Debbie at 16

by Debbie Valentine

 

I feel almost giddy with excitement as I pull the large suitcase out from underneath my bed. I am fully showered and shaved all over, my long blonde hair brushed out in as feminine a style I can make it (yet still be able to tie it back at a moment's notice).

My name is David Vincent, I'm sixteen years old and for as long as I can remember, I've known that deep down inside, I'm not a man, but a woman. Inside the suitcase is a collection of my sister's and my mother's feminine attire, clothing, lingerie, jewellery and make-up that I have 'rescued' over the years from bags intended for charity shops/collections. Given how fast the women in my family seem to go through clothes, I have quite a lot of stuff in here!

I begin as I always do- inserting one of my mother's large tampons into my anus (I still get a little embarrassed by this- I need to stop thinking of myself as my mother's son and start thinking of myself as my mother's daughter!). I'm gradually getting used to the size of the tubes but it still stretches me uncomfortably to start with- I soon get used to (and crave!) the feeling though. Once I'm 'plugged', I slip a condom over my lad and start taping it down so that it won't give me any unsightly bulges during my day.

My sister moved out to university some time ago and my mother's away all day today, some church thing apparently, so I've got the entire house to myself today, an opportunity I intend to make the most of! After slipping on a silky black bra and briefs set that used to belong to my sister (and filling out the cups as necessary with socks), I sit down in front of the bathroom mirror and begin to apply my jewellery and make-up. After rubbing foundation into my face, I apply some thick mascara and purple eyeshadow before liberally coating my pouting lips with my favourite pink lipstick. Smiling a cute, feminine pink smile, I clip a pair of hoop earrings onto my unpierced lobes, clip a silver nacklace around my neck and slip three silver rings onto my hand, one on my left thumb, one on my left middle finger and one on my right middle finger (the jewellery I all 'borrow' from my mother- but I'm always careful to replace it exactly at the end of the day!). A couple of bracelets onto my right wrist and, aside from the obvious stuffing in my bra, you'd never be able to tell I was a boy- even my crotch is nice and smooth!

After applying a coat of blue nail polish to my toenails and some pink to my fingernails, I pick out my first outfit for today. The first thing I know I have to wear is my most recent 'rescue'- a tight-looking corset my mother got rid of last week and I've been dying to try on. It has laces at the back, but I think I've figured out a way of looping them onto the doorhandle and tying them that way. Carefully, I slip into the garment, enjoying the feeling of the satin lining against my smooth skin. Then, I loop the laces around the doorhandle and walk away, gasping as I feel the rigid bones of the corset mercilessly pull my waist inwards and, to my surprise, push my chest, hips and arse outwards. Tighetening it as far as I can go, I tie the laces together and admire my new, ultra-slim (I've lost almost 20 pounds in the last year in an effort to fit my girly clothes better) yet ultra-curvy body in my mother's full-length mirror. Smiling, I pick out a pair of dark patterned tights from my suitcase and try to bend down to put them on.

Realising my mistake in trying to bend while I've got the corset on, I sit on the edge of the bed and slowly slip the tights on over my blue-topped toes, smoothing the garment against my legs until it reaches my hips, where I run a hand over my smooth, nylon-and-silk-covered crotch, smiling sadly as I wish I could feel the smoothness every second of every day...

With my underwear all sorted, I turn to my suitcase to decide how to complete my outfit. I settle on a mid-thigh denim miniskirt, pulling it up my legs (and struggling with the corset!) and letting it rest on my new-found hips, loving the way the denim hugs my arse and shows off my slim legs beautifully. On top, I pull on a sleeved khaki top that once belonged to my sister- it was skin-tight on her, and she was tiny following years of gymnastics and ballet, so the first time I tried it on, it looked hideous on my podgy body. Now I have the corset, though, it looks so sexy on me- I even slide the tops of the sleeves down a bit, giggling kinkily as I deliberately expose my black bra straps. I slip my feet into a pair of 3.5"-heeled ankle boots and fasten the clasps, before standing up straight and admiring the sexy young teenager I see before me in the mirror.

As ever, I spend a good long time admiring my new appearance in the mirror, before putting on some music (yes, Spice Girls!) and picking out something to read. Over the past few weeks I've been buying some trashy romance novels and reading them like mad- every word I read, I place myself in the shoes of the heroine, gradually falling in love with the hunky guy and eventually being taken by him the way a woman is taken by a man. I close my eyes and lay back on the bed, rubbing my nylon-covered legs together and imagining being kissed all over by said hunky guy, and having his lad penetrate my girlhood. I don't care what I may in reality have between my legs, all I know is that this is what I want. I reach underneath my skirt and start rubbing my crotch where my vulva should be, and before long, I gasp as I ejaculate, my hips pumping upward in the bed in response to some invisible lover until gradually, my orgasm subsides. I stare over my false breasts at my dark-tinted knees and for the next few minutes I just lay still, taking in all the feminine feelings I can.

Eventually though, I hop off the bed and begin to strip off my clothing, even my corset, until I'm left in just my bra and panties. I even remove my tampon and flush it away, before heading back to my suitcase and pulling out an old photocopied manual, a pair of silky white tights and a long-sleeved black leotard.

Ever since I first found my sister's ballet gear a year ago, I've fallen in love with the whole concept of ballet. The sheer grace and femininity of the dancers is something I aspire to more than anything else, and when my sister moved out, I was almost literally praying she'd discard her ballet gear so that I might have it full-time. Luckily for me, she did, and as often as I can, I have been dressing up as the ballerina I want to be (she didn't leave behind a tutu or a dance skirt of any kind, but I'm thankful for what I do have) and practising steps out of the photocopied ballet manual. Over the past 12 months, I've got to be pretty good, even if I do say so myself!

I begin as ever, slipping the opaque tights over my toes and smoothing them up my legs until they're wrinkle-free all the way up (this is happening earlier and earlier nowadays- fortunately I'm not that tall and not growing fast so there's still life left in the tights yet!). Then, I bunch up the leotard and slowly step into it, letting out a small sigh as it embraces my already-flattened crotch and clings to my (non-corset enhanced) body all the way up to my shoulders, even hugging my skinny arms tightly. The leotard won't last forever either, but hopefully when I need a new one, I'll have the guts to buy a new one!

After tying my hair back into a bun, I reach back into my suitcase and pull out a pair of pointe shoes my sister discarded a year ago. They've not quite got the lustre they once had but for dancing, they'll have to do. I slip my feet into them and tie the ribbons around my ankles and lower calves, before straightening out, removing any wrinkles from the tights around my (fantastically smooth) crotch area, and turning to the "warm-up exercises" page in my manual.

The warm-ups usually consist of a few simple stretches- I can almost do the splits fully now, nearly getting my crotch all the way down to the ground! I don't have a barre per se but A high desk usually suffices (as long as I don't mind a few grooves on my ankles afterwards, hehe!). After stretching, I'm ready for my favourite aspect of ballet- the pointe work. Even though my pointe shoes are not what they once were, I love the feeling of dancing in such a dainty, feminine way. Looking in the mirror and seeing myself as a teenage ballet dancer, balancing on the tips of her toes and dressed in a tight black leotard where the only noticeable bumps are her breasts, I lose control and have to lie down on the bed again, experiencing my second orgasm of the day. I rub my nylon and lycra-covered crotch as I come into my condom, adoring the feeling of nothing under my hand- no penis, no testicles, just a smooth, featureless mound. How lucky biological women are!

After a few more steps, I decide that my ballet lesson is over- I've been dressed for almost three hours now, and my mother will be returning soon, so I need to get changed into my final outfit for the day (I always wear three outfits a day when dressing up, don't ask me why!). Returning my pointe shoes, leotard and tights to the suitcase, I also remove my bra and panties and replace them with a very sexy, very lacy red and black set, the panties hug my hips and bottom close and the bra (after having the "enhancements" added, of course) gives me an amazing push-up! After re-applying my tampon, replacing my condom and touching up my lipstick, I head back into my suitcase and attach 6 garters to the bottom of the corset I had worn earlier. I've never worn stockings and suspenders before, so this is something I'm really looking forward to! I lace myself into my corset as tightly as before, gasping out of lack of breath and out of excitement as my waist is constricted and my body becomes ever more feminine with every inch shaved off. Once I'm fully laced in, I take out a pair of lace-topped fishnet stockings my mother had discarded some time ago, and slowly roll each stocking up my legs, loving as always the very different feel of fishnet against my calves and thighs, and sighing at the new feeling of the lace encircling the top of my hairless leg. I slowly clip both stockings to the garters and try walking about a little, even loving the feeling of the garters rubbing the tops of my thighs.

Happy with how I look in my underwear (I love that- "my" corset, "my" stockings, not my mother's or my sister's, "I" am in control of my female side), I head into my suitcase and pull out a translucent white blouse (I'm in a "slutty" mood this afternoon, hehe!) and a purple velvet pencil skirt with a flared hem- this is also something I recently rescued from a charity collection and have been dying to try on- it's so narrow all the way down, I can't imagine how it'll feel on my legs! After I do up all the buttons on the blouse (and I love how it feels- so light, so floaty, but you can still see my bra and corset through it, hehe!), I slowly slip into the skirt, pulling it up my legs and simply adoring how it pulls my thighs together as I zip it up and fasten the wide purple belt. Even the short trip back to my suitcase in stocking feet generates all number of erotic sensations as I'm forced to "mince" because of the skirt, forcing my fishnet-clad thighs to rub against each other. Those sensations are only going to increase though, as I retrieve a pair of purple, 4" spike-heeled pointed-toe pumps from the suitcase and slowly slip my feet into them. Amazingly, they fit like a glove, and when I stand up again, they make my calves look absolutely amazing, just as a woman's should.

I walk around for almost fifteen minutes, usually with one hand on my hip, loving my new way of walking, my new way of living as I get used to the new shoes. Even sitting down, I'm forced to be more feminine- I have to keep my legs firmly pressed together when I sit- even crossing my legs flashes my sexy lace panties in the mirror!

I turn back to my novels, but this time pick out a much more erotic text, hehe! I'm almost shaking with excitement as I pick out one other item from my suitcase- a large, white dildo I found when taking out the rubbish one day- formerly my mother's (which is surprising given that she's a devout Catholic), I've been putting off using this because of my own religious beliefs, but I figure if God is going to frown on me for pretending to be a female, I've got nothing to lose by going the whole hog! I turn to my saved page in the book, rubbing my fishnet-clad thighs together for extra sensation!

"Debbie slowly undid Marco's fly, freeing his engorged penis from its fabric prison. Slowly, she took it in her hand and began gently stroking it, feeling it twitching in her palm."

I begin to stroke the dildo in my free hand, imagining it pulsating as I do so.

Slowly, Debbie sank to her knees, encumbered by the tightness of her skirt, and looked longingly into Marco's eyes as she slowly guided the head of his penis to her lips."

I sink onto my knees beside the bed (experiencing all the problems Debbie had with her skirt!) and bend over as far as my corset will allow me, so that I am gently kissing the head of the dildo.

"Debbie slowly eased Marco's penis into her mouth inch by inch, greedily sucking it with her pouting red lips, licking the vein underneath his penis with her expert tongue."

I gradually take the dildo into my mouth, sucking on it like a baby's dummy and applying licks and kisses as I do so. I take care not to bite it- I treat it as if it were a real lover's penis.

"Debbie finally took the whole length of Marco's penis into her mouth, smiling with her thick, wide lips as his pubic hair tickled her nostrils. She sucked as hard as her mouth would let her, loving the feeling of the penis twitching on her tongue."

I slowly suck the whole length of the dildo into my mouth so that the flared base of it squashed against my nose. The tip of the phallus begins to make me gag as it touches the back of my throat- I feel like such a slut!

"Marco grunted and sighed as he came into Debbie's mouth, pumping his hot semen past Debbie's tongue and down her willing throat. Marco slowly withdrew his flaccid penis from Debbie's mouth, the young secretary sucking it hard so as to leave a coat of her expensive red lipstick along the length of his spent organ. She gave the head of his penis one final, loving kiss before standing up and looking Marco in the eye, making a deliberate, exaggerated swallowing motion before passionately kissing the young man."

I pull the dildo out of my mouth, sucking it hard as I do so. I examine the white phallus after removing it, to discover pink blotches running the entire length of it. I sigh as my third orgasm of the day claims me. I lay still for the next fifteen minutes, just closing my eyes and enjoying being a woman, being 'Debbie'. I finish the next chapter in the book, occasionally pausing to rub my 'enhanced' breasts with my small, smooth hands, when I realise that my mother will be due home in less than 30 minutes. Frowning with disappointment, I put away my book and strip off all my clothes, placing them back into my suitcase before showering again, taking care to remove all traces of make-up from my body. I wish I could tell my mother about the girl I am, but she wouldn't understand- she's always going on at me to find a nice, sweet girl and ask her out- I wish I could be a nice (but not always nice, hehe!) girl that a boy would want to ask out.

Once I'm David again, I walk back into my bedroom and sit down beside my bed, staring at the large suitcase in the darkness underneath. My happiness is inside that suitcase, and I will be happy again...

  

  

  

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