Debbie at 19

by Debbie Valentine

 

I gasp as the corset bites ever deeper into my figure, adding another half-inch to the five already trimmed off my increasingly-girlish figure. Beneath the corset, my frivolously tiny g-string does its job in subduing my squirming lad and not betraying even the slightest hint of its presence, whilst simultaneously providing me with erotic sensations as the thin lycra strap rubs up against my virgin arsehole. My red-painted toes wiggle in their dark silk stockings, attached by four garters each to the corset that my friend is mercilessly yanking ever tighter. My C-cup breasts, which are held in place by both theatrical glue and a strong strapless bra, heave as my entire figure alters under the embrace of the foundation wear.

My name is David Vincent, or as I like to be called when I'm dressed the way I am right now, Debbie Vincent. I am a 19-year old transvestite, and tonight is mine and my boyfriend's 3-month anniversary!

"If we go any further you'll run the risk of passing out mid-meal!" Naomi, the friend helping me with getting ready for the evening, informs me. Naomi, a gay member of the university's LGBT society, is one of David's best friend and, as Debbie, is one of only four people who know about the "real me".

"Okay, it'll have to do," I say in my feminine Irish accent, which I have been perfecting over the past few months with Naomi's help. "What's my waist now?" I raise my arms as Naomi wraps a tape measure around my slender waist.

"25 inches," I'm told. "You need to diet more!" The young woman teases me as I sit down and begin putting on my jewellery for the night.

"After tonight," I joke back, wrapping my black choker around my neck to disguise my adam's apple, and putting on a pair of pearl drop earrings my boyfriend gave me for my birthday last month.

"Lobster goes straight to your arse, you know," Naomi teases again as she begins to apply my make-up- delicate pink eyeshadow and some thick mascara, as well as a modest amount of blusher and a liberal coat of deep red lipstick. My curled blonde hair is pinned up atop my head, and as I slip my four rings onto my red-tipped fingers and clip my gold bracelet onto my wrist, I feel, and look, just like a movie star going to a premiere.

Of course, I'm only going to my boyfriend's room for a quiet meal, just the two of us, but the one thing I'd requested was that it be as formal a meal- dressing up, full waiter service, the lot, and a couple of our friends in the LGBT society (which Paul is the president of, helpfully enough!) were only too happy to help out!

I stand up, still feeling a little embarrassed about the cold air meeting my bare buttocks, and head over to where my knee-length strapless red dress is being held out for me to step into. I step into it fully and Naomi pulls it up my body, zipping me in tightly so that the dress's elasticity holds it tight against the top of my breasts and close to my corseted waist, whilst not showing the outline of any of my underwear. I slip my feet into a pair of 4.5" heeled red stilettos, grab my matching red handbag, and my look is complete. After I pose for a few photos for Naomi (for her own personal website), we head down the deserted corridor toward our "restaurant", aka Paul's room.

"I hope Paul gets the message you're sending to him," Naomi teases as she walks with me (she's also our 'waitress' tonight).

"What message is that?" I ask back, smiling at the playful teasing.

"Fuck. Me. Hard," Naomi says, sticking her tongue out at me. I stick my tongue out at her in response, but I don't deny her accusation!

As I mentioned before, I'm still a virgin- I have no interest in heterosexual intercourse, nor do I wish to penetrate anybody female or male. Paul is my first real boyfriend, and he has still not yet taken my 'cherry'- but three months on, tonight could be the night! Especially as I have a small tube of lubricant stashed in my handbag!

We arrive at Paul's room, and I enter to a breathtaking sight- the lights are down low and romatic music is playing. His normally cluttered room is clear save for a single table, two chairs, and a single candle in the centre of the table.

"Oh Paul," I say breathlessly, "it's beautiful!" Paul comes over to me and gives me a loving kiss on the lips.

"Not as beautiful as you are, Debs," he says softly as he guides me into my seat.

"It's perfect," I whisper. Paul takes his seat opposite me, and we hold each other's hands and look into each other's eyes for one brief, perfect moment, before we are interrupted by our 'waitress'- Naomi having quickly changed into her black maid's dress (which I'm actually lending her for the night, hehe!).

"May I take your order sir, madam," Naomi says, dropping into a small curtsey as she reaches our table.

"The clam chowder for me," Paul says without hesitation, "and the grilled lobster for the main course."

"Thank you sir," Naomi says, before turning to me. "And for madam?" I smile at being called 'madam'- even though Naomi sees more of Debbie than she does of David, it's still 'validation' in my eyes!

"Ths same," I reply.

"Thank you, madam," Naomi says, curtseying again. "I shall bring your starter shortly." Naomi quickly sashays off to the kitchen, leaving me alone with my Paul.

"You know," I say with a naughty smile on my face, "seafood's supposed to be an aphrodisiac. Between the food and the wine, I'd swear you were trying to take advantage of me!" Paul simply grins slyly in reply.

"Where would you ever get an idea like that from?" He says with a hidden chuckle in his voice.

"Oh, I don't know," I say, trying to sound innocent and pure (and failing!), "maybe the way you can't keep your eyes off of my round, juicy bottom?" Paul licks his lips at the thought of my bottom, and I lick my lips at the thought of the erection he almost certainly now sports. I'd love nothing more than to be under the table right now, sucking all nine inches of Paul's lad down my throat as I have done many times before- I don't want to ruin my appetite ahead of our meal, though!

Before Paul can respond, our starter is brought through, and we both gleefully begin gulping down the chowder, only pausing briefly to make 'kissy faces' at each other (me more than him).

We talk and flirt a little more until our lobster comes, which we both eat with gusto- not so quick as to give ourselves indigestion (especially not when I'm still tightly wrapped into my corset!), but we both want to get past the meal and to the real anniversary celebrations!

I smile wickedly as our desserts, chocolate truffles, are placed down in front of us.

"Truffles?" I ask with the same wicked smile still on my face, "now I KNOW you're trying to take advantage of me!"

"Maybe you want to be taken advantage of," Paul says, smiling his own seductive smile back.

"Maybe I do," I say, picking one truffle up with my fork and eating is s-l-o-w-l-y, watching Paul try to resist the urge to drool. I lick the residue of the truffle off my lips as Paul begins eating his dessert.

This "flirting duel" carries on throughout the entire dessert until the truffles are all gone, and the two of us are covered with a fine sheen of sweat- I can't speak for Paul, but I for one am horny as hell! Once our plates are cleared away, Paul goes over to Naomi and hands her something- she (and our chef) quickly leave the room, leaving me alone with my wonderful boyfriend in his apartment. I stand up and we slowly walk toward each other, still breathing heavily, still desperate for each other's bodies.

"Thank you for tonight," I whisper, barely able to make an audible noise with my deep breathing- not helped by my corset, of course!

"Who says tonight is over yet?" Paul asks, placing his hands on my svelte waist.

"Not me," I whisper, wrapping my arms around Paul's neck and giving him a deep, passionate kiss.

Before I know what's happening, I have lost my dress, shoes and bra and Paul is down to his underpants, both of us passionately embracing as we roll around on his double bed. He is rubbing my groin and breasts with his hands, whilst I am slowly massaging his lad inside his pants with mine. I quickly reach my first orgasm, thrusting against Paul's fingers as I did three months ago, when we first met. As my climax subsides, I free Paul's lad from its fabric prison and give it a couple of longing kisses, licking and sucking to ensure he stays 'stimulated', before smiling wickedly and turning around, pulling the thin strap of my g-string aside and seductively wiggling my round, juicy bottom at him. Instinctively, Paul wraps a condom on his penis, then applies some lubricant to his fingers and, whilst gently kissing my neck and massaging my breasts, penetrates me one finger at a time.

I gasp at the sheer eroticness of the stimulation- I've poked fingers up my arse before, but what Paul's doing, masturbating my prostate, is something I've never experienced before. I gasp and pant as he slides three fingers in and out of my arsehole, before removing them entirely. I pout for a second, unhappy that he has withdrawn, but I suddenly gasp loud as the head of his rubber-sheathed lad slips easily inside me. The lubricant was cold, but the condom is even colder- and it's delving deep within me, deeper than Paul's fingers could ever reach.

My vision begins to go blurry as Paul thrusts deep within me, driving his lad deeper into my arse with every movement. I can tell he's nearing his own orgasm as he speeds up, rubbing my anus and causing me to have my second orgasm of the night. As I climax, my anal muscles contract hard around Paul's lad as he pushes himself into me to the hilt, when he stiffens and begins to come inside my anus.

I scream loudly as my own orgasm is accompanied by Paul battering my anus with his rubber-covered penis, shooting load after load. My vision fades as my orgasm fades, and the last thing I remember is Paul placing his arms around my waist and kissing my neck gently, over and over, as he withdraws fully from my anus.

I wake up the following morning with my head rested on my gorgeous boyfriend's gorgeous chest- still adoring the feeling of my chest being adorned with the weight of my false breasts, the constriction of the corset around my waist and my silk-covered legs rubbing against each other (as well as Paul's legs!), but now I have a new feeling to enjoy- the tingling and the slight soreness in my arse tells me that last night, more than any other night previously, I was a woman, and I did what a woman does in bed with a man.

I sigh and kiss Paul's chest with my full red lips- if last night was anything to go by, tonight's going to be amazing!

  

  

  

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