by D. L. Savage
I glanced at the clock on the wall – just under an hour left until I needed to call a cab. So I hurriedly pulled off my shirt and boxers, then grabbed a towel and dashed through to the bathroom, running the shower and at the same time searching around for the pink razor Amy normally left on the side of the tub.
Sure enough, there it was, next to the can of shaving foam she used.
How different could shaving your legs be to shaving your face? I wondered. And truth be told, I sometimes shaved my balls, too, and kept my pubic hair nice and trimmed, so I had some previous experience in the art of body shaving.
I jumped under the water, making sure to soap myself good and proper, then with a pang of nervousness I set to work, moving out from beneath the spray of water to the other side of the tub, working a lather of foam all over my left leg and resting my foot on the edge of the tub, just like I’d seen girls do on TV.
I took the razor and began to drag it up my calf, surprised at how easy it was – the blade gliding smoothly, leaving a trail of fresh, smooth pale skin in its wake. I supposed that perhaps it worked so well because I’d never had much body hair to begin with – just a very light dusting blonde fuzz that grew on my shins, thighs and under my arms.
Luckily I had no ass or chest hair to deal with, too, being so pale and maybe not the most testosterone-fuelled guy to begin with.
Once I’d shaved my body, I gave myself another quick rinse, then set about saving my face too, figuring makeup wouldn’t go on too well over stubble.
I managed to make good time, finishing the whole job in just under ten minutes, and after quickly toweling off, I raced back to the pile of clothes on the couch, knowing that it was now or never. Time to get dressed …
I picked up the thong, a simple sporty purple one made of some kind of stretchy shiny material, puzzling at first as to which way round it even went. Then, when I’d figured that part out, I stepped cautiously into it, sliding it up over my thighs and feeling the stretchy material cup my balls and dick really tightly, while at the back, the fabric strip slid right up between my butt cheeks.
I couldn’t help but smile at how stupid I must look right now, trying on my own sister’s thong! At least it wasn’t that uncomfortable; I’d heard girls back in high school always complaining about them, but actually, this wasn’t too bad. Sure, you could kind of feel it there, riding up between your cheeks, but it was a sensation I figured I’d get used to with time.
And anyway, I had to get a move on if I was gonna make that damn taxi. Next I grabbed the bra, and tried a little trick I’d seen girls do when they got dressed in the morning – clipping the back part at my waist like a belt then shuffling it around until it was facing the right way, then pulling it up my body, hooking the straps over my shoulders one by one.
But the cups of the bra gaped emptily at the front and it seemed obviously that my puny pecs weren’t real tits. Then I remembered Amy’s weird comment about her being a B cup and using ‘chicken fillets,’ and my eyes strayed across to the small black box that she’d told me to take. Could these weird fillets be in there, maybe?
I opened it up and sure enough, inside were two skin colored rubber lumps, each about the size of a chicken breast; clearly to be used to pad out a bra.
No shit, I thought, staring down at them, I wonder how many other girls wear these to make their breasts look bigger?
I lifted the fillets out, realizing they were made of some kind of jelly-like silicone substance and I stuffed one carefully into each cup in the bra, surprised at the difference it made. Because now, well, it actually kinda felt – and looked – like I had tits! I reached my hands up to my chest, grabbing one in each palm, feeling them squidge a little, just like real boobs did, and as I bobbed up and down on the spot, I could even feel them jiggling and bouncing, yet staying firmly in the cups of the bra.
Wow, for all the world, it really looked like I had a set of small and perky tits!
It might sound weird, but I was actually kind of enjoying myself now, as I selected on the next item of clothing, surprised at the way these items were transforming my body, actually making it look feminine.
Next was the leggings. They felt so flimsy, not much more than pantyhose, really – nothing at all like the baggy jeans or sweatpants I normally wore. But as I pulled them up over my legs, thighs, then butt, I had to admit, it did feel pretty good the way they held everything in so tight and snug, giving my legs a long, shapely appearance and hugging the cheeks of my ass, giving it a lift.
I reached around to feel my butt, surprised at just how round and perky it felt now, wishing for the first time that I had a mirror to check myself out in.
Finally I pulled on the simple dark green sweater. It wasn’t much different than the kind of thing I might wear, only it smelled sweetly of Amy’s perfume and there was something about the way it hung on my body, the soft bumps of my brand new breasts pushing through at the front and the hem dancing just about in line with the cheeks of my butt in the tight black leggings that I just knew looked totally girly, in a really relaxed, everyday sort of way.
I felt a weird pang of nerves as I walked back through to Amy’s bedroom, wondering if she’d just laugh in my face when she saw me like this. But then I reminded myself just why I was dressed up in the first place. And so, with a deep breath, I reached out and pushed open the door, then stepped inside, forcing a playful smile onto my face to hide my nerves.
“Ta da!” I said, striking a stupid fashion model pose in the doorway, a hand on my hip.
“Perfect!” she croaked back. “Wow, Adam, you look ... great!”
Amy, meanwhile was looking worse by the minute.
“Hey, you sure you’re even gonna be okay while I’m gone?” I asked, concerned.
“I’ll be fine,” she smiled back.
As I started to walk towards her, she held up her hand. “No, no, no, try that again,” she said, “but this time swing your hips more, and take much smaller steps.”
I paced back to where I was and did it again, this time as she suggested; it felt unnatural at first, but I could see what she was getting at. I did feel a little more like I was moving how a girl might.
“And keep your head up, too” she added. “Shoulders back. No slouching!”
After a little more walking practice, Amy had me sit on the bed while she fixed her long blonde hair extensions in. In the months since I’d last held down a job, I’d actually let my own blonde hair grow out almost as much as hers, and when she was done, I almost couldn’t believe what I saw when I went over to the long dress mirror that stood in the corner of her room, to look.
“Holy shit,” I laughed. “I look like ... you!”
It was true, I really did look like Amy. Well, Amy in the morning, before she put any makeup on. But with those few subtle changes – the clothes, the bra, the hair – I could actually see this plan possibly working for the first time.
“That’s the idea, dumbass,” she joked. “Now come over here watch me while I do your makeup.”
So I sat on the bed, holding a little compact mirror, angling it so that I could watch as Amy carefully applied my makeup, talking me through the whole routine, so I’d know what to do tomorrow before the presentation. She showed me that the foundation went on first, then the blusher and contouring, then the setting powder, followed by eye shadow, eyeliner and mascara, then finally lipstick.
“There’s no way in hell I’m going to remember all that,” I groaned.
“You want me to let you in on a little girly secret?” she grinned. “YouTube is your new best friend. There’s thousands of tutorials on there. And I’ve got a makeup kit all packed and ready in the suitcase.”
Again I walked over to the mirror, this time totally blown away by the reflection that greeted me there. She’d done an amazing job, and I couldn’t help but pose a little, pouting and admiring my brand new, totally feminine features.
It was the craziest thing. Fucked up as it sounds, I actually
felt kinda ... sexy.
“Right, you’d better go,” she said, checking the time on her cell. “I’ll call a cab, it should be waiting outside in a few minutes! There’s a bunch of printouts in the front pocket of the suitcase. Should be everything you need. And take my purse. Now go!”
“Okay, wish me luck,” I said, grabbing Amy’s purse and stuffing my cellphone and wallet into it, seeing as my outfit didn’t have any pockets. My heart was suddenly booming as I realized that this wasn’t just some silly dress up game. I was actually about to go out of the apartment and into the world dressed like this.
“Good luck!” she called after me. “Don’t do anything I wouldn’t do.”
“Very funny,” I called back as I slung the purse over my shoulder, then turned and raced to the door, grabbing the suitcase.
But I paused, frozen on the spot as a brand new problem dawned on me.
“What about shoes?” I called out, worried.
My feet were a couple sizes bigger than Amy’s; there was no way in hell I’d fit into a pair of her heels.
“Just wear sneakers for now,” she called back, “and pick up something smart in Boston.”
So I grabbed my black and white low top Converse, figuring they were unisex, and quickly put them on. Then, suitcase in hand and breath clutched in my lungs, I ventured out of the apartment ...
4
“Hi Amy! Going somewhere nice?”
I’d barely closed the door behind me when I heard the voice of Mrs Patterson, the woman who owned the apartment opposite Amy’s. I froze on the spot for a moment, totally taken aback, then quickly composed myself again, pushing my shoulders back just like Amy had taught me, and forcing a smile onto my face as I said, in my best Amy impression, “Hi Mrs Patterson, I’m actually pitching for a job in Boston tomorrow!”
I totally expected her face to wrinkle in disgust and confusion as she figured out that it was actually me, but to my total surprise and amazement, she just continued smiling happily. “How exciting!” she said, warmly. “Well, good luck.”
Just then I heard the honk of the taxicab’s horn outside, and I felt a rush of relief, glad to make my escape while things were still going well.
“Thanks,” I smiled back. “Well, I think that’s for me!”
I grabbed my suitcase and skittered quickly down the two flights of stairs then out to the front of the apartment block where, sure enough, a yellow cab was waiting.
As the driver saw me, he popped open the trunk then got out, and I wheeled the case over towards the back of the car. I’d instinctively reached down to lift the case into the trunk myself when he smiled and shook his head, quickly lifting it up off the floor – as if he thought I wouldn’t be strong enough to do it myself.
For a moment I was confused, then remembered again that I was dressed like a slim, pretty woman and he was obviously trying to be chivalrous. So I smiled back at him and even found myself batting my eyelashes as I murmured, “Why, thank you very much.”
He walked around to open my door for me, and as I climbed into the back of the cab, I couldn’t help but get the distinct feeling that he was checking out my ass.
“To the airport, miss?” he said, as he slipped back into the driver’s seat.
“Yes please,” I smiled back, the soft feminine voice coming surprisingly easy to me now.
As the cab pulled away, I stared out of the window, a smile lingering on my lips as I realized that maybe, just maybe, Amy’s crazy plan might actually work ...
The next challenge was to check in. Once I arrived at the departures hall, I had to stop myself from just dashing the way I normally would. Because it was one thing to race around in my usual fashion, not caring how my body moved, just getting somewhere quickly, but it was a whole other thing to make sure I appeared totally feminine and ladylike at all times.
Again, remembering what Amy had told me, I took small steps, one foot in front of the other, swinging my hips a little as I walked, all the while keeping my back straight and my head held high, as I wheeled the suitcase, trying to find my check in desk. And as I walked, I could feel my breasts (well, my fillets) softly bouncing in my bra, and I could feel the thin strap of the thong sliding between my butt cheeks, which were still hugged tight and snug by the leggings.
From the corner of my eye, I caught sight of a girl about my own age, dressed in a similar outfit, just a sweater and leggings, and it was kind of weird to think that all of a sudden I knew exactly how she felt to be dressed like that. Sure it was casual and comfy, but there was something way more sensual, more feminine, more sexy, about wearing such tight fitting clothes, too, knowing that if I tugged up the hem of my sweater just the teensiest bit, I’d give whoever was behind me a flash of my pert little butt.
But I had no time to continue on thinking such crazy things. From a screen I saw that the flight was already ready to board, and I finally found my check in desk, striding purposefully towards it, fixing what I hoped was a happy, carefree smile on my face.
“Do you have your passport, miss?” the girl on the desk asked me, again showing no sign that she thought me anything other than a real woman.
I felt myself breathe a sigh of relief as I bent down and unzipped the front pocket of the suitcase, where, sure enough, Amy had packed all her paperwork and documents neatly. I rooted around then brought out Amy’s passport, along with the document wallet that I hoped contained the script for her presentation.
I tried to remain totally calm as I handed the girl on the desk the passport and she scanned it in and then looked at me carefully, obviously checking if the girl in the photograph was me.
This was it. The moment of truth.
There was a slight pause, and then her face broke into a friendly smile as she said, “And is this the bag you’d like to check in?”
I nodded, lifting the suitcase onto the weighing station.
“Did you pack this case yourself?” she asked seriously, and I nodded, hoping my face gave nothing of the truth away.
“Very good,” she smiled. “Well, Miss Williams, you’re in Business Class, which has already started boarding. I suggest you make your way through security immediately. Here’s your boarding pass.”
She handed me the pass, taking my suitcase through to her side and fixing on tags.
“Thank you very much,” I said in my best Amy impression.
“Have a good flight, Miss Williams!” she called after me, as I turned and headed toward the departure lounge, hips swinging, small breasts bouncing, and a big excited grin on my face ...
5
“Aisle seat, just up there to the right,” the pretty air stewardess told me as I boarded the plane.
I’d never flown anything other than economy before, and I couldn’t help but feel a little bit fancy as I turned away from the cramped seating behind me then stepped through to the business class area at the front of the plane.
Immediately I could see that it was way more spacious and luxurious, with larger plush-looking seats, just two to each side of the aisle, and a ton more leg room to boot.
And the clientele looked more fancy, too; I realized that I was the only person who wasn’t dressed in smart officewear, as all around me sat suited businessmen and women, some working on laptops, others just relaxing, preparing for the flight.
I found my aisle seat, which was on the right, and there was a guy already sitting in the window seat next to me. He looked up at me, smiling politely and I found myself smiling back at him warmly.
He was about the same age as me, I guessed – early to mid twenties – and he was dressed in an obviously expensive black suit. As I eased myself down into the plush seat next to him, I could smell the spicy scent of his cologne too, the kind of product I’d never worn in my regular life, never being able to afford anything other than Axe.
And, crazy as it sounds, as the plane began to prepare for take off, I found my attention fixing on this stranger next to me, the same way it might normally if I’d sat
down next to a hot chick.
He was handsome. I knew that immediately, just from the one quick glimpse I’d got of his face as he smiled at me – big dark brown eyes, a rugged manly jaw – and he was built too, from what I could tell, his tailored suit seeming to show off the broadness of his shoulders and the sheer masculine bulk of his body, so different to my slight, slender frame.
Don’t get me wrong, I hadn’t forgotten for a moment that I was a guy – I was only pretending to be a girl – but sat there next to my mysterious businessman, I again started to understand what it might feel like to really be a girl: to be so flimsy and slight, and to get turned on by the sheer size and power of a real man.
What’s more, I found that these new thoughts and sensations were actually turning me on too, in a way I totally wasn’t prepared for. It wasn’t just horniness, though, more of a soft sensual pleasure, like I was just languishing in my newfound femininity. But even so, I could feel my cock starting to swell, and I quickly crossed my legs, hoping to hell no bulge had begun to show through my leggings.
For good measure, I pulled out the sheaf of documents that Amy had prepared and began to look at them them.
It was pure Amy to be so well prepared. She’d printed out everything, even an itinerary of the trip – hotel address, check in and out times, numbers for local taxi firms, the address of the pitch meeting, the works …
The pitch.
The reminder of what I was about to do shot through me in a powerful jolt of nerves, totally killing my boner, my whole mind and body now focused again on the daunting task ahead.
As the plane began to rumble down the runway then pick up speed, juddering slightly as it finally took off into the sky, I felt my heart pounding with dread at the thought of presenting a whole twenty minute pitch in front of a room full of strangers, all while dressed as a woman ...
