Debbie at 18

by Debbie Valentine

 

"Come on, don't keep me in expense any longer Dave!" Shouts Paul, a university friend of mine and, more notably, the president of the uni's LGBT society.

"Just a minute!" I shout back from my en-suite bathroom (I'm one of the lucky few whose parents, or in my case, parent, has money!), where I'm putting the finishing touches to my look.

My name is David Vincent, or as I prefer to call myself, Debbie Vincent. It's February 2000 and I am an eighteen-year old (almost nineteen, though!) student at Dublin university. And, as you can tell from my inviting the president of the LGBT society over, I am one of those four initials. the T, to be precise.

I admire my look in the mirror one more time- I am wearing a silky black bra and panties set, but these are no ordinary bra and panties- the knickers have a special pouch into which I have inserted my (condom-covered, of course) lad and tied it down so that nothing of it shows on the outside, not even the faintest hint of a bulge. The bra is a "mastectomy bra", specially designed so as to hold inserts and make them look like real breasts, which is exactly what they're doing to the C-cup inserts currently on my chest.

I have a tight waist clincher wrapped around my abdomen, turning my boring male figure into a sexy, curvy hourglass shape. The corset also serves to push out my breasts, hips and arse in just the way I want, too!

My face is made up like that of a girl on a night out. Thick, black mascara and hot pink eyeshadow surrounds my eyes, and my lips are liberally coated in bright pink lipstick (I love pink, in case you couldn't guess!). My long blonde hair is curled so as to fall perfectly around my cute, pouting face. I have two pairs of earrings in each lobe, and am wearing two silver rings on each hand along with many bracelets and a black choker around my neck to disguise the unfortunate bump on my throat! My toenails are all covered with a beautiful silver colour, and my fingernails are all a pastel pink colour.

Happy with my underwear and make-up all sorted, I roll a pair of dark patterned tights up my legs until they're smooth from my waist to my toes, and step into a dark blue denim miniskirt, the flared hem of which ends about six inches above my knee. I pull on my favourite khaki top, which hugs my entire body beautifully and showsoff my womanly curves at their best. Of course, I pull down the shoulders to expose my black bra straps, hehe! I step into a pair of black, 3" heeled ankle boots and my transformation is complete. This is the first time I'll ever have been dressed in front of another person- even someone I know to be as understanding as Paul is- but still, I'm a little nervous. I take one final moment to spray on some perfume and check my lipstick one more time, before stepping out and facing the young student. I stand in front of the gobsmacked young man, one hand on hip, and ask him one simple question.

"Well?" I ask with a pouty smile on my lips.

"Wow," Paul responds, genuinely speechless, "you said you thought you looked convincing but you look... beautiful!" I blush a little and motion for the two of us to sit down on my bed.

"No I don't," I say coyly, "I've just had a lot of practice with make-up, that's all." Paul simply smiles and gently pats my nylon-covered knee.

"I think I know a pretty girl when I see one," he says, smiling and looking me in the eyes. Is he flirting with me?

"You're comfortable viewing me as a girl, as Debbie, then?" I ask, keeping my legs together and folding them underneath me on the bed.

"The way you look right now, Debbie," Paul responds, "I'd have trouble viewing you as anything else! You're just- wow!" I blush a little again and brush some of my long hair out of my face. "How long have you been dressing?" Paul asks me matter-of-factly.

"Ten years," I reply. "I first started trying on my sister's school uniform, then some of her other clothes, her gymnastics and ballet uniforms, eventually she moved out and got rid of a lot of stuff, I just happened to be in the right place at the right time and I inherited almost half a complete wardrobe!"

"All this you're wearing now used to be your sister's?" Paul asks.

"Only the top and the boots" I reply honestly. "The skirt and the underwear I ordered off the internet, and the make-up and jewellery is all mine too."

"You're obviously committed to this lifestyle then, have you ever thought about becoming a girl full-time?" Paul stuns me with that question- of course I'd love to be a girl full-time, but I'd never seriously considered it a genuine possbility. The way he's talking though, it's almost as if I could become Debbie tomorrow! I subconsciously straighten the hem of my skirt and smooth my tights before answering- two actions that have become such second nature to me, I genuinely miss them when wearing my boring boy clothes.

"I wish I could be Debbie all the time," I reply, "but I just don't think I'm brave enough to, not just yet anyway." Paul nods quietly.

"I understand," he says seriously. "If you ever want to make the transition, of course the society will help you, and more importantly, I'll give you my full support." He places his hand on me in a friendly gesture and I smile again. Could I really become Debbie full-time, live my dream? I could maybe afford it with my mother's help, but how would she, a devout Catholic, respond?

"Thanks," I say quietly, before slowly leaning closer and giving Paul a small kiss on the cheek. I've never kissed a man before (I deliberately didn't write "another man" there for obvious reasons), not even on the cheek, but it just feels so... right. A moment passes between us where we look into each others' eyes, and before I know it, Paul is softly kissing me on the lips. I close my eyes and soak up every sensation I feel, from the softness of his lips on mine, to the gentle embrace of his hands around my body.

"I'm sorry, I shou-" Paul says before I cut him off with a finger on the lips.

"Don't be sorry," I say, before we share another long, passionate kiss. I can feel myself begin to melt into his strong arms as our embrace becomes ever more erotic, him slowly stroking my nylon-covered thigh, advancing ever deeper underneath my skirt as I slowly begin to stroke his stirring groin underneath his jeans. Both our bodies are covered in a fine sheen of perspiration as he begins to stroke my crotch, eliciting slight yelps of desire from me. He starts kissing my neck as he rubs my pseudo-vagina ever harder, causing my eyes to roll back into my head as I gasp with desire. Before too long, my orgasm comes and so do I, bucking in Paul's arms as I thrust repeatedly against his hand. Once I am done, I look deep into his gorgeous eyes.

"Thank you," I say, kissing him fully, then licking my lips. "Fair's fair, I suppose," I say cheekily, before sliding off the bed and onto my knees. I unzip his fly and take his ever-swelling lad into my slender, girlish hands.

"You don't have to," Paul says quietly, although deep down, I know he wants me to.

"I want to," I whisper, gently kissing the engorged head of his penis, and slowly guiding it, inch by inch, into my mouth, treating it to licks and sucks every inch of the way. I close my eyes, savouring the taste of my first penis. Before too long, I feel Paul begin to swell immensely within my mouth, stretching my lips uncomfortably and touching the back of my throat with his glans as he comes, shooting his hot load into my mouth and down my throat. I moan softly as I swallow every drop of his seed, my own spent lad tingling with excitement inside its silky prison. I suck the last drops of semen of the head of his penis as he withdraws from my mouth, before looking into Paul's eyes, swallowing, then licking my lips and giving him another long, sloppy kiss.

"Wow," Paul says breathlessly, "I think I'm in love!" I simply laugh and wrap my arms around him, resting my blonde head on his shoulders. I think I have a new boyfriend!

  

  

  

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