by D. L. Savage
So I took a deep, shaky breath, then picked up my cell and began to dial his number ...
9
“Amy, hi!” Michael’s warm voice filled my ear, and I felt another shiver of excitement and anticipation. “I’m glad you called. Are you checked in?”
“Sure am,” I replied in my softest, most sexiest voice, hoping the tremble of nerves I felt in that moment weren’t audible. “So, you still wanna meet for a drink in the bar later?”
“I was about to ask the exact same thing,” he laughed. “Shall we say nine o’ clock?”
I glanced at the clock on the wall. It was a little after seven.
“Perfect,” I said, still unable to believe I was actually going through with this. “See you soon.”
I quickly hung up the call, scared I would say something stupid – sound too keen or put him off somehow. And the truth was, I felt nervous and excited as any date I’d ever been on. Even more so, perhaps, because this was different.
It was like I’d started all over again in some brand new alternate reality. I felt like a nervous teenager, about to go on her very first date ...
After a quick shower and another shave, just to make sure there was no hint of stubble on my face, I began to dress.
I’d chosen the g-string of course, and I just hoped to hell it would keep my cock and balls contained, as I didn’t want to show any kind of lumps or bumps. I slid the flimsy little thing up over my legs, then tugged the waistband right up around my waist, the string at the back slipping between my butt cheeks and – thank God – the gusset cupping my balls and cock really nicely.
It was actually even tighter and more snug than the thong; just perfect.
Next I rolled on the stockings, one by one, adjusting them at the tops of my thighs until they were both level and sitting nicely.
As I dressed myself, I felt my body slowly suffusing with a soft, sensual pleasure. I felt so good, so girly, so sexy, and I just couldn’t wait to see myself in the mirror again. But first I had a lot more work to do.
I pulled on the bra, clipping it around my waist, shuffling it up, then adjusting the fillets once again until they were sitting nicely in the cups.
And then, before I checked myself out in the mirror, I slipped the shoe box out from the bag and lifted the lid, gazing in excitedly at the glossy black heels, laying there in their bed of crumpled pink tissue paper.
A little vial tumbled out of the bag too and I smiled, as I remembered that as I’d headed back through the department store, a girl at the perfume counter had offered me a free sample to take home with me.
Perfect!
I undid the lid of the vial and dabbed the perfume carefully onto my wrists, then patted them against my neck too, just like I’d seen girls do in the past.
The sweet, floral scent was delicious, and I breathed it in happily as I lifted the heels out of their box, then slipped them onto my stockinged feet one by one, before pushing myself up to standing.
Whoa!
I almost lost my balance; this was way different to a pair of sneakers. I almost felt like I was standing on a set of stilts or something. But after a few tentative steps, I found I got the hang of it, and began strutting up and down the hotel room, all the while keeping in mind what Amy had taught me – head straight, shoulders back, small steps, swing your hips. And actually, if I walked like that it soon fell into place.
I headed over to the mirror, again excited to see how I looked, and holy shit, I felt a deep thrill flash through me when I finally set eyes on my reflection.
The whole effect – the heels, stockings, g-string and bra – screamed SEX.
I turned around, checking out my butt, loving the way the tops of the stockings and the thin black g-string accentuated it, and I couldn’t help but bend over a little and give my booty a little jiggle, feeling a tingle of sexual excitement running through me at the sight of my own sexy reflection.
I could feel my cock starting to swell and strain, but to my surprise and relief, the panties seemed to keep it totally contained. All that showed now was a tight round bulge in the front; one that I hoped wouldn’t show through the black dress, should I get turned on while I was out.
The only thing missing now, I realized, was to transform myself from the neck upwards.
My hair extensions had stayed put and I’d been careful not to get them wet under the shower. I figured with my hair, all I’d need to do was tease it and plump it a little and it’d look good – it was still shiny and glossy, long and blonde, after all.
Yes, all that was left was my face ...
I put the finishing touches to my lipstick, just like the girl on the YouTube video playing on my cellphone instructed, then set the small compact mirror in my hand down and skittered excitedly once more to the large wall mirror near the bathroom to see the full effect.
Wow. I’d actually done a pretty good job!
The tutorial I’d followed was a for a ‘smoky, sexy nighttime look’ and it was perfect. Big red lips, contouring, and of course dark eyeliner and mascara, really making my eyes stand out.
I’d learnt so many tricks and tips already and found I was seemingly a natural at applying the makeup to my face without making many mistakes. There was so much you could do, just with a little powder and lipstick – accentuating the size of your lips by subtly painting past their edges, making your nose look slimmer with a few subtle brushes of dark powder ...
I was finally ready. Ready as I’d ever be.
I looked at the wall clock.
Fifteen minutes to go – just enough time to grab a drink of something strong from the mini bar in my room, to steady my beating heart a little. I couldn’t believe I was actually going through with this, but at the same time I felt so damn excited – nervous and charged with energy in a way I don’t think I’d ever been before.
All thoughts of the presentation were totally gone from my mind now.
My focus was solely trained on tonight.
On what could quite possibly be the most exciting night of my life ...
10
Maybe I was just imagining it, but as I stepped into that amazing art deco bar, complete with plush red carpets and glittering chandeliers hanging from the ceiling, it felt as if every eye in the room turned to watch me.
I’d never felt more feminine, more glamorous, more beautiful than I did in that moment, as I strode confidently into the room, my long blonde hair flowing, the little black dress accentuating my curves, my cock held tight and snug by the g-string, the shiny black heels and stockings making my legs look longer and sexier than ever before.
And when I set eyes on Michael, who was sitting at a table in the far corner of the room, I felt my glossy red lips curl into a playful smile.
He smiled too, his white teeth flashing, as – just like a gentleman – he pushed himself up from his seat as I arrived, leaning in and placing a hand gently on the small of my back as he kissed me on the cheek.
“You look amazing,” he murmured, sending another thrill right through me.
“You don’t scrub up too bad yourself,” I teased, batting my eyelashes at him as we both sat down again – me making sure to cross my legs daintily, and keep my poise the whole time, back arched, shoulders back, head up.
It was true. He really did look amazing, too, even better than in my memory. He was wearing an expensive looking pale blue shirt, unbuttoned at the collar to give a glimpse of honey gold skin beneath, and dark slacks, and again I found myself getting excited at simply how much bigger and more masculine, more powerful he was than me.
“Shall we get a bottle of wine?” he asked. “You like white wine, right?”
“Wine would be lovely,” I replied softly, feeling my heart quicken as his eyes locked onto mine; again there it was, that playful suggestive tone in his voice, that flirtatiousness beneath what he was saying, that confirmed all over again that his was definitely, without question a date.
I sat back, enjoying the way Michael to
ok the lead, watching impressed as he flagged down a waiter, then asked for a bottle of Marlborough Sauvignon Blanc and two glasses.
“Very good, sir,” the waiter said politely, leaving us alone once more.
I wondered what we looked like to that waiter; just a regular couple, out on a date, perhaps?
“So how was your conference so far?” I asked, just trying to make conversation.
“It actually starts tomorrow,” he grinned. “I’ve just spent the afternoon hanging out in my room. If I’d had your number, I might have asked you to come over, keep me company ...”
Woah, this guy is a fast mover, I thought. Because there was no way of misreading what he really meant ...
And the thing was, I didn’t mind – in fact, I was enjoying the hell out of it.
“I might have said yes,” I purred back, trying to make my voice as sexy as possible, as beneath my dress, I could feel my cock starting to throb in my panties, aching and straining against the tight confines of the g-string.
“Say,” Michael continued, leaning into me now, his voice dropping to a low taut growl, “why don’t we take the wine up to my room?”
I felt my stomach lurch. This was moving so fast it was crazy. But as I gazed at him, I knew that I wanted it, wanted it so fucking badly ...
“Sure, that sounds fun,” I heard myself say, just as the waiter returned with the chilled bottle of wine and two glasses.
“Actually?” Michael said, looking up at him with a charismatic grin, “the lady and I are heading up to my room. It’s six fifty one. If we could have the wine delivered there and charged to my account, that would be great.”
Again, the waiter was the picture of professionalism, not batting an eyelid as he said, “Very good, sir, madam,” then once more left us alone.
“Well, Amy,” Michael smiled, standing up and offering me his arm, “shall we?”
I felt myself shiver a little from the sheer nervous excitement that flowed through me as I pushed myself up to my feet, then slipped my slender arm through his, the two of us making our way out through the bar, towards the elevator ...
11
The brushed chrome doors to the elevator had barely closed before he leant in towards me, my senses filled with the delicious spice of his cologne, as he crushed his sensuous lips against mine, plundering my mouth with his tongue, his hands moving to my sides.
I moaned into his mouth, totally lost in the kiss, which was like nothing I’d ever known. I felt so small, so powerless, so feminine compared to him. He was taking complete control, dominating me, and all I could do was give myself up to it, my slim body trembling as he pushed me against the wall of the elevator, the distinct hot hard bulk of his cock pushing against my belly through his slacks and my dress.
“I’ve wanted to do this since the moment I first set eyes on you,” he growled between kisses, his hands now moving to my ass, drawing me even closer toward him.
Just then, the ping of the elevator signaled the fact that we’d reached his floor, and we both pulled away, Michael taking my hand as he led me to his room, my heart booming so hard by now I felt like it might jump out of my chest at any moment.
And again, the very moment we’d set foot in his room, he pushed against me, kissing me hungrily and me kissing him right back, shivering and trembling, totally lost in pleasure.
“I want you so fucking badly, Amy,” he growled, his voice tight with lust, his hand starting to push up beneath my dress ...
And it was only in that moment that I wondered what the fuck I was going to do. What was I thinking? If he touched me there he’d find out my secret! ... How in the hell was I going to let this go any further without him discovering who – or what – I really was ...
But luckily just then, there came a loud knock on the door to his room and we both broke away again.
“That must be the wine,” he smiled, his voice breathless from our kiss.
As he went to receive it, I turned away, quickly adjusting my dress again, and checking that my now rock-hard cock wasn’t making a huge bulge. To my surprise and relief, the panties and stretchy fabric of the dress were still holding it tightly in place, and as long as he didn’t actually touch me there, my secret remained safe. For now.
I padded over to the edge of his bed, which was just as big and sumptuous as the one in my room, and sat down demurely, tucking my cock down between my thighs and adjusting my hair a little, then gazing at my own reflection in the wall mirror, glad that I still looked totally real – totally feminine.
Michael brought in the chilled bottle of wine and poured us out two glasses, then strode over to where I was sitting, handing me a glass, remaining standing in front of me as he sipped from his, those dark eyes blazing down at me with pure lust.
I took a long, slow sip, trying to calm my trembling nerves, then looked up at him, feeling my heart boom as I realized just what I was going to do next.
Without saying a word, I reached out and set my glass down on the side table near the bed, then took Michael’s from his hand and did the same.
And then I began to unbuckle his belt, drawing him closer to me in the process, so that he was standing only inches from me now, his crotch right in line with my face.
I’d never ever had gay or even bisexual thoughts, back when I was Adam. But this was different. I was Amy now – a sexy, coquettish minx with only one thing on her mind ...
“Oh, is that what you want?” he growled, as it became clear just what was happening.
I nodded, gazing up at him with my big blue eyes and a naughty grin on my face, before returning my attention back to what was right in front of me, tugging open his belt with shaky fingers and then unzipping his slacks, uncovering a pair of dark silk boxer shorts beneath, the hard bulk of his cock already straining through them.
I inched the waistband down slowly until I’d uncovered him, setting eyes on his cock for the first time – and holy shit, it was perfect. Thick and hard, with a slight upward curve, the shaft smooth and golden, the head slick and pink, his balls round and shaved, with just a dark fuzz of neatly cropped pubic hair above his shaft.
I felt a deep charge of excitement as I gazed at it, my own dick throbbing and aching between my crossed thighs as I reached out and took him tentatively in my fingers, gently stroking him the way I liked my own dick to be stroked, my thumb starting to tease the sensitive underside part just beneath the head that I always focused on while masturbating.
It seemed to work; Michael let out a deep groan of pleasure, his body tensing and his eyes closing as I continued to stroke him.
But soon, merely stroking wasn’t enough. As I jacked that big, gorgeous dick, I just knew I had to taste it too.
I felt my body suffusing with a sensuous, nervous energy unlike any I’d ever known as I leant in, parting my lips and closing my eyes as guided it towards my mouth. And as I finally clasped my lips around his hot, thick shaft, feeling the silky head gliding against my tongue, my whole body seemed overcome my a tidal wave of pure emotion, enough to make me shiver and moan with pleasure.
I began to suck him, tenderly at first, exploring his thick hard cock with my lips, tongue and hands – sucking him deep, then letting my lips pull away with a pop, then sucking again, teasing the head with my tongue, taking him deep again, then shallow, all the while jacking his shaft with one hand and cupping his balls with the other.
I even began rubbing the head softly against my lips and outstretched tongue, just savoring the whole sensation of worshipping that big, perfect cock, and Michael seemed to be totally lost in the moment too, each breathy groan he made spurring me on, each sigh like a little prize, knowing I was bringing him just as much pleasure as he was bringing me right now.
I felt totally feminine, totally slutty, totally devoted to him in that moment, and I just wished I could suck him forever, or at least to feel his hot load in my mouth.
But after a while, I felt his hands gently resting on my shoulders, drawing me away ag
ain. I looked up, puzzled, and the expression on his face told me immediately that he wanted more.
“Take off your dress,” he growled.
I froze, my eyes widening, knowing that I couldn’t – knowing that if I did, he’d find out the truth. After all, my cock was rock solid now, ready to burst from my panties the very moment I set it free from the tight slinky confines of the dress.
And then what?
With a jolt of sadness, I knew my fun had most likely come to an end and I had only two options remaining – either tell him the truth, or make my excuses and leave.
And he’d already given me so much pleasure, it felt wrong somehow to just fuck with his head and go without an explanation. In that moment, I knew I owed him the truth, at least, even if it would disgust him.
So I took a big, shaky breath, then said the words.
“Michael, before we continue, I think there’s something about me that you should know ...”
12
“What?” he said, totally confused, his rock hard dick still jutting up, throbbing mere inches away from my face, bathing it in heat. “What is it?”
“Well,” I stammered, hearing my voice shake a little as I tried to find the correct way to say it, “I’m ... uh ... I’m ... transgender.”
There. I’d told the truth – or at least a version of it that Michael would understand.
An odd look flickered across his handsome features, but to my surprise it wasn’t one of total disgust like I’d been dreading. Instead, it looked more like ... curiosity.
“You mean you have a ...” he murmured, nodding down at his own dick, which was still just as rock hard and throbbing as before.