Feminized for the Very First Time: 8 Books Feminization Anthology

by D. L. Savage

  6

  It was only a two and a half hour flight to Boston, and after reading through the pitch script a few more times, I set it down on my lap, relaxing a little in my comfy spacious seat, closing my eyes as the words I’d rehearsed so many times went floating through my head.

  “Drink, sir? Drink, madam?” the soft voice of the air hostess chimed in my ear, breaking me out of my thoughts, and I opened my eyes to see the same pretty girl who’d welcomed me onto the flight now standing with a drinks cart, brimming with cold soda cans, mineral water, juices and even alcoholic drinks – beer, and individual-size bottles of wine.

  “Please, ladies first,” the warm low tone of the businessman next to me said, and I felt another weird shiver of delight at the idea that he really thought I was a girl.

  “Thank you,” I murmured, shooting him a quick shy smile and catching another glimpse of his dark handsome face in the process, an odd jolt of excitement going through me, before I quickly turned back to the stewardess, still deliberating over whether or not to get something a little stronger than a soda.

  I knew I should probably keep my head clear for the presentation tomorrow, but at the same time the allure of free alcohol was almost impossible to resist.

  “I’ll take ...” I began, willing myself to say soda, but instead the words, “a glass of white wine please,” fell from my glossy lips.

  Ah well, I told myself, one little drink won’t hurt.

  “And for you, sir?” the hostess asked the guy next to me as she poured out my glass of chilled white wine and set it on the little table next to my seat.

  “I was going to say coffee,” he laughed, “but that wine looks so good, I’ll take one, too!”

  I found myself giggling too, partly because I found it funny but also because I wanted to flirt with him a little. It was crazy, but a part of me really was enjoying this whole episode in a way I’d never even imagined.

  “Cheers,” he smiled at me as the hostess passed him his glass and then wheeled her trolley off down the aisle.

  “Cheers,” I grinned back, clinking my drink against his, then taking a small delicate sip, hoping the liquid didn’t screw up my lipstick somehow. Surely it wouldn’t? I’d seen girls drink wearing makeup before and it seemed fine. But I felt a tiny flash of girlish glee when I brought the glass from my lips and saw I’d left a lipstick mark on the rim, just like a real woman.

  “I’m Michael, by the way,” he said, still smiling at me.

  “Amy,” I replied, trying to make my voice sound as soft and feminine as I possibly could, hearing the name purr past my lips in barely more than a sultry, sexy whisper.

  “So what brings you to Boston? Anything fun?” he continued.

  I felt my heart starting to drum a little as he trained his big brown eyes on me, my own gaze drawn for a brief half-second to his full sensuous lips, lips that looked so ... kissable.

  What the hell was I thinking?!

  “I’m, uh, actually there on business,” I replied quickly, looking away shyly. But it was like this guy was a magnet, and soon I found my gaze drawn back to him, as I added, “I’m pitching for a contract at some tech firm. I’m a graphic designer.”

  “Cool!” he smiled. “I thought you looked like an arsty type.”

  Again I felt a little shiver of excitement, this time because I recognized – not in the words themselves, but in the way he was saying them – that he was flirting with me, too.

  “How about you, Michael?” I said, my confidence picking up, as I found pleasure in throwing his name in, letting it fall from my lips in a sexy, teasing tone. “Are you doing anything fun in Boston?”

  “I wish,” he smiled back, shifting a little closer to me in his seat, again making me realized just how big and muscular, how full and strong his body was in comparison to mine. “I’m spending my whole weekend at some boring ass conference.”

  “That’s too bad,” I grinned.

  “Ah, it’s okay,” he replied. “By now, I’m pretty used to hotel rooms. Say, where are you staying?”

  I scanned through Amy’s printed out itinerary that was sitting on my lap, “The ... um ... Langham?” I said, once I’d found the hotel information.

  “No shit!” he laughed. “Me too!”

  I found myself laughing right along with him, until a moment later he added, “Well, Amy, if you’re at a loose end this evening, perhaps we could have another drink together in the hotel bar?”

  The shot of excitement I felt in that moment took me totally by surprise, and I even found myself blushing a little.

  Holy shit. I just got asked out. By a guy.

  What’s more, it fucking turned me on.

  “I’d like that, Michael,” I heard myself say, in the same soft, sexy voice as before, my hand shaking just a touch as I lifted my wine to my lips and took a long, slow sip.

  “Great,” he smiled back. “Here’s my number. Just call me, I’ll be in my room all evening.”

  And with that, he reached into the breast pocket of his perfectly tailored suit and pulled out a fancy-looking cream business card, handing it to me.

  “I will,” I smiled back, slipping it into the sheaf of documents on my lap.

  “Well, I guess I’d better get on with a little work,” he said, somewhat apologetically, taking out a document case of his own. “But I’m looking forward to tonight,” he added with a smile.

  “Me too,” I grinned back.

  As he settled down into his seat, I felt a fresh rush of excitement, mixed with total confusion, too.

  What the hell was I doing?

  Had I really just agreed to go on a date ... with a guy?

  But most of all, I felt pleased; pleased that again I’d fooled someone into thinking I really was a cute, sexy girl. With a naughty smile playing on my lips, I once more tried to read over the pitch script, but now I just couldn’t concentrate ...

  7

  “So?” Amy croaked on the other end of the phone, as I was waiting to collect my suitcase in the baggage area. “How did it go? Did you make the flight okay?”

  “Everything went fine,” I assured her, “don’t you worry. They all think I’m you. You’re crazy plan is actually working.”

  “I knew it would!” she laughed back. “So once you’re at the hotel, why don’t you give me another call? I thought maybe we could rehearse the script again a few more times?”

  “Amy, don’t worry,” I assured her, “I’ve been going over it all flight. I know it, just relax, okay?”

  “Well, make sure to get a good night’s sleep,” she said, her strict tone of voice reminding me a little of of our mom.

  Just at that moment, I caught sight of Michael over at the other side of the baggage claim, lifting his suitcase off the conveyor belt. I’d stepped a few feet away from the crowd so nobody heard me talking on the phone in my normal guy’s voice, but even so, I felt a pang of worry that he’d somehow heard me. But as his eye caught mine, he flashed me a big grin and I felt that weird excitement bubbled up inside me, at the idea of our date later.

  I gave him a quick wave goodbye, then said, “Of course I will, don’t worry.”

  “Okay, well good luck for tomorrow,” Amy said. “And call me if you need anything ... Oh and Andy? Enjoy the hotel! The tech company paid for it and it’s supposed to be pretty fancy.”

  “Cool,” I laughed. “I will.”

  Just then I caught sight of Amy’s suitcase coming around on the carousel.

  “Hey, I’d better go,” I told her. “I’ll let you know how it goes tomorrow, just as soon as the presentation is over.”

  “Good luck,” I heard her croak, just as I hung up the phone, then dashed for my case, again feeling the strange sensation of my long hair dancing around my shoulders and my breasts bouncing beneath my sweater as I moved.

  As I leant in to lift it off the carousel, for a half-second I even felt self-conscious about the thought that my thong might have been showing from over the top of my le
ggings; the kind of thing a real girl might worry about.

  With a wry smile, and shaking my head once again at the crazy situation I’d ended up in, I grabbed the handle of the case then began to wheel it out of the airport, towards the taxi rank.

  Amy wasn’t exaggerating. As the taxi pulled up outside the Langham hotel a short while later, I almost couldn’t believe my eyes.

  Holy shit, I thought, as I took in the glitzy doorway, complete with flags flying above and immaculately suited doormen on either side.

  I tipped my driver, then got out of the cab while he dutifully took my case from the trunk. And before I’d even had a chance to touch it, one of the doormen was wheeling it through to the lobby for me, murmuring, “Please, allow me, madam.”

  The lobby was even more impressive, with a gleaming polished floor and cool art deco furnishings. I strode up to the reception desk, where a smiling older gentleman greeted me.

  “Good afternoon, madam,” he said in a soft voice. “Are you staying with us tonight?”

  “I sure am,” I smiled back, my Amy voice coming so easily to me now it was almost like second nature. “There should be a reservation for Amy Williams for tonight?”

  He checked on the computer database, then smiled and nodded, saying, “I can see that’s all been paid for in advance, Miss Williams. Here is your keycard, and one of our assistants will show you up to your room at once.”

  He made a gesture, and a moment later a young guy, no more than eighteen came bounding up.

  “Josh, could you please show Miss Williams up to room 463, please?” he said, and Josh grinned and nodded, taking my case and leading me over to the elevators.

  As we stepped inside and he punched the number for my room, I could feel a strange tension developing, which I realized was nervousness – not from me, but from him. Josh was obviously checking me out from the corner of his eye, his gaze flitting from the small bumps of my breasts, then down to my legging-clad thighs, and back again.

  I knew that feeling so well – how many times had I checked out a hot girl, thinking she wasn’t watching? But it turns out, you really can tell when a guy is giving off such clearly horny vibes, and Josh wasn’t being half as covert as he thought he was.

  A naughty little grin flickered across my lips, as a silly thought flashed through my head.

  Maybe I should have a little fun with him ...

  As the elevator rose upwards, I slipped my hands beneath the hem of my leggings, until my fingers found the waistband of my thong, then I tugged it up at the back, just a little, until I was sure I was showing off a touch of whaletail.

  Just then, the elevator pinged, and the chrome doors swished open, revealing a plush, silent corridor beyond, way more fancy than any hotel corridor I’d ever been in.

  “This way, please, Miss,” Josh said in a slightly nervous voice, taking my case and leading the way to my room.

  He fitted the keycard into the slot, then pushed open the door, handing the key back to me as I stepped inside, wheeling my case after me. And just as I’d taken a few steps into the room, I purposefully let my purse slip from my arm and fall onto the carpet, my back still to him.

  “Oops!” I giggled, as if it was a complete accident, then as gracefully as I could, I bent forward to pick it up, arching my back, my long blonde hair falling in my face, as I pushed my butt out towards him, feeling the sweater riding up around my waist, uncovering my ass with that sexy purple thong on full display.

  I grabbed the purse, then stood upright again, turning around to him with a happy smile as if nothing at all had happened, rooting around within the purse for a few bills for a tip.

  “Thanks for your help, Josh,” I purred, handing him the notes, my eye flicking down to his crotch for a half-second, and sure enough, I could see the outline of a boner, straining against the fabric.

  “Don’t mention it,” he murmured, his face beet red as he quickly took the money then turned and raced out of the room.

  I closed the door behind him, strangely satisfied with the naughty little game I’d played.

  Then I looked at the room properly for the first time. It was insane. The biggest, fanciest hotel room I had ever been in, complete with a huge double bed, giant flat screen TV, balcony, and a glitzy gold and cream themed en-suite bathroom. But my eye was drawn to something else.

  A huge floor-to-ceiling mirror by the bathroom door.

  I strode towards it, excited to see my full reflection again for the first time since my hurried morning getting ready in Amy’s bedroom. And when I set eyes on myself, I was knocked back again by just how real – how convincing – I looked. There was not a hint of my former self. All I saw in the mirror was a slim, sexy girl.

  Okay, so I looked identical to my sister, and don’t get me wrong – I’d never had sexual thoughts about her before. But this was different. I was me, but a different me, a me I simply couldn’t take my eyes off.

  On a whim, I turned around and lifted up the hem of my sweater again, watching over my shoulder as I jiggled my booty, unable to believe how good my damn ass looked in these leggings.

  In the reflection, I caught sight of the clock on the wall. It was already nearly five o’ clock now. I needed to decide what to do with my evening. Was I really going to call Michael and go for a drink with him? And if I did, what was I going to wear?

  But I pushed my worries from my mind, my body suddenly overcome by hunger.

  Okay, I decided, I’d go out of the hotel still dressed like this, grab some food from the first junk food place I saw, then come back to my room and decide on my plan for the rest of the night.

  I hitched up my leggings, grabbed my purse and keycard, then set out to find a snack. But at the back of my mind, I knew I didn’t have long to decide about later.

  About Michael ...

  8

  I returned back to my room an hour or so later, laying my shopping bag down on the bed. I’d grabbed something to eat and then, on my way back, remembered that I still needed to pick up some shoes, too.

  Luckily, the hotel wasn’t far from a busy shopping mall, and I’d managed to find a department store that was still open fairly quickly, the shop assistant helping me choose a smart pair of glossy black heels – which I figured could be worn on a date or at a meeting. The heels weren’t huge, but I still knew I’d need a little practice in them back in my room. The whole trip had gone without a hitch.

  I’d actually got kinda used to presenting as a girl by now. It seemed like everyone really accepted me for what they saw, and the more they did, the more my confidence grew. But even so, I was still deliberating about tonight.

  For a start, I still didn’t know if I was actually going to go through with the date. Even though it was just meeting in the hotel bar for drinks, it still seemed like a step too far. Like it might make me gay or something. And also, we all knew where drinks led, didn’t we?

  I was a guy, after all. If a cute girl agreed to meet me for drinks in a hotel bar, I’d be pretty sure I was at least going to get my dick sucked by the end of the night ...

  And on top of all that, what would I even wear if I did decide to go through with it? I couldn’t very well go down in my leggings and sweater. Yet, I guessed that the kinds of things Amy had packed in her suitcase for the presentation wouldn’t be suitable either. I’d seen the sorts of outfits she wore to business meetings – pencil skirts and white blouses, which were all well and good in the workplace but didn’t exactly scream ‘hot date’.

  Still, I decided to at least have a look through the suitcase, just in case.

  I lifted it onto the large, sumptuous bed, then unzipped it, opening the top to reveal a makeup bag and beneath it, a bunch of neatly folded clothes. I pulled out the contents of the case, one by one, examining each item closely.

  First a white silk blouse, just like I’d imagined.

  Then a smart black cardigan, which I guessed was to be worn over the blouse.

  Next a slim-fitting black
pencil skirt.

  But the next item caught my attention. My heart began to race as I pulled it out, holding my breath, hoping beyond hope that ...

  Sure enough, it was a dress. A black dress. A little black dress.

  I had no idea why Amy had packed this item – maybe she’d hoped that she might get lucky on her trip? After all, just like me she was single at the moment, and I knew she went out on occasional dates. But even so, it was still a surprise.

  Beneath the dress, I found a pair of sensible black pantyhose, and then some black thigh-length hold up stockings too, again more the kind of outfit you’d wear on a sexy date than a business meeting.

  And as I pulled out the bunch of panties at the very bottom of the case, these too confirmed my suspicions – there were a couple of plain sporty thongs, the same brand as the one I was wearing, but also in amongst them was the tiniest, skimpiest black g-string I’d ever seen, made of a much more silky, sexy fabric.

  Yep, Amy had clearly been planning (or hoping) to hook up with somebody on her trip! And I realized with a pounding heart that I had everything right here to wear on a date: the g-string, the thigh-high stockings, the little black dress. I could wear the heels and do my makeup in a sexy, seductive way, using some YouTube tutorial – just like Amy had suggested.

  The only question that remained was whether I should meet Michael for a drink at all.

  I sat down on the bed, reaching over to the document wallet and pulling out his business card, staring at the cellphone number printed on it.

  I remembered his warm smile, his white teeth, his thick sensuous lips, his dark eyes, and of course the powerful manly bulk of his body as he’d sat next to me.

  I’d been enjoying experiencing what it was like to be a young woman way more than I’d ever imagined, and now some crazy new part of me yearned to take it a step further – to experience what it would feel like to have a man kiss me, to lust after me, to turn him on with my sexy, feminine body.