard, I love feminine things, like make-up, jewellery and dancing.

That reminds me- I need some jewellery. Looking in my sister's jewellery box, I pull out three rings, one on each middle finger and one on my left thumb, and a silver heart-shaped necklace. I drop a few plastic bangles onto each wrist and attach a pair of clip-on earrings to each lobe in order to complete the effect. Now that my underwear, make-up and jewellery are done, it's time for my favourite bit- deciding what to wear!

There was only one thing I knew I wanted to wear to start with today- my sister's catholic school uniform! To start with, I roll a pair of opaque black tights up my smooth legs, pulling them as straight and smooth as possible once they are at my waist. Then I pull on my sister's school skirt- a very short straight grey skirt that ends five inches above my knee once it's at my waist! I then don her school blouse, tie and blazer, and slip my feet into a pair of her clunky 2 1'2" heel school shoes, loving the sound they make as I "clop clop" throughout the house. Heaven!

I spend a lot of time- at least fifteen minutes- admiring myself in my sister's full-length mirror. I'm no supermodel, but the bra gives my body a really girly shape, and the dark tights and high heel shoes really help to outline my legs, especially my calves. Once I'm done admiring myself, I sit down at my sister's vanity again, unconsciously straightening my skirt and brushing hair out of my face as I do so. I read some of her magazines and play a CD- A Spice Girls CD, of course!

After about an hour and a half of looking through my sister's magazines and books, my eyes are drawn to a slim manual on her top shelf- a manual that simply says "ballet". I never knew she took ballet! If she does, it means she has one of my favourite items of clothing around- a leotard! Squealing girlishly with excitement, I quickly check through her drawers, carefully so as not to arouse suspicion, before I find it in her bottom drawer- a short-sleeved black leotard, three pairs of thick white dancing tights and a pair of ballet shoes with a ribbon tie on them.Breathless with anticipation, I carefully strip off the school uniform and place it back where I found it, until I'm only wearing my bra and panties. Even though I'm so excited about getting to wear a real ballet uniform, the sellotape over my penis is holding perfectly! My arse is feeling kinda sore though, so I head into the bathroom and remove the tampon, before liberally wetting my arsehole again and placing a new tampon up there. Pulling my panties up and mincing back to the bedroom, I take some time to examine my sister's uniform.

The leotard is a plain black one with a fairly high leg, not that I mind- I love the way leotards fit so snugly against my crotch! The tights are opaque but very smooth, I can't wait to see how they feel against my legs! The shoes are a little odd, though- the sole seems thicker around the toe than it does on the bottom! Taking my sister's ballet manual off of her shelf, I can see it's bookmarked at a page entitled "dancing en pointe". It's pretty advanced- she must have been dancing for a while now. How come this is the first I've heard of it? It also looks like it really hurts- balancing on the end of your toes- but the dancers look so dignified, so feminine I know I'm going to have to give it a try.

My hands quivering with excitement, I slowly unroll one of the pairs of tights and slowly begin to ease it up my legs, loving the feeling as the soft fabric rubs against my hairless thighs- these are silky smooth unlike the thick and practical school tights! After checking that my tights are smooth all the way from my toes to my waist, I slowly step into the leotard, loving every sensation as it slowly encages my crotch, the soft nylon embracing my body all the way up until I feel the familiar tug on the top of my shoulders. Unable to contain myself any longer, I collapse onto my sister's bed, sighing as I come into my condom, and falling in love with the sight of my blue toenails encased in soft white tights.

Once I have composed myself, I pull my sister's pointe shoes (as I have learnt they are called) onto my feet and smooth them over my feet, wrapping the ribbons around my lower shins and tying them off about five inches above my ankle. I slip a pink hairband into my hair to keep it out of my face, and now that I look like a proper ballet student, I head over to my sister's vanity to use it as a makeshift barre, stretching as I do so to remove any wrinkles from the crotch area of my tights.

I try to copy some of the steps and positions from the manual but I'm no ballerina! I'm not even all that fit- I can barely lift my leg above ninety degrees in front of me, let alone behind me. I suppose the tampon in my arse doesn't help much either! My sister's lucky- she's been doing gymnastics since she was six, whilst I was lumbered with boring, muddy rugby. Still though, I feel I've given my best, and I turn to the page about dancing en pointe. Slowly, and holding onto the vanity for support, I raise myself onto the tips of my toes. Ow! It hurts more than I expected, but looking into my sister's full-length mirror all I see is a teenaged ballet student in her leotard and tights, standing en pointe, just like the girl in the manual. Shaking all over, I stand down on my feet again and lie down on my sister's bed as a second orgasm rushes over me. If I'm not careful I'll have to change the condom soon!

I attempt to stand en pointe again but it just hurts my toes too much- it must take loads of practice to get it right- and I intend to practice until I do! I must remember to photocopy this manual sometime in the future, maybe next time my sister's out for the day. It'll cost a bit, but it'll be worth it! I slowly untie the pointe shoes from my feet, wanting to savour their soft feeling just a little longer, and place them back in my sister's drawer, alone with the headband, the leotard and the tights, leaving me once again in just my bra and panties. Not finished with my "adventure" just yet, I look in my sister's wardrobe again and find a cute denim minidress, which looks like it'd be just small enough to hug her body beautifully, let alone my own! I find a pair of fishnets tights in my sister's drawers- I love fishnets, the way they caress your legs so differently than normal tights!- and roll them up my legs before zipping myself into the dress, loving the way it pulls my tummy in and pulls my thighs together, making me walk more like a real woman should. On that subject, I select a pair of zip-up ankle boots with a thick 3 inch heel to round off my outfit, my final one of the day.

I admire my new slim figure in my sister's full-length mirror and try walking, 'mincing' around the room in the tight dress and the high heels, before sitting down at my sister's vanity and carrying on as I did earlier- reading her magazines, listening to more Spice Girls and studying the ballet manual a little more. Eventually, though, I notice the clock reading 4pm- one hour before my sister and my mother return. Disappointed that my day as a girl has to end, I remove all my clothing and return it to where it originally came from, except my bra and panties which I hide halfway-down our washbasket (I've been wearing them all day, they'd notice). After removing and disposing of my tampon, I remove all my jewellery and return it to my sister's jewellery case, before heading back into the shower and washing myself down with my boring boy shampoo and shower gel, washing off the make-up on my face and the nail polish on my toes. I put my boy clothes back on and I'm David once again- but I'm already counting down the days until I can be a girl again!

  

  

  

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