Debbie at 17

by Debbie Valentine

 

I giggle girlishly as I pull my clingy white leotard-style top up my sleeves, adoring the way it tightly embraces my arms the same way it embraces my corset-enhanced torso, my (admittedly fake) breasts and my smooth, flattened, feminine crotch. Smiling through hot pink lips, I mince toward my suitcase to pick out a dress to wear today.

My name is David Vincent, or as I've taken to calling myself, Debbie Vincent (after the heroine of one of my favourite novels). I'm a seventeen year-old transvestite from Ireland, and my mother is away all day today, so I can spend the whole morning and afternoon being Debbie!

I started as I always do- removing all my body hair, brushing my long blonde hair into a girly style (it's shorter than it used to be, and I've sort-of got a cute fringe now, hehe!), pulling a condom over my lad and taping it down and out of the way, and inserting a large tampon into my arse. Then I applied my make-up- some hot pink eyeshadow and a thick layer of hot pink lipstick, and an equally thick layer of mascara. I paint both my toenails and fingernails black and spray on some perfume before putting on my jewellery- just some rings, earrings and bracelets to make me look as girly as possible- which is taking less and less effort nowadays!

As it's November I've gone for slightly warmer clothing than usual- I started as always with my tight underbust corset, taking my waist in several inches and giving me a sexy hourglass figure. Then, I rolled a pair of nearly opaque black tights up my legs before donning the leotard/bodysuit I described earlier. This bodysuit doesn't have poppers on the gusset like most of the ones I 'rescued' from my mother and sister have, but it does have a built-in bra, giving my fake breasts a perfect outline!

I pick out a dress I 'rescued' from my sister (it was going to go to a charity store, but I decided I was more needy, hehe!) before she went to uni- it's a cute black denim minidress and as I pull it down over my head, I can feel it begin to hug my breasts and my waist, whilst flaring out at the bottom, the perfect shape for a casual dress in my opinion. The square front of the dress and my polo-necked leotard simply go perfectly together- and once I've donned my 2" heeled knee-high boots, absolutely no one in the world would ever mistake me for anything even closely resembling a man.

The way the dress moves around my legs is just wonderful- I've worn countless denim dresses and skirts before, but this one is something special, I can even slouch and walk mannishly and still feel girlish, the way the dress sways as I involuntarily wiggle my arse (hey, that tampon's large, you know!). Even when I sit down, just crossing and uncrossing my legs makes me feel like a cute teenage girl, maybe on a date with her boyfriend, maybe out shopping for more cute clothes with her girlfriends.

I 'model' the dress for myself for fifteen minutes, admiring my girlish body and trying to see if there are any flaws in my 'costume'- of course, there are none. Satisfied and smiling, I put on a Spice Girls CD (girl power!) and study my ballet manual a little more- I've had to wash my ballet leotard today whilst my mother is out so no practice, but I can at least swot up on the theory- ever since I slimmed down like I've done recently, I've been so flexible- able to lift my leg up high and able to do the splits whenever the need calls for it.

I eat lunch- just some instant noodles- admiring my black-tipped and jewellery-covered fingers as they daintily grip the fork (I'm even eating like a girl now!). Once I've finished my lunch and put away my ballet manual, I mince into my mother's bedroom to retrieve an article of clothing I've had my eye on for a while.

I smile happily as I pull the powder pink skirt suit out of my mother's wardrobe and hold it up against myself, admiring the way it seems almost tailored for me instead of my mother. Not wasting any time, I strip off my dress, bodysuit and tights and attach the corset's garters before rolling a pair of shiny, sheer lace-topped stockings up my legs, attaching them securely to the garters. I then pull on a really sexy lace bra and thong panty set my sister left with her last charity donation- I've only started wearing thongs recently but they feel so comfortable, the way they grab my crotch tightly, and the way the thin lace rubs up between my arse cheeks makes me feel sexy but vulnerable at the same time- just like a girl should. I clip the bra on and fill the cups with the padding before standing in front of my mother's full-length mirror, admiring my sexy, curvy body adorned with lacy lingerie. I rarely get the chance to see myself like this, I kind of don't want to put on any more clothes- especially the way my thong looks, pulled up tight against my tampon-plugged arsehole- but I've craved this suit for so long, I know I can't resist wearing it!

I pull on a lacy black camisole over my head, covering up my bra and corset, and slowly pull the tight pink miniskirt up my nylon-sheathed legs. I've always loved seeing skirt suits on women- especially the ones where the skirts are mini, sometimes so short they can't help but flash their knickers- how a woman can look so dignified, so formal but so sultry, so sexy and even sluttish at the same time- this is the way I want to be for the rest of my life. All the heroines in my romance novels are usually secretaries or office managers wearing short skirt suits to work, and invariably, all of them end up bent over a desk, being humped from behind by their hunky heroes. It goes without saying that this is also the way I want to be for the rest of my life.

I zip the skirt up and it hugs my arse tightly, whilst showing off almost ¾ of my sheer, smooth legs- after pulling on the fitted jacket (that fits beautifully around my corseted waist and pushed-up breasts), I slip my feet into a pair of my mother's pink 4" stiletto heeled pumps- they're a size too small for me but really, I don't care in the least- I just want to be the sexy businesswoman I've always known I was, deep down. I sit down at my mother's desk, my limbs already shaking with excitement, and slowly cross my legs, gasping at the sensation of my nylon stockings rubbing against each other. I hastily uncross my legs again as I orgasm for the first time today, panting loudly in my chair as I buck back and forth, rubbing my legs together hard to generate the sensations I crave every second of every day.

It hurts me to be a boy. Hurts me so much that being a girl (which, despite the infrequency of it, is normal to me) creates such strong sensations for me. It feels so right, it just does...

Once my orgasm subsides, I cross my legs again, loving the way my thong rubs against me as I shift around in my chair. I study my ballet manual a little more whilst listening to some All Saints and B*Witched (I love those girls- they're such good dancers, and Irish too!). My minds, though, inevitably turns to those heroines in those romantic novels, and their heroes taking them from behind over their office desks... I own a dildo. It wouldn't be too much to penetrate myself with it, would it?

It's a hard decision, but in the end, I decide not to- for one thing, the dildo I own is huge, I can barely fit it all in my mouth (but that doesn't stop me from trying, hehe!) and it'd rip my poor arsehole apart. However, that just means that I'm going to have to start making my arse wider somehow. Starting tonight.

After a while, I strip off the suit and shoes and replace them carefully in my mother's wardrobe. I take off all my lingerie and place it back inside my suitcase, before entering the bathroom to remove my tampon and scrub away all my make-up, all trace of the girl I really am. I look in the mirror and once again see David, but I know that tonight, even without sexy lingerie or a short skirt on, I'll be Debbie again, with my finger embedded deep inside my arsehole... and I can't wait!

  

  

  

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